JP4549690B2 - Herbicidal composition containing 3-phenoxy-4-pyridazinol derivative - Google Patents

Description

  The present invention relates to a herbicidal composition containing as an active ingredient a 3-phenoxy-4-pyridazinol compound, a salt thereof, an ester derivative thereof and another specific compound having herbicidal activity.

  At present, many herbicides have been put to practical use as paddy field herbicides and are widely used as single agents and mixed agents. However, there are many kinds of paddy field weeds, and the weeds and the growth time of each weed are not uniform, and the generation of perennial weeds is particularly long. Therefore, it is very difficult to control all weeds with a single herbicide application. Therefore, as a herbicide, many kinds of weeds including annual and perennial weeds can be killed, that is, the herbicidal spectrum is wide, effective for weeds that have grown, and the herbicidal effect can be maintained for a certain period of time. In addition, the emergence of highly safe drugs in paddy rice is most demanded.

  General formula (I) which is one active ingredient of the present invention:

[Wherein, R ¹ represents a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₂ -C ₆ alkenyl group, a cyano group, C ₂ -C ₇ alkylcarbonyl group, a di (C ₁ -C ₆ alkyl) carbamoyl group, which may be substituted phenyl group (the substituent is a substituent selected from substituent group a.), 5 or 6-membered heterocyclic group (the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and may further contain 1 to 2 nitrogen atoms), C _1- . A C ₆ alkoxy group, an optionally substituted phenoxy group (the substituent is a substituent selected from the following substituent group A) or an optionally substituted 5- or 6-membered heterocyclic oxy group {the heterocyclic ring is Contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and one or two more Of nitrogen atoms. The substituent is a substituent selected from the group consisting of an optionally substituted benzoyl group (the substituent is a substituent selected from the following substituent group A) and a C _{1 to} C ₆ alkyl group. },
R ² is a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a (C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkyl group, a benzoyl group which may be substituted (the substituent is the following substituent group) A substituent selected from A.), a C ₂ -C ₇ alkoxycarbonyl group, an optionally substituted phenoxy group (the substituent is a substituent selected from the following substituent group A), substituted. A good phenylthio group (the substituent is a substituent selected from the following substituent group A) or a tri (C ₁ -C ₆ alkyl) silicon group;
R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, a halogen atom or an optionally substituted C ₁ -C ₆ alkyl group (the substituent is selected from the following substituent group B) A C ₂ -C ₆ alkenyl group which may be substituted (the substituent is a cyano group or a nitro group), a C ₂ -C ₆ alkynyl group, a C ₃ which may be substituted. -C ₆ cycloalkyl group (said substituent is a substituent selected from substituent group C.), C ₄ ~C ₁₀ bicycloalkyl group, a cyano group, a formyl group, C ₂ -C ₇ alkylcarbonyl group , A benzoyl group which may be substituted (the substituent is a substituent selected from the following substituent group A), a carboxyl group, a C _{2 to} C ₇ alkoxycarbonyl group, a carbamoyl group, di (C _{1 to} C _6). Alkyl) carbamoyl group, optionally substituted phenyl A group (the substituent is a substituent selected from the following substituent group A), an optionally substituted 3- to 6-membered heterocyclic group (the heterocyclic ring includes one nitrogen atom, (It contains an oxygen atom or a sulfur atom, may further contain 1 to 2 nitrogen atoms, and may be condensed with a benzene ring. The substituent is a substituent selected from the following substituent group E.) , amino group which may be substituted (the substituent is a substituent selected from substituent group D.), a nitro group, a hydroxyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, (C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkoxy group, optionally substituted phenoxy group (the substituent is substituted with a hydroxyl group or a substituent selected from a halogen atom and a C ₁ -C ₆ alkoxy group) A pyridazinyloxy group), which may be substituted; Ring oxy group (the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and may further contain 1 to 2 nitrogen atoms. is a substituent selected from group E.), which may be substituted phenylsulfonyloxy group (the substituent is a substituent selected from substituent group a.), C ₁ ~C ₆ alkylthio group, A C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group or a tri (C ₁ -C ₆ alkyl) silicon group, or R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are Two adjacent groups may be substituted together with the carbon atom to which each is bonded. The 3- to 6-membered cyclic hydrocarbon group (the cyclic hydrocarbon is selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom) Interrupted by one or two identical or different heteroatoms There. The substituents are halogen atom, C ₁ -C ₆ alkyl group, a hydroxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, a oxo group, hydroxyimino group or a C ₁ -C ₆ alkoxyimino group If the C ₁ -C ₆ alkyl group is substituted, may form a new 3-membered ring with other C ₁ -C ₆ alkyl group or a carbon atom on the ring. )
m and n each independently represent 0 or 1,
Substituent Group A consists of halogen atoms, C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₃ -C ₆ cycloalkyl group, a cyano group and a tri (C ₁ -C ₆ alkyl) silyl group A group,
Substituent group B, a halogen atom, C ₃ -C ₆ cycloalkyl group, a cyano group, C ₂ -C ₇ alkylcarbonyl group, C ₂ -C ₇ alkoxycarbonyl group, a phenyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, consisting of C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₄ alkylenedioxy group, hydroxyimino group and C ₁ -C ₆ alkoxyimino group A group,
Substituent group C includes a halogen atom, an optionally substituted C ₁ -C ₆ alkyl group (the substituent is a substituent selected from the above substituent group B), a C ₃ -C ₆ cycloalkyl group, C ₂ -C ₆ alkenyl group, cyano group, C ₂ -C ₇ alkylcarbonyl group, benzoyl group, carboxyl group, C ₂ -C ₇ alkoxycarbonyl group, carbamoyl group, di (C ₁ -C ₆ alkyl) carbamoyl group, A phenyl group which may be substituted (the substituent is a substituent selected from the above substituent group A), a 5- or 6-membered heterocyclic group (the heterocyclic ring has one nitrogen atom in the ring; , An oxygen atom or a sulfur atom, and further may contain 1 to 2 nitrogen atoms.), An amino group which may be substituted (the substituent is a substituent selected from the following substituent group D) .), a nitro group, a hydroxyl group, C ₁ -C ₆ alkoxy Group, a C ₁ -C ₆ haloalkoxy group, a phenoxy group, C ₁ -C ₆ alkylthio group, a phenylthio group, C ₁ -C ₆ alkylsulfinyl group consisting Le group and C ₁ -C ₆ alkylsulfonyl group,
Substituent group D is, C ₁ -C ₆ alkyl group, C ₂ -C ₇ alkylcarbonyl group, C ₂ -C ₇ alkoxycarbonyl group, a di (C ₁ -C ₆ alkyl) carbamoyl group and C ₁ -C ₆ alkyl A group consisting of a sulfonyl group,
Substituent group E includes a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a hydroxyl group, an optionally substituted phenylsulfonyl group (the substituent is a substituent selected from substituent group A above) And di (C ₁ -C ₆ alkyl) sulfamoyl groups. ] The compound represented by these, its salt, and its ester derivative 3-phenoxy-4-pyridazinol derivative [Hereinafter abbreviated as compound (I)] is a novel compound.

  Another active ingredient, 3- (2-chloro-4-mesylbenzoyl) -2-phenylthiobicyclo [3.2.1] oct-2-en-4-one [hereinafter abbreviated as compound (B)]. General name benzobicyclone], N, N-diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide [hereinafter abbreviated as compound (C). General name Cavenstrol] is a known herbicidal compound and is described in The Pesticide Manual 12th Edition 82, pages 128-129, respectively.

  Compound (B) has a high effect on annual weeds (Nobies), annual broad-leaved weeds, and perennial weeds such as fireflies and scallops, but the herbicidal effect on some broad-leaved weeds and perennial weeds is not sufficient. .

Compound (C) has a high effect on annual weeds (Nobies) and annual broadleaf weeds, but the herbicidal effect on some broadleaf and perennial weeds is not sufficient.
The Pesticide Manual 12th Edition 82, pp. 128-129

  In order to improve the above-mentioned problems of conventional herbicides, the present inventors completely control various weeds with a single spray, and have a high level of safety against paddy rice. As a result of continuous search for low herbicides, the 3-phenoxy-4-pyridazinol derivative and 3- (2-chloro-4-mesylbenzoyl) -2-phenylthiobicyclo [3.2.1] oct-2-ene By combining -4-one and / or N, N-diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide as an active ingredient, the herbicidal spectrum is expanded and synergistic As a result, it was found that important weeds can be controlled with a smaller amount of active ingredients, and the present invention was completed.

  The present invention is directed to general formula (I):

[Wherein, R ¹ represents a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₂ -C ₆ alkenyl group, a cyano group, C ₂ -C ₇ alkylcarbonyl group, a di (C ₁ -C ₆ alkyl) carbamoyl group, which may be substituted phenyl group (the substituent is a substituent selected from substituent group a.), 5 or 6-membered heterocyclic group (the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and may further contain 1 to 2 nitrogen atoms), C _1- . A C ₆ alkoxy group, an optionally substituted phenoxy group (the substituent is a substituent selected from the following substituent group A) or an optionally substituted 5- or 6-membered heterocyclic oxy group {the heterocyclic ring is Contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and one or two more Of nitrogen atoms. The substituent is a substituent selected from the group consisting of an optionally substituted benzoyl group (the substituent is a substituent selected from the following substituent group A) and a C _{1 to} C ₆ alkyl group. },
R ² is a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a (C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkyl group, a benzoyl group which may be substituted (the substituent is the following substituent group) A substituent selected from A.), a C ₂ -C ₇ alkoxycarbonyl group, an optionally substituted phenoxy group (the substituent is a substituent selected from the following substituent group A), substituted. A good phenylthio group (the substituent is a substituent selected from the following substituent group A) or a tri (C ₁ -C ₆ alkyl) silicon group;
R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, a halogen atom or an optionally substituted C ₁ -C ₆ alkyl group (the substituent is selected from the following substituent group B) A C ₂ -C ₆ alkenyl group which may be substituted (the substituent is a cyano group or a nitro group), a C ₂ -C ₆ alkynyl group, a C ₃ which may be substituted. -C ₆ cycloalkyl group (said substituent is a substituent selected from substituent group C.), C ₄ ~C ₁₀ bicycloalkyl group, a cyano group, a formyl group, C ₂ -C ₇ alkylcarbonyl group , A benzoyl group which may be substituted (the substituent is a substituent selected from the following substituent group A), a carboxyl group, a C _{2 to} C ₇ alkoxycarbonyl group, a carbamoyl group, di (C _{1 to} C _6). Alkyl) carbamoyl group, optionally substituted phenyl A group (the substituent is a substituent selected from the following substituent group A), an optionally substituted 3- to 6-membered heterocyclic group (the heterocyclic ring includes one nitrogen atom, (It contains an oxygen atom or a sulfur atom, may further contain 1 to 2 nitrogen atoms, and may be condensed with a benzene ring. The substituent is a substituent selected from the following substituent group E.) , amino group which may be substituted (the substituent is a substituent selected from substituent group D.), a nitro group, a hydroxyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, (C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkoxy group, optionally substituted phenoxy group (the substituent is substituted with a hydroxyl group or a substituent selected from a halogen atom and a C ₁ -C ₆ alkoxy group) A pyridazinyloxy group), which may be substituted; Ring oxy group (the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and may further contain 1 to 2 nitrogen atoms. is a substituent selected from group E.), which may be substituted phenylsulfonyloxy group (the substituent is a substituent selected from substituent group a.), C ₁ ~C ₆ alkylthio group, A C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group or a tri (C ₁ -C ₆ alkyl) silicon group, or R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are Two adjacent groups may be substituted together with the carbon atom to which each is bonded. The 3- to 6-membered cyclic hydrocarbon group (the cyclic hydrocarbon is selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom) Interrupted by one or two identical or different heteroatoms There. The substituents are halogen atom, C ₁ -C ₆ alkyl group, a hydroxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, a oxo group, hydroxyimino group or a C ₁ -C ₆ alkoxyimino group If the C ₁ -C ₆ alkyl group is substituted, may form a new 3-membered ring with other C ₁ -C ₆ alkyl group or a carbon atom on the ring. )
m and n each independently represent 0 or 1,
Substituent Group A consists of halogen atoms, C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₃ -C ₆ cycloalkyl group, a cyano group and a tri (C ₁ -C ₆ alkyl) silyl group A group,
Substituent group B, a halogen atom, C ₃ -C ₆ cycloalkyl group, a cyano group, C ₂ -C ₇ alkylcarbonyl group, C ₂ -C ₇ alkoxycarbonyl group, a phenyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, consisting of C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₄ alkylenedioxy group, hydroxyimino group and C ₁ -C ₆ alkoxyimino group A group,
Substituent group C includes a halogen atom, an optionally substituted C ₁ -C ₆ alkyl group (the substituent is a substituent selected from the above substituent group B), a C ₃ -C ₆ cycloalkyl group, C ₂ -C ₆ alkenyl group, cyano group, C ₂ -C ₇ alkylcarbonyl group, benzoyl group, carboxyl group, C ₂ -C ₇ alkoxycarbonyl group, carbamoyl group, di (C ₁ -C ₆ alkyl) carbamoyl group, A phenyl group which may be substituted (the substituent is a substituent selected from the above substituent group A), a 5- or 6-membered heterocyclic group (the heterocyclic ring has one nitrogen atom in the ring; , An oxygen atom or a sulfur atom, and further may contain 1 to 2 nitrogen atoms.), An amino group which may be substituted (the substituent is a substituent selected from the following substituent group D) .), a nitro group, a hydroxyl group, C ₁ -C ₆ alkoxy Group, a C ₁ -C ₆ haloalkoxy group, a phenoxy group, C ₁ -C ₆ alkylthio group, a phenylthio group, C ₁ -C ₆ alkylsulfinyl group consisting Le group and C ₁ -C ₆ alkylsulfonyl group,
Substituent group D is, C ₁ -C ₆ alkyl group, C ₂ -C ₇ alkylcarbonyl group, C ₂ -C ₇ alkoxycarbonyl group, a di (C ₁ -C ₆ alkyl) carbamoyl group and C ₁ -C ₆ alkyl A group consisting of a sulfonyl group,
Substituent group E includes a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a hydroxyl group, an optionally substituted phenylsulfonyl group (the substituent is a substituent selected from substituent group A above) And di (C ₁ -C ₆ alkyl) sulfamoyl groups. ]
And one or more 3-phenoxy-4-pyridazinol derivatives selected from the group consisting of a compound represented by the formula: salt or ester derivative thereof; and 3- (2-chloro-4-mesylbenzoyl) -2 -Phenylthiobicyclo [3.2.1] oct-2-en-4-one and / or N, N-diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide as active ingredients It is a herbicidal composition to contain.

  In the present invention, the “halogen atom” is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a chlorine atom or a bromine atom. And even more preferred is a chlorine atom.

In the present invention, the “C ₁ -C ₆ alkyl group” is a linear or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl. , T-butyl, pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, hexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl, 2 , 2-dimethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl or 2-ethylbutyl group, preferably having 1 to It is four straight or branched chain alkyl group (C ₁ -C ₄ alkyl group), more preferably 1 to 3 carbon atoms straight or branched chain alkyl group (C ₁ -C ₃ alkyl Group), and even more preferably, 1 to 2 carbon atoms. An alkyl group (C ₁ -C ₂ alkyl group), particularly preferably a methyl group.

In the present invention, the “C ₁ -C ₆ haloalkyl group” is the above-mentioned “C ₁ -C ₆ alkyl group” substituted with 1 to 5 of the same or different “halogen atoms”, and examples thereof include chloromethyl and dichloromethyl. , Trichloromethyl, 1-chloroethyl, 2-chloroethyl, 2,2,2-trichloroethyl, 1-chloropropyl, 3-chloropropyl, 1-chlorobutyl, 4-chlorobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, 1 -Fluoroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, fluorochloromethyl, bromomethyl, 1-bromoethyl, 2-bromoethyl or iodomethyl group, preferably a fluorine atom, C ₁ -C ₃ alkyl group one to three substituents the same or different selected from the group consisting of chlorine atom and bromine atom is substituted There, more preferably, the same one to three, fluorine atoms C ₁ -C ₂ alkyl radical or a chlorine atom is substituted, further preferably more, fluoromethyl, difluoromethyl, trifluoromethyl or 2 2,2-trichloroethyl group, particularly preferably a trifluoromethyl group.

In the present invention, the “C ₃ -C ₆ cycloalkyl group” is a cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl group, preferably a cyclopropyl or cyclobutyl group, and more preferably a cyclopropyl group. .

In the present invention, the “C ₂ -C ₆ alkenyl group” is a linear or branched alkenyl group having 2 to 6 carbon atoms, such as vinyl, 1-methylvinyl, allyl, 1-propenyl, 1-propenyl, Methyl-1-propenyl, 2-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-ethyl-2-propenyl, 2-butenyl, 1-methyl-2-butenyl, 2-methyl- 2-butenyl, 1-ethyl-2-butenyl, 3-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 1-ethyl-3-butenyl, 2-pentenyl, 1-methyl-2- Pentenyl, 2-methyl-2-pentenyl, 3-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 4-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, It may be a 2-hexenyl, 3-hexenyl, 4-hexenyl or 5-hexenyl group, preferably a linear or branched alkenyl having 2 to 4 carbon atoms. Le is a group (C ₂ -C ₄ alkenyl group), more preferably, vinyl, 1-methylvinyl, allyl, 2-propenyl or 1-methyl-2-propenyl group.

In the present invention, the “C ₂ -C ₇ alkylcarbonyl group” is a carbonyl group to which the “C ₁ -C ₆ alkyl group” is bonded, and examples thereof include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl, It can be a hexanoyl or heptanoyl group, and is preferably a carbonyl group (C ₂ -C ₅ alkylcarbonyl group) to which a linear or branched alkyl group having 1 to 4 carbon atoms is bonded, and even more preferably , A carbonyl group to which a linear or branched alkyl group having 1 to 3 carbon atoms is bonded (C _{2 to} C ₄ alkylcarbonyl group), particularly preferably an acetyl, propionyl, valeryl or pivaloyl group, Most preferred is an acetyl group.

In the present invention, the “di (C ₁ -C ₆ alkyl) carbamoyl group” is a carbamoyl group in which two identical or different “C ₁ -C ₆ alkyl groups” are bonded to a nitrogen atom. , Methylethylcarbamoyl, diethylcarbamoyl, dipropylcarbamoyl, dibutylcarbamoyl or dihexylcarbamoyl group, preferably a carbamoyl group in which the same two linear or branched alkyl groups having 1 to 3 carbon atoms are bonded {Di (C ₁ -C ₃ alkyl) carbamoyl group}, more preferably a dimethylcarbamoyl group or diethylcarbamoyl group, and even more preferably a dimethylcarbamoyl group.

In the present invention, the “tri (C ₁ -C ₆ alkyl) silicon group” is a silicon atom to which three identical or different “C ₁ -C ₆ alkyl groups” are bonded, and examples thereof include trimethylsilyl, triethylsilyl, It may be a triisopropylsilyl, dimethylisopropylsilyl, t-butyldimethylsilyl or trihexylsilyl group, preferably having the same or different 3 to 1 C 1-3 straight or branched alkyl groups attached thereto. A silicon atom {tri (C ₁ -C ₃ alkyl) silicon group}, more preferably a trimethylsilyl or dimethylisopropylsilyl group, and even more preferably a trimethylsilyl group.

In the present invention, “optionally substituted phenyl group (the substituent is a substituent selected from Substituent Group A)” means the “halogen atom”, the “C ₁ -C ₆ alkyl group”, The same or different selected from the group consisting of the “C ₁ -C ₆ haloalkyl group”, the “C ₃ -C ₆ cycloalkyl group”, the cyano group, and the “tri (C ₁ -C ₆ alkyl) silicon group”. 1 to 5 substituents may be substituted phenyl groups, such as phenyl, fluorophenyl, difluorophenyl, trifluorophenyl, chlorophenyl, dichlorophenyl, trichlorophenyl, fluorochlorophenyl, methylphenyl, dimethylphenyl, trimethylphenyl, Tetramethylphenyl, pentamethylphenyl, ethylphenyl, fluoro (methyl) phenyl, chloro (me ) Phenyl, bromo (methyl) phenyl, cyclopropylphenyl, cyclopropyl (fluoro) phenyl, chloro (cyclopropyl) phenyl, cyclopropyl (methyl) phenyl, (trifluoromethyl) phenyl or fluoro (trifluoromethyl) phenyl groups in and obtained, preferably a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, "a fluorine atom, the same or different 1-3 selected from the group consisting of chlorine and bromine C ₁ -C ₃ alkyl group "substituted group is substituted, C ₃ -C ₄ cycloalkyl group, the same or different 1 to 3 selected from cyano group and a tri (C ₁ -C ₃ alkyl) group consisting of silicon group Is an optionally substituted phenyl group, more preferably phenyl, chlorophenyl, methylphenyl, trifluorophenyl or cyanophenyl. A phenyl group.

  In the present invention, “5- or 6-membered heterocyclic group (the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and further contains 1 to 2 nitrogen atoms. Is a 5- to 6-membered heterocyclic group which contains one nitrogen atom, oxygen atom or sulfur atom as a hetero atom, and may further contain 1 to 2 nitrogen atoms, For example, it may be a furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, triazolyl, pyranyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl or triazinyl group, preferably a 5-membered heterocyclic group The ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring.), More preferably a furyl or thienyl group.

In the present invention, the “C ₁ -C ₆ alkoxy group” is a linear or branched alkoxy group having 1 to 6 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s- Butoxy, t-butoxy, pentoxy, isopentoxy, 2-methylbutoxy, neopentoxy, 1-ethylpropoxy, hexyloxy, 4-methylpentoxy, 3-methylpentoxy, 2-methylpentoxy, 1-methylpentoxy, 3 , 3-dimethylbutoxy, 2,2-dimethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy or 2-ethylbutoxy group, Preferred is a straight or branched alkoxy group having 1 to 3 carbon atoms (C ₁ -C ₃ alkoxy group), more preferred is a methoxy or ethoxy group, and even more preferred. Is a methoxy group.

In the present invention, “optionally substituted phenoxy group (the substituent is a substituent selected from Substituent Group A)” means the “halogen atom”, the “C ₁ -C ₆ alkyl group”, The same or different selected from the group consisting of the “C ₁ -C ₆ haloalkyl group”, the “C ₃ -C ₆ cycloalkyl group”, the cyano group and the “tri (C ₁ -C ₆ alkyl) silicon group”. 1 to 5 substituents may be substituted phenoxy groups, such as phenoxy, fluorophenoxy, difluorophenoxy, trifluorophenoxy, chlorophenoxy, dichlorophenoxy, trichlorophenoxy, fluorochlorophenoxy, methylphenoxy, dimethylphenoxy, Trimethylphenoxy, tetramethylphenoxy, pentamethylphenoxy, ethylphenoxy, Oro (methyl) phenoxy, chloro (methyl) phenoxy, bromo (methyl) phenoxy, cyclopropylphenoxy, cyclopropyl (fluoro) phenoxy, chloro (cyclopropyl) phenoxy, cyclopropyl (methyl) phenoxy, (trifluoromethyl) phenoxy or fluoro be a (trifluoromethyl) phenoxy group, preferably a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, "a fluorine atom, the same selected from the group consisting of chlorine and bromine Or a C ₁ -C ₃ alkyl group substituted with 1 to 3 different substituents ”, a C ₃ -C ₄ cycloalkyl group, a cyano group, and a tri (C ₁ -C ₃ alkyl) silicon group. Are the same or different 1 to 3 substituents which may be substituted, more preferably phenoxy, chlorophene Noxy, methylphenoxy, trifluorophenoxy or cyanophenoxy groups.

In the present invention, “optionally substituted benzoyl group (the substituent is a substituent selected from Substituent Group A)” means the “halogen atom”, the “C ₁ -C ₆ alkyl group”, The same or different selected from the group consisting of the “C ₁ -C ₆ haloalkyl group”, the “C ₃ -C ₆ cycloalkyl group”, the cyano group, and the “tri (C ₁ -C ₆ alkyl) silicon group”. 1 to 5 substituents are optionally substituted benzoyl groups such as benzoyl, fluorobenzoyl, difluorobenzoyl, trifluorobenzoyl, chlorobenzoyl, dichlorobenzoyl, trichlorobenzoyl, fluorochlorobenzoyl, methylbenzoyl, dimethylbenzoyl, Trimethylbenzoyl, tetramethylbenzoyl, pentamethylbenzoyl, ethylbenzoyl, Oro (methyl) benzoyl, chloro (methyl) benzoyl, bromo (methyl) benzoyl, cyclopropylbenzoyl, cyclopropyl (fluoro) benzoyl, chloro (cyclopropyl) benzoyl, cyclopropyl (methyl) benzoyl, (trifluoromethyl) benzoyl or fluoro be a (trifluoromethyl) benzoyl group, preferably a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, "a fluorine atom, the same selected from the group consisting of chlorine and bromine Or a C ₁ -C ₃ alkyl group substituted with 1 to 3 different substituents ”, a C ₃ -C ₄ cycloalkyl group, a cyano group, and a tri (C ₁ -C ₃ alkyl) silicon group. The same or different 1 to 3 substituents are optionally substituted benzoyl groups, more preferably benzoyl, chloroben A zoyl, dichlorobenzoyl, methylbenzoyl, trifluorobenzoyl or cyanobenzoyl group.

In the present invention, “optionally substituted 5- or 6-membered heterocyclic oxy group {the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and further 1 to 2 nitrogen atoms The substituent may be a benzoyl group (the substituent is a substituent selected from Substituent Group A) and a C ₁ -C ₆ alkyl group which may be substituted. Is a substituent selected from the above-mentioned “benzoyl group which may be substituted (the substituent is a substituent selected from substituent group A)” and “C ₁ -C ₆ alkyl group”. May be substituted by the same or different 1 to 3 substituents selected from the group consisting of “as a hetero atom, containing one nitrogen atom, oxygen atom or sulfur atom, and further 1 to 2 nitrogen atoms A 5- to 6-membered heterocyclic oxy group which may contain Fluorine atom, chlorine atom, bromine atom, C ₁ -C ₃ alkyl group, "a fluorine atom, C ₁ ~ in which one to three substituents the same or different selected from the group consisting of chlorine atom and bromine atom is substituted The same or different 1 to 3 substituents selected from the group consisting of “C ₃ alkyl group”, C ₃ -C ₄ cycloalkyl group, cyano group and tri (C ₁ -C ₃ alkyl) silicon group are substituted. Substituted with a good benzoyl group, as well as the same two C ₁ -C ₃ alkyl groups, “contains one nitrogen atom, oxygen atom or sulfur atom as a hetero atom, and one more nitrogen atom A 5-membered heterocyclic oxy group "which may contain, more preferably a benzoyl group substituted by two chlorine atoms and two C ₁ -C ₂ alkyl groups A pyrazolyloxy group;

In the present invention, the “(C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkyl group” is the “C ₁ -C ₆ alkyl group” substituted by _{one of the} “C ₁ -C ₆ alkoxy groups”. Yes, for example, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, s-butoxymethyl, t-butoxymethyl, pentyloxymethyl, hexyloxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, methoxypropyl, methoxy butyl, be a methoxy pentyl or methoxy hexyl, preferably, a single C ₁ of -C ₃ C ₁ -C ₆ alkyl group which alkoxy group is substituted, more preferably, methoxyethyl, ethoxyethyl or An ethoxymethyl group.

In the present invention, the “C ₂ -C ₇ alkoxycarbonyl group” is a carbonyl group to which the “C ₁ -C ₆ alkoxy group” is bonded, and examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxy Carbonyl, isobutoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, pentoxycarbonyl, isopentoxycarbonyl, 2-methylbutoxycarbonyl, neopentoxycarbonyl, 1-ethylpropoxycarbonyl, hexyloxycarbonyl, 4-methylpen Toxylcarbonyl, 3-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 1-methylpentoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1, 2- Methyl-butoxycarbonyl, 1,3-dimethyl-butoxycarbonyl, 2,3-dimethylbutoxy be a carbonyl or 2-ethyl-butoxycarbonyl group, preferably, C ₁ -C ₃ carbonyl groups alkoxy group is bonded (C ₂ ~ a C ₄ alkoxycarbonyl group), more preferably a methoxycarbonyl or ethoxycarbonyl group, even more preferably more, a methoxycarbonyl group.

In the present invention, the “optionally substituted phenylthio group (the substituent is a substituent selected from Substituent Group A)” means the “halogen atom”, the “C ₁ -C ₆ alkyl group”, The same or different selected from the group consisting of the “C ₁ -C ₆ haloalkyl group”, the “C ₃ -C ₆ cycloalkyl group”, the cyano group and the “tri (C ₁ -C ₆ alkyl) silicon group”. 1 to 5 substituents may be substituted phenylthio groups such as phenylthio, fluorophenylthio, difluorophenylthio, trifluorophenylthio, chlorophenylthio, dichlorophenylthio, trichlorophenylthio, fluorochlorophenylthio, methylphenyl Thio, dimethylphenylthio, trimethylphenylthio, tetramethylphenylthio, pentamethylphenol Ruthio, ethylphenylthio, fluoro (methyl) phenylthio, chloro (methyl) phenylthio, bromo (methyl) phenylthio, cyclopropylphenylthio, cyclopropyl (fluoro) phenylthio, chloro (cyclopropyl) phenylthio, cyclopropyl (methyl) phenylthio, It is a (trifluoromethyl) phenylthio or fluoro (trifluoromethyl) phenylthio group, preferably, a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, "a fluorine atom, chlorine atom and bromine atom C ₁ -C ₃ alkyl group "1-3 substituents selected same or different from the group is substituted composed, C ₃ -C ₄ cycloalkyl group, a cyano group and a tri (C ₁ -C ₃ alkyl) Feni which may be substituted with 1 to 3 identical or different substituents selected from the group consisting of silicon groups More preferably a phenylthio group, a chlorophenylthio group, a methylphenylthio group, a trifluorophenylthio group, or a cyanophenylthio group.

In the present invention, the “C ₁ -C ₆ alkylthio group” is a linear or branched alkylthio group having 1 to 6 carbon atoms, such as methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, s -Butylthio, t-butylthio, pentylthio, isopentylthio, 2-methylbutylthio, neopentylthio, 1-ethylpropylthio, hexylthio, 4-methylpentylthio, 3-methylpentylthio, 2-methylpentylthio, 1 -Methylpentylthio, 3,3-dimethylbutylthio, 2,2-dimethylbutylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,3-dimethyl be a butylthio or 2-ethylbutylthio group, preferably a straight-chain or branched alkylthio group having 1 to 3 carbon atoms (C ₁ -C ₃ alkylthio group), More preferred is a methylthio or ethylthio group, and even more preferred is a methylthio group.

In the present invention, the “C ₁ -C ₆ alkylsulfinyl group” is a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butyl Sulfinyl, isobutylsulfinyl, s-butylsulfinyl, t-butylsulfinyl, pentylsulfinyl, isopentylsulfinyl, 2-methylbutylsulfinyl, neopentylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 4-methylpentylsulfinyl, 3-methyl Pentylsulfinyl, 2-methylpentylsulfinyl, 1-methylpentylsulfinyl, 3,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethyl It can be a butylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl or 2-ethylbutylsulfinyl group, preferably a linear or branched alkylsulfinyl group having 1 to 3 carbon atoms (C ₁ -C ₃ alkylsulfinyl group), more preferably a methylsulfinyl or ethylsulfinyl group, and even more preferably a methylsulfinyl group.

In the present invention, the “C ₁ -C ₆ alkylsulfonyl group” is a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms, such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butyl Sulfonyl, isobutylsulfonyl, s-butylsulfonyl, t-butylsulfonyl, pentylsulfonyl, isopentylsulfonyl, 2-methylbutylsulfonyl, neopentylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 4-methylpentylsulfonyl, 3-methyl Pentylsulfonyl, 2-methylpentylsulfonyl, 1-methylpentylsulfonyl, 3,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3 -Dimethylbutylsulfo Le, be a 2,3-dimethyl-butylsulfonyl or 2-ethyl-butylsulfonyl group, preferably a linear or branched alkylsulfonyl group (C ₁ -C ₃ alkylsulfonyl group) having 1 to 3 carbon atoms And more preferably a methylsulfonyl or ethylsulfonyl group, and even more preferably a methylsulfonyl group.

In the present invention, the “C ₁ -C ₄ alkylenedioxy group” is a linear or branched alkylenedioxy group having 1 to 4 carbon atoms, such as methylenedioxy, ethylenedioxy, propylenedioxy. , Trimethylenedioxy or tetramethylenedioxy group, preferably an alkylenedioxy group having 1 to 2 carbon atoms, and more preferably a 1,2-ethylenedioxy group.

In the present invention, the “C ₁ -C ₆ alkoxyimino group” is a linear or branched alkoxyimino group having 1 to 6 carbon atoms, and examples thereof include methoxyimino, ethoxyimino, propoxyimino, isopropoxyimino, Butoxyimino, isobutoxyimino, s-butoxyimino, t-butoxyimino, pentoxyimino, isopentoxyimino, 2-methylbutoxyimino, neopentoxyimino, 1-ethylpropoxyimino, hexyloxyimino, 4-methylpentoxy Imino, 3-methylpentoxyimino, 2-methylpentoxyimino, 1-methylpentoxyimino, 3,3-dimethylbutoxyimino, 2,2-dimethylbutoxyimino, 1,1-dimethylbutoxyimino, 1,2 -Dimethylbutoxyimino, 1,3-dimethylbutoxyimino, 2,3-dimethylbutoxyimino or 2-ethylbut It is a Shiimino group, preferably a straight or branched alkoxyimino group having 1 to 3 carbon atoms (C ₁ -C ₃ alkoxyimino group), more preferably, methoxyimino or ethoxyimino group And even more preferred is a methoxyimino group.

In the present invention, the “substituted C ₁ -C ₆ alkyl group (the substituent is a substituent selected from Substituent Group B)” is the above “halogen atom” or “C ₃ -C ₆ cycloalkyl group ", a cyano group, wherein" C ₂ -C ₇ alkylcarbonyl group ", the" C ₂ -C ₇ alkoxycarbonyl group ", phenyl group, wherein" C ₁ -C ₆ alkoxy group ", the "C ₁ -C ₆ alkylthio group", the "C ₁ -C ₆ alkylsulfinyl group", the "C ₁ -C ₆ alkylsulfonyl group", the "C ₁ -C ₄ alkylenedioxy group", hydroxyimino group Or the “C ₁ -C ₆ alkyl group” which may be substituted by the “C ₁ -C ₆ alkoxyimino group”, for example, fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trichloroethyl , Siku Ropropylmethyl, cyanomethyl, acetylmethyl, acetylethyl, methoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylmethyl, ethoxycarbonylethyl, benzyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, methylthioethyl, ethylthio It may be methyl, ethylthioethyl, methylsulfinylmethyl, methylsulfonylmethyl, 2- (1,3-dioxolanyl), hydroxyiminomethyl or methoxyiminomethyl group, preferably consisting of a fluorine atom, a chlorine atom and a bromine atom C ₁ -C ₃ alkyl group one to three substituents the same or different from selected from the group is substituted, or, C ₃ -C ₄ cycloalkyl group, a cyano group, C ₂ -C ₄ alkylcarbonyl group, C ₂ ~C ₄ an alkoxycarbonyl Carbonyl group, a phenyl group, C ₁ -C ₃ alkoxy groups, C ₁ -C ₃ alkylthio group, C ₁ -C ₃ alkylsulfinyl group, C ₁ -C ₃ alkylsulfonyl groups, C ₁ -C ₂ alkylenedioxy group, A hydroxyimino group or a C ₁ -C ₃ alkyl group that may be substituted by a C ₁ -C ₃ alkoxyimino group, and more preferably the same 1 to 3 C ₁ substituted with fluorine atoms or chlorine atoms. -C ₂ alkyl group, or a cyclopropyl group, a cyano group, C ₂ -C ₃ alkylcarbonyl group, C ₂ -C ₃ alkoxycarbonyl group, a phenyl group, C ₁ -C ₂ alkoxy group, C ₁ -C ₂ alkylthio group, C ₁ -C ₂ alkylsulfinyl group, C ₁ -C ₂ alkylsulfonyl group, an ethylenedioxy group, hydroxyimino group or C ₁ -C ₂ alkoxyimino group may C ₁ ~ to be substituted It is a _2-alkyl group.

In the present invention, the “substituted C ₂ -C ₆ alkenyl group (the substituent is a cyano group or a nitro group)” refers to the “C ₂ -C ₆ alkenyl group substituted by a cyano group or a nitro group”. a ", preferably a C ₂ -C ₃ alkenyl group cyano group or a nitro group is substituted, more preferably a cyanovinyl or nitrovinyl group.

In the present invention, the “C ₂ -C ₆ alkynyl group” is a linear or branched alkynyl group having 2 to 6 carbon atoms, and examples thereof include ethynyl, 2-propynyl, 1-methyl-2-propynyl, 1 -Ethyl-2-propynyl, 2-butynyl, 1-methyl-2-butynyl, 1-ethyl-2-butynyl, 3-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-ethyl -3-butynyl, 2-pentynyl, 1-methyl-2-pentynyl, 1-ethyl-2-pentynyl, 3-pentynyl, 1-methyl-3-pentynyl, 2-methyl-3-pentynyl, 4-pentynyl, 1 -Methyl-4-pentynyl, 2-methyl-4-pentynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl or 5-hexynyl, preferably a straight or branched chain having 3 to 4 carbon atoms a-chain alkynyl groups (C ₃ -C ₄ alkynyl group), more preferably ethynyl, 1-propynyl or 2-propynyl.

In the present invention, “an amino group which may be substituted (the substituent is a substituent selected from Substituent Group D)” refers to the “C ₁ -C ₆ alkyl group” and the “C ₂ -C”. Selected from the group consisting of “ ₇ alkylcarbonyl group”, “C ₂ -C ₇ alkoxycarbonyl group”, “di (C ₁ -C ₆ alkyl) carbamoyl group” and “C ₁ -C ₆ alkylsulfonyl group”. An amino group which may be substituted by one or two identical or different substituents, for example, amino, methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, s-butylamino, t- Butylamino, pentylamino, isopentylamino, (2-methylbutyl) amino, neopentylamino, (1-ethylpropyl) amino, hexylamino, (4-methylpentyl) Mino, (3-methylpentyl) amino, (2-methylpentyl) amino, (1-methylpentyl) amino, (3,3-dimethylbutyl) amino, (2,2-dimethylbutyl) amino, (1,1 -Dimethylbutyl) amino, (1,2-dimethylbutyl) amino, (1,3-dimethylbutyl) amino, (2,3-dimethylbutyl) amino, (2-ethylbutyl) amino, dimethylamino, (methyl) ( Ethyl) amino, diethylamino, dipropylamino, (methyl) (isopropyl) amino, diisopropylamino, dibutylamino, diisobutylamino, dis-butylamino, di-t-butylamino, dipentylamino, diisopentylamino, di (2 -Methylbutyl) amino, dineopentylamino, di (1-ethylpropyl) amino, dihexylamino, di (4-methylpentyl) amino, di (3-methylpentyl) amino, di (2-methylpentyl) amino, di (1-methylpentyl) amino, di (3,3-dimethylbutyl) amino, di (2,2-dimethylbutyl) amino, di (1,1-dimethylbutyl) amino, di (1,2-dimethylbutyl) Amino, di (1,3-dimethylbutyl) amino, di (2,3-dimethylbutyl) amino, di (2-ethylbutyl) amino, acetylamino, propionylamino, butanoylamino, (2-methylpropanoyl) amino , Pentanoylamino, (2,2-dimethylpropanoyl) amino, (2,2-dimethylpentanoyl) amino, (2-methylbutanoyl) amino, (3-methylbutanoyl) amino, hexanoylamino, hepta Noylamino, (3,3-dimethylbutanoyl) amino, methoxycarbonylamino, ethoxycarbonylamino, propoxycarbonylamino, isopropoxycarbonylamino, butoxycarbonylamino, isobutoxycarbonyl Amino, s-butoxycarbonylamino, t-butoxycarbonylamino, pentoxycarbonylamino, isopentoxycarbonylamino, (2-methylbutoxycarbonyl) amino, neopentoxycarbonylamino, (1-ethylpropoxycarbonyl) amino, hexyl Oxycarbonylamino, (4-methylpentoxycarbonyl) amino, (3-methylpentoxycarbonyl) amino, (2-methylpentoxycarbonyl) amino, (1-methylpentoxycarbonyl) amino, (3,3-dimethyl) (Butoxycarbonyl) amino, (2,2-dimethylbutoxycarbonyl) amino, (1,1-dimethylbutoxycarbonyl) amino, (1,2-dimethylbutoxycarbonyl) amino, (1,3-dimethylbutoxycarbonyl) amino, ( 2,3-Dimethylbutoxycarbonyl) amino, (2-ethylbutoxycarbonyl) amino Dimethylcarbamoylamino, (methylethylcarbamoyl) amino, diethylcarbamoylamino, dipropylcarbamoylamino, dibutylcarbamoylamino, dihexylcarbamoylamino, methylsulfonylamino, ethylsulfonylamino, propylsulfonylamino, isopropylsulfonylamino, butylsulfonylamino, t- It is a butyl sulfonylamino, or hexyl sulfonylamino, preferably, identical or different one to two C ₁ -C ₃ alkyl group, or, C ₂ -C ₄ alkylcarbonyl group, C ₂ -C ₄ alkoxycarbonyl An amino group which may be substituted by a group, a di (C ₁ -C ₃ alkyl) carbamoyl group or a C ₁ -C ₃ alkylsulfonyl group, more preferably methylamino, ethylamino, dimethylamino, di Ethylamino, acetylamino, propionylamino, (2-methylpropanoyl) amino, (2,2-dimethylpropanoyl) amino, methoxycarbonylamino, ethoxycarbonylamino, dimethylcarbamoylamino, diethylcarbamoylamino, methylsulfonylamino or ethyl A sulfonylamino group.

In the present invention, the “C ₁ -C ₆ haloalkoxy group” is the above-mentioned “C ₁ -C ₆ alkoxy group” substituted with 1 to 5 of the above “halogen atoms”, for example, chloromethoxy , Dichloromethoxy, trichloromethoxy, 1-chloroethoxy, 2-chloroethoxy, 2,2,2-trichloroethoxy, 1-chloropropoxy, 3-chloropropoxy, 1-chlorobutoxy, 4-chlorobutoxy, fluoromethoxy, Difluoromethoxy, trifluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, fluorochloromethoxy, bromomethoxy, 1-bromoethoxy, 2-bromoethoxy or iodomethoxy Preferably the same or different selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom. A 1-3 C ₁ substituent is substituted -C ₃ alkoxy group, and more preferably, the same one to three, fluorine atom or a chlorine atom is located at C ₁ -C ₂ alkoxy group substituted Even more preferred is a fluoromethoxy, difluoromethoxy, trifluoromethoxy or 2,2,2-trichloroethoxy group, and particularly preferred is a trifluoromethoxy group.

In the present invention, the “substituted C ₃ -C ₆ cycloalkyl group (the substituent is a substituent selected from the substituent group C)” is the above-mentioned “halogen atom” and the above “substituted”. C ₁ -C ₆ alkyl group (the substituent is a substituent selected from Substituent Group B) ”, the“ C ₃ -C ₆ cycloalkyl group ”, and the“ C ₂ -C ₆ alkenyl group ”. , A cyano group, the “C ₂ -C ₇ alkylcarbonyl group”, a benzoyl group, a carboxyl group, the “C ₂ -C ₇ alkoxycarbonyl group”, a carbamoyl group, and the “di (C ₁ -C ₆ alkyl) carbamoyl group” ", Said" optionally substituted phenyl group (the substituent is a substituent selected from substituent group A) "," the 5- or 6-membered heterocyclic group (the heterocyclic ring is in the ring, Contains one nitrogen, oxygen or sulfur atom Furthermore, it may contain 1 to 2 nitrogen atoms.) ”,“ The amino group which may be substituted (the substituent is a substituent selected from substituent group D) ”, nitro group, hydroxyl group The “C ₁ -C ₆ alkoxy group”, the “C ₁ -C ₆ haloalkoxy group”, the phenoxy group, the “C ₁ -C ₆ alkylthio group”, the phenylthio group, the “C ₁ -C ₆ alkylsulfinyl” The “C ₃ -C ₆ cycloalkyl group” substituted by the same or different 1 to 5 substituents selected from the group consisting of “group” and the “C ₁ -C ₆ alkylsulfonyl group”, for example, , Fluorocyclopropyl, difluorocyclopropyl, chlorocyclopropyl, dichlorocyclopropyl, bromocyclopropyl, dibromocyclopropyl, iodocyclopropyl, methylcyclopropyl, Tylcyclopropyl, propylcyclopropyl, isopropylcyclopropyl, butylcyclopropyl, t-butylcyclopropyl, hexylcyclopropyl, cyclopropylcyclopropyl, cyclobutylcyclopropyl, cyclopentylcyclopropyl, (fluoromethyl) cyclopropyl, (chloromethyl) ) Cyclopropyl, (bromomethyl) cyclopropyl, (difluoromethyl) cyclopropyl, (trifluoromethyl) cyclopropyl, (trichloromethyl) cyclopropyl, (2,2,2-trifluoroethyl) cyclopropyl, (2,2 , 2-trichloroethyl) cyclopropyl, vinylcyclopropyl, (methoxymethyl) cyclopropyl, (ethoxymethyl) cyclopropyl, (isopropoxymethyl) cyclopropyl, (methylthiomethyl) cyclopropyl, (ethylthiomethyl) ) Cyclopropyl, (isopropylthiomethyl) cyclopropyl, (methylsulfinylmethyl) cyclopropyl, (ethylsulfinylmethyl) cyclopropyl, (methylsulfonylmethyl) cyclopropyl, (ethylsulfonylmethyl) cyclopropyl, cyanocyclopropyl, 1-methoxyiminoethyl) cyclopropyl, acetylcyclopropyl, propionylcyclopropyl, benzoylcyclopropyl, carboxylcyclopropyl, methoxycarbonylcyclopropyl, ethoxycarbonylcyclopropyl, carbamoylcyclopropyl, (dimethylcarbamoyl) cyclopropyl, (diethylcarbamoyl) Cyclopropyl, phenylcyclopropyl, (fluorophenyl) cyclopropyl, (chlorophenyl) cyclopropyl, tolylcyclopropyl , Furylcyclopropyl, thienylcyclopropyl, pyridylcyclopropyl, aminocyclopropyl, (methylamino) cyclopropyl, (dimethylamino) cyclopropyl, (acetylamino) cyclopropyl, (methoxycarbonylamino) cyclopropyl, (3,3 -Dimethylureido) cyclopropyl, (methylsulfonylamino) cyclopropyl, nitrocyclopropyl, hydroxycyclopropyl, methoxycyclopropyl, ethoxycyclopropyl, (trifluoromethoxy) cyclopropyl, phenoxycyclopropyl, methylthiocyclopropyl, ethylthiocyclo Propyl, phenylthiocyclopropyl, methylsulfinylcyclopropyl, ethylsulfinylcyclopropyl, methylsulfonylcyclopropyl, ethylsulfonylcyclopropyl Pill, dimethylcyclopropyl, methyl (ethyl) cyclopropyl, diethylcyclopropyl, biscyanocyclopropyl, trimethylcyclopropyl, tetramethylcyclopropyl, pentamethylcyclopropyl, methylcyclobutyl, vinylcyclobutyl, cyanocyclobutyl, carboxylcyclo butyl, acetyl cyclobutyl, be a methoxycarbonyl cyclobutyl or aminocyclobutyl group, preferably a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₃ -C ₄ cycloalkyl group and cyano The same or different 1 to 5 substituents selected from the group consisting of a group, or “the same or different 1 to 3 substituents selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom are substituted; C ₁ -C ₃ alkyl group and, or, C ₃ -C ₄ consequent Alkyl group, cyano group, C ₂ -C ₄ alkylcarbonyl group, C ₂ -C ₄ alkoxycarbonyl group, a phenyl group, C ₁ -C ₃ alkoxy groups, C ₁ -C ₃ alkylthio group, C ₁ -C ₃ alkylsulfinyl group, C ₁ -C ₃ alkylsulfonyl groups, C ₁ -C ₂ alkylenedioxy group, C ₁ -C ₃ alkyl group imino group or a C ₁ -C ₃ alkoxyimino group is substituted ", C ₂ -C ₄ alkenyl group, C ₂ -C ₄ alkylcarbonyl group, a benzoyl group, a carboxyl group, C ₂ -C ₄ alkoxycarbonyl group, a carbamoyl group, a di (C ₁ -C ₃ alkyl) carbamoyl group, "a fluorine atom, a chlorine atom, a bromine atom , C ₁ -C ₃ alkyl group, "a fluorine atom, C ₁ -C ₃ alkyl 1-3 substituents the same or different selected from the group consisting of chlorine atom and bromine atom is substituted ", C ₃ -C ₄ cycloalkyl group, a cyano group and a tri (C ₁ -C ₃ alkyl) same or different 1 to 3 substituents may phenyl group substituted selected from the group consisting of silicon group" 5-membered heterocyclic group (the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring). ), “One or two identical or different C ₁ -C ₃ alkyl groups, or C ₂ -C ₄ alkylcarbonyl groups, C ₂ -C ₄ alkoxycarbonyl groups, di (C ₁ -C ₃ alkyl) carbamoyl group or C ₁ -C ₃ alkylsulfonyl amino group which may be substituted by a group ", a nitro group, a hydroxyl group, C ₁ -C ₃ alkoxy groups, C ₁ -C ₃ haloalkoxy group, a phenoxy group, C ₁ -C ₃ alkylthio group, a phenylthio group, C ₁ -C ₃ alkyl sulfinyl group or a C ₁ -C ₃ alkylsulfonyl group C ₃ -C ₄ cycloalkyl group substituted by, more preferably, a chlorine atom, a bromine atom, C ₁ -C ₂ alkyl group, the same or different 1 to 3 substituents selected from the group consisting of cyclopropyl group and cyano group, or the same selected from the group consisting of "a chlorine atom and a bromine atom 1-3 substituents is substituted with C ₁ -C ₂ alkyl group, or a cyclopropyl group, a cyano group, C ₂ -C ₃ alkylcarbonyl group, C ₂ -C ₃ alkoxycarbonyl group, a phenyl group, C ₁ -C ₂ alkoxy group, C ₁ -C ₂ alkylthio group, C ₁ -C ₂ alkylsulfinyl group, C ₁ -C ₂ alkylsulfonyl group, 1,2-ethylenedioxy group, an imino group or a C ₁ -C ₂ alkoxy C ₁ -C ₂ alkyl group "imino group is substituted, C ₂ -C ₃ alkenyl group, C ₂ -C ₃ alkylcarbonyl group, a benzoyl group, a carboxyl group, C ₂ -C ₃ alkoxycarbonyl group, a carbamoyl group, a di (C ₁ -C ₂ alkyl) carbamoyl group, “chlorine atom, bromine atom, C ₁ -C ₂ alkyl group,“ the same 1 to 3 C ₁ -C ₂ alkyl group substituted by fluorine atom or chlorine atom " Ropuropiru group, a cyano group and a tri (C ₁ -C ₂ alkyl) same or different 1 to 2 substituents may phenyl group substituted selected from the group consisting of silicon group ", a furyl group, a thienyl group," identical 1-2 C ₁ -C ₂ alkyl group, or, C ₂ -C ₃ alkylcarbonyl group, C ₂ -C ₃ alkoxycarbonyl group, a di (C ₁ -C ₂ alkyl) carbamoyl group or a C ₁ ~ C ₂ alkylsulfonyl amino group which may be substituted by a group ", a nitro group, a hydroxyl group, C ₁ -C ₂ alkoxy group, C ₁ -C ₂ haloalkoxy group, a phenoxy group, C ₁ -C ₂ alkylthio group, a phenylthio group, It is a cyclopropyl group substituted by a C ₁ -C ₂ alkylsulfinyl group or a C ₁ -C ₂ alkylsulfonyl group.

In the present invention, the “C ₄ -C ₁₀ bicycloalkyl group” is a bicyclic hydrocarbon having 4 to 10 carbon atoms, such as bicyclobutyl, bicyclopentyl, bicyclohexyl, bicycloheptyl, bicyclooctyl, bicyclononyl. Or a bicyclodecyl group, preferably a bicyclohexyl or bicycloheptyl group, more preferably a bicyclo [3.1.0] hexyl or bicyclo [4.1.0] heptyl group, and even more preferably. , A bicyclo [3.1.0] hexane-6-yl group.

In the present invention, “optionally substituted phenylsulfonyl group (the substituent is a substituent selected from Substituent Group A)” means the “halogen atom” and the “C ₁ -C ₆ alkyl group”. , The same or different selected from the group consisting of the “C ₁ -C ₆ haloalkyl group”, the “C ₃ -C ₆ cycloalkyl group”, the cyano group and the “tri (C ₁ -C ₆ alkyl) silicon group” 1 to 5 substituents which may be substituted, such as phenylsulfonyl, fluorophenylsulfonyl, difluorophenylsulfonyl, trifluorophenylsulfonyl, chlorophenylsulfonyl, dichlorophenylsulfonyl, trichlorophenylsulfonyl, fluorochlorophenylsulfonyl , Methylphenylsulfonyl, dimethylphenylsulfo , Trimethylphenylsulfonyl, tetramethylphenylsulfonyl, pentamethylphenylsulfonyl, ethylphenylsulfonyl, fluoro (methyl) phenylsulfonyl, chloro (methyl) phenylsulfonyl, bromo (methyl) phenylsulfonyl, cyclopropylphenylsulfonyl, cyclopropyl (fluoro ) Phenylsulfonyl, chloro (cyclopropyl) phenylsulfonyl, cyclopropyl (methyl) phenylsulfonyl, (trifluoromethyl) phenylsulfonyl or fluoro (trifluoromethyl) phenylsulfonyl group, preferably fluorine atom, chlorine atom , bromine atom, C ₁ -C ₃ alkyl group, "a fluorine atom, C ₁ -C ₃ alkyl group one to three substituents the same or different selected from the group consisting of chlorine atom and bromine atom is substituted In C ₃ -C ₄ cycloalkyl group, a cyano group and a tri (C ₁ -C ₃ alkyl) identical are selected from the group consisting of silicon group or different 1 to 3 substituents are substituted to it phenylsulfonyl group And more preferably a phenylsulfonyl, chlorophenylsulfonyl, methylphenylsulfonyl, trifluorophenylsulfonyl or cyanophenylsulfonyl group.

In the present invention, the “di (C ₁ -C ₆ alkyl) sulfamoyl group” is a sulfamoyl group in which two identical or different “C ₁ -C ₆ alkyl groups” are bonded to a nitrogen atom. It may be sulfamoyl, methylethylsulfamoyl, diethylsulfamoyl, dipropylsulfamoyl, dibutylsulfamoyl or dihexylsulfamoyl, preferably two identical or different C ₁ -C ₃ alkyls A sulfamoyl group to which a group is bonded, more preferably a dimethylsulfamoyl group or a diethylsulfamoyl group, and even more preferably a dimethylsulfamoyl group.

In the present invention, “a 3- to 6-membered heterocyclic group which may be substituted (the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and further 1 to 2 nitrogen atoms And may be condensed with a benzene ring. The substituent is a substituent selected from Substituent Group E.) ”is the“ halogen atom ”and the“ C ₁ -C ₆ alkyl group ”. And ₁ to 3 identical or different substituents selected from the group consisting of “C ₁ -C ₆ haloalkyl group”, or a hydroxyl group, the above “optionally substituted phenylsulfonyl group (the substituent is substituted Is a substituent selected from the group A.) ”or“ the di (C ₁ -C ₆ alkyl) sulfamoyl group ”, and may be condensed with a benzene ring, Contains nitrogen, oxygen or sulfur atoms, and It may contain ~ 2 nitrogen atoms, a 3- to 6-membered heterocyclic group ", preferably a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group and" a fluorine atom, a chlorine atom And the same or different 1 to 2 substituents selected from the group consisting of a C ₁ -C ₃ alkyl group substituted with 1 to 3 same or different substituents selected from the group consisting of bromine atoms, Or, a hydroxyl group, “a fluorine atom, a chlorine atom, a bromine atom, a C ₁ -C ₃ alkyl group,“ the same or different 1 to 3 substituents selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom. ₁ to ₃ identical or different substitutions selected from the group consisting of “substituted C ₁ -C ₃ alkyl group”, C ₃ -C ₄ cycloalkyl group, cyano group and tri (C ₁ -C ₃ alkyl) silicon group A phenylsulfonyl group which may be substituted ”or Or different well two C ₁ -C ₃ sulfamoyl group which the alkyl group is attached "of substituted benzene ring fused may, as" heteroatom, one nitrogen atom, an oxygen atom or a sulfur atom A 3- to 6-membered heterocyclic group which may further contain one nitrogen atom, and more preferably a chlorine atom, a bromine atom, a methyl group, an ethyl group, and a trifluoromethyl group. The same 1 to 2 substituents selected from the group, or a hydroxyl group, phenylsulfonyl group, tolylsulfonyl group or dimethylsulfamoyl group, which may be substituted, aziridine, oxiranyl, oxetanyl, pyrrolyl, furyl, thienyl, pyrazolyl , Thiazolyl, pyridyl, benzimidazolyl or benzothiazolyl, and even more preferably from a chlorine atom, a methyl group and a trifluoromethyl group That the same or different 1 to 2 substituents may be substituted, thienyl, pyrazolyl, thiazolyl group.

In the present invention, “(C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkoxy group” is an alkoxy group having 1 to 6 carbon atoms to which an alkoxy group having 1 to 6 carbon atoms is bonded. Methoxy, ethoxymethoxy, propoxymethoxy, butoxymethoxy, s-butoxymethoxy, t-butoxymethoxy, pentyloxymethoxy, hexyloxymethoxy, methoxyethoxy, ethoxyethoxy, propoxyethoxy, butoxyethoxy, methoxypropoxy, methoxybutoxy, methoxypentyloxy Or a methoxyhexyloxy group, preferably an alkoxy group having 1 to 3 carbon atoms substituted by an alkoxy group having 1 to 3 carbon atoms, more preferably methoxyethoxy, ethoxyethoxy or ethoxymethoxy. It is a group.

In the present invention, “an optionally substituted phenoxy group (the substituent is a pyridazinyloxy group substituted by a hydroxyl group or a substituent selected from a halogen atom and a C ₁ -C ₆ alkoxy group)” Is a phenoxy group that may be substituted by one hydroxyl group, or ₁ to 3 identical or different substituents selected from the group consisting of the “halogen atom” and the “C ₁ -C ₆ alkoxy group”. phenoxy group substituted pyridazinyloxy group is substituted, preferably, hydroxy phenoxy group, or a fluorine atom, a chlorine atom, the same are selected from the group consisting of bromine and C ₁ -C ₃ alkoxy or It is a phenoxy group substituted by a pyridazinyloxy group substituted with 1 to 2 different substituents, and more preferably one chlorine atom and one methoxy or ethoxy group. Substituted pyridazinyloxy group is a phenoxy group substituted.

In the present invention, “a 5- to 6-membered heterocyclic oxy group which may be substituted (the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and 1 to 2 nitrogen atoms). The substituent may be a substituent selected from Substituent Group E. The above-mentioned “halogen atom”, “C ₁ -C ₆ alkyl group”, and “C ₁ -C” ₆ haloalkyl group ”, hydroxyl group, the above“ optionally substituted phenylsulfonyl group (the substituent is a substituent selected from substituent group A) ”and the“ di (C ₁ -C ₆ alkyl) sulfamoyl group ”. May be substituted by the same or different 1 to 2 substituents selected from the group consisting of “a hetero atom containing one nitrogen atom, oxygen atom or sulfur atom, and further 1 to 2 A 5-6 membered heterocyclic oxy group which may contain a nitrogen atom. Preferably, fluorine atom, chlorine atom, bromine atom, C ₁ -C ₃ alkyl group, "a fluorine atom, one to three substituents the same or different from selected from the group consisting of chlorine and bromine substituted C ₁ -C ₃ alkyl group ", a hydroxyl group," a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, "a fluorine atom, the same or different selected from the group consisting of chlorine and bromine identical to 1 to 3 substituents are selected from the group consisting of C ₁ -C ₃ alkyl group ", C ₃ -C ₄ cycloalkyl group, a cyano group and a tri (C ₁ -C ₃ alkyl) silyl group substituted with Or the same or different selected from the group consisting of “phenylsulfonyl group which may be substituted by 1 to 3 different substituents” and “sulfamoyl group to which two same or different C _{1 to} C ₃ alkyl groups are bonded”. 1 to 2 substituents A 5- to 6-membered heterocyclic oxy group which contains one nitrogen atom, oxygen atom or sulfur atom and may further contain one nitrogen atom as a hetero atom, which may be substituted; More preferably, 1 to 2 different groups selected from the group consisting of a chlorine atom, a bromine atom, a methyl group, an ethyl group, a trifluoromethyl group, a hydroxyl group, a phenylsulfonyl group, a tolylsulfonyl group, and a dimethylsulfamoyl group. The substituent may be a pyridyloxy, pyrrolyloxy, furyloxy, thienyloxy, pyrazolyloxy, thiazolyloxy, pyrimidyloxy, pyrazinyloxy or pyridazinyloxy group, and more preferably a chlorine atom and a hydroxyl group are substituted. A good pyridazinyloxy group.

In the present invention, “an optionally substituted phenylsulfonyloxy group (the substituent is a substituent selected from Substituent Group A)” refers to the “halogen atom” and the “C ₁ -C ₆ alkyl group”. ”, The“ C ₁ -C ₆ haloalkyl group ”, the“ C ₃ -C ₆ cycloalkyl group ”, the cyano group, and the“ tri (C ₁ -C ₆ alkyl) silicon group ” 1 to 5 different substituents are phenylsulfonyloxy groups which may be substituted, such as phenylsulfonyloxy, fluorophenylsulfonyloxy, difluorophenylsulfonyloxy, trifluorophenylsulfonyloxy, chlorophenylsulfonyloxy, dichlorophenylsulfonyloxy , Trichlorophenylsulfonyloxy, fluorochlorophenylsulfo Ruoxy, methylphenylsulfonyloxy, dimethylphenylsulfonyloxy, trimethylphenylsulfonyloxy, tetramethylphenylsulfonyloxy, pentamethylphenylsulfonyloxy, ethylphenylsulfonyloxy, fluoro (methyl) phenylsulfonyloxy, chloro (methyl) phenylsulfonyloxy, Bromo (methyl) phenylsulfonyloxy, cyclopropylphenylsulfonyloxy, cyclopropyl (fluoro) phenylsulfonyloxy, chloro (cyclopropyl) phenylsulfonyloxy, cyclopropyl (methyl) phenylsulfonyloxy, (trifluoromethyl) phenylsulfonyloxy or It may be a fluoro (trifluoromethyl) phenylsulfonyloxy group, preferably a fluorine atom, a chlorine atom Bromine, C ₁ -C ₃ alkyl group, "a fluorine atom, C ₁ -C ₃ alkyl group one to three substituents the same or different selected from the group consisting of a chlorine atom and a bromine atom-substituted" in C ₃ -C ₄ cycloalkyl group, a cyano group and a tri (C ₁ -C ₃ alkyl) identical are selected from the group consisting of silicon group or different 1 to 3 substituents are substituted to be phenyl sulfonyloxy group And more preferably a phenylsulfonyloxy, chlorophenylsulfonyloxy, methylphenylsulfonyloxy, trifluorophenylsulfonyloxy or cyanophenylsulfonyloxy group.

In R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ of the present invention, “the two adjacent groups may be formed together with the carbon atom to which each is bonded, which may be substituted 3 to 6 members. A cyclic hydrocarbon group (the cyclic hydrocarbon may be interrupted by one or two different heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. The substituent is a halogen atom, C ₁ -C ₆ alkyl group, a hydroxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, an oxo group, a hydroxyimino group or a C ₁ -C ₆ alkoxyimino group, C ₁ -C ₆ alkyl group Is substituted with another C ₁ -C ₆ alkyl group or a carbon atom on the ring to form a new three-membered ring.) ”Means“ halogen atom ”,“ C _1- “C ₆ alkyl group”, the above “C substituted with 1-2 hydroxyl groups” ₁ -C ₆ alkyl group ", the" C ₁ -C ₆ alkoxy group ", an oxo group, hydroxyimino group, and the" C ₁ -C ₆ alkoxyimino same or different 1 to 4 selected from the group consisting of group " Saturated or unsaturated 3- to 6-membered rings which may be substituted by one or two heteroatoms which may be substituted and may be substituted by the same or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur atoms It is a hydrocarbon group and may form a cyclopropane ring on the ring, and is preferably --CH _2- , --CH ₂ CH _2- , --CH ₂ CH ₂ CH _2- , --CH (CH ₃ ). CH ₂ CH _2- , -CH ₂ CH (CH ₃ ) CH _2- , -C (CH ₃ ) ₂ CH ₂ CH _2- , -CH ₂ C (CH ₃ ) ₂ CH _2- , -CH (OCH ₃ ) CH ₂ CH _2- , -C (OCH ₃ ) ₂ CH ₂ CH _2- , -CH ₂ C (OCH ₃ ) ₂ CH _2- , -C (= O) CH ₂ CH _2- , -CH ₂ C (= O) CH _2- , -C (= NOCH ₃ ) CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ CH _2- , -CH (CH ₃ ) CH ₂ CH ₂ CH _2- , -C (CH ₃ ) ₂ CH ₂ CH ₂ CH _2- , -CH (OCH ₃ ) CH ₂ CH ₂ CH _2- , -C H = CH-CH = CH-, -OCH ₂ CH _2- , -OCH (CH ₃ ) CH _2- , -OCH ₂ CH (CH ₃ )-, -OC (CH ₃ ) ₂ CH _2- , -OCH = CH-, -OC (CH ₃ ) = CH-, -OCH = C (CH ₃ )-, -SCH = CH-, -N = CH-CH = CH-, -OCH ₂ O-, -OCH (CH ₃ ) O-, -OC (CH ₃ ) ₂ O-, -OCF ₂ O-, -OCH ₂ CH ₂ O-, -OCH = N-, -OC (CH ₃ ) = N-,

In a group represented by, more _{preferably, -CH 2 CH 2 -, -} CH 2 CH 2 CH 2 -, - CH (CH 3) CH 2 CH 2 -, - CH 2 CH 2 CH 2 CH 2 -, -CH = CH-CH = CH-, -OCH ₂ CH _2- , -OCH = CH-, -OCH = C (CH ₃ )-, -SCH = CH-, -N = CH-CH = CH- , -OCH ₂ O-, -OCH ₂ CH ₂ O-,

And more preferably, —CH ₂ CH ₂ CH ₂ —, —CH (CH ₃ ) CH ₂ CH ₂ —, —OCH ₂ CH ₂ —, —OCH═CH— or

It is group represented by these.

  The compound (I) of the present invention can be converted into a salt used in ordinary agricultural chemicals, for example, an alkali metal salt, an alkaline earth metal salt or an ammonium salt, and a basic moiety in the molecule. If there is, for example, a salt such as sulfate, hydrochloride, nitrate, phosphate can be formed. As long as they can be used as herbicides for agriculture and horticulture, they are included in the present invention.

  In the present invention, the “alkali metal salt” can be, for example, a sodium salt, a potassium salt or a lithium salt, and is preferably a sodium salt or a potassium salt.

  In the present invention, the “alkaline earth metal salt” can be, for example, a calcium salt or a magnesium salt, and is preferably a calcium salt.

  Solvates of the compounds of the present invention are also encompassed by the present invention.

  Some compounds of the present invention have an asymmetric carbon, and in this case, the present invention also includes a mixture of one kind of optically active substance and several kinds of optically active substances in an arbitrary ratio.

In the present invention, the “ester derivative” is a compound in which an acyl group or the like is bonded to the oxygen atom of the hydroxyl group bonded to the 4-position of the pyridazine ring. For example, the C _{2 to} C ₁₅ alkylcarbonyl group [substituent group, halogen atom, C ₁ -C ₆ alkoxy group, C ₂ -C ₇ alkoxycarbonyl group, may be substituted C ₂ -C ₆ alkenyloxycarbonyl group {said substituent group is C ₃ -C ₆ cycloalkyl group , a cyano group and which may be substituted benzoyl group (the substituent is a halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₃ haloalkyl group, C ₂ -C ₇ alkoxycarbonyl group, a nitro group and a C ₁ ~ The same or different 1 to 3 substituents selected from the group consisting of C ₃ alkylsulfonyl groups.) The same or different 1 to 3 substituents selected from the group consisting of . }, An optionally substituted C ₃ -C ₆ cycloalkenyloxycarbonyl group {the substituent is an oxo group and an optionally substituted benzoyl group (the substituent is a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ A group consisting of ₁ to ₃ identical or different substituents selected from the group consisting of a -C ₃ haloalkyl group, a C ₂ -C ₇ alkoxycarbonyl group, a nitro group and a C ₁ -C ₃ alkylsulfonyl group. 1 to 2 substituents selected from the same or different. }, A 5- or 6-membered heterocyclic oxycarbonyl group which may be substituted {the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and further 1 to 2 nitrogen atoms May be included. The substituent is a halogen atom, a C ₁ -C ₆ alkyl group, an optionally substituted phenoxy group (the substituent is a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₃ haloalkyl group, a C _3- The same or different 1 to 3 substituents selected from the group consisting of a C ₆ cycloalkyl group and a C _{2 to} C ₇ alkoxycarbonyl group.), 2,3-dihydro-1H-indenyloxy group and substitution which may be a benzoyl group (the substituent is to be a halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₃ haloalkyl group, C ₂ -C ₇ alkoxycarbonyl group, a nitro group and a C ₁ -C ₃ alkylsulfonyl group The same or different 1 to 3 substituents selected from the group consisting of: 1) to 3 or the same or different 1 to 3 substituents selected from the group consisting of: }, Which may be substituted phenyl group (said substituent is a halogen atom, C ₁ -C ₆ alkyl group, a C ₁ -C ₃ haloalkyl group, C ₁ -C ₆ alkoxy group and C ₂ -C ₇ alkoxycarbonyl group Or the same or different 1 to 3 substituents selected from the group consisting of phenoxy group and C _{1 to} C ₆ alkylthio group. . ], C ₄ -C ₇ cycloalkylcarbonyl group, adamantyl group may be substituted C ₃ -C ₇ alkenylcarbonyl group (the substituent has the same or different selected from the group consisting of a halogen atom and a phenyl group 1 ˜2 substituents), a C ₃ -C ₇ alkynylcarbonyl group, an optionally substituted benzoyl group [the substituent is a halogen atom, an optionally substituted C ₁ -C ₆ alkyl group (the substituent Are the same or different 1 to 3 substituents selected from the group consisting of a halogen atom and a phenyl group.), A cyano group, a C ₂ -C ₇ alkylcarbonyl group, a C ₂ -C ₇ alkoxycarbonyl group, An optionally substituted C ₃ -C ₇ alkenyloxycarbonyl group {the substituent is a C ₃ -C ₆ cycloalkyl group, a cyano group and an optionally substituted benzoyl group (the Same substituent is selected from halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₃ haloalkyl group, C ₂ -C ₇ alkoxycarbonyl group, a nitro group and a C ₁ -C ₃ group consisting of an alkylsulfonyl group Or 1 to 3 different substituents selected from the group consisting of 1 to 3 different substituents. }, An optionally substituted C ₄ -C ₇ cycloalkenyloxycarbonyl group {the substituent is an oxo group and an optionally substituted benzoyl group (the substituent is a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ A group consisting of ₁ to ₃ identical or different substituents selected from the group consisting of a -C ₃ haloalkyl group, a C ₂ -C ₇ alkoxycarbonyl group, a nitro group and a C ₁ -C ₃ alkylsulfonyl group. 1 to 2 substituents selected from the same or different. }, A phenyl group, a nitro group, an optionally substituted C ₁ -C ₆ alkoxy group (the substituent is the same or different 1 to 3 substituents selected from the group consisting of a halogen atom and a phenyl group. ), A phenoxy group, an optionally substituted 5- or 6-membered heterocyclic oxycarbonyl group {the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring; It may contain nitrogen atoms. The substituent is a halogen atom, a C ₁ -C ₆ alkyl group, an optionally substituted phenoxy group (the substituent is a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₃ haloalkyl group, a C _3- The same or different 1 to 3 substituents selected from the group consisting of a C ₆ cycloalkyl group and a C _{2 to} C ₇ alkoxycarbonyl group.), 2,3-dihydro-1H-indenyloxy group and substitution which may be a benzoyl group (the substituent is to be a halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₃ haloalkyl group, C ₂ -C ₇ alkoxycarbonyl group, a nitro group and a C ₁ -C ₃ alkylsulfonyl group The same or different 1 to 3 substituents selected from the group consisting of: 1) to 3 or the same or different 1 to 3 substituents selected from the group consisting of: } And a 5- or 6-membered heterocyclic oxysulfonyl group which may be substituted {the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and further 1 to 2 nitrogen atoms May be included. The substituent is a halogen atom, a C ₁ -C ₆ alkyl group, an optionally substituted phenoxy group (the substituent is a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₃ haloalkyl group, a C _3- The same or different 1 to 3 substituents selected from the group consisting of a C ₆ cycloalkyl group and a C _{2 to} C ₇ alkoxycarbonyl group.), 2,3-dihydro-1H-indenyloxy group and substitution which may be a benzoyl group (the substituent is to be a halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₃ haloalkyl group, C ₂ -C ₇ alkoxycarbonyl group, a nitro group and a C ₁ -C ₃ alkylsulfonyl group The same or different 1 to 3 substituents selected from the group consisting of: 1) to 3 or the same or different 1 to 3 substituents selected from the group consisting of: } Are the same or different 1 to 3 substituents selected from the group consisting of: ], A naphthoyl group, an optionally substituted 3- to 8-membered heterocyclic carbonyl group [the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and further 1 to 2 nitrogen atoms It may contain atoms and may form a 5- to 6-membered spiro ring containing 1-2 oxygen atoms on any carbon atom in the heterocycle. The substituent is a halogen atom and an optionally substituted C ₁ -C ₆ alkyl group (the substituent is the same or different 1 to 3 substituents selected from the group consisting of a halogen atom and a phenyl group. ), A cyano group, a C ₂ -C ₇ alkylcarbonyl group, a C ₂ -C ₇ alkoxycarbonyl group, an optionally substituted phenyl group (the substituent is the same or different 1 to 3 halogen atoms). A 5- or 6-membered heterocyclic group which may be substituted (the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom, and further contains 1 to 2 nitrogen atoms in the ring) The substituent is the same or different 1 to 3 substituents selected from the group consisting of a halogen atom and a C ₁ -C ₆ alkyl group.), Nitro group, hydroxyl group, C ₁ -C ₆ alkoxy Group, phenoxy group, oxo group, hydroxy Imino group, C ₁ -C ₆ alkoxyimino group, C ₁ -C ₆ alkylthio group, C ₂ -C ₆ alkenylthio group, a phenylthio group, which may be substituted 5 or 6-membered heterocyclic carbonyl group (said heterocyclic is in the ring, the one, nitrogen atom, contains an oxygen atom or a sulfur atom, may further contain one or two nitrogen atoms. the substituent is a halogen atom and a C ₁ -C ₆ alkyl group The same or different 1 to 3 substituents selected from the group consisting of: and a 5- or 6-membered heterocyclic oxycarbonyl group which may be substituted {the heterocyclic ring is one nitrogen atom in the ring; It contains atoms, oxygen atoms or sulfur atoms, and may contain 1 to 2 nitrogen atoms. The substituent is a halogen atom, a C ₁ -C ₆ alkyl group, an optionally substituted phenoxy group (the substituent is a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₃ haloalkyl group, a C _3- C ₆ is the same or different 1 to 3 substituents selected from cycloalkyl group and C ₂ -C ₇ alkoxyalkyl group consisting carbonyl group.), 2,3-dihydro -1H- indenyl group and a substituted which may be a benzoyl group (the substituent is to be a halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₃ haloalkyl group, C ₂ -C ₇ alkoxycarbonyl group, a nitro group and a C ₁ -C ₃ alkylsulfonyl group The same or different 1 to 3 substituents selected from the group consisting of: 1) to 3 or the same or different 1 to 3 substituents selected from the group consisting of: } Are the same or different 1 to 3 substituents selected from the group consisting of: An optionally substituted 7 to 14-membered fused bi- or tricyclic heterocyclic carbonyl group (the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring; may contain two nitrogen atoms or oxygen atoms. the substituents are the same or different 1 to 3 substituents selected from the group consisting of halogen atom and C ₁ -C ₆ alkyl group.) 5- or 6-membered heterocyclic carbonylcarbonyl group (the heterocyclic ring may contain one nitrogen atom, oxygen atom or sulfur atom in the ring, and may further contain 1 to 2 nitrogen atoms). ) may be substituted C ₂ -C ₇ alkoxycarbonyl group (said substituent is a halogen atom, C ₁ -C ₆ same or different 1 to 3 substituents selected from the alkoxy group and the group consisting of phenyl group in a.), C ₃ ~C ₇ alkenyloxycarbonyl , Which may be substituted phenoxycarbonyl group (said substituent is a halogen atom, C ₁ -C ₆ alkyl group, a cyano group, C ₂ -C ₇ alkylcarbonyl group, C ₂ -C ₇ alkoxycarbonyl group, a nitro group and a C ₁ are the same or different 1 to 3 substituents selected from the group consisting of -C ₆ alkoxy group.

), A condensed polycyclic hydrocarbon oxycarbonyl group, an optionally substituted 5- or 6-membered heterocyclic oxycarbonyl group {the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring. Further, it may contain 1 to 2 nitrogen atoms. The substituent is a halogen atom, a C ₁ -C ₆ alkyl group, an optionally substituted phenoxy group (the substituent is a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₃ haloalkyl group, a C _3- The same or different 1 to 3 substituents selected from the group consisting of a C ₆ cycloalkyl group and a C _{2 to} C ₇ alkoxycarbonyl group.), 2,3-dihydro-1H-indenyloxy group and substitution which may be a benzoyl group (the substituent is to be a halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₃ haloalkyl group, C ₂ -C ₇ alkoxycarbonyl group, a nitro group and a C ₁ -C ₃ alkylsulfonyl group The same or different 1 to 3 substituents selected from the group consisting of: 1) to 3 or the same or different 1 to 3 substituents selected from the group consisting of: }, Which may be substituted carbamoyl group {said substituents may be substituted C ₁ -C ₆ alkyl group (said substituent is a halogen atom, C ₂ -C ₇ alkoxycarbonyl group, a cyano group, a phenyl group, and C ₁ to 3 substituents selected from the group consisting of _{1 to} C ₆ alkoxy groups), C _{3 to} C ₆ alkenyl groups, phenyl groups, optionally substituted 5 or 6 membered heterocyclic groups. (The heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and may further contain 1 to 2 nitrogen atoms. The substituent includes a halogen atom and C _1. -C ₆ identical or different 1 to 3 substituents selected from the group consisting of alkyl group.), C ₂ ~C ₇ alkylcarbonyl group, C ₂ -C ₇ alkoxycarbonyl group and C ₁ -C ₆ The same or selected from the group consisting of alkoxy groups 1 to 3 different substituents. }, (C ₁ -C ₆ alkylthio) carbonyl group, (C ₃ -C ₆ cycloalkylthio) carbonyl group, (phenylthio) carbonyl group, optionally substituted C ₁ -C ₈ alkylsulfonyl group (the substituents are the same) or different 1 to 3 halogen atoms.), which may be substituted phenylsulfonyl group [the substituent is a halogen atom, C ₁ -C ₆ alkyl group, a cyano group, C ₂ -C ₇ alkylcarbonyl group , C ₂ -C ₇ alkoxycarbonyl group, nitro group, C ₁ -C ₆ alkoxy group, may be substituted C ₂ -C ₆ alkenyloxy sulfonyl group {said substituents, C ₃ -C ₆ cycloalkyl group, a cyano group and which may be substituted benzoyl group (the substituent is a halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₃ haloalkyl group, C ₂ -C ₇ alkoxycarbonyl group, two B are the same or different 1 to 3 substituents selected from the group, and C ₁ -C ₃ group consisting of an alkylsulfonyl group.) The same or selected from the group consisting of different with 1-3 substituents is there. }, An optionally substituted C ₃ -C ₆ cycloalkenyloxysulfonyl group {the substituent is an oxo group and an optionally substituted benzoyl group (the substituent is a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ A group consisting of ₁ to ₃ identical or different substituents selected from the group consisting of a -C ₃ haloalkyl group, a C ₂ -C ₇ alkoxycarbonyl group, a nitro group and a C ₁ -C ₃ alkylsulfonyl group. 1 to 2 substituents selected from the same or different. } And a 5- or 6-membered heterocyclic oxysulfonyl group which may be substituted {the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and further 1 to 2 nitrogen atoms May be included. The substituent is a halogen atom, a C ₁ -C ₆ alkyl group, an optionally substituted phenoxy group (the substituent is a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₃ haloalkyl group, a C _3- The same or different 1 to 3 substituents selected from the group consisting of a C ₆ cycloalkyl group and a C _{2 to} C ₇ alkoxycarbonyl group.), 2,3-dihydro-1H-indenyloxy group and substitution which may be a benzoyl group (the substituent is to be a halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₃ haloalkyl group, C ₂ -C ₇ alkoxycarbonyl group, a nitro group and a C ₁ -C ₃ alkylsulfonyl group The same or different 1 to 3 substituents selected from the group consisting of: 1) to 3 or the same or different 1 to 3 substituents selected from the group consisting of: } Are the same or different 1 to 3 substituents selected from the group consisting of: An optionally substituted 5- or 6-membered heterocyclic sulfonyl group (the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and further contains 1 to 2 nitrogen atoms) The substituent is the same or different 1 to 3 substituents selected from the group consisting of a halogen atom and a C _{1 to} C ₆ alkyl group. Ring oxysulfonyl group {The heterocyclic ring may contain one nitrogen atom, oxygen atom or sulfur atom in the ring, and may further contain 1 to 2 nitrogen atoms. The substituents are halogen atom, C ₁ -C ₆ alkyl group, which may be substituted phenoxy group (the substituent is halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₃ haloalkyl group, C ₃ ~ The same or different 1 to 3 substituents selected from the group consisting of a C ₆ cycloalkyl group and a C _{2 to} C ₇ alkoxycarbonyl group.), 2,3-dihydro-1H-indenyloxy group and substitution which may be a benzoyl group (the substituent is to be a halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₃ haloalkyl group, C ₂ -C ₇ alkoxycarbonyl group, a nitro group and a C ₁ -C ₃ alkylsulfonyl group The same or different 1 to 3 substituents selected from the group consisting of: 1) to 3 or the same or different 1 to 3 substituents selected from the group consisting of: }, Di (C ₁ -C ₆ alkyl) sulfamoyl group, C ₁ -C ₆ alkoxysulfonyl group, di (C ₁ -C ₆ alkyl) phosphoryl group, tri (C ₁ -C ₆ alkyl) silicon group or triphenyl silicon give a compound group is bonded, preferably, C ₂ -C ₁₀ alkylcarbonyl group, which may be substituted benzoyl group (the substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group ₁ to 2 identical or different selected from the group consisting of C ₁ -C ₃ alkoxy group or 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yloxycarbonyl group is a substituent.), pyrrolidinylcarbonyl group, azetidinyloxyimino carbonyl group, morpholine group, may be substituted C ₂ -C ₅ alkoxycarbonyl group (said substituent is a fluorine atom, a chlorine atom and a bromine source The same or different 1 to 3 substituents selected from the group consisting of children), di (C ₁ -C ₃ alkyl) carbamoyl group, (C ₁ -C ₃ alkyl) (C ₁ -C ₃ alkoxy) ) carbamoyl group may be substituted C ₁ -C ₃ alkylsulfonyl group (the substituent is a fluorine atom, the same or different 1 to 3 substituents selected from the group consisting of chlorine and bromine. ) or substituted or a phenylsulfonyl group (the substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, 4- (2,4-dichlorobenzoyl) -1,3-dimethyl -1H -. pyrazol-5-yl oxy sulfonyl same or different 1 to 2 substituents selected from the group the group consisting of a nitro group) is a compound is bound, more preferably, C ₂ -C ₄ Alkylcarbonyl group, optionally substituted ben Yl group (the substituent is a methyl group or 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yloxycarbonyl group), 1-azetidinylcarbonyl group , 4-morpholinylcarbonyl group, may be substituted C ₂ -C ₃ alkoxycarbonyl group (said substituent is 1 to 3 chlorine atoms.), dimethylcarbamoyl group, methoxy (methyl) carbamoyl group, may be substituted C ₁ -C ₃ alkylsulfonyl group (said substituent is 1 to 3 fluorine atoms.) or which may be substituted phenylsulfonyl group (the substituent is a chlorine atom, a methyl group, 4 -(2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yloxysulfonyl group or nitro group. ) Is a bonded compound.

(A) In the present invention, R ¹ is preferably a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a C ₁ -C ₃ alkyl group, a C ₁ -C ₃ haloalkyl group (the halogen atom is 1 to 3 fluorine atoms)), cyclopropyl group, C ₂ -C ₃ alkenyl group, cyano group, C ₂ -C ₄ alkylcarbonyl group, di (C ₁ -C ₃ alkyl) carbamoyl group, may be substituted Phenyl group {the substituent is a fluorine atom, a chlorine atom, a bromine atom, a C ₁ -C ₃ alkyl group, a C ₁ -C ₃ haloalkyl group (the halogen atom is a group consisting of a fluorine atom, a chlorine atom and a bromine atom) The same or different 1 to 3 halogen atoms selected), the same or different 1 to 2 selected from the group consisting of a cyclopropyl group, a cyano group and a tri (C ₁ -C ₃ alkyl) silicon group. Substituents The }, A furyl group, a thienyl group, C ₁ -C ₃ alkoxy group, which may be substituted phenoxy group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ A haloalkyl group (the halogen atom is 1 to 3 fluorine atoms), a cyclopropyl group, a cyano group, and a tri (C ₁ -C ₃ alkyl) silicon group selected from the same or different 1 Two substituents. } Or a substituted pyrazolyloxy group (the substituent is one benzoyl group and two C ₁ -C ₃ alkyl groups substituted by two chlorine atoms),
More preferably, a chlorine atom, a bromine atom, a trifluoromethyl group or a cyano group,
Even more preferably, a chlorine atom or a bromine atom,
Particularly preferred is a chlorine atom.

(B) In the present invention, R ² is preferably a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C ₁ -C ₃ alkyl group, or (C ₁ -C ₃ alkoxy) C ₁ -C. ₃ alkyl group, which may be substituted benzoyl group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group (said halogen atom is fluorine atom, chlorine selected from the group consisting of and bromine are the same or different 1 to 3 halogen atoms.), selected from the group consisting of cyclopropyl group, a cyano group and a tri (C ₁ -C ₃ alkyl) silyl group Or the same or different 1 to 2 substituents. }, C ₂ -C ₄ alkoxycarbonyl group, may be substituted phenoxy group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group (said halogen The atoms are the same or different 1 to 3 halogen atoms selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom.), Cyclopropyl group, cyano group and tri (C ₁ -C ₃ alkyl) It is the same or different 1-2 substituents selected from the group consisting of silicon groups. }, Which may be substituted phenylthio group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group (said halogen atom is a fluorine atom, a chlorine atom and The same or different one to three halogen atoms selected from the group consisting of bromine atoms), the same selected from the group consisting of cyclopropyl groups, cyano groups and tri (C ₁ -C ₃ alkyl) silicon groups. Or it is 1 to 2 different substituents. } Or a tri (C ₁ -C ₃ alkyl) silicon group,
More preferably, a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethoxycarbonyl group or a trimethylsilyl group,
Even more preferred is a hydrogen atom.

(C) In the present invention, R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are preferably independently of each other a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a substituted atom. A good C ₁ -C ₄ alkyl group (the substituent is the same or different 1 to 3 substituents selected from the group consisting of fluorine atom, chlorine atom and bromine atom, or C ₃ -C ₄ cycloalkyl group) A C ₁ -C ₃ alkylthio group or a C ₁ -C ₃ alkoxyimino group), a C ₂ -C ₃ alkenyl group, a C ₂ -C ₃ alkynyl group, an optionally substituted C ₃ -C ₅ cycloalkyl group. (the substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₃ -C ₄ cycloalkyl group, a cyano group, C ₁ -C ₃ alkoxy groups and C ₁ -C ₃ alkylthio group 1 to 3 identical or different selected from the group consisting of Is a substituent.), C ₆ ~C ₇ bicycloalkyl group, a cyano group, C ₂ -C ₄ alkylcarbonyl group, C ₂ -C ₄ alkoxycarbonyl groups, which may be substituted phenyl group {said substituent is fluorine atoms 1, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl or C ₁ -C ₃ haloalkyl group (said halogen atom is a fluorine atom, the same or different selected from the group consisting of chlorine and bromine 3 halogen atoms). }, A 5- to 6-membered heterocyclic group which may be substituted {the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and further contains 1 to 2 nitrogen atoms. You can. The substituents are fluorine atom, chlorine atom, bromine atom, C ₁ -C ₃ alkyl and C ₁ -C ₃ haloalkyl group (said halogen atom is a fluorine atom, selected from the group consisting of chlorine and bromine 1 to 3 halogen atoms which are the same or different. }, Nitro group, C ₁ -C ₃ alkoxy groups, C ₁ -C ₃ haloalkoxy group (said halogen atom is a fluorine atom, 1-3 was selected same or different from the group consisting of chlorine and bromine of a halogen atom.), which may be substituted phenoxy group (the substituent is a fluorine atom, a chlorine atom, pyridazinium substituted with a substituent selected from bromine atom, and C ₁ -C ₃ alkoxy group Gini oxy Or a C ₁ -C ₃ alkylthio group, or R ³ , R ⁴ , R ⁵ , R ^6, and R ⁷ are the two adjacent groups together with the carbon atom to which they are attached. _{Te, -CH 2 CH 2 -, -} CH 2 CH 2 CH 2 -, - CH (CH 3) CH 2 CH 2 -, - CH 2 CH 2 CH 2 CH 2 -, - CH = CH-CH = CH- , -OCH ₂ CH _2- , -OCH = CH-, -OCH = C (CH ₃ )-, -SCH = CH-, -N = CH-CH = CH-, -OCH ₂ O-, -OCH ₂ CH ₂ O-,

A group represented by
More preferably, independently of each other, a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an optionally substituted C ₁ -C ₄ alkyl group (the substituent is 1 to 3 fluorine atoms, or a one cyclopropyl group.), C ₂ ~C ₃ alkenyl group, optionally substituted C ₃ to -C ₄ cycloalkyl group (said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₂ alkyl group, the same one to two substituents selected from the group consisting of cyclopropyl group, and C ₁ -C ₂ alkoxy group.), a cyano group, C ₂ -C ₃ alkoxycarbonyl group, a nitro A group, a C ₁ -C ₃ alkoxy group or a trifluoromethoxy group, or R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ , together with the carbon atoms to which two adjacent ones are attached to each other It is _{to, -CH 2 CH 2 CH 2 -} , - CH (CH 3) CH 2 CH 2 -, - OCH 2 CH 2 - -OCH = CH- or

Wherein R ³ is not a hydrogen atom,
Even more preferably, independently of each other, a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C ₁ -C ₃ alkyl group, a C ₂ -C ₃ alkenyl group, an optionally substituted C ₃ -C ₄ cycloalkyl group (said substituent is the same 1 to 2 substituents selected from the group consisting of a chlorine atom and C ₁ -C ₂ alkyl group.), a cyano group or a C ₁ -C ₂ alkoxy group Or R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ , together with the carbon atom to which each of the two adjacent groups is bonded, —CH ₂ CH ₂ CH ₂ — or —OCH = CH-, provided that R ³ is not a hydrogen atom,
Particularly preferably, independently of each other, a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an allyl group, an isopropyl group, an optionally substituted cyclopropyl group (the substituent is 2 chlorine atoms) or a methoxy group, or R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ , together with the carbon atom to which two adjacent ones are bonded to each other. , -CH ₂ CH ₂ CH ₂ - is a or a group represented by -OCH = CH-, provided that, R ³ is not a hydrogen atom,
Most preferably, R ³ is a fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, isopropyl group, cyclopropyl group or methoxy group, and R ⁷ is a hydrogen atom, fluorine atom , A chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an isopropyl group, a cyclopropyl group or a methoxy group, and R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom or a methyl group It is.

  (D) In the present invention, m and n are preferably both 0.

The compound (I) of the present invention is preferably
(1a) R ¹ is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a C ₁ -C ₃ alkyl group, a C ₁ -C ₃ haloalkyl group (the halogen atom is 1 to 3 fluorine atoms). ), cyclopropyl, C ₂ -C ₃ alkenyl group, a cyano group, C ₂ -C ₄ alkylcarbonyl group, a di (C ₁ -C ₃ alkyl) carbamoyl group, which may be substituted phenyl group {said substituent, fluorine atom, chlorine atom, bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group (said halogen atom is a fluorine atom, and the same or different selected from the group consisting of chlorine and bromine 1 ˜3 halogen atoms), a cyclopropyl group, a cyano group, and a tri (C ₁ -C ₃ alkyl) silicon group are the same or different 1-2 substituents selected from the group consisting of. }, A furyl group, a thienyl group, C ₁ -C ₃ alkoxy group, which may be substituted phenoxy group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ A haloalkyl group (the halogen atom is 1 to 3 fluorine atoms), a cyclopropyl group, a cyano group, and a tri (C ₁ -C ₃ alkyl) silicon group selected from the same or different 1 Two substituents. } Or a substituted pyrazolyloxy group (the substituent is one benzoyl group and two C ₁ -C ₃ alkyl groups substituted by two chlorine atoms),
(1b) R ² may be substituted with a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C ₁ -C ₃ alkyl group, a (C ₁ -C ₃ alkoxy) C ₁ -C ₃ alkyl group, Benzoyl group {the substituent is a fluorine atom, a chlorine atom, a bromine atom, a C ₁ -C ₃ alkyl group, a C ₁ -C ₃ haloalkyl group (the halogen atom is a group consisting of a fluorine atom, a chlorine atom and a bromine atom) The same or different 1 to 3 halogen atoms selected), the same or different 1 to 2 selected from the group consisting of a cyclopropyl group, a cyano group and a tri (C ₁ -C ₃ alkyl) silicon group. Substituents. }, C ₂ -C ₄ alkoxycarbonyl group, may be substituted phenoxy group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group (said halogen The atoms are the same or different 1 to 3 halogen atoms selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom.), Cyclopropyl group, cyano group and tri (C ₁ -C ₃ alkyl) It is the same or different 1-2 substituents selected from the group consisting of silicon groups. }, Which may be substituted phenylthio group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group (said halogen atom is a fluorine atom, a chlorine atom and The same or different one to three halogen atoms selected from the group consisting of bromine atoms), the same selected from the group consisting of cyclopropyl groups, cyano groups and tri (C ₁ -C ₃ alkyl) silicon groups. Or it is 1 to 2 different substituents. } Or a tri (C ₁ -C ₃ alkyl) silicon group,
(1c) R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a C ₁ -C ₄ alkyl group which may be substituted. (The substituent is the same or different 1 to 3 substituents selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom, or a C _{3 to} C ₄ cycloalkyl group, a C _{1 to} C ₃ alkylthio group. Or a C ₁ -C ₃ alkoxyimino group.), A C ₂ -C ₃ alkenyl group, a C ₂ -C ₃ alkynyl group, an optionally substituted C ₃ -C ₅ cycloalkyl group (the substituent is a fluorine atom) , a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₃ -C ₄ cycloalkyl group, a cyano group, the same or are selected from C ₁ -C ₃ alkoxy groups and C ₁ -C ₃ alkylthio group different from 1 to 3 substituents.), C ₆ ~C _7-bi Black alkyl group, a cyano group, C ₂ -C ₄ alkylcarbonyl group, C ₂ -C ₄ alkoxycarbonyl group, which may be substituted phenyl group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group or C ₁ -C ₃ haloalkyl group (the halogen atom is the same or different 1 to 3 halogen atoms selected from the group consisting of fluorine atom, chlorine atom and bromine atom). }, A 5- to 6-membered heterocyclic group which may be substituted {the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and further contains 1 to 2 nitrogen atoms. You can. The substituents are fluorine atom, chlorine atom, bromine atom, C ₁ -C ₃ alkyl and C ₁ -C ₃ haloalkyl group (said halogen atom is a fluorine atom, selected from the group consisting of chlorine and bromine 1 to 3 halogen atoms which are the same or different. }, Nitro group, C ₁ -C ₃ alkoxy groups, C ₁ -C ₃ haloalkoxy group (said halogen atom is a fluorine atom, 1-3 was selected same or different from the group consisting of chlorine and bromine of a halogen atom.), which may be substituted phenoxy group (the substituent is a fluorine atom, a chlorine atom, pyridazinium substituted with a substituent selected from bromine atom, and C ₁ -C ₃ alkoxy group Gini oxy Or a C ₁ -C ₃ alkylthio group, or R ³ , R ⁴ , R ⁵ , R ^6, and R ⁷ are bonded together with the carbon atom to which they are adjacent to each other. _{Te, -CH 2 CH 2 -, -} CH 2 CH 2 CH 2 -, - CH (CH 3) CH 2 CH 2 -, - CH 2 CH 2 CH 2 CH 2 -, - CH = CH-CH = CH- , -OCH ₂ CH _2- , -OCH = CH-, -OCH = C (CH ₃ )-, -SCH = CH-, -N = CH-CH = CH-, -OCH ₂ O-, -OCH ₂ CH ₂ O-,

A group represented by
(1d) a compound in which m and n are both 0;
More preferably,
(2a) R ¹ is a chlorine atom, a bromine atom, a trifluoromethyl group or a cyano group,
(2b) R ² is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethoxycarbonyl group or a trimethylsilyl group,
^{(2c) R 3, R 4} , R 5, R 6 and R ^7, independently of one another, a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, may be substituted C ₁ -C ₄ alkyl group (The substituent is 1 to 3 fluorine atoms or one cyclopropyl group), a C _{2 to} C ₃ alkenyl group, an optionally substituted C _{3 to} C ₄ cycloalkyl group (the substituent group, a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₂ alkyl group, the same one or two substituents selected from the group consisting of cyclopropyl group, and C ₁ -C ₂ alkoxy group.) , A cyano group, a C ₂ -C ₃ alkoxycarbonyl group, a nitro group, a C ₁ -C ₃ alkoxy group or a trifluoromethoxy group, or R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are adjacent to each other. Two of them, together with the carbon atom to which each is attached, are —CH ₂ CH ₂ CH ₂ —, —CH (C H ₃ ) CH ₂ CH _2- , -OCH ₂ CH _2- , -OCH = CH- or

Wherein R ³ is not a hydrogen atom,
(2d) a compound in which m and n are both 0;
Even more preferably,
(3a) R ¹ is a chlorine atom or a bromine atom,
(3b) R ² is a hydrogen atom,
(3c) R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, C ₁ -C ₃ alkyl group, C _2- C ₃ alkenyl group, may be substituted C ₃ -C ₄ cycloalkyl group (the substituent is the same 1 to 2 substituents selected from the group consisting of a chlorine atom and C ₁ -C ₂ alkyl group ), A cyano group or a C ₁ -C ₂ alkoxy group, or R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ , together with two adjacent carbon atoms to which each is bonded. A group represented by —CH ₂ CH ₂ CH ₂ — or —OCH═CH—, wherein R ³ is not a hydrogen atom,
(3d) a compound in which m and n are both 0;
Particularly preferably,
(4a) R ¹ is a chlorine atom,
(4b) R ² is a hydrogen atom,
(4c) R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, allyl group, isopropyl group , An optionally substituted cyclopropyl group (the substituent is two chlorine atoms) or a methoxy group, or R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are adjacent to each other. Are groups represented by —CH ₂ CH ₂ CH ₂ — or —OCH═CH—, together with the carbon atoms to which each is bonded, provided that R ³ is not a hydrogen atom,
(4d) a compound in which m and n are both 0;
Most preferably, 6-chloro-3- (2-iodophenoxy) -4-pyridazinol, 6-chloro-3- (2-methylphenoxy) -4-pyridazinol, 6-chloro-3- (2-isopropylphenoxy) ) -4-pyridazinol, 6-chloro-3- (2-cyclopropylphenoxy) -4-pyridazinol, 6-chloro-3- (2,3-dihydro-1H-inden-4-yloxy) -4-pyridazinol, 3- (1-benzofuran-7-yloxy) -6-chloro-4-pyridazinol, 6-chloro-3- (2,5-dimethylphenoxy) -4-pyridazinol, 6-chloro-3- (2-methoxy- 5-methylphenoxy) -4-pyridazinol, 6-chloro-3- (2-chloro-6-methylphenoxy) -4-pyridazinol, 6-chloro-3- (2-chloro-6-cyclopropylphenoxy) -4 -Pyridazinol, 3- (2-bromo-6-methylphenoxy) -6-chloro-4-pyridazinol, 6-chloro-3- (2-ethyl-6-methylphenoxy) -4-pyridazinol, 6-chloro-3 - (2-Cyclopropyl-6-methylphenoxy) -4-pyridazinol, 3- (2-allyl-6-methylphenoxy) -6-chloro-4-pyridazinol, 6-chloro-3- (2-cyclopropyl-3 , 5-dimethylphenoxy) -4-pyridazinol, 6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinol or 6-chloro-3- (2,3,5,6-tetramethylphenoxy) -4-pyridazinol.

  Representative compounds of the present invention are illustrated in Table 1 below, but the present invention is not limited to these compounds.

Hereinafter, in R ^{3 to} R ⁷ , “H” means that R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are all hydrogen atoms, and in R ^{3 to} R ⁷ , “2-Cl” means that R ³ is R ^3. “Me” represents a methyl group, “Et” represents an ethyl group, “Pr” represents a propyl group, “iPr” represents an isopropyl group, “cPr” represents a cyclopropyl group, “Bu”. `` Is a butyl group, `` iBu '' is an isobutyl group, `` sBu '' is a sec-butyl group, `` tBu '' is a tert-butyl group, `` cBu '' is a cyclobutyl group, `` Pen '' is a pentyl group, "cPen" means cyclopentyl, "neoPen" is a neopentyl group, "Hx" means a hexyl group, "cHx" is a cyclohexyl group, _{"2-CH 2 CH 2 CH 2} -3 " in R ³ to R ⁷ Indicates that R ³ and R ⁴ are trimethylene groups and together with the carbon atoms to which they are attached form a 5-membered ring, “= N-OMe” is a methoxyimino group, “= O” is So A carbonyl group together with the carbon atom to which al is attached, _{"SO 2 (Ph-4-Me} ) " is a p- tolyl sulfonyl group, "cPr-1-F" is a 1-fluoro-cyclopropyl group, `` CPr-cis-2- (CH ₂ ) ₃ -cis-3 '' is a formula

`` C (-CH ₂ CH ₂ -)-CH ₂ CH ₂ '' is a group represented by the formula

In the group represented by the formula, “CH (CH ₂ ) CH—CH ₂ ” represents the formula

In the group represented by the formula, “CH (OCH ₂ ) ₂ ”

`` Fur '' is a furyl group, `` Thi '' is a thienyl group, `` Pyr '' is a pyridyl group, `` Azr '' is an aziridinyl group, `` Pyrd '' is a pyrrolidinyl group, `` Pyrr '' Is a pyrrolyl group, “Pyza” is a pyrazolyl group, “Thiz” is a thiazolyl group, “Pyzn” is a pyridazinyl group, “Np” is a naphthyl group, “1-Ad” is a 1-adamantyl group, “ "Ioxa" is an isoxazolyl group, "Tdia" is a 1,2,3-thiadiazolyl group, "Bfur" is a 1-benzofuranyl group, "Bthi" is a 1-benzothienyl group, "Bthia" is 1,3- Benzothiazolyl group, “Boxaz” is 1,3-benzodioxolyl group, “Iqu” is isoquinolyl group, “Azet” is azetidinyl group, “Ppri” is piperidyl group, “1-Ppri-4- `` OCH ₂ CH ₂ O-4 '' is a formula

`` Ppra '' is a piperazinyl group, `` Morp '' is a morpholinyl group, `` Tmor '' is a thiomorpholinyl group, `` Carb '' is a carbazolyl group, `` Pthia '' is a phenothiazinyl group, `` Thpy "the in-tetrahydro -2H- pyranyl group," Q ¹ "is oxiranyl group," Q ² "is benzoxazolyl group," Q ³ "is benzothiazolyl group," Q ⁴ "fluorenyl group," “Q ⁵ ” represents a 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl group, and “Q ⁶ ” represents 6-chloro-3- (2-methylphenoxy) -4 -Pyridazinyl group, “Q ⁷ ” is 6-chloro-3- (2-isopropylphenoxy) -4-pyridazinyl group, “Q ⁸ ” is 6-chloro-3- (2-cyclopropylphenoxy) -4- pyridazinyl group, "Q ^9" is 6-chloro-3- (2,3-dihydro -1H Indene-4-yloxy) -4-pyridazinyl group, a "Q ^10" is 6-chloro-3- (2,6-dimethylphenoxy) -4-pyridazinyl group, "Q ^11" is 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl group, “Q ¹² ” is 4- [2-chloro-3- (methoxycarbonyl) -4- (methylsulfonyl) benzoyl] -1-ethyl- 1H-pyrazol-5-yl group, “Q ¹³ ” represents 4- (2,4-dichloro-3-methylbenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl group, “Q ¹⁴ ”. Represents 2- [2-chloro-4- (methylsulfonyl) benzoyl] -3-oxo-1-cyclohexen-1-yl group, “Q ¹⁵ ” represents 2- [4- (methylsulfonyl) -2-nitrobenzoyl ] -3-Oxo-1-cycl Hexene-1-yl group, "Q ^16" are 2-cyano-1-cyclopropyl-3- [2- (methylsulfonyl) -4- (trifluoromethyl) phenyl] -3-oxo-1-propenyl group “Q ¹⁷ ” represents a 3- [4-chloro-2- (methylsulfonyl) phenyl] -2-cyano-1-cyclopropyl-3-oxo-1-propenyl group, and “Q ¹⁸ ” represents 3,4 -Dihydro-2 (1H) -isoquinolinyl group, “Q ¹⁹ ” represents a 1,3-oxazolidin-3-yl group, “Q ²⁰ ” represents a 2,5-dihydro-1H-pyrrol-1-yl group, “Q ²¹ ” represents a 3,6-dihydro-1 (2H) -pyridinyl group, “Q ²² ” represents a 1,4-oxazepan-4-yl group, and “Q ²³ ” represents 2,3-dihydro-1H— indol-1-yl group, "Q ^24" is 1,3-dihydro -2H- isoindole - - yl group, "Q ^25" is 3,4-dihydro -1 (2H) - quinolinyl group, the "Q ^26" is 2,3-dihydro-4H-1,4-benzoxazin-4-yl group , Respectively.

(Table 1)
――――――――――――――――――――――――――――――――――――
Compound number R ¹ R ² XR ^Three ~ R ⁷ mn
――――――――――――――――――――――――――――――――――――
1 HHHH 0 0
2 HHH 2-Cl 0 0
3 HHH 2-Br 0 0
4 HHH 2-I 0 0
5 HHH 2-Me 0 0
6 HHH 2-iPr 0 0
7 HHH 2-cPr 0 0
8 HHH 2-cBu 0 0
9 HHH 2-CH ₂ CH ₂ CH ₂ -3 0 0
10 HHH 2-cPr, 5-Me 0 0
11 HHH 2-OMe, 5-Me 0 0
12 HHH 2-F, 6-iPr 0 0
13 HHH 2-Cl, 6-cPr 0 0
14 HHH 2-Br, 6-Me 0 0
15 HHH 2-I, 6-Me 0 0
16 HHH 2,6-Me ₂ 0 0
17 HHH 2-Me, 6-Et 0 0
18 HHH 2-Me, 6-cPr 0 0
19 HHH 2,6-cPr ₂ 0 0
20 HHH 2-cPr, 3,5-Me ₂ 0 0
21 HHH 2-cPr, 5,6-Me ₂ 0 0
22 HH SO ₂ (Ph-4-Me) 2-Cl 0 0
23 HH SO ₂ (Ph-4-Me) 2-Br 0 0
24 HH SO ₂ (Ph-4-Me) 2-I 0 0
25 HH SO ₂ (Ph-4-Me) 2-Me 0 0
26 HH SO ₂ (Ph-4-Me) 2-iPr 0 0
27 HH SO ₂ (Ph-4-Me) 2-cPr 0 0
28 HH SO ₂ (Ph-4-Me) 2-cBu 0 0
29 HH SO ₂ (Ph-4-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
30 HH SO ₂ (Ph-4-Me) 2-cPr, 5-Me 0 0
31 HH SO ₂ (Ph-4-Me) 2-OMe, 5-Me 0 0
32 HH SO ₂ (Ph-4-Me) 2-F, 6-iPr 0 0
33 HH SO ₂ (Ph-4-Me) 2-Cl, 6-cPr 0 0
34 HH SO ₂ (Ph-4-Me) 2-Br, 6-Me 0 0
35 HH SO ₂ (Ph-4-Me) 2-I, 6-Me 0 0
36 HH SO ₂ (Ph-4-Me) 2,6-Me ₂ 0 0
37 HH SO ₂ (Ph-4-Me) 2-Me, 6-Et 0 0
38 HH SO ₂ (Ph-4-Me) 2-Me, 6-cPr 0 0
39 HH SO ₂ (Ph-4-Me) 2,6-cPr ₂ 0 0
40 HH SO ₂ (Ph-4-Me) 2-cPr, 3,5-Me ₂ 0 0
41 HH SO ₂ (Ph-4-Me) 2-cPr, 5,6-Me ₂ 0 0
42 H Cl H 2-Cl 0 0
43 H Cl H 2-Br 0 0
44 H Cl H 2-I 0 0
45 H Cl H 2-Me 0 0
46 H Cl H 2-Et 0 0
47 H Cl H 2-iPr 0 0
48 H Cl H 2-cPr 0 0
49 H Cl H 2-cBu 0 0
50 H Cl H 2-CH ₂ CH ₂ CH ₂ -3 0 0
51 H Cl H 2-cPr, 5-Me 0 0
52 H Cl H 2-OMe, 5-Me 0 0
53 H Cl H 2-F, 6-iPr 0 0
54 H Cl H 2-Cl, 6-cPr 0 0
55 H Cl H 2-Br, 6-Me 0 0
56 H Cl H 2-I, 6-Me 0 0
57 H Cl H 2,6-Me ₂ 0 0
58 H Cl H 2-Me, 6-Et 0 0
59 H Cl H 2-Me, 6-cPr 0 0
60 H Cl H 2,6-cPr ₂ 0 0
61 H Cl H 2-cPr, 3,5-Me ₂ 0 0
62 H Cl H 2-cPr, 5,6-Me ₂ 0 0
63 H Cl SO ₂ (Ph-4-Me) 2-Cl 0 0
64 H Cl SO ₂ (Ph-4-Me) 2-Br 0 0
65 H Cl SO ₂ (Ph-4-Me) 2-I 0 0
66 H Cl SO ₂ (Ph-4-Me) 2-Me 0 0
67 H Cl SO ₂ (Ph-4-Me) 2-iPr 0 0
68 H Cl SO ₂ (Ph-4-Me) 2-cPr 0 0
69 H Cl SO ₂ (Ph-4-Me) 2-cBu 0 0
70 H Cl SO ₂ (Ph-4-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
71 H Cl SO ₂ (Ph-4-Me) 2-cPr, 5-Me 0 0
72 H Cl SO ₂ (Ph-4-Me) 2-OMe, 5-Me 0 0
73 H Cl SO ₂ (Ph-4-Me) 2-F, 6-iPr 0 0
74 H Cl SO ₂ (Ph-4-Me) 2-Cl, 6-cPr 0 0
75 H Cl SO ₂ (Ph-4-Me) 2-Br, 6-Me 0 0
76 H Cl SO ₂ (Ph-4-Me) 2-I, 6-Me 0 0
77 H Cl SO ₂ (Ph-4-Me) 2,6-Me ₂ 0 0
78 H Cl SO ₂ (Ph-4-Me) 2-Me, 6-Et 0 0
79 H Cl SO ₂ (Ph-4-Me) 2-Me, 6-cPr 0 0
80 H Cl SO ₂ (Ph-4-Me) 2,6-cPr ₂ 0 0
81 H Cl SO ₂ (Ph-4-Me) 2-cPr, 3,5-Me ₂ 0 0
82 H Cl SO ₂ (Ph-4-Me) 2-cPr, 5,6-Me ₂ 0 0
83 H SiMe _Three H 2-Cl 0 0
84 H SiMe _Three H 2-Br 0 0
85 H SiMe _Three H 2-I 0 0
86 H SiMe _Three H 2-Me 0 0
87 H SiMe _Three H 2-iPr 0 0
88 H SiMe _Three H 2-cPr 0 0
89 H SiMe _Three H 2-cBu 0 0
90 H SiMe _Three H 2-CH ₂ CH ₂ CH ₂ -3 0 0
91 H SiMe _Three H 2-cPr, 5-Me 0 0
92 H SiMe _Three H 2-OMe, 5-Me 0 0
93 H SiMe _Three H 2-F, 6-iPr 0 0
94 H SiMe _Three H 2-Cl, 6-cPr 0 0
95 H SiMe _Three H 2-Br, 6-Me 0 0
96 H SiMe _Three H 2-I, 6-Me 0 0
97 H SiMe _Three H 2,6-Me ₂ 0 0
98 H SiMe _Three H 2-Me, 6-Et 0 0
99 H SiMe _Three H 2-Me, 6-cPr 0 0
100 H SiMe _Three H 2,6-cPr ₂ 0 0
101 H SiMe _Three H 2-cPr, 3,5-Me ₂ 0 0
102 H SiMe _Three H 2-cPr, 5,6-Me ₂ 0 0
103 H SiMe _Three SO ₂ (Ph-4-Me) 2-Cl 0 0
104 H SiMe _Three SO ₂ (Ph-4-Me) 2-Br 0 0
105 H SiMe _Three SO ₂ (Ph-4-Me) 2-I 0 0
106 H SiMe _Three SO ₂ (Ph-4-Me) 2-Me 0 0
107 H SiMe _Three SO ₂ (Ph-4-Me) 2-iPr 0 0
108 H SiMe _Three SO ₂ (Ph-4-Me) 2-cPr 0 0
109 H SiMe _Three SO ₂ (Ph-4-Me) 2-cBu 0 0
110 H SiMe _Three SO ₂ (Ph-4-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
111 H SiMe _Three SO ₂ (Ph-4-Me) 2-cPr, 5-Me 0 0
112 H SiMe _Three SO ₂ (Ph-4-Me) 2-OMe, 5-Me 0 0
113 H SiMe _Three SO ₂ (Ph-4-Me) 2-F, 6-iPr 0 0
114 H SiMe _Three SO ₂ (Ph-4-Me) 2-Cl, 6-cPr 0 0
115 H SiMe _Three SO ₂ (Ph-4-Me) 2-Br, 6-Me 0 0
116 H SiMe _Three SO ₂ (Ph-4-Me) 2-I, 6-Me 0 0
117 H SiMe _Three SO ₂ (Ph-4-Me) 2,6-Me ₂ 0 0
118 H SiMe _Three SO ₂ (Ph-4-Me) 2-Me, 6-Et 0 0
119 H SiMe _Three SO ₂ (Ph-4-Me) 2-Me, 6-cPr 0 0
120 H SiMe _Three SO ₂ (Ph-4-Me) 2,6-cPr ₂ 0 0
121 H SiMe _Three SO ₂ (Ph-4-Me) 2-cPr, 3,5-Me ₂ 0 0
122 H SiMe _Three SO ₂ (Ph-4-Me) 2-cPr, 5,6-Me ₂ 0 0
123 Cl HHH 0 0
124 Cl HH 2-F 0 0
125 Cl HH 2-Cl 0 0
126 Cl HH 2-Br 0 0
127 Cl HH 2-I 0 0
128 Cl HH 2-Me 0 0
129 Cl HH 2-Me 1 0
130 Cl HH 2-Et 0 0
131 Cl HH 2-Pr 0 0
132 Cl HH 2-iPr 0 0
133 Cl HH 2-Bu 0 0
134 Cl HH 2-iBu 0 0
135 Cl HH 2-sBu 0 0
136 Cl HH 2-tBu 0 0
137 Cl HH 2-Pen 0 0
138 Cl HH 2-Hx 0 0
139 Cl HH 2-cPr 0 0
140 Cl HH 2- (cPr-1-F) 0 0
141 Cl HH 2- (cPr-1-Cl) 0 0
142 Cl HH 2- (cPr-1-Br) 0 0
143 Cl HH 2- (cPr-1-I) 0 0
144 Cl HH 2- (cPr-1-Me) 0 0
145 Cl HH 2- (cPr-1-Et) 0 0
146 Cl HH 2- (cPr-1-Pr) 0 0
147 Cl HH 2- (cPr-1-iPr) 0 0
148 Cl HH 2- (cPr-1-Bu) 0 0
149 Cl HH 2- (cPr-1-tBu) 0 0
150 Cl HH 2- (cPr-1-Hx) 0 0
151 Cl HH 2- (cPr-1-cPr) 0 0
152 Cl HH 2- (cPr-1-cBu) 0 0
153 Cl HH 2- (cPr-1-cPen) 0 0
154 Cl HH 2- (cPr-1-CH ₂ F) 0 0
155 Cl HH 2- (cPr-1-CH ₂ Cl) 0 0
156 Cl HH 2- (cPr-1-CH ₂ Br) 0 0
157 Cl HH 2- (cPr-1-CHF ₂ ) 0 0
158 Cl HH 2- (cPr-1-CF _Three ) 0 0
159 Cl HH 2- (cPr-1-CCl _Three ) 0 0
160 Cl HH 2- (cPr-1-CH ₂ CF _Three ) 0 0
161 Cl HH 2- (cPr-1-CH ₂ CCl _Three ) 0 0
162 Cl HH 2- (cPr-1-CH = CH ₂ ) 0 0
163 Cl HH 2- (cPr-1-CH ₂ OMe) 0 0
164 Cl HH 2- (cPr-1-CH ₂ OEt) 0 0
165 Cl HH 2- (cPr-1-CH ₂ OiPr) 0 0
166 Cl HH 2- (cPr-1-CH ₂ SMe) 0 0
167 Cl HH 2- (cPr-1-CH ₂ SEt) 0 0
168 Cl HH 2- (cPr-1-CH ₂ S-iPr) 0 0
169 Cl HH 2- (cPr-1-CH ₂ SOMe) 0 0
170 Cl HH 2- (cPr-1-CH ₂ SOEt) 0 0
171 Cl HH 2- (cPr-1-CH ₂ SO ₂ Me) 0 0
172 Cl HH 2- (cPr-1-CH ₂ SO ₂ Et) 0 0
173 Cl HH 2- (cPr-1-CN) 0 0
174 Cl HH 2- {cPr-1-C (= NOMe) Me} 0 0
175 Cl HH 2- (cPr-1-COMe) 0 0
176 Cl HH 2- (cPr-1-COEt) 0 0
177 Cl HH 2- (cPr-1-COPh) 0 0
178 Cl HH 2- (cPr-1-CO ₂ H) 0 0
179 Cl HH 2- (cPr-1-CO ₂ Me) 0 0
180 Cl HH 2- (cPr-1-CO ₂ Et) 0 0
181 Cl HH 2- (cPr-1-CONH ₂ ) 0 0
182 Cl HH 2- (cPr-1-CONMe ₂ ) 0 0
183 Cl HH 2- (cPr-1-CONEt ₂ ) 0 0
184 Cl HH 2- (cPr-1-Ph) 0 0
185 Cl HH 2- {cPr-1- (Ph-2-F)} 0 0
186 Cl HH 2- {cPr-1- (Ph-2-Cl)} 0 0
187 Cl HH 2- {cPr-1- (Ph-2-Me)} 0 0
188 Cl HH 2- {cPr-1- (Ph-4-Cl)} 0 0
189 Cl HH 2- {cPr-1- (Ph-4-Me)} 0 0
190 Cl HH 2- {cPr-1- (2-Fur)} 0 0
191 Cl HH 2- {cPr-1- (2-Thi)} 0 0
192 Cl HH 2- {cPr-1- (2-Pyr)} 0 0
193 Cl HH 2- (cPr-1-NH ₂ ) 0 0
194 Cl HH 2- (cPr-1-NHMe) 0 0
195 Cl HH 2- (cPr-1-NMe ₂ ) 0 0
196 Cl HH 2- (cPr-1-NHCOMe) 0 0
197 Cl HH 2- (cPr-1-NHCO ₂ Me) 0 0
198 Cl HH 2- (cPr-1-NHCONMe ₂ ) 0 0
199 Cl HH 2- (cPr-1-NHSO ₂ Me) 0 0
200 Cl HH 2- (cPr-1-NO ₂ ) 0 0
201 Cl HH 2- (cPr-1-OH) 0 0
202 Cl HH 2- (cPr-1-OMe) 0 0
203 Cl HH 2- (cPr-1-OEt) 0 0
204 Cl HH 2- (cPr-1-OCF _Three ) 0 0
205 Cl HH 2- (cPr-1-OPh) 0 0
206 Cl HH 2- (cPr-1-SMe) 0 0
207 Cl HH 2- (cPr-1-SEt) 0 0
208 Cl HH 2- (cPr-1-SPh) 0 0
209 Cl HH 2- (cPr-1-SOMe) 0 0
210 Cl HH 2- (cPr-1-SOEt) 0 0
211 Cl HH 2- (cPr-1-SO ₂ Me) 0 0
212 Cl HH 2- (cPr-1-SO ₂ Et) 0 0
213 Cl HH 2- (cPr-2-F) 0 0
214 Cl HH 2- (cPr-2-Cl) 0 0
215 Cl HH 2- (cPr-2-Br) 0 0
216 Cl HH 2- (cPr-2-I) 0 0
217 Cl HH 2- (cPr-2-Me) 0 0
218 Cl HH 2- (cPr-2-Et) 0 0
219 Cl HH 2- (cPr-2-Pr) 0 0
220 Cl HH 2- (cPr-2-iPr) 0 0
221 Cl HH 2- (cPr-2-Bu) 0 0
222 Cl HH 2- (cPr-2-tBu) 0 0
223 Cl HH 2- (cPr-2-Hx) 0 0
224 Cl HH 2- (cPr-2-cPr) 0 0
225 Cl HH 2- (cPr-2-CF _Three ) 0 0
226 Cl HH 2- (cPr-2-CN) 0 0
227 Cl HH 2- (cPr-2-CH ₂ OMe) 0 0
228 Cl HH 2- (cPr-2-CH ₂ OEt) 0 0
229 Cl HH 2- {cPr-2-C (= NOMe) Me} 0 0
230 Cl HH 2- (cPr-2-COMe) 0 0
231 Cl HH 2- (cPr-2-COEt) 0 0
232 Cl HH 2- (cPr-2-COPh) 0 0
233 Cl HH 2- (cPr-2-CO ₂ H) 0 0
234 Cl HH 2- (cPr-2-CO ₂ Me) 0 0
235 Cl HH 2- (cPr-2-CO ₂ Et) 0 0
236 Cl HH 2- (cPr-2-CONH ₂ ) 0 0
237 Cl HH 2- (cPr-2-CONMe ₂ ) 0 0
238 Cl HH 2- (cPr-2-CONEt ₂ ) 0 0
239 Cl HH 2- (cPr-2-NH ₂ ) 0 0
240 Cl HH 2- (cPr-2-NHMe) 0 0
241 Cl HH 2- (cPr-2-NMe ₂ ) 0 0
242 Cl HH 2- (cPr-2-NHCOMe) 0 0
243 Cl HH 2- (cPr-2-NHCO ₂ Me) 0 0
244 Cl HH 2- (cPr-2-NHCONMe ₂ ) 0 0
245 Cl HH 2- (cPr-2-NHSO ₂ Me) 0 0
246 Cl HH 2- (cPr-2-NO ₂ ) 0 0
247 Cl HH 2- (cPr-2-OH) 0 0
248 Cl HH 2- (cPr-2-OMe) 0 0
249 Cl HH 2- (cPr-2-OEt) 0 0
250 Cl HH 2- (cPr-2-OCF _Three ) 0 0
251 Cl HH 2- (cPr-2-OPh) 0 0
252 Cl HH 2- (cPr-2-SMe) 0 0
253 Cl HH 2- (cPr-2-SEt) 0 0
254 Cl HH 2- (cPr-2-SPh) 0 0
255 Cl HH 2- (cPr-2-SOMe) 0 0
256 Cl HH 2- (cPr-2-SOEt) 0 0
257 Cl HH 2- (cPr-2-SO ₂ Me) 0 0
258 Cl HH 2- (cPr-2-SO ₂ Et) 0 0
259 Cl HH 2- (cPr-1,2-Me ₂ ) 0 0
260 Cl HH 2- (cPr-1-Me-2-Et) 0 0
261 Cl HH 2- (cPr-1-Et-2-Me) 0 0
262 Cl HH 2- (cPr-1,2-Et ₂ ) 0 0
263 Cl HH 2- {cPr-1,2- (CN) ₂ } 0 0
264 Cl HH 2- (cPr-2,2-F ₂ ) 0 0
265 Cl HH 2- (cPr-2,2-Cl ₂ ) 0 0
266 Cl HH 2- (cPr-2,2-Br ₂ ) 0 0
267 Cl HH 2- (cPr-2,2-Me ₂ ) 0 0
268 Cl HH 2- {cPr-2,2- (CN) ₂ } 0 0
269 Cl HH 2- (cPr-2-cis-3-cis-Me ₂ ) 0 0
270 Cl HH 2- (cPr-2-cis-3-trans-Me ₂ ) 0 0
271 Cl HH 2- (cPr-2-trans-3-trans-Me ₂ ) 0 0
272 Cl HH 2- {cPr-cis-2- (CH ₂ ) _Three -cis-3} 0 0
273 Cl HH 2- {cPr-trans-2- (CH ₂ ) _Three -trans-3} 0 0
274 Cl HH 2- {cPr-cis-2- (CH ₂ ) _Four -cis-3} 0 0
275 Cl HH 2- (cPr-trans-2- (CH ₂ ) _Four -trans-3) 0 0
276 Cl HH 2- {cPr-2,3- (CN) ₂ } 0 0
277 Cl HH 2- (cPr-1,2,2-Me _Three ) 0 0
278 Cl HH 2- (cPr-1,2,3-Me _Three ) 0 0
279 Cl HH 2- (cPr-2,2,3-cis-Me _Three ) 0 0
280 Cl HH 2- (cPr-2,2,3-trans-Me _Three ) 0 0
281 Cl HH 2- (cPr-1,2,2,3-Me _Four ) 0 0
282 Cl HH 2- (cPr-2,2,3,3-Me _Four ) 0 0
283 Cl HH 2- (cPr-1,2,2,3,3-Me _Five ) 0 0
284 Cl HH 2-cBu 0 0
285 Cl HH 2- (cBu-1-Me) 0 0
286 Cl HH 2- (cBu-1-CH = CH ₂ ) 0 0
287 Cl HH 2- (cBu-1-CN) 0 0
288 Cl HH 2- (cBu-1-CO ₂ H) 0 0
289 Cl HH 2- (cBu-1-COMe) 0 0
290 Cl HH 2- (cBu-1-CO ₂ Me) 0 0
291 Cl HH 2- (cBu-1-NH ₂ ) 0 0
292 Cl HH 2-cPen 0 0
293 Cl HH 2-cHx 0 0
294 Cl HH 2-CH ₂ F 0 0
295 Cl HH 2-CH ₂ Cl 0 0
296 Cl HH 2-CH ₂ Br 0 0
297 Cl HH 2-CHF ₂ 0 0
298 Cl HH 2-CHCl ₂ 0 0
299 Cl HH 2-CHBr ₂ 0 0
300 Cl HH 2-CF _Three 0 0
301 Cl HH 2-CCl _Three 0 0
302 Cl HH 2-CBr _Three 0 0
303 Cl HH 2-CH = CH ₂ 0 0
304 Cl HH 2-CMe = CH ₂ 0 0
305 Cl HH 2-CH = CHMe 0 0
306 Cl HH 2-CH = CHCN 0 0
307 Cl HH 2-CH ₂ CH = CH ₂ 0 0
308 Cl HH 2-C≡CH 0 0
309 Cl HH 2-C≡CMe 0 0
310 Cl HH 2-C≡CSiMe _Three 0 0
311 Cl HH 2-CH ₂ cPr 0 0
312 Cl HH 2-CH ₂ cBu 0 0
313 Cl HH 2-CH ₂ cPen 0 0
314 Cl HH 2-CH ₂ cHx 0 0
315 Cl HH 2-CH ₂ Ph 0 0
316 Cl HH 2-CH ₂ CN 0 0
317 Cl HH 2-CHMeCN 0 0
318 Cl HH 2-CMe ₂ CN 0 0
319 Cl HH 2-CH ₂ COMe 0 0
320 Cl HH 2-CH ₂ CO ₂ Me 0 0
321 Cl HH 2-CHMeCO ₂ Me 0 0
322 Cl HH 2-CH ₂ CO ₂ Et 0 0
323 Cl HH 2-CHMeCO ₂ Et 0 0
324 Cl HH 2-CH ₂ OMe 0 0
325 Cl HH 2-CH ₂ OEt 0 0
326 Cl HH 2-CH ₂ SMe 0 0
327 Cl HH 2-CH ₂ SO ₂ Et 0 0
328 Cl HH 2-CH (OMe) ₂ 0 0
329 Cl HH 2-CH (OCH ₂ ) ₂ 0 0
330 Cl HH 2-CN 0 0
331 Cl HH 2-CH = NOH 0 0
332 Cl HH 2-CH = NOMe 0 0
333 Cl HH 2-CMe = NOH 0 0
334 Cl HH 2-CMe = NOMe 0 0
335 Cl HH 2-CHO 0 0
336 Cl HH 2-COMe 0 0
337 Cl HH 2-COtBu 0 0
338 Cl HH 2-COPh 0 0
339 Cl HH 2-CO ₂ Me 0 0
340 Cl HH 2-CO ₂ tBu 0 0
341 Cl HH 2-CO ₂ H 0 0
342 Cl HH 2-CONH ₂ 0 0
343 Cl HH 2-CONMe ₂ 0 0
344 Cl HH 2-Ph 0 0
345 Cl HH 2- (Ph-2-Cl) 0 0
346 Cl HH 2- (Ph-2-Me) 0 0
347 Cl HH 2- (Ph-2-CF _Three ) 0 0
348 Cl HH 2- (Ph-3-CF _Three ) 0 0
(Isomer A)
349 Cl HH 2- (Ph-3-CF _Three ) 0 0
(Isomer B)
350 Cl HH 2- (1-Azr) 0 0
351 Cl HH 2- (2-Azr) 0 0
352 Cl HH 2- {2-Azr-1-SO ₂ (Ph-4-Me)} 0 0
353 Cl HH 2- (2-Q ¹ -2-Me) 0 0
354 Cl HH 2- (2-Q ¹ -3-Me) 0 0
355 Cl HH 2- (1-Pyrd) 0 0
356 Cl HH 2- (1-Pyrr) 0 0
357 Cl HH 2- (2-Fur) 0 0
358 Cl HH 2- (3-Fur) 0 0
359 Cl HH 2- (2-Thi) 0 0
360 Cl HH 2- (2-Thi-3-Cl) 0 0
361 Cl HH 2- (3-Thi) 0 0
362 Cl HH 2- (1-Pyza) 0 0
363 Cl HH 2- (1-Pyza-3-Me) 0 0
364 Cl HH 2- (1-Pyza-3,5-Me ₂ ) 0 0
365 Cl HH 2- (1-Pyza-3-CF _Three ) 0 0
366 Cl HH 2- (1-Pyza-4-CF _Three ) 0 0
367 Cl HH 2- (1-Pyza-5-CF _Three ) 0 0
368 Cl HH 2- (3-Pyza-1-SO ₂ NMe ₂ ) 0 0
369 Cl HH 2- (5-Pyza-1-SO ₂ NMe ₂ ) 0 0
370 Cl HH 2- (2-Thiz-4-Me) 0 0
371 Cl HH 2- (2-Pyr) 0 0
372 Cl HH 2- (3-Pyr) 0 0
373 Cl HH 2- (4-Pyr) 0 0
374 Cl HH 2- (1-Pyr-2-OH) 0 0
375 Cl HH 2- (2-Q ² ) 0 0
376 Cl HH 2- (2-Q ^Three ) 0 0
377 Cl HH 2-NH ₂ 0 0
378 Cl HH 2-NHMe 0 0
379 Cl HH 2-NMe ₂ 0 0
380 Cl HH 2-NHCOMe 0 0
381 Cl HH 2-NHCO ₂ Me 0 0
382 Cl HH 2-NHCONMe ₂ 0 0
383 Cl HH 2-NO ₂ 0 0
384 Cl HH 2-OH 0 0
385 Cl HH 2-OMe 0 0
386 Cl HH 2-OEt 0 0
387 Cl HH 2-OiPr 0 0
388 Cl HH 2-OtBu 0 0
389 Cl HH 2-OCH ₂ F 0 0
390 Cl HH 2-OCHF ₂ 0 0
391 Cl HH 2-OCF _Three 0 0
392 Cl HH 2-OCH ₂ CF _Three 0 0
393 Cl HH 2-OCH ₂ CCl _Three 0 0
394 Cl HH 2-OCH ₂ OMe 0 0
395 Cl HH 2-OCH ₂ OEt 0 0
396 Cl HH 2-OCH ₂ CH ₂ OMe 0 0
397 Cl HH 2-OCH ₂ CH ₂ OEt 0 0
398 Cl HH 2-OPh 0 0
399 Cl HH 2-O (Ph-2-OH) 0 0
400 Cl HH 2-O {Ph-2-O (3-Pyzn-6-Cl-4-OEt)} 0 0
401 Cl HH 2-SMe 0 0
402 Cl HH 2-SEt 0 0
403 Cl HH 2-S-iPr 0 0
404 Cl HH 2-SOMe 0 0
405 Cl HH 2-SOEt 0 0
406 Cl HH 2-SO ₂ Me 0 0
407 Cl HH 2-SO ₂ Et 0 0
408 Cl HH 2-SiMe _Three 0 0
409 Cl HH 3-F 0 0
410 Cl HH 3-Cl 0 0
411 Cl HH 3-Br 0 0
412 Cl HH 3-I 0 0
413 Cl HH 3-Me 0 0
414 Cl HH 3-Et 0 0
415 Cl HH 3-iPr 0 0
416 Cl HH 3-tBu 0 0
417 Cl HH 3-cPr 0 0
418 Cl HH 3-CF _Three 0 0
419 Cl HH 3- (2-Fur) 0 0
420 Cl HH 3-CN 0 0
421 Cl HH 3-CHO 0 0
422 Cl HH 3-COMe 0 0
423 Cl HH 3-CO ₂ Me 0 0
424 Cl HH 3-NO ₂ 0 0
425 Cl HH 3-OMe 0 0
426 Cl HH 4-F 0 0
427 Cl HH 4-Cl 0 0
428 Cl HH 4-Br 0 0
429 Cl HH 4-I 0 0
430 Cl HH 4-Me 0 0
431 Cl HH 4-Et 0 0
432 Cl HH 4-iPr 0 0
433 Cl HH 4-tBu 0 0
434 Cl HH 4-cPr 0 0
435 Cl HH 4-OMe 0 0
436 Cl HH 4-SiMe _Three 0 0
437 Cl HH 2,3-F ₂ 0 0
438 Cl HH 2-F, 3-Cl 0 0
439 Cl HH 2-F, 3-Br 0 0
440 Cl HH 2-F, 3-Me 0 0
441 Cl HH 2-F, 3-CF _Three 0 0
442 Cl HH 2-Cl, 3-F 0 0
443 Cl HH 2,3-Cl ₂ 0 0
444 Cl HH 2-Cl, 3-Br 0 0
445 Cl HH 2-Cl, 3-Me 0 0
446 Cl HH 2-Cl, 3-CF _Three 0 0
447 Cl HH 2-Cl, 3-OMe 0 0
448 Cl HH 2-Br, 3-F 0 0
449 Cl HH 2-Br, 3-Cl 0 0
450 Cl HH 2-Br, 3-Me 0 0
451 Cl HH 2-Br, 3-CF _Three 0 0
452 Cl HH 2-Br, 3-OMe 0 0
453 Cl HH 2-Me, 3-F 0 0
454 Cl HH 2-Me, 3-Cl 0 0
455 Cl HH 2-Me, 3-Br 0 0
456 Cl HH 2,3-Me ₂ 0 0
457 Cl HH 2-Me, 3-CF _Three 0 0
458 Cl HH 2-Me, 3-NO ₂ 0 0
459 Cl HH 2-Me, 3-OMe 0 0
460 Cl HH 2-Me, 3-O (3-Pyzn-6-Cl-4-OH) 0 0
461 Cl HH 2-Et, 3-F 0 0
462 Cl HH 2-Et, 3-Cl 0 0
463 Cl HH 2-Et, 3-Br 0 0
464 Cl HH 2-Et, 3-Me 0 0
465 Cl HH 2-iPr, 3-F 0 0
466 Cl HH 2-iPr, 3-Cl 0 0
467 Cl HH 2-iPr, 3-Me 0 0
468 Cl HH 2-iPr, 3-Et 0 0
469 Cl HH 2-cPr, 3-F 0 0
470 Cl HH 2-cPr, 3-Cl 0 0
471 Cl HH 2-cPr, 3-Br 0 0
472 Cl HH 2-cPr, 3-Me 0 0
473 Cl HH 2-cPr, 3-Et 0 0
474 Cl HH 2-cPr, 3-CF _Three 0 0
475 Cl HH 2-cPr, 3-CN 0 0
476 Cl HH 2-cPr, 3-CO ₂ Me 0 0
477 Cl HH 2-cPr, 3-NO ₂ 0 0
478 Cl HH 2-cPr, 3-OMe 0 0
479 Cl HH 2-cBu, 3-F 0 0
480 Cl HH 2-cBu, 3-Cl 0 0
481 Cl HH 2-cBu, 3-Br 0 0
482 Cl HH 2-cBu, 3-Me 0 0
483 Cl HH 2-CF _Three , 3-F 0 0
484 Cl HH 2-CF _Three , 3-Cl 0 0
485 Cl HH 2-CF _Three , 3-Br 0 0
486 Cl HH 2-CF _Three , 3-Me 0 0
487 Cl HH 2-CN, 3-F 0 0
488 Cl HH 2-CN, 3-Cl 0 0
489 Cl HH 2-CN, 3-Br 0 0
490 Cl HH 2-CN, 3-Me 0 0
491 Cl HH 2-CO ₂ Me, 3-F 0 0
492 Cl HH 2-CO ₂ Me, 3-Cl 0 0
493 Cl HH 2-CO ₂ Me, 3-Br 0 0
494 Cl HH 2-CO ₂ Me, 3-Me 0 0
495 Cl HH 2-NO ₂ , 3-F 0 0
496 Cl HH 2-NO ₂ , 3-Cl 0 0
497 Cl HH 2-NO ₂ , 3-Br 0 0
498 Cl HH 2-NO ₂ , 3-Me 0 0
499 Cl HH 2-OMe, 3-F 0 0
500 Cl HH 2-OMe, 3-Cl 0 0
501 Cl HH 2-OMe, 3-Br 0 0
502 Cl HH 2-OMe, 3-Me 0 0
503 Cl HH 2-OMe, 3-OMe 0 0
504 Cl HH 2-CH ₂ -3 0 0
505 Cl HH 2-CH ₂ CH ₂ -3 0 0
506 Cl HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
507 Cl HH 2-CHMeCH ₂ CH ₂ -3 0 0
508 Cl HH 2-CH (OMe) CH ₂ CH ₂ -3 0 0
509 Cl HH 2-CH ₂ CHMeCH ₂ -3 0 0
510 Cl HH 2-CH ₂ CH ₂ CHMe-3 0 0
511 Cl HH 2-CMe ₂ CH ₂ CH ₂ -3 0 0
512 Cl HH 2-C (OMe) ₂ CH ₂ CH ₂ -3 0 0
513 Cl HH 2-CH ₂ CMe ₂ CH ₂ -3 0 0
514 Cl HH 2-C (-CH ₂ CH ₂ -)-CH ₂ CH ₂ -3 0 0
515 Cl HH 2-CH (CH ₂ ) CH-CH ₂ -3 0 0
516 Cl HH 2-CH ₂ -CH (CH ₂ ) CH-3 0 0
517 Cl HH 2-C (= O) CH ₂ CH ₂ -3 0 0
518 Cl HH 2-CH ₂ C (= O) CH ₂ -3 0 0
519 Cl HH 2-CH ₂ CH ₂ C (= O) -3 0 0
520 Cl HH 2-C (= NOMe) CH ₂ CH ₂ -3 0 0
521 Cl HH 2-CH ₂ CH ₂ CH ₂ CH ₂ -3 0 0
522 Cl HH 2-CHMeCH ₂ CH ₂ CH ₂ -3 0 0
523 Cl HH 2-CMe ₂ CH ₂ CH ₂ CH ₂ -3 0 0
524 Cl HH 2-C (-CH ₂ CH ₂ -)-CH ₂ CH ₂ CH ₂ -3 0 0
525 Cl HH 2-CH (CH ₂ ) CH-CH ₂ CH ₂ -3 0 0
526 Cl HH 2-CH (OMe) CH ₂ CH ₂ CH ₂ -3 0 0
527 Cl HH 2-CH = CHCH = CH-3 0 0
528 Cl HH 2-CH ₂ CH ₂ O-3 0 0
529 Cl HH 2-CHMeCH ₂ O-3 0 0
530 Cl HH 2-CH ₂ CHMeO-3 0 0
531 Cl HH 2-CH = CH-O-3 0 0
532 Cl HH 2-CMe = CH-O-3 0 0
533 Cl HH 2-CH = CMe-O-3 0 0
534 Cl HH 2-CH = CH-S-3 0 0
535 Cl HH 2-N = CHCH = CH-3 0 0
(Isomer A)
536 Cl HH 2-N = CHCH = CH-3 0 0
(Isomer B)
537 Cl HH 2-N = CH-O-3 0 0
538 Cl HH 2-N = CMe-O-3 0 0
539 Cl HH 2-OCH ₂ CH ₂ -3 0 0
540 Cl HH 2-OCMe ₂ CH ₂ -3 0 0
541 Cl HH 2-OCH = CH-3 0 0
542 Cl HH 2-OCMe = CH-3 0 0
543 Cl HH 2-OCF ₂ O-3 0 0
544 Cl HH 2-OCH ₂ O-3 0 0
545 Cl HH 2-OCHMeO-3 0 0
546 Cl HH 2-OCMe ₂ O-3 0 0
547 Cl HH 2-OCH ₂ CH ₂ O-3 0 0
548 Cl HH 2-OCH = N-3 0 0
549 Cl HH 2-OCMe = N-3 0 0
550 Cl HH 2,4-F ₂ 0 0
551 Cl HH 2-Cl, 4-F 0 0
552 Cl HH 2,4-Cl ₂ 0 0
553 Cl HH 2-Br, 4-F 0 0
554 Cl HH 2,4-Br ₂ 0 0
555 Cl HH 2-Br, 4-Me 0 0
556 Cl HH 2-Br, 4-tBu 0 0
557 Cl HH 2-Me, 4-F 0 0
558 Cl HH 2-Me, 4-Cl 0 0
559 Cl HH 2,4-Me ₂ 0 0
560 Cl HH 2-Et, 4-F 0 0
561 Cl HH 2-Et, 4-Cl 0 0
562 Cl HH 2-Et, 4-I 0 0
563 Cl HH 2-Et, 4-Me 0 0
564 Cl HH 2-iPr, 4-F 0 0
565 Cl HH 2-iPr, 4-Cl 0 0
566 Cl HH 2-iPr, 4-Br 0 0
567 Cl HH 2-tBu, 4-Me 0 0
568 Cl HH 2-cPr, 4-F 0 0
569 Cl HH 2-cPr, 4-Cl 0 0
570 Cl HH 2-cPr, 4-Br 0 0
571 Cl HH 2-cPr, 4-Me 0 0
572 Cl HH 2-cPr, 4-Et 0 0
573 Cl HH 2-cPr, 4-CF _Three 0 0
574 Cl HH 2-cPr, 4-CN 0 0
575 Cl HH 2-cPr, 4-CO ₂ Me 0 0
576 Cl HH 2-cPr, 4-NO ₂ 0 0
577 Cl HH 2-cPr, 4-OMe 0 0
578 Cl HH 2-cBu, 4-F 0 0
579 Cl HH 2-cBu, 4-Cl 0 0
580 Cl HH 2-cBu, 4-Br 0 0
581 Cl HH 2-cBu, 4-Me 0 0
582 Cl HH 2-CF _Three , 4-F 0 0
583 Cl HH 2-CF _Three , 4-Cl 0 0
584 Cl HH 2-CF _Three , 4-Br 0 0
585 Cl HH 2-CF _Three , 4-Me 0 0
586 Cl HH 2-CN, 4-F 0 0
587 Cl HH 2-CN, 4-Cl 0 0
588 Cl HH 2-CN, 4-Br 0 0
589 Cl HH 2-CN, 4-Me 0 0
590 Cl HH 2-CO ₂ Me, 4-F 0 0
591 Cl HH 2-CO ₂ Me, 4-Cl 0 0
592 Cl HH 2-CO ₂ Me, 4-Br 0 0
593 Cl HH 2-CO ₂ Me, 4-Me 0 0
594 Cl HH 2-NO ₂ , 4-F 0 0
595 Cl HH 2-NO ₂ , 4-Cl 0 0
596 Cl HH 2-NO ₂ , 4-Br 0 0
597 Cl HH 2-NO ₂ , 4-Me 0 0
598 Cl HH 2-OMe, 4-F 0 0
599 Cl HH 2-OMe, 4-Cl 0 0
600 Cl HH 2-OMe, 4-Br 0 0
601 Cl HH 2-OMe, 4-Me 0 0
602 Cl HH 2,4- (OMe) ₂ 0 0
603 Cl HH 2,5-F ₂ 0 0
604 Cl HH 2-F, 5-Cl 0 0
605 Cl HH 2-F, 5-Br 0 0
606 Cl HH 2-F, 5-I 0 0
607 Cl HH 2-F, 5-Me 0 0
608 Cl HH 2-F, 5-CF _Three 0 0
609 Cl HH 2-F, 5-OMe 0 0
610 Cl HH 2-Cl, 5-F 0 0
611 Cl HH 2,5-Cl ₂ 0 0
612 Cl HH 2-Cl, 5-Br 0 0
613 Cl HH 2-Cl, 5-I 0 0
614 Cl HH 2-Cl, 5-Me 0 0
615 Cl HH 2-Cl, 5-CF _Three 0 0
616 Cl HH 2-Cl, 5-OMe 0 0
617 Cl HH 2-Me, 5-F 0 0
618 Cl HH 2-Me, 5-Cl 0 0
619 Cl HH 2-Me, 5-Br 0 0
620 Cl HH 2-Me, 5-I 0 0
621 Cl HH 2,5-Me ₂ 0 0
622 Cl HH 2-Me, 5-Et 0 0
623 Cl HH 2-Me, 5-iPr 0 0
624 Cl HH 2-Me, 5-CF _Three 0 0
625 Cl HH 2-Me, 5-CN 0 0
626 Cl HH 2-Me, 5-CO ₂ H 0 0
627 Cl HH 2-Me, 5-NH ₂ 0 0
628 Cl HH 2-Me, 5-NMe ₂ 0 0
629 Cl HH 2-Me, 5-OMe 0 0
630 Cl HH 2-Et, 5-F 0 0
631 Cl HH 2-Et, 5-Cl 0 0
632 Cl HH 2-Et, 5-Br 0 0
633 Cl HH 2-Et, 5-Me 0 0
634 Cl HH 2-Et, 5-CN 0 0
635 Cl HH 2-Et, 5-OMe 0 0
636 Cl HH 2-iPr, 5-F 0 0
637 Cl HH 2-iPr, 5-Cl 0 0
638 Cl HH 2-iPr, 5-Br 0 0
639 Cl HH 2-iPr, 5-I 0 0
640 Cl HH 2-iPr, 5-Me 0 0
641 Cl HH 2-iPr, 5-Et 0 0
642 Cl HH 2-iPr, 5-iPr 0 0
643 Cl HH 2-iPr, 5-CF _Three 0 0
644 Cl HH 2-iPr, 5-CN 0 0
645 Cl HH 2-iPr, 5-OMe 0 0
646 Cl HH 2-tBu, 5-F 0 0
647 Cl HH 2-tBu, 5-Cl 0 0
648 Cl HH 2-tBu, 5-Br 0 0
649 Cl HH 2-tBu, 5-I 0 0
650 Cl HH 2-tBu, 5-Me 0 0
651 Cl HH 2-tBu, 5-Et 0 0
652 Cl HH 2-tBu, 5-iPr 0 0
653 Cl HH 2-tBu, 5-tBu 0 0
654 Cl HH 2-tBu, 5-cPr 0 0
655 Cl HH 2-tBu, 5-CF _Three 0 0
656 Cl HH 2-tBu, 5-CN 0 0
657 Cl HH 2-tBu, 5-OMe 0 0
658 Cl HH 2-cPr, 5-F 0 0
659 Cl HH 2-cPr, 5-Cl 0 0
660 Cl HH 2-cPr, 5-Br 0 0
661 Cl HH 2-cPr, 5-I 0 0
662 Cl HH 2-cPr, 5-Me 0 0
663 Cl HH 2-cPr, 5-Et 0 0
664 Cl HH 2-cPr, 5-iPr 0 0
665 Cl HH 2-cPr, 5-tBu 0 0
666 Cl HH 2-cPr, 5-CF _Three 0 0
667 Cl HH 2-cPr, 5-CN 0 0
668 Cl HH 2-cPr, 5-OMe 0 0
669 Cl HH 2-CF _Three , 5-F 0 0
670 Cl HH 2-CF _Three , 5-Cl 0 0
671 Cl HH 2-CF _Three , 5-Br 0 0
672 Cl HH 2-CF _Three , 5-I 0 0
673 Cl HH 2-CF _Three , 5-Me 0 0
674 Cl HH 2-CF _Three , 5-CN 0 0
675 Cl HH 2-CF _Three , 5-OMe 0 0
676 Cl HH 2-CH = CH ₂ , 5-F 0 0
677 Cl HH 2-CH = CH ₂ , 5-Cl 0 0
678 Cl HH 2-CH = CH ₂ , 5-Me 0 0
679 Cl HH 2-CH = CHMe, 5-F 0 0
680 Cl HH 2-CH = CHMe, 5-Cl 0 0
681 Cl HH 2-CH = CHMe, 5-Me 0 0
682 Cl HH 2-CMe = CH ₂ , 5-F 0 0
683 Cl HH 2-CMe = CH ₂ , 5-Cl 0 0
684 Cl HH 2-CMe = CH ₂ , 5-Me 0 0
685 Cl HH 2-CN, 5-F 0 0
686 Cl HH 2-CN, 5-Cl 0 0
687 Cl HH 2-CN, 5-Br 0 0
688 Cl HH 2-CN, 5-I 0 0
689 Cl HH 2-CN, 5-Me 0 0
690 Cl HH 2-CN, 5-CN 0 0
691 Cl HH 2-CN, 5-OMe 0 0
692 Cl HH 2-CHO, 5-NMe ₂ 0 0
693 Cl HH 2-CO ₂ Me, 5-F 0 0
694 Cl HH 2-CO ₂ Me, 5-Cl 0 0
695 Cl HH 2-CO ₂ Me, 5-Br 0 0
696 Cl HH 2-CO ₂ Me, 5-I 0 0
697 Cl HH 2-CO ₂ Me, 5-Me 0 0
698 Cl HH 2-CO ₂ Me, 5-CN 0 0
699 Cl HH 2-CO ₂ Me, 5-OMe 0 0
700 Cl HH 2-OMe, 5-F 0 0
701 Cl HH 2-OMe, 5-Cl 0 0
702 Cl HH 2-OMe, 5-Br 0 0
703 Cl HH 2-OMe, 5-I 0 0
704 Cl HH 2-OMe, 5-Me 0 0
705 Cl HH 2-OMe, 5-Et 0 0
706 Cl HH 2-OMe, 5-CF _Three 0 0
707 Cl HH 2-OMe, 5-CN 0 0
708 Cl HH 2-OMe, 5-NO ₂ 0 0
709 Cl HH 2-OMe, 5-OMe 0 0
710 Cl HH 2,6-F ₂ 0 0
711 Cl HH 2-F, 6-Cl 0 0
712 Cl HH 2-F, 6-Br 0 0
713 Cl HH 2-F, 6-I 0 0
714 Cl HH 2-F, 6-Me 0 0
715 Cl HH 2-F, 6-Et 0 0
716 Cl HH 2-F, 6-Pr 0 0
717 Cl HH 2-F, 6-iPr 0 0
718 Cl HH 2-F, 6-tBu 0 0
719 Cl HH 2-F, 6-cPr 0 0
720 Cl HH 2-F, 6-cBu 0 0
721 Cl HH 2-F, 6-cPen 0 0
722 Cl HH 2-F, 6-CF _Three 0 0
723 Cl HH 2-F, 6-CH ₂ OMe 0 0
724 Cl HH 2-F, 6-CH ₂ OEt 0 0
725 Cl HH 2-F, 6-CH ₂ CH ₂ OMe 0 0
726 Cl HH 2-F, 6-CH ₂ SMe 0 0
727 Cl HH 2-F, 6-CH ₂ SEt 0 0
728 Cl HH 2-F, 6-CHMeSEt 0 0
729 Cl HH 2-F, 6-CN 0 0
730 Cl HH 2-F, 6-CO ₂ Me 0 0
731 Cl HH 2-F, 6-NO ₂ 0 0
732 Cl HH 2-F, 6-OMe 0 0
733 Cl HH 2,6-Cl ₂ 0 0
734 Cl HH 2-Cl, 6-Br 0 0
735 Cl HH 2-Cl, 6-I 0 0
736 Cl HH 2-Cl, 6-Me 0 0
737 Cl HH 2-Cl, 6-Et 0 0
738 Cl HH 2-Cl, 6-iPr 0 0
739 Cl HH 2-Cl, 6-tBu 0 0
740 Cl HH 2-Cl, 6-cPr 0 0
741 Cl HH 2-Cl, 6-cBu 0 0
742 Cl HH 2-Cl, 6-cPen 0 0
743 Cl HH 2-Cl, 6-CF _Three 0 0
744 Cl HH 2-Cl, 6-CH = CH ₂ 0 0
745 Cl HH 2-Cl, 6-CH ₂ CH = CH ₂ 0 0
746 Cl HH 2-Cl, 6-CH ₂ CMe = CH ₂ 0 0
747 Cl HH 2-Cl, 6-CH ₂ OMe 0 0
748 Cl HH 2-Cl, 6-CH ₂ OEt 0 0
749 Cl HH 2-Cl, 6-CH ₂ CH ₂ OMe 0 0
750 Cl HH 2-Cl, 6-CH ₂ SMe 0 0
751 Cl HH 2-Cl, 6-CH ₂ SEt 0 0
752 Cl HH 2-Cl, 6-CN 0 0
753 Cl HH 2-Cl, 6-CO ₂ Me 0 0
754 Cl HH 2-Cl, 6-NO ₂ 0 0
755 Cl HH 2-Cl, 6-OMe 0 0
756 Cl HH 2,6-Br ₂ 0 0
757 Cl HH 2-Br, 6-I 0 0
758 Cl HH 2-Br, 6-Me 0 0
759 Cl HH 2-Br, 6-Et 0 0
760 Cl HH 2-Br, 6-iPr 0 0
761 Cl HH 2-Br, 6-tBu 0 0
762 Cl HH 2-Br, 6-cPr 0 0
763 Cl HH 2-Br, 6-cBu 0 0
764 Cl HH 2-Br, 6-cPen 0 0
765 Cl HH 2-Br, 6-cHx 0 0
766 Cl HH 2-Br, 6-CF _Three 0 0
767 Cl HH 2-Br, 6-CH = CH ₂ 0 0
768 Cl HH 2-Br, 6-CH ₂ CH = CH ₂ 0 0
769 Cl HH 2-Br, 6-CH ₂ CMe = CH ₂ 0 0
770 Cl HH 2-Br, 6-CH ₂ OMe 0 0
771 Cl HH 2-Br, 6-CH ₂ OEt 0 0
772 Cl HH 2-Br, 6-CH ₂ CH ₂ OMe 0 0
773 Cl HH 2-Br, 6-CH ₂ SMe 0 0
774 Cl HH 2-Br, 6-CH ₂ SEt 0 0
775 Cl HH 2-Br, 6-CN 0 0
776 Cl HH 2-Br, 6-CO ₂ Me 0 0
777 Cl HH 2-Br, 6-NO ₂ 0 0
778 Cl HH 2-Br, 6-OMe 0 0
779 Cl HH 2,6-I ₂ 0 0
780 Cl HH 2-I, 6-Me 0 0
781 Cl HH 2-I, 6-Et 0 0
782 Cl HH 2-I, 6-iPr 0 0
783 Cl HH 2-I, 6-tBu 0 0
784 Cl HH 2-I, 6-cPr 0 0
785 Cl HH 2-I, 6-cBu 0 0
786 Cl HH 2-I, 6-cPen 0 0
787 Cl HH 2-I, 6-cHx 0 0
788 Cl HH 2-I, 6-CF _Three 0 0
789 Cl HH 2-I, 6-CH = CH ₂ 0 0
790 Cl HH 2-I, 6-CH ₂ CH = CH ₂ 0 0
791 Cl HH 2-I, 6-CH ₂ CMe = CH ₂ 0 0
792 Cl HH 2-I, 6-CH ₂ OMe 0 0
793 Cl HH 2-I, 6-CH ₂ OEt 0 0
794 Cl HH 2-I, 6-CH ₂ CH ₂ OMe 0 0
795 Cl HH 2-I, 6-CH ₂ SMe 0 0
796 Cl HH 2-I, 6-CH ₂ SEt 0 0
797 Cl HH 2-I, 6-CN 0 0
798 Cl HH 2-I, 6-CO ₂ Me 0 0
799 Cl HH 2-I, 6-NO ₂ 0 0
800 Cl HH 2-I, 6-OMe 0 0
801 Cl HH 2,6-Me ₂ 0 0
802 Cl HH 2-Me, 6-Et 0 0
803 Cl HH 2-Me, 6-iPr 0 0
804 Cl HH 2-Me, 6-sBu 0 0
805 Cl HH 2-Me, 6-tBu 0 0
806 Cl HH 2-Me, 6-cPr 0 0
807 Cl HH 2-Me, 6- (cPr-1-F) 0 0
808 Cl HH 2-Me, 6- (cPr-1-Cl) 0 0
809 Cl HH 2-Me, 6- (cPr-1-Br) 0 0
810 Cl HH 2-Me, 6- (cPr-1-I) 0 0
811 Cl HH 2-Me, 6- (cPr-1-Me) 0 0
812 Cl HH 2-Me, 6- (cPr-1-Et) 0 0
813 Cl HH 2-Me, 6- (cPr-1-cPr) 0 0
814 Cl HH 2-Me, 6- (cPr-1-CN) 0 0
815 Cl HH 2-Me, 6- (cPr-1-OMe) 0 0
816 Cl HH 2-Me, 6- (cPr-1-OEt) 0 0
817 Cl HH 2-Me, 6- (cPr-2-Me) 0 0
818 Cl HH 2-Me, 6- (cPr-2-Et) 0 0
819 Cl HH 2-Me, 6- (cPr-2-CN) 0 0
820 Cl HH 2-Me, 6- (cPr-2-OMe) 0 0
821 Cl HH 2-Me, 6- (cPr-2-OEt) 0 0
822 Cl HH 2-Me, 6- (cPr-2-OCF _Three ) 0 0
823 Cl HH 2-Me, 6- (cPr-1,2-Me ₂ ) 0 0
824 Cl HH 2-Me, 6- {cPr-1,2- (CN) ₂ } 0 0
825 Cl HH 2-Me, 6- (cPr-2,2-Me ₂ ) 0 0
826 Cl HH 2-Me, 6- (cPr-2,2-F ₂ ) 0 0
827 Cl HH 2-Me, 6- (cPr-2,2-Cl ₂ ) 0 0
828 Cl HH 2-Me, 6- (cPr-2,2-Br ₂ ) 0 0
829 Cl HH 2-Me, 6- {cPr-2,2- (CN) ₂ } 0 0
830 Cl HH 2-Me, 6-cBu 0 0
831 Cl HH 2-Me, 6-cPen 0 0
832 Cl HH 2-Me, 6-cHx 0 0
833 Cl HH 2-Me, 6-CF _Three 0 0
834 Cl HH 2-Me, 6-CH = CH ₂ 0 0
835 Cl HH 2-Me, 6-CH ₂ CH = CH ₂ 0 0
836 Cl HH 2-Me, 6-CH = CH-NO ₂ 0 0
837 Cl HH 2-Me, 6-CH ₂ OMe 0 0
838 Cl HH 2-Me, 6-CH ₂ OEt 0 0
839 Cl HH 2-Me, 6-CH ₂ CH ₂ OMe 0 0
840 Cl HH 2-Me, 6-CH ₂ SMe 0 0
841 Cl HH 2-Me, 6-CH ₂ SEt 0 0
842 Cl HH 2-Me, 6-CN 0 0
843 Cl HH 2-Me, 6-CO ₂ Me 0 0
844 Cl HH 2-Me, 6-NO ₂ 0 0
845 Cl HH 2-Me, 6-OMe 0 0
846 Cl HH 2,6-Et ₂ 0 0
847 Cl HH 2-Et, 6-iPr 0 0
848 Cl HH 2-Et, 6-sBu 0 0
849 Cl HH 2-Et, 6-tBu 0 0
850 Cl HH 2-Et, 6-cPr 0 0
851 Cl HH 2-Et, 6- (cPr-1-F) 0 0
852 Cl HH 2-Et, 6- (cPr-1-Cl) 0 0
853 Cl HH 2-Et, 6- (cPr-1-Br) 0 0
854 Cl HH 2-Et, 6- (cPr-1-I) 0 0
855 Cl HH 2-Et, 6- (cPr-1-Me) 0 0
856 Cl HH 2-Et, 6- (cPr-1-Et) 0 0
857 Cl HH 2-Et, 6- (cPr-1-cPr) 0 0
858 Cl HH 2-Et, 6- (cPr-1-CN) 0 0
859 Cl HH 2-Et, 6- (cPr-1-OMe) 0 0
860 Cl HH 2-Et, 6- (cPr-1-OEt) 0 0
861 Cl HH 2-Et, 6- (cPr-2-Me) 0 0
862 Cl HH 2-Et, 6- (cPr-2-Et) 0 0
863 Cl HH 2-Et, 6- (cPr-2-CN) 0 0
864 Cl HH 2-Et, 6- (cPr-2-OMe) 0 0
865 Cl HH 2-Et, 6- (cPr-2-OEt) 0 0
866 Cl HH 2-Et, 6- (cPr-2-OCF _Three ) 0 0
867 Cl HH 2-Et, 6- (cPr-1,2-Me ₂ ) 0 0
868 Cl HH 2-Et, 6- {cPr-1,2- (CN) ₂ } 0 0
869 Cl HH 2-Et, 6- (cPr-2,2-Me ₂ ) 0 0
870 Cl HH 2-Et, 6- (cPr-2,2-F ₂ ) 0 0
871 Cl HH 2-Et, 6- (cPr-2,2-Cl ₂ ) 0 0
872 Cl HH 2-Et, 6- (cPr-2,2-Br ₂ ) 0 0
873 Cl HH 2-Et, 6- {cPr-2,2- (CN) ₂ } 0 0
874 Cl HH 2-Et, 6-cBu 0 0
875 Cl HH 2-Et, 6-cPen 0 0
876 Cl HH 2-Et, 6-cHx 0 0
877 Cl HH 2-Et, 6-CF _Three 0 0
878 Cl HH 2-Et, 6-CH = CH ₂ 0 0
879 Cl HH 2-Et, 6-CH ₂ CH = CH ₂ 0 0
880 Cl HH 2-Et, 6-CH ₂ CMe = CH ₂ 0 0
881 Cl HH 2-Et, 6-CH ₂ OMe 0 0
882 Cl HH 2-Et, 6-CH ₂ OEt 0 0
883 Cl HH 2-Et, 6-CH ₂ CH ₂ OMe 0 0
884 Cl HH 2-Et, 6-CH ₂ SMe 0 0
885 Cl HH 2-Et, 6-CH ₂ SEt 0 0
886 Cl HH 2-Et, 6-CN 0 0
887 Cl HH 2-Et, 6-CO ₂ Me 0 0
888 Cl HH 2-Et, 6-NO ₂ 0 0
889 Cl HH 2-Et, 6-OMe 0 0
890 Cl HH 2,6-Pr ₂ 0 0
891 Cl HH 2-Pr, 6-iPr 0 0
892 Cl HH 2-Pr, 6-tBu 0 0
893 Cl HH 2-Pr, 6-cPr 0 0
894 Cl HH 2,6-iPr ₂ 0 0
895 Cl HH 2-iPr, 6-tBu 0 0
896 Cl HH 2-iPr, 6-cPr 0 0
897 Cl HH 2-iPr, 6-cBu 0 0
898 Cl HH 2-iPr, 6-cPen 0 0
899 Cl HH 2-iPr, 6-cHx 0 0
900 Cl HH 2-iPr, 6-CF _Three 0 0
901 Cl HH 2-iPr, 6-CH = CH ₂ 0 0
902 Cl HH 2-iPr, 6-CH ₂ CH = CH ₂ 0 0
903 Cl HH 2-iPr, 6-CH ₂ CMe = CH ₂ 0 0
904 Cl HH 2-iPr, 6-CH ₂ OMe 0 0
905 Cl HH 2-iPr, 6-CH ₂ OEt 0 0
906 Cl HH 2-iPr, 6-CH ₂ CH ₂ OMe 0 0
907 Cl HH 2-iPr, 6-CH ₂ SMe 0 0
908 Cl HH 2-iPr, 6-CH ₂ SEt 0 0
909 Cl HH 2-iPr, 6-CN 0 0
910 Cl HH 2-iPr, 6-CO ₂ Me 0 0
911 Cl HH 2-iPr, 6-NO ₂ 0 0
912 Cl HH 2-iPr, 6-OMe 0 0
913 Cl HH 2,6-tBu ₂ 0 0
914 Cl HH 2-tBu, 6-cPr 0 0
915 Cl HH 2-tBu, 6-cBu 0 0
916 Cl HH 2-tBu, 6-cPen 0 0
917 Cl HH 2-tBu, 6-cHx 0 0
918 Cl HH 2-tBu, 6-CF _Three 0 0
919 Cl HH 2-tBu, 6-CH = CH ₂ 0 0
920 Cl HH 2-tBu, 6-CH ₂ CH = CH ₂ 0 0
921 Cl HH 2-tBu, 6-CH ₂ CMe = CH ₂ 0 0
922 Cl HH 2-tBu, 6-CH ₂ OMe 0 0
923 Cl HH 2-tBu, 6-CH ₂ OEt 0 0
924 Cl HH 2-tBu, 6-CH ₂ CH ₂ OMe 0 0
925 Cl HH 2-tBu, 6-CH ₂ SMe 0 0
926 Cl HH 2-tBu, 6-CH ₂ SEt 0 0
927 Cl HH 2-tBu, 6-CN 0 0
928 Cl HH 2-tBu, 6-CO ₂ Me 0 0
929 Cl HH 2-tBu, 6-NO ₂ 0 0
930 Cl HH 2-tBu, 6-OMe 0 0
931 Cl HH 2,6-cPr ₂ 0 0
932 Cl HH 2-cPr, 6- (cPr-1-cPr) 0 0
933 Cl HH 2-cPr, 6- (cPr-1-CN) 0 0
934 Cl HH 2-cPr, 6- (cPr-1-OMe) 0 0
935 Cl HH 2-cPr, 6- (cPr-1-OEt) 0 0
936 Cl HH 2-cPr, 6- (cPr-2-Me) 0 0
937 Cl HH 2-cPr, 6- (cPr-2-Et) 0 0
938 Cl HH 2-cPr, 6- (cPr-2-CN) 0 0
939 Cl HH 2-cPr, 6- (cPr-2-OMe) 0 0
940 Cl HH 2-cPr, 6- (cPr-2-OEt) 0 0
941 Cl HH 2-cPr, 6- (cPr-2-OCF _Three ) 0 0
942 Cl HH 2-cPr, 6- (cPr-1,2-Me ₂ ) 0 0
943 Cl HH 2-cPr, 6- {cPr-1,2- (CN) ₂ } 0 0
944 Cl HH 2-cPr, 6- (cPr-2,2-Me ₂ ) 0 0
945 Cl HH 2-cPr, 6- (cPr-2,2-F ₂ ) 0 0
946 Cl HH 2-cPr, 6- (cPr-2,2-Cl ₂ ) 0 0
947 Cl HH 2-cPr, 6- (cPr-2,2-Br ₂ ) 0 0
948 Cl HH 2-cPr, 6- {cPr-2,2- (CN) ₂ } 0 0
949 Cl HH 2-cPr, 6-cBu 0 0
950 Cl HH 2-cPr, 6-cPen 0 0
951 Cl HH 2-cPr, 6-cHx 0 0
952 Cl HH 2-cPr, 6-CF _Three 0 0
953 Cl HH 2-cPr, 6-CH = CH ₂ 0 0
954 Cl HH 2-cPr, 6-CH ₂ CH = CH ₂ 0 0
955 Cl HH 2-cPr, 6-CH ₂ CMe = CH ₂ 0 0
956 Cl HH 2-cPr, 6-CH ₂ OMe 0 0
957 Cl HH 2-cPr, 6-CH ₂ OEt 0 0
958 Cl HH 2-cPr, 6-CH ₂ CH ₂ OMe 0 0
959 Cl HH 2-cPr, 6-CH ₂ SMe 0 0
960 Cl HH 2-cPr, 6-CH ₂ SEt 0 0
961 Cl HH 2-cPr, 6-CN 0 0
962 Cl HH 2-cPr, 6-CO ₂ Me 0 0
963 Cl HH 2-cPr, 6-NO ₂ 0 0
964 Cl HH 2-cPr, 6-OMe 0 0
965 Cl HH 2-cPr, 6-OEt 0 0
966 Cl HH 2-cPr, 6-SMe 0 0
967 Cl HH 2-CF _Three , 6-CH = CH ₂ 0 0
968 Cl HH 2-CF _Three , 6-CH ₂ CH = CH ₂ 0 0
969 Cl HH 2-CF _Three , 6-CH ₂ CMe = CH ₂ 0 0
970 Cl HH 2-CF _Three , 6-CH ₂ OMe 0 0
971 Cl HH 2-CF _Three , 6-CH ₂ OEt 0 0
972 Cl HH 2-CF _Three , 6-CH ₂ CH ₂ OMe 0 0
973 Cl HH 2-CF _Three , 6-CH ₂ SMe 0 0
974 Cl HH 2-CF _Three , 6-CH ₂ SEt 0 0
975 Cl HH 2-CF _Three , 6-CN 0 0
976 Cl HH 2-CF _Three , 6-CO ₂ Me 0 0
977 Cl HH 2-CF _Three , 6-NO ₂ 0 0
978 Cl HH 2-CF _Three , 6-OMe 0 0
979 Cl HH 2,6- (CH = CHMe) ₂ 0 0
980 Cl HH 2-CH = CHMe, 6-CN 0 0
981 Cl HH 2-CH = CHMe, 6-OMe 0 0
982 Cl HH 2,6- (CH ₂ CH = CH ₂ ) ₂ 0 0
983 Cl HH 2-CH ₂ CH = CH ₂ , 6-CN 0 0
984 Cl HH 2-CH ₂ CH = CH ₂ , 6-OMe 0 0
985 Cl HH 2,6- (CN) ₂ 0 0
986 Cl HH 2-CN, 6-OMe 0 0
987 Cl HH 2,6- (OMe) ₂ 0 0
988 Cl HH 3,5-F ₂ 0 0
989 Cl HH 3-F, 5-Cl 0 0
990 Cl HH 3-F, 5-Br 0 0
991 Cl HH 3-F, 5-I 0 0
992 Cl HH 3,5-Cl ₂ 0 0
993 Cl HH 3-Cl, 5-Br 0 0
994 Cl HH 3-Cl, 5-I 0 0
995 Cl HH 3,5-Br ₂ 0 0
996 Cl HH 3-Br, 5-I 0 0
997 Cl HH 3,5-I ₂ 0 0
998 Cl HH 3,5-Me ₂ 0 0
999 Cl HH 3-Me, 5-Et 0 0
1000 Cl HH 3-Me, 5-iPr 0 0
1001 Cl HH 3-Me, 5-cPr 0 0
1002 Cl HH 3-Me, 5-cBu 0 0
1003 Cl HH 3-Me, 5-CF _Three 0 0
1004 Cl HH 3-Me, 5-CN 0 0
1005 Cl HH 3-Me, 5-NO ₂ 0 0
1006 Cl HH 3-Me, 5-OMe 0 0
1007 Cl HH 3,5-iPr ₂ 0 0
1008 Cl HH 3-iPr, 5-CF _Three 0 0
1009 Cl HH 3,5- (CF _Three ) ₂ 0 0
1010 Cl HH 2-F, 3,5-Me ₂ 0 0
1011 Cl HH 2-Cl, 3,5-Me ₂ 0 0
1012 Cl HH 2,3,5-Cl _Three 0 0
1013 Cl HH 2-Br, 3,5-Me ₂ 0 0
1014 Cl HH 2-Br, 3,5-Cl ₂ 0 0
1015 Cl HH 2-I, 3,5-Me ₂ 0 0
1016 Cl HH 2,3,5-Me _Three 0 0
1017 Cl HH 2-Me, 3,5-Cl ₂ 0 0
1018 Cl HH 2-Et, 3,5-Me ₂ 0 0
1019 Cl HH 2-Et, 3,5-Cl ₂ 0 0
1020 Cl HH 2-Pr, 3,5-Me ₂ 0 0
1021 Cl HH 2-iPr, 3,5-Me ₂ 0 0
1022 Cl HH 2-iPr, 3,5-Cl ₂ 0 0
1023 Cl HH 2-cPr, 3,5-Me ₂ 0 0
1024 Cl HH 2-cBu, 3,5-Me ₂ 0 0
1025 Cl HH 2-CN, 3,5-Me ₂ 0 0
1026 Cl HH 2-OMe, 3,5-Me ₂ 0 0
1027 Cl HH 2-SMe, 3,5-Me ₂ 0 0
1028 Cl HH 2-F, 3,6-Me ₂ 0 0
1029 Cl HH 2-F, 3-Me, 6-cPr 0 0
1030 Cl HH 2-F, 3-Me, 6-OMe 0 0
1031 Cl HH 2-Cl, 3,6-Me ₂ 0 0
1032 Cl HH 2-Cl, 3-Me, 6-cPr 0 0
1033 Cl HH 2-Cl, 3-Me, 6-OMe 0 0
1034 Cl HH 2,3,6-Cl _Three 0 0
1035 Cl HH 2,3-Cl ₂ , 6-cPr 0 0
1036 Cl HH 2-Br, 3,6-Cl ₂ 0 0
1037 Cl HH 2,6-Br ₂ , 3-Cl 0 0
1038 Cl HH 2-Br, 3-Cl, 6-cPr 0 0
1039 Cl HH 2,6-Br ₂ , 3-Me 0 0
1040 Cl HH 2-Br, 3,6-Me ₂ 0 0
1041 Cl HH 2-Br, 3-Me, 6-cPr 0 0
1042 Cl HH 2-Br, 3-Me, 6-OMe 0 0
1043 Cl HH 2,6-Br ₂ , 3-CN 0 0
1044 Cl HH 2-Br, 3-CN, 6-cPr 0 0
1045 Cl HH 2,6-Br ₂ , 3-OMe 0 0
1046 Cl HH 2-Br, 3-OMe, 6-cPr 0 0
1047 Cl HH 2-I, 3,6-Me ₂ 0 0
1048 Cl HH 2-Me, 3,6-F ₂ 0 0
1049 Cl HH 2-Me, 3-F, 6-Cl 0 0
1050 Cl HH 2-Me, 3-F, 6-Br 0 0
1051 Cl HH 2-Me, 3-F, 6-I 0 0
1052 Cl HH 2-Me, 3-F, 6-cPr 0 0
1053 Cl HH 2-Me, 3-Cl, 6-Br 0 0
1054 Cl HH 2-Me, 3-Cl, 6-I 0 0
1055 Cl HH 2-Me, 3-Cl, 6-cPr 0 0
1056 Cl HH 2,3-Me ₂ , 6-F 0 0
1057 Cl HH 2,3-Me ₂ , 6-Cl 0 0
1058 Cl HH 2,3-Me ₂ , 6-Br 0 0
1059 Cl HH 2,3-Me ₂ , 6-I 0 0
1060 Cl HH 2,3,6-Me _Three 0 0
1061 Cl HH 2,3-Me ₂ , 6-cPr 0 0
1062 Cl HH 2,3-Me ₂ , 6-CN 0 0
1063 Cl HH 2,3-Me ₂ , 6-CH = NOMe 0 0
1064 Cl HH 2,3-Me ₂ , 6-OMe 0 0
1065 Cl HH 2-Me, 3-OMe, 6-Cl 0 0
1066 Cl HH 2-Me, 3-OMe, 6-Br 0 0
1067 Cl HH 2-Me, 3-OMe, 6-I 0 0
1068 Cl HH 2,6-Me ₂ , 3-OMe 0 0
1069 Cl HH 2-Me, 3-OMe, 6-cPr 0 0
1070 Cl HH 2-cPr, 3-Me, 6-F 0 0
1071 Cl HH 2-cPr, 3-Me, 6-Cl 0 0
1072 Cl HH 2-cPr, 3-Me, 6-Br 0 0
1073 Cl HH 2-cPr, 3,6-Me ₂ 0 0
1074 Cl HH 2-cPr, 3-Me, 6-Et 0 0
1075 Cl HH 2,6-cPr ₂ , 3-Me 0 0
1076 Cl HH 2-cPr, 3-Me, 6-CN 0 0
1077 Cl HH 2-cPr, 3-Me, 6-OMe 0 0
1078 Cl HH 2-cBu, 3,6-Me ₂ 0 0
1079 Cl HH 2-CH ₂ CH = CH ₂ , 3,6-Me ₂ 0 0
1080 Cl HH 2-CH ₂ CH = CH ₂ , 3-OMe, 6-Et 0 0
1081 Cl HH 2-CN, 3,6-Me ₂ 0 0
1082 Cl HH 2-OMe, 3,6-Me ₂ 0 0
1083 Cl HH 2-CH ₂ SMe, 3,6-Me ₂ 0 0
1084 Cl HH 6-F, 2-CH ₂ CH ₂ CH ₂ -3 0 0
1085 Cl HH 6-Cl, 2-CH ₂ CH ₂ CH ₂ -3 0 0
1086 Cl HH 6-Br, 2-CH ₂ CH ₂ CH ₂ -3 0 0
1087 Cl HH 6-I, 2-CH ₂ CH ₂ CH ₂ -3 0 0
1088 Cl HH 6-Me, 2-CH ₂ CH ₂ CH ₂ -3 0 0
1089 Cl HH 6-Et, 2-CH ₂ CH ₂ CH ₂ -3 0 0
1090 Cl HH 6-iPr, 2-CH ₂ CH ₂ CH ₂ -3 0 0
1091 Cl HH 6-cPr, 2-CH ₂ CH ₂ CH ₂ -3 0 0
1092 Cl HH 6-CN, 2-CH ₂ CH ₂ CH ₂ -3 0 0
1093 Cl HH 6-OMe, 2-CH ₂ CH ₂ CH ₂ -3 0 0
1094 Cl HH 6-Cl, 2-OCH ₂ CH ₂ -3 0 0
1095 Cl HH 6-Br, 2-OCH ₂ CH ₂ -3 0 0
1096 Cl HH 6-Me, 2-OCH ₂ CH ₂ -3 0 0
1097 Cl HH 6-Et, 2-OCH ₂ CH ₂ -3 0 0
1098 Cl HH 6-cPr, 2-OCH ₂ CH ₂ -3 0 0
1099 Cl HH 6-Br, 2-OCH = CH-3 0 0
1100 Cl HH 6-Me, 2-OCH = CH-3 0 0
1101 Cl HH 6-Et, 2-OCH = CH-3 0 0
1102 Cl HH 6-cPr, 2-OCH = CH-3 0 0
1103 Cl HH 6-Cl, 2-CH ₂ CH ₂ O-3 0 0
1104 Cl HH 6-Br, 2-CH ₂ CH ₂ O-3 0 0
1105 Cl HH 6-Me, 2-CH ₂ CH ₂ O-3 0 0
1106 Cl HH 6-Et, 2-CH ₂ CH ₂ O-3 0 0
1107 Cl HH 6-cPr, 2-CH ₂ CH ₂ O-3 0 0
1108 Cl HH 6-Br, 2-CH = CHO-3 0 0
1109 Cl HH 6-Me, 2-CH = CHO-3 0 0
1110 Cl HH 6-Et, 2-CH = CHO-3 0 0
1111 Cl HH 6-cPr, 2-CH = CHO-3 0 0
1112 Cl HH 2,4,6-F _Three 0 0
1113 Cl HH 2,4-F ₂ , 6-Me 0 0
1114 Cl HH 2,4-F ₂ , 6-cPr 0 0
1115 Cl HH 2-F, 4,6-cPr ₂ 0 0
1116 Cl HH 2,4,6-Cl _Three 0 0
1117 Cl HH 2,4,6-Br _Three 0 0
1118 Cl HH 2,4-Br ₂ , 3,6-Me ₂ 0 0
1119 Cl HH 2-Br, 4,6-Me ₂ 0 0
1120 Cl HH 2,4-I ₂ , 6-Et 0 0
1121 Cl HH 2-Me, 4-F, 6-cPr 0 0
1122 Cl HH 2,4,6-Me _Three 0 0
1123 Cl HH 2,4-Me ₂ , 6-cPr 0 0
1124 Cl HH 2-Br, 3,5,6-Me _Three 0 0
1125 Cl HH 2,3,5,6-Me _Four 0 0
1126 Cl HH 2,3,5-Me _Three , 6-cPr 0 0
1127 Cl HH 2,3,5-Me _Three , 6-CN 0 0
1128 Cl HH 2,3,5-Me _Three , 6-OMe 0 0
1129 Cl HH 5,6-Me ₂ , 2-CH ₂ CH ₂ CH ₂ -3 0 0
1130 Cl HH 5-Me, 6-cPr, 2-CH ₂ CH ₂ CH ₂ -3 0 0
1131 Cl HH 5-Me, 6-CN, 2-CH ₂ CH ₂ CH ₂ -3 0 0
1132 Cl HH 5-Me, 6-OMe, 2-CH ₂ CH ₂ CH ₂ -3 0 0
1133 Cl HH 2-CH ₂ CH ₂ CH ₂ -3,5-CH ₂ CH ₂ CH ₂ -6 0 0
1134 Cl H COMe 2-F 0 0
1135 Cl H COMe 2-Cl 0 0
1136 Cl H COMe 2-Br 0 0
1137 Cl H COMe 2-I 0 0
1138 Cl H COMe 2-Me 0 0
1139 Cl H COMe 2-iPr 0 0
1140 Cl H COMe 2-cPr 0 0
1141 Cl H COMe 2-cBu 0 0
1142 Cl H COMe 2-CH ₂ CH ₂ CH ₂ -3 0 0
1143 Cl H COMe 2-cPr, 5-Me 0 0
1144 Cl H COMe 2-OMe, 5-Me 0 0
1145 Cl H COMe 2-F, 6-iPr 0 0
1146 Cl H COMe 2-Cl, 6-cPr 0 0
1147 Cl H COMe 2-Br, 6-Me 0 0
1148 Cl H COMe 2-I, 6-Me 0 0
1149 Cl H COMe 2,6-Me ₂ 0 0
1150 Cl H COMe 2-Me, 6-Et 0 0
1151 Cl H COMe 2-Me, 6-cPr 0 0
1152 Cl H COMe 2,6-cPr ₂ 0 0
1153 Cl H COMe 2-cPr, 3,5-Me ₂ 0 0
1154 Cl H COMe 2-cPr, 5,6-Me ₂ 0 0
1155 Cl H COEt 2-Me 0 0
1156 Cl H COEt 2-iPr 0 0
1157 Cl H COEt 2-cPr 0 0
1158 Cl H COEt 2-CH ₂ CH ₂ CH ₂ -3 0 0
1159 Cl H COEt 2,6-Me ₂ 0 0
1160 Cl H COEt 2-Me, 6-cPr 0 0
1161 Cl H COPr 2-Me 0 0
1162 Cl H COPr 2-iPr 0 0
1163 Cl H COPr 2-cPr 0 0
1164 Cl H COPr 2-CH ₂ CH ₂ CH ₂ -3 0 0
1165 Cl H COPr 2,6-Me ₂ 0 0
1166 Cl H COPr 2-Me, 6-cPr 0 0
1167 Cl H COiPr 2-Me 0 0
1168 Cl H COiPr 2-iPr 0 0
1169 Cl H COiPr 2-cPr 0 0
1170 Cl H COiPr 2-CH ₂ CH ₂ CH ₂ -3 0 0
1171 Cl H COiPr 2,6-Me ₂ 0 0
1172 Cl H COiPr 2-Me, 6-cPr 0 0
1173 Cl H COBu 2-Me 0 0
1174 Cl H COBu 2-iPr 0 0
1175 Cl H COBu 2-cPr 0 0
1176 Cl H COBu 2-CH ₂ CH ₂ CH ₂ -3 0 0
1177 Cl H COBu 2,6-Me ₂ 0 0
1178 Cl H COBu 2-Me, 6-cPr 0 0
1179 Cl H COiBu 2-Me 0 0
1180 Cl H COiBu 2-iPr 0 0
1181 Cl H COiBu 2-cPr 0 0
1182 Cl H COiBu 2-CH ₂ CH ₂ CH ₂ -3 0 0
1183 Cl H COiBu 2,6-Me ₂ 0 0
1184 Cl H COiBu 2-Me, 6-cPr 0 0
1185 Cl H COsBu 2-Me 0 0
1186 Cl H COsBu 2-iPr 0 0
1187 Cl H COsBu 2-cPr 0 0
1188 Cl H COsBu 2-CH ₂ CH ₂ CH ₂ -3 0 0
1189 Cl H COsBu 2,6-Me ₂ 0 0
1190 Cl H COsBu 2-Me, 6-cPr 0 0
1191 Cl H COtBu 2-Cl 0 0
1192 Cl H COtBu 2-Br 0 0
1193 Cl H COtBu 2-I 0 0
1194 Cl H COtBu 2-Me 0 0
1195 Cl H COtBu 2-iPr 0 0
1196 Cl H COtBu 2-cPr 0 0
1197 Cl H COtBu 2-cBu 0 0
1198 Cl H COtBu 2-CH ₂ CH ₂ CH ₂ -3 0 0
1199 Cl H COtBu 2-cPr, 5-Me 0 0
1200 Cl H COtBu 2-OMe, 5-Me 0 0
1201 Cl H COtBu 2-F, 6-iPr 0 0
1202 Cl H COtBu 2-Cl, 6-cPr 0 0
1203 Cl H COtBu 2-Br, 6-Me 0 0
1204 Cl H COtBu 2-I, 6-Me 0 0
1205 Cl H COtBu 2,6-Me ₂ 0 0
1206 Cl H COtBu 2-Me, 6-Et 0 0
1207 Cl H COtBu 2-Me, 6-cPr 0 0
1208 Cl H COtBu 2,6-cPr ₂ 0 0
1209 Cl H COtBu 2-cPr, 3,5-Me ₂ 0 0
1210 Cl H COtBu 2-cPr, 5,6-Me ₂ 0 0
1211 Cl H COtPen 2-Me 0 0
1212 Cl H COtPen 2-iPr 0 0
1213 Cl H COtPen 2-cPr 0 0
1214 Cl H COtPen 2-CH ₂ CH ₂ CH ₂ -3 0 0
1215 Cl H COtPen 2,6-Me ₂ 0 0
1216 Cl H COtPen 2-Me, 6-cPr 0 0
1217 Cl H COHx 2-Me 0 0
1218 Cl H COHx 2-iPr 0 0
1219 Cl H COHx 2-cPr 0 0
1220 Cl H COHx 2-CH ₂ CH ₂ CH ₂ -3 0 0
1221 Cl H COHx 2,6-Me ₂ 0 0
1222 Cl H COHx 2-Me, 6-cPr 0 0
1223 Cl H COC ₇ H ₁₅ 2-Me 0 0
1224 Cl H COC ₇ H ₁₅ 2-iPr 0 0
1225 Cl H COC ₇ H ₁₅ 2-cPr 0 0
1226 Cl H COC ₇ H ₁₅ 2-CH ₂ CH ₂ CH ₂ -3 0 0
1227 Cl H COC ₇ H ₁₅ 2,6-Me ₂ 0 0
1228 Cl H COC ₇ H ₁₅ 2-Me, 6-cPr 0 0
1229 Cl H COC ₈ H ₁₇ 2-Me 0 0
1230 Cl H COC ₈ H ₁₇ 2-iPr 0 0
1231 Cl H COC ₈ H ₁₇ 2-cPr 0 0
1232 Cl H COC ₈ H ₁₇ 2-CH ₂ CH ₂ CH ₂ -3 0 0
1233 Cl H COC ₈ H ₁₇ 2,6-Me ₂ 0 0
1234 Cl H COC ₈ H ₁₇ 2-Me, 6-cPr 0 0
1235 Cl H COC ₉ H ₁₉ 2-Cl 0 0
1236 Cl H COC ₉ H ₁₉ 2-Br 0 0
1237 Cl H COC ₉ H ₁₉ 2-I 0 0
1238 Cl H COC ₉ H ₁₉ 2-Me 0 0
1239 Cl H COC ₉ H ₁₉ 2-iPr 0 0
1240 Cl H COC ₉ H ₁₉ 2-cPr 0 0
1241 Cl H COC ₉ H ₁₉ 2-cBu 0 0
1242 Cl H COC ₉ H ₁₉ 2-CH ₂ CH ₂ CH ₂ -3 0 0
1243 Cl H COC ₉ H ₁₉ 2-cPr, 5-Me 0 0
1244 Cl H COC ₉ H ₁₉ 2-OMe, 5-Me 0 0
1245 Cl H COC ₉ H ₁₉ 2-F, 6-iPr 0 0
1246 Cl H COC ₉ H ₁₉ 2-Cl, 6-cPr 0 0
1247 Cl H COC ₉ H ₁₉ 2-Br, 6-Me 0 0
1248 Cl H COC ₉ H ₁₉ 2-I, 6-Me 0 0
1249 Cl H COC ₉ H ₁₉ 2,6-Me ₂ 0 0
1250 Cl H COC ₉ H ₁₉ 2-Me, 6-Et 0 0
1251 Cl H COC ₉ H ₁₉ 2-Me, 6-cPr 0 0
1252 Cl H COC ₉ H ₁₉ 2,6-cPr ₂ 0 0
1253 Cl H COC ₉ H ₁₉ 2-cPr, 3,5-Me ₂ 0 0
1254 Cl H COC ₉ H ₁₉ 2-cPr, 5,6-Me ₂ 0 0
1255 Cl H COC ₁₄ H ₂₉ 2-Me 0 0
1256 Cl H COC ₁₄ H ₂₉ 2-iPr 0 0
1257 Cl H COC ₁₄ H ₂₉ 2-cPr 0 0
1258 Cl H COC ₁₄ H ₂₉ 2-CH ₂ CH ₂ CH ₂ -3 0 0
1259 Cl H COC ₁₄ H ₂₉ 2,6-Me ₂ 0 0
1260 Cl H COC ₁₄ H ₂₉ 2-Me, 6-cPr 0 0
1261 Cl H COcPr 2-Cl 0 0
1262 Cl H COcPr 2-Br 0 0
1263 Cl H COcPr 2-I 0 0
1264 Cl H COcPr 2-Me 0 0
1265 Cl H COcPr 2-iPr 0 0
1266 Cl H COcPr 2-cPr 0 0
1267 Cl H COcPr 2-cBu 0 0
1268 Cl H COcPr 2-CH ₂ CH ₂ CH ₂ -3 0 0
1269 Cl H COcPr 2-cPr, 5-Me 0 0
1270 Cl H COcPr 2-OMe, 5-Me 0 0
1271 Cl H COcPr 2-F, 6-iPr 0 0
1272 Cl H COcPr 2-Cl, 6-cPr 0 0
1273 Cl H COcPr 2-Br, 6-Me 0 0
1274 Cl H COcPr 2-I, 6-Me 0 0
1275 Cl H COcPr 2,6-Me ₂ 0 0
1276 Cl H COcPr 2-Me, 6-Et 0 0
1277 Cl H COcPr 2-Me, 6-cPr 0 0
1278 Cl H COcPr 2,6-cPr ₂ 0 0
1279 Cl H COcPr 2-cPr, 3,5-Me ₂ 0 0
1280 Cl H COcPr 2-cPr, 5,6-Me ₂ 0 0
1281 Cl H COcBu 2-Me 0 0
1282 Cl H COcBu 2-iPr 0 0
1283 Cl H COcBu 2-cPr 0 0
1284 Cl H COcBu 2-CH ₂ CH ₂ CH ₂ -3 0 0
1285 Cl H COcBu 2,6-Me ₂ 0 0
1286 Cl H COcBu 2-Me, 6-cPr 0 0
1287 Cl H COcPen 2-Me 0 0
1288 Cl H COcPen 2-iPr 0 0
1289 Cl H COcPen 2-cPr 0 0
1290 Cl H COcPen 2-CH ₂ CH ₂ CH ₂ -3 0 0
1291 Cl H COcPen 2,6-Me ₂ 0 0
1292 Cl H COcPen 2-Me, 6-cPr 0 0
1293 Cl H COcHx 2-Me 0 0
1294 Cl H COcHx 2-iPr 0 0
1295 Cl H COcHx 2-cPr 0 0
1296 Cl H COcHx 2-CH ₂ CH ₂ CH ₂ -3 0 0
1297 Cl H COcHx 2,6-Me ₂ 0 0
1298 Cl H COcHx 2-Me, 6-cPr 0 0
1299 Cl H COCF _Three 2-Me 0 0
1300 Cl H COCF _Three 2-iPr 0 0
1301 Cl H COCF _Three 2-cPr 0 0
1302 Cl H COCF _Three 2-CH ₂ CH ₂ CH ₂ -3 0 0
1303 Cl H COCF _Three 2,6-Me ₂ 0 0
1304 Cl H COCF _Three 2-Me, 6-cPr 0 0
1305 Cl H COCH ₂ Cl 2-Me 0 0
1306 Cl H COCH ₂ Cl 2-iPr 0 0
1307 Cl H COCH ₂ Cl 2-cPr 0 0
1308 Cl H COCH ₂ Cl 2-CH ₂ CH ₂ CH ₂ -3 0 0
1309 Cl H COCH ₂ Cl 2,6-Me ₂ 0 0
1310 Cl H COCH ₂ Cl 2-Me, 6-cPr 0 0
1311 Cl H COCCl _Three 2-Me 0 0
1312 Cl H COCCl _Three 2-iPr 0 0
1313 Cl H COCCl _Three 2-cPr 0 0
1314 Cl H COCCl _Three 2-CH ₂ CH ₂ CH ₂ -3 0 0
1315 Cl H COCCl _Three 2,6-Me ₂ 0 0
1316 Cl H COCCl _Three 2-Me, 6-cPr 0 0
1317 Cl H COCH ₂ Br 2-Me 0 0
1318 Cl H COCH ₂ Br 2-iPr 0 0
1319 Cl H COCH ₂ Br 2-cPr 0 0
1320 Cl H COCH ₂ Br 2-CH ₂ CH ₂ CH ₂ -3 0 0
1321 Cl H COCH ₂ Br 2,6-Me ₂ 0 0
1322 Cl H COCH ₂ Br 2-Me, 6-cPr 0 0
1323 Cl H COCH ₂ CF _Three 2-Me 0 0
1324 Cl H COCH ₂ CF _Three 2-iPr 0 0
1325 Cl H COCH ₂ CF _Three 2-cPr 0 0
1326 Cl H COCH ₂ CF _Three 2-CH ₂ CH ₂ CH ₂ -3 0 0
1327 Cl H COCH ₂ CF _Three 2,6-Me ₂ 0 0
1328 Cl H COCH ₂ CF _Three 2-Me, 6-cPr 0 0
1329 Cl H COCHBrEt 2-Me 0 0
1330 Cl H COCHBrEt 2-iPr 0 0
1331 Cl H COCHBrEt 2-cPr 0 0
1332 Cl H COCHBrEt 2-CH ₂ CH ₂ CH ₂ -3 0 0
1333 Cl H COCHBrEt 2,6-Me ₂ 0 0
1334 Cl H COCHBrEt 2-Me, 6-cPr 0 0
1335 Cl H COCH ₂ CH ₂ CH ₂ Cl 2-Me 0 0
1336 Cl H COCH ₂ CH ₂ CH ₂ Cl 2-iPr 0 0
1337 Cl H COCH ₂ CH ₂ CH ₂ Cl 2-cPr 0 0
1338 Cl H COCH ₂ CH ₂ CH ₂ Cl 2-CH ₂ CH ₂ CH ₂ -3 0 0
1339 Cl H COCH ₂ CH ₂ CH ₂ Cl 2,6-Me ₂ 0 0
1340 Cl H COCH ₂ CH ₂ CH ₂ Cl 2-Me, 6-cPr 0 0
1341 Cl H COCH = CH ₂ 2-Me 0 0
1342 Cl H COCH = CH ₂ 2-iPr 0 0
1343 Cl H COCH = CH ₂ 2-cPr 0 0
1344 Cl H COCH = CH ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
1345 Cl H COCH = CH ₂ 2,6-Me ₂ 0 0
1346 Cl H COCH = CH ₂ 2-Me, 6-cPr 0 0
1347 Cl H COCH = CHMe 2-Me 0 0
1348 Cl H COCH = CHMe 2-iPr 0 0
1349 Cl H COCH = CHMe 2-cPr 0 0
1350 Cl H COCH = CHMe 2-CH ₂ CH ₂ CH ₂ -3 0 0
1351 Cl H COCH = CHMe 2,6-Me ₂ 0 0
1352 Cl H COCH = CHMe 2-Me, 6-cPr 0 0
1353 Cl H COCH = CMe ₂ 2-Me 0 0
1354 Cl H COCH = CMe ₂ 2-iPr 0 0
1355 Cl H COCH = CMe ₂ 2-cPr 0 0
1356 Cl H COCH = CMe ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
1357 Cl H COCH = CMe ₂ 2,6-Me ₂ 0 0
1358 Cl H COCH = CMe ₂ 2-Me, 6-cPr 0 0
1359 Cl H COCH = CHPh 2-Me 0 0
1360 Cl H COCH = CHPh 2-iPr 0 0
1361 Cl H COCH = CHPh 2-cPr 0 0
1362 Cl H COCH = CHPh 2-CH ₂ CH ₂ CH ₂ -3 0 0
1363 Cl H COCH = CHPh 2,6-Me ₂ 0 0
1364 Cl H COCH = CHPh 2-Me, 6-cPr 0 0
1365 Cl H COC≡CH 2-Me 0 0
1366 Cl H COC≡CH 2-iPr 0 0
1367 Cl H COC≡CH 2-cPr 0 0
1368 Cl H COC≡CH 2-CH ₂ CH ₂ CH ₂ -3 0 0
1369 Cl H COC≡CH 2,6-Me ₂ 0 0
1370 Cl H COC≡CH 2-Me, 6-cPr 0 0
1371 Cl H COCH ₂ Ph 2-Me 0 0
1372 Cl H COCH ₂ Ph 2-iPr 0 0
1373 Cl H COCH ₂ Ph 2-cPr 0 0
1374 Cl H COCH ₂ Ph 2-CH ₂ CH ₂ CH ₂ -3 0 0
1375 Cl H COCH ₂ Ph 2,6-Me ₂ 0 0
1376 Cl H COCH ₂ Ph 2-Me, 6-cPr 0 0
1377 Cl H COCH ₂ CH ₂ CO ₂ Me 2-Me 0 0
1378 Cl H COCH ₂ CH ₂ CO ₂ Me 2-iPr 0 0
1379 Cl H COCH ₂ CH ₂ CO ₂ Me 2-cPr 0 0
1380 Cl H COCH ₂ CH ₂ CO ₂ Me 2-CH ₂ CH ₂ CH ₂ -3 0 0
1381 Cl H COCH ₂ CH ₂ CO ₂ Me 2,6-Me ₂ 0 0
1382 Cl H COCH ₂ CH ₂ CO ₂ Me 2-Me, 6-cPr 0 0
1383 Cl H COPh 2-F 0 0
1384 Cl H COPh 2-Cl 0 0
1385 Cl H COPh 2-Br 0 0
1386 Cl H COPh 2-I 0 0
1387 Cl H COPh 2-Me 0 0
1388 Cl H COPh 2-Et 0 0
1389 Cl H COPh 2-iPr 0 0
1390 Cl H COPh 2-tBu 0 0
1391 Cl H COPh 2-cPr 0 0
1392 Cl H COPh 2- (cPr-1-Me) 0 0
1393 Cl H COPh 2- (cPr-2-Me) 0 0
1394 Cl H COPh 2- (cPr-2,2-Cl ₂ ) 0 0
1395 Cl H COPh 2-cBu 0 0
1396 Cl H COPh 4-SiMe _Three 0 0
1397 Cl H COPh 2-CH ₂ CH ₂ CH ₂ -3 0 0
1398 Cl H COPh 2-CH = CHO-3 0 0
1399 Cl H COPh 2-CH ₂ CH ₂ O-3 0 0
1400 Cl H COPh 2-OCH = CH-3 0 0
1401 Cl H COPh 2-OCH ₂ CH ₂ -3 0 0
1402 Cl H COPh 2-cPr, 5-F 0 0
1403 Cl H COPh 2-cPr, 5-Cl 0 0
1404 Cl H COPh 2-cPr, 5-Me 0 0
1405 Cl H COPh 2-OMe, 5-Me 0 0
1406 Cl H COPh 2-F, 6-iPr 0 0
1407 Cl H COPh 2-F, 6-cPr 0 0
1408 Cl H COPh 2-Cl, 6-Me 0 0
1409 Cl H COPh 2-Cl, 6-cPr 0 0
1410 Cl H COPh 2-Br, 6-Me 0 0
1411 Cl H COPh 2-Br, 6-Et 0 0
1412 Cl H COPh 2-Br, 6-cPr 0 0
1413 Cl H COPh 2-I, 6-Me 0 0
1414 Cl H COPh 2-I, 6-Et 0 0
1415 Cl H COPh 2,6-Me ₂ 0 0
1416 Cl H COPh 2-Me, 6-Et 0 0
1417 Cl H COPh 2-Me, 6-cPr 0 0
1418 Cl H COPh 2-Et, 6-cPr 0 0
1419 Cl H COPh 2-iPr, 6-cPr 0 0
1420 Cl H COPh 2-tBu, 6-cPr 0 0
1421 Cl H COPh 2,6-cPr ₂ 0 0
1422 Cl H COPh 2-cPr, 6-OMe 0 0
1423 Cl H COPh 2-Br, 3,6-Me ₂ 0 0
1424 Cl H COPh 2-cPr, 3,5-Me ₂ 0 0
1425 Cl H COPh 2-cPr, 4,6-Me ₂ 0 0
1426 Cl H COPh 2-Br, 5,6-Me ₂ 0 0
1427 Cl H COPh 2-cPr, 5,6-Me ₂ 0 0
1428 Cl H COPh 2-Br, 5-CH = CH-O-6 0 0
1429 Cl H COPh 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
1430 Cl H COPh 2-Me, 5-CH ₂ CH ₂ O-6 0 0
1431 Cl H COPh 2-Me, 5-CH = CH-O-6 0 0
1432 Cl H COPh 2-Et, 5-CH ₂ CH ₂ CH ₂ -6 0 0
1433 Cl H COPh 2-cPr, 5-CH ₂ CH ₂ CH ₂ -6 0 0
1434 Cl H COPh 2-cPr, 5-CH = CH-O-6 0 0
1435 Cl H COPh 2-Br, 3,5,6-Me _Three 0 0
1436 Cl H CO (Ph-2-Cl) 2-Me 0 0
1437 Cl H CO (Ph-2-Cl) 2-iPr 0 0
1438 Cl H CO (Ph-2-Cl) 2-cPr 0 0
1439 Cl H CO (Ph-2-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1440 Cl H CO (Ph-2-Cl) 2,6-Me ₂ 0 0
1441 Cl H CO (Ph-2-Cl) 2-Me, 6-cPr 0 0
1442 Cl H CO (Ph-2-Me) 2-F 0 0
1443 Cl H CO (Ph-2-Me) 2-Cl 0 0
1444 Cl H CO (Ph-2-Me) 2-Br 0 0
1445 Cl H CO (Ph-2-Me) 2-I 0 0
1446 Cl H CO (Ph-2-Me) 2-Me 0 0
1447 Cl H CO (Ph-2-Me) 2-Et 0 0
1448 Cl H CO (Ph-2-Me) 2-iPr 0 0
1449 Cl H CO (Ph-2-Me) 2-tBu 0 0
1450 Cl H CO (Ph-2-Me) 2-sBu 0 0
1451 Cl H CO (Ph-2-Me) 2- (cPr-1-Me) 0 0
1452 Cl H CO (Ph-2-Me) 2-cPr 0 0
1453 Cl H CO (Ph-2-Me) 2- (cPr-2,2-Cl ₂ ) 0 0
1454 Cl H CO (Ph-2-Me) 2-cBu 0 0
1455 Cl H CO (Ph-2-Me) 2-cHx 0 0
1456 Cl H CO (Ph-2-Me) 2-Ph 0 0
1457 Cl H CO (Ph-2-Me) 3-tBu 0 0
1458 Cl H CO (Ph-2-Me) 3-OMe 0 0
1459 Cl H CO (Ph-2-Me) 2-iPr, 5-Me 0 0
1460 Cl H CO (Ph-2-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1461 Cl H CO (Ph-2-Me) 2-CH = CHCH = CH-3 0 0
1462 Cl H CO (Ph-2-Me) 2-CH = CHO-3 0 0
1463 Cl H CO (Ph-2-Me) 2-CH ₂ CH ₂ O-3 0 0
1464 Cl H CO (Ph-2-Me) 2-OCH = CH-3 0 0
1465 Cl H CO (Ph-2-Me) 2-OCH ₂ CH ₂ -3 0 0
1466 Cl H CO (Ph-2-Me) 2-cPr, 5-F 0 0
1467 Cl H CO (Ph-2-Me) 2-cPr, 5-Cl 0 0
1468 Cl H CO (Ph-2-Me) 2-cPr, 5-Me 0 0
1469 Cl H CO (Ph-2-Me) 2-OMe, 5-Me 0 0
1470 Cl H CO (Ph-2-Me) 2-F, 6-iPr 0 0
1471 Cl H CO (Ph-2-Me) 2-F, 6-cPr 0 0
1472 Cl H CO (Ph-2-Me) 2-Cl, 6-Me 0 0
1473 Cl H CO (Ph-2-Me) 2-Cl, 6-cPr 0 0
1474 Cl H CO (Ph-2-Me) 2-Br, 6-Me 0 0
1475 Cl H CO (Ph-2-Me) 2-Br, 6-Et 0 0
1476 Cl H CO (Ph-2-Me) 2-Br, 6-cPr 0 0
1477 Cl H CO (Ph-2-Me) 2-I, 6-Me 0 0
1478 Cl H CO (Ph-2-Me) 2-I, 6-Et 0 0
1479 Cl H CO (Ph-2-Me) 2,6-Me ₂ 0 0
1480 Cl H CO (Ph-2-Me) 2-Me, 6-Et 0 0
1481 Cl H CO (Ph-2-Me) 2-Me, 6-cPr 0 0
1482 Cl H CO (Ph-2-Me) 2-Et, 6-cPr 0 0
1483 Cl H CO (Ph-2-Me) 2-iPr, 6-cPr 0 0
1484 Cl H CO (Ph-2-Me) 2-tBu, 6-cPr 0 0
1485 Cl H CO (Ph-2-Me) 2,6-cPr ₂ 0 0
1486 Cl H CO (Ph-2-Me) 2-cPr, 6-OMe 0 0
1487 Cl H CO (Ph-2-Me) 2-Br, 3,6-Me ₂ 0 0
1488 Cl H CO (Ph-2-Me) 2-cPr, 3,5-Me ₂ 0 0
1489 Cl H CO (Ph-2-Me) 2-cPr, 4,6-Me ₂ 0 0
1490 Cl H CO (Ph-2-Me) 2-Br, 5,6-Me ₂ 0 0
1491 Cl H CO (Ph-2-Me) 2-cPr, 5,6-Me ₂ 0 0
1492 Cl H CO (Ph-2-Me) 2-Br, 5-CH = CH-O-6 0 0
1493 Cl H CO (Ph-2-Me) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
1494 Cl H CO (Ph-2-Me) 2-Me, 5-CH ₂ CH ₂ O-6 0 0
1495 Cl H CO (Ph-2-Me) 2-Me, 5-CH = CH-O-6 0 0
1496 Cl H CO (Ph-2-Me) 2-Et, 5-CH ₂ CH ₂ CH ₂ -6 0 0
1497 Cl H CO (Ph-2-Me) 2-cPr, 5-CH ₂ CH ₂ CH ₂ -6 0 0
1498 Cl H CO (Ph-2-Me) 2-cPr, 5-CH = CH-O-6 0 0
1499 Cl H CO (Ph-2-Me) 2-Br, 3,5,6-Me _Three 0 0
1500 Cl H CO (Ph-2-CN) 2-Me 0 0
1501 Cl H CO (Ph-2-CN) 2-iPr 0 0
1502 Cl H CO (Ph-2-CN) 2-cPr 0 0
1503 Cl H CO (Ph-2-CN) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1504 Cl H CO (Ph-2-CN) 2,6-Me ₂ 0 0
1505 Cl H CO (Ph-2-CN) 2-Me, 6-cPr 0 0
1506 Cl H CO (Ph-2-OMe) 2-Cl 0 0
1507 Cl H CO (Ph-2-OMe) 2-Br 0 0
1508 Cl H CO (Ph-2-OMe) 2-I 0 0
1509 Cl H CO (Ph-2-OMe) 2-Me 0 0
1510 Cl H CO (Ph-2-OMe) 2-iPr 0 0
1511 Cl H CO (Ph-2-OMe) 2-cPr 0 0
1512 Cl H CO (Ph-2-OMe) 2-cBu 0 0
1513 Cl H CO (Ph-2-OMe) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1514 Cl H CO (Ph-2-OMe) 2-cPr, 5-Me 0 0
1515 Cl H CO (Ph-2-OMe) 2-OMe, 5-Me 0 0
1516 Cl H CO (Ph-2-OMe) 2-F, 6-iPr 0 0
1517 Cl H CO (Ph-2-OMe) 2-Cl, 6-cPr 0 0
1518 Cl H CO (Ph-2-OMe) 2-Br, 6-Me 0 0
1519 Cl H CO (Ph-2-OMe) 2-I, 6-Me 0 0
1520 Cl H CO (Ph-2-OMe) 2,6-Me ₂ 0 0
1521 Cl H CO (Ph-2-OMe) 2-Me, 6-Et 0 0
1522 Cl H CO (Ph-2-OMe) 2-Me, 6-cPr 0 0
1523 Cl H CO (Ph-2-OMe) 2,6-cPr ₂ 0 0
1524 Cl H CO (Ph-2-OMe) 2-cPr, 3,5-Me ₂ 0 0
1525 Cl H CO (Ph-2-OMe) 2-cPr, 5,6-Me ₂ 0 0
1526 Cl H CO (Ph-3-Me) 2-Me 0 0
1527 Cl H CO (Ph-3-Me) 2-iPr 0 0
1528 Cl H CO (Ph-3-Me) 2-cPr 0 0
1529 Cl H CO (Ph-3-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1530 Cl H CO (Ph-3-Me) 2,6-Me ₂ 0 0
1531 Cl H CO (Ph-3-Me) 2-Me, 6-cPr 0 0
1532 Cl H CO (Ph-4-Cl) 2-Me 0 0
1533 Cl H CO (Ph-4-Cl) 2-iPr 0 0
1534 Cl H CO (Ph-4-Cl) 2-cPr 0 0
1535 Cl H CO (Ph-4-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1536 Cl H CO (Ph-4-Cl) 2,6-Me ₂ 0 0
1537 Cl H CO (Ph-4-Cl) 2-Me, 6-cPr 0 0
1538 Cl H CO (Ph-4-Br) 2-Me 0 0
1539 Cl H CO (Ph-4-Br) 2-iPr 0 0
1540 Cl H CO (Ph-4-Br) 2-cPr 0 0
1541 Cl H CO (Ph-4-Br) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1542 Cl H CO (Ph-4-Br) 2,6-Me ₂ 0 0
1543 Cl H CO (Ph-4-Br) 2-Me, 6-cPr 0 0
1544 Cl H CO (Ph-4-I) 2-Me 0 0
1545 Cl H CO (Ph-4-I) 2-iPr 0 0
1546 Cl H CO (Ph-4-I) 2-cPr 0 0
1547 Cl H CO (Ph-4-I) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1548 Cl H CO (Ph-4-I) 2,6-Me ₂ 0 0
1549 Cl H CO (Ph-4-I) 2-Me, 6-cPr 0 0
1550 Cl H CO (Ph-4-Me) 2-Cl 0 0
1551 Cl H CO (Ph-4-Me) 2-Br 0 0
1552 Cl H CO (Ph-4-Me) 2-I 0 0
1553 Cl H CO (Ph-4-Me) 2-Me 0 0
1554 Cl H CO (Ph-4-Me) 2-iPr 0 0
1555 Cl H CO (Ph-4-Me) 2-cPr 0 0
1556 Cl H CO (Ph-4-Me) 2-cBu 0 0
1557 Cl H CO (Ph-4-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1558 Cl H CO (Ph-4-Me) 2-cPr, 5-Me 0 0
1559 Cl H CO (Ph-4-Me) 2-OMe, 5-Me 0 0
1560 Cl H CO (Ph-4-Me) 2-F, 6-iPr 0 0
1561 Cl H CO (Ph-4-Me) 2-Cl, 6-cPr 0 0
1562 Cl H CO (Ph-4-Me) 2-Br, 6-Me 0 0
1563 Cl H CO (Ph-4-Me) 2-I, 6-Me 0 0
1564 Cl H CO (Ph-4-Me) 2,6-Me ₂ 0 0
1565 Cl H CO (Ph-4-Me) 2-Me, 6-Et 0 0
1566 Cl H CO (Ph-4-Me) 2-Me, 6-cPr 0 0
1567 Cl H CO (Ph-4-Me) 2-cPr ₂ 0 0
1568 Cl H CO (Ph-4-Me) 2-cPr, 3,5-Me ₂ 0 0
1569 Cl H CO (Ph-4-Me) 2-cPr, 5,6-Me ₂ 0 0
1570 Cl H CO (Ph-4-tBu) 2-Me 0 0
1571 Cl H CO (Ph-4-tBu) 2-iPr 0 0
1572 Cl H CO (Ph-4-tBu) 2-cPr 0 0
1573 Cl H CO (Ph-4-tBu) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1574 Cl H CO (Ph-4-tBu) 2,6-Me ₂ 0 0
1575 Cl H CO (Ph-4-tBu) 2-Me, 6-cPr 0 0
1576 Cl H CO (Ph-4-CO ₂ Me) 2-Me 0 0
1577 Cl H CO (Ph-4-CO ₂ Me) 2-iPr 0 0
1578 Cl H CO (Ph-4-CO ₂ Me) 2-cPr 0 0
1579 Cl H CO (Ph-4-CO ₂ Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1580 Cl H CO (Ph-4-CO ₂ Me) 2,6-Me ₂ 0 0
1581 Cl H CO (Ph-4-CO ₂ Me) 2-Me, 6-cPr 0 0
1582 Cl H CO (Ph-4-COtBu) 2-Me 0 0
1583 Cl H CO (Ph-4-COtBu) 2-iPr 0 0
1584 Cl H CO (Ph-4-COtBu) 2-cPr 0 0
1585 Cl H CO (Ph-4-COtBu) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1586 Cl H CO (Ph-4-COtBu) 2,6-Me ₂ 0 0
1587 Cl H CO (Ph-4-COtBu) 2-Me, 6-cPr 0 0
1588 Cl H CO (Ph-4-NO ₂ ) 2-Me 0 0
1589 Cl H CO (Ph-4-NO ₂ ) 2-iPr 0 0
1590 Cl H CO (Ph-4-NO ₂ ) 2-cPr 0 0
1591 Cl H CO (Ph-4-NO ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1592 Cl H CO (Ph-4-NO ₂ ) 2,6-Me ₂ 0 0
1593 Cl H CO (Ph-4-NO ₂ ) 2-Me, 6-cPr 0 0
1594 Cl H CO (Ph-4-OMe) 2-Me 0 0
1595 Cl H CO (Ph-4-OMe) 2-iPr 0 0
1596 Cl H CO (Ph-4-OMe) 2-cPr 0 0
1597 Cl H CO (Ph-4-OMe) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1598 Cl H CO (Ph-4-OMe) 2,6-Me ₂ 0 0
1599 Cl H CO (Ph-4-OMe) 2-Me, 6-cPr 0 0
1600 Cl H CO (Ph-2,4-Cl ₂ ) 2-Cl 0 0
1601 Cl H CO (Ph-2,4-Cl ₂ ) 2-Br 0 0
1602 Cl H CO (Ph-2,4-Cl ₂ ) 2-I 0 0
1603 Cl H CO (Ph-2,4-Cl ₂ ) 2-Me 0 0
1604 Cl H CO (Ph-2,4-Cl ₂ ) 2-iPr 0 0
1605 Cl H CO (Ph-2,4-Cl ₂ ) 2-cPr 0 0
1606 Cl H CO (Ph-2,4-Cl ₂ ) 2-cBu 0 0
1607 Cl H CO (Ph-2,4-Cl ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1608 Cl H CO (Ph-2,4-Cl ₂ ) 2-cPr, 5-Me 0 0
1609 Cl H CO (Ph-2,4-Cl ₂ ) 2-OMe, 5-Me 0 0
1610 Cl H CO (Ph-2,4-Cl ₂ ) 2-F, 6-iPr 0 0
1611 Cl H CO (Ph-2,4-Cl ₂ ) 2-Cl, 6-cPr 0 0
1612 Cl H CO (Ph-2,4-Cl ₂ ) 2-Br, 6-Me 0 0
1613 Cl H CO (Ph-2,4-Cl ₂ ) 2-I, 6-Me 0 0
1614 Cl H CO (Ph-2,4-Cl ₂ ) 2,6-Me ₂ 0 0
1615 Cl H CO (Ph-2,4-Cl ₂ ) 2-Me, 6-Et 0 0
1616 Cl H CO (Ph-2,4-Cl ₂ ) 2-Me, 6-cPr 0 0
1617 Cl H CO (Ph-2,4-Cl ₂ ) 2,6-cPr ₂ 0 0
1618 Cl H CO (Ph-2,4-Cl ₂ ) 2-cPr, 3,5-Me ₂ 0 0
1619 Cl H CO (Ph-2,4-Cl ₂ ) 2-cPr, 5,6-Me ₂ 0 0
1620 Cl H CO (Ph-2-CO ₂ Q ^Five ) 2-Me 0 0
1621 Cl H CO (Ph-2-CO ₂ Q ^Five ) 2-iPr 0 0
1622 Cl H CO (Ph-2-CO ₂ Q ^Five ) 2-cPr 0 0
1623 Cl H CO (Ph-2-CO ₂ Q ^Five ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1624 Cl H CO (Ph-2-CO ₂ Q ^Five ) 2,6-Me ₂ 0 0
1625 Cl H CO (Ph-2-CO ₂ Q ^Five ) 2-Me, 6-cPr 0 0
1626 Cl H CO (Ph-3-CO ₂ Q ^Five ) 2-Me 0 0
1627 Cl H CO (Ph-3-CO ₂ Q ^Five ) 2-iPr 0 0
1628 Cl H CO (Ph-3-CO ₂ Q ^Five ) 2-cPr 0 0
1629 Cl H CO (Ph-3-CO ₂ Q ^Five ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1630 Cl H CO (Ph-3-CO ₂ Q ^Five ) 2,6-Me ₂ 0 0
1631 Cl H CO (Ph-3-CO ₂ Q ^Five ) 2-Me, 6-cPr 0 0
1632 Cl H CO (Ph-4-CO ₂ Q ^Five ) 2-Me 0 0
1633 Cl H CO (Ph-4-CO ₂ Q ^Five ) 2-iPr 0 0
1634 Cl H CO (Ph-4-CO ₂ Q ^Five ) 2-cPr 0 0
1635 Cl H CO (Ph-4-CO ₂ Q ^Five ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1636 Cl H CO (Ph-4-CO ₂ Q ^Five ) 2,6-Me ₂ 0 0
1637 Cl H CO (Ph-4-CO ₂ Q ^Five ) 2-Me, 6-cPr 0 0
1638 Cl H CO (2-Fur) 2-Me 0 0
1639 Cl H CO (2-Fur) 2-iPr 0 0
1640 Cl H CO (2-Fur) 2-cPr 0 0
1641 Cl H CO (2-Fur) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1642 Cl H CO (2-Fur) 2,6-Me ₂ 0 0
1643 Cl H CO (2-Fur) 2-Me, 6-cPr 0 0
1644 Cl H CO (2-Thi) 2-Me 0 0
1645 Cl H CO (2-Thi) 2-iPr 0 0
1646 Cl H CO (2-Thi) 2-cPr 0 0
1647 Cl H CO (2-Thi) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1648 Cl H CO (2-Thi) 2,6-Me ₂ 0 0
1649 Cl H CO (2-Thi) 2-Me, 6-cPr 0 0
1650 Cl H CO ₂ Me 2-F 0 0
1651 Cl H CO ₂ Me 2-Cl 0 0
1652 Cl H CO ₂ Me 2-Br 0 0
1653 Cl H CO ₂ Me 2-I 0 0
1654 Cl H CO ₂ Me 2-Me 0 0
1655 Cl H CO ₂ Me 2-Et 0 0
1656 Cl H CO ₂ Me 2-iPr 0 0
1657 Cl H CO ₂ Me 2-tBu 0 0
1658 Cl H CO ₂ Me 2-cPr 0 0
1659 Cl H CO ₂ Me 2- (cPr-1-Me) 0 0
1660 Cl H CO ₂ Me 2- (cPr-2-Me) 0 0
1661 Cl H CO ₂ Me 2- (cPr-2,2-Cl ₂ ) 0 0
1662 Cl H CO ₂ Me 2-cBu 0 0
1663 Cl H CO ₂ Me 2-CH ₂ CH ₂ CH ₂ -3 0 0
1664 Cl H CO ₂ Me 2-CH = CH-O-3 0 0
1665 Cl H CO ₂ Me 2-CH ₂ CH ₂ O-3 0 0
1666 Cl H CO ₂ Me 2-OCH = CH-3 0 0
1667 Cl H CO ₂ Me 2-OCH ₂ CH ₂ -3 0 0
1668 Cl H CO ₂ Me 2-cPr, 5-F 0 0
1669 Cl H CO ₂ Me 2-cPr, 5-Cl 0 0
1670 Cl H CO ₂ Me 2-cPr, 5-Me 0 0
1671 Cl H CO ₂ Me 2-OMe, 5-Me 0 0
1672 Cl H CO ₂ Me 2-F, 6-iPr 0 0
1673 Cl H CO ₂ Me 2-F, 6-cPr 0 0
1674 Cl H CO ₂ Me 2-Cl, 6-Me 0 0
1675 Cl H CO ₂ Me 2-Cl, 6-cPr 0 0
1676 Cl H CO ₂ Me 2-Br, 6-Me 0 0
1677 Cl H CO ₂ Me 2-Br, 6-Et 0 0
1678 Cl H CO ₂ Me 2-Br, 6-cPr 0 0
1679 Cl H CO ₂ Me 2-I, 6-Me 0 0
1680 Cl H CO ₂ Me 2-I, 6-Et 0 0
1681 Cl H CO ₂ Me 2,6-Me ₂ 0 0
1682 Cl H CO ₂ Me 2-Me, 6-Et 0 0
1683 Cl H CO ₂ Me 2-Me, 6-cPr 0 0
1684 Cl H CO ₂ Me 2-Et, 6-cPr 0 0
1685 Cl H CO ₂ Me 2-iPr, 6-cPr 0 0
1686 Cl H CO ₂ Me 2-tBu, 6-cPr 0 0
1687 Cl H CO ₂ Me 2,6-cPr ₂ 0 0
1688 Cl H CO ₂ Me 2-cPr, 6-OMe 0 0
1689 Cl H CO ₂ Me 2-Br, 3,6-Me ₂ 0 0
1690 Cl H CO ₂ Me 2-cPr, 3,5-Me ₂ 0 0
1691 Cl H CO ₂ Me 2-cPr, 4,6-Me ₂ 0 0
1692 Cl H CO ₂ Me 2-Br, 5,6-Me ₂ 0 0
1693 Cl H CO ₂ Me 2-cPr, 5,6-Me ₂ 0 0
1694 Cl H CO ₂ Me 2-Br, 5-CH = CH-O-6 0 0
1695 Cl H CO ₂ Me 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
1696 Cl H CO ₂ Me 2-Me, 5-CH ₂ CH ₂ O-6 0 0
1697 Cl H CO ₂ Me 2-Me, 5-CH = CH-O-6 0 0
1698 Cl H CO ₂ Me 2-Et, 5-CH ₂ CH ₂ CH ₂ -6 0 0
1699 Cl H CO ₂ Me 2-cPr, 5-CH ₂ CH ₂ CH ₂ -6 0 0
1700 Cl H CO ₂ Me 2-cPr, 5-CH = CH-O-6 0 0
1701 Cl H CO ₂ Me 2-Br, 3,5,6-Me _Three 0 0
1702 Cl H CO ₂ Et 2-F 0 0
1703 Cl H CO ₂ Et 2-Cl 0 0
1704 Cl H CO ₂ Et 2-Br 0 0
1705 Cl H CO ₂ Et 2-I 0 0
1706 Cl H CO ₂ Et 2-Me 0 0
1707 Cl H CO ₂ Et 2-Et 0 0
1708 Cl H CO ₂ Et 2-iPr 0 0
1709 Cl H CO ₂ Et 2-tBu 0 0
1710 Cl H CO ₂ Et 2-cPr 0 0
1711 Cl H CO ₂ Et 2- (cPr-1-Me) 0 0
1712 Cl H CO ₂ Et 2- (cPr-2-Me) 0 0
1713 Cl H CO ₂ Et 2- (cPr-2,2-Cl ₂ ) 0 0
1714 Cl H CO ₂ Et 2-cBu 0 0
1715 Cl H CO ₂ Et 2-CH ₂ CH ₂ CH ₂ -3 0 0
1716 Cl H CO ₂ Et 2-CH = CH-O-3 0 0
1717 Cl H CO ₂ Et 2-CH ₂ CH ₂ O-3 0 0
1718 Cl H CO ₂ Et 2-OCH = CH-3 0 0
1719 Cl H CO ₂ Et 2-OCH ₂ CH ₂ -3 0 0
1720 Cl H CO ₂ Et 2-cPr, 5-F 0 0
1721 Cl H CO ₂ Et 2-cPr, 5-Cl 0 0
1722 Cl H CO ₂ Et 2-cPr, 5-Me 0 0
1723 Cl H CO ₂ Et 2-OMe, 5-Me 0 0
1724 Cl H CO ₂ Et 2-F, 6-iPr 0 0
1725 Cl H CO ₂ Et 2-F, 6-cPr 0 0
1726 Cl H CO ₂ Et 2-Cl, 6-Me 0 0
1727 Cl H CO ₂ Et 2-Cl, 6-cPr 0 0
1728 Cl H CO ₂ Et 2-Br, 6-Me 0 0
1729 Cl H CO ₂ Et 2-Br, 6-Et 0 0
1730 Cl H CO ₂ Et 2-Br, 6-cPr 0 0
1731 Cl H CO ₂ Et 2-I, 6-Me 0 0
1732 Cl H CO ₂ Et 2-I, 6-Et 0 0
1733 Cl H CO ₂ Et 2,6-Me ₂ 0 0
1734 Cl H CO ₂ Et 2-Me, 6-Et 0 0
1735 Cl H CO ₂ Et 2-Me, 6-cPr 0 0
1736 Cl H CO ₂ Et 2-Et, 6-cPr 0 0
1737 Cl H CO ₂ Et 2-iPr, 6-cPr 0 0
1738 Cl H CO ₂ Et 2-tBu, 6-cPr 0 0
1739 Cl H CO ₂ Et 2,6-cPr ₂ 0 0
1740 Cl H CO ₂ Et 2-cPr, 6-OMe 0 0
1741 Cl H CO ₂ Et 2-Br, 3,6-Me ₂ 0 0
1742 Cl H CO ₂ Et 2-cPr, 3,5-Me ₂ 0 0
1743 Cl H CO ₂ Et 2-cPr, 4,6-Me ₂ 0 0
1744 Cl H CO ₂ Et 2-Br, 5,6-Me ₂ 0 0
1745 Cl H CO ₂ Et 2-cPr, 5,6-Me ₂ 0 0
1746 Cl H CO ₂ Et 2-Br, 5-CH = CH-O-6 0 0
1747 Cl H CO ₂ Et 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
1748 Cl H CO ₂ Et 2-Me, 5-CH ₂ CH ₂ O-6 0 0
1749 Cl H CO ₂ Et 2-Me, 5-CH = CH-O-6 0 0
1750 Cl H CO ₂ Et 2-Et, 5-CH ₂ CH ₂ CH ₂ -6 0 0
1751 Cl H CO ₂ Et 2-cPr, 5-CH ₂ CH ₂ CH ₂ -6 0 0
1752 Cl H CO ₂ Et 2-cPr, 5-CH = CH-O-6 0 0
1753 Cl H CO ₂ Et 2-Br, 3,5,6-Me _Three 0 0
1754 Cl H CO ₂ iBu 2-Cl 0 0
1755 Cl H CO ₂ iBu 2-Br 0 0
1756 Cl H CO ₂ iBu 2-I 0 0
1757 Cl H CO ₂ iBu 2-Me 0 0
1758 Cl H CO ₂ iBu 2-iPr 0 0
1759 Cl H CO ₂ iBu 2-cPr 0 0
1760 Cl H CO ₂ iBu 2-cBu 0 0
1761 Cl H CO ₂ iBu 2-CH ₂ CH ₂ CH ₂ -3 0 0
1762 Cl H CO ₂ iBu 2-cPr, 5-Me 0 0
1763 Cl H CO ₂ iBu 2-OMe, 5-Me 0 0
1764 Cl H CO ₂ iBu 2-F, 6-iPr 0 0
1765 Cl H CO ₂ iBu 2-Cl, 6-cPr 0 0
1766 Cl H CO ₂ iBu 2-Br, 6-Me 0 0
1767 Cl H CO ₂ iBu 2-I, 6-Me 0 0
1768 Cl H CO ₂ iBu 2,6-Me ₂ 0 0
1769 Cl H CO ₂ iBu 2-Me, 6-Et 0 0
1770 Cl H CO ₂ iBu 2-Me, 6-cPr 0 0
1771 Cl H CO ₂ iBu 2,6-cPr ₂ 0 0
1772 Cl H CO ₂ iBu 2-cPr, 3,5-Me ₂ 0 0
1773 Cl H CO ₂ iBu 2-cPr, 5,6-Me ₂ 0 0
1774 Cl H CO ₂ Bu 2-Me 0 0
1775 Cl H CO ₂ Bu 2-iPr 0 0
1776 Cl H CO ₂ Bu 2-cPr 0 0
1777 Cl H CO ₂ Bu 2-CH ₂ CH ₂ CH ₂ -3 0 0
1778 Cl H CO ₂ Bu 2,6-Me ₂ 0 0
1779 Cl H CO ₂ Bu 2-Me, 6-cPr 0 0
1780 Cl H CO ₂ CH ₂ Cl 2-Me 0 0
1781 Cl H CO ₂ CH ₂ Cl 2-iPr 0 0
1782 Cl H CO ₂ CH ₂ Cl 2-cPr 0 0
1783 Cl H CO ₂ CH ₂ Cl 2-CH ₂ CH ₂ CH ₂ -3 0 0
1784 Cl H CO ₂ CH ₂ Cl 2,6-Me ₂ 0 0
1785 Cl H CO ₂ CH ₂ Cl 2-Me, 6-cPr 0 0
1786 Cl H CO ₂ CH ₂ CCl _Three 2-Cl 0 0
1787 Cl H CO ₂ CH ₂ CCl _Three 2-Br 0 0
1788 Cl H CO ₂ CH ₂ CCl _Three 2-I 0 0
1789 Cl H CO ₂ CH ₂ CCl _Three 2-Me 0 0
1790 Cl H CO ₂ CH ₂ CCl _Three 2-iPr 0 0
1791 Cl H CO ₂ CH ₂ CCl _Three 2-cPr 0 0
1792 Cl H CO ₂ CH ₂ CCl _Three 2-cBu 0 0
1793 Cl H CO ₂ CH ₂ CCl _Three 2-CH ₂ CH ₂ CH ₂ -3 0 0
1794 Cl H CO ₂ CH ₂ CCl _Three 2-cPr, 5-Me 0 0
1795 Cl H CO ₂ CH ₂ CCl _Three 2-OMe, 5-Me 0 0
1796 Cl H CO ₂ CH ₂ CCl _Three 2-F, 6-iPr 0 0
1797 Cl H CO ₂ CH ₂ CCl _Three 2-Cl, 6-cPr 0 0
1798 Cl H CO ₂ CH ₂ CCl _Three 2-Br, 6-Me 0 0
1799 Cl H CO ₂ CH ₂ CCl _Three 2-I, 6-Me 0 0
1800 Cl H CO ₂ CH ₂ CCl _Three 2,6-Me ₂ 0 0
1801 Cl H CO ₂ CH ₂ CCl _Three 2-Me, 6-Et 0 0
1802 Cl H CO ₂ CH ₂ CCl _Three 2-Me, 6-cPr 0 0
1803 Cl H CO ₂ CH ₂ CCl _Three 2,6-cPr ₂ 0 0
1804 Cl H CO ₂ CH ₂ CCl _Three 2-cPr, 3,5-Me ₂ 0 0
1805 Cl H CO ₂ CH ₂ CCl _Three 2-cPr, 5,6-Me ₂ 0 0
1806 Cl H CO ₂ CH ₂ CH = CH ₂ 2-Me 0 0
1807 Cl H CO ₂ CH ₂ CH = CH ₂ 2-iPr 0 0
1808 Cl H CO ₂ CH ₂ CH = CH ₂ 2-cPr 0 0
1809 Cl H CO ₂ CH ₂ CH = CH ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
1810 Cl H CO ₂ CH ₂ CH = CH ₂ 2,6-Me ₂ 0 0
1811 Cl H CO ₂ CH ₂ CH = CH ₂ 2-Me, 6-cPr 0 0
1812 Cl H CO ₂ CH ₂ Ph 2-Me 0 0
1813 Cl H CO ₂ CH ₂ Ph 2-iPr 0 0
1814 Cl H CO ₂ CH ₂ Ph 2-cPr 0 0
1815 Cl H CO ₂ CH ₂ Ph 2-CH ₂ CH ₂ CH ₂ -3 0 0
1816 Cl H CO ₂ CH ₂ Ph 2,6-Me ₂ 0 0
1817 Cl H CO ₂ CH ₂ Ph 2-Me, 6-cPr 0 0
1818 Cl H CO ₂ CH ₂ CH ₂ OMe 2-Me 0 0
1819 Cl H CO ₂ CH ₂ CH ₂ OMe 2-iPr 0 0
1820 Cl H CO ₂ CH ₂ CH ₂ OMe 2-cPr 0 0
1821 Cl H CO ₂ CH ₂ CH ₂ OMe 2-CH ₂ CH ₂ CH ₂ -3 0 0
1822 Cl H CO ₂ CH ₂ CH ₂ OMe 2,6-Me ₂ 0 0
1823 Cl H CO ₂ CH ₂ CH ₂ OMe 2-Me, 6-cPr 0 0
1824 Cl H CO ₂ Ph 2-Cl 0 0
1825 Cl H CO ₂ Ph 2-Br 0 0
1826 Cl H CO ₂ Ph 2-I 0 0
1827 Cl H CO ₂ Ph 2-Me 0 0
1828 Cl H CO ₂ Ph 2-iPr 0 0
1829 Cl H CO ₂ Ph 2-cPr 0 0
1830 Cl H CO ₂ Ph 2-cBu 0 0
1831 Cl H CO ₂ Ph 2-CH ₂ CH ₂ CH ₂ -3 0 0
1832 Cl H CO ₂ Ph 2-cPr, 5-Me 0 0
1833 Cl H CO ₂ Ph 2-OMe, 5-Me 0 0
1834 Cl H CO ₂ Ph 2-F, 6-iPr 0 0
1835 Cl H CO ₂ Ph 2-Cl, 6-cPr 0 0
1836 Cl H CO ₂ Ph 2-Br, 6-Me 0 0
1837 Cl H CO ₂ Ph 2-I, 6-Me 0 0
1838 Cl H CO ₂ Ph 2,6-Me ₂ 0 0
1839 Cl H CO ₂ Ph 2-Me, 6-Et 0 0
1840 Cl H CO ₂ Ph 2-Me, 6-cPr 0 0
1841 Cl H CO ₂ Ph 2,6-cPr ₂ 0 0
1842 Cl H CO ₂ Ph 2-cPr, 3,5-Me ₂ 0 0
1843 Cl H CO ₂ Ph 2-cPr, 5,6-Me ₂ 0 0
1844 Cl H CO ₂ (Ph-4-Cl) 2-Me 0 0
1845 Cl H CO ₂ (Ph-4-Cl) 2-iPr 0 0
1846 Cl H CO ₂ (Ph-4-Cl) 2-cPr 0 0
1847 Cl H CO ₂ (Ph-4-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1848 Cl H CO ₂ (Ph-4-Cl) 2,6-Me ₂ 0 0
1849 Cl H CO ₂ (Ph-4-Cl) 2-Me, 6-cPr 0 0
1850 Cl H CO ₂ (Ph-4-NO ₂ ) 2-Me 0 0
1851 Cl H CO ₂ (Ph-4-NO ₂ ) 2-iPr 0 0
1852 Cl H CO ₂ (Ph-4-NO ₂ ) 2-cPr 0 0
1853 Cl H CO ₂ (Ph-4-NO ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1854 Cl H CO ₂ (Ph-4-NO ₂ ) 2,6-Me ₂ 0 0
1855 Cl H CO ₂ (Ph-4-NO ₂ ) 2-Me, 6-cPr 0 0
1856 Cl H CO ₂ (1-Np) 2-Me 0 0
1857 Cl H CO ₂ (1-Np) 2-iPr 0 0
1858 Cl H CO ₂ (1-Np) 2-cPr 0 0
1859 Cl H CO ₂ (1-Np) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1860 Cl H CO ₂ (1-Np) 2,6-Me ₂ 0 0
1861 Cl H CO ₂ (1-Np) 2-Me, 6-cPr 0 0
1862 Cl H CO ₂ (9-Q ^Four ) 2-Me 0 0
1863 Cl H CO ₂ (9-Q ^Four ) 2-iPr 0 0
1864 Cl H CO ₂ (9-Q ^Four ) 2-cPr 0 0
1865 Cl H CO ₂ (9-Q ^Four ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
1866 Cl H CO ₂ (9-Q ^Four ) 2,6-Me ₂ 0 0
1867 Cl H CO ₂ (9-Q ^Four ) 2-Me, 6-cPr 0 0
1868 Cl H CO ₂ Q ^Five 2-Me 0 0
1869 Cl H CO ₂ Q ^Five 2-iPr 0 0
1870 Cl H CO ₂ Q ^Five 2-cPr 0 0
1871 Cl H CO ₂ Q ^Five 2-CH ₂ CH ₂ CH ₂ -3 0 0
1872 Cl H CO ₂ Q ^Five 2,6-Me ₂ 0 0
1873 Cl H CO ₂ Q ^Five 2-Me, 6-cPr 0 0
1874 Cl H CONMe ₂ 2-Cl 0 0
1875 Cl H CONMe ₂ 2-Br 0 0
1876 Cl H CONMe ₂ 2-I 0 0
1877 Cl H CONMe ₂ 2-Me 0 0
1878 Cl H CONMe ₂ 2-iPr 0 0
1879 Cl H CONMe ₂ 2-cPr 0 0
1880 Cl H CONMe ₂ 2-cBu 0 0
1881 Cl H CONMe ₂ 3-CF _Three 0 0
1882 Cl H CONMe ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
1883 Cl H CONMe ₂ 2-cPr, 5-Me 0 0
1884 Cl H CONMe ₂ 2-OMe, 5-Me 0 0
1885 Cl H CONMe ₂ 2-F, 6-iPr 0 0
1886 Cl H CONMe ₂ 2-Cl, 6-cPr 0 0
1887 Cl H CONMe ₂ 2-Br, 6-Me 0 0
1888 Cl H CONMe ₂ 2-I, 6-Me 0 0
1889 Cl H CONMe ₂ 2,6-Me ₂ 0 0
1890 Cl H CONMe ₂ 2-Me, 6-Et 0 0
1891 Cl H CONMe ₂ 2-Me, 6-cPr 0 0
1892 Cl H CONMe ₂ 2,6-cPr ₂ 0 0
1893 Cl H CONMe ₂ 2-cPr, 3,5-Me ₂ 0 0
1894 Cl H CONMe ₂ 2-cPr, 5,6-Me ₂ 0 0
1895 Cl H CONEt ₂ 2-Cl 0 0
1896 Cl H CONEt ₂ 2-Br 0 0
1897 Cl H CONEt ₂ 2-I 0 0
1898 Cl H CONEt ₂ 2-Me 0 0
1899 Cl H CONEt ₂ 2-iPr 0 0
1900 Cl H CONEt ₂ 2-cPr 0 0
1901 Cl H CONEt ₂ 2-cBu 0 0
1902 Cl H CONEt ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
1903 Cl H CONEt ₂ 2-cPr, 5-Me 0 0
1904 Cl H CONEt ₂ 2-OMe, 5-Me 0 0
1905 Cl H CONEt ₂ 2-F, 6-iPr 0 0
1906 Cl H CONEt ₂ 2-Cl, 6-cPr 0 0
1907 Cl H CONEt ₂ 2-Br, 6-Me 0 0
1908 Cl H CONEt ₂ 2-I, 6-Me 0 0
1909 Cl H CONEt ₂ 2,6-Me ₂ 0 0
1910 Cl H CONEt ₂ 2-Me, 6-Et 0 0
1911 Cl H CONEt ₂ 2-Me, 6-cPr 0 0
1912 Cl H CONEt ₂ 2,6-cPr ₂ 0 0
1913 Cl H CONEt ₂ 2-cPr, 3,5-Me ₂ 0 0
1914 Cl H CONEt ₂ 2-cPr, 5,6-Me ₂ 0 0
1915 Cl H CON (iPr) ₂ 2-Me 0 0
1916 Cl H CON (iPr) ₂ 2-iPr 0 0
1917 Cl H CON (iPr) ₂ 2-cPr 0 0
1918 Cl H CON (iPr) ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
1919 Cl H CON (iPr) ₂ 2,6-Me ₂ 0 0
1920 Cl H CON (iPr) ₂ 2-Me, 6-cPr 0 0
1921 Cl H CO-1-Pyrd 2-Cl 0 0
1922 Cl H CO-1-Pyrd 2-Br 0 0
1923 Cl H CO-1-Pyrd 2-I 0 0
1924 Cl H CO-1-Pyrd 2-Me 0 0
1925 Cl H CO-1-Pyrd 2-iPr 0 0
1926 Cl H CO-1-Pyrd 2-cPr 0 0
1927 Cl H CO-1-Pyrd 2-cBu 0 0
1928 Cl H CO-1-Pyrd 2-CH ₂ CH ₂ CH ₂ -3 0 0
1929 Cl H CO-1-Pyrd 2-cPr, 5-Me 0 0
1930 Cl H CO-1-Pyrd 2-OMe, 5-Me 0 0
1931 Cl H CO-1-Pyrd 2-F, 6-iPr 0 0
1932 Cl H CO-1-Pyrd 2-Cl, 6-cPr 0 0
1933 Cl H CO-1-Pyrd 2-Br, 6-Me 0 0
1934 Cl H CO-1-Pyrd 2-I, 6-Me 0 0
1935 Cl H CO-1-Pyrd 2,6-Me ₂ 0 0
1936 Cl H CO-1-Pyrd 2-Me, 6-Et 0 0
1937 Cl H CO-1-Pyrd 2-Me, 6-cPr 0 0
1938 Cl H CO-1-Pyrd 2,6-cPr ₂ 0 0
1939 Cl H CO-1-Pyrd 2-cPr, 3,5-Me ₂ 0 0
1940 Cl H CO-1-Pyrd 2-cPr, 5,6-Me ₂ 0 0
1941 Cl H CONMePh 2-Me 0 0
1942 Cl H CONMePh 2-iPr 0 0
1943 Cl H CONMePh 2-cPr 0 0
1944 Cl H CONMePh 2-CH ₂ CH ₂ CH ₂ -3 0 0
1945 Cl H CONMePh 2,6-Me ₂ 0 0
1946 Cl H CONMePh 2-Me, 6-cPr 0 0
1947 Cl H CONPh ₂ 2-Me 0 0
1948 Cl H CONPh ₂ 2-iPr 0 0
1949 Cl H CONPh ₂ 2-cPr 0 0
1950 Cl H CONPh ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
1951 Cl H CONPh ₂ 2,6-Me ₂ 0 0
1952 Cl H CONPh ₂ 2-Me, 6-cPr 0 0
1953 Cl H COSMe 2-Me 0 0
1954 Cl H COSMe 2-iPr 0 0
1955 Cl H COSMe 2-cPr 0 0
1956 Cl H COSMe 2-CH ₂ CH ₂ CH ₂ -3 0 0
1957 Cl H COSMe 2,6-Me ₂ 0 0
1958 Cl H COSMe 2-Me, 6-cPr 0 0
1959 Cl H COSC ₇ H ₁₅ 2-Me 0 0
1960 Cl H COSC ₇ H ₁₅ 2-iPr 0 0
1961 Cl H COSC ₇ H ₁₅ 2-cPr 0 0
1962 Cl H COSC ₇ H ₁₅ 2-CH ₂ CH ₂ CH ₂ -3 0 0
1963 Cl H COSC ₇ H ₁₅ 2,6-Me ₂ 0 0
1964 Cl H COSC ₇ H ₁₅ 2-Me, 6-cPr 0 0
1965 Cl H COScHx 2-Me 0 0
1966 Cl H COScHx 2-iPr 0 0
1967 Cl H COScHx 2-cPr 0 0
1968 Cl H COScHx 2-CH ₂ CH ₂ CH ₂ -3 0 0
1969 Cl H COScHx 2,6-Me ₂ 0 0
1970 Cl H COScHx 2-Me, 6-cPr 0 0
1971 Cl H COSPh 2-Me 0 0
1972 Cl H COSPh 2-iPr 0 0
1973 Cl H COSPh 2-cPr 0 0
1974 Cl H COSPh 2-CH ₂ CH ₂ CH ₂ -3 0 0
1975 Cl H COSPh 2,6-Me ₂ 0 0
1976 Cl H COSPh 2-Me, 6-cPr 0 0
1977 Cl H SO ₂ Me 2-F 0 0
1978 Cl H SO ₂ Me 2-Cl 0 0
1979 Cl H SO ₂ Me 2-Br 0 0
1980 Cl H SO ₂ Me 2-I 0 0
1981 Cl H SO ₂ Me 2-Me 0 0
1982 Cl H SO ₂ Me 2-Et 0 0
1983 Cl H SO ₂ Me 2-iPr 0 0
1984 Cl H SO ₂ Me 2-tBu 0 0
1985 Cl H SO ₂ Me 2-cPr 0 0
1986 Cl H SO ₂ Me 2- (cPr-1-Me) 0 0
1987 Cl H SO ₂ Me 2- (cPr-2-Me) 0 0
1988 Cl H SO ₂ Me 2- (cPr-2,2-Cl ₂ ) 0 0
1989 Cl H SO ₂ Me 2-cBu 0 0
1990 Cl H SO ₂ Me 2-CH ₂ CH ₂ CH ₂ -3 0 0
1991 Cl H SO ₂ Me 2-CH = CH-O-3 0 0
1992 Cl H SO ₂ Me 2-CH ₂ CH ₂ O-3 0 0
1993 Cl H SO ₂ Me 2-OCH = CH-3 0 0
1994 Cl H SO ₂ Me 2-OCH ₂ CH ₂ -3 0 0
1995 Cl H SO ₂ Me 2-cPr, 5-F 0 0
1996 Cl H SO ₂ Me 2-cPr, 5-Cl 0 0
1997 Cl H SO ₂ Me 2-cPr, 5-Me 0 0
1998 Cl H SO ₂ Me 2-OMe, 5-Me 0 0
1999 Cl H SO ₂ Me 2-F, 6-iPr 0 0
2000 Cl H SO ₂ Me 2-F, 6-cPr 0 0
2001 Cl H SO ₂ Me 2-Cl, 6-Me 0 0
2002 Cl H SO ₂ Me 2-Cl, 6-cPr 0 0
2003 Cl H SO ₂ Me 2-Br, 6-Me 0 0
2004 Cl H SO ₂ Me 2-Br, 6-Et 0 0
2005 Cl H SO ₂ Me 2-Br, 6-cPr 0 0
2006 Cl H SO ₂ Me 2-I, 6-Me 0 0
2007 Cl H SO ₂ Me 2-I, 6-Et 0 0
2008 Cl H SO ₂ Me 2,6-Me ₂ 0 0
2009 Cl H SO ₂ Me 2-Me, 6-Et 0 0
2010 Cl H SO ₂ Me 2-Me, 6-cPr 0 0
2011 Cl H SO ₂ Me 2-Et, 6-cPr 0 0
2012 Cl H SO ₂ Me 2-iPr, 6-cPr 0 0
2013 Cl H SO ₂ Me 2-tBu, 6-cPr 0 0
2014 Cl H SO ₂ Me 2,6-cPr ₂ 0 0
2015 Cl H SO ₂ Me 2-cPr, 6-OMe 0 0
2016 Cl H SO ₂ Me 2-Br, 3,6-Me ₂ 0 0
2017 Cl H SO ₂ Me 2-cPr, 3,5-Me ₂ 0 0
2018 Cl H SO ₂ Me 2-cPr, 4,6-Me ₂ 0 0
2019 Cl H SO ₂ Me 2-Br, 5,6-Me ₂ 0 0
2020 Cl H SO ₂ Me 2-cPr, 5,6-Me ₂ 0 0
2021 Cl H SO ₂ Me 2-Br, 5-CH = CH-O-6 0 0
2022 Cl H SO ₂ Me 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
2023 Cl H SO ₂ Me 2-Me, 5-CH ₂ CH ₂ O-6 0 0
2024 Cl H SO ₂ Me 2-Me, 5-CH = CH-O-6 0 0
2025 Cl H SO ₂ Me 2-Et, 5-CH ₂ CH ₂ CH ₂ -6 0 0
2026 Cl H SO ₂ Me 2-cPr, 5-CH ₂ CH ₂ CH ₂ -6 0 0
2027 Cl H SO ₂ Me 2-cPr, 5-CH = CH-O-6 0 0
2028 Cl H SO ₂ Me 2-Br, 3,5,6-Me _Three 0 0
2029 Cl H SO ₂ Et 2-Me 0 0
2030 Cl H SO ₂ Et 2-iPr 0 0
2031 Cl H SO ₂ Et 2-cPr 0 0
2032 Cl H SO ₂ Et 2-CH ₂ CH ₂ CH ₂ -3 0 0
2033 Cl H SO ₂ Et 2,6-Me ₂ 0 0
2034 Cl H SO ₂ Et 2-Me, 6-cPr 0 0
2035 Cl H SO ₂ Pr 2-Cl 0 0
2036 Cl H SO ₂ Pr 2-Br 0 0
2037 Cl H SO ₂ Pr 2-I 0 0
2038 Cl H SO ₂ Pr 2-Me 0 0
2039 Cl H SO ₂ Pr 2-iPr 0 0
2040 Cl H SO ₂ Pr 2-cPr 0 0
2041 Cl H SO ₂ Pr 2-cBu 0 0
2042 Cl H SO ₂ Pr 2-CH ₂ CH ₂ CH ₂ -3 0 0
2043 Cl H SO ₂ Pr 2-cPr, 5-Me 0 0
2044 Cl H SO ₂ Pr 2-OMe, 5-Me 0 0
2045 Cl H SO ₂ Pr 2-F, 6-iPr 0 0
2046 Cl H SO ₂ Pr 2-Cl, 6-cPr 0 0
2047 Cl H SO ₂ Pr 2-Br, 6-Me 0 0
2048 Cl H SO ₂ Pr 2-I, 6-Me 0 0
2049 Cl H SO ₂ Pr 2,6-Me ₂ 0 0
2050 Cl H SO ₂ Pr 2-Me, 6-Et 0 0
2051 Cl H SO ₂ Pr 2-Me, 6-cPr 0 0
2052 Cl H SO ₂ Pr 2,6-cPr ₂ 0 0
2053 Cl H SO ₂ Pr 2-cPr, 3,5-Me ₂ 0 0
2054 Cl H SO ₂ Pr 2-cPr, 5,6-Me ₂ 0 0
2055 Cl H SO ₂ iPr 2-Me 0 0
2056 Cl H SO ₂ iPr 2-iPr 0 0
2057 Cl H SO ₂ iPr 2-cPr 0 0
2058 Cl H SO ₂ iPr 2-CH ₂ CH ₂ CH ₂ -3 0 0
2059 Cl H SO ₂ iPr 2,6-Me ₂ 0 0
2060 Cl H SO ₂ iPr 2-Me, 6-cPr 0 0
2061 Cl H SO ₂ C ₈ H ₁₇ 2-Me 0 0
2062 Cl H SO ₂ C ₈ H ₁₇ 2-iPr 0 0
2063 Cl H SO ₂ C ₈ H ₁₇ 2-cPr 0 0
2064 Cl H SO ₂ C ₈ H ₁₇ 2-CH ₂ CH ₂ CH ₂ -3 0 0
2065 Cl H SO ₂ C ₈ H ₁₇ 2,6-Me ₂ 0 0
2066 Cl H SO ₂ C ₈ H ₁₇ 2-Me, 6-cPr 0 0
2067 Cl H SO ₂ CH ₂ Cl 2-Me 0 0
2068 Cl H SO ₂ CH ₂ Cl 2-iPr 0 0
2069 Cl H SO ₂ CH ₂ Cl 2-cPr 0 0
2070 Cl H SO ₂ CH ₂ Cl 2-CH ₂ CH ₂ CH ₂ -3 0 0
2071 Cl H SO ₂ CH ₂ Cl 2,6-Me ₂ 0 0
2072 Cl H SO ₂ CH ₂ Cl 2-Me, 6-cPr 0 0
2073 Cl H SO ₂ CF _Three 2-F 0 0
2074 Cl H SO ₂ CF _Three 2-Cl 0 0
2075 Cl H SO ₂ CF _Three 2-Br 0 0
2076 Cl H SO ₂ CF _Three 2-I 0 0
2077 Cl H SO ₂ CF _Three 2-Me 0 0
2078 Cl H SO ₂ CF _Three 2-Et 0 0
2079 Cl H SO ₂ CF _Three 2-iPr 0 0
2080 Cl H SO ₂ CF _Three 2-tBu 0 0
2081 Cl H SO ₂ CF _Three 2-cPr 0 0
2082 Cl H SO ₂ CF _Three 2- (cPr-1-Me) 0 0
2083 Cl H SO ₂ CF _Three 2- (cPr-2-Me) 0 0
2084 Cl H SO ₂ CF _Three 2- (cPr-2,2-Cl ₂ ) 0 0
2085 Cl H SO ₂ CF _Three 2-cBu 0 0
2086 Cl H SO ₂ CF _Three 2-CH ₂ CH ₂ CH ₂ -3 0 0
2087 Cl H SO ₂ CF _Three 2-CH = CH-O-3 0 0
2088 Cl H SO ₂ CF _Three 2-CH ₂ CH ₂ O-3 0 0
2089 Cl H SO ₂ CF _Three 2-OCH = CH-3 0 0
2090 Cl H SO ₂ CF _Three 2-OCH ₂ CH ₂ -3 0 0
2091 Cl H SO ₂ CF _Three 2-cPr, 5-F 0 0
2092 Cl H SO ₂ CF _Three 2-cPr, 5-Cl 0 0
2093 Cl H SO ₂ CF _Three 2-cPr, 5-Me 0 0
2094 Cl H SO ₂ CF _Three 2-OMe, 5-Me 0 0
2095 Cl H SO ₂ CF _Three 2-F, 6-iPr 0 0
2096 Cl H SO ₂ CF _Three 2-F, 6-cPr 0 0
2097 Cl H SO ₂ CF _Three 2-Cl, 6-Me 0 0
2098 Cl H SO ₂ CF _Three 2-Cl, 6-cPr 0 0
2099 Cl H SO ₂ CF _Three 2-Br, 6-Me 0 0
2100 Cl H SO ₂ CF _Three 2-Br, 6-Et 0 0
2101 Cl H SO ₂ CF _Three 2-Br, 6-cPr 0 0
2102 Cl H SO ₂ CF _Three 2-I, 6-Me 0 0
2103 Cl H SO ₂ CF _Three 2-I, 6-Et 0 0
2104 Cl H SO ₂ CF _Three 2,6-Me ₂ 0 0
2105 Cl H SO ₂ CF _Three 2-Me, 6-Et 0 0
2106 Cl H SO ₂ CF _Three 2-Me, 6-cPr 0 0
2107 Cl H SO ₂ CF _Three 2-Et, 6-cPr 0 0
2108 Cl H SO ₂ CF _Three 2-iPr, 6-cPr 0 0
2109 Cl H SO ₂ CF _Three 2-tBu, 6-cPr 0 0
2110 Cl H SO ₂ CF _Three 2,6-cPr ₂ 0 0
2111 Cl H SO ₂ CF _Three 2-cPr, 6-OMe 0 0
2112 Cl H SO ₂ CF _Three 2-Br, 3,6-Me ₂ 0 0
2113 Cl H SO ₂ CF _Three 2-cPr, 3,5-Me ₂ 0 0
2114 Cl H SO ₂ CF _Three 2-cPr, 4,6-Me ₂ 0 0
2115 Cl H SO ₂ CF _Three 2-Br, 5,6-Me ₂ 0 0
2116 Cl H SO ₂ CF _Three 2-cPr, 5,6-Me ₂ 0 0
2117 Cl H SO ₂ CF _Three 2-Br, 5-CH = CH-O-6 0 0
2118 Cl H SO ₂ CF _Three 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
2119 Cl H SO ₂ CF _Three 2-Me, 5-CH ₂ CH ₂ O-6 0 0
2120 Cl H SO ₂ CF _Three 2-Me, 5-CH = CH-O-6 0 0
2121 Cl H SO ₂ CF _Three 2-Et, 5-CH ₂ CH ₂ CH ₂ -6 0 0
2122 Cl H SO ₂ CF _Three 2-cPr, 5-CH ₂ CH ₂ CH ₂ -6 0 0
2123 Cl H SO ₂ CF _Three 2-cPr, 5-CH = CH-O-6 0 0
2124 Cl H SO ₂ CF _Three 2-Br, 3,5,6-Me _Three 0 0
2125 Cl H SO ₂ CCl _Three 2-Me 0 0
2126 Cl H SO ₂ CCl _Three 2-iPr 0 0
2127 Cl H SO ₂ CCl _Three 2-cPr 0 0
2128 Cl H SO ₂ CCl _Three 2-CH ₂ CH ₂ CH ₂ -3 0 0
2129 Cl H SO ₂ CCl _Three 2,6-Me ₂ 0 0
2130 Cl H SO ₂ CCl _Three 2-Me, 6-cPr 0 0
2131 Cl H SO ₂ CH ₂ CF _Three 2-Me 0 0
2132 Cl H SO ₂ CH ₂ CF _Three 2-iPr 0 0
2133 Cl H SO ₂ CH ₂ CF _Three 2-cPr 0 0
2134 Cl H SO ₂ CH ₂ CF _Three 2-CH ₂ CH ₂ CH ₂ -3 0 0
2135 Cl H SO ₂ CH ₂ CF _Three 2,6-Me ₂ 0 0
2136 Cl H SO ₂ CH ₂ CF _Three 2-Me, 6-cPr 0 0
2137 Cl H SO ₂ CH ₂ CH ₂ CH ₂ Cl 2-Me 0 0
2138 Cl H SO ₂ CH ₂ CH ₂ CH ₂ Cl 2-iPr 0 0
2139 Cl H SO ₂ CH ₂ CH ₂ CH ₂ Cl 2-cPr 0 0
2140 Cl H SO ₂ CH ₂ CH ₂ CH ₂ Cl 2-CH ₂ CH ₂ CH ₂ -3 0 0
2141 Cl H SO ₂ CH ₂ CH ₂ CH ₂ Cl 2,6-Me ₂ 0 0
2142 Cl H SO ₂ CH ₂ CH ₂ CH ₂ Cl 2-Me, 6-cPr 0 0
2143 Cl H SO ₂ Ph 2-F 0 0
2144 Cl H SO ₂ Ph 2-Cl 0 0
2145 Cl H SO ₂ Ph 2-Br 0 0
2146 Cl H SO ₂ Ph 2-I 0 0
2147 Cl H SO ₂ Ph 2-Me 0 0
2148 Cl H SO ₂ Ph 2-Et 0 0
2149 Cl H SO ₂ Ph 2-iPr 0 0
2150 Cl H SO ₂ Ph 2-tBu 0 0
2151 Cl H SO ₂ Ph 2-cPr 0 0
2152 Cl H SO ₂ Ph 2- (cPr-1-Me) 0 0
2153 Cl H SO ₂ Ph 2- (cPr-2-Me) 0 0
2154 Cl H SO ₂ Ph 2- (cPr-2,2-Cl ₂ ) 0 0
2155 Cl H SO ₂ Ph 2-cBu 0 0
2156 Cl H SO ₂ Ph 2-CH ₂ CH ₂ CH ₂ -3 0 0
2157 Cl H SO ₂ Ph 2-CH = CHO-3 0 0
2158 Cl H SO ₂ Ph 2-CH ₂ CH ₂ O-3 0 0
2159 Cl H SO ₂ Ph 2-OCH = CH-3 0 0
2160 Cl H SO ₂ Ph 2-OCH ₂ CH ₂ -3 0 0
2161 Cl H SO ₂ Ph 2-cPr, 5-F 0 0
2162 Cl H SO ₂ Ph 2-cPr, 5-Cl 0 0
2163 Cl H SO ₂ Ph 2-cPr, 5-Me 0 0
2164 Cl H SO ₂ Ph 2-OMe, 5-Me 0 0
2165 Cl H SO ₂ Ph 2-F, 6-iPr 0 0
2166 Cl H SO ₂ Ph 2-F, 6-cPr 0 0
2167 Cl H SO ₂ Ph 2-Cl, 6-Me 0 0
2168 Cl H SO ₂ Ph 2-Cl, 6-cPr 0 0
2169 Cl H SO ₂ Ph 2-Br, 6-Me 0 0
2170 Cl H SO ₂ Ph 2-Br, 6-Et 0 0
2171 Cl H SO ₂ Ph 2-Br, 6-cPr 0 0
2172 Cl H SO ₂ Ph 2-I, 6-Me 0 0
2173 Cl H SO ₂ Ph 2-I, 6-Et 0 0
2174 Cl H SO ₂ Ph 2,6-Me ₂ 0 0
2175 Cl H SO ₂ Ph 2-Me, 6-Et 0 0
2176 Cl H SO ₂ Ph 2-Me, 6-cPr 0 0
2177 Cl H SO ₂ Ph 2-Et, 6-cPr 0 0
2178 Cl H SO ₂ Ph 2-iPr, 6-cPr 0 0
2179 Cl H SO ₂ Ph 2-tBu, 6-cPr 0 0
2180 Cl H SO ₂ Ph 2,6-cPr ₂ 0 0
2181 Cl H SO ₂ Ph 2-cPr, 6-OMe 0 0
2182 Cl H SO ₂ Ph 2-Br, 3,6-Me ₂ 0 0
2183 Cl H SO ₂ Ph 2-cPr, 3,5-Me ₂ 0 0
2184 Cl H SO ₂ Ph 2-cPr, 4,6-Me ₂ 0 0
2185 Cl H SO ₂ Ph 2-Br, 5,6-Me ₂ 0 0
2186 Cl H SO ₂ Ph 2-cPr, 5,6-Me ₂ 0 0
2187 Cl H SO ₂ Ph 2-Br, 5-CH = CH-O-6 0 0
2188 Cl H SO ₂ Ph 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
2189 Cl H SO ₂ Ph 2-Me, 5-CH ₂ CH ₂ O-6 0 0
2190 Cl H SO ₂ Ph 2-Me, 5-CH = CH-O-6 0 0
2191 Cl H SO ₂ Ph 2-Et, 5-CH ₂ CH ₂ CH ₂ -6 0 0
2192 Cl H SO ₂ Ph 2-cPr, 5-CH ₂ CH ₂ CH ₂ -6 0 0
2193 Cl H SO ₂ Ph 2-cPr, 5-CH = CH-O-6 0 0
2194 Cl H SO ₂ Ph 2-Br, 3,5,6-Me _Three 0 0
2195 Cl H SO ₂ (Ph-4-Cl) 2-Cl 0 0
2196 Cl H SO ₂ (Ph-4-Cl) 2-Br 0 0
2197 Cl H SO ₂ (Ph-4-Cl) 2-I 0 0
2198 Cl H SO ₂ (Ph-4-Cl) 2-Me 0 0
2199 Cl H SO ₂ (Ph-4-Cl) 2-iPr 0 0
2200 Cl H SO ₂ (Ph-4-Cl) 2-tBu 0 0
2201 Cl H SO ₂ (Ph-4-Cl) 2-cPr 0 0
2202 Cl H SO ₂ (Ph-4-Cl) 2-cBu 0 0
2203 Cl H SO ₂ (Ph-4-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2204 Cl H SO ₂ (Ph-4-Cl) 2-cPr, 5-Me 0 0
2205 Cl H SO ₂ (Ph-4-Cl) 2-OMe, 5-Me 0 0
2206 Cl H SO ₂ (Ph-4-Cl) 2-F, 6-iPr 0 0
2207 Cl H SO ₂ (Ph-4-Cl) 2-Cl, 6-cPr 0 0
2208 Cl H SO ₂ (Ph-4-Cl) 2-Br, 6-Me 0 0
2209 Cl H SO ₂ (Ph-4-Cl) 2-I, 6-Me 0 0
2210 Cl H SO ₂ (Ph-4-Cl) 2,6-Me ₂ 0 0
2211 Cl H SO ₂ (Ph-4-Cl) 2-Me, 6-Et 0 0
2212 Cl H SO ₂ (Ph-4-Cl) 2-Me, 6-cPr 0 0
2213 Cl H SO ₂ (Ph-4-Cl) 2,6-cPr ₂ 0 0
2214 Cl H SO ₂ (Ph-4-Cl) 2-cPr, 3,5-Me ₂ 0 0
2215 Cl H SO ₂ (Ph-4-Cl) 2-cPr, 5,6-Me ₂ 0 0
2216 Cl H SO ₂ (Ph-4-Me) 2-F 0 0
2217 Cl H SO ₂ (Ph-4-Me) 2-Cl 0 0
2218 Cl H SO ₂ (Ph-4-Me) 2-Br 0 0
2219 Cl H SO ₂ (Ph-4-Me) 2-I 0 0
2220 Cl H SO ₂ (Ph-4-Me) 2-Me 0 0
2221 Cl H SO ₂ (Ph-4-Me) 2-Et 0 0
2222 Cl H SO ₂ (Ph-4-Me) 2-iPr 0 0
2223 Cl H SO ₂ (Ph-4-Me) 2-sBu 0 0
2224 Cl H SO ₂ (Ph-4-Me) 2-tBu 0 0
2225 Cl H SO ₂ (Ph-4-Me) 2-cPr 0 0
2226 Cl H SO ₂ (Ph-4-Me) 2- (cPr-1-Me) 0 0
2227 Cl H SO ₂ (Ph-4-Me) 2- (cPr-2-Me) 0 0
2228 Cl H SO ₂ (Ph-4-Me) 2- (cPr-2,2-Cl ₂ ) 0 0
2229 Cl H SO ₂ (Ph-4-Me) 2-cBu 0 0
2230 Cl H SO ₂ (Ph-4-Me) 2-cHx 0 0
2231 Cl H SO ₂ (Ph-4-Me) 2-Ph 0 0
2232 Cl H SO ₂ (Ph-4-Me) 2-OMe 0 0
2233 Cl H SO ₂ (Ph-4-Me) 2-OSO ₂ (Ph-4-Me) 0 0
2234 Cl H SO ₂ (Ph-4-Me) 3-Cl 0 0
2235 Cl H SO ₂ (Ph-4-Me) 3-tBu 0 0
2236 Cl H SO ₂ (Ph-4-Me) 3-CF _Three 0 0
2237 Cl H SO ₂ (Ph-4-Me) 3-CN 0 0
2238 Cl H SO ₂ (Ph-4-Me) 3-OMe 0 0
2239 Cl H SO ₂ (Ph-4-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2240 Cl H SO ₂ (Ph-4-Me) 2-CH = CHCH = CH-3 0 0
2241 Cl H SO ₂ (Ph-4-Me) 2-CH = CH-O-3 0 0
2242 Cl H SO ₂ (Ph-4-Me) 2-CH ₂ CH ₂ O-3 0 0
2243 Cl H SO ₂ (Ph-4-Me) 2-OCH = CH-3 0 0
2244 Cl H SO ₂ (Ph-4-Me) 2-OCH ₂ CH ₂ -3 0 0
2245 Cl H SO ₂ (Ph-4-Me) 2-Br, 4-tBu 0 0
2246 Cl H SO ₂ (Ph-4-Me) 2-Me, 4-Cl 0 0
2247 Cl H SO ₂ (Ph-4-Me) 2,4-Me ₂ 0 0
2248 Cl H SO ₂ (Ph-4-Me) 2-iPr, 4-Br 0 0
2249 Cl H SO ₂ (Ph-4-Me) 2-iPr, 5-Me 0 0
2250 Cl H SO ₂ (Ph-4-Me) 2-cPr, 5-F 0 0
2251 Cl H SO ₂ (Ph-4-Me) 2-cPr, 5-Cl 0 0
2252 Cl H SO ₂ (Ph-4-Me) 2-cPr, 5-Me 0 0
2253 Cl H SO ₂ (Ph-4-Me) 2-OMe, 5-Me 0 0
2254 Cl H SO ₂ (Ph-4-Me) 2-F, 6-iPr 0 0
2255 Cl H SO ₂ (Ph-4-Me) 2-F, 6-cPr 0 0
2256 Cl H SO ₂ (Ph-4-Me) 2-Cl, 6-Me 0 0
2257 Cl H SO ₂ (Ph-4-Me) 2-Cl, 6-cPr 0 0
2258 Cl H SO ₂ (Ph-4-Me) 2-Br, 6-Me 0 0
2259 Cl H SO ₂ (Ph-4-Me) 2-Br, 6-Et 0 0
2260 Cl H SO ₂ (Ph-4-Me) 2-Br, 6-cPr 0 0
2261 Cl H SO ₂ (Ph-4-Me) 2-I, 6-Me 0 0
2262 Cl H SO ₂ (Ph-4-Me) 2-I, 6-Et 0 0
2263 Cl H SO ₂ (Ph-4-Me) 2,6-Me ₂ 0 0
2264 Cl H SO ₂ (Ph-4-Me) 2-Me, 6-Et 0 0
2265 Cl H SO ₂ (Ph-4-Me) 2-Me, 6-cPr 0 0
2266 Cl H SO ₂ (Ph-4-Me) 2-Et, 6-cPr 0 0
2267 Cl H SO ₂ (Ph-4-Me) 2-iPr, 6-cPr 0 0
2268 Cl H SO ₂ (Ph-4-Me) 2-tBu, 6-cPr 0 0
2269 Cl H SO ₂ (Ph-4-Me) 2,6-cPr ₂ 0 0
2270 Cl H SO ₂ (Ph-4-Me) 2-cPr, 6-OMe 0 0
2271 Cl H SO ₂ (Ph-4-Me) 2-Br, 3,6-Me ₂ 0 0
2272 Cl H SO ₂ (Ph-4-Me) 2-cPr, 3,5-Me ₂ 0 0
2273 Cl H SO ₂ (Ph-4-Me) 2-cPr, 4,6-Me ₂ 0 0
2274 Cl H SO ₂ (Ph-4-Me) 2-Br, 5,6-Me ₂ 0 0
2275 Cl H SO ₂ (Ph-4-Me) 2-cPr, 5,6-Me ₂ 0 0
2276 Cl H SO ₂ (Ph-4-Me) 2-Br, 5-CH = CH-O-6 0 0
2277 Cl H SO ₂ (Ph-4-Me) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
2278 Cl H SO ₂ (Ph-4-Me) 2-Me, 5-CH ₂ CH ₂ O-6 0 0
2279 Cl H SO ₂ (Ph-4-Me) 2-Me, 5-CH = CH-O-6 0 0
2280 Cl H SO ₂ (Ph-4-Me) 2-Et, 5-CH ₂ CH ₂ CH ₂ -6 0 0
2281 Cl H SO ₂ (Ph-4-Me) 2-cPr, 5-CH ₂ CH ₂ CH ₂ -6 0 0
2282 Cl H SO ₂ (Ph-4-Me) 2-cPr, 5-CH = CH-O-6 0 0
2283 Cl H SO ₂ (Ph-4-Me) 2-Br, 3,5,6-Me _Three 0 0
2284 Cl H SO ₂ (Ph-4-NO ₂ ) 2-Cl 0 0
2285 Cl H SO ₂ (Ph-4-NO ₂ ) 2-Br 0 0
2286 Cl H SO ₂ (Ph-4-NO ₂ ) 2-I 0 0
2287 Cl H SO ₂ (Ph-4-NO ₂ ) 2-Me 0 0
2288 Cl H SO ₂ (Ph-4-NO ₂ ) 2-iPr 0 0
2289 Cl H SO ₂ (Ph-4-NO ₂ ) 2-cPr 0 0
2290 Cl H SO ₂ (Ph-4-NO ₂ ) 2-cBu 0 0
2291 Cl H SO ₂ (Ph-4-NO ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2292 Cl H SO ₂ (Ph-4-NO ₂ ) 2-cPr, 5-Me 0 0
2293 Cl H SO ₂ (Ph-4-NO ₂ ) 2-OMe, 5-Me 0 0
2294 Cl H SO ₂ (Ph-4-NO ₂ ) 2-F, 6-iPr 0 0
2295 Cl H SO ₂ (Ph-4-NO ₂ ) 2-Cl, 6-cPr 0 0
2296 Cl H SO ₂ (Ph-4-NO ₂ ) 2-Br, 6-Me 0 0
2297 Cl H SO ₂ (Ph-4-NO ₂ ) 2-I, 6-Me 0 0
2298 Cl H SO ₂ (Ph-4-NO ₂ ) 2,6-Me ₂ 0 0
2299 Cl H SO ₂ (Ph-4-NO ₂ ) 2-Me, 6-Et 0 0
2300 Cl H SO ₂ (Ph-4-NO ₂ ) 2-Me, 6-cPr 0 0
2301 Cl H SO ₂ (Ph-4-NO ₂ ) 2,6-cPr ₂ 0 0
2302 Cl H SO ₂ (Ph-4-NO ₂ ) 2-cPr, 3,5-Me ₂ 0 0
2303 Cl H SO ₂ (Ph-4-NO ₂ ) 2-cPr, 5,6-Me ₂ 0 0
2304 Cl H SO ₂ (Ph-4-OMe) 2-Me 0 0
2305 Cl H SO ₂ (Ph-4-OMe) 2-iPr 0 0
2306 Cl H SO ₂ (Ph-4-OMe) 2-cPr 0 0
2307 Cl H SO ₂ (Ph-4-OMe) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2308 Cl H SO ₂ (Ph-4-OMe) 2,6-Me ₂ 0 0
2309 Cl H SO ₂ (Ph-4-OMe) 2-Me, 6-cPr 0 0
2310 Cl H SO ₂ (Ph-2,4,6-Me _Three ) 2-Me 0 0
2311 Cl H SO ₂ (Ph-2,4,6-Me _Three ) 2-iPr 0 0
2312 Cl H SO ₂ (Ph-2,4,6-Me _Three ) 2-cPr 0 0
2313 Cl H SO ₂ (Ph-2,4,6-Me _Three ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2314 Cl H SO ₂ (Ph-2,4,6-Me _Three ) 2,6-Me ₂ 0 0
2315 Cl H SO ₂ (Ph-2,4,6-Me _Three ) 2-Me, 6-cPr 0 0
2316 Cl H SO ₂ (Ph-2,4,6-iPr _Three ) 2-Me 0 0
2317 Cl H SO ₂ (Ph-2,4,6-iPr _Three ) 2-iPr 0 0
2318 Cl H SO ₂ (Ph-2,4,6-iPr _Three ) 2-cPr 0 0
2319 Cl H SO ₂ (Ph-2,4,6-iPr _Three ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2320 Cl H SO ₂ (Ph-2,4,6-iPr _Three ) 2,6-Me ₂ 0 0
2321 Cl H SO ₂ (Ph-2,4,6-iPr _Three ) 2-Me, 6-cPr 0 0
2322 Cl H SO ₂ (Ph-2-SO ₂ OQ ^Five ) 2-Me 0 0
2323 Cl H SO ₂ (Ph-2-SO ₂ OQ ^Five ) 2-iPr 0 0
2324 Cl H SO ₂ (Ph-2-SO ₂ OQ ^Five ) 2-cPr 0 0
2325 Cl H SO ₂ (Ph-2-SO ₂ OQ ^Five ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2326 Cl H SO ₂ (Ph-2-SO ₂ OQ ^Five ) 2,6-Me ₂ 0 0
2327 Cl H SO ₂ (Ph-2-SO ₂ OQ ^Five ) 2-Me, 6-cPr 0 0
2328 Cl H SO ₂ (Ph-3-SO ₂ OQ ^Five ) 2-Me 0 0
2329 Cl H SO ₂ (Ph-3-SO ₂ OQ ^Five ) 2-iPr 0 0
2330 Cl H SO ₂ (Ph-3-SO ₂ OQ ^Five ) 2-cPr 0 0
2331 Cl H SO ₂ (Ph-3-SO ₂ OQ ^Five ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2332 Cl H SO ₂ (Ph-3-SO ₂ OQ ^Five ) 2,6-Me ₂ 0 0
2333 Cl H SO ₂ (Ph-3-SO ₂ OQ ^Five ) 2-Me, 6-cPr 0 0
2334 Cl H SO ₂ (Ph-4-SO ₂ OQ ^Five ) 2-Me 0 0
2335 Cl H SO ₂ (Ph-4-SO ₂ OQ ^Five ) 2-iPr 0 0
2336 Cl H SO ₂ (Ph-4-SO ₂ OQ ^Five ) 2-cPr 0 0
2337 Cl H SO ₂ (Ph-4-SO ₂ OQ ^Five ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2338 Cl H SO ₂ (Ph-4-SO ₂ OQ ^Five ) 2,6-Me ₂ 0 0
2339 Cl H SO ₂ (Ph-4-SO ₂ OQ ^Five ) 2-Me, 6-cPr 0 0
2340 Cl H SO ₂ OQ ^Five 2-Me 0 0
2341 Cl H SO ₂ OQ ^Five 2-iPr 0 0
2342 Cl H SO ₂ OQ ^Five 2-cPr 0 0
2343 Cl H SO ₂ OQ ^Five 2-CH ₂ CH ₂ CH ₂ -3 0 0
2344 Cl H SO ₂ OQ ^Five 2,6-Me ₂ 0 0
2345 Cl H SO ₂ OQ ^Five 2-Me, 6-cPr 0 0
2346 Cl H SO ₂ NMe ₂ 2-Cl 0 0
2347 Cl H SO ₂ NMe ₂ 2-Br 0 0
2348 Cl H SO ₂ NMe ₂ 2-I 0 0
2349 Cl H SO ₂ NMe ₂ 2-Me 0 0
2350 Cl H SO ₂ NMe ₂ 2-iPr 0 0
2351 Cl H SO ₂ NMe ₂ 2-cPr 0 0
2352 Cl H SO ₂ NMe ₂ 2-cBu 0 0
2353 Cl H SO ₂ NMe ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
2354 Cl H SO ₂ NMe ₂ 2-cPr, 5-Me 0 0
2355 Cl H SO ₂ NMe ₂ 2-OMe, 5-Me 0 0
2356 Cl H SO ₂ NMe ₂ 2-F, 6-iPr 0 0
2357 Cl H SO ₂ NMe ₂ 2-Cl, 6-cPr 0 0
2358 Cl H SO ₂ NMe ₂ 2-Br, 6-Me 0 0
2359 Cl H SO ₂ NMe ₂ 2-I, 6-Me 0 0
2360 Cl H SO ₂ NMe ₂ 2,6-Me ₂ 0 0
2361 Cl H SO ₂ NMe ₂ 2-Me, 6-Et 0 0
2362 Cl H SO ₂ NMe ₂ 2-Me, 6-cPr 0 0
2363 Cl H SO ₂ NMe ₂ 2,6-cPr ₂ 0 0
2364 Cl H SO ₂ NMe ₂ 2-cPr, 3,5-Me ₂ 0 0
2365 Cl H SO ₂ NMe ₂ 2-cPr, 5,6-Me ₂ 0 0
2366 Cl H SO ₂ OEt 2-Me 0 0
2367 Cl H SO ₂ OEt 2-iPr 0 0
2368 Cl H SO ₂ OEt 2-cPr 0 0
2369 Cl H SO ₂ OEt 2-CH ₂ CH ₂ CH ₂ -3 0 0
2370 Cl H SO ₂ OEt 2,6-Me ₂ 0 0
2371 Cl H SO ₂ OEt 2-Me, 6-cPr 0 0
2372 Cl Me H 2-Me 0 0
2373 Cl Me H 2-iPr 0 0
2374 Cl Me H 2-cPr 0 0
2375 Cl Me H 2-CH ₂ CH ₂ CH ₂ -3 0 0
2376 Cl Me H 2,6-Me ₂ 0 0
2377 Cl Me H 2-Me, 6-cPr 0 0
2378 Cl CH ₂ OMe H 2-Me 0 0
2379 Cl CH ₂ OMe H 2-iPr 0 0
2380 Cl CH ₂ OMe H 2-cPr 0 0
2381 Cl CH ₂ OMe H 2-CH ₂ CH ₂ CH ₂ -3 0 0
2382 Cl CH ₂ OMe H 2,6-Me ₂ 0 0
2383 Cl CH ₂ OMe H 2-Me, 6-cPr 0 0
2384 Cl CO ₂ Et H 2-Me 0 0
2385 Cl CO ₂ Et H 2-iPr 0 0
2386 Cl CO ₂ Et H 2-tBu 0 0
2387 Cl CO ₂ Et H 2-cPr 0 0
2388 Cl CO ₂ Et H 2-CH ₂ CH ₂ CH ₂ -3 0 0
2389 Cl CO ₂ Et H 2,6-Me ₂ 0 0
2390 Cl CO ₂ Et H 2-Me, 6-cPr 0 0
2391 Cl CO (Ph-2-F) H 2-tBu 0 0
2392 Cl OMe H 2-Me 0 0
2393 Cl O (Ph-2,4-F ₂ ) H 2,4-F ₂ 0 0
2394 Cl O (Ph-2,6-F ₂ ) H 2,6-F ₂ 0 0
2395 Cl O (Ph-2-Me) H 2-Me 0 0
2396 Cl O (Ph-2-Me) H 2-iPr 0 0
2397 Cl O (Ph-2-Me) H 2-cPr 0 0
2398 Cl O (Ph-2-Me) H 2-CH ₂ CH ₂ CH ₂ -3 0 0
2399 Cl O (Ph-2-Me) H 2,6-Me ₂ 0 0
2400 Cl O (Ph-2-Me) H 2-Me, 6-cPr 0 0
2401 Cl SPh H 2-Me 0 0
2402 Cl SiMe _Three HH 0 0
2403 Cl SiMe _Three H 2-Me 0 0
2404 Cl SiMe _Three H 2-iPr 0 0
2405 Cl SiMe _Three H 2-tBu 0 0
2406 Cl SiMe _Three H 2-cPr 0 0
2407 Cl SiMe _Three H 2-CH ₂ CH ₂ CH ₂ -3 0 0
2408 Cl SiMe _Three H 2,6-Me ₂ 0 0
2409 Cl SiMe _Three H 2-Me, 6-cPr 0 0
2410 Br HH 2-Cl 0 0
2411 Br HH 2-Me 0 0
2412 Br HH 2-iPr 0 0
2413 Br HH 2-cPr 0 0
2414 Br HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2415 Br HH 2,6-Me ₂ 0 0
2416 Br HH 2-Me, 6-cPr 0 0
2417 Me HH 2-Me 0 0
2418 Me HH 2-iPr 0 0
2419 Me HH 2-cPr 0 0
2420 Me HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2421 Me HH 2,6-Me ₂ 0 0
2422 Me HH 2-Me, 6-cPr 0 0
2423 cPr HH 2-Me 0 0
2424 cPr HH 2-iPr 0 0
2425 cPr HH 2-cPr 0 0
2426 cPr HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2427 cPr HH 2,6-Me ₂ 0 0
2428 cPr HH 2-Me, 6-cPr 0 0
2429 CF _Three HH 2-Cl 0 0
2430 CF _Three HH 2-Me 0 0
2431 CF _Three HH 2-iPr 0 0
2432 CF _Three HH 2-cPr 0 0
2433 CF _Three HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2434 CF _Three HH 2,6-Me ₂ 0 0
2435 CF _Three HH 2-Me, 6-cPr 0 0
2436 CH = CH ₂ HH 2-Me 0 0
2437 CH = CH ₂ HH 2-iPr 0 0
2438 CH = CH ₂ HH 2-cPr 0 0
2439 CH = CH ₂ HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2440 CH = CH ₂ HH 2,6-Me ₂ 0 0
2441 CH = CH ₂ HH 2-Me, 6-cPr 0 0
2442 CH = CHMe HH 2-Me 0 0
2443 CH = CHMe HH 2-iPr 0 0
2444 CH = CHMe HH 2-cPr 0 0
2445 CH = CHMe HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2446 CH = CHMe HH 2,6-Me ₂ 0 0
2447 CH = CHMe HH 2-Me, 6-cPr 0 0
2448 CH ₂ CH = CH ₂ HH 2-Me 0 0
2449 CN HH 2-Me 0 0
2450 CN HH 2-iPr 0 0
2451 CN HH 2-cPr 0 0
2452 CN HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2453 CN HH 2,6-Me ₂ 0 0
2454 CN HH 2-Me, 6-cPr 0 0
2455 COMe HH 2-Me 0 0
2456 COMe HH 2-iPr 0 0
2457 COMe HH 2-cPr 0 0
2458 COMe HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2459 COMe HH 2,6-Me ₂ 0 0
2460 COMe HH 2-Me, 6-cPr 0 0
2461 COBu HH 2,6-Me ₂ 0 0
2462 CONMe ₂ HH 2,6-Me ₂ 0 0
2463 CONMe ₂ SiMe _Three H 2,6-Me ₂ 0 0
2464 Ph HH 2-Me 0 0
2465 Ph HH 2-iPr 0 0
2466 Ph HH 2-cPr 0 0
2467 Ph HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2468 Ph HH 2,6-Me ₂ 0 0
2469 Ph HH 2-Me, 6-cPr 0 0
2470 Ph HH 3-CN 0 0
2471 Ph-3-CF _Three HH 2-Me 0 0
2472 Ph-3-CN HH 2-iPr 0 0
2473 Ph-3-CN HH 2-cPr 0 0
2474 Ph-3-CN HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2475 Ph-3-CN HH 2,6-Me ₂ 0 0
2476 Ph-3-CN HH 2-Me, 6-cPr 0 0
2477 2-Fur HH 2-Me 0 0
2478 2-Thi HH 2-Me 0 0
2479 2-Thi HH 2-iPr 0 0
2480 2-Thi HH 2-cPr 0 0
2481 2-Thi HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2482 2-Thi HH 2,6-Me ₂ 0 0
2483 2-Thi HH 2-Me, 6-cPr 0 0
2484 OMe HH 2-Me 0 0
2485 O (Ph-2-F) HH 2-F 0 0
2486 O (Ph-2-F) HH 2-Me 0 0
2487 O (Ph-2-F) HH 2-iPr 0 0
2488 O (Ph-2-F) HH 2-cPr 0 0
2489 O (Ph-2-F) HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2490 O (Ph-2-F) HH 2,6-Me ₂ 0 0
2491 O (Ph-2-F) HH 2-Me, 6-cPr 0 0
2492 O (Ph-2-Me) HH 2-Me 0 0
2493 O (Ph-2-Me) HH 2-iPr 0 0
2494 O (Ph-2-Me) HH 2-cPr 0 0
2495 O (Ph-2-Me) HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2496 O (Ph-2-Me) HH 2,6-Me ₂ 0 0
2497 O (Ph-2-Me) HH 2-Me, 6-cPr 0 0
2498 O (Ph-2-Me) CO ₂ Et H 2-Me 0 0
2499 O (Ph-4-tBu) HH 4-tBu 0 0
2500 O (Ph-2-iPr-5-Me) HH 2-iPr, 5-Me 0 0
2501 O (Ph-2,3,5-Me _Three ) HH 2,3,5-Me _Three 0 0
2502 O (Ph-2,4,6-Me _Three ) HH 2,4,6-Me _Three 0 0
2503 O (Ph-2-cHx) HH 2-cHx 0 0
2504 O (Ph-3-CN) HH 3-CN 0 0
2505 O (Ph-4-SiMe _Three ) HH 4-SiMe _Three 0 0
2506 OQ ^Five HH 2-Me 0 0
2507 OQ ^Five HH 2-iPr 0 0
2508 OQ ^Five HH 2-cPr 0 0
2509 OQ ^Five HH 2-CH ₂ CH ₂ CH ₂ -3 0 0
2510 OQ ^Five HH 2,6-Me ₂ 0 0
2511 OQ ^Five HH 2-Me, 6-cPr 0 0
2512 Cl HH 2- (cPr-1-F-2-F) 0 0
2513 Cl HH 2- (cPr-1-F-2-Cl) 0 0
2514 Cl HH 2- (cPr-1,2-Cl ₂ ) 0 0
2515 Cl HH 2- (cPr-1-Cl-2-Br) 0 0
2516 Cl HH 2- (cPr-1,2-Br ₂ ) 0 0
2517 Cl HH 2- (cPr-1-Me-2-Cl) 0 0
2518 Cl HH 2- (cPr-1-Me-2-Br) 0 0
2519 Cl HH 2- (cPr-2-F-2-Cl) 0 0
2520 Cl HH 2- (cPr-2-F-2-Br) 0 0
2521 Cl HH 2- (cPr-2-Cl-2-Br) 0 0
2522 Cl HH 2- (cPr-1-Me-2,2-Cl ₂ ) 0 0
2523 Cl HH 2- (cPr-1-Me-2,2-Br ₂ ) 0 0
2524 Cl HH 2- (cPr-1-Me-2-F-2-Cl) 0 0
2525 Cl HH 2-C (F) = CH ₂ 0 0
2526 Cl HH 2-C (Cl) = CH ₂ 0 0
2527 Cl HH 2-C (Br) = CH ₂ 0 0
2528 Cl HH 2-C (Et) = CH ₂ 0 0
2529 Cl HH 2-C (iPr) = CH ₂ 0 0
2530 Cl HH 2-C (tBu) = CH ₂ 0 0
2531 Cl HH 2-C (CN) = CH ₂ 0 0
2532 Cl HH 2-CH = CHF 0 0
2533 Cl HH 2-CH = CHCl 0 0
2534 Cl HH 2-CH = CHBr 0 0
2535 Cl HH 2-CCl = CHCl 0 0
2536 Cl HH 2-CMe = CHCl 0 0
2537 Cl HH 2-CH = CF ₂ 0 0
2538 Cl HH 2-CH = CCl ₂ 0 0
2539 Cl HH 2-CH = CBr ₂ 0 0
2540 Cl HH 2-CH = CMe ₂ 0 0
2541 Cl HH 2-CCl = CCl ₂ 0 0
2542 Cl HH 2-CMe = CMe ₂ 0 0
2543 Cl HH 2-CH = C (CN) ₂ 0 0
2544 Cl HH 3-OH 0 0
2545 Cl HH 4-OH 0 0
2546 Cl HH 2-OCH ₂ Ph 0 0
2547 Cl HH 3-OCH ₂ Ph 0 0
2548 Cl HH 4-OCH ₂ Ph 0 0
2549 Cl HH 2-I, 3-F 0 0
2550 Cl HH 2-I, 3-Me 0 0
2551 Cl HH 2-I, 3-OMe 0 0
2552 Cl HH 2-CHMeCH ₂ -3 0 0
2553 Cl HH 2-CMe ₂ CH ₂ -3 0 0
2554 Cl HH 2-CH ₂ CHMe-3 0 0
2555 Cl HH 2-CH ₂ CH {(CH ₂ ) _Three OH} -3 0 0
2556 Cl HH 2-CH ₂ CMe ₂ -3 0 0
2557 Cl HH 2-CH (CH ₂ ) CH-3 0 0
2558 Cl HH 2-CH (-CH ₂ CH ₂ -) CH ₂ -3 0 0
2559 Cl HH 2-CHOMeCH ₂ -3 0 0
2560 Cl HH 2-C (= O) CH ₂ -3 0 0
2561 Cl HH 2-CH ₂ C (= O) -3 0 0
2562 Cl HH 2-C (= O) C (= O) -3 0 0
2563 Cl HH 2-CH ₂ CH ₂ NMe-3 0 0
2564 Cl HH 2-CH = CHNH-3 0 0
2565 Cl HH 2-CH = CHNMe-3 0 0
2566 Cl HH 2-NMeCH ₂ CH ₂ -3 0 0
2567 Cl HH 2-NHCH = CH-3 0 0
2568 Cl HH 2-NMeCH = CH-3 0 0
2569 Cl HH 2-N (COMe) CH = CH-3 0 0
2570 Cl HH 2-Me, 4-COMe 0 0
2571 Cl HH 2-Me, 4-C (= NOMe) Me 0 0
2572 Cl HH 2-Me, 4-OCOMe 0 0
2573 Cl HH 2-Me, 4-OCOPh 0 0
2574 Cl HH 2-OMe, 5-CO ₂ Me 0 0
2575 Cl HH 2-Me, 6-CH ₂ F 0 0
2576 Cl HH 2-Me, 6-CHF ₂ 0 0
2577 Cl HH 2-Me, 6-CMe = CH ₂ 0 0
2578 Cl HH 2-Me, 6-COMe 0 0
2579 Cl HH 2-Me, 6-C (= NOMe) Me 0 0
2580 Cl HH 2-OMe, 6-CO ₂ Me 0 0
2581 Cl HH 2-Me, 6-OCOMe 0 0
2582 Cl HH 2-Me, 6-OCOPh 0 0
2583 Cl HH 3-Me, 4-F 0 0
2584 Cl HH 3-CH ₂ CH ₂ CH ₂ -4 0 0
2585 Cl HH 3-CH ₂ CH ₂ CMe ₂ -4 0 0
2586 Cl HH 2,6-Me ₂ , 3-Br 0 0
2587 Cl HH 2-Me, 3-Br, 6-cPr 0 0
2588 Cl HH 2,6-Me ₂ , 3-NO ₂ 0 0
2589 Cl HH 2-Me, 3-NO ₂ , 6-cPr 0 0
2590 Cl HH 6-Cl, 2-CH ₂ OCH ₂ -3 0 0
2591 Cl HH 6-Br, 2-CH ₂ OCH ₂ -3 0 0
2592 Cl HH 6-Me, 2-CH ₂ OCH ₂ -3 0 0
2593 Cl HH 6-Et, 2-CH ₂ OCH ₂ -3 0 0
2594 Cl HH 6-iPr, 2-CH ₂ OCH ₂ -3 0 0
2595 Cl HH 6-cPr, 2-CH ₂ OCH ₂ -3 0 0
2596 Cl HH 2,4-Br ₂ , 5-SEt 0 0
2597 Cl HH 2-F, 3,5,6-Me _Three 0 0
2598 Cl HH 2,3,5,6-Cl _Four 0 0
2599 Cl HH 2-Cl, 3,5,6-Me _Three 0 0
2600 Cl HH 2-I, 3,5,6-Me _Three 0 0
2601 Cl HH 2,3,5-Me _Three , 6-Et 0 0
2602 Cl HH 2,3,5-Me _Three , 6-iPr 0 0
2603 Cl HH 2,3,5-Me _Three , 6-CH = CH ₂ 0 0
2604 Cl HH 2,3,5-Me _Three , 6-CCl = CH ₂ 0 0
2605 Cl HH 2,3,5-Me _Three , 6-CMe = CH ₂ 0 0
2606 Cl HH 2,3,5-Me _Three , 6-CH (SEt) Me 0 0
2607 Cl HH 2,3,5-Me _Three , 6-COMe 0 0
2608 Cl HH 2,3,5-Me _Three , 6-NO ₂ 0 0
2609 Cl HH 2,4-Cl ₂ , 3,5,6-Me _Three 0 0
2610 Cl HH 2,3,4,5,6-F _Five 0 0
2611 Cl HH 2,3,4,5,6-Cl _Five 0 0
2612 Cl HH 2-Cl, 3,4,5,6-Me _Four 0 0
2613 Cl HH 2-Br, 3,4,5,6-Me _Four 0 0
2614 Cl HH 2,3,4,5,6-Me _Five 0 0
2615 Cl HH 2,3,4,5-Me _Four , 6-Et 0 0
2616 Cl HH 2,3,4,5-Me _Four , 6-iPr 0 0
2617 Cl HH 2,3,4,5-Me _Four , 6-cPr 0 0
2618 Cl H COEt 2-Cl 0 0
2619 Cl H COEt 2-Br 0 0
2620 Cl H COEt 2-I 0 0
2621 Cl H COEt 2-cBu 0 0
2622 Cl H COEt 2-cPr, 5-Me 0 0
2623 Cl H COEt 2-OMe, 5-Me 0 0
2624 Cl H COEt 2-F, 6-iPr 0 0
2625 Cl H COEt 2-Cl, 6-cPr 0 0
2626 Cl H COEt 2-Br, 6-Me 0 0
2627 Cl H COEt 2-I, 6-Me 0 0
2628 Cl H COEt 2-Me, 6-Et 0 0
2629 Cl H COEt 2,6-cPr ₂ 0 0
2630 Cl H COEt 2-cPr, 3,5-Me ₂ 0 0
2631 Cl H COEt 2-cPr, 3,6-Me ₂ 0 0
2632 Cl H COiPr 2-Cl 0 0
2633 Cl H COiPr 2-Br 0 0
2634 Cl H COiPr 2-I 0 0
2635 Cl H COiPr 2-cBu 0 0
2636 Cl H COiPr 2-cPr, 5-Me 0 0
2637 Cl H COiPr 2-OMe, 5-Me 0 0
2638 Cl H COiPr 2-F, 6-iPr 0 0
2639 Cl H COiPr 2-Cl, 6-cPr 0 0
2640 Cl H COiPr 2-Br, 6-Me 0 0
2641 Cl H COiPr 2-I, 6-Me 0 0
2642 Cl H COiPr 2-Me, 6-Et 0 0
2643 Cl H COiPr 2,6-cPr ₂ 0 0
2644 Cl H COiPr 2-cPr, 3,5-Me ₂ 0 0
2645 Cl H COiPr 2-cPr, 3,6-Me ₂ 0 0
2646 Cl H COneoPen 2-Cl 0 0
2647 Cl H COneoPen 2-Br 0 0
2648 Cl H COneoPen 2-I 0 0
2649 Cl H COneoPen 2-Me 0 0
2650 Cl H COneoPen 2-iPr 0 0
2651 Cl H COneoPen 2-cPr 0 0
2652 Cl H COneoPen 2-cBu 0 0
2653 Cl H COneoPen 2-CH ₂ CH ₂ CH ₂ -3 0 0
2654 Cl H COneoPen 2-cPr, 5-Me 0 0
2655 Cl H COneoPen 2-OMe, 5-Me 0 0
2656 Cl H COneoPen 2-F, 6-iPr 0 0
2657 Cl H COneoPen 2-Cl, 6-cPr 0 0
2658 Cl H COneoPen 2-Br, 6-Me 0 0
2659 Cl H COneoPen 2-I, 6-Me 0 0
2660 Cl H COneoPen 2,6-Me ₂ 0 0
2661 Cl H COneoPen 2-Me, 6-Et 0 0
2662 Cl H COneoPen 2-Me, 6-cPr 0 0
2663 Cl H COneoPen 2,6-cPr ₂ 0 0
2664 Cl H COneoPen 2-cPr, 3,5-Me ₂ 0 0
2665 Cl H COneoPen 2-cPr, 3,6-Me ₂ 0 0
2666 Cl H CO (1-Ad) 2-Me 0 0
2667 Cl H CO (1-Ad) 2-iPr 0 0
2668 Cl H CO (1-Ad) 2-cPr 0 0
2669 Cl H CO (1-Ad) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2670 Cl H CO (1-Ad) 2,6-Me ₂ 0 0
2671 Cl H CO (1-Ad) 2-Me, 6-cPr 0 0
2672 Cl H COCMe = CH ₂ 2-Me 0 0
2673 Cl H COCMe = CH ₂ 2-iPr 0 0
2674 Cl H COCMe = CH ₂ 2-cPr 0 0
2675 Cl H COCMe = CH ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
2676 Cl H COCMe = CH ₂ 2,6-Me ₂ 0 0
2677 Cl H COCMe = CH ₂ 2-Me, 6-cPr 0 0
2678 Cl H COCH = CMe ₂ 2-Cl 0 0
2679 Cl H COCH = CMe ₂ 2-Br 0 0
2680 Cl H COCH = CMe ₂ 2-I 0 0
2681 Cl H COCH = CMe ₂ 2-cBu 0 0
2682 Cl H COCH = CMe ₂ 2-cPr, 5-Me 0 0
2683 Cl H COCH = CMe ₂ 2-OMe, 5-Me 0 0
2684 Cl H COCH = CMe ₂ 2-F, 6-iPr 0 0
2685 Cl H COCH = CMe ₂ 2-Cl, 6-cPr 0 0
2686 Cl H COCH = CMe ₂ 2-Br, 6-Me 0 0
2687 Cl H COCH = CMe ₂ 2-I, 6-Me 0 0
2688 Cl H COCH = CMe ₂ 2-Me, 6-Et 0 0
2689 Cl H COCH = CMe ₂ 2,6-cPr ₂ 0 0
2690 Cl H COCH = CMe ₂ 2-cPr, 3,5-Me ₂ 0 0
2691 Cl H COCH = CMe ₂ 2-cPr, 3,6-Me ₂ 0 0
2692 Cl H COCMe ₂ Br 2-Me 0 0
2693 Cl H COCMe ₂ Br 2-iPr 0 0
2694 Cl H COCMe ₂ Br 2-cPr 0 0
2695 Cl H COCMe ₂ Br 2-CH ₂ CH ₂ CH ₂ -3 0 0
2696 Cl H COCMe ₂ Br 2,6-Me ₂ 0 0
2697 Cl H COCMe ₂ Br 2-Me, 6-cPr 0 0
2698 Cl H COCMe ₂ CH ₂ Cl 2-Me 0 0
2699 Cl H COCMe ₂ CH ₂ Cl 2-iPr 0 0
2700 Cl H COCMe ₂ CH ₂ Cl 2-cPr 0 0
2701 Cl H COCMe ₂ CH ₂ Cl 2-CH ₂ CH ₂ CH ₂ -3 0 0
2702 Cl H COCMe ₂ CH ₂ Cl 2,6-Me ₂ 0 0
2703 Cl H COCMe ₂ CH ₂ Cl 2-Me, 6-cPr 0 0
2704 Cl H COCH ₂ CH ₂ CH ₂ CH ₂ Br 2-Me 0 0
2705 Cl H COCH ₂ CH ₂ CH ₂ CH ₂ Br 2-iPr 0 0
2706 Cl H COCH ₂ CH ₂ CH ₂ CH ₂ Br 2-cPr 0 0
2707 Cl H COCH ₂ CH ₂ CH ₂ CH ₂ Br 2-CH ₂ CH ₂ CH ₂ -3 0 0
2708 Cl H COCH ₂ CH ₂ CH ₂ CH ₂ Br 2,6-Me ₂ 0 0
2709 Cl H COCH ₂ CH ₂ CH ₂ CH ₂ Br 2-Me, 6-cPr 0 0
2710 Cl H COCHMePh 2-Me 0 0
2711 Cl H COCHMePh 2-iPr 0 0
2712 Cl H COCHMePh 2-cPr 0 0
2713 Cl H COCHMePh 2-CH ₂ CH ₂ CH ₂ -3 0 0
2714 Cl H COCHMePh 2,6-Me ₂ 0 0
2715 Cl H COCHMePh 2-Me, 6-cPr 0 0
2716 Cl H COCH ₂ (Ph-4-OMe) 2-Me 0 0
2717 Cl H COCH ₂ (Ph-4-OMe) 2-iPr 0 0
2718 Cl H COCH ₂ (Ph-4-OMe) 2-cPr 0 0
2719 Cl H COCH ₂ (Ph-4-OMe) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2720 Cl H COCH ₂ (Ph-4-OMe) 2,6-Me ₂ 0 0
2721 Cl H COCH ₂ (Ph-4-OMe) 2-Me, 6-cPr 0 0
2722 Cl H COCH ₂ CH ₂ CO ₂ Et 2-Me 0 0
2723 Cl H COCH ₂ CH ₂ CO ₂ Et 2-iPr 0 0
2724 Cl H COCH ₂ CH ₂ CO ₂ Et 2-cPr 0 0
2725 Cl H COCH ₂ CH ₂ CO ₂ Et 2-CH ₂ CH ₂ CH ₂ -3 0 0
2726 Cl H COCH ₂ CH ₂ CO ₂ Et 2,6-Me ₂ 0 0
2727 Cl H COCH ₂ CH ₂ CO ₂ Et 2-Me, 6-cPr 0 0
2728 Cl H CO (CH ₂ ) ₂ CO ₂ Q ⁶ 2-Me 0 0
2729 Cl H CO (CH ₂ ) ₂ CO ₂ Q ⁷ 2-iPr 0 0
2730 Cl H CO (CH ₂ ) ₂ CO ₂ Q ⁸ 2-cPr 0 0
2731 Cl H CO (CH ₂ ) ₂ CO ₂ Q ⁹ 2-CH ₂ CH ₂ CH ₂ -3 0 0
2732 Cl H CO (CH ₂ ) ₂ CO ₂ Q ^Ten 2,6-Me ₂ 0 0
2733 Cl H CO (CH ₂ ) ₂ CO ₂ Q ¹¹ 2-Me, 6-cPr 0 0
2734 Cl H CO (CH ₂ ) _Three CO ₂ Q ^Five 2-Me 0 0
2735 Cl H CO (CH ₂ ) _Three CO ₂ Q ^Five 2-iPr 0 0
2736 Cl H CO (CH ₂ ) _Three CO ₂ Q ^Five 2-cPr 0 0
2737 Cl H CO (CH ₂ ) _Three CO ₂ Q ^Five 2-CH ₂ CH ₂ CH ₂ -3 0 0
2738 Cl H CO (CH ₂ ) _Three CO ₂ Q ^Five 2,6-Me ₂ 0 0
2739 Cl H CO (CH ₂ ) _Three CO ₂ Q ^Five 2-Me, 6-cPr 0 0
2740 Cl H CO (CH ₂ ) _Three CO ₂ Q ¹² 2-Me, 6-cPr 0 0
2741 Cl H CO (CH ₂ ) _Three CO ₂ Q ¹³ 2-Me, 6-cPr 0 0
2742 Cl H CO (CH ₂ ) _Three CO ₂ Q ¹⁴ 2-Me, 6-cPr 0 0
2743 Cl H CO (CH ₂ ) _Three CO ₂ Q ¹⁵ 2-Me, 6-cPr 0 0
2744 Cl H CO (CH ₂ ) _Three CO ₂ Q ¹⁶ 2-Me, 6-cPr 0 0
2745 Cl H CO (CH ₂ ) _Three CO ₂ Q ¹⁷ 2-Me, 6-cPr 0 0
2746 Cl H CO (CH ₂ ) _Three CO ₂ Q ¹¹ 2-Me, 6-cPr 0 0
2747 Cl H COCH ₂ OMe 2-Me 0 0
2748 Cl H COCH ₂ OMe 2-iPr 0 0
2749 Cl H COCH ₂ OMe 2-cPr 0 0
2750 Cl H COCH ₂ OMe 2-CH ₂ CH ₂ CH ₂ -3 0 0
2751 Cl H COCH ₂ OMe 2,6-Me ₂ 0 0
2752 Cl H COCH ₂ OMe 2-Me, 6-cPr 0 0
2753 Cl H COCH ₂ OPh 2-Me 0 0
2754 Cl H COCH ₂ OPh 2-iPr 0 0
2755 Cl H COCH ₂ OPh 2-cPr 0 0
2756 Cl H COCH ₂ OPh 2-CH ₂ CH ₂ CH ₂ -3 0 0
2757 Cl H COCH ₂ OPh 2,6-Me ₂ 0 0
2758 Cl H COCH ₂ OPh 2-Me, 6-cPr 0 0
2759 Cl H COCH (Me) OPh 2-Me 0 0
2760 Cl H COCH (Me) OPh 2-iPr 0 0
2761 Cl H COCH (Me) OPh 2-cPr 0 0
2762 Cl H COCH (Me) OPh 2-CH ₂ CH ₂ CH ₂ -3 0 0
2763 Cl H COCH (Me) OPh 2,6-Me ₂ 0 0
2764 Cl H COCH (Me) OPh 2-Me, 6-cPr 0 0
2765 Cl H COCH (OMe) Ph 2-Me 0 0
2766 Cl H COCH (OMe) Ph 2-iPr 0 0
2767 Cl H COCH (OMe) Ph 2-cPr 0 0
2768 Cl H COCH (OMe) Ph 2-CH ₂ CH ₂ CH ₂ -3 0 0
2769 Cl H COCH (OMe) Ph 2,6-Me ₂ 0 0
2770 Cl H COCH (OMe) Ph 2-Me, 6-cPr 0 0
2771 Cl H COCH ₂ CH ₂ SMe 2-Me 0 0
2772 Cl H COCH ₂ CH ₂ SMe 2-iPr 0 0
2773 Cl H COCH ₂ CH ₂ SMe 2-cPr 0 0
2774 Cl H COCH ₂ CH ₂ SMe 2-CH ₂ CH ₂ CH ₂ -3 0 0
2775 Cl H COCH ₂ CH ₂ SMe 2,6-Me ₂ 0 0
2776 Cl H COCH ₂ CH ₂ SMe 2-Me, 6-cPr 0 0
2777 Cl H COCO (2-Thi) 2-Me 0 0
2778 Cl H COCO (2-Thi) 2-iPr 0 0
2779 Cl H COCO (2-Thi) 2-cPr 0 0
2780 Cl H COCO (2-Thi) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2781 Cl H COCO (2-Thi) 2,6-Me ₂ 0 0
2782 Cl H COCO (2-Thi) 2-Me, 6-cPr 0 0
2783 Cl H CO (Ph-2-F) 2-Me 0 0
2784 Cl H CO (Ph-2-F) 2-iPr 0 0
2785 Cl H CO (Ph-2-F) 2-cPr 0 0
2786 Cl H CO (Ph-2-F) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2787 Cl H CO (Ph-2-F) 2,6-Me ₂ 0 0
2788 Cl H CO (Ph-2-F) 2-Me, 6-cPr 0 0
2789 Cl H CO (Ph-2-Br) 2-Cl 0 0
2790 Cl H CO (Ph-2-Br) 2-Br 0 0
2791 Cl H CO (Ph-2-Br) 2-I 0 0
2792 Cl H CO (Ph-2-Br) 2-Me 0 0
2793 Cl H CO (Ph-2-Br) 2-iPr 0 0
2794 Cl H CO (Ph-2-Br) 2-cPr 0 0
2795 Cl H CO (Ph-2-Br) 2-cBu 0 0
2796 Cl H CO (Ph-2-Br) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2797 Cl H CO (Ph-2-Br) 2-cPr, 5-Me 0 0
2798 Cl H CO (Ph-2-Br) 2-OMe, 5-Me 0 0
2799 Cl H CO (Ph-2-Br) 2-F, 6-iPr 0 0
2800 Cl H CO (Ph-2-Br) 2-Cl, 6-cPr 0 0
2801 Cl H CO (Ph-2-Br) 2-Br, 6-Me 0 0
2802 Cl H CO (Ph-2-Br) 2-I, 6-Me 0 0
2803 Cl H CO (Ph-2-Br) 2,6-Me ₂ 0 0
2804 Cl H CO (Ph-2-Br) 2-Me, 6-Et 0 0
2805 Cl H CO (Ph-2-Br) 2-Me, 6-cPr 0 0
2806 Cl H CO (Ph-2-Br) 2,6-cPr ₂ 0 0
2807 Cl H CO (Ph-2-Br) 2-cPr, 3,5-Me ₂ 0 0
2808 Cl H CO (Ph-2-Br) 2-cPr, 3,6-Me ₂ 0 0
2809 Cl H CO (Ph-2-I) 2-Me 0 0
2810 Cl H CO (Ph-2-I) 2-iPr 0 0
2811 Cl H CO (Ph-2-I) 2-cPr 0 0
2812 Cl H CO (Ph-2-I) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2813 Cl H CO (Ph-2-I) 2,6-Me ₂ 0 0
2814 Cl H CO (Ph-2-I) 2-Me, 6-cPr 0 0
2815 Cl H CO (Ph-2-CF _Three ) 2-Me 0 0
2816 Cl H CO (Ph-2-CF _Three ) 2-iPr 0 0
2817 Cl H CO (Ph-2-CF _Three ) 2-cPr 0 0
2818 Cl H CO (Ph-2-CF _Three ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2819 Cl H CO (Ph-2-CF _Three ) 2,6-Me ₂ 0 0
2820 Cl H CO (Ph-2-CF _Three ) 2-Me, 6-cPr 0 0
2821 Cl H CO (Ph-2-CH ₂ Ph) 2-Me 0 0
2822 Cl H CO (Ph-2-CH ₂ Ph) 2-iPr 0 0
2823 Cl H CO (Ph-2-CH ₂ Ph) 2-cPr 0 0
2824 Cl H CO (Ph-2-CH ₂ Ph) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2825 Cl H CO (Ph-2-CH ₂ Ph) 2,6-Me ₂ 0 0
2826 Cl H CO (Ph-2-CH ₂ Ph) 2-Me, 6-cPr 0 0
2827 Cl H CO (Ph-2-CO ₂ Q ⁶ ) 2-Me 0 0
2828 Cl H CO (Ph-2-CO ₂ Q ¹² ) 2-Me 0 0
2829 Cl H CO (Ph-2-CO ₂ Q ¹³ ) 2-Me 0 0
2830 Cl H CO (Ph-2-CO ₂ Q ¹⁴ ) 2-Me 0 0
2831 Cl H CO (Ph-2-CO ₂ Q ¹⁵ ) 2-Me 0 0
2832 Cl H CO (Ph-2-CO ₂ Q ¹⁶ ) 2-Me 0 0
2833 Cl H CO (Ph-2-CO ₂ Q ¹⁷ ) 2-Me 0 0
2834 Cl H CO (Ph-2-CO ₂ Q ⁷ ) 2-iPr 0 0
2835 Cl H CO (Ph-2-CO ₂ Q ⁸ ) 2-cPr 0 0
2836 Cl H CO (Ph-2-CO ₂ Q ⁹ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2837 Cl H CO (Ph-2-CO ₂ Q ^Ten ) 2,6-Me ₂ 0 0
2838 Cl H CO (Ph-2-CO ₂ Q ¹¹ ) 2-Me, 6-cPr 0 0
2839 Cl H CO (Ph-2-CO ₂ Q ¹² ) 2-Me, 6-cPr 0 0
2840 Cl H CO (Ph-2-CO ₂ Q ¹³ ) 2-Me, 6-cPr 0 0
2841 Cl H CO (Ph-2-CO ₂ Q ¹⁴ ) 2-Me, 6-cPr 0 0
2842 Cl H CO (Ph-2-CO ₂ Q ¹⁵ ) 2-Me, 6-cPr 0 0
2843 Cl H CO (Ph-2-CO ₂ Q ¹⁶ ) 2-Me, 6-cPr 0 0
2844 Cl H CO (Ph-2-CO ₂ Q ¹⁷ ) 2-Me, 6-cPr 0 0
2845 Cl H CO (Ph-2-NO ₂ ) 2-Me 0 0
2846 Cl H CO (Ph-2-NO ₂ ) 2-iPr 0 0
2847 Cl H CO (Ph-2-NO ₂ ) 2-cPr 0 0
2848 Cl H CO (Ph-2-NO ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2849 Cl H CO (Ph-2-NO ₂ ) 2,6-Me ₂ 0 0
2850 Cl H CO (Ph-2-NO ₂ ) 2-Me, 6-cPr 0 0
2851 Cl H CO (Ph-2-OPh) 2-Me 0 0
2852 Cl H CO (Ph-2-OPh) 2-iPr 0 0
2853 Cl H CO (Ph-2-OPh) 2-cPr 0 0
2854 Cl H CO (Ph-2-OPh) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2855 Cl H CO (Ph-2-OPh) 2,6-Me ₂ 0 0
2856 Cl H CO (Ph-2-OPh) 2-Me, 6-cPr 0 0
2857 Cl H CO (Ph-3-F) 2-Me 0 0
2858 Cl H CO (Ph-3-F) 2-iPr 0 0
2859 Cl H CO (Ph-3-F) 2-cPr 0 0
2860 Cl H CO (Ph-3-F) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2861 Cl H CO (Ph-3-F) 2,6-Me ₂ 0 0
2862 Cl H CO (Ph-3-F) 2-Me, 6-cPr 0 0
2863 Cl H CO (Ph-3-Cl) 2-Me 0 0
2864 Cl H CO (Ph-3-Cl) 2-iPr 0 0
2865 Cl H CO (Ph-3-Cl) 2-cPr 0 0
2866 Cl H CO (Ph-3-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2867 Cl H CO (Ph-3-Cl) 2,6-Me ₂ 0 0
2868 Cl H CO (Ph-3-Cl) 2-Me, 6-cPr 0 0
2869 Cl H CO (Ph-3-Br) 2-Me 0 0
2870 Cl H CO (Ph-3-Br) 2-iPr 0 0
2871 Cl H CO (Ph-3-Br) 2-cPr 0 0
2872 Cl H CO (Ph-3-Br) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2873 Cl H CO (Ph-3-Br) 2,6-Me ₂ 0 0
2874 Cl H CO (Ph-3-Br) 2-Me, 6-cPr 0 0
2875 Cl H CO (Ph-3-I) 2-Me 0 0
2876 Cl H CO (Ph-3-I) 2-iPr 0 0
2877 Cl H CO (Ph-3-I) 2-cPr 0 0
2878 Cl H CO (Ph-3-I) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2879 Cl H CO (Ph-3-I) 2,6-Me ₂ 0 0
2880 Cl H CO (Ph-3-I) 2-Me, 6-cPr 0 0
2881 Cl H CO (Ph-3-Me) 2-Cl 0 0
2882 Cl H CO (Ph-3-Me) 2-Br 0 0
2883 Cl H CO (Ph-3-Me) 2-I 0 0
2884 Cl H CO (Ph-3-Me) 2-cBu 0 0
2885 Cl H CO (Ph-3-Me) 2-cPr, 5-Me 0 0
2886 Cl H CO (Ph-3-Me) 2-OMe, 5-Me 0 0
2887 Cl H CO (Ph-3-Me) 2-F, 6-iPr 0 0
2888 Cl H CO (Ph-3-Me) 2-Cl, 6-cPr 0 0
2889 Cl H CO (Ph-3-Me) 2-Br, 6-Me 0 0
2890 Cl H CO (Ph-3-Me) 2-I, 6-Me 0 0
2891 Cl H CO (Ph-3-Me) 2-Me, 6-Et 0 0
2892 Cl H CO (Ph-3-Me) 2,6-cPr ₂ 0 0
2893 Cl H CO (Ph-3-Me) 2-cPr, 3,5-Me ₂ 0 0
2894 Cl H CO (Ph-3-Me) 2-cPr, 3,6-Me ₂ 0 0
2895 Cl H CO (Ph-3-CF _Three ) 2-Me 0 0
2896 Cl H CO (Ph-3-CF _Three ) 2-iPr 0 0
2897 Cl H CO (Ph-3-CF _Three ) 2-cPr 0 0
2898 Cl H CO (Ph-3-CF _Three ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2899 Cl H CO (Ph-3-CF _Three ) 2,6-Me ₂ 0 0
2900 Cl H CO (Ph-3-CF _Three ) 2-Me, 6-cPr 0 0
2901 Cl H CO (Ph-3-CO ₂ Q ⁶ ) 2-Me 0 0
2902 Cl H CO (Ph-3-CO ₂ Q ⁷ ) 2-iPr 0 0
2903 Cl H CO (Ph-3-CO ₂ Q ⁸ ) 2-cPr 0 0
2904 Cl H CO (Ph-3-CO ₂ Q ⁹ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2905 Cl H CO (Ph-3-CO ₂ Q ^Ten ) 2,6-Me ₂ 0 0
2906 Cl H CO (Ph-3-CO ₂ Q ¹¹ ) 2-Me, 6-cPr 0 0
2907 Cl H CO (Ph-3-CO ₂ Q ¹² ) 2-Me, 6-cPr 0 0
2908 Cl H CO (Ph-3-CO ₂ Q ¹³ ) 2-Me, 6-cPr 0 0
2909 Cl H CO (Ph-3-CO ₂ Q ¹⁴ ) 2-Me, 6-cPr 0 0
2910 Cl H CO (Ph-3-CO ₂ Q ¹⁵ ) 2-Me, 6-cPr 0 0
2911 Cl H CO (Ph-3-CO ₂ Q ¹⁶ ) 2-Me, 6-cPr 0 0
2912 Cl H CO (Ph-3-CO ₂ Q ¹⁷ ) 2-Me, 6-cPr 0 0
2913 Cl H CO (Ph-3-NO ₂ ) 2-Me 0 0
2914 Cl H CO (Ph-3-NO ₂ ) 2-iPr 0 0
2915 Cl H CO (Ph-3-NO ₂ ) 2-cPr 0 0
2916 Cl H CO (Ph-3-NO ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2917 Cl H CO (Ph-3-NO ₂ ) 2,6-Me ₂ 0 0
2918 Cl H CO (Ph-3-NO ₂ ) 2-Me, 6-cPr 0 0
2919 Cl H CO (Ph-3-OPh) 2-Me 0 0
2920 Cl H CO (Ph-3-OPh) 2-iPr 0 0
2921 Cl H CO (Ph-3-OPh) 2-cPr 0 0
2922 Cl H CO (Ph-3-OPh) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2923 Cl H CO (Ph-3-OPh) 2,6-Me ₂ 0 0
2924 Cl H CO (Ph-3-OPh) 2-Me, 6-cPr 0 0
2925 Cl H CO (Ph-4-F) 2-Me 0 0
2926 Cl H CO (Ph-4-F) 2-iPr 0 0
2927 Cl H CO (Ph-4-F) 2-cPr 0 0
2928 Cl H CO (Ph-4-F) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2929 Cl H CO (Ph-4-F) 2,6-Me ₂ 0 0
2930 Cl H CO (Ph-4-F) 2-Me, 6-cPr 0 0
2931 Cl H CO (Ph-4-Br) 2-Cl 0 0
2932 Cl H CO (Ph-4-Br) 2-Br 0 0
2933 Cl H CO (Ph-4-Br) 2-I 0 0
2934 Cl H CO (Ph-4-Br) 2-cBu 0 0
2935 Cl H CO (Ph-4-Br) 2-cPr, 5-Me 0 0
2936 Cl H CO (Ph-4-Br) 2-OMe, 5-Me 0 0
2937 Cl H CO (Ph-4-Br) 2-F, 6-iPr 0 0
2938 Cl H CO (Ph-4-Br) 2-Cl, 6-cPr 0 0
2939 Cl H CO (Ph-4-Br) 2-Br, 6-Me 0 0
2940 Cl H CO (Ph-4-Br) 2-I, 6-Me 0 0
2941 Cl H CO (Ph-4-Br) 2-Me, 6-Et 0 0
2942 Cl H CO (Ph-4-Br) 2,6-cPr ₂ 0 0
2943 Cl H CO (Ph-4-Br) 2-cPr, 3,5-Me ₂ 0 0
2944 Cl H CO (Ph-4-Br) 2-cPr, 3,6-Me ₂ 0 0
2945 Cl H CO (Ph-4-Et) 2-Cl 0 0
2946 Cl H CO (Ph-4-Et) 2-Br 0 0
2947 Cl H CO (Ph-4-Et) 2-I 0 0
2948 Cl H CO (Ph-4-Et) 2-Me 0 0
2949 Cl H CO (Ph-4-Et) 2-iPr 0 0
2950 Cl H CO (Ph-4-Et) 2-cPr 0 0
2951 Cl H CO (Ph-4-Et) 2-cBu 0 0
2952 Cl H CO (Ph-4-Et) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2953 Cl H CO (Ph-4-Et) 2-cPr, 5-Me 0 0
2954 Cl H CO (Ph-4-Et) 2-OMe, 5-Me 0 0
2955 Cl H CO (Ph-4-Et) 2-F, 6-iPr 0 0
2956 Cl H CO (Ph-4-Et) 2-Cl, 6-cPr 0 0
2957 Cl H CO (Ph-4-Et) 2-Br, 6-Me 0 0
2958 Cl H CO (Ph-4-Et) 2-I, 6-Me 0 0
2959 Cl H CO (Ph-4-Et) 2,6-Me ₂ 0 0
2960 Cl H CO (Ph-4-Et) 2-Me, 6-Et 0 0
2961 Cl H CO (Ph-4-Et) 2-Me, 6-cPr 0 0
2962 Cl H CO (Ph-4-Et) 2,6-cPr ₂ 0 0
2963 Cl H CO (Ph-4-Et) 2-cPr, 3,5-Me ₂ 0 0
2964 Cl H CO (Ph-4-Et) 2-cPr, 3,6-Me ₂ 0 0
2965 Cl H CO (Ph-4-Pr) 2-Me 0 0
2966 Cl H CO (Ph-4-Pr) 2-iPr 0 0
2967 Cl H CO (Ph-4-Pr) 2-cPr 0 0
2968 Cl H CO (Ph-4-Pr) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2969 Cl H CO (Ph-4-Pr) 2,6-Me ₂ 0 0
2970 Cl H CO (Ph-4-Pr) 2-Me, 6-cPr 0 0
2971 Cl H CO (Ph-4-iPr) 2-Me 0 0
2972 Cl H CO (Ph-4-iPr) 2-iPr 0 0
2973 Cl H CO (Ph-4-iPr) 2-cPr 0 0
2974 Cl H CO (Ph-4-iPr) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2975 Cl H CO (Ph-4-iPr) 2,6-Me ₂ 0 0
2976 Cl H CO (Ph-4-iPr) 2-Me, 6-cPr 0 0
2977 Cl H CO (Ph-4-Bu) 2-Me 0 0
2978 Cl H CO (Ph-4-Bu) 2-iPr 0 0
2979 Cl H CO (Ph-4-Bu) 2-cPr 0 0
2980 Cl H CO (Ph-4-Bu) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2981 Cl H CO (Ph-4-Bu) 2,6-Me ₂ 0 0
2982 Cl H CO (Ph-4-Bu) 2-Me, 6-cPr 0 0
2983 Cl H CO (Ph-4-CF _Three ) 2-Me 0 0
2984 Cl H CO (Ph-4-CF _Three ) 2-iPr 0 0
2985 Cl H CO (Ph-4-CF _Three ) 2-cPr 0 0
2986 Cl H CO (Ph-4-CF _Three ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2987 Cl H CO (Ph-4-CF _Three ) 2,6-Me ₂ 0 0
2988 Cl H CO (Ph-4-CF _Three ) 2-Me, 6-cPr 0 0
2989 Cl H CO (Ph-4-CN) 2-Me 0 0
2990 Cl H CO (Ph-4-CN) 2-iPr 0 0
2991 Cl H CO (Ph-4-CN) 2-cPr 0 0
2992 Cl H CO (Ph-4-CN) 2-CH ₂ CH ₂ CH ₂ -3 0 0
2993 Cl H CO (Ph-4-CN) 2,6-Me ₂ 0 0
2994 Cl H CO (Ph-4-CN) 2-Me, 6-cPr 0 0
2995 Cl H CO (Ph-4-CO ₂ Q ^Five ) 2-Cl, 6-cPr 0 0
2996 Cl H CO (Ph-4-CO ₂ Q ⁶ ) 2-Me 0 0
2997 Cl H CO (Ph-4-CO ₂ Q ⁷ ) 2-iPr 0 0
2998 Cl H CO (Ph-4-CO ₂ Q ⁸ ) 2-cPr 0 0
2999 Cl H CO (Ph-4-CO ₂ Q ⁹ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3000 Cl H CO (Ph-4-CO ₂ Q ^Ten ) 2,6-Me ₂ 0 0
3001 Cl H CO (Ph-4-CO ₂ Q ¹¹ ) 2-Me, 6-cPr 0 0
3002 Cl H CO (Ph-4-CO ₂ Q ¹² ) 2-Me, 6-cPr 0 0
3003 Cl H CO (Ph-4-CO ₂ Q ¹³ ) 2-Me, 6-cPr 0 0
3004 Cl H CO (Ph-4-CO ₂ Q ¹⁴ ) 2-Me, 6-cPr 0 0
3005 Cl H CO (Ph-4-CO ₂ Q ¹⁵ ) 2-Me, 6-cPr 0 0
3006 Cl H CO (Ph-4-CO ₂ Q ¹⁶ ) 2-Me, 6-cPr 0 0
3007 Cl H CO (Ph-4-CO ₂ Q ¹⁷ ) 2-Me, 6-cPr 0 0
3008 Cl H CO (Ph-2-SO ₂ OQ ^Five ) 2-Me, 6-cPr 0 0
3009 Cl H CO (Ph-3-SO ₂ OQ ^Five ) 2-Me, 6-cPr 0 0
3010 Cl H CO (Ph-4-SO ₂ OQ ^Five ) 2-Me, 6-cPr 0 0
3011 Cl H CO (Ph-4-Ph) 2-Me 0 0
3012 Cl H CO (Ph-4-Ph) 2-iPr 0 0
3013 Cl H CO (Ph-4-Ph) 2-cPr 0 0
3014 Cl H CO (Ph-4-Ph) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3015 Cl H CO (Ph-4-Ph) 2,6-Me ₂ 0 0
3016 Cl H CO (Ph-4-Ph) 2-Me, 6-cPr 0 0
3017 Cl H CO (Ph-4-OCF _Three ) 2-Me 0 0
3018 Cl H CO (Ph-4-OCF _Three ) 2-iPr 0 0
3019 Cl H CO (Ph-4-OCF _Three ) 2-cPr 0 0
3020 Cl H CO (Ph-4-OCF _Three ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3021 Cl H CO (Ph-4-OCF _Three ) 2,6-Me ₂ 0 0
3022 Cl H CO (Ph-4-OCF _Three ) 2-Me, 6-cPr 0 0
3023 Cl H CO (Ph-4-OCH ₂ Ph) 2-Me 0 0
3024 Cl H CO (Ph-4-OCH ₂ Ph) 2-iPr 0 0
3025 Cl H CO (Ph-4-OCH ₂ Ph) 2-cPr 0 0
3026 Cl H CO (Ph-4-OCH ₂ Ph) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3027 Cl H CO (Ph-4-OCH ₂ Ph) 2,6-Me ₂ 0 0
3028 Cl H CO (Ph-4-OCH ₂ Ph) 2-Me, 6-cPr 0 0
3029 Cl H CO (Ph-2,3-F ₂ ) 2-Me 0 0
3030 Cl H CO (Ph-2,3-F ₂ ) 2-iPr 0 0
3031 Cl H CO (Ph-2,3-F ₂ ) 2-cPr 0 0
3032 Cl H CO (Ph-2,3-F ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3033 Cl H CO (Ph-2,3-F ₂ ) 2,6-Me ₂ 0 0
3034 Cl H CO (Ph-2,3-F ₂ ) 2-Me, 6-cPr 0 0
3035 Cl H CO (Ph-2-F-3-CF _Three ) 2-Me 0 0
3036 Cl H CO (Ph-2-F-3-CF _Three ) 2-iPr 0 0
3037 Cl H CO (Ph-2-F-3-CF _Three ) 2-cPr 0 0
3038 Cl H CO (Ph-2-F-3-CF _Three ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3039 Cl H CO (Ph-2-F-3-CF _Three ) 2,6-Me ₂ 0 0
3040 Cl H CO (Ph-2-F-3-CF _Three ) 2-Me, 6-cPr 0 0
3041 Cl H CO (Ph-2,3-Me ₂ ) 2-Me 0 0
3042 Cl H CO (Ph-2,3-Me ₂ ) 2-iPr 0 0
3043 Cl H CO (Ph-2,3-Me ₂ ) 2-cPr 0 0
3044 Cl H CO (Ph-2,3-Me ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3045 Cl H CO (Ph-2,3-Me ₂ ) 2,6-Me ₂ 0 0
3046 Cl H CO (Ph-2,3-Me ₂ ) 2-Me, 6-cPr 0 0
3047 Cl H CO (Ph-2-Me-3-Cl) 2-Me 0 0
3048 Cl H CO (Ph-2-Me-3-Cl) 2-iPr 0 0
3049 Cl H CO (Ph-2-Me-3-Cl) 2-cPr 0 0
3050 Cl H CO (Ph-2-Me-3-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3051 Cl H CO (Ph-2-Me-3-Cl) 2,6-Me ₂ 0 0
3052 Cl H CO (Ph-2-Me-3-Cl) 2-Me, 6-cPr 0 0
3053 Cl H CO (Ph-2,4-F ₂ ) 2-Me 0 0
3054 Cl H CO (Ph-2,4-F ₂ ) 2-iPr 0 0
3055 Cl H CO (Ph-2,4-F ₂ ) 2-cPr 0 0
3056 Cl H CO (Ph-2,4-F ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3057 Cl H CO (Ph-2,4-F ₂ ) 2,6-Me ₂ 0 0
3058 Cl H CO (Ph-2,4-F ₂ ) 2-Me, 6-cPr 0 0
3059 Cl H CO (Ph-2-F-4-Cl) 2-Me 0 0
3060 Cl H CO (Ph-2-F-4-Cl) 2-iPr 0 0
3061 Cl H CO (Ph-2-F-4-Cl) 2-cPr 0 0
3062 Cl H CO (Ph-2-F-4-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3063 Cl H CO (Ph-2-F-4-Cl) 2,6-Me ₂ 0 0
3064 Cl H CO (Ph-2-F-4-Cl) 2-Me, 6-cPr 0 0
3065 Cl H CO (Ph-2-F-4-CF _Three ) 2-Me 0 0
3066 Cl H CO (Ph-2-F-4-CF _Three ) 2-iPr 0 0
3067 Cl H CO (Ph-2-F-4-CF _Three ) 2-cPr 0 0
3068 Cl H CO (Ph-2-F-4-CF _Three ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3069 Cl H CO (Ph-2-F-4-CF _Three ) 2,6-Me ₂ 0 0
3070 Cl H CO (Ph-2-F-4-CF _Three ) 2-Me, 6-cPr 0 0
3071 Cl H CO (Ph-2-Cl-4-F) 2-Me 0 0
3072 Cl H CO (Ph-2-Cl-4-F) 2-iPr 0 0
3073 Cl H CO (Ph-2-Cl-4-F) 2-cPr 0 0
3074 Cl H CO (Ph-2-Cl-4-F) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3075 Cl H CO (Ph-2-Cl-4-F) 2,6-Me ₂ 0 0
3076 Cl H CO (Ph-2-Cl-4-F) 2-Me, 6-cPr 0 0
3077 Cl H CO (Ph-2-Cl-4-Br) 2-Me 0 0
3078 Cl H CO (Ph-2-Cl-4-Br) 2-iPr 0 0
3079 Cl H CO (Ph-2-Cl-4-Br) 2-cPr 0 0
3080 Cl H CO (Ph-2-Cl-4-Br) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3081 Cl H CO (Ph-2-Cl-4-Br) 2,6-Me ₂ 0 0
3082 Cl H CO (Ph-2-Cl-4-Br) 2-Me, 6-cPr 0 0
3083 Cl H CO (Ph-2-Me-4-Br) 2-Me 0 0
3084 Cl H CO (Ph-2-Me-4-Br) 2-iPr 0 0
3085 Cl H CO (Ph-2-Me-4-Br) 2-cPr 0 0
3086 Cl H CO (Ph-2-Me-4-Br) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3087 Cl H CO (Ph-2-Me-4-Br) 2,6-Me ₂ 0 0
3088 Cl H CO (Ph-2-Me-4-Br) 2-Me, 6-cPr 0 0
3089 Cl H CO (Ph-2,4-Me ₂ ) 2-Me 0 0
3090 Cl H CO (Ph-2,4-Me ₂ ) 2-iPr 0 0
3091 Cl H CO (Ph-2,4-Me ₂ ) 2-cPr 0 0
3092 Cl H CO (Ph-2,4-Me ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3093 Cl H CO (Ph-2,4-Me ₂ ) 2,6-Me ₂ 0 0
3094 Cl H CO (Ph-2,4-Me ₂ ) 2-Me, 6-cPr 0 0
3095 Cl H CO (Ph-2,5-Cl ₂ ) 2-Me 0 0
3096 Cl H CO (Ph-2,5-Cl ₂ ) 2-iPr 0 0
3097 Cl H CO (Ph-2,5-Cl ₂ ) 2-cPr 0 0
3098 Cl H CO (Ph-2,5-Cl ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3099 Cl H CO (Ph-2,5-Cl ₂ ) 2,6-Me ₂ 0 0
3100 Cl H CO (Ph-2,5-Cl ₂ ) 2-Me, 6-cPr 0 0
3101 Cl H CO (Ph-2-Cl-5-Br) 2-Me 0 0
3102 Cl H CO (Ph-2-Cl-5-Br) 2-iPr 0 0
3103 Cl H CO (Ph-2-Cl-5-Br) 2-cPr 0 0
3104 Cl H CO (Ph-2-Cl-5-Br) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3105 Cl H CO (Ph-2-Cl-5-Br) 2,6-Me ₂ 0 0
3106 Cl H CO (Ph-2-Cl-5-Br) 2-Me, 6-cPr 0 0
3107 Cl H CO (Ph-2-Br-5-OMe) 2-Me 0 0
3108 Cl H CO (Ph-2-Br-5-OMe) 2-iPr 0 0
3109 Cl H CO (Ph-2-Br-5-OMe) 2-cPr 0 0
3110 Cl H CO (Ph-2-Br-5-OMe) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3111 Cl H CO (Ph-2-Br-5-OMe) 2,6-Me ₂ 0 0
3112 Cl H CO (Ph-2-Br-5-OMe) 2-Me, 6-cPr 0 0
3113 Cl H CO (Ph-2,5-Me ₂ ) 2-Cl 0 0
3114 Cl H CO (Ph-2,5-Me ₂ ) 2-Br 0 0
3115 Cl H CO (Ph-2,5-Me ₂ ) 2-I 0 0
3116 Cl H CO (Ph-2,5-Me ₂ ) 2-Me 0 0
3117 Cl H CO (Ph-2,5-Me ₂ ) 2-iPr 0 0
3118 Cl H CO (Ph-2,5-Me ₂ ) 2-cPr 0 0
3119 Cl H CO (Ph-2,5-Me ₂ ) 2-cBu 0 0
3120 Cl H CO (Ph-2,5-Me ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3121 Cl H CO (Ph-2,5-Me ₂ ) 2-cPr, 5-Me 0 0
3122 Cl H CO (Ph-2,5-Me ₂ ) 2-OMe, 5-Me 0 0
3123 Cl H CO (Ph-2,5-Me ₂ ) 2-F, 6-iPr 0 0
3124 Cl H CO (Ph-2,5-Me ₂ ) 2-Cl, 6-cPr 0 0
3125 Cl H CO (Ph-2,5-Me ₂ ) 2-Br, 6-Me 0 0
3126 Cl H CO (Ph-2,5-Me ₂ ) 2-I, 6-Me 0 0
3127 Cl H CO (Ph-2,5-Me ₂ ) 2,6-Me ₂ 0 0
3128 Cl H CO (Ph-2,5-Me ₂ ) 2-Me, 6-Et 0 0
3129 Cl H CO (Ph-2,5-Me ₂ ) 2-Me, 6-cPr 0 0
3130 Cl H CO (Ph-2,5-Me ₂ ) 2,6-cPr ₂ 0 0
3131 Cl H CO (Ph-2,5-Me ₂ ) 2-cPr, 3,5-Me ₂ 0 0
3132 Cl H CO (Ph-2,5-Me ₂ ) 2-cPr, 3,6-Me ₂ 0 0
3133 Cl H CO (Ph-2,6-F ₂ ) 2-Me 0 0
3134 Cl H CO (Ph-2,6-F ₂ ) 2-iPr 0 0
3135 Cl H CO (Ph-2,6-F ₂ ) 2-cPr 0 0
3136 Cl H CO (Ph-2,6-F ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3137 Cl H CO (Ph-2,6-F ₂ ) 2,6-Me ₂ 0 0
3138 Cl H CO (Ph-2,6-F ₂ ) 2-Me, 6-cPr 0 0
3139 Cl H CO (Ph-2-F-6-Cl) 2-Me 0 0
3140 Cl H CO (Ph-2-F-6-Cl) 2-iPr 0 0
3141 Cl H CO (Ph-2-F-6-Cl) 2-cPr 0 0
3142 Cl H CO (Ph-2-F-6-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3143 Cl H CO (Ph-2-F-6-Cl) 2,6-Me ₂ 0 0
3144 Cl H CO (Ph-2-F-6-Cl) 2-Me, 6-cPr 0 0
3145 Cl H CO (Ph-2,6-Cl ₂ ) 2-Me 0 0
3146 Cl H CO (Ph-2,6-Cl ₂ ) 2-iPr 0 0
3147 Cl H CO (Ph-2,6-Cl ₂ ) 2-cPr 0 0
3148 Cl H CO (Ph-2,6-Cl ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3149 Cl H CO (Ph-2,6-Cl ₂ ) 2,6-Me ₂ 0 0
3150 Cl H CO (Ph-2,6-Cl ₂ ) 2-Me, 6-cPr 0 0
3151 Cl H CO (Ph-2,6-Me ₂ ) 2-Me 0 0
3152 Cl H CO (Ph-2,6-Me ₂ ) 2-iPr 0 0
3153 Cl H CO (Ph-2,6-Me ₂ ) 2-cPr 0 0
3154 Cl H CO (Ph-2,6-Me ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3155 Cl H CO (Ph-2,6-Me ₂ ) 2,6-Me ₂ 0 0
3156 Cl H CO (Ph-2,6-Me ₂ ) 2-Me, 6-cPr 0 0
3157 Cl H CO {Ph-2,6- (OMe) ₂ } 2-Me 0 0
3158 Cl H CO {Ph-2,6- (OMe) ₂ } 2-iPr 0 0
3159 Cl H CO {Ph-2,6- (OMe) ₂ } 2-cPr 0 0
3160 Cl H CO {Ph-2,6- (OMe) ₂ } 2-CH ₂ CH ₂ CH ₂ -3 0 0
3161 Cl H CO {Ph-2,6- (OMe) ₂ } 2,6-Me ₂ 0 0
3162 Cl H CO {Ph-2,6- (OMe) ₂ } 2-Me, 6-cPr 0 0
3163 Cl H CO (Ph-3,4-F ₂ ) 2-Me 0 0
3164 Cl H CO (Ph-3,4-F ₂ ) 2-iPr 0 0
3165 Cl H CO (Ph-3,4-F ₂ ) 2-cPr 0 0
3166 Cl H CO (Ph-3,4-F ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3167 Cl H CO (Ph-3,4-F ₂ ) 2,6-Me ₂ 0 0
3168 Cl H CO (Ph-3,4-F ₂ ) 2-Me, 6-cPr 0 0
3169 Cl H CO (Ph-3-F-4-Me) 2-Cl 0 0
3170 Cl H CO (Ph-3-F-4-Me) 2-Br 0 0
3171 Cl H CO (Ph-3-F-4-Me) 2-I 0 0
3172 Cl H CO (Ph-3-F-4-Me) 2-Me 0 0
3173 Cl H CO (Ph-3-F-4-Me) 2-iPr 0 0
3174 Cl H CO (Ph-3-F-4-Me) 2-cPr 0 0
3175 Cl H CO (Ph-3-F-4-Me) 2-cBu 0 0
3176 Cl H CO (Ph-3-F-4-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3177 Cl H CO (Ph-3-F-4-Me) 2-cPr, 5-Me 0 0
3178 Cl H CO (Ph-3-F-4-Me) 2-OMe, 5-Me 0 0
3179 Cl H CO (Ph-3-F-4-Me) 2-F, 6-iPr 0 0
3180 Cl H CO (Ph-3-F-4-Me) 2-Cl, 6-cPr 0 0
3181 Cl H CO (Ph-3-F-4-Me) 2-Br, 6-Me 0 0
3182 Cl H CO (Ph-3-F-4-Me) 2-I, 6-Me 0 0
3183 Cl H CO (Ph-3-F-4-Me) 2,6-Me ₂ 0 0
3184 Cl H CO (Ph-3-F-4-Me) 2-Me, 6-Et 0 0
3185 Cl H CO (Ph-3-F-4-Me) 2-Me, 6-cPr 0 0
3186 Cl H CO (Ph-3-F-4-Me) 2,6-cPr ₂ 0 0
3187 Cl H CO (Ph-3-F-4-Me) 2-cPr, 3,5-Me ₂ 0 0
3188 Cl H CO (Ph-3-F-4-Me) 2-cPr, 3,6-Me ₂ 0 0
3189 Cl H CO (Ph-3,4-Cl ₂ ) 2-Me 0 0
3190 Cl H CO (Ph-3,4-Cl ₂ ) 2-iPr 0 0
3191 Cl H CO (Ph-3,4-Cl ₂ ) 2-cPr 0 0
3192 Cl H CO (Ph-3,4-Cl ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3193 Cl H CO (Ph-3,4-Cl ₂ ) 2,6-Me ₂ 0 0
3194 Cl H CO (Ph-3,4-Cl ₂ ) 2-Me, 6-cPr 0 0
3195 Cl H CO (Ph-3-NO ₂ -4-Cl) 2-Me 0 0
3196 Cl H CO (Ph-3-NO ₂ -4-Cl) 2-iPr 0 0
3197 Cl H CO (Ph-3-NO ₂ -4-Cl) 2-cPr 0 0
3198 Cl H CO (Ph-3-NO ₂ -4-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3199 Cl H CO (Ph-3-NO ₂ -4-Cl) 2,6-Me ₂ 0 0
3200 Cl H CO (Ph-3-NO ₂ -4-Cl) 2-Me, 6-cPr 0 0
3201 Cl H CO (Ph-3,5-F ₂ ) 2-Cl 0 0
3202 Cl H CO (Ph-3,5-F ₂ ) 2-Br 0 0
3203 Cl H CO (Ph-3,5-F ₂ ) 2-I 0 0
3204 Cl H CO (Ph-3,5-F ₂ ) 2-Me 0 0
3205 Cl H CO (Ph-3,5-F ₂ ) 2-iPr 0 0
3206 Cl H CO (Ph-3,5-F ₂ ) 2-cPr 0 0
3207 Cl H CO (Ph-3,5-F ₂ ) 2-cBu 0 0
3208 Cl H CO (Ph-3,5-F ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3209 Cl H CO (Ph-3,5-F ₂ ) 2-cPr, 5-Me 0 0
3210 Cl H CO (Ph-3,5-F ₂ ) 2-OMe, 5-Me 0 0
3211 Cl H CO (Ph-3,5-F ₂ ) 2-F, 6-iPr 0 0
3212 Cl H CO (Ph-3,5-F ₂ ) 2-Cl, 6-cPr 0 0
3213 Cl H CO (Ph-3,5-F ₂ ) 2-Br, 6-Me 0 0
3214 Cl H CO (Ph-3,5-F ₂ ) 2-I, 6-Me 0 0
3215 Cl H CO (Ph-3,5-F ₂ ) 2,6-Me ₂ 0 0
3216 Cl H CO (Ph-3,5-F ₂ ) 2-Me, 6-Et 0 0
3217 Cl H CO (Ph-3,5-F ₂ ) 2-Me, 6-cPr 0 0
3218 Cl H CO (Ph-3,5-F ₂ ) 2,6-cPr ₂ 0 0
3219 Cl H CO (Ph-3,5-F ₂ ) 2-cPr, 3,5-Me ₂ 0 0
3220 Cl H CO (Ph-3,5-F ₂ ) 2-cPr, 3,6-Me ₂ 0 0
3221 Cl H CO (Ph-3,5-Cl ₂ ) 2-Me 0 0
3222 Cl H CO (Ph-3,5-Cl ₂ ) 2-iPr 0 0
3223 Cl H CO (Ph-3,5-Cl ₂ ) 2-cPr 0 0
3224 Cl H CO (Ph-3,5-Cl ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3225 Cl H CO (Ph-3,5-Cl ₂ ) 2,6-Me ₂ 0 0
3226 Cl H CO (Ph-3,5-Cl ₂ ) 2-Me, 6-cPr 0 0
3227 Cl H CO (Ph-3,5-Me ₂ ) 2-Cl 0 0
3228 Cl H CO (Ph-3,5-Me ₂ ) 2-Br 0 0
3229 Cl H CO (Ph-3,5-Me ₂ ) 2-I 0 0
3230 Cl H CO (Ph-3,5-Me ₂ ) 2-Me 0 0
3231 Cl H CO (Ph-3,5-Me ₂ ) 2-iPr 0 0
3232 Cl H CO (Ph-3,5-Me ₂ ) 2-cPr 0 0
3233 Cl H CO (Ph-3,5-Me ₂ ) 2-cBu 0 0
3234 Cl H CO (Ph-3,5-Me ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3235 Cl H CO (Ph-3,5-Me ₂ ) 2-cPr, 5-Me 0 0
3236 Cl H CO (Ph-3,5-Me ₂ ) 2-OMe, 5-Me 0 0
3237 Cl H CO (Ph-3,5-Me ₂ ) 2-F, 6-iPr 0 0
3238 Cl H CO (Ph-3,5-Me ₂ ) 2-Cl, 6-cPr 0 0
3239 Cl H CO (Ph-3,5-Me ₂ ) 2-Br, 6-Me 0 0
3240 Cl H CO (Ph-3,5-Me ₂ ) 2-I, 6-Me 0 0
3241 Cl H CO (Ph-3,5-Me ₂ ) 2,6-Me ₂ 0 0
3242 Cl H CO (Ph-3,5-Me ₂ ) 2-Me, 6-Et 0 0
3243 Cl H CO (Ph-3,5-Me ₂ ) 2-Me, 6-cPr 0 0
3244 Cl H CO (Ph-3,5-Me ₂ ) 2,6-cPr ₂ 0 0
3245 Cl H CO (Ph-3,5-Me ₂ ) 2-cPr, 3,5-Me ₂ 0 0
3246 Cl H CO (Ph-3,5-Me ₂ ) 2-cPr, 3,6-Me ₂ 0 0
3247 Cl H CO {Ph-3,5- (OMe) ₂ } 2-Me 0 0
3248 Cl H CO {Ph-3,5- (OMe) ₂ } 2-iPr 0 0
3249 Cl H CO {Ph-3,5- (OMe) ₂ } 2-cPr 0 0
3250 Cl H CO {Ph-3,5- (OMe) ₂ } 2-CH ₂ CH ₂ CH ₂ -3 0 0
3251 Cl H CO {Ph-3,5- (OMe) ₂ } 2,6-Me ₂ 0 0
3252 Cl H CO {Ph-3,5- (OMe) ₂ } 2-Me, 6-cPr 0 0
3253 Cl H CO (Ph-2,4,6-Cl _Three ) 2-Me 0 0
3254 Cl H CO (Ph-2,4,6-Cl _Three ) 2-iPr 0 0
3255 Cl H CO (Ph-2,4,6-Cl _Three ) 2-cPr 0 0
3256 Cl H CO (Ph-2,4,6-Cl _Three ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3257 Cl H CO (Ph-2,4,6-Cl _Three ) 2,6-Me ₂ 0 0
3258 Cl H CO (Ph-2,4,6-Cl _Three ) 2-Me, 6-cPr 0 0
3259 Cl H CO {Ph-3,4,5- (OMe) _Three } 2-Me 0 0
3260 Cl H CO {Ph-3,4,5- (OMe) _Three } 2-iPr 0 0
3261 Cl H CO {Ph-3,4,5- (OMe) _Three } 2-cPr 0 0
3262 Cl H CO {Ph-3,4,5- (OMe) _Three } 2-CH ₂ CH ₂ CH ₂ -3 0 0
3263 Cl H CO {Ph-3,4,5- (OMe) _Three } 2,6-Me ₂ 0 0
3264 Cl H CO {Ph-3,4,5- (OMe) _Three } 2-Me, 6-cPr 0 0
3265 Cl H CO (1-Np) 2-Me 0 0
3266 Cl H CO (1-Np) 2-iPr 0 0
3267 Cl H CO (1-Np) 2-cPr 0 0
3268 Cl H CO (1-Np) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3269 Cl H CO (1-Np) 2,6-Me ₂ 0 0
3270 Cl H CO (1-Np) 2-Me, 6-cPr 0 0
3271 Cl H CO (2-Np) 2-Me 0 0
3272 Cl H CO (2-Np) 2-iPr 0 0
3273 Cl H CO (2-Np) 2-cPr 0 0
3274 Cl H CO (2-Np) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3275 Cl H CO (2-Np) 2,6-Me ₂ 0 0
3276 Cl H CO (2-Np) 2-Me, 6-cPr 0 0
3277 Cl H CO (2-Pyrr-1-Me) 2-Me 0 0
3278 Cl H CO (2-Pyrr-1-Me) 2-iPr 0 0
3279 Cl H CO (2-Pyrr-1-Me) 2-cPr 0 0
3280 Cl H CO (2-Pyrr-1-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3281 Cl H CO (2-Pyrr-1-Me) 2,6-Me ₂ 0 0
3282 Cl H CO (2-Pyrr-1-Me) 2-Me, 6-cPr 0 0
3283 Cl H CO (2-Fur-5-Br) 2-Me 0 0
3284 Cl H CO (2-Fur-5-Br) 2-iPr 0 0
3285 Cl H CO (2-Fur-5-Br) 2-cPr 0 0
3286 Cl H CO (2-Fur-5-Br) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3287 Cl H CO (2-Fur-5-Br) 2,6-Me ₂ 0 0
3288 Cl H CO (2-Fur-5-Br) 2-Me, 6-cPr 0 0
3289 Cl H CO (3-Fur) 2-Me 0 0
3290 Cl H CO (3-Fur) 2-iPr 0 0
3291 Cl H CO (3-Fur) 2-cPr 0 0
3292 Cl H CO (3-Fur) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3293 Cl H CO (3-Fur) 2,6-Me ₂ 0 0
3294 Cl H CO (3-Fur) 2-Me, 6-cPr 0 0
3295 Cl H CO (3-Fur-2-Me-5-tBu) 2-Me 0 0
3296 Cl H CO (3-Fur-2-Me-5-tBu) 2-iPr 0 0
3297 Cl H CO (3-Fur-2-Me-5-tBu) 2-cPr 0 0
3298 Cl H CO (3-Fur-2-Me-5-tBu) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3299 Cl H CO (3-Fur-2-Me-5-tBu) 2,6-Me ₂ 0 0
3300 Cl H CO (3-Fur-2-Me-5-tBu) 2-Me, 6-cPr 0 0
3301 Cl H CO (3-Fur-2-CF _Three -5-Me) 2-Me 0 0
3302 Cl H CO (3-Fur-2-CF _Three -5-Me) 2-iPr 0 0
3303 Cl H CO (3-Fur-2-CF _Three -5-Me) 2-cPr 0 0
3304 Cl H CO (3-Fur-2-CF _Three -5-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3305 Cl H CO (3-Fur-2-CF _Three -5-Me) 2,6-Me ₂ 0 0
3306 Cl H CO (3-Fur-2-CF _Three -5-Me) 2-Me, 6-cPr 0 0
3307 Cl H CO {3-Fur-2-CF _Three -5- (Ph-4-Cl)} 2-Me 0 0
3308 Cl H CO {3-Fur-2-CF _Three -5- (Ph-4-Cl)} 2-iPr 0 0
3309 Cl H CO {3-Fur-2-CF _Three -5- (Ph-4-Cl)} 2-cPr 0 0
3310 Cl H CO {3-Fur-2-CF _Three -5- (Ph-4-Cl)} 2-CH ₂ CH ₂ CH ₂ -3 0 0
3311 Cl H CO {3-Fur-2-CF _Three -5- (Ph-4-Cl)} 2,6-Me ₂ 0 0
3312 Cl H CO {3-Fur-2-CF _Three -5- (Ph-4-Cl)} 2-Me, 6-cPr 0 0
3313 Cl H CO (2-Thi-3-Cl) 2-Me 0 0
3314 Cl H CO (2-Thi-3-Cl) 2-iPr 0 0
3315 Cl H CO (2-Thi-3-Cl) 2-cPr 0 0
3316 Cl H CO (2-Thi-3-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3317 Cl H CO (2-Thi-3-Cl) 2,6-Me ₂ 0 0
3318 Cl H CO (2-Thi-3-Cl) 2-Me, 6-cPr 0 0
3319 Cl H CO (2-Thi-3-Me) 2-Me 0 0
3320 Cl H CO (2-Thi-3-Me) 2-iPr 0 0
3321 Cl H CO (2-Thi-3-Me) 2-cPr 0 0
3322 Cl H CO (2-Thi-3-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3323 Cl H CO (2-Thi-3-Me) 2,6-Me ₂ 0 0
3324 Cl H CO (2-Thi-3-Me) 2-Me, 6-cPr 0 0
3325 Cl H CO (2-Thi-3-OEt) 2-Me 0 0
3326 Cl H CO (2-Thi-3-OEt) 2-iPr 0 0
3327 Cl H CO (2-Thi-3-OEt) 2-cPr 0 0
3328 Cl H CO (2-Thi-3-OEt) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3329 Cl H CO (2-Thi-3-OEt) 2,6-Me ₂ 0 0
3330 Cl H CO (2-Thi-3-OEt) 2-Me, 6-cPr 0 0
3331 Cl H CO (2-Thi-5-Cl) 2-Me 0 0
3332 Cl H CO (2-Thi-5-Cl) 2-iPr 0 0
3333 Cl H CO (2-Thi-5-Cl) 2-cPr 0 0
3334 Cl H CO (2-Thi-5-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3335 Cl H CO (2-Thi-5-Cl) 2,6-Me ₂ 0 0
3336 Cl H CO (2-Thi-5-Cl) 2-Me, 6-cPr 0 0
3337 Cl H CO (2-Thi-5-Br) 2-Me 0 0
3338 Cl H CO (2-Thi-5-Br) 2-iPr 0 0
3339 Cl H CO (2-Thi-5-Br) 2-cPr 0 0
3340 Cl H CO (2-Thi-5-Br) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3341 Cl H CO (2-Thi-5-Br) 2,6-Me ₂ 0 0
3342 Cl H CO (2-Thi-5-Br) 2-Me, 6-cPr 0 0
3343 Cl H CO (2-Thi-5-Me) 2-Me 0 0
3344 Cl H CO (2-Thi-5-Me) 2-iPr 0 0
3345 Cl H CO (2-Thi-5-Me) 2-cPr 0 0
3346 Cl H CO (2-Thi-5-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3347 Cl H CO (2-Thi-5-Me) 2,6-Me ₂ 0 0
3348 Cl H CO (2-Thi-5-Me) 2-Me, 6-cPr 0 0
3349 Cl H CO (2-Thi-5-COMe) 2-Me 0 0
3350 Cl H CO (2-Thi-5-COMe) 2-iPr 0 0
3351 Cl H CO (2-Thi-5-COMe) 2-cPr 0 0
3352 Cl H CO (2-Thi-5-COMe) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3353 Cl H CO (2-Thi-5-COMe) 2,6-Me ₂ 0 0
3354 Cl H CO (2-Thi-5-COMe) 2-Me, 6-cPr 0 0
3355 Cl H CO (3-Thi-5-NO ₂ ) 2-Me 0 0
3356 Cl H CO (3-Thi-5-NO ₂ ) 2-iPr 0 0
3357 Cl H CO (3-Thi-5-NO ₂ ) 2-cPr 0 0
3358 Cl H CO (3-Thi-5-NO ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3359 Cl H CO (3-Thi-5-NO ₂ ) 2,6-Me ₂ 0 0
3360 Cl H CO (3-Thi-5-NO ₂ ) 2-Me, 6-cPr 0 0
3361 Cl H CO (2-Thi-4,5-Br ₂ ) 2-Me 0 0
3362 Cl H CO (2-Thi-4,5-Br ₂ ) 2-iPr 0 0
3363 Cl H CO (2-Thi-4,5-Br ₂ ) 2-cPr 0 0
3364 Cl H CO (2-Thi-4,5-Br ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3365 Cl H CO (2-Thi-4,5-Br ₂ ) 2,6-Me ₂ 0 0
3366 Cl H CO (2-Thi-4,5-Br ₂ ) 2-Me, 6-cPr 0 0
3367 Cl H CO (3-Thi) 2-Me 0 0
3368 Cl H CO (3-Thi) 2-iPr 0 0
3369 Cl H CO (3-Thi) 2-cPr 0 0
3370 Cl H CO (3-Thi) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3371 Cl H CO (3-Thi) 2,6-Me ₂ 0 0
3372 Cl H CO (3-Thi) 2-Me, 6-cPr 0 0
3373 Cl H CO (3-Thi-4-OMe) 2-Me 0 0
3374 Cl H CO (3-Thi-4-OMe) 2-iPr 0 0
3375 Cl H CO (3-Thi-4-OMe) 2-cPr 0 0
3376 Cl H CO (3-Thi-4-OMe) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3377 Cl H CO (3-Thi-4-OMe) 2,6-Me ₂ 0 0
3378 Cl H CO (3-Thi-4-OMe) 2-Me, 6-cPr 0 0
3379 Cl H CO (5-Pyza-1-CH ₂ Ph-3-tBu) 2-Me 0 0
3380 Cl H CO (5-Pyza-1-CH ₂ Ph-3-tBu) 2-iPr 0 0
3381 Cl H CO (5-Pyza-1-CH ₂ Ph-3-tBu) 2-cPr 0 0
3382 Cl H CO (5-Pyza-1-CH ₂ Ph-3-tBu) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3383 Cl H CO (5-Pyza-1-CH ₂ Ph-3-tBu) 2,6-Me ₂ 0 0
3384 Cl H CO (5-Pyza-1-CH ₂ Ph-3-tBu) 2-Me, 6-cPr 0 0
3385 Cl H CO (4-Pyza-1,3-Me ₂ -5-Cl) 2-Me 0 0
3386 Cl H CO (4-Pyza-1,3-Me ₂ -5-Cl) 2-iPr 0 0
3387 Cl H CO (4-Pyza-1,3-Me ₂ -5-Cl) 2-cPr 0 0
3388 Cl H CO (4-Pyza-1,3-Me ₂ -5-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3389 Cl H CO (4-Pyza-1,3-Me ₂ -5-Cl) 2,6-Me ₂ 0 0
3390 Cl H CO (4-Pyza-1,3-Me ₂ -5-Cl) 2-Me, 6-cPr 0 0
3391 Cl H CO {4-Ioxa-5-Me-3- (Ph-2-Cl)} 2-Me 0 0
3392 Cl H CO {4-Ioxa-5-Me-3- (Ph-2-Cl)} 2-iPr 0 0
3393 Cl H CO {4-Ioxa-5-Me-3- (Ph-2-Cl)} 2-cPr 0 0
3394 Cl H CO {4-Ioxa-5-Me-3- (Ph-2-Cl)} 2-CH ₂ CH ₂ CH ₂ -3 0 0
3395 Cl H CO {4-Ioxa-5-Me-3- (Ph-2-Cl)} 2,6-Me ₂ 0 0
3396 Cl H CO {4-Ioxa-5-Me-3- (Ph-2-Cl)} 2-Me, 6-cPr 0 0
3397 Cl H CO (5-Tdia-4-Me) 2-Me 0 0
3398 Cl H CO (5-Tdia-4-Me) 2-iPr 0 0
3399 Cl H CO (5-Tdia-4-Me) 2-cPr 0 0
3400 Cl H CO (5-Tdia-4-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3401 Cl H CO (5-Tdia-4-Me) 2,6-Me ₂ 0 0
3402 Cl H CO (5-Tdia-4-Me) 2-Me, 6-cPr 0 0
3403 Cl H CO (2-Pyr-6-Me) 2-Me 0 0
3404 Cl H CO (2-Pyr-6-Me) 2-iPr 0 0
3405 Cl H CO (2-Pyr-6-Me) 2-cPr 0 0
3406 Cl H CO (2-Pyr-6-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3407 Cl H CO (2-Pyr-6-Me) 2,6-Me ₂ 0 0
3408 Cl H CO (2-Pyr-6-Me) 2-Me, 6-cPr 0 0
3409 Cl H CO (2-Pyr-5-Bu) 2-Me 0 0
3410 Cl H CO (2-Pyr-5-Bu) 2-iPr 0 0
3411 Cl H CO (2-Pyr-5-Bu) 2-cPr 0 0
3412 Cl H CO (2-Pyr-5-Bu) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3413 Cl H CO (2-Pyr-5-Bu) 2,6-Me ₂ 0 0
3414 Cl H CO (2-Pyr-5-Bu) 2-Me, 6-cPr 0 0
3415 Cl H CO (3-Pyr) 2-Me 0 0
3416 Cl H CO (3-Pyr) 2-iPr 0 0
3417 Cl H CO (3-Pyr) 2-cPr 0 0
3418 Cl H CO (3-Pyr) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3419 Cl H CO (3-Pyr) 2,6-Me ₂ 0 0
3420 Cl H CO (3-Pyr) 2-Me, 6-cPr 0 0
3421 Cl H CO (3-Pyr-2-Cl) 2-Me 0 0
3422 Cl H CO (3-Pyr-2-Cl) 2-iPr 0 0
3423 Cl H CO (3-Pyr-2-Cl) 2-cPr 0 0
3424 Cl H CO (3-Pyr-2-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3425 Cl H CO (3-Pyr-2-Cl) 2,6-Me ₂ 0 0
3426 Cl H CO (3-Pyr-2-Cl) 2-Me, 6-cPr 0 0
3427 Cl H CO (3-Pyr-2-Me) 2-Me 0 0
3428 Cl H CO (3-Pyr-2-Me) 2-iPr 0 0
3429 Cl H CO (3-Pyr-2-Me) 2-cPr 0 0
3430 Cl H CO (3-Pyr-2-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3431 Cl H CO (3-Pyr-2-Me) 2,6-Me ₂ 0 0
3432 Cl H CO (3-Pyr-2-Me) 2-Me, 6-cPr 0 0
3433 Cl H CO (3-Pyr-2-OPh) 2-Me 0 0
3434 Cl H CO (3-Pyr-2-OPh) 2-iPr 0 0
3435 Cl H CO (3-Pyr-2-OPh) 2-cPr 0 0
3436 Cl H CO (3-Pyr-2-OPh) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3437 Cl H CO (3-Pyr-2-OPh) 2,6-Me ₂ 0 0
3438 Cl H CO (3-Pyr-2-OPh) 2-Me, 6-cPr 0 0
3439 Cl H CO (3-Pyr-2-SMe) 2-Me 0 0
3440 Cl H CO (3-Pyr-2-SMe) 2-iPr 0 0
3441 Cl H CO (3-Pyr-2-SMe) 2-cPr 0 0
3442 Cl H CO (3-Pyr-2-SMe) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3443 Cl H CO (3-Pyr-2-SMe) 2,6-Me ₂ 0 0
3444 Cl H CO (3-Pyr-2-SMe) 2-Me, 6-cPr 0 0
3445 Cl H CO (3-Pyr-2-SCH ₂ CH = CH ₂ ) 2-Me 0 0
3446 Cl H CO (3-Pyr-2-SCH ₂ CH = CH ₂ ) 2-iPr 0 0
3447 Cl H CO (3-Pyr-2-SCH ₂ CH = CH ₂ ) 2-cPr 0 0
3448 Cl H CO (3-Pyr-2-SCH ₂ CH = CH ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3449 Cl H CO (3-Pyr-2-SCH ₂ CH = CH ₂ ) 2,6-Me ₂ 0 0
3450 Cl H CO (3-Pyr-2-SCH ₂ CH = CH ₂ ) 2-Me, 6-cPr 0 0
3451 Cl H CO (3-Pyr-2-SPh) 2-Me 0 0
3452 Cl H CO (3-Pyr-2-SPh) 2-iPr 0 0
3453 Cl H CO (3-Pyr-2-SPh) 2-cPr 0 0
3454 Cl H CO (3-Pyr-2-SPh) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3455 Cl H CO (3-Pyr-2-SPh) 2,6-Me ₂ 0 0
3456 Cl H CO (3-Pyr-2-SPh) 2-Me, 6-cPr 0 0
3457 Cl H CO (3-Pyr-4-CF _Three ) 2-Me 0 0
3458 Cl H CO (3-Pyr-4-CF _Three ) 2-iPr 0 0
3459 Cl H CO (3-Pyr-4-CF _Three ) 2-cPr 0 0
3460 Cl H CO (3-Pyr-4-CF _Three ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3461 Cl H CO (3-Pyr-4-CF _Three ) 2,6-Me ₂ 0 0
3462 Cl H CO (3-Pyr-4-CF _Three ) 2-Me, 6-cPr 0 0
3463 Cl H CO (3-Pyr-6-Cl) 2-Me 0 0
3464 Cl H CO (3-Pyr-6-Cl) 2-iPr 0 0
3465 Cl H CO (3-Pyr-6-Cl) 2-cPr 0 0
3466 Cl H CO (3-Pyr-6-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3467 Cl H CO (3-Pyr-6-Cl) 2,6-Me ₂ 0 0
3468 Cl H CO (3-Pyr-6-Cl) 2-Me, 6-cPr 0 0
3469 Cl H CO (3-Pyr-2,6-Cl ₂ ) 2-Me 0 0
3470 Cl H CO (3-Pyr-2,6-Cl ₂ ) 2-iPr 0 0
3471 Cl H CO (3-Pyr-2,6-Cl ₂ ) 2-cPr 0 0
3472 Cl H CO (3-Pyr-2,6-Cl ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3473 Cl H CO (3-Pyr-2,6-Cl ₂ ) 2,6-Me ₂ 0 0
3474 Cl H CO (3-Pyr-2,6-Cl ₂ ) 2-Me, 6-cPr 0 0
3475 Cl H CO (3-Pyr-2-Cl-6-Me) 2-Me 0 0
3476 Cl H CO (3-Pyr-2-Cl-6-Me) 2-iPr 0 0
3477 Cl H CO (3-Pyr-2-Cl-6-Me) 2-cPr 0 0
3478 Cl H CO (3-Pyr-2-Cl-6-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3479 Cl H CO (3-Pyr-2-Cl-6-Me) 2,6-Me ₂ 0 0
3480 Cl H CO (3-Pyr-2-Cl-6-Me) 2-Me, 6-cPr 0 0
3481 Cl H CO (3-Pyr-5,6-Cl ₂ ) 2-Me 0 0
3482 Cl H CO (3-Pyr-5,6-Cl ₂ ) 2-iPr 0 0
3483 Cl H CO (3-Pyr-5,6-Cl ₂ ) 2-cPr 0 0
3484 Cl H CO (3-Pyr-5,6-Cl ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3485 Cl H CO (3-Pyr-5,6-Cl ₂ ) 2,6-Me ₂ 0 0
3486 Cl H CO (3-Pyr-5,6-Cl ₂ ) 2-Me, 6-cPr 0 0
3487 Cl H CO (4-Pyr-2-Cl) 2-Me 0 0
3488 Cl H CO (4-Pyr-2-Cl) 2-iPr 0 0
3489 Cl H CO (4-Pyr-2-Cl) 2-cPr 0 0
3490 Cl H CO (4-Pyr-2-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3491 Cl H CO (4-Pyr-2-Cl) 2,6-Me ₂ 0 0
3492 Cl H CO (4-Pyr-2-Cl) 2-Me, 6-cPr 0 0
3493 Cl H CO (2-Bfur) 2-Me 0 0
3494 Cl H CO (2-Bfur) 2-iPr 0 0
3495 Cl H CO (2-Bfur) 2-cPr 0 0
3496 Cl H CO (2-Bfur) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3497 Cl H CO (2-Bfur) 2,6-Me ₂ 0 0
3498 Cl H CO (2-Bfur) 2-Me, 6-cPr 0 0
3499 Cl H CO (2-Bthi) 2-Me 0 0
3500 Cl H CO (2-Bthi) 2-iPr 0 0
3501 Cl H CO (2-Bthi) 2-cPr 0 0
3502 Cl H CO (2-Bthi) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3503 Cl H CO (2-Bthi) 2,6-Me ₂ 0 0
3504 Cl H CO (2-Bthi) 2-Me, 6-cPr 0 0
3505 Cl H CO (6-Bthia) 2-Me 0 0
3506 Cl H CO (6-Bthia) 2-iPr 0 0
3507 Cl H CO (6-Bthia) 2-cPr 0 0
3508 Cl H CO (6-Bthia) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3509 Cl H CO (6-Bthia) 2,6-Me ₂ 0 0
3510 Cl H CO (6-Bthia) 2-Me, 6-cPr 0 0
3511 Cl H CO (5-Boxaz) 2-Me 0 0
3512 Cl H CO (5-Boxaz) 2-iPr 0 0
3513 Cl H CO (5-Boxaz) 2-cPr 0 0
3514 Cl H CO (5-Boxaz) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3515 Cl H CO (5-Boxaz) 2,6-Me ₂ 0 0
3516 Cl H CO (5-Boxaz) 2-Me, 6-cPr 0 0
3517 Cl H CO (1-Iqu) 2-Me 0 0
3518 Cl H CO (1-Iqu) 2-iPr 0 0
3519 Cl H CO (1-Iqu) 2-cPr 0 0
3520 Cl H CO (1-Iqu) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3521 Cl H CO (1-Iqu) 2,6-Me ₂ 0 0
3522 Cl H CO (1-Iqu) 2-Me, 6-cPr 0 0
3523 Cl H CONMe (tBu) 2-Me 0 0
3524 Cl H CONMe (tBu) 2-iPr 0 0
3525 Cl H CONMe (tBu) 2-cPr 0 0
3526 Cl H CONMe (tBu) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3527 Cl H CONMe (tBu) 2,6-Me ₂ 0 0
3528 Cl H CONMe (tBu) 2-Me, 6-cPr 0 0
3529 Cl H CONBu ₂ 2-Me 0 0
3530 Cl H CONBu ₂ 2-iPr 0 0
3531 Cl H CONBu ₂ 2-cPr 0 0
3532 Cl H CONBu ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
3533 Cl H CONBu ₂ 2,6-Me ₂ 0 0
3534 Cl H CONBu ₂ 2-Me, 6-cPr 0 0
3535 Cl H CONMe (CH ₂ Ph) 2-Me 0 0
3536 Cl H CONMe (CH ₂ Ph) 2-iPr 0 0
3537 Cl H CONMe (CH ₂ Ph) 2-cPr 0 0
3538 Cl H CONMe (CH ₂ Ph) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3539 Cl H CONMe (CH ₂ Ph) 2,6-Me ₂ 0 0
3540 Cl H CONMe (CH ₂ Ph) 2-Me, 6-cPr 0 0
3541 Cl H CONMe (CH ₂ CN) 2-Me 0 0
3542 Cl H CONMe (CH ₂ CN) 2-iPr 0 0
3543 Cl H CONMe (CH ₂ CN) 2-cPr 0 0
3544 Cl H CONMe (CH ₂ CN) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3545 Cl H CONMe (CH ₂ CN) 2,6-Me ₂ 0 0
3546 Cl H CONMe (CH ₂ CN) 2-Me, 6-cPr 0 0
3547 Cl H CONMe (CH ₂ CO ₂ Et) 2-Me 0 0
3548 Cl H CONMe (CH ₂ CO ₂ Et) 2-iPr 0 0
3549 Cl H CONMe (CH ₂ CO ₂ Et) 2-cPr 0 0
3550 Cl H CONMe (CH ₂ CO ₂ Et) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3551 Cl H CONMe (CH ₂ CO ₂ Et) 2,6-Me ₂ 0 0
3552 Cl H CONMe (CH ₂ CO ₂ Et) 2-Me, 6-cPr 0 0
3553 Cl H CONMe (2-Pyr) 2-Me 0 0
3554 Cl H CONMe (2-Pyr) 2-iPr 0 0
3555 Cl H CONMe (2-Pyr) 2-cPr 0 0
3556 Cl H CONMe (2-Pyr) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3557 Cl H CONMe (2-Pyr) 2,6-Me ₂ 0 0
3558 Cl H CONMe (2-Pyr) 2-Me, 6-cPr 0 0
3559 Cl H CONMe (OMe) 2-Me 0 0
3560 Cl H CONMe (OMe) 2-iPr 0 0
3561 Cl H CONMe (OMe) 2-cPr 0 0
3562 Cl H CONMe (OMe) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3563 Cl H CONMe (OMe) 2,6-Me ₂ 0 0
3564 Cl H CONMe (OMe) 2-Me, 6-cPr 0 0
3565 Cl H CON (CH ₂ CH ₂ Cl) ₂ 2-Me 0 0
3566 Cl H CON (CH ₂ CH ₂ Cl) ₂ 2-iPr 0 0
3567 Cl H CON (CH ₂ CH ₂ Cl) ₂ 2-cPr 0 0
3568 Cl H CON (CH ₂ CH ₂ Cl) ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
3569 Cl H CON (CH ₂ CH ₂ Cl) ₂ 2,6-Me ₂ 0 0
3570 Cl H CON (CH ₂ CH ₂ Cl) ₂ 2-Me, 6-cPr 0 0
3571 Cl H CON (CH ₂ CH = CH ₂ ) ₂ 2-Me 0 0
3572 Cl H CON (CH ₂ CH = CH ₂ ) ₂ 2-iPr 0 0
3573 Cl H CON (CH ₂ CH = CH ₂ ) ₂ 2-cPr 0 0
3574 Cl H CON (CH ₂ CH = CH ₂ ) ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
3575 Cl H CON (CH ₂ CH = CH ₂ ) ₂ 2,6-Me ₂ 0 0
3576 Cl H CON (CH ₂ CH = CH ₂ ) ₂ 2-Me, 6-cPr 0 0
3577 Cl H CON (CH ₂ CN) ₂ 2-Me 0 0
3578 Cl H CON (CH ₂ CN) ₂ 2-iPr 0 0
3579 Cl H CON (CH ₂ CN) ₂ 2-cPr 0 0
3580 Cl H CON (CH ₂ CN) ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
3581 Cl H CON (CH ₂ CN) ₂ 2,6-Me ₂ 0 0
3582 Cl H CON (CH ₂ CN) ₂ 2-Me, 6-cPr 0 0
3583 Cl H CON (CH ₂ CH ₂ CN) ₂ 2-Me 0 0
3584 Cl H CON (CH ₂ CH ₂ CN) ₂ 2-iPr 0 0
3585 Cl H CON (CH ₂ CH ₂ CN) ₂ 2-cPr 0 0
3586 Cl H CON (CH ₂ CH ₂ CN) ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
3587 Cl H CON (CH ₂ CH ₂ CN) ₂ 2,6-Me ₂ 0 0
3588 Cl H CON (CH ₂ CH ₂ CN) ₂ 2-Me, 6-cPr 0 0
3589 Cl H CON (CH ₂ CO ₂ Et) ₂ 2-Me 0 0
3590 Cl H CON (CH ₂ CO ₂ Et) ₂ 2-iPr 0 0
3591 Cl H CON (CH ₂ CO ₂ Et) ₂ 2-cPr 0 0
3592 Cl H CON (CH ₂ CO ₂ Et) ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
3593 Cl H CON (CH ₂ CO ₂ Et) ₂ 2,6-Me ₂ 0 0
3594 Cl H CON (CH ₂ CO ₂ Et) ₂ 2-Me, 6-cPr 0 0
3595 Cl H CON (CH ₂ CH ₂ OMe) ₂ 2-Me 0 0
3596 Cl H CON (CH ₂ CH ₂ OMe) ₂ 2-iPr 0 0
3597 Cl H CON (CH ₂ CH ₂ OMe) ₂ 2-cPr 0 0
3598 Cl H CON (CH ₂ CH ₂ OMe) ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
3599 Cl H CON (CH ₂ CH ₂ OMe) ₂ 2,6-Me ₂ 0 0
3600 Cl H CON (CH ₂ CH ₂ OMe) ₂ 2-Me, 6-cPr 0 0
3601 Cl H CON (CH ₂ CH ₂ OEt) ₂ 2-Me 0 0
3602 Cl H CON (CH ₂ CH ₂ OEt) ₂ 2-iPr 0 0
3603 Cl H CON (CH ₂ CH ₂ OEt) ₂ 2-cPr 0 0
3604 Cl H CON (CH ₂ CH ₂ OEt) ₂ 2-CH ₂ CH ₂ CH ₂ -3 0 0
3605 Cl H CON (CH ₂ CH ₂ OEt) ₂ 2,6-Me ₂ 0 0
3606 Cl H CON (CH ₂ CH ₂ OEt) ₂ 2-Me, 6-cPr 0 0
3607 Cl H CO (1-Azet) 2-Me 0 0
3608 Cl H CO (1-Azet) 2-iPr 0 0
3609 Cl H CO (1-Azet) 2-cPr 0 0
3610 Cl H CO (1-Azet) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3611 Cl H CO (1-Azet) 2,6-Me ₂ 0 0
3612 Cl H CO (1-Azet) 2-Me, 6-cPr 0 0
3613 Cl H CO (1-Pyrd-2-CO ₂ Me) 2-Me 0 0
3614 Cl H CO (1-Pyrd-2-CO ₂ Me) 2-iPr 0 0
3615 Cl H CO (1-Pyrd-2-CO ₂ Me) 2-cPr 0 0
3616 Cl H CO (1-Pyrd-2-CO ₂ Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3617 Cl H CO (1-Pyrd-2-CO ₂ Me) 2,6-Me ₂ 0 0
3618 Cl H CO (1-Pyrd-2-CO ₂ Me) 2-Me, 6-cPr 0 0
3619 Cl H CO (1-Pyrd-3-OH) 2-Me 0 0
3620 Cl H CO (1-Pyrd-3-OH) 2-iPr 0 0
3621 Cl H CO (1-Pyrd-3-OH) 2-cPr 0 0
3622 Cl H CO (1-Pyrd-3-OH) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3623 Cl H CO (1-Pyrd-3-OH) 2,6-Me ₂ 0 0
3624 Cl H CO (1-Pyrd-3-OH) 2-Me, 6-cPr 0 0
3625 Cl H CO (1-Pyrr-2,5-Me ₂ ) 2-Me 0 0
3626 Cl H CO (1-Pyrr-2,5-Me ₂ ) 2-iPr 0 0
3627 Cl H CO (1-Pyrr-2,5-Me ₂ ) 2-cPr 0 0
3628 Cl H CO (1-Pyrr-2,5-Me ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3629 Cl H CO (1-Pyrr-2,5-Me ₂ ) 2,6-Me ₂ 0 0
3630 Cl H CO (1-Pyrr-2,5-Me ₂ ) 2-Me, 6-cPr 0 0
3631 Cl H CO (1-Ppri) 2-Me 0 0
3632 Cl H CO (1-Ppri) 2-iPr 0 0
3633 Cl H CO (1-Ppri) 2-cPr 0 0
3634 Cl H CO (1-Ppri) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3635 Cl H CO (1-Ppri) 2,6-Me ₂ 0 0
3636 Cl H CO (1-Ppri) 2-Me, 6-cPr 0 0
3637 Cl H CO (1-Ppri-2-CO ₂ Me) 2-Me 0 0
3638 Cl H CO (1-Ppri-2-CO ₂ Me) 2-iPr 0 0
3639 Cl H CO (1-Ppri-2-CO ₂ Me) 2-cPr 0 0
3640 Cl H CO (1-Ppri-2-CO ₂ Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3641 Cl H CO (1-Ppri-2-CO ₂ Me) 2,6-Me ₂ 0 0
3642 Cl H CO (1-Ppri-2-CO ₂ Me) 2-Me, 6-cPr 0 0
3643 Cl H CO (1-Ppri-4-Br) 2-Me 0 0
3644 Cl H CO (1-Ppri-4-Br) 2-iPr 0 0
3645 Cl H CO (1-Ppri-4-Br) 2-cPr 0 0
3646 Cl H CO (1-Ppri-4-Br) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3647 Cl H CO (1-Ppri-4-Br) 2,6-Me ₂ 0 0
3648 Cl H CO (1-Ppri-4-Br) 2-Me, 6-cPr 0 0
3649 Cl H CO (1-Ppri-4-Me) 2-Me 0 0
3650 Cl H CO (1-Ppri-4-Me) 2-iPr 0 0
3651 Cl H CO (1-Ppri-4-Me) 2-cPr 0 0
3652 Cl H CO (1-Ppri-4-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3653 Cl H CO (1-Ppri-4-Me) 2,6-Me ₂ 0 0
3654 Cl H CO (1-Ppri-4-Me) 2-Me, 6-cPr 0 0
3655 Cl H CO (1-Ppri-4-CO ₂ Me) 2-Me 0 0
3656 Cl H CO (1-Ppri-4-CO ₂ Me) 2-iPr 0 0
3657 Cl H CO (1-Ppri-4-CO ₂ Me) 2-cPr 0 0
3658 Cl H CO (1-Ppri-4-CO ₂ Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3659 Cl H CO (1-Ppri-4-CO ₂ Me) 2,6-Me ₂ 0 0
3660 Cl H CO (1-Ppri-4-CO ₂ Et) 2-Me, 6-cPr 0 0
3661 Cl H CO (1-Ppri-4-OCH ₂ CH ₂ O-4) 2-Me 0 0
3662 Cl H CO (1-Ppri-4-OCH ₂ CH ₂ O-4) 2-iPr 0 0
3663 Cl H CO (1-Ppri-4-OCH ₂ CH ₂ O-4) 2-cPr 0 0
3664 Cl H CO (1-Ppri-4-OCH ₂ CH ₂ O-4) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3665 Cl H CO (1-Ppri-4-OCH ₂ CH ₂ O-4) 2,6-Me ₂ 0 0
3666 Cl H CO (1-Ppri-4-OCH ₂ CH ₂ O-4) 2-Me, 6-cPr 0 0
3667 Cl H CO (1-Ppri-2,2,6,6-Me _Four ) 2-Me 0 0
3668 Cl H CO (1-Ppri-2,2,6,6-Me _Four ) 2-iPr 0 0
3669 Cl H CO (1-Ppri-2,2,6,6-Me _Four ) 2-cPr 0 0
3670 Cl H CO (1-Ppri-2,2,6,6-Me _Four ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3671 Cl H CO (1-Ppri-2,2,6,6-Me _Four ) 2,6-Me ₂ 0 0
3672 Cl H CO (1-Ppri-2,2,6,6-Me _Four ) 2-Me, 6-cPr 0 0
3673 Cl H CO (1-Ppra-4-Me) 2-Me 0 0
3674 Cl H CO (1-Ppra-4-Me) 2-iPr 0 0
3675 Cl H CO (1-Ppra-4-Me) 2-cPr 0 0
3676 Cl H CO (1-Ppra-4-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3677 Cl H CO (1-Ppra-4-Me) 2,6-Me ₂ 0 0
3678 Cl H CO (1-Ppra-4-Me) 2-Me, 6-cPr 0 0
3679 Cl H CO (1-Ppra-4-Ph) 2-Me 0 0
3680 Cl H CO (1-Ppra-4-Ph) 2-iPr 0 0
3681 Cl H CO (1-Ppra-4-Ph) 2-cPr 0 0
3682 Cl H CO (1-Ppra-4-Ph) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3683 Cl H CO (1-Ppra-4-Ph) 2,6-Me ₂ 0 0
3684 Cl H CO (1-Ppra-4-Ph) 2-Me, 6-cPr 0 0
3685 Cl H CO-4-Morp 2-Me 0 0
3686 Cl H CO-4-Morp 2-iPr 0 0
3687 Cl H CO-4-Morp 2-cPr 0 0
3688 Cl H CO-4-Morp 2-CH ₂ CH ₂ CH ₂ -3 0 0
3689 Cl H CO-4-Morp 2,6-Me ₂ 0 0
3690 Cl H CO-4-Morp 2-Me, 6-cPr 0 0
3691 Cl H CO (4-Morp-2,6-Me ₂ ) 2-Me 0 0
3692 Cl H CO (4-Morp-2,6-Me ₂ ) 2-iPr 0 0
3693 Cl H CO (4-Morp-2,6-Me ₂ ) 2-cPr 0 0
3694 Cl H CO (4-Morp-2,6-Me ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3695 Cl H CO (4-Morp-2,6-Me ₂ ) 2,6-Me ₂ 0 0
3696 Cl H CO (4-Morp-2,6-Me ₂ ) 2-Me, 6-cPr 0 0
3697 Cl H CO-4-Tmor 2-Me 0 0
3698 Cl H CO-4-Tmor 2-iPr 0 0
3699 Cl H CO-4-Tmor 2-cPr 0 0
3700 Cl H CO-4-Tmor 2-CH ₂ CH ₂ CH ₂ -3 0 0
3701 Cl H CO-4-Tmor 2,6-Me ₂ 0 0
3702 Cl H CO-4-Tmor 2-Me, 6-cPr 0 0
3703 Cl H COQ ¹⁸ 2-Me 0 0
3704 Cl H COQ ¹⁸ 2-iPr 0 0
3705 Cl H COQ ¹⁸ 2-cPr 0 0
3706 Cl H COQ ¹⁸ 2-CH ₂ CH ₂ CH ₂ -3 0 0
3707 Cl H COQ ¹⁸ 2,6-Me ₂ 0 0
3708 Cl H COQ ¹⁸ 2-Me, 6-cPr 0 0
3709 Cl H CO (9-Carb) 2-Me 0 0
3710 Cl H CO (9-Carb) 2-iPr 0 0
3711 Cl H CO (9-Carb) 2-cPr 0 0
3712 Cl H CO (9-Carb) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3713 Cl H CO (9-Carb) 2,6-Me ₂ 0 0
3714 Cl H CO (9-Carb) 2-Me, 6-cPr 0 0
3715 Cl H CO (10-Pthia) 2-Me 0 0
3716 Cl H CO (10-Pthia) 2-iPr 0 0
3717 Cl H CO (10-Pthia) 2-cPr 0 0
3718 Cl H CO (10-Pthia) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3719 Cl H CO (10-Pthia) 2,6-Me ₂ 0 0
3720 Cl H CO (10-Pthia) 2-Me, 6-cPr 0 0
3721 Cl H SO ₂ (Ph-2-CO ₂ Q ^Five ) 2-Me, 6-cPr 0 0
3722 Cl H SO ₂ (Ph-3-CO ₂ Q ^Five ) 2-Me, 6-cPr 0 0
3723 Cl H SO ₂ (Ph-4-CO ₂ Q ^Five ) 2-Me, 6-cPr 0 0
3724 Cl H SO ₂ (Ph-4-OMe) 2-Cl 0 0
3725 Cl H SO ₂ (Ph-4-OMe) 2-Br 0 0
3726 Cl H SO ₂ (Ph-4-OMe) 2-I 0 0
3727 Cl H SO ₂ (Ph-4-OMe) 2-cBu 0 0
3728 Cl H SO ₂ (Ph-4-OMe) 2-cPr, 5-Me 0 0
3729 Cl H SO ₂ (Ph-4-OMe) 2-OMe, 5-Me 0 0
3730 Cl H SO ₂ (Ph-4-OMe) 2-F, 6-iPr 0 0
3731 Cl H SO ₂ (Ph-4-OMe) 2-Cl, 6-cPr 0 0
3732 Cl H SO ₂ (Ph-4-OMe) 2-Br, 6-Me 0 0
3733 Cl H SO ₂ (Ph-4-OMe) 2-I, 6-Me 0 0
3734 Cl H SO ₂ (Ph-4-OMe) 2-Me, 6-Et 0 0
3735 Cl H SO ₂ (Ph-4-OMe) 2,6-cPr ₂ 0 0
3736 Cl H SO ₂ (Ph-4-OMe) 2-cPr, 3,5-Me ₂ 0 0
3737 Cl H SO ₂ (Ph-4-OMe) 2-cPr, 3,6-Me ₂ 0 0
3738 Cl H SO ₂ (Ph-2-SO ₂ OQ ⁶ ) 2-Me 0 0
3739 Cl H SO ₂ (Ph-2-SO ₂ OQ ⁷ ) 2-iPr 0 0
3740 Cl H SO ₂ (Ph-2-SO ₂ OQ ⁸ ) 2-cPr 0 0
3741 Cl H SO ₂ (Ph-2-SO ₂ OQ ⁹ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3742 Cl H SO ₂ (Ph-2-SO ₂ OQ ^Ten ) 2,6-Me ₂ 0 0
3743 Cl H SO ₂ (Ph-2-SO ₂ OQ ¹¹ ) 2-Me, 6-cPr 0 0
3744 Cl H SO ₂ (Ph-2-SO ₂ OQ ¹² ) 2-Me, 6-cPr 0 0
3745 Cl H SO ₂ (Ph-2-SO ₂ OQ ¹³ ) 2-Me, 6-cPr 0 0
3746 Cl H SO ₂ (Ph-2-SO ₂ OQ ¹⁴ ) 2-Me, 6-cPr 0 0
3747 Cl H SO ₂ (Ph-2-SO ₂ OQ ¹⁵ ) 2-Me, 6-cPr 0 0
3748 Cl H SO ₂ (Ph-2-SO ₂ OQ ¹⁶ ) 2-Me, 6-cPr 0 0
3749 Cl H SO ₂ (Ph-2-SO ₂ OQ ¹⁷ ) 2-Me, 6-cPr 0 0
3750 Cl H SO ₂ (Ph-3-SO ₂ OQ ⁶ ) 2-Me 0 0
3751 Cl H SO ₂ (Ph-3-SO ₂ OQ ⁷ ) 2-iPr 0 0
3752 Cl H SO ₂ (Ph-3-SO ₂ OQ ⁸ ) 2-cPr 0 0
3753 Cl H SO ₂ (Ph-3-SO ₂ OQ ⁹ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3754 Cl H SO ₂ (Ph-3-SO ₂ OQ ^Ten ) 2,6-Me ₂ 0 0
3755 Cl H SO ₂ (Ph-3-SO ₂ OQ ¹¹ ) 2-Me, 6-cPr 0 0
3756 Cl H SO ₂ (Ph-3-SO ₂ OQ ¹² ) 2-Me, 6-cPr 0 0
3757 Cl H SO ₂ (Ph-3-SO ₂ OQ ¹³ ) 2-Me, 6-cPr 0 0
3758 Cl H SO ₂ (Ph-3-SO ₂ OQ ¹⁴ ) 2-Me, 6-cPr 0 0
3759 Cl H SO ₂ (Ph-3-SO ₂ OQ ¹⁵ ) 2-Me, 6-cPr 0 0
3760 Cl H SO ₂ (Ph-3-SO ₂ OQ ¹⁶ ) 2-Me, 6-cPr 0 0
3761 Cl H SO ₂ (Ph-3-SO ₂ OQ ¹⁷ ) 2-Me, 6-cPr 0 0
3762 Cl H SO ₂ (Ph-4-SO ₂ OQ ^Five ) 2-Cl, 6-cPr 0 0
3763 Cl H SO ₂ (Ph-4-SO ₂ OQ ⁶ ) 2-Me 0 0
3764 Cl H SO ₂ (Ph-4-SO ₂ OQ ⁷ ) 2-iPr 0 0
3765 Cl H SO ₂ (Ph-4-SO ₂ OQ ⁸ ) 2-cPr 0 0
3766 Cl H SO ₂ (Ph-4-SO ₂ OQ ⁹ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3767 Cl H SO ₂ (Ph-4-SO ₂ OQ ^Ten ) 2,6-Me ₂ 0 0
3768 Cl H SO ₂ (Ph-4-SO ₂ OQ ¹¹ ) 2-Me, 6-cPr 0 0
3769 Cl H SO ₂ (Ph-4-SO ₂ OQ ¹² ) 2-Me, 6-cPr 0 0
3770 Cl H SO ₂ (Ph-4-SO ₂ OQ ¹³ ) 2-Me, 6-cPr 0 0
3771 Cl H SO ₂ (Ph-4-SO ₂ OQ ¹⁴ ) 2-Me, 6-cPr 0 0
3772 Cl H SO ₂ (Ph-4-SO ₂ OQ ¹⁵ ) 2-Me, 6-cPr 0 0
3773 Cl H SO ₂ (Ph-4-SO ₂ OQ ¹⁶ ) 2-Me, 6-cPr 0 0
3774 Cl H SO ₂ (Ph-4-SO ₂ OQ ¹⁷ ) 2-Me, 6-cPr 0 0
3775 Cl H SO ₂ (Ph-2,5-Cl ₂ ) 2-Me 0 0
3776 Cl H SO ₂ (Ph-2,5-Cl ₂ ) 2-iPr 0 0
3777 Cl H SO ₂ (Ph-2,5-Cl ₂ ) 2-cPr 0 0
3778 Cl H SO ₂ (Ph-2,5-Cl ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3779 Cl H SO ₂ (Ph-2,5-Cl ₂ ) 2,6-Me ₂ 0 0
3780 Cl H SO ₂ (Ph-2,5-Cl ₂ ) 2-Me, 6-cPr 0 0
3781 Cl H SO ₂ (Ph-3-NO ₂ -4-Cl) 2-Me 0 0
3782 Cl H SO ₂ (Ph-3-NO ₂ -4-Cl) 2-iPr 0 0
3783 Cl H SO ₂ (Ph-3-NO ₂ -4-Cl) 2-cPr 0 0
3784 Cl H SO ₂ (Ph-3-NO ₂ -4-Cl) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3785 Cl H SO ₂ (Ph-3-NO ₂ -4-Cl) 2,6-Me ₂ 0 0
3786 Cl H SO ₂ (Ph-3-NO ₂ -4-Cl) 2-Me, 6-cPr 0 0
3787 Cl H SO ₂ (2-Thi) 2-Me 0 0
3788 Cl H SO ₂ (2-Thi) 2-iPr 0 0
3789 Cl H SO ₂ (2-Thi) 2-cPr 0 0
3790 Cl H SO ₂ (2-Thi) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3791 Cl H SO ₂ (2-Thi) 2,6-Me ₂ 0 0
3792 Cl H SO ₂ (2-Thi) 2-Me, 6-cPr 0 0
3793 Cl HN (Bu) _Four 2-Me 0 0
3794 Cl HN (Bu) _Four 2-iPr 0 0
3795 Cl HN (Bu) _Four 2-cPr 0 0
3796 Cl HN (Bu) _Four 2-CH ₂ CH ₂ CH ₂ -3 0 0
3797 Cl HN (Bu) _Four 2,6-Me ₂ 0 0
3798 Cl HN (Bu) _Four 2-Me, 6-cPr 0 0
3799 Cl H Li 2-Me, 6-cPr 0 0
3800 Cl H Na 2-Me 0 0
3801 Cl H Na 2-iPr 0 0
3802 Cl H Na 2-cPr 0 0
3803 Cl H Na 2-CH ₂ CH ₂ CH ₂ -3 0 0
3804 Cl H Na 2,6-Me ₂ 0 0
3805 Cl H Na 2-Me, 6-cPr 0 0
3806 Cl HK 2-Me 0 0
3807 Cl HK 2-iPr 0 0
3808 Cl HK 2-cPr 0 0
3809 Cl HK 2-CH ₂ CH ₂ CH ₂ -3 0 0
3810 Cl HK 2,6-Me ₂ 0 0
3811 Cl HK 2-Me, 6-cPr 0 0
3812 Cl H Rb 2-Me, 6-cPr 0 0
3813 Cl H Cs 2-Me, 6-cPr 0 0
3814 Cl H Mg 2-Me, 6-cPr 0 0
3815 Cl H Ca 2-Me, 6-cPr 0 0
3816 Cl H Ba 2-Me, 6-cPr 0 0
3817 Cl H Sc 2-Me, 6-cPr 0 0
3818 Cl H Ti 2-Me, 6-cPr 0 0
3819 Cl H Mn 2-Me, 6-cPr 0 0
3820 Cl H Fe 2-Me, 6-cPr 0 0
3821 Cl H Cu 2-Me, 6-cPr 0 0
3822 Cl H Ag 2-Me, 6-cPr 0 0
3823 Cl H Au 2-Me, 6-cPr 0 0
3824 Cl H Zn 2-Me, 6-cPr 0 0
3825 Cl H Al 2-Me, 6-cPr 0 0
3826 Cl FH 2-Me 0 0
3827 Cl FH 2-iPr 0 0
3828 Cl FH 2-cPr 0 0
3829 Cl FH 2-CH ₂ CH ₂ CH ₂ -3 0 0
3830 Cl FH 2,6-Me ₂ 0 0
3831 Cl FH 2-Me, 6-cPr 0 0
3832 Cl Cl H 2-Me 0 0
3833 Cl Cl H 2-iPr 0 0
3834 Cl Cl H 2-cPr 0 0
3835 Cl Cl H 2-CH ₂ CH ₂ CH ₂ -3 0 0
3836 Cl Cl H 2,6-Me ₂ 0 0
3837 Cl Cl H 2-Me, 6-cPr 0 0
3838 Cl Br H 2-Me 0 0
3839 Cl Br H 2-iPr 0 0
3840 Cl Br H 2-cPr 0 0
3841 Cl Br H 2-CH ₂ CH ₂ CH ₂ -3 0 0
3842 Cl Br H 2,6-Me ₂ 0 0
3843 Cl Br H 2-Me, 6-cPr 0 0
3844 Cl IH 2-Me 0 0
3845 Cl IH 2-iPr 0 0
3846 Cl IH 2-cPr 0 0
3847 Cl IH 2-CH ₂ CH ₂ CH ₂ -3 0 0
3848 Cl IH 2,6-Me ₂ 0 0
3849 Cl IH 2-Me, 6-cPr 0 0
3850 Cl H OCOPh 2-Me, 4-OCOPh 0 0
3851 Cl H CO-4-Thpy 2-Me 0 0
3852 Cl H CO-4-Thpy 2-iPr 0 0
3853 Cl H CO-4-Thpy 2-cPr 0 0
3854 Cl H CO-4-Thpy 2-CH ₂ CH ₂ CH ₂ -3 0 0
3855 Cl H CO-4-Thpy 2,6-Me ₂ 0 0
3856 Cl H CO-4-Thpy 2-Me, 6-cPr 0 0
3857 Cl H CONMe ₂ 2-F 0 0
3858 Cl H CONMe ₂ 2-Et 0 0
3859 Cl H CONMe ₂ 2-tBu 0 0
3860 Cl H CONMe ₂ 2-sBu 0 0
3861 Cl H CONMe ₂ 2- (cPr-1-Me) 0 0
3862 Cl H CONMe ₂ 2- (cPr-2,2-Cl ₂ ) 0 0
3863 Cl H CONMe ₂ 2-cBu 0 0
3864 Cl H CONMe ₂ 2-cHx 0 0
3865 Cl H CONMe ₂ 2-Ph 0 0
3866 Cl H CONMe ₂ 2-iPr, 5-Me 0 0
3867 Cl H CONMe ₂ 2-CH = CHCH = CH-3 0 0
3868 Cl H CONMe ₂ 2-CH = CHO-3 0 0
3869 Cl H CONMe ₂ 2-CH ₂ CH ₂ O-3 0 0
3870 Cl H CONMe ₂ 2-OCH = CH-3 0 0
3871 Cl H CONMe ₂ 2-OCH ₂ CH ₂ -3 0 0
3872 Cl H CONMe ₂ 2-cPr, 5-F 0 0
3873 Cl H CONMe ₂ 2-cPr, 5-Cl 0 0
3874 Cl H CONMe ₂ 2-F, 6-cPr 0 0
3875 Cl H CONMe ₂ 2-Cl, 6-Me 0 0
3876 Cl H CONMe ₂ 2-Br, 6-Et 0 0
3877 Cl H CONMe ₂ 2-Br, 6-cPr 0 0
3878 Cl H CONMe ₂ 2-I, 6-Et 0 0
3879 Cl H CONMe ₂ 2-Et, 6-cPr 0 0
3880 Cl H CONMe ₂ 2-iPr, 6-cPr 0 0
3881 Cl H CONMe ₂ 2-tBu, 6-cPr 0 0
3882 Cl H CONMe ₂ 2-cPr, 6-OMe 0 0
3883 Cl H CONMe ₂ 2-Br, 3,6-Me ₂ 0 0
3884 Cl H CONMe ₂ 2-cPr, 4,6-Me ₂ 0 0
3885 Cl H CONMe ₂ 2-Br, 5,6-Me ₂ 0 0
3886 Cl H CONMe ₂ 2-Br, 5-CH = CH-O-6 0 0
3887 Cl H CONMe ₂ 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
3888 Cl H CONMe ₂ 2-Me, 5-CH ₂ CH ₂ O-6 0 0
3889 Cl H CONMe ₂ 2-Me, 5-CH = CH-O-6 0 0
3890 Cl H CONMe ₂ 2-Et, 5-CH ₂ CH ₂ CH ₂ -6 0 0
3891 Cl H CONMe ₂ 2-cPr, 5-CH ₂ CH ₂ CH ₂ -6 0 0
3892 Cl H CONMe ₂ 2-cPr, 5-CH = CH-O-6 0 0
3893 Cl H CONMe ₂ 2-Br, 3,5,6-Me _Three 0 0
3894 Cl H CONMe ₂ 2,3,5,6-Me _Four 0 0
3895 Cl H CO (1-Azr) 2-Me 0 0
3896 Cl H CO (1-Azr) 2-iPr 0 0
3897 Cl H CO (1-Azr) 2-cPr 0 0
3898 Cl H CO (1-Azr) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3899 Cl H CO (1-Azr) 2,6-Me ₂ 0 0
3900 Cl H CO (1-Azr) 2-Me, 6-cPr 0 0
3901 Cl H CO (1-Azr-2-Me) 2-Me 0 0
3902 Cl H CO (1-Azr-2-Me) 2-iPr 0 0
3903 Cl H CO (1-Azr-2-Me) 2-cPr 0 0
3904 Cl H CO (1-Azr-2-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3905 Cl H CO (1-Azr-2-Me) 2,6-Me ₂ 0 0
3906 Cl H CO (1-Azr-2-Me) 2-Me, 6-cPr 0 0
3907 Cl H CO (1-Azr-2-CO ₂ Me) 2-Me 0 0
3908 Cl H CO (1-Azr-2-CO ₂ Me) 2-iPr 0 0
3909 Cl H CO (1-Azr-2-CO ₂ Me) 2-cPr 0 0
3910 Cl H CO (1-Azr-2-CO ₂ Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3911 Cl H CO (1-Azr-2-CO ₂ Me) 2,6-Me ₂ 0 0
3912 Cl H CO (1-Azr-2-CO ₂ Me) 2-Me, 6-cPr 0 0
3913 Cl H CONMe (OEt) 2-Me 0 0
3914 Cl H CONMe (OEt) 2-iPr 0 0
3915 Cl H CONMe (OEt) 2-cPr 0 0
3916 Cl H CONMe (OEt) 2-CH ₂ CH ₂ CH ₂ -3 0 0
3917 Cl H CONMe (OEt) 2,6-Me ₂ 0 0
3918 Cl H CONMe (OEt) 2-Me, 6-cPr 0 0
3919 Cl H CO-4-Morp 2-F 0 0
3920 Cl H CO-4-Morp 2-Cl 0 0
3921 Cl H CO-4-Morp 2-Br 0 0
3922 Cl H CO-4-Morp 2-I 0 0
3923 Cl H CO-4-Morp 2-Et 0 0
3924 Cl H CO-4-Morp 2-tBu 0 0
3925 Cl H CO-4-Morp 2-sBu 0 0
3926 Cl H CO-4-Morp 2- (cPr-1-Me) 0 0
3927 Cl H CO-4-Morp 2- (cPr-2,2-Cl ₂ ) 0 0
3928 Cl H CO-4-Morp 2-cBu 0 0
3929 Cl H CO-4-Morp 2-cHx 0 0
3930 Cl H CO-4-Morp 2-Ph 0 0
3931 Cl H CO-4-Morp 2-iPr, 5-Me 0 0
3932 Cl H CO-4-Morp 2-CH = CHCH = CH-3 0 0
3933 Cl H CO-4-Morp 2-CH = CHO-3 0 0
3934 Cl H CO-4-Morp 2-CH ₂ CH ₂ O-3 0 0
3935 Cl H CO-4-Morp 2-OCH = CH-3 0 0
3936 Cl H CO-4-Morp 2-OCH ₂ CH ₂ -3 0 0
3937 Cl H CO-4-Morp 2-cPr, 5-F 0 0
3938 Cl H CO-4-Morp 2-cPr, 5-Cl 0 0
3939 Cl H CO-4-Morp 2,5-Me ₂ 0 0
3940 Cl H CO-4-Morp 2-cPr, 5-Me 0 0
3941 Cl H CO-4-Morp 2-OMe, 5-Me 0 0
3942 Cl H CO-4-Morp 2-F, 6-iPr 0 0
3943 Cl H CO-4-Morp 2-F, 6-cPr 0 0
3944 Cl H CO-4-Morp 2-Cl, 6-Me 0 0
3945 Cl H CO-4-Morp 2-Cl, 6-cPr 0 0
3946 Cl H CO-4-Morp 2-Br, 6-Me 0 0
3947 Cl H CO-4-Morp 2-Br, 6-Et 0 0
3948 Cl H CO-4-Morp 2-Br, 6-cPr 0 0
3949 Cl H CO-4-Morp 2-I, 6-Me 0 0
3950 Cl H CO-4-Morp 2-I, 6-Et 0 0
3951 Cl H CO-4-Morp 2-Me, 6-Et 0 0
3952 Cl H CO-4-Morp 2-Et, 6-cPr 0 0
3953 Cl H CO-4-Morp 2-iPr, 6-cPr 0 0
3954 Cl H CO-4-Morp 2-tBu, 6-cPr 0 0
3955 Cl H CO-4-Morp 2,6-cPr ₂ 0 0
3956 Cl H CO-4-Morp 2-cPr, 6-OMe 0 0
3957 Cl H CO-4-Morp 2-Br, 3,6-Me ₂ 0 0
3958 Cl H CO-4-Morp 2-cPr, 3,5-Me ₂ 0 0
3959 Cl H CO-4-Morp 2-cPr, 4,6-Me ₂ 0 0
3960 Cl H CO-4-Morp 2-Br, 5,6-Me ₂ 0 0
3961 Cl H CO-4-Morp 2-cPr, 5,6-Me ₂ 0 0
3962 Cl H CO-4-Morp 2-Br, 5-CH = CH-O-6 0 0
3963 Cl H CO-4-Morp 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
3964 Cl H CO-4-Morp 2-Me, 5-CH ₂ CH ₂ O-6 0 0
3965 Cl H CO-4-Morp 2-Me, 5-CH = CH-O-6 0 0
3966 Cl H CO-4-Morp 2-Et, 5-CH ₂ CH ₂ CH ₂ -6 0 0
3967 Cl H CO-4-Morp 2-cPr, 5-CH ₂ CH ₂ CH ₂ -6 0 0
3968 Cl H CO-4-Morp 2-cPr, 5-CH = CH-O-6 0 0
3969 Cl H CO-4-Morp 2-Br, 3,5,6-Me _Three 0 0
3970 Cl H CO-4-Morp 2,3,5,6-Me _Four 0 0
3971 Cl H COQ ¹⁹ 2-F 0 0
3972 Cl H COQ ¹⁹ 2-Cl 0 0
3973 Cl H COQ ¹⁹ 2-Br 0 0
3974 Cl H COQ ¹⁹ 2-I 0 0
3975 Cl H COQ ¹⁹ 2-Me 0 0
3976 Cl H COQ ¹⁹ 2-Et 0 0
3977 Cl H COQ ¹⁹ 2-iPr 0 0
3978 Cl H COQ ¹⁹ 2-tBu 0 0
3979 Cl H COQ ¹⁹ 2-sBu 0 0
3980 Cl H COQ ¹⁹ 2- (cPr-1-Me) 0 0
3981 Cl H COQ ¹⁹ 2-cPr 0 0
3982 Cl H COQ ¹⁹ 2- (cPr-2,2-Cl ₂ ) 0 0
3983 Cl H COQ ¹⁹ 2-cBu 0 0
3984 Cl H COQ ¹⁹ 2-cHx 0 0
3985 Cl H COQ ¹⁹ 2-Ph 0 0
3986 Cl H COQ ¹⁹ 3-tBu 0 0
3987 Cl H COQ ¹⁹ 3-OMe 0 0
3988 Cl H COQ ¹⁹ 2-iPr, 5-Me 0 0
3989 Cl H COQ ¹⁹ 2-CH ₂ CH ₂ CH ₂ -3 0 0
3990 Cl H COQ ¹⁹ 2-CH = CHCH = CH-3 0 0
3991 Cl H COQ ¹⁹ 2-CH = CHO-3 0 0
3992 Cl H COQ ¹⁹ 2-CH ₂ CH ₂ O-3 0 0
3993 Cl H COQ ¹⁹ 2-OCH = CH-3 0 0
3994 Cl H COQ ¹⁹ 2-OCH ₂ CH ₂ -3 0 0
3995 Cl H COQ ¹⁹ 2-cPr, 5-F 0 0
3996 Cl H COQ ¹⁹ 2-cPr, 5-Cl 0 0
3997 Cl H COQ ¹⁹ 2-cPr, 5-Me 0 0
3998 Cl H COQ ¹⁹ 2-OMe, 5-Me 0 0
3999 Cl H COQ ¹⁹ 2-F, 6-iPr 0 0
4000 Cl H COQ ¹⁹ 2-F, 6-cPr 0 0
4001 Cl H COQ ¹⁹ 2-Cl, 6-Me 0 0
4002 Cl H COQ ¹⁹ 2-Cl, 6-cPr 0 0
4003 Cl H COQ ¹⁹ 2-Br, 6-Me 0 0
4004 Cl H COQ ¹⁹ 2-Br, 6-Et 0 0
4005 Cl H COQ ¹⁹ 2-Br, 6-cPr 0 0
4006 Cl H COQ ¹⁹ 2-I, 6-Me 0 0
4007 Cl H COQ ¹⁹ 2-I, 6-Et 0 0
4008 Cl H COQ ¹⁹ 2,6-Me ₂ 0 0
4009 Cl H COQ ¹⁹ 2-Me, 6-Et 0 0
4010 Cl H COQ ¹⁹ 2-Me, 6-cPr 0 0
4011 Cl H COQ ¹⁹ 2-Et, 6-cPr 0 0
4012 Cl H COQ ¹⁹ 2-iPr, 6-cPr 0 0
4013 Cl H COQ ¹⁹ 2-tBu, 6-cPr 0 0
4014 Cl H COQ ¹⁹ 2,6-cPr ₂ 0 0
4015 Cl H COQ ¹⁹ 2-cPr, 6-OMe 0 0
4016 Cl H COQ ¹⁹ 2-Br, 3,6-Me ₂ 0 0
4017 Cl H COQ ¹⁹ 2-cPr, 3,5-Me ₂ 0 0
4018 Cl H COQ ¹⁹ 2-cPr, 4,6-Me ₂ 0 0
4019 Cl H COQ ¹⁹ 2-Br, 5,6-Me ₂ 0 0
4020 Cl H COQ ¹⁹ 2-cPr, 5,6-Me ₂ 0 0
4021 Cl H COQ ¹⁹ 2-Br, 5-CH = CH-O-6 0 0
4022 Cl H COQ ¹⁹ 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4023 Cl H COQ ¹⁹ 2-Me, 5-CH ₂ CH ₂ O-6 0 0
4024 Cl H COQ ¹⁹ 2-Me, 5-CH = CH-O-6 0 0
4025 Cl H COQ ¹⁹ 2-Et, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4026 Cl H COQ ¹⁹ 2-cPr, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4027 Cl H COQ ¹⁹ 2-cPr, 5-CH = CH-O-6 0 0
4028 Cl H COQ ¹⁹ 2-Br, 3,5,6-Me _Three 0 0
4029 Cl H COQ ¹⁹ 2,3,5,6-Me _Four 0 0
4030 Cl H CO (Ph-4-Me) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4031 Cl H CO (Ph-4-Me) 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4032 Cl H CO ₂ (3-Ppri) 2-Me 0 0
4033 Cl H CO ₂ (3-Ppri) 2-iPr 0 0
4034 Cl H CO ₂ (3-Ppri) 2-cPr 0 0
4035 Cl H CO ₂ (3-Ppri) 2-CH ₂ CH ₂ CH ₂ -3 0 0
4036 Cl H CO ₂ (3-Ppri) 2,6-Me ₂ 0 0
4037 Cl H CO ₂ (3-Ppri) 2-Me, 6-cPr 0 0
4038 Cl H CO ₂ (3-Ppri) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4039 Cl H CO ₂ (3-Ppri) 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4040 Cl H CON (CH ₂ CN) ₂ 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4041 Cl H CON (CH ₂ CN) ₂ 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4042 Cl H CO (1-Ppri-3-OH) 2-Me 0 0
4043 Cl H CO (1-Ppri-3-OH) 2-iPr 0 0
4044 Cl H CO (1-Ppri-3-OH) 2-cPr 0 0
4045 Cl H CO (1-Ppri-3-OH) 2-CH ₂ CH ₂ CH ₂ -3 0 0
4046 Cl H CO (1-Ppri-3-OH) 2,6-Me ₂ 0 0
4047 Cl H CO (1-Ppri-3-OH) 2-Me, 6-cPr 0 0
4048 Cl H CO (1-Ppri-3-OH) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4049 Cl H CO (1-Ppri-3-OH) 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4050 Cl H CO (1-Ppri-4-OH) 2-Me 0 0
4051 Cl H CO (1-Ppri-4-OH) 2-iPr 0 0
4052 Cl H CO (1-Ppri-4-OH) 2-cPr 0 0
4053 Cl H CO (1-Ppri-4-OH) 2-CH ₂ CH ₂ CH ₂ -3 0 0
4054 Cl H CO (1-Ppri-4-OH) 2,6-Me ₂ 0 0
4055 Cl H CO (1-Ppri-4-OH) 2-Me, 6-cPr 0 0
4056 Cl H CO (1-Ppri-4-OH) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4057 Cl H CO (1-Ppri-4-OH) 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4058 Cl H CO [1-Ppri-4- (1-Pyrd)] 2-Me 0 0
4059 Cl H CO [1-Ppri-4- (1-Pyrd)] 2-iPr 0 0
4060 Cl H CO [1-Ppri-4- (1-Pyrd)] 2-cPr 0 0
4061 Cl H CO [1-Ppri-4- (1-Pyrd)] 2-CH ₂ CH ₂ CH ₂ -3 0 0
4062 Cl H CO [1-Ppri-4- (1-Pyrd)] 2,6-Me ₂ 0 0
4063 Cl H CO [1-Ppri-4- (1-Pyrd)] 2-Me, 6-cPr 0 0
4064 Cl H CO [1-Ppri-4- (1-Pyrd)] 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4065 Cl H CO [1-Ppri-4- (1-Pyrd)] 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4066 Cl H CO [1-Ppri-4-(= NOMe)] 2-Me 0 0
4067 Cl H CO [1-Ppri-4-(= NOMe)] 2-iPr 0 0
4068 Cl H CO [1-Ppri-4-(= NOMe)] 2-cPr 0 0
4069 Cl H CO [1-Ppri-4-(= NOMe)] 2-CH ₂ CH ₂ CH ₂ -3 0 0
4070 Cl H CO [1-Ppri-4-(= NOMe)] 2,6-Me ₂ 0 0
4071 Cl H CO [1-Ppri-4-(= NOMe)] 2-Me, 6-cPr 0 0
4072 Cl H CO [1-Ppri-4-(= NOMe)] 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4073 Cl H CO [1-Ppri-4-(= NOMe)] 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4074 Cl H CO [1-Ppri-4-(= O)] 2-Me 0 0
4075 Cl H CO [1-Ppri-4-(= O)] 2-iPr 0 0
4076 Cl H CO [1-Ppri-4-(= O)] 2-cPr 0 0
4077 Cl H CO [1-Ppri-4-(= O)] 2-CH ₂ CH ₂ CH ₂ -3 0 0
4078 Cl H CO [1-Ppri-4-(= O)] 2,6-Me ₂ 0 0
4079 Cl H CO [1-Ppri-4-(= O)] 2-Me, 6-cPr 0 0
4080 Cl H CO [1-Ppri-4-(= O)] 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4081 Cl H CO [1-Ppri-4-(= O)] 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4082 Cl H CO (1-Ppra-4-COMe) 2-Me 0 0
4083 Cl H CO (1-Ppra-4-COMe) 2-iPr 0 0
4084 Cl H CO (1-Ppra-4-COMe) 2-cPr 0 0
4085 Cl H CO (1-Ppra-4-COMe) 2-CH ₂ CH ₂ CH ₂ -3 0 0
4086 Cl H CO (1-Ppra-4-COMe) 2,6-Me ₂ 0 0
4087 Cl H CO (1-Ppra-4-COMe) 2-Me, 6-cPr 0 0
4088 Cl H CO (1-Ppra-4-COMe) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4089 Cl H CO (1-Ppra-4-COMe) 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4090 Cl H CO [1-Ppra-4-CO (4-Morp)] 2-Me 0 0
4091 Cl H CO [1-Ppra-4-CO (4-Morp)] 2-iPr 0 0
4092 Cl H CO [1-Ppra-4-CO (4-Morp)] 2-cPr 0 0
4093 Cl H CO [1-Ppra-4-CO (4-Morp)] 2-CH ₂ CH ₂ CH ₂ -3 0 0
4094 Cl H CO [1-Ppra-4-CO (4-Morp)] 2,6-Me ₂ 0 0
4095 Cl H CO [1-Ppra-4-CO (4-Morp)] 2-Me, 6-cPr 0 0
4096 Cl H CO [1-Ppra-4-CO (4-Morp)] 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4097 Cl H CO [1-Ppra-4-CO (4-Morp)] 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4098 Cl H CO (1-Ppra-4-CO ₂ Et) 2-Me 0 0
4099 Cl H CO (1-Ppra-4-CO ₂ Et) 2-iPr 0 0
4100 Cl H CO (1-Ppra-4-CO ₂ Et) 2-cPr 0 0
4101 Cl H CO (1-Ppra-4-CO ₂ Et) 2-CH ₂ CH ₂ CH ₂ -3 0 0
4102 Cl H CO (1-Ppra-4-CO ₂ Et) 2,6-Me ₂ 0 0
4103 Cl H CO (1-Ppra-4-CO ₂ Et) 2-Me, 6-cPr 0 0
4104 Cl H CO (1-Ppra-4-CO ₂ Et) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4105 Cl H CO (1-Ppra-4-CO ₂ Et) 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4106 Cl H CO (1-Ppra-4-CN) 2-Me 0 0
4107 Cl H CO (1-Ppra-4-CN) 2-iPr 0 0
4108 Cl H CO (1-Ppra-4-CN) 2-cPr 0 0
4109 Cl H CO (1-Ppra-4-CN) 2-CH ₂ CH ₂ CH ₂ -3 0 0
4110 Cl H CO (1-Ppra-4-CN) 2,6-Me ₂ 0 0
4111 Cl H CO (1-Ppra-4-CN) 2-Me, 6-cPr 0 0
4112 Cl H CO (1-Ppra-4-CN) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4113 Cl H CO (1-Ppra-4-CN) 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4114 Cl H CO (1-Ppra-4-CO ₂ Q ^Five ) 2-Me 0 0
4115 Cl H CO (1-Ppra-4-CO ₂ Q ^Five ) 2-iPr 0 0
4116 Cl H CO (1-Ppra-4-CO ₂ Q ^Five ) 2-cPr 0 0
4117 Cl H CO (1-Ppra-4-CO ₂ Q ^Five ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
4118 Cl H CO (1-Ppra-4-CO ₂ Q ^Five ) 2,6-Me ₂ 0 0
4119 Cl H CO (1-Ppra-4-CO ₂ Q ^Five ) 2-Me, 6-cPr 0 0
4120 Cl H CO (1-Ppra-4-CO ₂ Q ^Five ) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4121 Cl H CO (1-Ppra-4-CO ₂ Q ^Five ) 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4122 Cl H CO (1-Ppra-4-CO ₂ Q ¹¹ ) 2-Me 0 0
4123 Cl H CO (1-Ppra-4-CO ₂ Q ¹¹ ) 2-iPr 0 0
4124 Cl H CO (1-Ppra-4-CO ₂ Q ¹¹ ) 2-cPr 0 0
4125 Cl H CO (1-Ppra-4-CO ₂ Q ¹¹ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
4126 Cl H CO (1-Ppra-4-CO ₂ Q ¹¹ ) 2,6-Me ₂ 0 0
4127 Cl H CO (1-Ppra-4-CO ₂ Q ¹¹ ) 2-Me, 6-cPr 0 0
4128 Cl H CO (1-Ppra-4-CO ₂ Q ¹¹ ) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4129 Cl H CO (1-Ppra-4-CO ₂ Q ¹¹ ) 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4130 Cl H CO-4-Morp 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4131 Cl Cl CO-4-Morp 2-Me 0 0
4132 Cl Cl CO-4-Morp 2-iPr 0 0
4133 Cl Cl CO-4-Morp 2-cPr 0 0
4134 Cl Cl CO-4-Morp 2-CH ₂ CH ₂ CH ₂ -3 0 0
4135 Cl Cl CO-4-Morp 2,6-Me ₂ 0 0
4136 Cl Cl CO-4-Morp 2-Me, 6-cPr 0 0
4137 Cl Cl CO-4-Morp 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4138 Cl Cl CO-4-Morp 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4139 Cl Br CO-4-Morp 2-Me, 6-cPr 0 0
4140 Cl I CO-4-Morp 2-Me, 6-cPr 0 0
4141 Cl H CO (4-Morp-2-Me) 2-Me 0 0
4142 Cl H CO (4-Morp-2-Me) 2-iPr 0 0
4143 Cl H CO (4-Morp-2-Me) 2-cPr 0 0
4144 Cl H CO (4-Morp-2-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
4145 Cl H CO (4-Morp-2-Me) 2,6-Me ₂ 0 0
4146 Cl H CO (4-Morp-2-Me) 2-Me, 6-cPr 0 0
4147 Cl H CO (4-Morp-2-Me) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4148 Cl H CO (4-Morp-2-Me) 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4149 Cl H CO (4-Morp-3-Me) 2-Me 0 0
4150 Cl H CO (4-Morp-3-Me) 2-iPr 0 0
4151 Cl H CO (4-Morp-3-Me) 2-cPr 0 0
4152 Cl H CO (4-Morp-3-Me) 2-CH ₂ CH ₂ CH ₂ -3 0 0
4153 Cl H CO (4-Morp-3-Me) 2,6-Me ₂ 0 0
4154 Cl H CO (4-Morp-3-Me) 2-Me, 6-cPr 0 0
4155 Cl H CO (4-Morp-3-Me) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4156 Cl H CO (4-Morp-3-Me) 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4157 Cl H CO (Q ¹⁹ -2,2-Me ₂ ) 2-Me 0 0
4158 Cl H CO (Q ¹⁹ -2,2-Me ₂ ) 2-iPr 0 0
4159 Cl H CO (Q ¹⁹ -2,2-Me ₂ ) 2-cPr 0 0
4160 Cl H CO (Q ¹⁹ -2,2-Me ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
4161 Cl H CO (Q ¹⁹ -2,2-Me ₂ ) 2,6-Me ₂ 0 0
4162 Cl H CO (Q ¹⁹ -2,2-Me ₂ ) 2-Me, 6-cPr 0 0
4163 Cl H CO (Q ¹⁹ -2,2-Me ₂ ) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4164 Cl H CO (Q ¹⁹ -2,2-Me ₂ ) 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4165 Cl H CO [(Q ¹⁹ -2-(= O)] 2-Me 0 0
4166 Cl H CO [(Q ¹⁹ -2-(= O)] 2-iPr 0 0
4167 Cl H CO [(Q ¹⁹ -2-(= O)] 2-cPr 0 0
4168 Cl H CO [(Q ¹⁹ -2-(= O)] 2-CH ₂ CH ₂ CH ₂ -3 0 0
4169 Cl H CO [(Q ¹⁹ -2-(= O)] 2,6-Me ₂ 0 0
4170 Cl H CO [(Q ¹⁹ -2-(= O)] 2-Me, 6-cPr 0 0
4171 Cl H CO [(Q ¹⁹ -2-(= O)] 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4172 Cl H CO [(Q ¹⁹ -2-(= O)] 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4173 Cl H CO (Q ¹⁹ -4,4-Me ₂ ) 2-Me 0 0
4174 Cl H CO (Q ¹⁹ -4,4-Me ₂ ) 2-iPr 0 0
4175 Cl H CO (Q ¹⁹ -4,4-Me ₂ ) 2-cPr 0 0
4176 Cl H CO (Q ¹⁹ -4,4-Me ₂ ) 2-CH ₂ CH ₂ CH ₂ -3 0 0
4177 Cl H CO (Q ¹⁹ -4,4-Me ₂ ) 2,6-Me ₂ 0 0
4178 Cl H CO (Q ¹⁹ -4,4-Me ₂ ) 2-Me, 6-cPr 0 0
4179 Cl H CO (Q ¹⁹ -4,4-Me ₂ ) 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4180 Cl H CO (Q ¹⁹ -4,4-Me ₂ ) 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4181 Cl H COQ ²⁰ 2-Me 0 0
4182 Cl H COQ ²⁰ 2-iPr 0 0
4183 Cl H COQ ²⁰ 2-cPr 0 0
4184 Cl H COQ ²⁰ 2-CH ₂ CH ₂ CH ₂ -3 0 0
4185 Cl H COQ ²⁰ 2,6-Me ₂ 0 0
4186 Cl H COQ ²⁰ 2-Me, 6-cPr 0 0
4187 Cl H COQ ²⁰ 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4188 Cl H COQ ²⁰ 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4189 Cl H COQ ^{twenty one} 2-Me 0 0
4190 Cl H COQ ^{twenty one} 2-iPr 0 0
4191 Cl H COQ ^{twenty one} 2-cPr 0 0
4192 Cl H COQ ^{twenty one} 2-CH ₂ CH ₂ CH ₂ -3 0 0
4193 Cl H COQ ^{twenty one} 2,6-Me ₂ 0 0
4194 Cl H COQ ^{twenty one} 2-Me, 6-cPr 0 0
4195 Cl H COQ ^{twenty one} 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4196 Cl H COQ ^{twenty one} 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4197 Cl H COQ ^{twenty two} 2-Me 0 0
4198 Cl H COQ ^{twenty two} 2-iPr 0 0
4199 Cl H COQ ^{twenty two} 2-cPr 0 0
4200 Cl H COQ ^{twenty two} 2-CH ₂ CH ₂ CH ₂ -3 0 0
4201 Cl H COQ ^{twenty two} 2,6-Me ₂ 0 0
4202 Cl H COQ ^{twenty two} 2-Me, 6-cPr 0 0
4203 Cl H COQ ^{twenty two} 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4204 Cl H COQ ^{twenty two} 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4205 Cl H COQ ^{twenty three} 2-Me 0 0
4206 Cl H COQ ^{twenty three} 2-iPr 0 0
4207 Cl H COQ ^{twenty three} 2-cPr 0 0
4208 Cl H COQ ^{twenty three} 2-CH ₂ CH ₂ CH ₂ -3 0 0
4209 Cl H COQ ^{twenty three} 2,6-Me ₂ 0 0
4210 Cl H COQ ^{twenty three} 2-Me, 6-cPr 0 0
4211 Cl H COQ ^{twenty three} 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4212 Cl H COQ ^{twenty three} 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4213 Cl H COQ ^{twenty four} 2-Me 0 0
4214 Cl H COQ ^{twenty four} 2-iPr 0 0
4215 Cl H COQ ^{twenty four} 2-cPr 0 0
4216 Cl H COQ ^{twenty four} 2-CH ₂ CH ₂ CH ₂ -3 0 0
4217 Cl H COQ ^{twenty four} 2,6-Me ₂ 0 0
4218 Cl H COQ ^{twenty four} 2-Me, 6-cPr 0 0
4219 Cl H COQ ^{twenty four} 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4220 Cl H COQ ^{twenty four} 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4221 Cl H COQ ^{twenty five} 2-Me 0 0
4222 Cl H COQ ^{twenty five} 2-iPr 0 0
4223 Cl H COQ ^{twenty five} 2-cPr 0 0
4224 Cl H COQ ^{twenty five} 2-CH ₂ CH ₂ CH ₂ -3 0 0
4225 Cl H COQ ^{twenty five} 2,6-Me ₂ 0 0
4226 Cl H COQ ^{twenty five} 2-Me, 6-cPr 0 0
4227 Cl H COQ ^{twenty five} 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4228 Cl H COQ ^{twenty five} 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4229 Cl H COQ ²⁶ 2-Me 0 0
4230 Cl H COQ ²⁶ 2-iPr 0 0
4231 Cl H COQ ²⁶ 2-cPr 0 0
4232 Cl H COQ ²⁶ 2-CH ₂ CH ₂ CH ₂ -3 0 0
4233 Cl H COQ ²⁶ 2,6-Me ₂ 0 0
4234 Cl H COQ ²⁶ 2-Me, 6-cPr 0 0
4235 Cl H COQ ²⁶ 2-Me, 5-CH ₂ CH ₂ CH ₂ -6 0 0
4236 Cl H COQ ²⁶ 2-Br, 5-CH ₂ CH ₂ CH ₂ -6 0 0
――――――――――――――――――――――――――――――――――――

Among the above exemplified compounds, suitable compounds are compound numbers 124, 125, 126, 127, 128, 130, 131, 132, 134, 136, 139, 140, 144, 145, 151, 163, 173, 202, 207. , 217, 226, 249, 264, 265, 266, 267, 269, 270, 271, 272, 273, 279, 280, 284, 287, 292, 300, 304, 305, 306, 307, 308, 309, 311 , 330, 334, 336, 339, 344, 359, 361, 362, 364, 365, 370, 377, 385, 386, 387, 390, 391, 400, 401, 403, 410, 412, 413, 417, 422 , 426,437,438,441,443,446,450,456,459,472,478,498,505,506,507,514,515,516,521,527,528,529,531,532,534 , 535,539,541,544,547,557,562,566,571,614,618,621,623,629,640,642,658,659,662,663,664,667,700,701,702 , 704, 707, 708, 710, 711, 712, 716, 717, 719, 728, 732, 733, 734, 735, 736, 737, 738, 740, 756, 758, 759, 760, 761, 762, 775 , 778,780,781,782,801,802,803,804,805,806,827,8 34, 835, 844, 845, 846, 850, 890, 894, 896, 911, 914, 931, 964, 965, 979, 982, 987, 998, 1000, 1007, 1009, 1013, 1016, 1020, 1023, 1027, 1040, 1050, 1052, 1053, 1055, 1058, 1060, 1061, 1063, 1064, 1066, 1069, 1073, 1083, 1086, 1088, 1089, 1091, 1096, 1099, 1100, 1102, 1109, 1115, 1118, 1119, 1120, 1122, 1123, 1124, 1125, 1126, 1128, 1129, 1133, 1140, 1151, 1160, 1172, 1178, 1184, 1207, 1251, 1260, 1266, 1286, 1298, 1334, 1340, 1358, 1364, 1382, 1387, 1391, 1417, 1441, 1446, 1448, 1456, 1459, 1461, 1481, 1509, 1522, 1531, 1537, 1543, 1549, 1553, 1554, 1566, 1575, 1593, 1599, 1603, 1616, 1620, 1625, 1631, 1643, 1649, 1658, 1706, 1710, 1757, 1770, 1789, 1811, 1840, 1877, 1879, 1891, 1898, 1911, 1920, 1924, 1937, 1946, 1952, 1958, 1981, 1985, 1889, 2010, 2034, 2038, 2040, 2042, 2051, 2060, 2066, 2072, 2081, 2106, 2136, 2147, 2151, 2176, 2198, 2199 , 2200, 2212, 2220, 2221, 2222, 2224, 2225, 2263, 2265, 2287, 2289, 2300, 2309, 2315, 2321, 2327, 2333, 2411, 2431, 2453, 2519, 2529, 2540, 2542, 2547 , 2548, 2551, 2555, 2556, 2565, 2568, 2570, 2571, 2572, 2574, 2576, 2577, 2585, 2587, 2589, 2592, 2596, 2597, 2599, 2600, 2601, 2603, 2605, 2606, 2607 , 2608, 2609, 2614, 2662, 2671, 2677, 2697, 2703, 2709, 2715, 2721, 2727, 2733, 2739, 2746, 2752, 2758, 2764, 2770, 2776, 2782, 2788, 2805, 2814, 2820 , 2826, 2827, 2838, 2850, 2856, 2862, 2868, 2874, 2880, 2900, 2906, 2918, 2924, 2930, 2961, 2970, 2976, 2982, 2988, 2994, 3001, 3016, 3022, 3028, 3034 , 3040, 3046, 3052, 3058, 3064, 3070, 3076, 3082, 3088, 3094, 3100, 3106, 3112, 3129, 3138, 3144, 3150, 3156, 3162, 3168, 3185, 3194, 3200, 3217, 3226 , 3243, 3252, 3258, 3264, 3270, 3276, 3282, 3288, 3294, 3300, 3306, 3312, 3318, 3324, 3330, 3336, 3342, 334 8, 3354, 3360, 3366, 3372, 3378, 3384, 3390, 3396, 3402, 3408, 3414, 3420, 3426, 3432, 3438, 3444, 3450, 3456, 3462, 3468, 3474, 3480, 3486, 3492, 3498, 3504, 3510, 3516, 3522, 3528, 3534, 3540, 3546, 3552, 3558, 3564, 3570, 3576, 3582, 3588, 3594, 3600, 3606, 3612, 3618, 3624, 3630, 3636, 3642, 3648, 3654, 3660, 3666, 3672, 3678, 3684, 3687, 3686, 3687, 3688, 3689, 3690, 3696, 3702, 3708, 3714, 3720, 3755, 3780, 3786, 3792, 3798, 3805, 3811, 3837, 3843, 3849, 3887, 3894, 3918, 3920, 3939, 3941, 3944, 3946, 3951, 3963, 3970, 4010, 4022, 4030, 4037, 4038, 4040, 4047, 4048, 4055, 4056, 4063, 4064, 4071, 4072, 4079, 4080, 4087, 4088, 4095, 4096, 4103, 4104, 4111, 4119, 4127, 4130, 4136, 4146, 4154, 4155, 4162, 4163, 4170, 4178, 4179, 4186, No. 4187, 4194, 4195, 4202, 4210, 4211, 4218, 4219, 4226, 4227, 4234 or 4235,
More preferably, compound numbers 124, 125, 126, 127, 128, 130, 132, 136, 139, 140, 144, 145, 151, 163, 173, 202, 217, 249, 264, 265, 266, 267 , 269,270,271,284,287,300,304,308,309,311,334,336,339,361,362,377,385,386,387,390,391,401,437,438,459 , 472, 505, 506, 507, 515, 516, 521, 528, 529, 531, 532, 534, 539, 541, 544, 547, 571, 621, 658, 659, 662, 663, 664, 667, 700 , 701, 702, 704, 707, 708, 711, 712, 717, 719, 732, 733, 734, 735, 736, 737, 738, 740, 756, 758, 759, 760, 762, 775, 778, 780 781, 782, 801, 802, 803, 806, 827, 834, 835, 845, 846, 850, 896, 914, 931, 964, 965, 998, 1013, 1016, 1023, 1040, 1050, 1052, 1053 , 1055, 1058, 1060, 1061, 1063, 1064, 1066, 1069, 1073, 1086, 1088, 1089, 1091, 1096, 1099, 1100, 1102, 1109, 1115, 1118, 1119, 1120, 1123, 1124, 1125 , 1126, 1129, 1133, 1140, 1151, 1160, 1172, 1 178, 1184, 1207, 1260, 1266, 1286, 1298, 1334, 1340, 1358, 1364, 1382, 1387, 1391, 1417, 1441, 1446, 1448, 1481, 1522, 1531, 1537, 1543, 1549, 1566, 1575, 1593, 1599, 1616, 1620, 1625, 1631, 1643, 1649, 1658, 1710, 1770, 1789, 1811, 1840, 1879, 1889, 1891, 1911, 1937, 1946, 1958, 1981, 1985, 2010, 2034, 2038, 2040, 2042, 2051, 2060, 2066, 2072, 2081, 2106, 2136, 2151, 2176, 2200, 2212, 2220, 2225, 2265, 2289, 2300, 2309, 2327, 2333, 2411, 2519, 2529, 2540, 2542, 2556, 2565, 2568, 2576, 2577, 2587, 2597, 2599, 2600, 2601, 2605, 2609, 2614, 2662, 2671, 2677, 2697, 2703, 2709, 2715, 2721, 2727, 2733, 2739, 2746, 2752, 2758, 2764, 2770, 2776, 2782, 2788, 2805, 2814, 2820, 2826, 2850, 2856, 2862, 2868, 2874, 2880, 2900, 2906, 2918, 2924, 2930, 2961, 2970, 2976, 2982, 2988, 2994, 3022, 3028, 3034, 3040, 3046, 3052, 3058, 3064, 3070, 3076, 3082, 3088, 3094, 3100, 3106, 3112, 3129, 3138, 3144, 3162, 3168, 3185, 3194, 3200, 3217, 3226, 3243, 3252, 3258, 3264, 3270, 3276, 3282, 3288, 3294, 3300, 3306, 3312, 3318, 3324, 3330, 3336, 3342, 3348, 3354, 3360, 3366, 3372, 3378, 3384, 3390, 3396, 3402, 3408, 3414, 3420, 3426, 3432, 3438, 3444, 3450, 3456, 3462, 3468, 3474, 3480, 3486, 3492, 3498, 3504, 3510, 3516, 3528, 3534, 3540, 3546, 3552, 3558, 3564, 3570, 3576, 3582, 3588, 3594, 3600, 3606, 3612, 3618, 3624, 3630, 3636, 3642, 3648, 3654, 3660, 3666, 3672, 3678, 3684, 3865, 3686, 3687, 3688, 3689, 3690, 3696, 3702, 3708, 3714, 3720, 3755, 3780, 3786, 3792, 3798, 3805, 3811, 3837, 3843, 3849, 3887, 3894, 3918, 3920, 3939, 3941, 3944, 3946, 3951, 3963, 3970, 4010, 4022, 4030, 4037, 4038, 4040, 4047, 4048, 4055, 4056, 4063, 4064, 4071, 4072, 4079, 4080, 4087, 4088, 4103, 4104, 4111, 4119, 4127, 4130 4136,4146,4154,4155,4162,4163,4170,4178,4179,4186,4187,4194,4195,4202,4210,4211,4218,4219,4226,4227,4234 or 4235 number is a compound,
Even more preferably, compound numbers 125, 126, 127, 128, 130, 132, 139, 140, 144, 145, 151, 163, 217, 249, 264, 265, 266, 284, 304, 308, 387, 390, 391, 459, 472, 506, 507, 515, 516, 531, 539, 541, 621, 658, 659, 662, 700, 701, 702, 704, 711, 717, 719, 733, 734, 735, 740, 758, 759, 762, 775, 780, 781, 801, 802, 803, 806, 827, 834, 835, 846, 850, 931, 964, 965, 1023, 1040, 1050, 1052, 1053, 1055, 1058, 1061, 1064, 1066, 1069, 1073, 1088, 1089, 1091, 1096, 1099, 1100, 1102, 1109, 1119, 1124, 1125, 1126, 1129, 1133, 1151, 1160, 1172, 1178, 1184, 1207, 1260, 1286, 1298, 1334, 1340, 1358, 1382, 1417, 1441, 1481, 1522, 1531, 1537, 1543, 1549, 1566, 1593, 1599, 1616, 1625, 1631, 1643, 1649, 1770, 1811, 1889, 1891, 1958, 2034, 2051, 2060, 2072, 2136, 2176, 2212, 2265, 2309, 2327, 2333, 2519, 2556, 2577, 2587, 2597, 2599, 2600, 2601, 2609, 2614, 2 662, 2677, 2697, 2709, 2715, 2721, 2727, 2733, 2739, 2746, 2752, 2758, 2764, 2770, 2776, 2782, 2788, 2805, 2814, 2820, 2826, 2850, 2862, 2868, 2874, 2900, 2918, 2924, 2930, 2961, 2970, 2988, 2994, 3022, 3034, 3046, 3058, 3064, 3076, 3082, 3094, 3106, 3112, 3129, 3144, 3162, 3168, 3185, 3217, 3243, 3252, 3264, 3282, 3288, 3294, 3306, 3324, 3330, 3336, 3354, 3378, 3390, 3396, 3402, 3408, 3414, 3420, 3426, 3432, 3438, 3450, 3462, 3468, 3474, 3486, 3492, 3510, 3516, 3546, 3552, 3564, 3582, 3588, 3594, 3600, 3606, 3612, 3618, 3624, 3642, 3654, 3660, 3678, 3685, 3686, 3687, 3688, 3689, 3690, 3696, 3702, 3780, 3786, 3798, 3805, 3811, 3837, 3843, 3849, 3887, 3894, 3918, 3920, 3939, 3941, 3944, 3946, 3951, 3963, 3970, 4010, 4022, 4030, 4037, 4038, 4040, 4047, 4048, 4055, 4056, 4071, 4072, 4079, 4080, 4087, 4088, 4103, 4104, 4111, 4130, 4136, 4146, 4154, 4155, 4162, 4163, 4170, 4178, 4179, 4186, 4187, 4194, 4195, 4202, 4210, 4211, 4218, 4219, 4226, 4227, 4234 or 4235,
Particularly preferably, the compound numbers 127, 128, 132, 139, 144, 217, 265, 284, 304, 391, 472, 506, 507, 515, 516, 539, 541, 621, 658, 659, 662, 704 , 711, 717, 719, 733, 735, 740, 758, 759, 762, 780, 781, 801, 802, 803, 806, 827, 835, 846, 850, 931, 964, 965, 1023, 1040, 1052 , 1058, 1061, 1088, 1089, 1091, 1096, 1099, 1100, 1102, 1109, 1124, 1125, 1151, 1160, 1172, 1184, 1207, 1286, 1298, 1334, 1358, 1417, 1441, 1481, 1522 , 1531, 1537, 1543, 1566, 1593, 1599, 1616, 1625, 1631, 1643, 1770, 1811, 1889, 1891, 1958, 2034, 2051, 2060, 2176, 2212, 2265, 2309, 2327, 2333, 2597 , 2599, 2614, 2662, 2677, 2727, 2733, 2739, 2746, 2752, 2805, 2814, 2850, 2862, 2900, 2918, 2961, 2994, 3022, 3046, 3064, 3094, 3129, 3144, 3168, 3185 , 3217, 3243, 3264, 3288, 3324, 3402, 3408, 3426, 3432, 3450, 3462, 3546, 3552, 3564, 3582, 3588, 3594, 3600, 3606, 3612, 3618, 3624, 3642, 3654, 3660, 3678, 3685, 3686, 3687, 3688, 3689, 3690, 3696, 3702, 3805, 3811, 3894, 3918, 3920, 3939, 3941, 3944, 3946, 3951, 3963, 3970, 4010, 4022, 4030, 4037, 4047, 4055, 4071, 4072, 4087, 4103, 4111, 4130, 4146, 4154, 4162, 4170, 4178, 4186, 4194, 4195, 4202, 4210, 4218, 4219 or 4234 And
Most preferably, 6-chloro-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 128), 6-chloro-3- (2-isopropylphenoxy) -4-pyridazinol (Compound No. 132) 6-chloro-3- (2-cyclopropylphenoxy) -4-pyridazinol (Compound No. 139), 6-chloro-3- [2- (2,2-dichlorocyclopropyl) phenoxy] -4-pyridazinol ( Compound No. 265), 6-chloro-3- (2,3-dihydro-1H-inden-4-yloxy) -4-pyridazinol (Compound No. 506), 6-chloro-3- (2-cyclopropyl- 5-methylphenoxy) -4-pyridazinol (compound number 662), 6-chloro-3- (2-fluoro-6-isopropylphenoxy) -4-pyridazinol (compound number 717), 6-chloro-3- ( 2-chloro-6-cyclopropylphenoxy) -4-pyridazinol (Compound No. 740), 6-chloro-3- (2,6-dimethylphenoxy) -4-pyridazi (Compound No. 801), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol (Compound No. 806), 6-chloro-3- [2- (2,2 -Dichlorocyclopropyl) -6-methylphenoxy] -4-pyridazinol (Compound No. 827), 6-chloro-3- (2-cyclopropyl-3,5-dimethylphenoxy) -4-pyridazinol (Compound No. 1023) ), 6-chloro-3- (6-cyclopropyl-3-fluoro-2-methylphenoxy) -4-pyridazinol (Compound No. 1052), 6-chloro-3- (6-cyclopropyl-2,3- Dimethylphenoxy) -4-pyridazinol (Compound No. 1061), 6-chloro-3- (2,3,5,6-tetramethylphenoxy) -4-pyridazinol (Compound No. 1125), 6-chloro-3- (2-Cyclopropyl-6-methylphenoxy) -4-pyridazinyl acetate (Compound No. 1151), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4- Ridazinyl propionate (compound number 1160), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-methylpropanoate (compound number 1172), 6-chloro-3- ( 2-Cyclopropyl-6-methylphenoxy) -4-pyridazinyl pivalate (Compound No. 1207), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl cyclobutanecarboxylate (Compound No. 1286) No.), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl cyclohexanecarboxylate (Compound No. 1298), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) ) -4-pyridazinyl 3-methyl-2-butenoate (Compound No. 1358), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl benzoate (Compound No. 1417), 6- Chloro-3- (2-cyclopropyl-6- Methylphenoxy) -4-pyridazinyl 2-chlorobenzoate (compound number 1441), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-methylbenzoate (compound number 1481), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-methoxybenzoate (Compound No. 1522), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy)- 4-pyridazinyl 3-methylbenzoate (compound no. 1531), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-bromobenzoate (compound no. 1543), 6-chloro- 3- (2-Cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-methylbenzoate (Compound No. 1566), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4 -Methoxybenzoate (Compound No. 1599), 6- Rho-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl phthalate (Compound No. 1625) 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl isophthalate (compound No. 1631), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl isobutyl carbonate (Compound No. 1770), 6-chloro-3- (2,6-dimethylphenoxy)- 4-pyridazinyl dimethylcarbamate (Compound No. 1889), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl dimethylcarbamate (Compound No. 1891), 6-chloro-3- (2 -Cyclopropyl-6-methylphenoxy) -4-pyridazinyl ethanesulfonate (Compound No. 2034) 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-propanesulfonate (Compound No. 2051), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-propanesulfonate (compound number 2060), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl benzenesulfonate (compound number 2176), 6-chloro-3 -(2-Cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-chlorobenzenesulfonate (Compound No. 2212), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- Methylbenzenesulfonate (Compound No. 2265), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-methoxybenzenesulfonate (Compound No. 2309), 6-chloro-3- ( 2-Cyclopropyl-6-methylphenoxy)- 4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazoyl-5-yl 1,2-benzenedisulfonate (Compound No. 2327), 6-chloro-3- (2 -Cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl 1,3-benzenedisulfonate (Compound No. 2333) ), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,3-dimethylbutanoate (Compound No. 2661), 6-chloro-3- (2-cyclopropyl- 6-methylphenoxy) -4-pyridazinyl 2-methyl acrylate (Compound No. 2677), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl ethyl succinate (Compound No. 2727), Bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] succinate (Compound No. 2733) 6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl pentandioate (compound No. 2739), bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] pentanedioate (Compound No. 2746), 6-chloro-3- (2-cyclopropyl) -6-Methylphenoxy) -4-pyridazinyl 2-bromobenzoate (Compound No. 2805), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-nitrobenzoate (Compound No. 2850) No.), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-fluorobenzoate (Compound No. 2862), 6-chloro-3- (2-cyclopropyl-6-methyl) Phenoxy) -4-pyridazinyl 4-ethylbenzoate (Compound No. 2961), 6-chloro-3- (2-cyclop Pyr-6-methylphenoxy) -4-pyridazinyl 4-cyanobenzoate (Compound No. 2994), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,3-dimethylbenzoate ( Compound No. 3046), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,4-dimethylbenzoate (Compound No. 3094), 6-chloro-3- (2-cyclo Propyl-6-methylphenoxy) -4-pyridazinyl 2,5-dimethylbenzoate (compound number 3129), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-fluoro-4 -Methylbenzoate (compound number 3185), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,5-difluorobenzoate (compound number 3217), 6-chloro-3- (2-Cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,5-dimethylbenzoe (Compound number 3243), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-methyl-2-thiophenecarboxylate (compound number 3324), 6-chloro- 3- (2-Cyclopropyl-6-methylphenoxy) -4-pyridazinyl methoxy (methyl) carbamate (Compound No. 3564), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl Bis (2-methoxyethyl) carbamate (Compound No. 3600), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-azetidinecarboxylate (Compound No. 3612), 6 -Chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3687), 6-chloro-3- (2,3-dihydro-1H-inden-4-yloxy)- 4-pyridazinyl 4-morpholine carboxylate (Compound No. 3688) 6-chloro-3- (2,6-dimethylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3689), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4- Pyridazinyl 4-morpholine carboxylate (Compound No. 3690), 6-chloro-3- (2,3,5,6-tetramethylphenoxy) -4-pyridazinyl dimethyl carbamate (Compound No. 3894), 6-chloro-3 -(2-Chloro-6-methylphenoxy) -4-pyridazinyl 4-morpholine carboxylate (Compound No. 3944), 3- (2-Bromo-6-methylphenoxy) -6-chloro-4-pyridazinyl 4-morpholine Carboxylate (compound number 3946), 6-chloro-3- (2-ethyl-6-methylphenoxy) -4-pyridazinyl 4-morpholine carboxylate (compound number 3951), 6-chloro-3-[(5 -Methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 4-morpho Carboxylate (compound number 3963), 6-chloro-3- (2,3,5,6-tetramethylphenoxy) -4-pyridazinyl 4-morpholine carboxylate (compound number 3970), 6-chloro-3 -(2-Cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1,3-oxazolidine-3-carboxylate (Compound No. 4010), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-cyano-1-piperazinecarboxylate (Compound No. 4111), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,6-dihydro-1 (2H ) -Pyridinecarboxylate (Compound No. 4194), 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1,3-dihydro-2H-isoindole-2-carboxylate (Compound) No. 4218) and 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyrida Dinyl 2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate (Compound No. 4234).

  The herbicidal composition of the present invention can be killed beyond the application range obtained with each single agent by mixing and applying the 3-phenoxy-4-pyridazinol derivative and the second herbicidally active compound, which are the active ingredients. The grass width is expanded. The herbicidal width of the composition of the present invention extends to general perennial weeds such as Gramineae, annual broad-leaved weeds, Omodakaceae and Cyperaceae. Furthermore, the composition of the present invention is highly safe for paddy rice and has a wide application period. In addition, the composition of the present invention exhibits a synergistic effect on the herbicidal effect, and exhibits its effect sufficiently when the active ingredients are mixed at a dose much lower than the dose when each active ingredient is used alone. As a result, the composition of the present invention increases the herbicidal efficacy enough to be a single treatment, and the efficacy lasts for a long time. Further, the composition of the present invention has no phytotoxicity to paddy rice and can be treated before transplantation and immediately after transplanting.

  The 3-phenoxy-4-pyridazinol compound and its ester derivative of the present invention can be produced by the methods of Steps A to Q described below.

  (Process A)

In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are as defined above,
L represents a leaving group, for example, a halogen atom, a C _{1 to} C ₆ alkylsulfonyloxy group or a phenylsulfonyloxy group (the phenylsulfonyloxy group is the same or different 1 to 5 halogen atoms or C ₁ the -C ₆ alkyl group may be substituted.), and obtained,
X represents a hydrogen atom or an acyl group,
Y is other protective group of hydroxyl group besides X, and may be, for example, methyl group, methoxymethyl group, methoxyethoxymethyl group or benzyl group.

  In step A, the pyridazine compound represented by the general formula (II) is reacted with the phenol compound represented by the general formula (III), then chlorinated, and further reacted with an oxygen nucleophile to thereby produce the compound of the present invention. It is a step of producing a compound in which the hydroxyl group represented by (Ia) or general formula (VII) is protected, and further, a step of producing the compound (Ib) of the present invention by removing the protecting group of compound (VII). .

(Process A-1)
In step A-1, compound (II) is reacted with compound (III) in the presence or absence of a solvent, and optionally in the presence of a base, to convert a phenoxypyridazine compound represented by the general formula (IV). It is a manufacturing process.

  The base to be used is not particularly limited as long as it usually has a pH of 8 or more. For example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkalis such as sodium carbonate, potassium carbonate and cesium carbonate Metal carbonates; metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metals such as sodium and potassium; triethylamine and tributylamine Aliphatic tertiary amines such as diisopropylethylamine; 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) Aliphatic cyclic tertiary amines such as: pyridine, collidine Pyridines such as 4- (N, N-dimethylamino) pyridine; organometallic bases such as n-butyllithium, s-butyllithium, lithium diisopropylamide, sodium bis (trimethylsilyl) amide, lithium bis (trimethylsilyl) amide And is preferably an alkali metal hydroxide, alkali metal carbonate, metal alkoxide, alkali metal hydride or alkali metal, more preferably potassium carbonate, potassium t-butoxide, sodium hydride or Sodium.

  The amount of the base used is usually 0.5 to 5 mol and preferably 1 to 3 mol with respect to 1 mol of compound (II).

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, water; alcohols such as methanol, ethanol, t-butanol; acetone, methyl isobutyl ketone Ketones such as acetonitrile; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; ethers such as diethyl ether, tetrahydrofuran and dioxane; Aromatic hydrocarbons such as: amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; or a mixed solvent thereof, preferably nitriles, halogenated hydrocarbons , Ethers, aromatic hydrocarbons An amide or a sulfoxide, and more preferably dioxane, toluene, dimethylformamide or dimethyl sulfoxide.

  The reaction temperature varies depending on the raw material compound, the reaction reagent, the solvent and the like, but is usually -90 ° C to 200 ° C, and preferably 0 ° C to 100 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the type of solvent used, it is generally 5 minutes to 48 hours, preferably 15 minutes to 12 hours.

(Process A-2)
In step A-2, compound (IV) is chlorinated with a chlorinating agent in the presence or absence of a solvent to produce a compound in which a chlorine atom is introduced at the 4-position of the pyridazine ring represented by general formula (V). It is a process to do.

  The chlorinating agent to be used is not particularly limited as long as it chlorinates an aromatic ring, and examples thereof include chlorine, chlorine-iron chloride, sulfuryl chloride, copper chloride, N-chlorosuccinimide, and phosphorus pentachloride. Preferably, it is chlorine.

  The amount of the chlorinating agent to be used is usually 0.5 to 10 mol, preferably 1 to 2 mol, relative to 1 mol of compound (IV).

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. Examples thereof include phosphorus oxychloride; water; alcohols such as methanol, ethanol and t-butanol; Halogenated hydrocarbons such as methylene, chloroform and dichloroethane; ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as toluene; amides such as dimethylformamide and dimethylacetamide; dimethyl sulfoxide Such sulfoxides; aliphatic hydrocarbons such as hexane, cyclohexane, heptane; or a mixed solvent thereof, preferably phosphorus oxychloride, water, halogenated hydrocarbons or ethers; More preferred is phosphorus oxychloride.

  The reaction temperature varies depending on the raw material compound, the reaction reagent, and the type of solvent used, but is usually −90 ° C. to 200 ° C., and preferably 0 ° C. to 50 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the type of solvent used, it is usually 5 minutes to 24 hours, and preferably 15 minutes to 6 hours.

(Process A-3)
In step A-3, compound (V) is reacted with an oxygen nucleophile represented by general formula (VI) in the presence or absence of a solvent, and optionally in the presence of a base, to give compound (Ia) of the present invention. Or it is the process of manufacturing the compound by which the hydroxyl group represented by general formula (VII) was protected.

  The base to be used is not particularly limited as long as it is a base exhibiting a pH of 8 or higher. Examples thereof include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; sodium carbonate, potassium carbonate and cesium carbonate. Alkali metal carbonates; metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide; alkali metal salts of organic acids such as sodium acetate, potassium acetate, sodium formate, potassium formate; sodium hydride, hydrogenation Alkali metal hydrides such as potassium; alkali metals such as sodium and potassium; aliphatic tertiary amines such as triethylamine, tributylamine and diisopropylethylamine; 1,4-diazabicyclo [2.2.2] octane (DABCO) ), 1,8-diazabicyclo 5.4.0] Aliphatic cyclic tertiary amines such as undec-7-ene (DBU); pyridines such as pyridine, collidine, 4- (N, N-dimethylamino) pyridine; butyllithium, s -Organic bases such as butyl lithium, lithium diisopropylamide, sodium bis (trimethylsilyl) amide, lithium bis (trimethylsilyl) amide, preferably alkali metal hydroxides, alkali metal carbonates, metal alkoxides, Alkali metal salt of organic acid, alkali metal hydride or alkali metal, more preferably sodium hydroxide, potassium hydroxide, potassium carbonate, potassium t-butoxide, sodium acetate, sodium formate, sodium hydride or sodium is there.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, water; alcohols such as methanol, ethanol, t-butanol; acetone, methyl isobutyl Ketones such as ketones; Nitriles such as acetonitrile; Esters such as ethyl acetate; Halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; Ethers such as diethyl ether, tetrahydrofuran and dioxane; Toluene Aromatic hydrocarbons such as: amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; or a mixed solvent thereof, preferably water, alcohols, nitriles, Ethers, amides or sulfoxides By weight, more preferably, water, methanol, acetonitrile, tetrahydrofuran, dioxane, dimethylformamide or dimethyl sulfoxide.

  The reaction temperature varies depending on the raw material compound, the reaction reagent, and the type of solvent used, but is usually −90 ° C. to 200 ° C., and preferably 0 ° C. to 100 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the type of solvent used, it is usually 5 minutes to 24 hours, and preferably 15 minutes to 6 hours.

  In this step, compound (VI) can also be used in this step after previously reacting with a base to form a salt.

(Process A-4)
Step A-4 is a step for producing the compound (Ib) of the present invention by removing the protecting group for the hydroxyl group of the compound (VII).

  The protecting group used in this step is not particularly limited as long as it can be selectively removed from compound (VII) to give compound (Ib). For example, methyl, methoxymethyl, benzyloxymethyl, methoxy Ethoxymethyl group, 2- (trimethylsilyl) ethoxymethyl group, methylthiomethyl group, phenylthiomethyl group, 2,2-dichloro-1,1-difluoroethyl group, tetrahydropyranyl group, phenacyl group, p-bromophenacyl group, cyclo Propylmethyl group, allyl group, isopropyl group, cyclohexyl group, t-butyl group, benzyl group, 2,6-dimethylbenzyl group, 4-methoxybenzyl group, 2-nitrobenzyl group, 2,6-dichlorobenzyl group, 4 -(Dimethylaminocarbonyl) benzyl group, 9-anthrylmethyl group, 4- It can be a cholyl group, a heptafluoro-p-tolyl group or a tetrafluoro-4-pyridyl group, preferably a methyl group, a methoxymethyl group, a methoxyethoxymethyl group, a methylthiomethyl group, a tetrahydropyranyl group, a phenacyl group, It is an allyl group or a benzyl group, and more preferably a methyl group.

  The method for removing the protecting group used in this step is not particularly limited as long as it can selectively remove the protecting group of the hydroxyl group, and a known method (for example, Protective Groups In -Organic Synthesis (Protective Groups in Organic Synthesis), 13th edition, Theodora W. Greene and Peter GM Wuts, the method described in JOHN WILEY & SONS, INC) or according to these methods. For example, when the protecting group is a methyl group, the removal of the methyl group can be accomplished, for example, by the potassium or sodium salt of 2-hydroxypyridine in dimethyl sulfoxide, the sodium salt of ethanethiol in dimethylformamide, or 3 in methylene chloride. It can be performed by the action of boron bromide. For example, when the protecting group is a methoxymethyl group, the removal of the methoxymethyl group can be performed, for example, by the action of trifluoroacetic acid. For example, when the protecting group is a methoxyethoxymethyl group, the removal of the methoxyethoxymethyl group can be performed by, for example, acting trifluoroacetic acid. For example, when the protecting group is a benzyl group, the benzyl group can be removed by catalytic hydrogenation.

  (Process B)

In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , L, X and Y are as defined above.

  In step B, the pyridazine compound represented by the general formula (II) is oxidized, reacted with the phenol compound represented by the general formula (III), then chlorinated, and further reacted with an oxygen nucleophile. A step of producing a compound (Ia) or a compound in which the hydroxyl group represented by the general formula (VII) is protected, and further, a step of producing the compound (Ib) of the present invention by removing the protecting group of the compound (VII). It is.

(Process B-1)
Step B-1 is a step of producing pyridazine N-oxide represented by general formula (VIII) by oxidizing compound (II) with an oxidizing agent in the presence or absence of a solvent.

  The oxidizing agent used is not particularly limited as long as it converts amines to N-oxide. For example, m-chloroperbenzoic acid (mcpba), peracetic acid, pertrifluoroacetic acid, trifluoroacetic anhydride- Hydrogen peroxide, peroxydichloromaleic acid, dichloromaleic acid-hydrogen peroxide, peroxymaleic acid, maleic acid-hydrogen peroxide, t-butyl hydroperoxide, t-butyl hydroperoxide-vanadium oxyacetylacetonate, t-butyl hydroperoxide-peroxide such as molybdenum chloride, hydrogen peroxide; ozone; or oxygen, preferably m-chloroperbenzoic acid (mcpba), trifluoroacetic anhydride-hydrogen peroxide Or dichloromaleic acid-hydrogen peroxide.

  The amount of the oxidizing agent used for the reaction is usually 0.5 to 100 mol, preferably 1 to 2 mol, relative to 1 mol of compound (II).

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, water; alcohols such as methanol, ethanol, t-butanol; acetone, methyl isobutyl ketone Ketones such as acetonitrile; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; ethers such as diethyl ether, tetrahydrofuran and dioxane; Aromatic hydrocarbons; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; or a mixed solvent thereof, preferably halogenated hydrocarbons, more preferably Is methylene chloride.

  While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally -90 ° C to 200 ° C, preferably 0 ° C to 100 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the type of solvent used, it is generally 5 minutes to 24 hours, preferably 15 minutes to 6 hours.

  By this process, isomers in which other nitrogen atoms are oxidized may be by-produced.However, by purifying after completion of this process or by performing subsequent processes while mixing, purifying after completion of the process, The target pyridazine N-oxide can be obtained.

(Process B-2)
In step B-2, compound (VIII) is reacted with compound (III) in the presence or absence of a solvent, and optionally in the presence of a base, to produce a phenoxypyridazine compound represented by general formula (IX). It is a process to do.

  This step can be performed according to step A-1.

(Process B-3)
Step B-3 is a step of producing compound (V) by reacting compound (IX) with phosphorus oxychloride in the presence or absence of a solvent.

  The amount of phosphorus oxychloride used in this step is usually 0.5 to 100 mol, preferably 1 to 5 mol, relative to 1 mol of compound (IX).

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, ketones such as acetone and methyl isobutyl ketone; nitriles such as acetonitrile; ethyl acetate Esters such as; Halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; Ethers such as diethyl ether, tetrahydrofuran and dioxane; Aromatic hydrocarbons such as toluene; Dimethylformamide and dimethylacetamide Amides; Sulfoxides such as dimethyl sulfoxide; Aliphatic hydrocarbons such as hexane and cyclohexane; or a mixed solvent thereof, preferably halogenated hydrocarbons, and more preferably Methylene chloride or chloroform.

  While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally -90 ° C to 200 ° C, preferably 0 ° C to 100 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the type of solvent used, it is generally 5 minutes to 72 hours, and preferably 30 minutes to 24 hours.

(Process B-4)
In Step B-4, the compound (V) is reacted with an oxygen nucleophile represented by the general formula (VI) in the presence or absence of a solvent, and optionally in the presence of a base, to give the compound of the present invention (Ia ) Or a compound in which the hydroxyl group represented by formula (VII) is protected.

  This step is the same as step A-3.

(Process B-5)
Step B-5 is a step for producing the compound (Ib) of the present invention by removing the protecting group for the hydroxyl group of the compound (VII).

  This step is the same as step A-4.

  (Process C)

In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X and Y are as defined above.

  Step C is a step of producing a compound in which the hydroxyl group represented by the present compound (Ia) or general formula (VII) is protected by oxidizing and chlorinating compound (IV) and then reacting with an oxygen nucleophile. Furthermore, this is a step for producing the compound (Ib) of the present invention by removing the protecting group of the compound (VII).

(Process C-1)
Step C-1 is a step of producing pyridazine N-oxide represented by general formula (IX) by oxidizing compound (IV) with an oxidizing agent in the presence or absence of a solvent.

  This process can be performed according to process B-1.

(Process C-2)
Step C-2 is a step of producing compound (V) by reacting compound (IX) with phosphorus oxychloride in the presence or absence of a solvent.

  This step is the same as step B-3.

(Process C-3)
In Step C-3, the compound (V) is reacted with an oxygen nucleophile represented by the general formula (VI) in the presence or absence of a solvent, and optionally in the presence of a base, to give a compound of the present invention ( This is a step of producing a compound in which the hydroxyl group represented by Ia) or general formula (VII) is protected.

  This step is the same as step A-3 or B-4.

(Process C-4)
Step C-4 is a step for producing the compound (Ib) of the present invention by removing the protecting group for the hydroxyl group of the compound (VII).

  This step is the same as step A-4 or B-5.

  (Process D)

In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , L, X and Y are as defined above.

  In the step D, the compound represented by the present invention (Ia) or the general formula (I) is reacted with a phenol represented by the general formula (III) by reacting the pyridazine compound represented by the general formula (X) with the oxygen functional group previously substituted. VII) is a step of producing a compound in which the hydroxyl group is protected, and further is a step of producing the compound (Ib) of the present invention by removing the protecting group of compound (VII).

(Process D-1)
In step D-1, compound (X) is reacted with compound (III) in the presence or absence of a solvent, optionally in the presence of a base, to give compound (Ia) or general formula (VII) of the present invention. This is a process for producing a compound in which the hydroxyl group represented is protected.

  This process can be performed according to process A-1 or B-2.

(Process D-2)
Step D-2 is a step for producing the compound (Ib) of the present invention by removing the protecting group for the hydroxyl group of the compound (VII).

  This step is the same as step A-4, B-5 or C-4.

  (Process E)

In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , L, X and Y are as defined above,
m ′ and n ′ represent 0 or 1, provided that m ′ and n ′ are not 0 at the same time.

  In step E, the pyridazine compound previously substituted with an oxygen functional group represented by the general formula (X) is oxidized and then reacted with the phenol represented by the general formula (III) to thereby react the compound (Ic) of the present invention or This is a step of producing a compound in which the hydroxyl group represented by the general formula (XII) is protected, and further, a step of producing the compound (Id) of the present invention by removing the protecting group of the compound (XII).

(Process E-1)
Step E-1 is a step of producing pyridazine N-oxide represented by general formula (XI) by oxidizing compound (X) with an oxidizing agent in the presence or absence of a solvent.

  This step can be performed according to Step B-1 or C-1 when m ′ = 0 or n ′ = 0, and when m ′ = n ′ = 1, the amount of oxidizing agent is excessive. Or by using more severe conditions such as oxidizing with a more reactive oxidizing agent.

(Process E-2)
In step E-2, compound (XI) is reacted with compound (III) in the presence or absence of a solvent, and optionally in the presence of a base, to give a compound of the present invention (Ic) or general formula (XII). This is a step of producing a compound in which the hydroxyl group represented is protected.

  This process can be performed according to process A-1, B-2, or D-1.

(Process E-3)
Step E-3 is a step of producing the compound (Id) of the present invention by removing the protecting group for the hydroxyl group of the compound (XII).

  This step is the same as step A-4, B-5, C-4 or D-2.

  (Process F)

In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, Y, m ′ and n ′ are as defined above.

  In Step F, the hydroxyl group represented by the compound (Ic) or the general formula (XII) is protected by oxidizing the compound represented by the compound (Ia) or the general formula (VII). And a step of producing the compound (Id) of the present invention by removing the protecting group of the compound (XII).

(Process F-1)
In Step F-1, the compound (Ia) or compound (VII) of the present invention is oxidized with an oxidizing agent in the presence or absence of a solvent, and is represented by the compound (Ic) or general formula (XII) of the present invention. This is a production process for producing a compound in which a hydroxyl group is protected.

  This step can be performed according to step E-1.

(Process F-2)
Step F-2 is a step of producing the compound (Id) of the present invention by removing the hydroxyl-protecting group of the compound (XII).

  This step is the same as Step A-4, B-5, C-4, D-2 or E-3.

  (Process G)

In the above formula, R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X and Y are as defined above,
R ^2a has the same meaning as R ² except for a hydrogen atom.

  In Step G, the 5-position of the pyridazine ring of the compound (Ie) or the compound represented by the general formula (XIII) in which the hydroxyl group is protected is metalated and then reacted with an electrophile, If) is a step of producing a compound in which the hydroxyl group represented by formula (XIV) is protected, and further is a step of producing the compound (Ig) of the present invention by removing the protecting group of compound (XIV). .

(Process G-1)
In Step G-1, the compound of the present invention (Ie) or the compound represented by formula (XIII) in which the hydroxyl group is protected is reacted with a metallizing agent in the presence or absence of a solvent, This is a step of producing a compound in which the hydroxyl group represented by the present compound (If) or general formula (XIV) is protected by reacting.

  The metallizing agent to be used is not particularly limited as long as it can metallate an aromatic ring. For example, an organolithium compound such as methyl lithium, butyl lithium, sec-butyl lithium, t-butyl lithium, or phenyl lithium; Organomagnesium compounds such as magnesium chloride, methylmagnesium bromide, ethylmagnesium bromide, phenylmagnesium bromide; Organometallic amides such as lithium diisopropylamide, sodium bis (trimethylsilyl) amide, lithium bis (trimethylsilyl) amide; sodium methoxide, sodium Metal alkoxides such as ethoxide and potassium t-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; lithium, sodium and potassium Alkali metals such as beam; obtained an alkali earth metal such as magnesium, preferably an organolithium compound, more preferably a butyl lithium.

  The amount of the metallizing agent used in the reaction is usually 0.5 to 10 mol, preferably 1 to 2 mol, relative to 1 mol of compound (Ie) or compound (XIII).

  The electrophile used in the reaction is not particularly limited as long as it reacts with an organometallic compound. For example, silylating agents such as trimethylsilyl chloride, triethylsilyl chloride, t-butyldimethylsilyl chloride, trimethylsilyl trifluoromethanesulfonate, etc. Acylating agents such as acetyl chloride, benzoyl chloride, ethyl chlorocarbonate, methyl chlorocarbonate, N, N-dimethylformamide, methyl formate; carbonyl compounds such as acetaldehyde, benzaldehyde, acetone, cyclohexanone; methyl iodide, bromide Alkylating agents such as methyl and benzyl bromide; fluorine, chlorine, bromine, iodine, N-fluorobenzenesulfonamide, 1-fluoro-2,6-dichloropyridinium triflate, N-chlorosuccinimide (NCS) ), A halogenating agent such as N-bromosuccinimide (NBS); or carbon dioxide, preferably a silylating agent, acylating agent, alkylating agent or halogenating agent, more preferably Is trimethylsilyl chloride, benzoyl chloride, ethyl chlorocarbonate or methyl iodide.

  The amount of the electrophile used for the reaction is usually 0.5 to 10 mol, preferably 1 to 3 mol, relative to 1 mol of compound (Ie) or compound (XIII).

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane; diethyl ether, tetrahydrofuran, dioxane Ethers such as toluene; aromatic hydrocarbons such as toluene; aliphatic hydrocarbons such as hexane and cyclohexane; or a mixed solvent thereof, preferably ethers, more preferably Is tetrahydrofuran.

  While the reaction temperature varies depending on the raw material compound, the reaction reagent, and the type of solvent used, it is generally −90 ° C. to 100 ° C., and preferably −70 ° C. to 30 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the type of solvent used, it is generally 5 minutes to 24 hours, preferably 30 minutes to 12 hours.

(Process G-2)
Step G-2 is a step for producing the compound (Ig) of the present invention by removing the protecting group for the hydroxyl group of the compound (XIV).

  This step is the same as Step A-4, B-5, C-4, D-2, E-3 or F-2.

  (Process H)

In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are as defined above,
X ^a has the same meaning as X except for a hydrogen atom.

  Step H is a step of converting the ester derivative of the present invention represented by the general formula (Ih) into the hydroxy form of the present invention represented by the general formula (Ib).

(Process H-1)
Step H-1 is a step of producing the present compound (Ib) by reacting the present compound (Ih) with a nucleophile in the presence or absence of a solvent.

  The nucleophile used is not particularly limited as long as it can nucleophilically attack an ester derivative and cleave the ester bond into an acid moiety and an alcohol moiety. For example, water; lithium hydroxide, sodium hydroxide Alkali metal hydroxides such as potassium hydroxide; alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide; sodium methoxide, sodium ethoxide, 2-hydroxypyridine potassium salt, 2- Metal alkoxides such as hydroxypyridine sodium salt; alkali metal salts of organic acids such as sodium acetate, potassium acetate, sodium formate and potassium formate; fluorides such as tetrabutylammonium fluoride and potassium fluoride; lithium chloride and chloride Chlorides such as sodium; lithium bromide, sodium bromide Bromides; iodides such as sodium iodide and potassium iodide; or metal salts of sulfur compounds such as methanethiol sodium salt and ethanethiol sodium salt, preferably water, alkali metal hydroxides , Metal alkoxides or alkali metal salts of organic acids, more preferably water, sodium hydroxide, potassium hydroxide or sodium acetate.

  The amount of the nucleophile to be used is usually 1 to 10 mol, preferably 1 to 5 mol, relative to 1 mol of compound (Ih).

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, water; alcohols such as methanol, ethanol, t-butanol; acetone, methyl isobutyl ketone Ketones such as acetonitrile; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; ethers such as diethyl ether, tetrahydrofuran and dioxane; Aromatic hydrocarbons; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethylsulfoxide; or a mixed solvent thereof, preferably water, alcohols, nitriles, ethers Amides or sulfoxides , More preferably, water, methanol, ethanol, tetrahydrofuran, dioxane, dimethylformamide or dimethyl sulfoxide.

  While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally -90 ° C to 200 ° C, preferably 0 ° C to 100 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the type of solvent used, it is usually 5 minutes to 48 hours, preferably 15 minutes to 12 hours.

  In addition, this process can also use a well-known method as normal deprotection of a hydroxyl group.

  (Process I)

In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and X ^a are as defined above.

  Step I is a step of converting the hydroxy compound of the present invention represented by the general formula (Ib) into the ester derivative of the present invention represented by the general formula (Ih).

(Step I-1)
Step I-1 is a step of producing the present compound (Ih) by reacting the present compound (Ib) with an esterifying agent in the presence or absence of a solvent.

  The esterifying agent used is not particularly limited as long as it esterifies a hydroxyl group. For example, acetyl chloride, acetyl bromide, acetic anhydride, trifluoroacetic anhydride, benzoyl chloride, toluoyl chloride, methyl chlorocarbonate, Acylating agents such as ethyl chlorocarbonate, N, N-dimethylcarbamoyl chloride, 4-morpholine carbonyl chloride, methyl chlorothioformate; or methanesulfonyl chloride, propanesulfonyl chloride, p-toluenesulfonyl chloride, anhydrous trifluoromethanesulfone Acid, may be a sulfonylating agent such as N, N-dimethylsulfamoyl chloride, and preferably acetyl chloride, acetic anhydride, trifluoroacetic anhydride, benzoyl chloride, toluoyl chloride, methyl chlorocarbonate, chlorocarbonic acid Ethyl, N, N-dimethylcarbamoyl chloride, 4-morpholine carbonyl chloride, methanesulfonyl chloride, propanesulfonyl chloride, p-toluenesulfonyl chloride or trifluoromethanesulfonic anhydride, more preferably benzoyl chloride, toluoyl chloride, N, N-dimethylcarbamoyl chloride, 4-morpholine carbonyl chloride, p-toluenesulfonyl chloride or trifluoromethanesulfonic anhydride.

  The amount of the esterifying agent used in the reaction is usually 0.5 to 10 mol, preferably 1 to 3 mol, relative to 1 mol of compound (Ib).

  The reaction is preferably carried out in the presence of a base.

  The base used is not particularly limited as long as it usually shows a pH of 8 or more. For example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkalis such as sodium carbonate, potassium carbonate and cesium carbonate Metal carbonates; metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; aliphatic triions such as triethylamine, tributylamine and diisopropylethylamine Tertiary amines; aliphatic cyclic tertiary amines such as 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) Of pyridine, collidine, 4- (N, N-dimethylamino) pyridine Or pyridines; or organometallic bases such as n-butyllithium, sec-butyllithium, lithium diisopropylamide, sodium bis (trimethylsilyl) amide, lithium bis (trimethylsilyl) amide, and preferably aliphatic Tertiary amines, aliphatic cyclic tertiary amines or pyridines, more preferably triethylamine, 1,4-diazabicyclo [2.2.2] octane (DABCO), pyridine or 4- (N, N -Dimethylamino) pyridine.

  The amount of the base used for the reaction is usually 0.5 to 20 mol, preferably 1 to 5 mol, relative to 1 mol of compound (Ib).

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, ketones such as acetone and methyl isobutyl ketone; nitriles such as acetonitrile; ethyl acetate Esters such as; Halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; Ethers such as diethyl ether, tetrahydrofuran and dioxane; Aromatic hydrocarbons such as toluene; Aliphatics such as hexane and cyclohexane Hydrocarbons; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; or a mixed solvent thereof, preferably nitriles, halogenated hydrocarbons or ethers, More preferably, acetonitrile or salt It is methylene.

  The reaction temperature mainly varies depending on the raw material compound, the reaction reagent, and the type of solvent used, but is usually −90 ° C. to 200 ° C., and preferably 0 ° C. to 100 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the type of solvent used, it is usually 5 minutes to 48 hours, preferably 15 minutes to 12 hours.

  In addition, this process can also use a well-known method as protection of a normal hydroxyl group.

  (Process J)

In the above formula, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X and Y are as defined above,
R ^1a has the same meaning as R ¹ except for a hydrogen atom.

  In Step J, the 6-chloropyridazine derivative represented by the general formula (IVa) is reduced, oxidized, metalated, and reacted with an electrophile to introduce a substituent at the 6-position of the pyridazine ring. Further, it is a step of producing a compound in which the hydroxyl group represented by the compound (Ii) or general formula (XVIII) of the present invention is protected by chlorination and substitution reaction with an oxygen nucleophile. In this step, the protecting group is removed to produce the compound (Ij) of the present invention.

(Process J-1)
Step J-1 is a compound wherein R ¹ is a chlorine atom in the compound (IV) and (IVa), the presence of a solvent or absence, by reacting with a reducing agent, wherein R ¹ is hydrogen in the compound (IV) In this step, compound (IVb), which is an atom, is produced.

  The reducing agent used in the reaction is not particularly limited as long as it can reduce the chlorine atom on the aromatic ring. For example, it can be a reducing agent used in a normal hydrogenation reaction, preferably a hydrogen-palladium catalyst. It is.

  In the case of hydrogenation reaction in this step, the hydrogen pressure is usually 1 atm to 100 atm, and preferably 1 to 3 atm.

  The amount of palladium used for the hydrogenation reaction is usually 0.001 to 10 mol, preferably 0.01 to 1 mol, relative to 1 mol of compound (IVa).

  The hydrogenation reaction is preferably performed in the presence of a base.

  The base used is not particularly limited as long as it usually shows a pH of 8 or more. For example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkalis such as sodium carbonate, potassium carbonate and cesium carbonate Metal carbonates; metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; aqueous ammonia; triethylamine, tri-n-butylamine, diisopropylethylamine Fatty tertiary amines such as: 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) Group cyclic tertiary amines; pyridine, collidine, 4- (N, N-dimethyl) Pyridine) such as mino) pyridine; or organometallic bases such as butyllithium, sec-butyllithium, lithium diisopropylamide, sodium bis (trimethylsilyl) amide, lithium bis (trimethylsilyl) amide, etc. Is ammonia water or aliphatic tertiary amines, more preferably ammonia water or triethylamine.

  The amount of the base used in the reaction is usually 0.1 to 100 mol, preferably 1 to 3 mol, relative to 1 mol of compound (IVa).

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, water; alcohols such as methanol, ethanol, t-butanol; acetone, methyl isobutyl ketone Ketones such as acetonitrile; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; ethers such as diethyl ether, tetrahydrofuran and dioxane; Aromatic hydrocarbons; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; aliphatic hydrocarbons such as hexane and cyclohexane; or a mixed solvent thereof, preferably Are alcohols, yo Preferably methanol or ethanol.

  The reaction temperature mainly varies depending on the raw material compound, the reaction reagent, and the type of solvent used, but is usually −90 ° C. to 200 ° C., and preferably 0 ° C. to 100 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the type of solvent used, it is usually 5 minutes to 48 hours, preferably 15 minutes to 12 hours.

(Process J-2)
Step J-2 is a step of producing pyridazine N-oxide represented by general formula (XV) by oxidizing compound (IVb) with an oxidizing agent in the presence or absence of a solvent.

  This process can be performed according to process B-1 or C-1.

(Process J-3)
Step J-3 is a step of producing the compound (XVI) of the present invention by reacting the compound (XV) with a metallating agent in the presence or absence of a solvent and then reacting with an electrophile. is there.

  This process can be performed according to the process G-1.

(Process J-4)
Step J-4 is a step of producing compound (XVII) by reacting compound (XVI) with phosphorus oxychloride in the presence or absence of a solvent.

  This step is the same as step B-3 or C-2.

(Process J-5)
In Step J-5, compound (XVII) is reacted with an oxygen nucleophile represented by the general formula (VI) in the presence or absence of a solvent, and optionally in the presence of a base, to give a compound of the present invention ( This is a step of producing a compound in which the hydroxyl group represented by Ii) or general formula (XVIII) is protected.

  This step is the same as step A-3, B-4 or C-3.

(Process J-6)
Step J-6 is a step for producing the compound (Ij) of the present invention by removing the protecting group for the hydroxyl group of the compound (XVIII).

  This step is the same as Step A-4, B-5, C-4, D-2, E-3, F-2 or G-2.

  (Process K)

In the above formula, R ^1a , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X and Y are as defined above.

  In step K, the 6-chloropyridazine derivative of the present invention represented by the general formula (Ik) or the 6-chloropyridazine derivative protected by the hydroxyl group represented by the general formula (XIX) is oxidized, dechlorinated, and then It is a step of producing a compound in which the hydroxyl group represented by the compound (Ii) of the present invention or the general formula (XVIII) is protected by introducing an electrophile after metalation and finally reducing the compound. XVIII) is a process for producing the compound (Ij) of the present invention by removing the protecting group.

(Process K-1)
In step K-1, compound (Ik) or compound (XIX) is oxidized with an oxidizing agent in the presence or absence of a solvent to give an N-oxypyridazine compound represented by general formula (Il) or (XX) Is a process of manufacturing.

  This process can be performed according to process B-1, C-1, or J-2.

(Process K-2)
In Step K-2, N-oxide compound (Il) or (XX) in which the pyridazine ring 6-position is a chlorine atom is reacted with a reducing agent in the presence or absence of a solvent, whereby the pyridazine ring 6-position is This is a step for producing an N-oxide compound (Im) or (XXI) which is a hydrogen atom.

  This step can be performed according to step J-1.

(Process K-3)
In Step K-3, the compound (Im) or (XXI) is reacted with a metallizing agent in the presence or absence of a solvent and then reacted with an electrophile, whereby the compound (In) of the present invention or In this step, the hydroxyl group represented by the general formula (XXII) is protected.

  This process can be performed according to the process G-1 or J-3.

(Process K-4)
Step K-4 is performed by reacting the N-oxide derivative represented by the general formula (In) or (XXII) with phosphorus trichloride or phosphorus tribromide in the presence or absence of a solvent. This is a step for producing a compound in which the hydroxyl group represented by compound (Ii) or general formula (XVIII) is protected.

  The amount of phosphorus trichloride or phosphorus tribromide used is usually 0.5 to 100 mol, preferably 1 to 20 mol, relative to 1 mol of compound (In) or (XXII).

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane; diethyl ether, tetrahydrofuran, dioxane Ethers such as toluene; aromatic hydrocarbons such as toluene; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; or These may be mixed solvents, preferably halogenated hydrocarbons, and more preferably chloroform.

  The reaction temperature mainly varies depending on the raw material compound, the reaction reagent, and the type of solvent used, but is usually −90 ° C. to 200 ° C., and preferably 0 ° C. to 100 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the type of solvent used, it is generally 5 minutes to 24 hours, preferably 15 minutes to 6 hours.

(Process K-5)
Step K-5 is a step for producing the compound (Ij) of the present invention by removing the protecting group for the hydroxyl group of the compound (XVIII).

  This step is the same as step A-4, B-5, C-4, D-2, E-3, F-2, G-2 or J-6.

  (Process L)

In the above formula, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X and Y are as defined above,
R ^1b has the same meaning as R ¹ except for a hydrogen atom and a halogen atom.

  In step L, a 6-chloropyridazine derivative represented by the general formula (Ik) or (XIX) is reacted with an organometallic compound to thereby produce a hydroxyl group represented by the present compound (Io) or the general formula (XXIII). Is a step for producing a protected compound, and further is a step for producing the compound (Ip) of the present invention by removing the protecting group of compound (XXIII).

(Process L-1)
In Step L-1, compound (Ik) or (XIX) is reacted with an organometallic compound in the presence or absence of a solvent and in the presence of a metal catalyst to give a compound of the present invention (Io) or general formula ( XXIII) is a step of producing a compound in which the hydroxyl group is protected.

The organometallic compound used is not particularly limited as long as it is used for the cross-coupling reaction in which the R ^1b group is substituted with a chlorine atom. For example, organic compounds such as methyl magnesium chloride, ethyl magnesium bromide, and phenyl magnesium chloride are used. Magnesium compounds; organozinc compounds such as phenylzinc chloride; organoaluminum compounds such as (diisobutyl) (1-hexenyl) aluminum; (vinyl) trimethyltin, (1-ethoxyvinyl) tributyltin, (2-furyl) tributyltin, Organotin compounds such as (2-thienyl) tributyltin; organoboron compounds such as phenylboronic acid; organosilicate compounds such as trimethylvinylsilicon-tris (dimethylamino) sulfonium difluorotrimethylsilicate; It can be potassium cyanide, and acetylene compounds such as trimethylsilylacetylene and phenylacetylene can also be used in the reaction in the presence of amines such as triethylamine in the same manner as the above organometallic compounds, and are preferably organotin compounds or organoboron compounds. .

  The amount of the organometallic compound used in the reaction is usually 0.5 to 10 mol, preferably 1 to 2 mol, relative to 1 mol of compound (Ik) or (XIX).

  The metal catalyst used in this step is not particularly limited as long as it is used for the cross coupling reaction, and is, for example, a nickel catalyst or a palladium catalyst.

  The amount of the metal catalyst used in the reaction is usually 0.0001 to 10 mol, preferably 0.01 to 0.5 mol, relative to 1 mol of compound (Ik) or (XIX).

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, water; alcohols such as methanol, ethanol, t-butanol; acetone, methyl isobutyl ketone Ketones such as acetonitrile; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; ethers such as diethyl ether, tetrahydrofuran and dioxane; Aromatic hydrocarbons; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; aliphatic hydrocarbons such as hexane and cyclohexane; organic amines such as triethylamine and pyridine; or these Mixing Agents and are obtained, preferably ethers, aromatic hydrocarbons or amides, more preferably ether, tetrahydrofuran, toluene or dimethylformamide.

  The reaction temperature mainly varies depending on the raw material compound, the reaction reagent, and the type of solvent used, but is usually −90 ° C. to 200 ° C., and preferably 0 ° C. to 130 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the type of solvent used, it is generally 5 minutes to 48 hours, preferably 15 minutes to 24 hours.

(Process L-2)
Step L-2 is a step of producing the compound (Ip) of the present invention by removing the protecting group for the hydroxyl group of the compound (XXIII).

  This step is the same as step A-4, B-5, C-4, D-2, E-3, F-2, G-2, J-6 or K-5.

  (Process M)

In the above formula, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X and Y are as defined above.

  Step M is represented by the present compound (Iq) or general formula (XXIV) by cyanating a 6-position unsubstituted pyridazine N-oxide derivative represented by general formula (Im) or (XXI). This is a step of producing a compound in which the hydroxyl group is protected, and further, a step of producing the compound (Ir) of the present invention by removing the protecting group of the compound (XXIV).

(Process M-1)
Step M-1 is represented by the present compound (Iq) or general formula (XXIV) by reacting compound (Im) or (XXI) with a cyanating agent in the presence or absence of a solvent. This is a process for producing a compound in which a hydroxyl group is protected.

  This step can be performed according to a known Reissert-Henze reaction (JOC, 48, 1983, 1375 to 1377; Heterocycles, 15, 1981, 981 to 984; Synthesis, 1983, 316 to 319, etc.).

(Process M-2)
Step M-2 is a step of producing the compound (Ir) of the present invention by removing the protecting group for the hydroxyl group of the compound (XXIV).

  This step is the same as steps A-4, B-5, C-4, D-2, E-3, F-2, G-2, J-6, K-5 or L-2.

  (Process N)

In the above formula, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X and Y are as defined above.

  In Step N, the 6-chloropyridazine derivative represented by the general formula (Ik) or (XIX) is dechlorinated to protect the hydroxyl group represented by the present compound (Is) or the general formula (XXV). This is a step for producing the compound (It) of the present invention by removing the protecting group of the compound (XXV).

(Process N-1)
In Step N-1, the compound (Ik) or (XIX) is reacted with a reducing agent in the presence or absence of a solvent to give a hydroxyl group represented by the present compound (Is) or the general formula (XXV). Is a process for producing a protected compound.

  This process can be performed according to process J-1 or K-2.

(Process N-2)
Step N-2 is a step of producing the compound (It) of the present invention by removing the protecting group for the hydroxyl group of the compound (XXV).

  This step is the same as step A-4, B-5, C-4, D-2, E-3, F-2, G-2, J-6, K-5, L-2 or M-2. It is.

  (Process O)

In the above formula, R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ and R ⁷ are as defined above.

  In Step O, the 3,4-dichloropyridazine derivative represented by the general formula (XXVI) is reacted with the catechol derivative represented by the general formula (XXVII), and then hydrolyzed to give the compound (Iu) of the present invention. It is a manufacturing process.

(Step O-1)
In Step O-1, compound (XXVI) is reacted with compound (XXVII) in the presence or absence of a solvent, and optionally in the presence of a base, to produce a condensed compound represented by general formula (XXVIII). It is a process.

  This step can be performed according to step A-1, B-2, D-1 or E-2, and the amount of the base used is usually 1 to 10 mol per 1 mol of compound (XXVI). Yes, preferably 2 to 6 mol.

(Process O-2)
Step O-2 is a step of producing the compound (Iu) of the present invention by hydrolyzing the compound (XXVIII).

  This step can be performed according to the case where Y is a hydrogen atom in Step A-3, B-4 or C-3, and the reaction temperature is preferably 80 ° C to 100 ° C.

  (Process P)

In the above formula, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X and Y are as defined above.

  In Step P, the 6-position of the 4,6-dichloropyridazine derivative represented by the general formula (Va) is selectively hydrolyzed to form a compound (XXIX), and then brominated at 4 and 6 positions with phosphorus oxybromide. Then, a process for producing a compound in which the hydroxyl group represented by the compound (Iv) or the general formula (XXXI) of the present invention is protected by selectively reacting an oxygen nucleophile at the 4-position, XXXI) is a process for producing the compound (Iw) of the present invention by removing the protecting group.

(Process P-1)
In Step P-1, the compound (Va) is hydrolyzed in the presence or absence of a solvent in the presence of an acid to selectively convert the 6-position chlorine atom to a hydroxyl group, and is represented by the general formula (XXIX). This is a process for producing a compound to be produced.

  The acid used is not particularly limited as long as it is an acid having a pH of 6 or less. For example, organic acids such as formic acid, acetic acid, succinic acid, propionic acid, succinic acid, maleic acid, fumaric acid, benzoic acid; hydrogen fluoride; Mineral acids such as acids, hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid; or Lewis acids such as aluminum chloride, iron chloride, titanium chloride, boron trifluoride, etc. Preferred are organic acids, and more preferred are formic acid or acetic acid.

  This step is preferably performed in the presence of an acid metal salt.

  The metal salt of the acid used is, for example, an alkali metal salt of an organic acid such as sodium formate, potassium formate, lithium acetate, sodium acetate, potassium acetate, cesium acetate, sodium benzoate; magnesium formate, calcium formate, magnesium acetate, Alkaline earth metal salts of organic acids such as calcium acetate and magnesium benzoate; Alkali metal salts or alkaline earth metal salts of carbonic acid such as sodium carbonate, potassium carbonate, calcium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; Sodium fluoride, potassium fluoride, sodium chloride, potassium chloride, sodium bromide, potassium bromide, sodium iodide, potassium iodide, sodium sulfate, sodium hydrogen sulfate, potassium sulfate, potassium hydrogen sulfate, magnesium sulfate, sodium phosphate, Binatto hydrogen phosphate Or alkali metal salts of mineral acids such as sodium dihydrogen phosphate, potassium phosphate, dipotassium hydrogen phosphate, potassium dihydrogen phosphate, etc., preferably alkali metals of organic acids A salt, more preferably sodium formate, potassium formate, sodium acetate or potassium acetate.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, water; alcohols such as methanol, ethanol, t-butanol; acetone, methyl isobutyl ketone Ketones such as acetonitrile; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; ethers such as diethyl ether, tetrahydrofuran and dioxane; Aromatic hydrocarbons; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethylsulfoxide; organic acids such as formic acid, acetic acid and propionic acid; or a mixed solvent thereof, preferably , Water, nitriles, ethers, amino S, a sulfoxide or an organic acid, more preferably water, acetonitrile, tetrahydrofuran, dioxane, dimethylformamide, dimethyl sulfoxide, formic acid or acetic acid.

  The reaction temperature varies depending on the raw material compound, the reaction reagent, and the type of solvent used, but is usually -90 ° C to 200 ° C, and preferably 0 ° C to 150 ° C.

  The reaction time mainly varies depending on the reaction temperature, the raw material compound, the reaction reagent, and the type of solvent used, but is usually 5 minutes to 24 hours, and preferably 15 minutes to 12 hours.

(Process P-2)
Step P-2 is a step of producing compound (XXX) by reacting compound (XXIX) with phosphorus oxybromide in the presence or absence of a solvent.

  The amount of phosphorus oxybromide used in this step is usually 0.5 to 100 mol, preferably 1 to 10 mol, relative to 1 mol of compound (XXIX).

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, ketones such as acetone and methyl isobutyl ketone; nitriles such as acetonitrile; ethyl acetate Esters such as; Halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; Ethers such as diethyl ether, tetrahydrofuran and dioxane; Aromatic hydrocarbons such as toluene; Dimethylformamide and dimethylacetamide Amides; Sulfoxides such as dimethyl sulfoxide; Aliphatic hydrocarbons such as hexane and cyclohexane; or a mixed solvent thereof, preferably halogenated hydrocarbons, and more preferably Methylene chloride and chloroform.

  While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally -90 ° C to 200 ° C, preferably 0 ° C to 100 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the kind of solvent used, it is generally 5 minutes to 72 hours, preferably 30 minutes to 24 hours.

(Process P-3)
In Step P-3, the compound (XXX) is reacted with an oxygen nucleophile represented by the general formula (VI) in the presence or absence of a solvent, and optionally in the presence of a base, to give a compound of the present invention ( Iv) or a process for producing a compound in which a hydroxyl group represented by formula (XXXI) is protected.

  This step is the same as step A-3, B-4, C-3 or J-5.

(Process P-4)
Step P-4 is a step of producing the compound (Iw) of the present invention by removing the protecting group for the hydroxyl group of the compound (XXXI).

  This step is a step A-4, B-5, C-4, D-2, E-3, F-2, G-2, J-6, K-5, L-2, M-2 or N -2.

  (Process Q)

In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are as defined above. The compound represented by the general formula (XXXII) represents an oxygen nucleophile, a sulfur nucleophile, and a nitrogen nucleophile. Z is a substituent obtained by removing a proton from an oxygen nucleophile, sulfur nucleophile or nitrogen nucleophile, and may be, for example, an alkoxy group, a thioalkoxy group, a dialkylamino group, or the like.

  Step Q is a step of converting the hydroxy compound of the present invention represented by the general formula (Ib) into the ester derivative of the present invention represented by the general formula (Iy).

(Process Q-1)
Step Q-1 is a step of producing the compound (Ix) of the present invention by reacting the compound (Ib) of the present invention with phosgene in the presence or absence of a solvent.

  The amount of phosgene used in the reaction is usually 0.5 to 10 mol, preferably 1 to 3 mol, relative to 1 mol of compound (Ib).

  The reaction is preferably carried out in the presence of a base.

  The base used is not particularly limited as long as it usually shows a pH of 8 or more. For example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkalis such as sodium carbonate, potassium carbonate and cesium carbonate Metal carbonates; metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; aliphatic triions such as triethylamine, tributylamine and diisopropylethylamine Tertiary amines; aliphatic cyclic tertiary amines such as 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) Of pyridine, collidine, 4- (N, N-dimethylamino) pyridine Or an organometallic base such as n-butyllithium, sec-butyllithium, lithium diisopropylamide, sodium bis (trimethylsilyl) amide, lithium bis (trimethylsilyl) amide, and preferably an alkali metal Hydroxides, alkali metal carbonates, aliphatic tertiary amines, aliphatic cyclic tertiary amines or pyridines, more preferably sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate , Triethylamine, 1,4-diazabicyclo [2.2.2] octane (DABCO), pyridine or 4- (N, N-dimethylamino) pyridine.

  The amount of the base used for the reaction is usually 0.5 to 20 mol, preferably 1 to 5 mol, relative to 1 mol of compound (Ib).

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, water; ketones such as acetone and methyl isobutyl ketone; nitriles such as acetonitrile; acetic acid Esters such as ethyl; Halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; Ethers such as diethyl ether, tetrahydrofuran and dioxane; Aromatic hydrocarbons such as toluene; Hexane and cyclohexane Aliphatic hydrocarbons; Amides such as dimethylformamide and dimethylacetamide; Sulfoxides such as dimethylsulfoxide; or a mixed solvent thereof, preferably nitriles, halogenated hydrocarbons, ethers, Water-ester mixed solvent, water-halogenated Hydrogenated mixed solvent, water-ether mixed solvent, water-aromatic hydrocarbon mixed solvent or water-aliphatic hydrocarbon mixed solvent, more preferably acetonitrile, methylene chloride or water-toluene mixed solvent It is.

  The reaction temperature mainly varies depending on the raw material compound, the reaction reagent, and the type of solvent used, but is usually −90 ° C. to 200 ° C., and preferably 0 ° C. to 100 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the type of solvent used, it is usually 5 minutes to 48 hours, preferably 15 minutes to 12 hours.

(Process Q-2)
Step Q-2 comprises reacting the compound (Ix) of the present invention with a nucleophile represented by the general formula (XXXII) in the presence or absence of a solvent, and optionally in the presence of a base. This is a process for producing the inventive compound (Iy).

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, water; ketones such as acetone and methyl isobutyl ketone; nitriles such as acetonitrile; acetic acid Esters such as ethyl; Halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; Ethers such as diethyl ether, tetrahydrofuran and dioxane; Aromatic hydrocarbons such as toluene; Hexane and cyclohexane Aliphatic hydrocarbons; Amides such as dimethylformamide and dimethylacetamide; Sulfoxides such as dimethylsulfoxide; or a mixed solvent thereof, preferably nitriles, halogenated hydrocarbons, ethers, Water-ester mixed solvent, water-halogenated Hydrogenated mixed solvent, water-ether mixed solvent, water-aromatic hydrocarbon mixed solvent or water-aliphatic hydrocarbon mixed solvent, more preferably acetonitrile, methylene chloride or water-toluene mixed solvent It is.

  The base used is not particularly limited as long as it usually shows a pH of 8 or more. For example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkalis such as sodium carbonate, potassium carbonate and cesium carbonate Metal carbonates; metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; aliphatic triions such as triethylamine, tributylamine and diisopropylethylamine Tertiary amines; aliphatic cyclic tertiary amines such as 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) Of pyridine, collidine, 4- (N, N-dimethylamino) pyridine Or an organometallic base such as n-butyllithium, sec-butyllithium, lithium diisopropylamide, sodium bis (trimethylsilyl) amide, lithium bis (trimethylsilyl) amide, and preferably an alkali metal Hydroxides, alkali metal carbonates, aliphatic tertiary amines, aliphatic cyclic tertiary amines or pyridines, more preferably sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate , Triethylamine, 1,4-diazabicyclo [2.2.2] octane (DABCO), pyridine or 4- (N, N-dimethylamino) pyridine.

  The amount of the base used for the reaction is usually 0.5 to 20 mol, and preferably 1 to 5 mol with respect to 1 mol of compound (Ix).

  The nucleophile (XXXII) used in the reaction is not particularly limited as long as it replaces the chlorine atom of the chlorocarbonate (Ix), but examples of the oxygen nucleophile include methanol, ethanol and propanol. Or alcohols such as phenol and 4-chlorophenol, and examples of sulfur nucleophiles include thiols such as methanethiol, ethanethiol and propanethiol; The nitrogen nucleophile can be, for example, methylamine, dimethylamine, diethylamine, methyl (t-butyl) amine, methyl (cyanomethyl) amine, methyl (ethoxycarbonylmethyl). Amine, bis (cyanomethyl) amine, bis (2-cyanoethyl) a Aliphatic chain such as bis (ethoxycarbonylmethyl) amine, bis (2-methoxyethyl) amine, bis (2-ethoxyethyl) amine, bis (2-chloroethyl) amine, N, O-dimethylhydroxylamine Amines; aromatic amines such as methyl (phenyl) amine, methyl (pyridyl) amine; aziridine, azetidine, pyrrolidine, piperidine, morpholine, thiomorpholine, N-methylpiperazine, N-phenylpiperazine, 2-methoxycarbonylpyrrolidine 3-hydroxypyrrolidine, 4-bromopiperidine, 4-methylpiperidine, 2,2,6,6-tetramethylpiperidine, 2-ethoxycarbonylpiperidine, 4-ethoxycarbonylpiperidine, 2,6-dimethylmorpholine, 1,2 , 3,4-Tetra Aliphatic cyclic amines such as droisoquinoline and 1,3-oxazolidine; aromatic cyclic amines such as carbazole and 2,5-dimethylpyrrole, preferably methanol, ethanol, methanethiol, ethanethiol, Methylamine, dimethylamine, methyl (cyanomethyl) amine, methyl (ethoxycarbonylmethyl) amine, bis (cyanomethyl) amine, bis (2-cyanoethyl) amine, bis (ethoxycarbonylmethyl) amine, bis (2-methoxyethyl) amine Bis (2-ethoxyethyl) amine, bis (2-chloroethyl) amine, N, O-dimethylhydroxylamine, methyl (pyridyl) amine, azetidine, pyrrolidine, piperidine, morpholine, thiomorpholine, N-methylpiperazine, 2- Metoki Cicarbonylpyrrolidine, 3-hydroxypyrrolidine, 2-ethoxycarbonylpiperidine, 4-ethoxycarbonylpiperidine, 2,6-dimethylmorpholine, 1,3-oxazolidine, 2,5-dimethylpyrrole, more preferably dimethylamine , Methyl (cyanomethyl) amine, methyl (ethoxycarbonylmethyl) amine, bis (cyanomethyl) amine, bis (ethoxycarbonylmethyl) amine, bis (2-methoxyethyl) amine, bis (2-ethoxyethyl) amine, N, O -Dimethylhydroxylamine, azetidine, morpholine, thiomorpholine, N-methylpiperazine, 2-methoxycarbonylpyrrolidine, 3-hydroxypyrrolidine, 2-ethoxycarbonylpiperidine, 4-ethoxycarbonylpiperidine, , 6-dimethyl-morpholine.

  The amount of the nucleophile used for the reaction is usually 0.5 to 20 mol, preferably 1 to 5 mol, relative to 1 mol of compound (Ix).

  The reaction temperature mainly varies depending on the raw material compound, the reaction reagent, and the type of solvent used, but is usually −90 ° C. to 200 ° C., and preferably 0 ° C. to 100 ° C.

  While the reaction time mainly varies depending on the reaction temperature, raw material compound, reaction reagent and the type of solvent used, it is usually 5 minutes to 48 hours, preferably 15 minutes to 12 hours.

Note that after the completion of each reaction step, prior to the subsequent step, functional groups in R ¹ to R ⁷ of the target compound of each step, as long as it is within the scope of the definition of R ¹ to R ^7, according to a conventional method Functional group conversion is possible.

In Steps A-1, B-2, D-1 and E-2, when at least one of R ¹ and R ² is a chlorine atom, depending on the reaction conditions, R ¹ or R ² Of chlorine atom

Further, in Steps A-3, B-4, C-3 and J-5, when at least one of R ¹ and R ² is a chlorine atom, depending on the reaction conditions, In the process, the chlorine atom of R ¹ or R ² may be substituted by the group OY. Furthermore, in process P-3, when the bromine atom at the 6-position of the pyridazine ring or R ² is a chlorine atom, , R ² chlorine atom may be replaced by the group OY.

  The starting compounds (II) of steps A and B are either commercially available or, for example, Industrial Chemical Journal, 1971, 74, 7, 1490-1491; Tetrahedron, 1999 55, 52, 15067-15070; The Journal of Organic Chemistry, 1963, 28, 218-221, or according to these methods.

  Starting compounds (X) of steps D and E are, for example, Helvetica Chimica Acta, 1956, 39, 1755-1664; Monatshefte fur Chemie, 1968, 99, 15 -81 (in this description the letter u in Monatshefte fur Chemie represents u-umlaut); German Patent 1,912,472, filed November 12, 1970 (filed April 12, 1969) (Ger.Offen. 1,912,472 , 12 Nov 1970, Appl. 12 Mar 1969).

  As the phenol compound (III) used in Steps A, B, D and E, a commercially available product can be used, or it can be produced using a known method or according to a known method.

  2-isobutylphenol can be produced, for example, by the method described in Canadian Journal of Chemistry, 1956, 34, 851-854.

  2-pentylphenol can be produced, for example, by the method described in Tetrahedron Letters, 1989, Vol. 30, No. 35, pages 4741-4744.

  2-hexylphenol, for example, from the commercially available 1-methoxy-2-vinylbenzene, Journal of the Chemical Society: Parkin Transaction I (Journal of the Chemical Society: Parkin transaction I), 2000, vol. 7, pp. 1109-1116 (conversion of vinyl group to hexyl group) and Journal of Medicinal Chemistry, 1977, vol. 20, 10 No., pages 1317-1323 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-cyclopropylphenol can be produced, for example, by the method described in Bioorganic & Medicinal Chemistry, 1997, Vol. 5, No. 10, pp. 1959-1968.

  2- (1-methylcyclopropyl) phenol (2- (1-methylcyclopropyl) phenol) is, for example, from the commercially available 1- (2-methoxyphenyl) ethanone, the Journal of The method described in The Journal of Organic Chemistry, 1963, 28, 1128 or Synthetic Communications, 1985, 15, 10, 855-864 (conversion of carbonyl groups to olefins) Conversion, Wittg reaction) and Organic Reactions, 1973, 20, 1-131 or Journal of the American Chemical Society, 1975, 97, 3428 or Tetrahedron Letters, 1998, Vol. 39, pages 8621-8624 (construction of cyclopropyl groups, Simmons-Smith reaction), and biotechnology Science Biotechnology and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (Conversion of phenylmethyl ether to phenol, demethylation) Can be produced according to the following reaction.

  2- (1-ethylcyclopropyl) phenol is a commercially available 1- (2-methoxyphenyl) -1-propanone, for example. ) From The Journal of Organic Chemistry, 1963, 28, 1128 or Synthetic Communications, 1985, 15, 10, 855-864 ( (Conversion of carbonyl group to olefin, Wittg reaction) and Organic Reactions, 1973, 20, 1-131 or Journal of the American Chemical Society, 1975, 97, page 3428 or Tetrahedron Letters, 1998, 39, pages 8621-8624 (construction of cyclopropyl group, Simmons-Smith reaction), and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pp. 1572-1574 or JP-A-11-322755 (conversion, removal of phenylmethyl ether to phenol (Methylation reaction).

  2- (1-cyclopropylcyclopropyl) phenol is a commercially available 2,3-dihydro-4H-chromen-4-one (2,3-dihydro-4H-chromen), for example. -4-one), Journal of the Chemical Society: Parkin transaction I, 1990, pages 689-693, cyclopropyl (2-hydroxyphenyl) Methanone [cyclopropyl (2-hydroxyphenyl) methanone], Organic Synthesis, Collective Volume, Volume 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation) Reaction) and The Journal of Organic Chemistry, 1963, 28, 1128 or synthetic communication (Synthetic Communications), 1985, Vol. 15, No. 10, pages 855-864 (conversion of carbonyl group to olefin, Wittg reaction), Organic Reactions, 1973, Vol. 20, 1-131 or Journal of the American Chemical Society, 1975, 97, 3428 or Tetrahedron Letters, 1998, 39, 8621-8624 Methods (construction of cyclopropyl groups, Simmons-Smith reaction), and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11- It can be produced according to the method described in 322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  1- (2-hydroxyphenyl) cyclopropanecarbonitrile (Journal of the American Chemical Society), 2000, Vol. 122, No. 4, 1- (2-methoxyphenyl) cyclopropanecarbonitrile (1- (2-methoxyphenyl) cyclopropanecarbonitrile) is produced by the method described on pages 712-713, and organic synthesis, collective volume, Volume 5, pages 412-414, can be produced according to the method described in the above (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2- (1-phenylcyclopropyl) phenol is a commercially available 1- (2-methoxyphenyl) (phenyl) methanone, for example. ) From The Journal of Organic Chemistry, 1963, 28, 1128 or Synthetic Communications, 1985, 15, 10, 855-864 ( (Conversion of carbonyl group to olefin, Wittg reaction) and Organic Reactions, 1973, 20, 1-131 or Journal of the American Chemical Society, 1975, 97, 3428 or Tetrahedron Letters, 1998, 39, 8621-8624 (construction of cyclopropyl group, Simmons-Smith reaction) ), And the method described in Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP 11-322755 (to the phenol of phenyl methyl ether) Conversion, demethylation reaction).

  2- (2-methylcyclopropyl) phenol (2- (2-methylcyclopropyl) phenol) is, for example, from commercially available 1- (chloromethyl) -2-methoxybenzene, Journal of the American Chemical Society, 1973, Vol. 95, No. 2, pp. 581-582 (construction of cyclopropyl group) and bioscience Biotechnology and Biochemistry (Bioscience) , Biotechnology, and Biochemistry), 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction) .

  2- (2,2-dimethylcyclopropyl) phenol is, for example, commercially available 1- (chloromethyl) -2-methoxybenzene [1- (chloromethyl) -2- methoxybenzene], Journal of the American Chemical Society, 1973, Vol. 95, No. 2, pages 581-582 (construction of cyclopropyl group), bioscience biotechnology and Biochemistry (Bioscience, Biotechnology, and Biochemistry), 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction) It can be manufactured similarly.

  2-[(cis-2, cis-3-dimethyl) -ref-1-cyclopropyl] phenol (2-[(cis-2, cis-3-dimethyl) -ref-1-cyclopropyl] phenol) is, for example, From the commercial 1- (chloromethyl) -2-methoxybenzene, Journal of the American Chemical Society, 1973, volume 95, No. 2 581-582 (construction of cyclopropyl group) and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or It can be produced according to the method described in 11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-[(cis-2, trans-3-dimethyl) -ref-1-cyclopropyl] phenol (2-[(cis-2, trans-3-dimethyl) -ref-1-cyclopropyl] phenol) is, for example, From the commercial 1- (chloromethyl) -2-methoxybenzene, Journal of the American Chemical Society, 1973, volume 95, No. 2 581-582 (construction of cyclopropyl group) and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or It can be produced according to the method described in 11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-[(trans-2, trans-3-dimethyl) -ref-1-cyclopropyl] phenol (2-[(trans-2, trans-3-dimethyl) -ref-1-cyclopropyl] phenol) From the commercial 1- (chloromethyl) -2-methoxybenzene, Journal of the American Chemical Society, 1973, volume 95, No. 2 581-582 (construction of cyclopropyl group) and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or It can be produced according to the method described in 11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-[(ref-1, cis-5, cis-6) -bicyclo [3.1.0] hexa-6-yl] phenol (2-[(ref-1, cis-5, cis-6) -bicyclo [ 3.1.0] hex-6-yl] phenol), for example, from the commercial 1- (chloromethyl) -2-methoxybenzene, Journal of the American Chemical Society (Journal of the American Chemical Society), 1973, Vol. 95, No. 2, pages 581-582 (construction of cyclopropyl groups), and Bioscience, Biotechnology, and Biochemistry, 1993 No. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-[(ref-1, cis-5, trans-6) -bicyclo [3.1.0] hex-6-yl] phenol (2-[(ref-1, cis-5, trans-6) -bicyclo [ 3.1.0] hex-6-yl] phenol), for example, from the commercial 1- (chloromethyl) -2-methoxybenzene, Journal of the American Chemical Society (Journal of the American Chemical Society), 1973, Vol. 95, No. 2, pages 581-582 (construction of cyclopropyl groups), and Bioscience, Biotechnology, and Biochemistry, 1993 No. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-[(ref-1, cis-6, cis-7) -bicyclo [4.1.0] hept-7-yl] phenol {2-[(ref-1, cis-6, cis-7) -bicyclo [ 4.1.0] hept-7-yl] phenol} is, for example, from the commercially available 1- (chloromethyl) -2-methoxybenzene, Journal of the American Chemical Society (Journal of the American Chemical Society), 1973, Vol. 95, No. 2, pages 581-582 (construction of cyclopropyl groups), and Bioscience, Biotechnology, and Biochemistry, 1993 No. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-[(ref-1, cis-6, trans-7) -bicyclo [4.1.0] hept-7-yl] phenol (2-[(ref-1, cis-6, trans-7) -bicyclo [ 4.1.0] hept-7-yl] phenol), for example, from the commercially available 1- (chloromethyl) -2-methoxybenzene, Journal of the American Chemical Society (Journal of the American Chemical Society), 1973, Vol. 95, No. 2, pages 581-582 (construction of cyclopropyl groups), and Bioscience, Biotechnology, and Biochemistry, 1993 No. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-[(2,2, cis-3-trimethyl) -ref-1-cyclopropyl] phenol (2-[(2,2, cis-3-trimethyl) -ref-1-cyclopropyl] phenol) is, for example, From the commercial 1- (chloromethyl) -2-methoxybenzene, Journal of the American Chemical Society, 1973, volume 95, No. 2 581-582 (construction of cyclopropyl group) and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or It can be produced according to the method described in 11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-[(2,2, trans-3-trimethyl) -ref-1-cyclopropyl] phenol (2-[(2,2, trans-3-trimethyl) -ref-1cyclopropyl] phenol) is commercially available, for example. From 1- (chloromethyl) -2-methoxybenzene, Journal of the American Chemical Society, 1973, Vol. 95, No. 2, 581 -582 (construction of cyclopropyl group) and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11- It can be produced according to the method described in 322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-cyclobutylphenol can be produced, for example, by the method described in German Patent DE-2825388.

  1- (2-hydroxyphenyl) cyclobutanecarbonitrile (1- (2-hydroxyphenyl) cyclobutanecarbonitrile) is, for example, Pharmaceutical Chemistry Journal (English Translation), 1980, Volume 14 , No. 2, pages 114-118.

  1- (2-Hydroxyphenyl) cyclobutanecarboxylic acid (1- (2-hydroxyphenyl) cyclobutanecarboxylic acid) is, for example, Pharmaceutical Chemistry Journal (English Translation), 1980, 14 and No. 2, pages 114-118.

  2- (1-propynyl) phenol is, for example, Journal of the Chemical Society: Parkin transaction I, 1998, pages 477-484. It can manufacture by the method of description.

  2- (cyclopropylmethyl) phenol is a commercially available 2,3-dihydro-4H-chromen-4-one, for example. From the Journal of the Chemical Society: Parkin transaction I, 1990, pages 689-693, cyclopropyl (2-hydroxyphenyl) methanone (cyclopropyl (2- from hydroxyphenyl) methanone) according to the method described in Organic Reactions, 1941, Vol. 1, p. 155 (Clemmensen reduction).

  2- (methoxymethyl) phenol can be produced, for example, by the method described in Tetrahedron Letters, 1999, 40, 6049.

  2- (ethoxymethyl) phenol can be produced, for example, by the method described in Tetrahedron Letters, 1999, 40, 6049.

  2- (1,3-dioxolan-2-yl) phenol is, for example, Tetrahedron Letters, 1989, volume 30, 13 No., pages 1609-1612.

  1- (2-hydroxyphenyl) ethanone O-methyloxime is an example of commercially available 1- (2-hydroxyphenyl) ethanone (1- (2-hydroxyphenyl) ethanone). ) According to the method described in Journal of the American Chemical Society, 1986, Vol. 108, pages 6016-6023.

  3 '-(trifluoromethyl) [1,1'-biphenyl] -2-ol (3'-(trifluoromethyl) [1,1'-biphenyl] -2-ol) is an example of commercially available 2-iodophenol. From (2-iodophenol) and 3- (trifluoromethyl) phenylboronic acid, the method described in Chemical Reviews, 1995, Vol. 95, pages 2457-2483 (phenylation) Reaction, Suzuki-Miyaura coupling reaction).

  2- (1H-pyrrol-1-yl) phenol is, for example, The Journal of Antibiotics, 1994, 47, 5 No., pages 602-605.

  2- (2-thienyl) phenol can be obtained, for example, by the method described in Journal of Heterocyclic Chemistry, 1985, Vol. 22, pages 1667-1669. Can be manufactured.

  2- (3-thienyl) phenol can be obtained, for example, by the method described in Journal of Heterocyclic Chemistry, 1985, Vol. 22, pages 1667-1669. Can be manufactured.

  2- (1H-pyrazol-1-yl) phenol is, for example, Canadian Journal of Chemistry, 1963, 41, 2086-2092. It can be produced by the method described on the page.

  2- (3,5-dimethyl-1H-pyrazol-1-yl) phenol (2- (3,5-dimethyl-1H-pyrazol-1-yl) phenol) is described, for example, in Heterocycles, 1982 19th volume, No. 8, 1487-1495.

  2- [3- (trifluoromethyl) -1H-pyrazol-1-yl] phenol (2- [3- (trifluoromethyl) -1H-pyrazol-1-yl] phenol) is, for example, commercially available 1- (2 1- (2-methoxyphenyl) hydrazine hydrochloride (1- (2-methoxyphenyl) hydrazine hydrochloride), according to the method described in Journal of Fluorine Chemistry 1998, Vol. 92, p.23. ) -3- (Trifluoromethyl) -1H-pyrazole (1- (2-methoxyphenyl) -3- (trifluoromethyl) -1H-pyrazole), organic synthesis, collective volume, Volume 5, pages 412-414, can be produced according to the method described above (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2- [4- (trifluoromethyl) -1H-pyrazol-1-yl] phenol (2- [4- (trifluoromethyl) -1H-pyrazol-1-yl] phenol) is, for example, commercially available 1- (2 -Methoxyphenyl) hydrazine hydrochloride (1- (2-methoxyphenyl) hydrazine hydrochloride) was prepared according to the method described in Tetrahedron Letters, 1996, Vol. 37, No. 11, page 1829. Methoxyphenyl) -4- (trifluoromethyl) -1H-pyrazole (1- (2-methoxyphenyl) -4- (trifluoromethyl) -1H-pyrazole) is manufactured, Organic Synthesis, Collective Volume ), Vol. 5, pages 412-414 (conversion to phenylmethyl ether to phenol, demethylation reaction).

  2- [5- (trifluoromethyl) -1H-pyrazol-1-yl] phenol (2- [5- (trifluoromethyl) -1H-pyrazol-1-yl] phenol) is, for example, commercially available 1- (2 1- (2-methoxyphenyl) hydrazine hydrochloride (1- (2-methoxyphenyl) hydrazine hydrochloride) according to the method described in Journal of Fluorine Chemistry 1998, Vol. 92, p.23. ) -5- (Trifluoromethyl) -1H-pyrazole (1- (2-methoxyphenyl) -5- (trifluoromethyl) -1H-pyrazole), Organic Synthesis, Collective Volume, Volume 5, pages 412-414, can be produced according to the method described above (conversion of phenylmethyl ether to phenol, demethylation reaction).

  5- (2-hydroxyphenyl) -N, N-dimethyl-1H-pyrazole-1-sulfonamide (5- (2-hydroxyphenyl) -N, N-dimethyl-1H-pyrazole-1-sulfonamide) is, for example, From commercially available 4-chloro-2- (1H-pyrazol-5-yl) phenol, Journal of Medicinal Chemistry, 1998 5- (5-Chloro-2-hydroxyphenyl) -N, N-dimethyl-1H-pyrazole-1-sulfonamide (5), which can be produced according to the method described in Y. 41, No. 12, 2019-2028 -(5-chloro-2-hydroxyphenyl) -N, N-dimethyl-1H-pyrazole-1-sulfonamide), according to the method described in Experimental Chemistry Course 4th edition Volume 26 pages 251-266 (catalytic hydrogenation reaction) Can be manufactured.

  3- (2-hydroxyphenyl) -N, N-dimethyl-1H-pyrazole-1-sulfonamide (3- (2-hydroxyphenyl) -N, N-dimethyl-1H-pyrazole-1-sulfonamide) is, for example, From commercially available 4-chloro-2- (1H-pyrazol-5-yl) phenol, Journal of Medicinal Chemistry, 1998 3- (5-Chloro-2-hydroxyphenyl) -N, N-dimethyl-1H-pyrazole-1-sulfonamide (3), which can be produced according to the method described in Y. 41, No. 12, 2019-2028 -(5-chloro-2-hydroxyphenyl) -N, N-dimethyl-1H-pyrazole-1-sulfonamide), according to the method described in Experimental Chemistry Course 4th edition Volume 26 pages 251-266 (catalytic hydrogenation reaction) Can be manufactured.

  2- (4-methyl-1,3-thiazol-2-yl) phenol (2- (4-methyl-1,3-thiazol-2-yl) phenol) is, for example, commercially available 2-hydroxybenzonitrile ( Prepared from 2-hydroxybenzonitrile by the method described in JP-A-11-60552 (thioamidation reaction of cyano group) and the method described by Liebigs Annalen der Chemie, 1890, 259, 236 it can.

  2- (1,3-benzoxazol-2-yl) phenol is an example of The Journal of Organic Chemistry, 1970. 35, pages 3147-3149.

  2- (1,3-benzothiazol-2-yl) phenol is, for example, the Journal of Organic Chemistry, 1970 35, pages 3147-3149.

  2- (dimethylamino) phenol can be produced, for example, by the method described in Journal of Medicinal Chemistry, 1998, Vol. 41, pages 4800-4818.

  2- (2-methoxyethoxy) phenol (Journal of the Chemical Society: Parkin transaction, for example, from the commercially available pyrocatechol, Journal of the Chemical Society) I), 1980, can be produced according to the method described on pages 756-758.

  2- (isopropylsulfanyl) phenol can be produced, for example, by the method described in Tetrahedron, 1970, Vol. 26, pages 4449-4471.

  3-cyclopropylphenol is, for example, from commercially available 1-bromo-3-methoxybenzene, Tetrahedron Letters, 2000, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction) and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, 1572 -1574 or according to the method described in JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  3- (2-furyl) phenol is described in, for example, The Journal of Organic Chemistry, 1993, Vol. 58, No. 17, pages 4722-4726. 2- (3-methoxyphenyl) furan (Bioscience, Biotechnology, and Biochemistry), 1993, Vol. 57, 9 No., pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  4-cyclopropylphenol is, for example, from commercially available 1-bromo-4-methoxybenzene, Tetrahedron Letters, 2000, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction) and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, 1572 -1574 or according to the method described in JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-Bromo-3-methylphenol is an organic synthesis or collective from commercially available 2-methoxy-6-methylaniline, for example. The method described in Collective Volume, Volume 3, pages 185-187, or The Journal of Organic Chemistry, 1977, Volume 42, pages 242-2430. Conversion to benzene, Sandmeyer reaction, etc.) and the method described in Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 It can be produced according to (conversion of phenylmethyl ether to phenol, demethylation reaction).

  3-Fluoro-2-methylphenol is a commercially available 3-fluoro-2-methylbenzaldehyde from Journal of the Chemical Society: Parkin Transaction I ( It can be produced according to the method described in Journal of the Chemical Society: Parkin transaction I), 1974, page 1353.

  3-chloro-2-methylphenol is more organic than organic 1-chloro-3-methoxy-2-methylbenzene. Synthesis, Collective Volume, Vol. 5, pages 412-414 (conversion to phenylmethyl ether to phenol, demethylation reaction).

  3-methoxy-2-methylphenol is organic synthesis from commercially available 2-methyl-1,3-benzenediol (Organic Synthesis), It can be produced according to the method described in Collective Volume, Vol. 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation reaction).

  2-cyclopropyl-3-methylphenol is, for example, from commercially available 2-methoxy-6-methylaniline, organic synthesis, Collective Volume, Volume 3, pages 185-187, or The Journal of Organic Chemistry, 1977, Volume 42, pages 242-2430. Conversion to bromobenzene, Sandmeyer reaction, etc.) and the method described in Tetrahedron Letters, 1979, 20, 4159-4162, or Tetrahedron, 1997, 53, 43 No. 14599-14614 or the method described in Bulletin of the Chemical Society of Japan, 1971, vol. 44, pages 2237-2248 Conversion reaction of aromatic bromide to aromatic aldehyde), and The Journal of Organic Chemistry, 1963, 28, 1128 or Synthetic Communications, 1985, 15, No. 10, pages 855-864 (Conversion of carbonyl group to olefin, Wittg reaction) and Organic Reactions, 1973, 20, pp. 1-131 or Journal of the American Chemical Society (Journal of the American Chemical Society), 1975, 97, 3428 or Tetrahedron Letters, 1998, 39, 8621-8624 (construction of cyclopropyl group, Simmons-Smith Reaction) and Bioscience, Biotechnology, and Bioche mistry), 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-cyclopropyl-3-methoxyphenol is, for example, from the commercially available 2,6-dimethoxybenzaldehyde, the Journal of Organic Chemistry. ), 1963, 28, 1128 or Synthetic Communications, 1985, 15, 10, 855-864 (conversion of carbonyl group to olefin, Wittg reaction), and Organic Reactions, 1973, 20, 1-131 or Journal of the American Chemical Society, 1975, 97, 3428 or Tetrahedron Letters 1998, 39, 8621-8624 (construction of cyclopropyl group, Simmons-Smith reaction), and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pp. 1572-1574 or Japanese Patent Application Laid-Open No. 11-322755 (Methylation reaction).

  4-indanol is, for example, a method described in Organic Reactions, 1941, Vol. 1, page 155 from commercially available 4-hydroxy-1-indanone. It can be produced according to (Clemmensen reduction).

  3-methyl-4-indanol can be produced, for example, by the method described in Journal of Applied Chemistry, 1959, Vol. 9, pages 629,637.

  1-methyl-4-indanol can be produced, for example, by the method described in Journal of the Chemical Society, 1961, pages 2773-2777.

  2,2-dimethyl-4-indanol is described in, for example, Journal of Chemical Research Miniprint, 1985, Vol. 8, pages 2724-2747 It can manufacture by the method of.

  Spiro [cyclopropane-1,3 '-(2', 3'-dihydro-1'H-indene-4'-ol)] (spiro [cyclopropane-1,3 '-(2', 3'-dihydro- 1'H-inden-4'-ol)]), for example, from the commercially available 2,3-dihydro-4H-chromen-4-ol, Organic and Medicinal Chemistry, 1999, Vol. 7, No. 12, pp. 2801-2810 (synthesis of 7-hydroxy-1-indanone), and Organic Synthesis, Collective Volume, Volume 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation), and Journal of Organic Chemistry (The Journal of Organic Chemistry), 1963, 28, 1128, or Synthetic Communications, 1985 Vol. 15, No. 10, pages 855-864 (Conversion of carbonyl group to olefin, Wittg reaction) and Organic Reactions, 1973, 20, 1-131 or Journal of the American Chemical Society, 1975, 97, 3428 or Tetrahedron Letters, 1998, 39, 8621-8624 (construction of cyclopropyl group, Simmons-Smith reaction) and the method described in Bioscience, Biotechnology, and Biochemistry (Bioscience, Biotechnology, and Biochemistry), 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 It can be produced according to the conversion of ether to phenol, demethylation reaction).

  7-hydroxy-2,3-dihydro-1H-inden-1-one O-methyloxime is, for example, commercially available 2 , 3-Dihydro-4H-chromen-4-ol (Bioorganic and Medicinal Chemistry), 1999, Vol. 7, No. 12, 2801-2810 (7-hydroxy-1-indanone synthesis), Organic Synthesis, Collective Volume Vol. 4, 836- 838 (conversion of phenol to phenyl methyl ether, methylation reaction) and Chemical Pharmaceutical Bulletin, 1988, Vol. 36, No. 8, pages 3134-3137 Method (conversion of carbonyl group to oxime) and bioscience The method described in IoTechnology and Biochemistry (Bioscience, Biotechnology, and Biochemistry), 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 It can be produced according to (Reaction).

  2,3-dihydro-1-benzofuran-4-ol is, for example, Helvetica Chimica Acta, 1933, 16, 121-129. From 1-benzofuran-4-ol obtained by the method described in Journal of the Chemical Society, 1948, page 894 (reduction of olefins) Reaction).

  3-methyl-2,3-dihydro-1-benzofuran-4-ol is an example of Journal of the Chemical Society. Society, 1951, 3-methyl-1-benzofuran-4-ol, which can be produced by the method described on pages 3229-3234, Journal of the Chemical Society (Journal of the Chemical Society), 1948, page 894 (reduction reaction of olefin).

  1-benzofuran-4-ol (1-benzofuran-4-ol) can be obtained, for example, by the method described in Helvetica Chimica Acta, 1933, Vol. 16, pages 121-129.

  3-methyl-1-benzofuran-4-ol is described in, for example, Journal of the Chemical Society, 1951, pages 3229-3234. It can be manufactured by the method.

  1-benzothiophen-4-ol is a method described in, for example, Journal of the American Chemical Society, 1935, 57, 1611-1615. Can be manufactured.

  2-Methyl-1,3-benzoxazol-4-ol is, for example, Journal of Medicinal Chemistry, 1987, Volume 30, It can be produced according to the method described in No. 1, pages 62-67.

  2,3-dihydro-1-benzofuran-7-ol is an example of commercially available 7-methoxy-1-benzofuran (7-methoxy-1-benzofuran-7-ol). benzofuran), Journal of the Chemical Society, 1948, page 894 (hydrogenation reaction of benzofuran) and Bioscience, Biotechnology, and Biochemistry. ), 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  1-benzofuran-7-ol, for example, is commercially available from 7-methoxy-1-benzofuran from Bioscience, Biotechnology and Biochemistry (Bioscience, Biotechnology, and Biochemistry), 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  1,3-benzodioxol-4-ol is a chemical fur from commercially available 1,2,3-benzenetriol. It can be produced by the method described in Chemical Pharmaceutical Bulletin, 1981, Vol. 29, No. 10, pages 2893-2898.

  2,3-dihydro-1,4-benzodioxin-5-ol (2,3-dihydro-1,4-benzodioxin-5-ol) is, for example, commercially available 1,2,3-benzenetriol (1, 2,3-benzenetriol), Journal of the Chemical Society: Parkin transaction I, 1988, pages 511-520.

  2-methyl-1,3-benzoxazol-7-ol is, for example, commercially available 3-nitro-1,2-benzenediol (3-nitro- 1,2-benzenediol), the method described in Liebigs Annalen der Chemie, 1957, 608, 128 (reduction reaction of nitro group to amino group), and Journal of Medicinal Chemistry (Journal of Medicinal Chemistry), 1987, Vol. 30, No. 1, pp. 62-67.

  2-bromo-4-tert-butylphenol can be produced, for example, by the method described in Tetrahedron, 1999, Vol. 55, No. 28, pages 8377-8384. .

  2-ethyl-4-iodophenol is a commercially available 2-ethylphenol, The Journal of Organic Chemistry, 1951, 16 volumes. , 1117-1120 pages.

  4-bromo-2-isopropylphenol can be obtained by the method described in, for example, Journal of Medicinal Chemistry, 1971, Vol. 14, No. 9, pages 789-792. Can be manufactured.

  2-cyclopropyl-4-methylphenol is, for example, from commercially available 2-bromo-1-methoxy-4-methylbenzene. , Tetrahedron Letters, 2000, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), and bioscience, biotechnology and biochemistry (Bioscience, Biotechnology, and Biochemistry), 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  5- (dimethylamino) -2-methylphenol is a method described, for example, in Journal of the Chemical Society, 1947, pages 182-191. Can be manufactured.

  5-methoxy-2-methylphenol can be produced, for example, by the method described in Chemical Abstracts, 1938, page 2519.

  2-ethyl-5-methoxyphenol is a method described in, for example, Chemical and Pharmaceutical Bulletin, 1979, Vol. 27, No. 6, pp. 1490-1494 Can be manufactured.

  2,5-diisopropylphenol can be produced, for example, by the method described in The Journal of Organic Chemistry, 1980, Vol. 45, No. 22, pages 4326-4329.

  2-cyclopropyl-5-fluorophenol is, for example, from the commercially available 2-bromo-5-fluorophenol, Helvetica Chimica Acta ), 1992, 75, page 457 (conversion of phenol to phenylmethoxymethyl ether, methoxymethylation reaction), and Tetrahedron Letters, 2000, 41, 4251 4255 page (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction) and tetrahedron 1998, 54, 15861-15869 (phenol of phenylmethoxymethyl ether) Conversion to demethoxymethylation reaction).

  For example, 5-chloro-2-cyclopropylphenol is a commercially available 4-chloro-2-methoxyphenol from The Journal of Organic Chemistry (The Journal of Organic Chemistry), 1997, Vol. 62, No. 2, pp. 261-274, and Tetrahedron Letters, 2000, 41, 4251. -4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction) and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, 1572- It can be produced according to the method described in page 1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-cyclopropyl-5-methylphenol is, for example, from the commercially available 2-methoxy-4-methylphenol, The Journal of Organic Chemistry (The Journal of Organic Chemistry), 1997, Vol. 62, No. 2, pp. 261-274, and Tetrahedron Letters, 2000, 41, 4251. -4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction) and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, 1572- It can be produced according to the method described in page 1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-cyclopropyl-5-ethylphenol is, for example, from the commercially available 4-ethyl-2-methoxyphenol, the Journal of Organic Chemistry (The Journal of Organic Chemistry), 1997, Vol. 62, No. 2, pp. 261-274, and Tetrahedron Letters, 2000, 41, 4251. -4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction) and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, 1572- It can be produced according to the method described in page 1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-cyclopropyl-5-isopropylphenol is, for example, from commercially available 3-isopropylphenol, Tetrahedron Letters, 1998, Vol. 39, 2947 method (phenol bromination reaction) and Helvetica Chimica Acta 1992, 75, page 457 (conversion of phenol to phenylmethoxymethyl ether, methoxymethylation reaction) ) And Tetrahedron Letters, 2000, Vol. 41, pages 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), and tetrahedron (Tetrahedron), 1998, Vol. 54, pages 15861-15869 can be produced according to the method described above (conversion of phenylmethoxymethyl ether to phenol, demethoxymethylation reaction).

  4-cyclopropyl-3-hydroxybenzonitrile, for example, from the commercially available 4-hydroxy-3-methoxybenzonitrile, the Journal of Organic Chemistry. (The Journal of Organic Chemistry), 1997, Vol. 62, No. 2, pages 261-274 (phenol trifluoromethanesulfonylation) and Tetrahedron Letters, 2000, 41 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, 1572-1574 or according to the method described in JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction) I can build it.

  5-Fluoro-2-[(1E) -1-propenyl] phenol (5-fluoro-2-[(1E) -1-propenyl] phenol), for example, Journal of the Chemical Society: Parkin Transaction I (Journal of the Chemical Society: Parkin transaction I), 1994, pages 1823-1831 (synthesis of 4-fluoro-2-hydroxybenzaldehyde) and organic synthesis (Organic Synthesis) ), Collective Volume, Vol. 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation), and Synthetic Communications, 1985, 15 , No. 10, pages 855-864 (conversion of carbonyl group to olefin, Wittg reaction), bioscience, biotechnology and biochemistry (Bioscience, Biotechnology, and Biochemistry), 1993, Vol. 57, No. 9, pages 1572-1574 or JP 11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction) Can be manufactured.

  5-Chloro-2-[(1E) -1-propenyl] phenol (5-chloro-2-[(1E) -1-propenyl] phenol) is, for example, the Journal of Organic Chemistry. 1964, 29, pages 2693-2698 (synthesis of 4-chloro-2-hydroxybenzaldehyde), organic synthesis, collective volume (Collective) Volume), Volume 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation reaction), Synthetic Communications, 1985, Vol. 15, No. 10, pages 855-864 (Conversion of carbonyl group to olefin, Wittg reaction) and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  4- (dimethylamino) -2-hydroxybenzaldehyde can be produced, for example, by the method described in German Patent (DE 105103).

  5-chloro-2-methoxyphenol is an organic synthesis or collective from commercially available 5-amino-2-methoxyphenol, for example. It can be produced according to the method described in Collective Volume, Vol. 2, pages 130-133 (conversion of anilines to chlorobenzene, Sandmeyer reaction, etc.).

  5-Bromo-2-methoxyphenol is an organic synthesis or collective from commercially available 5-amino-2-methoxyphenol, for example. The method described in Collective Volume, Volume 3, pages 185-187, or The Journal of Organic Chemistry, 1977, Volume 42, pages 242-2430. Conversion to benzene, Sandmeyer reaction, etc.).

  3-hydroxy-4-methoxybenzonitrile is synthesized from, for example, commercially available methyl 3,4-dimethoxybenzoate, Synthesis, 1998, 329. -It can be produced by the method described on page 332.

  2,5-dimethoxyphenol can be produced, for example, by the method described in The Journal of Organic Chemistry, 1987, Vol. 57, page 4485.

  2-bromo-6-fluorophenol is, for example, from commercially available 2-fluorophenol, Tetrahedron Letters, 1998, Vol. 39, 2947. It can be produced according to the method described on page (bromination reaction of phenol).

  2-Fluoro-6-propylphenol is, for example, from commercially available 2-fluorophenol, Organic Reactions, 1949, Vol. 2, 1-48 Page (allylation of phenol, Claisen transfer reaction) and the method described in Journal of the American Chemical Society, 1951, vol. 73, pages 4152-4156 (allyl group). To a propyl group, hydrogenation reaction).

  2-Fluoro-6-isopropylphenol is, for example, from commercially available 2-isopropyl-6-nitrophenol, Organic Synthesis, Collective Volume Vol. 4, 836-838 (conversion of phenol to phenyl methyl ether, methylation reaction), Liebigs Annalen der Chemie, 1975, 608, 128 (method of nitro group) (Reduction reaction to amino group), Synthesis, 1989, method described on page 905 (conversion reaction of amino group to fluorine atom), and bioscience, biotechnology and biochemistry (Bioscience, Biotechnolory, and Biochemistry) 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (phenone of phenyl methyl ether) In accordance with the conversion to desulfurization, demethylation reaction).

  2-cyclopropyl-6-fluorophenol is, for example, from commercially available 2-fluorophenol, Tetrahedron Letters, 1998, Vol. 39, 2947 page (bromination reaction of phenol) and Helvetica Chemica Acta, 1992, vol. 75, page 457 (conversion of phenol to phenylmethoxymethyl ether, methoxymethylation) Reaction) and the method described in Tetrahedron Letters, 2000, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), and tetrahedron (Tetrahedron) 1998, 54, 15861-15869 (conversion to phenylmethoxymethyl ether phenol, demethoxymethylation reaction).

  2-chloro-6-iodophenol is described in, for example, The Journal of Organic Chemistry, 1988, Vol. 53, No. 22, pages 5281-5287. It can be manufactured by the method.

  2-chloro-6-ethylphenol is produced, for example, by the method described in Journal of Chemical and Engineering Data, 1969, Vol. 14, p. 392 it can.

  2-chloro-6-cyclopropylphenol is, for example, from commercially available 2-chlorophenol, Tetrahedron Letters, 1998, Vol. 39, 2947 page (bromination reaction of phenol) and Helvetica Chimica Acta, 1992, vol. 75, page 457 (conversion of phenol to phenylmethoxymethyl ether, methoxymethylation) Reaction) and the method described in Tetrahedron Letters, 2000, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), and tetrahedron (Tetrahedron) 1998, 54, 15861-15869 (conversion to phenylmethoxymethyl ether phenol, demethoxymethylation reaction).

  2-chloro-6- (2-methyl-2-propenyl) phenol is, for example, from commercially available 2-chlorophenol. , Organic Reactions, 1949, Vol. 2, pp. 1-48 (phenol allylation, Claisen rearrangement reaction).

  2-Bromo-6-methylphenol can be produced, for example, by the method described in Tetrahedron Letters, 1998, Vol. 39, page 2947.

  2-bromo-6-ethylphenol is, for example, from commercially available 2-ethylphenol, Tetrahedron Letters, 1998, Vol. 39, 2947. It can be produced according to the method described on page (bromination reaction of phenol).

  2-Bromo-6-cyclopropylphenol (2-bromo-6-cyclopropylphenol), for example, from organic 2,6-dibromophenol, organic synthesis, collective volume (Collective) Volume), Volume 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation reaction) and Tetrahedron Letters, 2000, 41, 4251-4255 The described method (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction) and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or It can be produced according to the method described in JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  3-bromo-2-hydroxybenzonitrile is, for example, a commercially available 2-hydroxybenzonitrile from Tetrahedron Letters, 1998, Vol. 39. , Page 2947 (the bromination reaction of phenol).

  2-Bromo-6-methoxyphenol can be produced, for example, by the method described in Synthesis, 1999, Vol. 7, pages 1127-1134.

  2-iodo-6-methylphenol can be obtained, for example, by the method described in Australian Journal of Chemistry, 1997, Vol. 50, No. 7, pp. 767-770. Can be manufactured.

  2-ethyl-6-iodophenol is from the commercially available 2-ethylphenol, Australian Journal of Chemistry, 1997, 50, It can be produced according to the method described in No. 7, pages 767-770 (iodination reaction of phenol).

  2-iodo-6-isopropylphenol is more commercially available than 2-isopropylphenol, Australian Journal of Chemistry, 1997, 50 volumes, It can be produced according to the method described in No. 7, pages 767-770 (iodination reaction of phenol).

  2-Isopropyl-6-methylphenol is a method described in, for example, Bulletin de la Societe Chemique de France, 1962, pages 1700-1705. Can be manufactured.

  2-sec-butyl-6-methylphenol can be produced, for example, by the method described in Angewandte Chemie, 1957, 69, 699, 703 . Further, for example, from commercially available 2-methylphenol, Organic Reactions, 1949, Vol. 2, page 1-48 (phenol allylation, Claisen transfer reaction), Journal of the American It can also be produced according to the method described in Journal of the American Chemical Society, 1951, Vol. 73, pages 4152-4156 (conversion of allyl group to propyl group, hydrogenation reaction).

  2-cyclopropyl-6-methylphenol is, for example, from commercially available 2-hydroxy-3-methylbenzaldehyde, organic synthesis, Collective Volume, Volume 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation reaction) and The Journal of Organic Chemistry, 1963 28, 1128 or Synthetic Communications, 1985, 15, 10, 855-864 (conversion of carbonyl group to olefin, Wittg reaction) and Organic Reactions ( Organic Reactions), 1973, 20, pp. 1-131, or Journal of the American Chemical Society (J ournal of the American Chemical Society), 1975, 97, 3428 or Tetrahedron Letters, 1998, 39, 8621-8624 (construction of cyclopropyl groups, Simmons-Smith reaction) ), And the method described in Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP 11-322755 (to the phenol of phenyl methyl ether) Conversion, demethylation reaction).

  2-methoxy-6-methylphenol is, for example, a synthetic communication from commercially available 1,2-dimethoxy-3-methylbenzene (Synthetic Communications). ), 1996, Vol. 26, No. 1, pp. 49-62.

  2,6-diethylphenol (2,6-diethylphenol) can be produced, for example, by the method described in Journal of Medicinal Chemistry, 1960, Vol. 2, pages 201-212.

  2-cyclopropyl-6-ethylphenol is, for example, from commercially available 2-ethylphenol, Tetrahedron Letters, 1998, Vol. 39, 2947 page (bromination reaction of phenol) and Helvetica Chimica Acta, 1992, vol. 75, page 457 (conversion of phenol to phenylmethoxymethyl ether, methoxymethylation) Reaction) and the method described in Tetrahedron Letters, 2000, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), and tetrahedron (Tetrahedron) 1998, 54, 15861-15869 (conversion to phenylmethoxymethyl ether phenol, demethoxymethylation reaction).

  2,6-dipropylphenol is a method described in, for example, Liebigs Annalen der Chemie, 1919, Vol. 418, pages 90-91 (2,6- Diallylphenol (synthesis of 2,6-diallylphenol) and the method described in Bulletin de la Societe Chemique de France, 1937, Vol. 5, No. 4, pages 1080-1083 (Conversion of allyl group to propyl group, hydrogenation reaction)

  2-cyclopropyl-6-isopropylphenol (Journal of the Chemical Society: Parkin transaction I), 1980, 1862-1865, for example Page (Synthesis of 2-hydroxy-3-isopropylbanzaldehyde), Organic Synthesis, Collective Volume, Vol. 4, 836-838 Page (conversion of phenol to phenyl methyl ether, methylation reaction) and The Journal of Organic Chemistry, 1963, 28, 1128 or Synthetic Communications, 1985, Vol. 15, No. 10, pages 855-864 (carbonyl group (Conversion to olefin, Wittg reaction), and Organic Reactions, 1973, 20, 1-131 or Journal of the American Chemical Society, 1975, 97, 3428 or the method described in Tetrahedron Letters, 1998, Vol. 39, pages 8621-8624 (construction of cyclopropyl group, Simmons-Smith reaction), and bioscience Biotechnology and Biochemistry Biotechnology, and Biochemistry), 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  3-tert-butyl-6-cyclopropylphenol is, for example, from commercially available 3-tert-butyl-2-hydroxybenzaldehyde. Organic Synthesis, Collective Volume, Vol. 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation), and Journal of Organic Chemistry (The Journal of Organic Chemistry), 1963, 28, 1128 or Synthetic Communications, 1985, 15, 10, 855-864 (Conversion of carbonyl group to olefin, Wittg reaction) ) And Organic Reactions, 1973, 20, pp. 1-131 or Journal of the American Chemical Saety (Journal of the American Chemical Society), 1975, 97, 3428 or Tetrahedron Letters, 1998, 39, 8621-8624 (construction of cyclopropyl group, Simmons- Smith reaction), and the method described in Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755. (Conversion to phenol, demethylation reaction).

  2,6-dicyclopropylphenol is a method described in, for example, Tetrahedron Letters, 1997, Vol. 38, No. 17, pages 3111-3114 (2-hydroxyisophthalate). Synthesis of aldehyde), and organic synthesis, collective volume, volume 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation reaction), and The method described in The Journal of Organic Chemistry, 1963, 28, 1128 or Synthetic Communications, 1985, 15, 10, 855-864 (olefins of carbonyl group) Conversion, Wittg reaction), and Organic Reactions, 1973, 20, pp. 1-131 or journal The method described in the Journal of the American Chemical Society, 1975, 97, 3428 or Tetrahedron Letters, 1998, 39, 8621-8624. (Structure, Simmons-Smith reaction) and the method described in Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, 1572-1574 or JP-A-11-322755 It can be produced according to the conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-Cyclopropyl-6-methoxyphenol (Helvetica Chimica Acta) is available from, for example, commercially available 2-hydroxy-3-methoxybenzaldeyde. 1992, 75, page 457 (conversion of phenol to phenylmethoxymethyl ether, methoxymethylation reaction), and The Journal of Organic Chemistry, 1963, 28 1128 or Synthetic Communications, 1985, Vol. 15, No. 10, pages 855-864 (conversion of carbonyl group to olefin, Wittg reaction), and Organic Reactions (Organic Reactions), 1973, 20-1-131 or Journal of the Amer Society ican Chemical Society), 1975, 97, 3428 or Tetrahedron Letters, 1998, 39, 8621-8624 (construction of cyclopropyl groups, Simmons-Smith reaction), and , Tetrahedron, 1998, 54, 15861-15869 (conversion to phenylmethoxymethyl ether to phenol, demethoxymethylation reaction).

  2-cyclopropyl-6-ethoxyphenol (Organic Synthesis) from commercially available 3-ethoxy-2-hydroxybenzaldehyde, for example, Collective Volume, Volume 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation reaction) and The Journal of Organic Chemistry, 1963 28, 1128 or Synthetic Communications, 1985, 15, 10, 855-864 (conversion of carbonyl group to olefin, Wittg reaction) and Organic Reactions ( Organic Reactions), 1973, 20, pp. 1-131 or Journal of the American Chemical Sosae (Journal of the American Chemical Society), 1975, 97, 3428 or Tetrahedron Letters, 1998, 39, 8621-8624 (construction of cyclopropyl group, Simmons- Smith reaction), and the method described in Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755. (Conversion to phenol, demethylation reaction).

  2,6-di [(1E) -1-propenyl] phenol (2,6-di [(1E) -1-propenyl] phenol) is, for example, Liebigs Annalen der Chemie, 1919. 418, 90-91 (Synthesis of 2,6-diallylphenol) and Journal of the American Chemical Society, 1956, 78, 1709-1713 It can be produced by the method described in the page (isomerization reaction).

  2,6-diallylphenol can be produced, for example, by the method described in Liebigs Annalen der Chemie, 1919, 418, 90-91.

  3,5-diisopropylphenol can be produced, for example, by the method described in US Pat. No. 2790010.

  2-Bromo-3,5-dimethylphenol (Bulletin of the Chemical Society of Japan) from commercial 3,5-dimethylphenol (Bulletin of the Chemical Society of Japan) the Chemical Society of Japan), 1993, 66, 1576 (phenol bromination reaction).

  3,5-dimethyl-2-propylphenol is an example of Bulletin of the Chemical Society of Japan, 1968, Vol. 41, No. 3. , 745-746.

  2-cyclopropyl-3,5-dimethylphenol, for example, is commercially available from Tetrahedron Letters than 3,5-dimethylphenol. ), 1998, 39, page 2947 (phenol bromination reaction), and organic synthesis, collective volume, volume 4, pages 836-838 ( (Phenol to phenylmethyl ether, methylation reaction) and the method described in Tetrahedron Letters, 1979, 20, 4159-4162 or Tetrahedron, 1997, 53 Vol. 43, pages 14599-14614 or Bulletin of the Chemical Society of Japan, 1971, vol. 44, pages 2237-2248 (aromatic Conversion reaction of bromide to aromatic aldehyde) and The Journal of Organic Chemistry, 1963, 28, 1128 or Synthetic Communications, 1985, 15, 10 855-864 (conversion of carbonyl group to olefin, Wittg reaction) and Organic Reactions, 1973, 20, pp. 1-131 or Journal of the American Chemical Society (Journal of the American Chemical Society), 1975, 97, 3428 or Tetrahedron Letters, 1998, 39, 8621-8624 (construction of cyclopropyl groups, Simmons-Smith reaction) Bioscience, Biotechnology, and Biochemistry ), 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  3,5-dimethyl-2- (methylsulfanyl) phenol is, for example, Tetrahedron Letters, 1999, 40, 35, 6357. -6358 page.

  2-bromo-3,6-dimethylphenol is, for example, from Tetrahedron Letters from commercially available 3,6-dimethylphenol. 1998, Vol. 39, p. 2947 (production of phenol bromination).

  6-Bromo-3-fluoro-2-methylphenol is a journal from, for example, commercially available 3-fluoro-2-methylbenzaldehyde. Of the Chemical Society: Perfluorotransaction I (Journal of the Chemical Society: Parkin transaction I), 1974, page 1353, can be produced according to the method described in 3-fluoro-2-methylphenol (3-fluoro-2 -methylphenol) can be produced according to the method described in Tetrahedron Letters, 1998, Vol. 39, page 2947 (bromination reaction of phenol).

  6-bromo-3-chloro-2-methylphenol is a commercially available 1-chloro-3-methoxy-2-methylphenol (1-chloro-3-methoxy-2) -methylbenzene) can be produced according to the methods described in Organic Synthesis, Collective Volume, Vol. 5, pages 412-414 (conversion of phenylmethyl ether to phenol, demethylation reaction) Produced from 3-chloro-2-methylphenol according to the method described in Tetrahedron Letters, 1998, 39, 2947 (bromination of phenol) it can.

  3-chloro-6-cyclopropyl-2-methylphenol is a commercially available 1-chloro-3-methoxy-2-methylphenol. -2-methylbenzene) to organic synthesis, collective volume, volume 5, pages 412-414 (conversion of phenylmethyl ether to phenol, demethylation reaction) From 3-chloro-2-methylphenol that can be produced, the method described in Tetrahedron Letters, 1998, 39, 2947 (bromination reaction of phenol), Helvetica Chimica Acta, 1992, volume 75, page 457 (conversion of phenol to phenylmethoxymethyl ether, methoxymethylation reaction), and tetrahedron letters (Tetrahedron Lett ers), 2000, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), and Tetrahedron, 1998, 54, 15861-15869 (Conversion of phenylmethoxymethyl ether to phenol, demethoxymethylation reaction).

  6-Bromo-2,3-dimethylphenol is, for example, from the commercially available 2,3-dimethylphenol, Tetrahedron Letters 1998, vol. 39, page 2947 (phenol bromination reaction).

  6-cyclopropyl-2,3-dimethylphenol is, for example, from Tetrahedron Letters from 2,3-dimethylphenol, which is commercially available. , 1998, 39, page 2947 (phenol bromination reaction) and the method described in Helvetica Chimica Acta, 1992, 75, page 457 (phenol phenylmethoxymethyl). Conversion to ether, methoxymethylation reaction), and the method described in Tetrahedron Letters, 2000, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), Further, it can be produced according to the method described in Tetrahedron, 1998, Vol. 54, pages 15861-15869 (conversion of phenylmethoxymethyl ether to phenol, demethoxymethylation reaction).

  2-hydroxy-3,4-dimethylbenzaldehyde O-methyloxime is obtained from, for example, commercially available 2,3-dimethylphenol, Method described in Tetrahedron Letters, 1998, Vol. 39, page 2947 (bromination reaction of phenol) and method described in Helvetica Chimica Acta, 1992, vol. 75, page 457 (Conversion of phenol to phenylmethoxymethyl ether, methoxymethylation reaction) and the method described in Tetrahedron Letters, 1979, Vol. 20, pages 4159-4162, or Tetrahedron, 1997 Year, 53, 43, 14599-14614, or Bulletin of the Chemical Society of Japan, 1971, 44, 2237-2248 Described in (Conversion reaction of aromatic bromide to aromatic aldehyde) and Journal of the Chemical Society: Perkin transactions I, 1979, pages 643-645 And the method described in (Tetrahedron, 1998, 54, 15861-15869 (conversion of phenylmethoxymethyl ether to phenol, demethoxymethylation reaction) Can be manufactured.

  6-methoxy-2,3-dimethylphenol is, for example, from the commercially available 3,4-dimethylphenol, Tetrahedron Letters 1998, 39, page 2947 (phenol bromination reaction) and Tetrahedron Letters, 1979, 20, page 4159-4162 or tetrahedron (Tetrahedron) 1997, 53, 43, 14599-14614 or Bulletin of the Chemical Society of Japan, 1971, 44, 2237-2248 (Conversion reaction of aromatic bromide to aromatic aldehyde) and Journal of the Chemical Society: Parkin transaction I, 1974, page 1353 It can be prepared according to the method.

  6-bromo-3-methoxy-2-methylphenol is a commercially available 2-methyl-1,3-benzenediol 3-methoxy-, which can be produced according to the method described in Organic Synthesis, Collective Volume, Volume 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation reaction) It can be produced from 2-methylphenol in accordance with the method described in Tetrahedron Letters, 1998, Vol. 39, page 2947 (bromination reaction of phenol).

  6-cyclopropyl-3-methoxy-2-methylphenol is a commercially available 2-methyl-1,3-benzenediol. ) Can be produced according to the method described in Organic Synthesis, Collective Volume, Vol. 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation reaction). From 2-methoxyphenol (3-methoxy-2-methylphenol), the method described in Tetrahedron Letters, 1998, Vol. 39, page 2947 (phenol bromination reaction), and Helvetica Kimika Actor ( Helvetica Chimica Acta), 1992, volume 75, page 457 (conversion of phenol to phenylmethoxymethyl ether, methoxymethylation reaction), and Tetrahedron Letters, 200 0, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction) and Tetrahedron, 1998, 54, 15861-15869 It can be produced according to the method (conversion of phenylmethoxymethyl ether to phenol, demethoxymethylation reaction).

  2-cyclopropyl-3,6-dimethylphenol is, for example, Tetrahedron Letters rather than commercially available 2,5-dimethylphenol. 1998, Vol. 39, page 2947 (Phenol bromination reaction) and organic synthesis, collective volume, vol. 4, pages 836-838 (phenol) Conversion to phenyl methyl ether, methylation reaction), and the method described in Tetrahedron Letters, 1979, 20, 4159-4162 or Tetrahedron, 1997, 53 No. 43, pages 14599-14614, or Bulletin of the Chemical Society of Japan, 1971, vol. 44, pages 2237-2248 (aromatic And the Journal of Organic Chemistry, 1963, 28, 1128 or Synthetic Communications, 1985, 15, 10 855-864 (conversion of carbonyl group to olefin, Wittg reaction) and Organic Reactions, 1973, 20, pp. 1-131 or Journal of the American Chemical Society (Journal of the American Chemical Society), 1975, 97, 3428 or Tetrahedron Letters, 1998, 39, 8621-8624 (construction of cyclopropyl groups, Simmons-Smith reaction) Bioscience, Biotechnology, and Biochemistry 1993, Vol. 57, No. 9, (conversion of phenylmethyl ether phenol, demethylation reaction) 1572-1574 page or the method described in JP-A-11-322755 can be produced according to.

  2-allyl-6-ethyl-3-methoxyphenol is, for example, Chemical and Pharmaceutical Bulletin, 1979, Vol. 27, No. 6. From 2-ethyl-5-methoxyphenol, which can be produced by the method described on pages 1490-1494, Organic Reactions, 1949, Volume 2, pages 1-48 Can be produced according to the above method (phenol allylation reaction, Claisen rearrangement).

  3,6-dimethyl-2-[(methylsulfanyl) methyl] phenol is an example of the Journal of the American Chemical Society. 1966, Vol. 88, No. 24, pages 5855-5864.

  5-Bromo-4-indanol is, for example, from the commercially available 4-hydroxy-1-indanone, Journal of the American Chemical Society (Journal of the American Chemical Society), 1946, Vol. 68, page 2487 (reduction reaction of carbonyl group Wolff-Kishner reduction reaction), and Tetrahedron Letters, 1998, vol. 39, page 2947. It can be produced according to the method (bromination reaction of phenol).

  5-Methyl-4-indanol is, for example, from the commercially available 4-hydroxy-1-indanone, Journal of the American Chemical Society (Journal of the American Chemical Society), 1946, vol. 68, page 2487 (reduction of carbonyl group, Wolff-Kishner reduction) and Tetrahedron Letters, 1998, vol. 39, page 2947. The method (bromination reaction of phenol) and the method described in Helvetica Chimica Acta, 1992, 75, 457 (conversion of phenol to phenylmethoxymethyl ether, methoxymethylation reaction), and Helvetica Chimica Acta, 1990, Vol. 73, pages 417-425 (conversion reaction of bromo group to methyl group), and tetrahedron, 1998, vol. 54 , 15861- It can be produced according to the method described on page 15869 (conversion of phenylmethoxymethyl ether to phenol, demethoxymethylation reaction).

  5-ethyl-4-indanol, for example, is commercially available from 4-hydroxy-1-indanone, Journal of the American Chemical Society (Journal of the American Chemical Society), 1946, vol. 68, page 2487 (reduction of carbonyl group, Wolff-Kishner reduction) and Tetrahedron Letters, 1998, vol. 39, page 2947. The method (bromination reaction of phenol) and the method described in Helvetica Chimica Acta, 1992, vol. 75, page 457 (conversion of phenol to phenylmethoxymethyl ether, methoxymethylation reaction), and Helvetica chimica Acta, 1990, Vol. 73, pages 417-425 (conversion reaction of bromo group to ethyl group), and tetrahedron, 1998, vol. 54 , 15861- It can be produced according to the method described on page 15869 (conversion of phenylmethoxymethyl ether to phenol, demethoxymethylation reaction).

  5-cyclopropyl-4-indanol, for example, is commercially available from 4-hydroxy-1-indanone, Journal of the American Chemical Society (Journal of the American Chemical Society), 1946, vol. 68, page 2487 (reduction reaction of carbonyl group Wolff-Kishner reduction reaction) and Tetrahedron Letters, 1998, vol. 39, page 2947 And the method described in Organic Synthesis, Collective Volume, Vol. 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation reaction) ) And Tetrahedron Letters, 2000, Vol. 41, pages 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (Conversion of phenylmethyl ether to phenol) , Demethylation reaction).

  6-methyl-2,3-dihydro-1-benzofuran-7-ol is, for example, tetrahedron letters, 1998 , Vol. 39, page 2947, from 2-methoxy-3-methylphenol, Journal of the Chemical Society: Perkin Transactions I (Journal of the Chemical Society : Perkin transactions I) 1988, method described on page 3029 (construction of benzofuran ring), and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, 1572-1574 Or 6-methyl-1-benzofuran (6-methyl-1-benzofuran) which can be produced according to the method described in JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction) -7-ol) It can be produced according to the method described in Journal of the Chemical Society, 1948, p. 894 (olefin reduction reaction).

  6-Bromo-1-benzofuran-7-ol is an example of a bioscience from a commercially available 7-methoxy-1-benzofuran. Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (Conversion of phenylmethyl ether to phenol, demethylation) Reaction) and the method described in Tetrahedron Letters, 1998, Vol. 39, page 2947 (bromination reaction of phenol).

  6-Methyl-1-benzofuran-7-ol is produced, for example, by the method described in Tetrahedron Letters, 1998, Vol. 39, page 2947. From 2-methoxy-3-methylphenol, Journal of the Chemical Society Perkin transactions I, 1988, page 3029 Method (construction of benzofuran ring) and the method described in Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 It can be produced according to (conversion of phenylmethyl ether to phenol, demethylation reaction).

  6-cyclopropyl-1-benzofuran-7-ol is, for example, biosynthetic from commercially available 7-methoxy-1-benzofuran (7-methoxy-1-benzofuran). Science Biotechnology and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (Conversion of phenylmethyl ether to phenol, demethylation) And the method described in Tetrahedron Letters, 1998, 39, 2947 (bromination reaction of phenol) and Helvetica Chimica Acta, 1992, 75 , Page 457 (conversion of phenol to phenylmethoxymethyl ether, methoxymethylation reaction) and Tetrahedron Letters, 2000, 41, 4251-4255 And the method described in Tetrahedron, 1998, 54, 15861-15869 (Phenylmethoxymethyl ether to phenol). Conversion, demethoxymethylation reaction).

  2,4-dicyclopropyl-6-fluorophenol is, for example, from commercially available 2-fluorophenol, Tetrahedron Letters, 1998 39, page 2947 (the bromination reaction of phenol) and the method described in Helvetica Chimica Acta, 1992, volume 75, page 457 (phenol to phenylmethoxymethyl ether) Conversion, methoxymethylation reaction), and the method described in Tetrahedron Letters, 2000, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), and tetra It can be produced according to the method described in Tetrahedron, 1998, Vol. 54, pages 15861-15869 (conversion of phenylmethoxymethyl ether to phenol, demethoxymethylation reaction).

  2,4-dibromo-3,6-dimethylphenol is a tetrahedron letter, for example, from commercially available 3,6-dimethylphenol. (Tetrahedron Letters), 1998, Vol. 39, p. 2947 (production of phenol bromination).

  2-Bromo-4,6-dimethylphenol is, for example, from the commercially available 2,4-dimethylphenol, Tetrahedron Letters 1998, vol. 39, page 2947 (phenol bromination reaction).

  2-ethyl-4,6-diiodophenol is more commercially available than 2-ethylphenol from the Australian Journal of Chemistry, 1997. , 50, No. 7, pp. 767-770 can be produced according to the method (iodination reaction of phenol).

  2-cyclopropyl-4,6-dimethylphenol is, for example, from the commercially available 2,4-dimethylphenol, Tetrahedron Letters , 1998, 39, page 2947 (phenol bromination reaction) and the method described in Helvetica Chimica Acta, 1992, 75, page 457 (phenol phenylmethoxymethyl). Conversion to ether, methoxymethylation reaction), and the method described in Tetrahedron Letters, 2000, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), Further, it can be produced according to the method described in Tetrahedron, 1998, Vol. 54, pages 15861-15869 (conversion of phenylmethoxymethyl ether to phenol, demethoxymethylation reaction).

  2-bromo-3,5,6-trimethylphenol (2-bromo-3,5,6-trimethylphenol) is, for example, from commercially available 2,3,5-trimethylphenol (2,3,5-trimethylphenol), It can be produced according to the method described in Tetrahedron Letters, 1998, Vol. 39, page 2947 (bromination reaction of phenol).

  5,6-dimethyl-4-indanol is, for example, commercially available 7-methyl-2H-chromen-2-one According to the method described in Journal of Chemical Society of Japan, 1974, pages 136-146, and the method described in Organic Reactions, 1941, Vol. 1, page 155 (Clemmensen reduction).

  1,2,3,5,6,7-hexahydro-s-indacene-4-ol (1,2,3,5,6,7-hexahydro-s-indacen-4-ol) is, for example, commercially available From Indane, Journal of the American Chemical Society, 1977, 99, pages 8007-8014, Organic Reactions, 1941, 1 155, page 155 (Clemmensen reduction) and The Journal of Organic Chemistry, 1977, Vol. 42, pages 3260-3264.

  3- (1,3-dioxolan-2-yl) phenol (3- (1,3-dioxolan-2-yl) phenol), for example, from 3-hydroxybenzaldehyde, tetrahedron letters ( Tetrahedron Letters), 1989, Vol. 30, No. 13, pages 1609-1612.

  3 '-(trifluoromethyl) [1,1'-biphenyl] -3-ol (3'-(trifluoromethyl) [1,1'-biphenyl] -3-ol) is an example of commercially available 3-iodophenol. From (3-iodophenol) and 3- (trifluoromethyl) phenylboronic acid, the method described in Chemical Reviews, 1995, Vol. 95, pages 2457-2483 (phenylation) Reaction, Suzuki-Miyaura coupling reaction).

  3-hydroxy-4-methylbenzonitrile can be produced, for example, by the method described in Monatshefte fur Chemie, 1957, 88, 228,230.

  Ethyl 3-hydroxy-4-methylbenzoate is a method described in, for example, The Journal of Organic Chemistry, 1961, Vol. 26, pages 1732-1734. Can be manufactured.

  3-hydroxy-4-methylbenzamide (3-hydroxy-4-methylbenzamide) is, for example, a phosphorous sulfur (3-hydroxy-4-methylbenzoic acid) Phosphorus and Sulfur), 1980, Vol. 9, pp. 155-164.

  3,6-dimethyl-2-propylphenol is described in, for example, Journal of Polymer Science, 1948, 3, 448, 452. It can be manufactured by the method.

  2-hydroxy-3,4,6-trimethylbenzaldehyde is, for example, Liebigs Annalen der Chemie, 1906, 347, 379. It can manufacture by the method of description.

  2-hydroxy-3,4,6-trimethylbenzaldehyde O-methyloxime is, for example, Liebigs Annalen der Chemie, 1906. 347, page 379 (synthesis of 2-hydroxy-3,4,6-trimethylbenzaldehyde) and Chemical Pharmaceutical Bulletin, 1988, Vol. 36, No. 8, It can be produced according to the method described on pages 3134-3137.

  2- [1- (methoxymethyl) cyclopropyl] phenol is an example of The Journal of Organic Chemistry, 1942, Vol. 7, 444. From 2-methoxy-1- (2-methoxyphenyl) ethanone, which can be produced by the method described on page -456, The Journal of Organic Chemistry ), 1963, 28, 1128 or Synthetic Communications, 1985, 15, 10, 855-864 (conversion of carbonyl group to olefin, Wittig reaction), and Organic Reactions, 1973, 20, pp. 1-131 or Journal of the American Chemical Society, 1975, 97 3428 or the method described in Tetrahedron Letters, 1998, Vol. 39, pages 8621-8624 (cyclopropyl group construction, Simmons-Smith reaction), and bioscience, biotechnology and Biotechnology, and Biochemistry), 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2- (1-methoxycyclopropyl) phenol (2- (1-methoxycyclopropyl) phenol) is described in, for example, The Journal of Organic Chemistry, 1998, Vol. 63, pages 4632-4635. From 1-methoxy-2- (1-methoxyvinyl) benzene, which can be produced by the method, Organic Reactions, 1973, 20, 1-131 Or the method described in Journal of the American Chemical Society, 1975, 97, 3428 or Tetrahedron Letters, 1998, 39, 8621-8624 (cyclopropyl) Group construction, Simmons-Smith reaction), and Bioscience, Biotechnology, and Biochemistry, 1993, 57, 9, 1572-1574 Ku is (conversion to phenol phenyl ether, demethylation reaction) method described in JP-A-11-322755 can be produced according to.

  2- (2-hydroxyphenyl) cyclopropanecarbonitrile is described, for example, in Journal of Medicinal Chemistry, 1988, Vol. 31, No. 1, pages 37-54 From 3- (2-methoxyphenyl) acrylonitrile (Bioscience, Biotechnology, and Biochemistry), 1993, volume 57, 9 No., pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction), and Helvetica Chimica Acta, 1992, Vol. 75, 457 Page (conversion of phenol to phenylmethoxymethyl ether, methoxymethylation reaction) and The Journal of The method described in The Journal of Organic Chemistry, 1973, 38, 1793-1797 or The Journal of Organic Chemistry, 1970, 35, 374-379 (cyclopropane) And a method described in Tetrahedron, 1998, Vol. 54, pages 15861-15869 (conversion of phenylmethoxymethyl ether to phenol, demethoxymethylation reaction).

  2- (2-ethoxycyclopropyl) phenol can be produced, for example, by the method described in Heterocycles, 1998, Vol. 48, No. 7, pages 1373-1394. From [2- (methoxymethoxy) phenyl] methanol, the method described in The Journal of Organic Chemistry, 1981, 46, 5143-5147 ( (Conversion of benzyl alcohol to benzyl chloride) and the method described in Journal of the American Chemical Society, 1973, Vol. 95, No. 2, pages 581-582 (construction of cyclopropyl group) And according to the method described in Tetrahedron, 1998, 54, 15861-15869 (conversion of phenylmethoxymethyl ether to phenol, demethoxymethylation reaction) It can be granulated.

  2- (2,2-difluorocyclopropyl) phenol is, for example, Bulletin de la Societe Chemique de France, 1995, 850 -1- (2,2-difluorovinyl) -2-methoxybenzene (1- (2,2-difluorovinyl) -2-methoxybenzene), which can be produced by the method described on page 856, the Journal of Organic Chemistry (The Journal of Organic Chemistry), 1973, 38, 1793-1797 or The Journal of Organic Chemistry, 1970, 35, 374-379 (cyclopropanation reaction), and According to the method described in Organic Synthesis, Collective Volume, Volume 5, pages 412-414 (conversion of phenylmethyl ether to phenol, demethylation reaction) It can be produced.

  2- (2,2-dichlorocyclopropyl) phenol is described, for example, in Heterocycles, 1998, Vol. 48, No. 7, pages 1373-1394 From 2- (methoxymethoxy) benzaldehyde, which can be produced by the method of The Journal of Organic Chemistry, 1963, 28, 1128 or Synthetic Communications 1985, 15, 10, 855-864 (conversion of carbonyl group to olefin, Wittig reaction) and Synthetic Communications, 1999, 29, 23, 4101 -4112 (conversion of olefins to dichlorocyclopropane) and tetrahedron, 1998, 54, 15861-15869 Conversion to phenol of methoxy methyl ether, can be prepared analogously to demethoxylation methylation reaction).

  2- (2,2-dibromocyclopropyl) phenol (2- (2,2-dibromocyclopropyl) phenol) is synthetic, for example, from commercially available 1-methoxy-2-vinylbenzene. Synthetic Communications, 1999, 29, 23, pages 4101-4112 (using bromoform instead of chloroform, conversion of olefin to dibromocyclopropane), and organic synthesis It can be produced according to the method described in Collective Volume, Vol. 5, pages 412-414 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-isopropenylphenol is, for example, from the commercially available 1- (2-methoxyphenyl) ethanone, The Journal of Organic Chemistry, 1963, 28, 1128 or Synthetic Communications, 1985, 15, 15, 855-864 (conversion of carbonyl group to olefin, Wittig reaction) and bioscience Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (Conversion of phenylmethyl ether to phenol, demethylation) It can be produced according to (Reaction).

  3- (2-hydroxyphenyl) acrylonitrile is described in, for example, Journal of Medicinal Chemistry, 1988, Vol. 31, No. 1, pages 37-54 From 3- (2-methoxyphenyl) acrylonitrile that can be produced by the method, Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, It can be produced according to the method described in 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2-ethynylphenol is described in, for example, Canadian Journal of Chemistry, 1997, Vol. 75, No. 9, pages 1256-1263 from commercially available 1-benzofuran. It can manufacture by the method of.

  Bicyclo [4.2.0] octa-1,3,5-trien-2-ol is an example of The Journal of Organic Chemistry ( The Journal of Organic Chemistry), 1982, 47, 2393-2396, 5-methoxybicyclo [4.2.0] octa-1,3,5-trien-7-one (5-methoxybicyclo) [4.2.0] octa-1,3,5-trien-7-one), Organic Reactions, 1941, Volume 1, page 155 (Clemmensen reduction) and Bioscience Bio Bioscience, Biotechnology, and Biochemistry, 1993, 57, 9, 1572-1574 or JP-A-11-322755 or Organic Synthesis, Collective Volume, Volume 5. , 412-414 (conversion of phenyl methyl ether to phenol, Can be prepared analogously to the methylation reaction).

  2-Bromo-6-chlorophenol is, for example, from commercially available 2-chlorophenol, Tetrahedron Letters, 1998, Vol. 39, 2947. It can be produced according to the method described on page (bromination reaction of phenol).

  3-bromo-2-hydroxybenzonitrile is, for example, a commercially available 2-hydroxybenzonitrile from Tetrahedron Letters, 1998, Vol. 39. , Page 2947 (the bromination reaction of phenol).

  2- (2,2-dichlorocyclopropyl) -6-methylphenol (2- (2,2-dichlorocyclopropyl) -6-methylphenol) is, for example, commercially available 2-hydroxy-3-methylbenzaldehyde (2-hydroxy- 3-methylbenzaldehyde), organic synthesis, collective volume, volume 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation reaction), and the The method described in The Journal of Organic Chemistry, 1963, 28, 1128 or Synthetic Communications, 1985, 15, 10, 855-864 (olefins of carbonyl group) Conversion, Wittig reaction) and the method described in Synthetic Communications, 1999, 29, 23, pages 4101-4112 (Conversion of olefin to dichlorocyclopropane) and organic synthesis, collective volume, Vol. 5, pages 412-414 (conversion of phenylmethyl ether to phenol, demethylation) Can be produced according to the following reaction.

  For example, 2-methyl-6-vinylphenol is an organic synthesis or collective from commercially available 2-hydroxy-3-methylbenzaldehyde. Collective Volume, Vol. 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation reaction) and The Journal of Organic Chemistry, 1963 28, 1128 or Synthetic Communications, 1985, 15, 10, 855-864 (conversion of carbonyl group to olefin, Wittig reaction) and bioscience biotechnology And Biochemistry (Bioscience, Biotechnology, and Biochemistry), 1993, 57, 9, 1572-1574 or JP It can be produced according to the method described in Hei 11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  6-cyclopropyl-3-fluoro-2-methylphenol is, for example, from commercially available 3-fluoro-2-methylbenzaldehyde. , The Journal of Organic Chemistry, 1999, 64, 7921-7928 or Journal of the Chemical Society: Parkin transaction I, 1974, 1353 page (Baeyer-Villiger oxidation, conversion of aromatic aldehyde to phenol) and Tetrahedron Letters, 1998, Vol. 39, page 2947 ) And Organic Synthesis, Collective Volume, Vol. 4, pages 836-838 Conversion to phenyl methyl ether, methylation reaction) and the method described in Tetrahedron Letters, 2000, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), And a method described in Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (Conversion of phenylmethyl ether to phenol) , Demethylation reaction).

  5-methyl-1-benzofuran-4-ol can be obtained, for example, by the method described in Tetrahedron, 1995, 51, 4009-4022. Can be produced from methyl 4-hydroxy-1-benzofuran-5-carboxylate, organic synthesis, collective volume, volume 4, 836 -838 (conversion of phenol to phenyl methyl ether, methylation reaction) and The Journal of Organic Chemistry, 2001, Vol. 66, pages 4965-4972. The method (reduction of ester to alcohol) and the method described in Journal of Medicinal Chemistry, 1999, Vol. 42, No. 6, pp. 1007-1017 (benzyl alcohol of benzyl alcohol) Conversion to tansulfonyl ester) and the method described in The Journal of Organic Chemistry, 1969, 34, 3923 or Synthetic Communications, 2001, 31, 9 No. 1373-1382 (reduction reaction of halogenated compounds, tosylate and mesylate) and Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, 1572 -1574 or according to the method described in JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  2- (2-chloro-2-fluorocyclopropyl) phenol is, for example, Heterocycles, 1998, Vol. 48, No. 7, 1373- From 2- (methoxymethoxy) benzaldehyde which can be produced by the method described on page 1394, Journal of Fluorine Chemistry 1983, Vol. 23, page 339-357 ( (Conversion of carbonyl group to chlorofluoroolefin) and The Journal of Organic Chemistry, 1973, 38, 1793-1797 or The Journal of Organic Chemistry, 1970 35, pages 374-379 (cyclopropanation reaction), organic synthesis, collective volume (Col lective Volume), Vol. 5, pp. 412-414.

  3- (benzyloxy) phenol can be obtained, for example, by the method described in The Journal of Organic Chemistry, 1997, Vol. 62, No. 10, pages 3062-3075. Can be manufactured.

  1-methyl-1H-indol-4-ol (1-methyl-1H-indol-4-ol) is, for example, commercially available 4-methoxy-1-methyl-1H-indole (4-methoxy-1-methyl- 1H-indole), the method described in Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755. (Conversion to phenol, demethylation reaction).

  1-methyl-1H-indol-7-ol (Journal of Medicinal Chemistry), 1992, Vol. 35, No. 1, 177- From 7-methoxy-1-methyl-1H-indole, which can be produced by the method described on page 184, Bioscience, Biotechnology, and Biochemistry 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction).

  1- (4-hydroxy-3-methylphenyl) ethanone O-methyloxime is, for example, commercially available 1- (4-hydroxy-3-methyl) Phenyl) ethanone (1- (4-hydroxy-3-methylphenyl) ethanone), according to the method described in Journal of the American Chemical Society, 1986, 108, 6016-6023 Can be manufactured.

  2-isopropenyl-6-methylphenol can be produced, for example, by the method described in Chemische Berichte, 1925, Vol. 58, p. 41. -3-methylphenyl) ethanone (1- (2-hydroxy-3-methylphenyl) ethanone), Organic Synthesis, Collective Volume, Volume 4, pages 836-838 ( Phenol to phenyl methyl ether, methylation reaction) and The Journal of Organic Chemistry, 1963, 28, 1128 or Synthetic Communications, 1985, 15 No. 10, pages 855-864 (conversion of carbonyl group to olefin, Wittig reaction), and bioscience biotechnology Biochemistry (Bioscience, Biotechnology, and Biochemistry), 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction) It can be manufactured similarly.

  1,1-dimethyl-5-indanol, for example, Bulletin of the Chemical Society of Japan, 2000, Vol. 73, No. 12, From 5-methoxy-1,1-dimethylindane, which can be produced by the method described on pages 2779-2782, Organic Synthesis, Collective Volume, 5th Volume, pages 412-414, and can be prepared according to the method described above (conversion of phenylmethyl ether to phenol, demethylation reaction)

  3-Bromo-6-cyclopropyl-2-methylphenol is more tetra-functional than commercially available 2-methyl-3-nitrophenol. The method described in Tetrahedron Letters, 1998, 39, 2947 (bromination of phenol), Organic Synthesis, Collective Volume, 4, 836-838 (Methods of conversion of phenol to phenyl methyl ether, methylation reaction) and modification of the method described in Organic Synthesis, Collective Volume, Vol. 1, pages 445-447 (Reduction reaction of nitrophenol to aniline; 8.5 equivalents of zinc powder and 25 equivalents of ammonium chloride to nitrophenol, reaction at room temperature) and Tetrahedron Letters (Tetrahedr on Letters), 2000, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), Organic Synthesis, Collective Volume, 3rd Vol., Methods described on pages 185-187 or The Journal of Organic Chemistry, 1977, vol. 42, pages 242-2430 (conversion of anilines to bromobenzene, Sandmeyer reaction, etc.) ) And the method described in Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (phenylmethyl ether to phenol) Conversion, demethylation reaction).

  6-Cyclopropyl-2-methyl-3-nitrophenol is more tetrahedral than 2-methyl-3-nitrophenol which is commercially available. The method described in Tetrahedron Letters, 1998, 39, 2947 (bromination of phenol), Organic Synthesis, Collective Volume, 4, 836-838 (Methods of conversion of phenol to phenyl methyl ether, methylation reaction) and modification of the method described in Organic Synthesis, Collective Volume, Vol. 1, pages 445-447 (Reduction reaction of nitrophenol to aniline; 8.5 equivalents of zinc powder and 25 equivalents of ammonium chloride to nitrophenol, reaction at room temperature) and Tetrahedron Letters (Tetrahedr on Letters), 2000, 41, 4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura coupling reaction), and bioscience, biotechnology and biochemistry (Bioscience, Biotechnology, and Biochemistry), 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (conversion of phenylmethyl ether to phenol, demethylation reaction) and tetrahedron, 1987 43, No. 8, pp. 1753-1758 (conversion of aniline derivative to nitrobenzene).

  5-methyl-1,3-dihydro-2-benzofuran-4-ol is an example of Journal of the American Chemical Society. American Chemical Society), 2000, vol. 122, pages 11553-11554.

  2-Fluoro-3,5,6-trimethylphenol is produced, for example, by the method described in Chemische Berichte, 1922, 55, 2384 From 2,3,5-trimethyl-6-nitrophenol (Organic Synthesis), Collective Volume, Vol. 4, pages 836-838 Or the method described in Liebigs Annalen der Chemie, 1957, 608, 128, or organic synthesis (Organic). Synthesis, Collective Volume, Volume 5, pages 829-833 (reduction reaction of nitro group to amino group), and Synthesis, 1989, pages 905-908 Method (fragrance (Conversion of amine to aromatic fluoride) and the method described in Organic Synthesis, Collective Volume, Vol. 5, pp. 412-414 (conversion, dehydration of phenylmethyl ether to phenol) (Methylation reaction).

  2-chloro-3,5,6-trimethylphenol (2-chloro-3,5,6-trimethylphenol) is, for example, from commercially available 2,3,5-trimethylphenol (2,3,5-trimethylphenol) According to a modification of the method described in Tetrahedron Letters, 1998, Vol. 39, p. 2947 (chlorination reaction of phenol; using N-chlorosuccinimide instead of N-bromosuccinimide) Can be manufactured.

  2-iodo-3,5,6-trimethylphenol (2-iodo-3,5,6-trimethylphenol) is, for example, from commercially available 2,3,5-trimethylphenol (2,3,5-trimethylphenol), According to a modification of the method described in Tetrahedron Letters, 1998, Vol. 39, page 2947 (iodination reaction of phenol; using N-iodosuccinimide instead of N-bromosuccinimide) Can be manufactured.

  2-ethyl-3,5,6-trimethylphenol is an example of chemical research in toxicology, 1997, Vol. 10, No. 3, 335. From 1- (2-hydroxy-3,4,6-trimethylphenyl) ethanone, which can be produced by the method described on page 343. It can be synthesized according to the method described in Journal of the American Chemical Society, 1946, vol. 68, page 2487 (reduction reaction of carbonyl group Wolff-Kishner reduction reaction).

  2-isopropenyl-3,5,6-trimethylphenol (Chemical Research in Toxicology), 1997, Vol. 10, No. 3, Organic synthesis from 1- (2-hydroxy-3,4,6-trimethylphenyl) ethanone that can be produced by the method described on pages 335-343 (Organic Synthesis), Collective Volume, Volume 4, pages 836-838 (conversion of phenol to phenyl methyl ether, methylation reaction), and The Journal of Organic Chemistry (The Journal of Organic Chemistry) Organic Chemistry), 1963, 28, 1128 or Synthetic Communications, 1985, 15, 10, 855-864 (conversion of carbonyl group to olefin, Wittig reaction) and the method described in Bioscience, Biotechnology, and Biochemistry, 1993, Vol. 57, No. 9, pages 1572-1574 or JP-A-11-322755 (Conversion to phenol, demethylation reaction).

  1- (2-hydroxy-3,4,6-trimethylphenyl) ethanone (1- (2-hydroxy-3,4,6-trimethylphenyl) ethanone) is, for example, Chemical Research in Toxicology, 1997, Vol. 10, No. 3, pages 335-343.

  2,3,5-trimethyl-6-nitrophenol is produced by the method described in Chemische Berichte, 1922, 55, 2384, for example. it can.

  2,4-dichloro-3,5,6-trimethylphenol (2,4-dichloro-3,5,6-trimethylphenol) is, for example, commercially available 2,3,5-trimethylphenol (2,3,5-trimethylphenol). trimethylphenol), a modification of the method described in Tetrahedron Letters, 1998, 39, 2947 (phenol chlorination reaction; N-chlorosuccinimide instead of N-bromosuccinimide) Use).

  Pentamethylphenol can be produced, for example, by the method described in Journal of the Chemical Society, 1949, page 624.

  2,3,5,6-tetramethylphenol (2,3,5,6-tetramethylphenol) is, for example, a tetrahedron from commercially available 2,3,5-trimethylphenol (2,3,5-trimethylphenol). It can be produced by the method described in Letters (Tetrahedron Letters), 1989, volume 30, page 5215.

  After completion of each reaction step, the target compound in each step can be collected from the reaction mixture according to a conventional method. For example, it can be obtained by neutralizing the reaction mixture as appropriate, or by removing insoluble matters by filtration, adding an organic solvent immiscible with water, washing with water, and distilling off the solvent. If necessary, the obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation or chromatography.

  The compound (I) of the present invention can be converted into a salt. These salts are included in the present invention as long as they can be used as herbicides for agriculture and horticulture.

  Salts of the compound (I) of the present invention include, for example, alkali metal salts such as lithium, sodium and potassium; alkaline earth metal salts such as magnesium and calcium; aluminum salts; transition metal salts such as iron and copper; ammonium and trimethylammonium Amine salts such as triethylammonium, tetramethylammonium and pyridinium; inorganic mineral salts such as hydrochloride, sulfate and phosphate; or organic acid salts such as formate, acetate, toluenesulfonate and oxalate It can be.

  When the pyridazine derivative becomes the acid component of the salt, the salt can be produced, for example, by mixing the pyridazine derivative and a base in the presence or absence of a solvent and distilling off the solvent.

  The base to be used is not particularly limited as long as it is a base exhibiting a pH of 8 or higher. Examples thereof include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; sodium carbonate, potassium carbonate and cesium carbonate. Alkali metal carbonates; metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide; alkali metal salts of organic acids such as sodium acetate, potassium acetate, sodium formate, potassium formate; sodium hydride, hydrogenation Alkali metal hydrides such as potassium; alkali metals such as sodium and potassium; aliphatic tertiary amines such as triethylamine, tributylamine and diisopropylethylamine; 1,4-diazabicyclo [2.2.2] octane (DABCO) ), 1,8-diazabicyclo 5.4.0] Aliphatic cyclic tertiary amines such as undec-7-ene (DBU); pyridines such as pyridine, collidine, 4- (N, N-dimethylamino) pyridine; lithium amide, sodium Metal amides such as amides; or organometallic bases such as butyl lithium, s-butyl lithium, lithium diisopropylamide, sodium bis (trimethylsilyl) amide, lithium bis (trimethylsilyl) amide.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, water; alcohols such as methanol, ethanol, t-butanol; acetone, methyl isobutyl ketone Ketones such as acetonitrile; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; ethers such as diethyl ether, tetrahydrofuran and dioxane; Aromatic hydrocarbons such as; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; or a mixed solvent thereof.

  When the pyridazine derivative becomes the base component of the salt, the salt can be produced, for example, by mixing the pyridazine derivative and an acid in the presence or absence of a solvent and distilling off the solvent.

  The acid to be used is not particularly limited as long as it is an acid having a pH of 6 or less, for example, inorganic mineral acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid; or formic acid, acetic acid, toluene It can be an organic acid such as sulfonic acid, succinic acid, benzoic acid.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. For example, water; alcohols such as methanol, ethanol, t-butanol; acetone, methyl isobutyl ketone Ketones such as acetonitrile; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; ethers such as diethyl ether, tetrahydrofuran and dioxane; Aromatic hydrocarbons such as; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; or a mixed solvent thereof.

The composition of the present invention is a variety of weeds that are problematic in paddy fields, for example, grasses such as Tainubie; broad-leaved weeds such as Azena, Azepera, Kakashigusa, Mizojakobe, Abnome, Himeisohagi, Konagi; It shows herbicidal activity against crustaceae weeds such as Spodoptera litura and Shizui;
The composition of the present invention can be used not only in paddy fields, but also in fields, orchards, mulberry fields and non-agricultural lands.

  The synergistic effect of the present invention is recognized in a wide range of mixing ratios, and compound (B) and compound (C) are usually mixed at a ratio of 0.01 to 100 parts by mass with respect to 1 part by mass of compound (I). A useful herbicide can be prepared, and the mixing ratio is preferably 0.1 to 10 parts by mass, and more preferably 0.2 to 5 parts by mass. The herbicide of the present invention thus completed can obtain a high herbicidal effect by soil treatment or foliage treatment before and after germination of weeds.

  In the present invention, the 3-phenoxy-4-pyridazinol derivative and the compound (B) and the compound (C) may be mixed and sprayed as one preparation, or both active ingredients may be sprayed simultaneously without mixing. One active ingredient may be sprayed first, and the other active ingredient may be sprayed later. Moreover, the order of spreading is arbitrary.

  The composition of the present invention may be sprayed with the active ingredient itself, or mixed with a carrier and other auxiliary agents as necessary, and is usually used as a herbicide, for example, a powder, a coarse powder, a fine granule, It is prepared and used in granules, wettable powders, emulsions, aqueous suspensions, granular wettable powders, oil suspensions, paddy throwers and the like. As used herein, a carrier refers to a synthetic or natural inorganic or organic substance mixed in a herbicide to help reach the plant of an active ingredient compound or to facilitate storage, transportation or handling of the active ingredient. means.

  Suitable solid carriers include, for example, clays represented by the kaolinite group, montmorillonite group, attapulgite group, etc .; talc, mica, phyllite, pumice, vermiculite, gypsum, dolomite, diatomaceous earth, magnesium lime, phosphorus lime , Zeolite, anhydrous silicic acid, synthetic calcium silicate, kaolin, bentonite, calcium carbonate and other inorganic substances; soy flour, tobacco powder, walnut powder, wheat flour, wood flour, starch, crystalline cellulose, and other plant organic substances; coumarone resin , Petroleum resins, alkyd resins, polyvinyl chloride, polyalkylene glycols, ketone resins, ester gums, copal gums, dammar gums, and other synthetic or natural polymer compounds; waxes such as carnauba wax, paraffin wax, beeswax; or urea possible.

  Suitable liquid carriers are, for example, paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil, white oil; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene, methylnaphthalene; carbon tetrachloride, Chlorinated hydrocarbons such as chloroform, trichloroethylene, monochlorobenzene, chlorotoluene; ethers such as dioxane and tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, and isophorone; ethyl acetate, amyl acetate, ethylene glycol Esters such as acetate, diethylene glycol acetate, dibutyl maleate and diethyl succinate; methanol, hexanol, ethylene glycol, diethylene glycol, Rohekisanoru, alcohols such as benzyl alcohol, ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether, ether alcohols such as diethylene glycol butyl ether; dimethylformamide, polar solvents such as dimethyl sulfoxide; or, may be water.

  Surfactants used for emulsification, dispersion, wetting, spreading, bonding, disintegration control, active ingredient stabilization, fluidity improvement, rust prevention, plant absorption promotion, etc. are ionic or nonionic But you can.

  Suitable nonionic surfactants include, for example, fatty acid sucrose esters, lauryl alcohol, stearyl alcohol, ethylene oxide polymerization adducts of higher aliphatic alcohols such as oleyl alcohol, and ethylene oxide polymerization of alkylphenols such as isooctylphenol and nonylphenol. Oxidized ethylene polymerized adducts of adducts, alkyl naphthols such as butyl naphthol and octyl naphthol, oxidized ethylene polymerized adducts of higher fatty acids such as palmitic acid, stearic acid and oleic acid, and oxidation of mono- or dialkyl phosphoric acids such as stearyl phosphate dilauryl phosphate Ethylene polymerized adducts, ethylene oxide polymerized adducts of higher aliphatic amines such as dodecylamine and stearamide, higher fatty acid esters of polyhydric alcohols such as sorbitan and ethylene oxide polymerized adducts thereof And it can be exemplified copolymers of ethylene oxide and propylene oxide.

  Suitable anionic surfactants include, for example, alkyl sulfate salts such as sodium lauryl sulfate and oleyl alcohol sulfate amine salt, fatty acid salts such as sodium dioctyl sulfosuccinate, sodium oleate and sodium stearate, isopropyl naphthalene, and the like. Examples thereof include alkylaryl sulfonates such as sodium sulfonate, sodium methylenebisnaphthalene sulfonate, sodium lignin sulfonate, and sodium dodecylbenzene sulfonate.

  Examples of suitable cationic surfactants include higher aliphatic amines, quaternary ammonium salts, alkylpyridinium salts, and the like.

  Furthermore, the herbicide of the present invention has other components such as gelatin, gum arabic, casein, albumin, glue, sodium alginate, polyvinyl alcohol, carboxymethylcellulose, for the purpose of improving the properties of the preparation and enhancing the biological effect. Polymer compounds such as methylcellulose and hydroxymethylcellulose, thixotropic agents such as sodium polyphosphate and bentonite, and other auxiliary agents can also be contained.

  For example, powders and coarse powders usually contain 0.1 to 25 parts by mass of an active ingredient, and the balance is a solid carrier.

  The wettable powder and the granular wettable powder, for example, usually contain 1 to 90 parts by mass of the active ingredient, and the balance is a solid carrier and a dispersion wetting agent. If necessary, a protective colloid, a thixotropic agent and an antifoaming agent. Is added. These preparations are suspended and dispersed in water when stirred in water.

  Granules and fine granules contain, for example, usually 0.1 to 35 parts by mass of an active ingredient, and the remainder is mostly a solid carrier. The active ingredient compound is uniformly mixed with the solid carrier, or is fixed or adsorbed uniformly on the surface of the solid carrier, and the particle diameter is usually 0.2 to 1.5 mm.

  The emulsion usually contains, for example, 1 to 70 parts by mass of the active ingredient compound, which contains 5 to 20 parts by mass of an emulsifier, and the remainder is a liquid carrier, and other components such as a rust inhibitor as required. Of supplements are added.

  An aqueous suspension or oil suspension is a suspension or emulsification dispersion of an active ingredient in water or an organic solvent with a high boiling point using an appropriate surfactant. To maintain stability over time.

  The paddy throwing agent is an active ingredient formulated into an appropriate dosage form such as powder, granule, tablet, emulsion, bulk tablet, etc., and if necessary, these are packaged in a water-soluble film or container. In use, several to several hundreds of these are used as they are in the paddy field.

  When the composition of the present invention thus prepared in various dosage forms is treated with soil before or after germination of weeds in paddy fields, for example, 1 g to 1000 g, preferably 10 g to 300 g as an active ingredient per 10a. By treating the weeds, weeds can be effectively controlled.

  As a method for treating the composition of the present invention, it can be usually formulated and treated with soil, foliage or flooding before germination of weeds or within about one month after emergence. Soil treatment includes soil surface treatment, soil admixing treatment, etc., and foliage treatment includes treatment from the top of the plant body, extreme treatment that treats only weeds so as not to adhere to crops, The flooding treatment includes spraying of granules and flowables and irrigation treatment on the water surface.

  Other herbicides can be blended with the herbicide of the present invention in order to broaden the herbicidal spectrum.

  The herbicide of the present invention can be used by mixing with, for example, plant growth regulators, fungicides, insecticides, acaricides, nematicides or fertilizers.

  Hereinafter, the present invention will be specifically described with reference to formulation examples and test examples, but the present invention is not limited thereto. In the following formulation examples, “%” indicates mass%.

Example 1
6-Chloro-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 128)
(1) 3-Chloro-6- (2-methylphenoxy) pyridazine (Step A-1)
A mixture of 278.7 g (1.87 mol) of 3,6-dichloropyridazine, 202.3 g (1.87 mol) of 2-methylphenol and 259 g (1.87 mol) of potassium carbonate was heated and stirred at 160 ° C. for 6 hours. The reaction mixture was cooled to 70 ° C. and 2 L of ethyl acetate was added. The mixture was washed successively with 1 mol / L aqueous sodium hydroxide solution (4 × 500 mL), water (4 × 500 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate. The solvent was distilled off, and isopropyl ether was added to the residue for crystallization. Crystals were collected by filtration to obtain 234.2 g (1.06 mol, yield 56.7%) of 3-chloro-6- (2-methylphenoxy) pyridazine.
(2) 4,6-Dichloro-3- (2-methylphenoxy) pyridazine (Step A-2)
3-Chloro-6- (2-methylphenoxy) pyridazine (234.2 g, 1.06 mol) obtained in (1) was dissolved in phosphorus oxychloride (1.85 L), and 76.7 g (1.08 mol) of chlorine gas was added to this solution. Was blown in over 4 hours. Nitrogen gas was blown into the reaction mixture to remove excess chlorine gas, and then phosphorus oxychloride was distilled off. The residue was dissolved in ethyl acetate (1.5 L), washed successively with water (4 × 500 mL) and saturated brine (200 mL), and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was washed with 500 mL of hexane to obtain 193.1 g of a crude product. This crude product was recrystallized from a mixed solvent of hexane-ethyl acetate (400 mL-240 mL) to obtain 114.4 g (0.448 mol, yield 42.3%) of 4,6-dichloro-3- (2-methylphenoxy) pyridazine. It was.
(3) 6-chloro-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 128, Step A-3)
100.0 g (0.392 mol) of 4,6-dichloro-3- (2-methylphenoxy) pyridazine obtained by (2) was dissolved in 1,4-dioxane (1 L), and sodium hydroxide (purity 96 %, 19.6 g, 0.470 mol) aqueous solution (water 400 mL) and tetrabutylammonium chloride 1.09 g (4.78 mmol) were added and heated to reflux for 4 hours. The reaction mixture was concentrated under reduced pressure to a total volume of about 100 mL. To this residue was added an aqueous sodium hydroxide solution (dissolved in 13.1 g of sodium hydroxide in 1.4 L of water) and 500 mL of ethyl acetate. The aqueous layer was washed with ethyl acetate (3 × 200 mL), and adjusted to pH 5 by adding concentrated hydrochloric acid under ice cooling. The precipitated solid was collected by suction filtration, washed with 1 L of water, and air-dried. The obtained solid was recrystallized from acetonitrile to obtain 34.4 g (0.145 mol, yield 37.0%) of 6-chloro-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 128). The organic layer was dried over magnesium sulfate and the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (YMC GEL, SIL60, 350 / 250mesh, hexane-ethyl acetate, gradient), and 13.5 g of 6-chloro-3,4-bis (2-methylphenoxy) pyridazine was obtained. (0.0414 mol, yield 10.5%).
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.35-7.08 (4H, m), 6.84 (1H, br.s), 2.11 (3H, s).
Melting point (° C): 211-213.

(Example 2)
3- (2-Methylphenoxy) -4-pyridazinol (Compound No. 5)
(1) 6-chloro-4-methoxy-3- (2-methylphenoxy) pyridazine (Step A-3)
3.00 g (11.8 mmol) of 4,6-dichloro-3- (2-methylphenoxy) pyridazine obtained in Example 1 (2) was dissolved in methanol (60 mL), and 95% sodium methoxide 1.00 was added to this solution at room temperature. g (17.6 mmol) was added and stirred at 60 ° C. for 4 hours. Further, 1.00 g (17.6 mmol) of 95% sodium methoxide was added and stirred at 60 ° C. for 1 hour, and then left overnight at room temperature. The reaction mixture was concentrated, ethyl acetate was added to the residue, and the mixture was washed successively with water and saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (eluted with hexane: ethyl acetate = 4: 1) to give 6-chloro-4-methoxy-3- ( 2.75 g (11.0 mmol, yield 93.2%) of 2-methylphenoxy) pyridazine was obtained.
(2) 4-Methoxy-3- (2-methylphenoxy) pyridazine (Step N-1)
Dissolve 2.00 g (7.98 mmol) of 6-chloro-4-methoxy-3- (2-methylphenoxy) pyridazine obtained in (1) in methanol (40 mL), and add 0.20 g of 5% palladium-carbon to this solution. The mixture was stirred for 4 hours under a hydrogen atmosphere (1 atm). The reaction mixture was filtered through celite and the filtrate was concentrated. The residue was purified by silica gel column chromatography (eluted with ethyl acetate and then dichloromethane: methanol = 5: 1), and 1.59 g (7.36 mmol, yield 92.2%) of 4-methoxy-3- (2-methylphenoxy) pyridazine Obtained.
(3) 3- (2-Methylphenoxy) -4-pyridazinol (Compound No. 5, Step N-2)
1.08 g (5.00 mmol) of 4-methoxy-3- (2-methylphenoxy) pyridazine obtained by (2), 0.24 g (6.0 mmol) of sodium hydroxide, water (5 mL) and 1,4-dioxane (5 mL) ) Was stirred overnight. The reaction mixture was washed with ethyl acetate, the aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The solvent was distilled off to obtain 0.21 g (10 mmol, yield 20%) of 3- (2-methylphenoxy) -4-pyridazinol (Compound No. 5).
¹ H-NMR (60MHz, DMF-d ₇ ) δppm: 8.30 (1H, d, J = 7.2Hz), 7.43-7.00 (5H, m), 6.43 (1H, d, J = 7.2Hz), 2.18 (3H , s).
Melting point (° C): 169-171.

(Example 3)
5-Chloro-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 45)
(1) 4,5-dichloro-3- (2-methylphenoxy) pyridazine
3- (2-Methylphenoxy) pyridazine {Agricultural and Biological Chemistry, 1968, 32, 1376 and Agricultural and Biological Chemistry, 1969, 33 Can be produced by the method described on page 96. } 16.4 g (88.2 mmol) and phosphorus oxychloride (200 mL) were mixed and the mixture was heated to 80 ° C. and 8.5 g (120 mmol) of chlorine gas was introduced. Phosphorus oxychloride was distilled off from the reaction mixture, and the residue was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Merck, 9385, hexane: ethyl acetate gradient) to give 6.61 g (25.9) of 4,5-dichloro-3- (2-methylphenoxy) pyridazine. Mmol, 29.4% yield), 8.14 g (36.9 mmol, 41.8% yield) 5-chloro-3- (2-methylphenoxy) pyridazine and 1.20 g 4-chloro-3- (2-methylphenoxy) pyridazine (5.44 mmol, yield 6.17%) was obtained.
(2) 5-chloro-4-methoxy-3- (2-methylphenoxy) pyridazine (Step A-3)
4.10 g (20.0 mmol) of 4,5-dichloro-3- (2-methylphenoxy) pyridazine obtained by (1) and methanol (70 mL) were mixed, and 0.46 g (20 mmol of sodium) was added to this mixture at -8 ° C. ) And stirred at −8 ° C. for 30 minutes and under ice cooling for 8 hours 30 minutes. Ice-cold water was added to the reaction mixture, and the mixture was adjusted to pH 3 with hydrochloric acid and extracted with ethyl acetate. The organic layers were combined, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Merck, 9385, hexane: ethyl acetate gradient) to obtain 1.15 g of 5-chloro-4-methoxy-3- (2-methylphenoxy) pyridazine. (4.58 mmol, yield 22.9%) and 4.27 g (13.0 mmol, yield 65%) of 4-chloro-5-methoxy-3- (2-methylphenoxy) pyridazine were obtained.
(3) 5-chloro-3- (2-methylphenoxy) -4-pyridazinol (compound number 45, step A-4, etc.)
750 mg (2.99 mmol) of 5-chloro-4-methoxy-3- (2-methylphenoxy) pyridazine obtained by (2), 156 mg (3.9 mmol) of sodium hydroxide, 1,4-dioxane (5 mL) and water ( 10 mL) and the mixture was heated to reflux with stirring for 2 hours 30 minutes. The reaction mixture was poured into ice-cold water and acidified with hydrochloric acid. The precipitated solid was collected by filtration and washed with water and then hexane. 525 mg (2.22 mmol, yield 74.2%) of 5-chloro-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 45) was obtained.
¹ H-NMR (60 MHz, DMF-d ₇ ) δ ppm: 8.68 (1H, s), 7.38-6.80 (4H, m), 5.32 (1H, br.s), 2.13 (3H, s).
Melting point (° C): 238-243.

Example 4
5-chloro-3- (2-methylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 66, Step I-1)
5-Chloro-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 45) 237 mg (1.00 mmol) obtained in Example 3 and acetonitrile (8 mL) were mixed, and this mixture was stirred under 1, 4-Diazabicyclo [2.2.2] octane 112 mg (1.00 mmol) was added, then 4-methylbenzenesulfonyl chloride 191 mg (1.00 mmol) was added, and the mixture was stirred at room temperature for 1 hour 30 minutes. Water was added to the reaction mixture, acidified with hydrochloric acid, and extracted with ethyl acetate. The organic layers were combined, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane: ethyl acetate = 3: 1) to give 5-chloro-3- (2-methylphenoxy) -4-pyridazinyl 4- 379 mg (0.969 mmol, yield 96.9%) of methylbenzenesulfonate (Compound No. 66) was obtained.
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 8.80 (1H, s), 7.77-6.75 (8H, m), 2.47 (3H, s), 1.98 (3H, s).
Melting point (° C): 140-143.

(Example 5)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinol 1-oxide (Compound No. 129, Step F-1)
135 mg (0.572 mmol) of 6-chloro-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 128) obtained according to Example 1 and methylene chloride (6 mL) were mixed, and this mixture was mixed with m-chloro 247 mg of perbenzoic acid (purity 80%, 1.14 mmol) was added, and the mixture was stirred with heating under reflux for 16 hours. After standing at room temperature for 2 days, the reaction mixture was poured into a saturated aqueous sodium sulfite solution and washed with methylene chloride. The aqueous layer was acidified with hydrochloric acid, extracted with methylene chloride, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (eluting with YMC GEL, SIL60, 350 / 250mesh, ethyl acetate) to give 6-chloro-3- (2-methylphenoxy) -4- 32.6 mg (0.129 mmol, yield 22.6%) of pyridazinol 1-oxide (Compound No. 129) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.34 (1H, s), 7.34-7.10 (4H, m), 2.20 (3H, s).
Melting point (° C): 194-196.

(Example 6)
6-Chloro-3- (2-cyclopropylphenoxy) -4-pyridazinol (Compound No. 139)
(1) Mixture of 6-chloro-3- (2-cyclopropylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-cyclopropylphenoxy) pyridazine 1-oxide (step B-2)
25.3 g (189 mmol) of 2-cyclopropylphenol, 1,4-dioxane (120 mL) and dimethyl sulfoxide (120 mL) were mixed, and 23.2 g (207 mmol) of potassium tert-butoxide was added to this mixture under ice cooling. Stir for 10 minutes. To this mixture, 32.0 g (194 mmol) of 3,6-dichloropyridazine 1-oxide, which is a known compound, was added and left at room temperature for 5 days. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate, gradient) to give 6-chloro-3- (2-cyclopropylphenoxy) pyridazine 1-oxide and 3-chloro-6- ( 43.3 g (165 mmol, yield 87.3%) of a mixture of 2-cyclopropylphenoxy) pyridazine 1-oxide was obtained.
(2) 4,6-Dichloro-3- (2-cyclopropylphenoxy) pyridazine (Step B-3)
43.3 g (165 mmol) of a mixture of 6-chloro-3- (2-cyclopropylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-cyclopropylphenoxy) pyridazine 1-oxide obtained by (1) , Chloroform (30 mL) and phosphorus oxychloride 18.0 mL (194 mmol) were mixed and the mixture was heated to 60 ° C. to dissolve. This was stirred at room temperature overnight and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate, gradient) to obtain 32.5 g (116 mmol, yield 70.3%) of 4,6-dichloro-3- (2-cyclopropylphenoxy) pyridazine.
(3) 6-chloro-3- (2-cyclopropylphenoxy) -4-pyridazinol (Compound No. 139, Step B-4)
Dissolve 3,2.5 g (116 mmol) of 4,6-dichloro-3- (2-cyclopropylphenoxy) pyridazine obtained in (2) in dimethyl sulfoxide (500 mL) and add 84 mL of 10% (W / V) aqueous sodium hydroxide solution. (210 mmol) was added and stirred at room temperature overnight. The reaction mixture was poured into ice-cold 1 mol / L aqueous sodium hydroxide and washed with ether. The aqueous layer was acidified with hydrochloric acid, and the precipitated solid was collected by filtration and washed with water. Acetonitrile was added to the resulting solid and heated. Allowed to cool overnight and the crystals were collected by filtration (14.04 g). The filtrate was concentrated and the residue was recrystallized from ethanol to obtain 2.64 g of crystals. These crystals were combined to obtain 16.7 g (63.5 mmol, yield 54.7%) of 6-chloro-3- (2-cyclopropylphenoxy) -4-pyridazinol (Compound No. 139).
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ: 7.28-6.97 (4H, m), 6.82 (1H, s), 1.89-1.77 (1H, m), 0.87-0.73 (2H, m), 0.73- 0.58 (2H, m).
Melting point (° C): 229-231.

(Example 7)
6-Chloro-3- [2- (1-fluorocyclopropyl) phenoxy] -4-pyridazinol (Compound No. 140)
(1) 2- (Methoxymethoxy) benzaldehyde Commercial salicylaldehyde (5.01 g, 41.1 mmol) was dissolved in N, N-dimethylformamide (20 mL), and this solution was dissolved in ice-cooled 60% sodium hydride (1.80 g, 45.0 mmol). After stirring for 10 minutes under ice cooling, 3.43 mL (45.2 mmol) of chloro (methoxy) methane was slowly added dropwise and stirred for 1 hour under ice cooling. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 6.54 g (39.4 mmol, yield 95.9) of 2- (methoxymethoxy) benzaldehyde. %)Obtained.
(2) 1- (methoxymethoxy) -2-vinylbenzene In a nitrogen atmosphere, 877 mg (21.9 mmol) of 60% sodium hydride washed with hexane was suspended in dry dimethyl sulfoxide (10 mL). After stirring with heating at 85 ° C. for 30 minutes, the solution was returned to room temperature and further a solution of 7.83 g (21.9 mmol) of methyl (triphenyl) phosphonium bromide in dry dimethyl sulfoxide (20 mL) was slowly added dropwise under ice cooling. After stirring at room temperature for 15 minutes, a solution of 3.02 g (18.2 mmol) of 2- (methoxymethoxy) benzaldehyde obtained in (1) in dry dimethyl sulfoxide (9 mL) was added dropwise and stirred at room temperature for 15 minutes. The reaction mixture was poured into water and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 2.54 g (15.5 mmol) of 1- (methoxymethoxy) -2-vinylbenzene. Yield 85.2%).
(3) 1- (2-Bromo-1-fluoroethyl) -2- (methoxymethoxy) benzene
N, N, N-triethylamine Hydrofluoric acid (MEC-82) 1.47 g (9.13 mmol) in methylene chloride (10 mL) was added to 1- (methoxymethoxy) -2-vinylbenzene obtained in (2). A solution of 1.00 g (6.09 mmol) of methylene chloride (5 mL) was added dropwise, and 1.19 g (6.70 mmol) of N-bromosuccinimide was added under ice cooling. After stirring for 2 hours under ice cooling, the mixture was warmed to room temperature and further stirred for 30 minutes. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with methylene chloride. The organic layer was washed successively with dilute hydrochloric acid, water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was subjected to preparative thin layer chromatography (development with 4: 1 MERCK 1.05717 ethyl acetate: hexane = 4: 1), and then preparative thin layer chromatography (MERCK) 1.05744 4 sheets were used and developed with ethyl acetate: hexane = 10: 1) to obtain 1.24 g of a crude product of 1- (2-bromo-1-fluoroethyl) -2- (methoxymethoxy) benzene.
(4) 1- (1-Fluorovinyl) -2- (methoxymethoxy) benzene 736.2 mg (11.15 mmol) of 85% potassium hydroxide was added to dry dimethyl sulfoxide (10 mL), and the mixture was stirred at room temperature for 1 hour and 30 minutes. A solution of 978.2 mg of the crude product of 1- (2-bromo-1-fluoroethyl) -2- (methoxymethoxy) benzene obtained in) was added dropwise and stirred for 2 hours, and then stirred for 60 hours. The mixture was stirred with heating at ° C for 2 hours. The reaction mixture was poured into water and extracted with hexane. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 632.7 mg of a crude product of 1- (1-fluorovinyl) -2- (methoxymethoxy) benzene.
(5) 1- (1-Fluorocyclopropyl) -2- (methoxymethoxy) benzene In a nitrogen atmosphere, put dry diethyl ether (5 mL) into a dry flask, and add 1.97 mL (1.97 mmol) of diethylzinc (1M hexane solution). Then, a solution of 143.6 mg of the crude product of 1- (1-fluorovinyl) -2- (methoxymethoxy) benzene obtained in (4) in dry diethyl ether (3 mL) was added dropwise. After stirring at room temperature for 10 minutes, 0.19 mL (2.3 mmol) of diiodomethane was added dropwise, and the mixture was heated to reflux for 4 hours and 30 minutes. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was stirred for a while and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed with ethyl acetate: hexane = 4: 1), and 1- (1- 80.5 mg of a crude product of fluorocyclopropyl) -2- (methoxymethoxy) benzene was obtained.
(6) 2- (1-Fluorocyclopropyl) phenol The crude product of 1- (1-fluorocyclopropyl) -2- (methoxymethoxy) benzene obtained by (5) was added to a solution of 43.8 mg of methanol (6 mL). Concentrated hydrochloric acid (0.3 mL) was added dropwise, and the mixture was stirred with heating at 60 ° C. for 3 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 42.8 mg of a crude product of 2- (1-fluorocyclopropyl) phenol.
(7) 6-chloro-3- [2- (1-fluorocyclopropyl) phenoxy] pyridazine 1-oxide (step B-2)
42.8 mg of the crude product of 2- (1-fluorocyclopropyl) phenol obtained in (6) was dissolved in a mixed solvent of 1,4-dioxane (3 mL) and dimethyl sulfoxide (3 mL). -Butoxide 34.7 mg (0.310 mmol) was added, followed by 3,6-dichloropyridazine 1-oxide 46.4 mg (0.281 mmol) and stirred at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 2 plates used, developed with ethyl acetate: hexane = 2: 1), and 6-chloro-3 28.0 mg (0.0996 mmol) of-[2- (1-fluorocyclopropyl) phenoxy] pyridazine 1-oxide was obtained.
(8) 4,6-Dichloro-3- [2- (1-fluorocyclopropyl) phenoxy] pyridazine (Step B-3)
6-Chloro-3- [2- (1-fluorocyclopropyl) phenoxy] pyridazine 1-oxide 28.0 mg (0.0996 mmol) obtained in (7) was dissolved in phosphorus oxychloride (1 mL), and this solution was dissolved at room temperature. Stir overnight. Water and methylene chloride were added to the reaction solution, and the mixture was stirred for 30 minutes and extracted with methylene chloride. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (MERCK, 1.05744, used in 2 plates, developed with ethyl acetate: hexane = 2: 1), and 4,6-dichloro There was obtained 5.1 mg (0.017 mmol, 17% yield) of -3- [2- (1-fluorocyclopropyl) phenoxy] pyridazine.
(9) 6-Chloro-3- [2- (1-fluorocyclopropyl) phenoxy] -4-pyridazinol (Compound No. 140, Step B-4)
5.1 mg (0.017 mmol) of 4,6-dichloro-3- [2- (1-fluorocyclopropyl) phenoxy] pyridazine obtained by (8) was added to 1,4-dioxane (2 mL) and dimethyl sulfoxide (2 mL). This was dissolved in a mixed solvent, and 0.1 mL of a 2 mol / L aqueous sodium hydroxide solution was added to the solution, followed by stirring overnight at room temperature. The reaction mixture was poured into water, adjusted to pH 2 with dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (MERCK, 1.05744, 1 plate used, developed with ethyl acetate), and 6-chloro-3- [2- (1 There was obtained 4.0 mg (0.014 mmol, yield 82%) of -fluorocyclopropyl) phenoxy] -4-pyridazinol (Compound No. 140).
¹ H-NMR (200MHz, CD ₃ OD) δppm: 7.57-7.52 (1H, m), 7.39-7.31 (1H, m), 7.22-7.13 (1H, m), 7.00 (1H, d, J = 8.1Hz ), 6.48 (1H, s), 1.32-1.22 (2H, m), 1.16-1.08 (2H, m).
Melting point (° C): 152-157.

(Example 8)
6-Chloro-3- {2- [1- (ethylsulfanyl) cyclopropyl] phenoxy} -4-pyridazinol (Compound No. 207)
(1) 1-Methoxy-2-vinylbenzene Under a nitrogen atmosphere, 1.92 g (48.0 mmol) of 60% sodium hydride washed with hexane was suspended in dry dimethyl sulfoxide (15 mL). After heating and stirring for 30 minutes, the solution was returned to room temperature, and a solution of 17.2 g (48.2 mmol) of methyl (triphenyl) phosphonium bromide in dry dimethyl sulfoxide (35 mL) was slowly added dropwise under ice cooling. After stirring at room temperature for 20 minutes, 4.83 mL (40.1 mmol) of commercially available 2-methoxybenzaldehyde was added dropwise, stirred at room temperature for 1 hour, and then stirred at 65 ° C. for 3 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 3.29 g (24.5 mmol, yield) of 1-methoxy-2-vinylbenzene. 61.1%).
(2) 1- (2-Bromo-1-fluoroethyl) -2-methoxybenzene
To a solution of 3.60 g (22.4 mmol) of N, N, N-triethylamine hydrofluoric acid (MEC-82) in methylene chloride (20 mL) was added 2.01 g of 1-methoxy-2-vinylbenzene obtained in (1) ( A solution of 15.0 mmol) in methylene chloride (6 mL) was added dropwise, and 2.92 g (16.4 mmol) of N-bromosuccinimide was added under ice cooling. After stirring for 25 minutes under ice cooling, the mixture was warmed to room temperature and further stirred for 1 hour 30 minutes. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with methylene chloride. The organic layer was washed successively with dilute hydrochloric acid, water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 1- (2-bromo-1-fluoroethyl) -2-methoxybenzene. 1.39 g of crude product of was obtained.
(3) 1- (1-fluorovinyl) -2-methoxybenzene 1.28 g (19.4 mmol) of 85% potassium hydroxide was added to dry dimethyl sulfoxide (10 mL), and the mixture was stirred at room temperature for 30 minutes. A solution of 1.50 g of a crude product of 1- (2-bromo-1-fluoroethyl) -2-methoxybenzene in dry dimethyl sulfoxide (10 mL) was added dropwise and stirred overnight. The reaction mixture was poured into water and extracted with hexane. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give a crude product of 1- (1-fluorovinyl) -2-methoxybenzene. 1.21 g was obtained.
(4) 1- (1-Fluorocyclopropyl) -2-methoxybenzene In a nitrogen atmosphere, dry diethyl ether (8 mL) is placed in a dry flask and 19.88 mL (19.88 mmol) of diethyl zinc (1 mol / L hexane solution) is added dropwise. Then, a solution of 1.21 g of the crude product of 1- (1-fluorovinyl) -2-methoxybenzene obtained in (3) in dry diethyl ether (8 mL) was added dropwise. After stirring at room temperature for 10 minutes, 1.92 mL (23.86 mmol) of diiodomethane was added dropwise and heated to reflux for 6 hours. After standing overnight at room temperature, the reaction mixture was poured into saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was stirred for a while and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to produce crude 1- (1-fluorocyclopropyl) -2-methoxybenzene. 1.06 g of product was obtained.
(5) 2- [1- (Ethylsulfanyl) cyclopropyl] phenol Under nitrogen atmosphere, 765.3 mg (19.1 mmol) of 60% sodium hydride was suspended in dry N, N-dimethylformamide (8 mL). 1.46 mL (19.8 mmol) of ethanethiol was slowly added dropwise thereto and stirred for 15 minutes, and then 1.06 g of a crude product of 1- (1-fluorocyclopropyl) -2-methoxybenzene obtained in (4) was dried with N, N-dimethylformamide (5 mL) solution was added dropwise, and the mixture was stirred with heating at 160 ° C. for 5 hr. After allowing to cool, a 1 mol / L aqueous potassium hydroxide solution and diethyl ether were added to the reaction mixture. The aqueous layer was separated and washed with diethyl ether. Dilute hydrochloric acid was added to adjust to pH 2 and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give a crude product of 2- [1- (ethylsulfanyl) cyclopropyl] phenol 0.26 g was obtained.
(6) 6-chloro-3- {2- [1- (ethylsulfanyl) cyclopropyl] phenoxy} pyridazine 1-oxide (step B-2)
0.26 g of the crude 2- [1- (ethylsulfanyl) cyclopropyl] phenol product obtained in (5) was dissolved in a mixed solvent of 1,4-dioxane (3 mL) and dimethyl sulfoxide (3 mL). Then, 265.5 mg (2.37 mmol) of potassium tert-butoxide was added, and then 390.3 mg (2.37 mmol) of 3,6-dichloropyridazine 1-oxide was added, followed by stirring at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed with ethyl acetate: hexane = 2: 1), and 6-chloro-3 138.4 mg (0.428 mmol) of-{2- [1- (ethylsulfanyl) cyclopropyl] phenoxy} pyridazine 1-oxide was obtained.
(7) 4,6-Dichloro-3- {2- [1- (ethylsulfanyl) cyclopropyl] phenoxy} pyridazine (Step B-3)
138.4 mg (0.428 mmol) of 6-chloro-3- {2- [1- (ethylsulfanyl) cyclopropyl] phenoxy} pyridazine 1-oxide obtained by (6) was dissolved in phosphorus oxychloride (1 mL), and this solution Was stirred overnight at room temperature. Water and methylene chloride were added to the reaction solution, and the mixture was stirred for 30 minutes and extracted with methylene chloride. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (MERCK, using 1.05744 2 plates, developed with ethyl acetate: hexane = 4: 1), and 4,6-dichloro- 94.4 mg (0.277 mmol, yield 64.7%) of 3- {2- [1- (ethylsulfanyl) cyclopropyl] phenoxy} pyridazine was obtained.
(8) 6-chloro-3- {2- [1- (ethylsulfanyl) cyclopropyl] phenoxy} -4-pyridazinol (Compound No. 207, Step B-4)
9,4-Dichloro-3- {2- [1- (ethylsulfanyl) cyclopropyl] phenoxy} pyridazine 94.4 mg (0.277 mmol) obtained by (7) was added to 1,4-dioxane (1 mL) and dimethyl sulfoxide ( 1 mL) was dissolved in a mixed solvent, and 0.69 mL (1.38 mmol) of a 2 mol / L aqueous sodium hydroxide solution was added to the solution, followed by stirring overnight at room temperature. Water and ethyl acetate were added to the reaction solution, and the aqueous layer was separated and washed with ethyl acetate. Dilute hydrochloric acid was added to adjust to pH 2 and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, used in 2 plates, developed with ethyl acetate) to give 6-chloro-3- {2- [1 47.5 mg (0.147 mmol, 53.1% yield) of-(ethylsulfanyl) cyclopropyl] phenoxy} -4-pyridazinol (Compound No. 207) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.45-7.07 (4H, m), 6.69 (1H, s), 2.46 (2H, q, J = 7.3 Hz), 1.28-1.02 (9H, m).
Melting point (° C): 88.

Example 9
6-Chloro-3- [2- (2,2-dichlorocyclopropyl) phenoxy] -4-pyridazinol (Compound No. 265)
(1) 1- (2,2-Dichlorocyclopropyl) -2- (methoxymethoxy) benzene 305 mg (1.86 mmol) of 1- (methoxymethoxy) -2-vinylbenzene obtained in Example 7 (2) was mixed with chloroform. Into this solution, 5 mL (63 mmol) of 50% aqueous sodium hydroxide solution was added dropwise, followed by addition of 54.1 mg (0.237 mmol) of benzyl (triethyl) ammonium chloride, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with chloroform. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, using 3 plates, developed with ethyl acetate: hexane = 1: 2), and 1- (2, 387 mg (1.57 mmol, yield 84.4%) of 2-dichlorocyclopropyl) -2- (methoxymethoxy) benzene was obtained.
(2) 2- (2,2-dichlorocyclopropyl) phenol 1- (2,2-dichlorocyclopropyl) -2- (methoxymethoxy) benzene 203 mg (0.822 mmol) obtained from (1) was added to methanol (5 mL In this solution, 0.1 mL of concentrated hydrochloric acid was added and stirred at 60 ° C. for 2 hours. After confirming the disappearance of the raw materials by thin layer chromatography, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 194 mg of a crude product of 2- (2,2-dichlorocyclopropyl) phenol.
(3) 6-chloro-3- [2- (2,2-dichlorocyclopropyl) phenoxy] pyridazine 1-oxide (step B-2)
The crude product of 2- (2,2-dichlorocyclopropyl) phenol obtained in (2), 194 mg, 1,4-dioxane (3 mL) and dimethyl sulfoxide (3 mL) were mixed, and this mixture was cooled with ice. 118 mg (1.05 mmol) of potassium tert-butoxide was added, and the mixture was stirred for 10 minutes. Thereto was added 157 mg (0.952 mmol) of 3,6-dichloropyridazine 1-oxide, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin layer chromatography (MERCK, 1.05744, 3 plates used, developed with ethyl acetate: hexane = 1: 2), and 6-chloro-3- [2 268 mg of a crude product of-(2,2-dichlorocyclopropyl) phenoxy] pyridazine 1-oxide was obtained.
(4) 4,6-Dichloro-3- [2- (2,2-dichlorocyclopropyl) phenoxy] pyridazine (Step B-3)
268 mg of the crude product of 6-chloro-3- [2- (2,2-dichlorocyclopropyl) phenoxy] pyridazine 1-oxide obtained by (3) and 3 mL of phosphorus oxychloride were mixed, and this mixture was mixed at room temperature. Stir overnight. Water and dichloromethane were added to the reaction mixture and stirred for 30 minutes. The mixture was separated, and the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed with ethyl acetate: hexane = 1: 2), and 4,6-dichloro-3- 162 mg (0.463 mmol, 3-step yield from 1- (2,2-dichlorocyclopropyl) -2- (methoxymethoxy) benzene, 56.3%) [2- (2,2-dichlorocyclopropyl) phenoxy] pyridazine Obtained.
(5) 6-chloro-3- [2- (2,2-dichlorocyclopropyl) phenoxy] -4-pyridazinol (Compound No. 265, Step B-4)
4,6-dichloro-3- [2- (2,2-dichlorocyclopropyl) phenoxy] pyridazine obtained by (4) 162 mg (0.463 mmol), 1,4-dioxane (3 mL) and dimethyl sulfoxide (3 mL) To this mixture, 1.15 mL (2.30 mmol) of 2 mol / L aqueous sodium hydroxide solution was added and stirred overnight at room temperature. The reaction mixture was poured into water and acidified with dilute hydrochloric acid. This mixture was extracted with dichloromethane. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed with ethyl acetate) to give 6-chloro-3- [2- (2,2- 50.0 mg (0.151 mmol, yield 32.6%) of dichlorocyclopropyl) phenoxy] -4-pyridazinol (Compound No. 265) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.55-7.15 (4H, m), 6.69 (1H, s), 2.90 (1H, dd, J = 10.6, 8.8Hz), 2.07-1.89 (2H, m ).
Melting point (° C): 158-163.

(Example 10)
6-Chloro-3- (2-hydroxyphenoxy) -4-pyridazinol (Compound No. 384)
(1) 3-Chloro [1,4] benzodioxino [2,3-c] pyridazine (Step O-1)
3.49 g (80.0 mmol) of 55% sodium hydride was suspended in 1,4-dioxane (30 mL), and a solution of 4.40 g (40 mmol) of pyrocatechol in 1,4-dioxane (30 mL) and then 3,4,6-Trichloropyridazine {The Journal of Organic Chemistry, 1963, 28, 218-221. } A solution of 7.30 g (39.9 mmol) of 1,4-dioxane (30 mL) was added and heated to reflux for 2 hours. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined, washed sequentially with 1 mol / L sodium hydroxide and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was recrystallized from methyl isobutyl ketone to obtain 6.15 g (27.8 mmol, yield 69.7%) of 3-chloro [1,4] benzodioxino [2,3-c] pyridazine.
(2) 6-Chloro-3- (2-hydroxyphenoxy) -4-pyridazinol (Compound No. 384, Step O-2)
3-Chloro [1,4] benzodioxino [2,3-c] pyridazine obtained by (1) 5.52 g (25.0 mmol), 1.30 g of 96% sodium hydroxide (31.2 mmol), dimethyl sulfoxide (55 mL) and water (15 mL) of the mixture was stirred at 90 ° C. for 1 hour. The reaction mixture was poured into ice-cold water, acidified with hydrochloric acid, and extracted with ethyl acetate. The solvent was distilled off, and the residue was washed with isopropyl ether to obtain 4.90 g (20.5 mmol, yield 82.0%) of 6-chloro-3- (2-hydroxyphenoxy) -4-pyridazinol (Compound No. 384). .
¹ H-NMR (60 MHz, DMF-d ₇ ) δ ppm: 7.25-6.40 (5H, m).
Melting point (° C): 216-219.

(Example 11)
6-Chloro-3- [2- (methylsulfinyl) phenoxy] -4-pyridazinol (Compound No. 404)
(1) 6-chloro-3- [2- (methylsulfanyl) phenoxy] pyridazine 1-oxide (step B-2)
454 mg (3.24 mmol) of 2- (methylsulfanyl) phenol was dissolved in a mixed solvent of 1,4-dioxane (5 mL) and dimethyl sulfoxide (5 mL), and 519 mg (4.63 mmol) of potassium tert-butoxide was added to this solution for 35 minutes. Stir. To this mixture, 424 mg (2.57 mmol) of 3,6-dichloropyridazine 1-oxide was added and stirred for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel chromatography (eluted with Wakogel C-100, hexane: ethyl acetate = 3: 1) to give 6-chloro-3- [2- (methylsulfanyl) phenoxy. There was obtained 391 mg (1.46 mmol, yield 56.8%) of pyridazine 1-oxide.
(2) 4,6-Dichloro-3- [2- (methylsulfanyl) phenoxy] pyridazine (Step B-3)
6-Chloro-3- [2- (methylsulfanyl) phenoxy] pyridazine 1-oxide 288 mg (1.07 mmol) obtained from (1) and 1.00 mL (10.8 mmol) of phosphorus oxychloride were mixed and this mixture was allowed to stand overnight. Stir. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin layer chromatography (Merck, 1.05744, developed with hexane / ethyl acetate = 3/1), and 4,6-dichloro-3- [2- ( 118 mg (0.411 mmol, 38.4% yield) of methylsulfanyl) phenoxy] pyridazine were obtained.
(3) 4,6-dichloro-3- [2- (methylsulfinyl) phenoxy] pyridazine 118 mg (0.411 mmol) of 4,6-dichloro-3- [2- (methylsulfanyl) phenoxy] pyridazine obtained from (2) ) Was dissolved in 1,2-dichloroethane (4 mL), and 96.3 mg (purity 80%, 0.446 mmol) of m-chloroperbenzoic acid was added to this solution and stirred at room temperature for 5 hours. The reaction mixture was poured into a 10% aqueous sodium sulfite solution, extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (Merck, 1.05744, hexane: ethyl acetate = 1: 1, then 3: 1, then developed 1: 1). 21.1 mg (0.0696 mmol, yield 16.9%) of 6-dichloro-3- [2- (methylsulfinyl) phenoxy] pyridazine was obtained.
(4) 6-chloro-3- [2- (methylsulfinyl) phenoxy] -4-pyridazinol (Compound No. 404, Step B-4)
21.1 mg (0.0696 mmol) of 4,6-dichloro-3- [2- (methylsulfinyl) phenoxy] pyridazine obtained by (3) was dissolved in 1,4-dioxane (0.5 mL), and 3 mol / 0.12 mL (0.36 mmol) of L sodium hydroxide aqueous solution was added and stirred for 45 minutes. Dimethyl sulfoxide (0.5 mL) was added to the mixture, stirred for 3 hours, poured into 10% hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (Merck, 1.05744, chloroform: methanol = 10: 1) to give 6-chloro-3- [2- (methylsulfinyl) 2.1 mg (0.0074 mmol, 11% yield) of phenoxy] -4-pyridazinol (Compound No. 404) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.90-7.84 (1H, m), 7.60-7.42 (2H, m), 7.14 (1H, dd, J = 9.2, 1.1Hz), 6.62 (1H, s ), 2.92 (3H, s).
Physical properties: amorphous.

(Example 12)
6-Chloro-3- [2- (methylsulfonyl) phenoxy] -4-pyridazinol (Compound No. 406)
(1) 6-chloro-3- [2- (methylsulfonyl) phenoxy] pyridazine 1-oxide 6-chloro-3- [2- (methylsulfanyl) phenoxy] pyridazine 1-oxide obtained in Example 11 (1) Oxide 208 mg (0.774 mmol) was dissolved in 1,2-dichloroethane (5 mL), 80% m-chloroperbenzoic acid 829 mg (3.84 mmol) was added to the solution, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into 10% aqueous sodium sulfite and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (Merck, 1.05744, developed with hexane: ethyl acetate = 1: 1) to give 6-chloro-3- [2- 132 mg (0.439 mmol, 56.7% yield) of (methylsulfonyl) phenoxy] pyridazine 1-oxide were obtained.
(2) 4,6-Dichloro-3- [2- (methylsulfonyl) phenoxy] pyridazine (Step B-3)
6-Chloro-3- [2- (methylsulfonyl) phenoxy] pyridazine 1-oxide 111 mg (0.369 mmol) obtained in (1) and 1.00 mL (10.8 mmol) phosphorus oxychloride were mixed and the mixture was allowed to stand overnight. Stir. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with saturated sodium bicarbonate and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin layer chromatography (Merck, 1.05744, developed with hexane: ethyl acetate = 1: 1), and 4,6-dichloro-3- [2- ( 70.8 mg (0.222 mmol, 60.2% yield) of methylsulfonyl) phenoxy] pyridazine was obtained.
(3) 6-chloro-3- [2- (methylsulfonyl) phenoxy] -4-pyridazinol (Compound No. 406, Step B-4)
70.8 mg (0.222 mmol) of 4,6-dichloro-3- [2- (methylsulfonyl) phenoxy] pyridazine obtained by (2) was dissolved in 1,4-dioxane (2.0 mL), and 3 mol / L Sodium hydroxide aqueous solution 0.45mL (1.4mmol) was added and stirred for 30 minutes. Dimethyl sulfoxide (2.0 mL) was added to the mixture, and the mixture was stirred overnight, poured into water and washed with a mixed solvent of hexane-ethyl acetate. The aqueous layer was acidified with 10% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (Merck, 1.05744, developed with chloroform: methanol = 10: 1) to give 6-chloro-3- [2- ( 18.0 mg (0.0599 mmol, yield 27.0%) of methylsulfonyl) phenoxy] -4-pyridazinol (Compound No. 406) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 8.00 (1H, dd, J = 7.7, 1.8 Hz), 7.71 (1H, ddd, J = 7.7, 7.7, 1.8 Hz), 7.43 (1H, ddd, J = 7.7, 7.7, 1.1Hz), 7.32 (1H, br.d, J = 7.7Hz), 6.62 (1H, s), 3.36 (3H, s).
Physical properties: amorphous.

(Example 13)
6-chloro-3- (2-cyclopropyl-3-methoxyphenoxy) -4-pyridazinol (Compound No. 478)
(1) 6-chloro-3- (2-cyclopropyl-3-methoxyphenoxy) -4-methoxypyridazine (Step D-1)
190 mg (1.16 mmol) of 2-cyclopropyl-3-methoxyphenol was dissolved in a mixed solvent of 1,4-dioxane (2.5 mL) and dimethyl sulfoxide (2.5 mL), and 146 mg (1.30 mmol) of potassium tert-butoxide was added to this solution. In addition, the mixture was stirred for 10 minutes. To this mixture, 170 mg (0.950 mmol) of 3,6-dichloro-4-methoxypyridazine was added and left overnight. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 6-chloro-3- (2-cyclopropyl-3-methoxyphenoxy)- 90.1 mg (0.293 mmol, yield 30.8%) 4-methoxypyridazine and 114 mg (0.371 mmol, yield 39.1%) 3-chloro-6- (2-cyclopropyl-3-methoxyphenoxy) -4-methoxypyridazine Obtained.
(2) 6-chloro-3- (2-cyclopropyl-3-methoxyphenoxy) -4-pyridazinol (Compound No. 478, Step D-2)
24 mg (0.60 mmol) of 60% sodium hydride was suspended in dry N, N-dimethylformamide (DMF, 2 mL), and 0.05 mL (0.7 mmol) of ethanethiol was added dropwise to the suspension under ice cooling. For 10 minutes. To this mixture was added 60.0 mg (0.195 mmol) of 6-chloro-3- (2-cyclopropyl-3-methoxyphenoxy) -4-methoxypyridazine obtained in (1) with dry N, N-dimethylformamide (DMF, 1.5 mL) solution was added and heated to reflux for 2 hours. The reaction mixture was cooled, poured into ice-cooled 1 mol / L aqueous sodium hydroxide solution, and washed with ethyl acetate. Ice-cold concentrated hydrochloric acid was added to the aqueous layer to adjust to pH 4, and the mixture was extracted with ethyl acetate. The ethyl acetate extracts were combined, washed successively with water and saturated brine, and dried over sodium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (Merck, 1.05744, 3 plates used, developed with hexane: ethyl acetate = 1: 1), and 6-chloro-3 15.2 mg (0.0519 mmol, yield 26.6%) of-(2-cyclopropyl-3-methoxyphenoxy) -4-pyridazinol (Compound No. 478) was obtained.
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.19 (1H, dd, J = 8.1, 8.4 Hz), 6.76 (1H, d, J = 8.1 Hz), 6.69 (1H, d, J = 8.4 Hz), 6.60 (1H, s), 3.85 (3H, s), 1.55-1.35 (1H, m), 0.85-0.60 (4H, m).
Melting point (° C): 184-185.

(Example 14)
3- (1,1a, 6,6a-Tetrahydrocyclopropa [a] inden-2-yloxy) -6-chloro-4-pyridazinol (Compound No. 515)
(1) 7-Hydroxy-1-indanone 37.0 g (278 mmol) of aluminum chloride was mixed with 3.70 g (61.3 mmol) of sodium chloride, this mixture was heated and dissolved at 150 ° C., and dissolved by heating (50 ° C.). Of 2,3 dihydro-4H-chromen-4-one 6.40 g (43.2 mmol) was added and stirred at 200 ° C. for 20 minutes. The reaction mixture (gum-like) was cooled, added to ice-cooled hydrochloric acid (100 ml of concentrated hydrochloric acid and ice to make 200 ml) little by little, and stirred for 30 minutes. Methylene chloride was added to the mixture and the layers were separated. The aqueous layer was filtered and the filtrate was extracted with methylene chloride. The organic layers were combined, washed successively with water and saturated brine, and dried over sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 4.82 g (32.6 mmol, yield 75.2% of 7-hydroxy-1-indanone. )Obtained.
(2) 7- (methoxymethoxy) -1-indanone 1.00 g (6.76 mmol) of 7-hydroxy-1-indanone obtained from (1) was dissolved in N, N-dimethylformamide (DMF, 33 mL), and this solution The mixture was cooled with ice, and 0.330 g (8.25 mmol) of 60% sodium hydride was added in four portions, followed by stirring for 30 minutes. To this mixture, 0.80 mL (11 mmol) of chloromethoxymethane was added dropwise and stirred at room temperature for 2 hours. The reaction mixture was poured into ice-cooled saturated aqueous ammonium chloride solution (100 mL) and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 1.04 g (5.42 mmol, 7- (methoxymethoxy) -1-indanone. Rate 80.2%).
(3) 7- (Methoxymethoxy) -1-indanol 7-Methoxymethoxy-1-indanone (1.04 g, 5.42 mmol) obtained from (2) was dissolved in methanol (20 mL). 164 mg (4.34 mmol) of sodium borohydride was added and stirred at room temperature for 4 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 1.05 g (5.42 mmol, 7- (methoxymethoxy) -1-indanol. Rate 100%).
(4) Mixture of 4- (methoxymethoxy) -1H-indene and 7- (methoxymethoxy) -1H-indene 500 mg (2.58 mmol) of 7- (methoxymethoxy) -1-indanol obtained by (3) was chlorinated. This was dissolved in methylene (3 mL), the solution was ice-cooled, 0.50 mL (3.7 mmol) of triethylamine and 0.25 mL (3.3 mmol) of methanesulfonyl chloride were added, and the mixture was stirred for 2 hours. After adding 0.80 mL (5.7 mmol) of triethylamine and stirring for 1 hour, the mixture was poured into water and extracted with methylene chloride. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was dissolved in pyridine (3 mL) and heated to reflux for 4 hours. After standing at room temperature overnight, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 4- (methoxymethoxy) -1H-indene and 7- (methoxymethoxy)- 280 mg (1.59 mmol, yield 61.6%) of a mixture of 1H-indene was obtained.
(5) (2- (methoxymethoxy) -1,1a, 6,6a-tetrahydrocyclopropa [a] indene and 5- (methoxymethoxy) -1,1a, 6,6a-tetrahydrocyclopropa [a] indene blend
Under a nitrogen stream, dry diethyl ether (5 mL) was added to a 30 mL eggplant flask and ice-cooled. Diethyl zinc (1.0 mol / L hexane solution) 6.3 mL (6.3 mmol) and diiodomethane 0.70 mL (8.5 mmol) were successively added dropwise thereto and stirred for 10 minutes. To this mixture, an ether solution (9 mL) of 250 mg (1.42 mmol) of the mixture of 4- (methoxymethoxy) -1H-indene and 7- (methoxymethoxy) -1H-indene obtained in (4) was slowly added dropwise. The mixture was heated to reflux for 4 hours. The reaction mixture was cooled and poured into saturated aqueous ammonium chloride solution. The same volume of saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with ether. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 2- (methoxymethoxy) -1,1a, 6,6a-tetrahydrocyclopropaline. 150 mg (0.789 mmol, yield 55.6%) of a mixture of [a] indene and 5- (methoxymethoxy) -1,1a, 6,6a-tetrahydrocyclopropa [a] indene was obtained.
(6) A mixture of 1,1a, 6,6a-tetrahydrocyclopropa [a] inden-2-ol and 1,1a, 6,6a-tetrahydrocyclopropa [a] inden-5-ol 150 mg of a mixture of 2- (methoxymethoxy) -1,1a, 6,6a-tetrahydrocyclopropa [a] indene and 5- (methoxymethoxy) -1,1a, 6,6a-tetrahydrocyclopropa [a] indene ( 0.789 mmol) was dissolved in methanol (6 mL), 2 drops of concentrated hydrochloric acid were added to this solution, and the mixture was stirred at room temperature for 1 hour and then stirred at 60 ° C. for 20 minutes. The reaction mixture was cooled, poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (Merck, 1.05744, developed with hexane: ethyl acetate = 2: 1), and 1,1a, 6,6a-tetrahydro 80.0 mg (0.548 mmol, 69.5% yield) of a mixture of cyclopropa [a] inden-2-ol and 1,1a, 6,6a-tetrahydrocyclopropa [a] inden-5-ol was obtained.
(7) 3- (1,1a, 6,6a-tetrahydrocyclopropa [a] inden-2-yloxy) -6-chloropyridazine 1-oxide and 3- (1,1a, 6,6a-tetrahydrocyclopropa [ a] A mixture of inden-5-yloxy) -6-chloropyridazine 1-oxide (step B-2)
Mixture of 1,1a, 6,6a-tetrahydrocyclopropa [a] inden-2-ol and 1,1a, 6,6a-tetrahydrocyclopropa [a] inden-5-ol obtained by (6) 80.0 mg (0.548 mmol) was dissolved in a mixed solvent of 1,4-dioxane (2 mL) and dimethyl sulfoxide (2 mL), and 85 mg (0.76 mmol) of potassium tert-butoxide was added to this solution and stirred for 10 minutes. To this, 82 mg (0.50 mmol) of 3,6-dichloropyridazine 1-oxide was added and stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (Merck, 1.05744, 4 plates used, developed with hexane: ethyl acetate = 2: 1), and 3- (1, 1a, 6,6a-Tetrahydrocyclopropa [a] inden-2-yloxy) -6-chloropyridazine 1-oxide and 3- (1,1a, 6,6a-tetrahydrocyclopropa [a] inden-5-yloxy) 75.0 mg (0.273 mmol, 49.8% yield) of a mixture of -6-chloropyridazine 1-oxide was obtained.
(8) 3- (1,1a, 6,6a-tetrahydrocyclopropa [a] inden-2-yloxy) -4,6-dichloropyridazine and 3- (1,1a, 6,6a-tetrahydrocyclopropa [a ] Inden-5-yloxy) -4,6-dichloropyridazine (Step B-3)
3- (1,1a, 6,6a-tetrahydrocyclopropa [a] inden-2-yloxy) -6-chloropyridazine 1-oxide and 3- (1,1a, 6,6a-) obtained by (7) A mixture of tetrahydrocyclopropa [a] inden-5-yloxy) -6-chloropyridazine 1-oxide 75.0 mg (0.273 mmol) was mixed with 0.30 mL (3.2 mmol) phosphorus oxychloride and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure to remove phosphorous oxychloride, and the residue was preparative thin-layer chromatography (Merck, 1.05744, 3 plates used, hexane / ethyl acetate = 9/1 developed 4 times) 21.4 mg (0.0730 mmol, yield 26.7%) of 3- (1,1a, 6,6a-tetrahydrocyclopropa [a] inden-2-yloxy) -4,6-dichloropyridazine And 32.6 mg (0.111 mmol, yield 40.7%) of 3- (1,1a, 6,6a-tetrahydrocyclopropa [a] inden-5-yloxy) -4,6-dichloropyridazine was obtained.
(9) 3- (1,1a, 6,6a-tetrahydrocyclopropa [a] inden-2-yloxy) -6-chloro-4-pyridazinol (Compound No. 515, Step B-4)
3- (1,1a, 6,6a-tetrahydrocyclopropa [a] inden-2-yloxy) -4,6-dichloropyridazine 21.4 mg (0.0730 mmol) solution obtained in (8) in dimethyl sulfoxide (3 mL) Was added with 0.1 mL (0.2 mmol) of 2 mol / L sodium hydroxide aqueous solution and stirred at room temperature for 3 hours. The reaction mixture was poured into an ice-cooled 1 mol / L aqueous sodium hydroxide solution and washed with ethyl acetate. The aqueous layer was separated, adjusted to pH 4 by adding concentrated hydrochloric acid under ice cooling, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over sodium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (Merck, 1.05744, 1 plate used, developed with chloroform: methanol = 10: 1), and 3- (1,1a , 6,6a-tetrahydrocyclopropa [a] inden-2-yloxy) -6-chloro-4-pyridazinol (Compound No. 515) was obtained in an amount of 10.3 mg (0.0375 mmol, yield 51.4%).
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.08 (1H, t, J = 7.7 Hz), 6.98 (1H, d, J = 7.7 Hz), 6.84 (1H, d, J = 7.7 Hz), 6.59 (1H, s), 3.20 (1H, dd, J = 17.2, 6.2Hz), 2.94 (1H, d, J = 17.2Hz), 2.30-2.15 (1H, m), 1.90-1.75 (1H, m), 1.05-0.90 (1H, m).
Melting point (° C): 245-247.

(Example 15)
3- (1,1a, 6,6a-tetrahydrocyclopropa [a] inden-5-yloxy) -6-chloro-4-pyridazinol (Compound No. 516, Step B-4)
3- (1,1a, 6,6a-tetrahydrocyclopropa [a] inden-5-yloxy) -4,6-dichloropyridazine (32.6 mg, 0.111 mmol) obtained in Example 14 (8) was added to dimethyl sulfoxide ( 3 mL), and 0.1 mL (0.2 mmol) of a 2 mol / L sodium hydroxide aqueous solution was added to the solution, followed by stirring at room temperature for 4 hours. The reaction mixture was poured into an ice-cooled 1 mol / L aqueous sodium hydroxide solution and washed with ethyl acetate. The aqueous layer was separated, adjusted to pH 4 by adding concentrated hydrochloric acid under ice cooling, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over sodium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (Merck, 1.05744, 1 plate used, developed with chloroform: methanol = 10: 1), and 3- (1,1a 1,6,6a-tetrahydrocyclopropa [a] inden-5-yloxy) -6-chloro-4-pyridazinol (Compound No. 516) was obtained in an amount of 13.4 mg (0.0487 mmol, yield 43.9%).
¹ H-NMR (200MHz, CD ₃ OD) δppm: 7.25-7.05 (2H, m), 6.83 (1H, dd, J = 6.6, 2.6Hz), 6.67 (1H, s), 3.00 (1H, dd, J = 17.2, 6.6Hz), 2.78 (1H, d, J = 17.2Hz), 2.50-2.35 (1H, m), 2.00-1.80 (1H, m), 1.15-1.00 (1H, m), 0.10-0.00 ( 1H, m).
Melting point (° C): 211-213.

(Example 16)
6-Chloro-3- (2-methoxy-5-methylphenoxy) -4-pyridazinol (Compound No. 704)
(1) 6-chloro-3- (2-methoxy-5-methylphenoxy) pyridazine 1-oxide (step B-2)
167.5 mg (1.21 mmol) of commercially available 2-methoxy-5-methylphenol was dissolved in a mixed solvent of 1,4-dioxane (3 mL) and dimethyl sulfoxide (3 mL), and 142.8 mg (1.27 mmol) of potassium tert-butoxide was added to this solution. Then, 202.9 mg (1.23 mmol) of 3,6-dichloropyridazine 1-oxide was added and stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed with ethyl acetate: hexane = 2: 1), and 6-chloro-3 226.5 mg (0.849 mmol, yield 70.2%) of-(2-methoxy-5-methylphenoxy) pyridazine 1-oxide was obtained.
(2) 4,6-Dichloro-3- (2-methoxy-5-methylphenoxy) pyridazine (Step B-3)
Dissolve 226.5 mg (0.849 mmol) of 6-chloro-3- (2-methoxy-5-methylphenoxy) pyridazine 1-oxide obtained in (1) in phosphorus oxychloride (1 mL) and stir this solution at room temperature overnight. did. Water and methylene chloride were added to the reaction solution, and the mixture was stirred for 30 minutes and extracted with methylene chloride. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed with ethyl acetate: hexane = 2: 1), and 4,6-dichloro 205.3 mg (0.720 mmol, yield 84.8%) of -3- (2-methoxy-5-methylphenoxy) pyridazine was obtained.
(3) 6-chloro-3- (2-methoxy-5-methylphenoxy) -4-pyridazinol (Compound No. 704, Step B-4)
205.3 mg (0.720 mmol) of 4,6-dichloro-3- (2-methoxy-5-methylphenoxy) pyridazine obtained by (2) was mixed with 1,4-dioxane (5 mL) and dimethyl sulfoxide (5 mL) mixed solvent. Then, 1.8 mL (3.6 mmol) of a 2 mol / L aqueous sodium hydroxide solution was added to the solution, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, diluted hydrochloric acid was added to adjust to pH 2, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (MERCK, 1.05744, 3 plates used, developed with ethyl acetate), and 6-chloro-3- (2-methoxy- 148.1 mg (0.555 mmol, yield 77.1%) of 5-methylphenoxy) -4-pyridazinol (Compound No. 704) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.04-6.91 (3H, m), 6.66 (1H, s), 3.70 (3H, s), 2.27 (3H, s).
Melting point (° C): 126-134.

(Example 17)
6-chloro-3- {2- [1- (ethylsulfanyl) ethyl] -6-fluorophenoxy} -4-pyridazinol (Compound No. 728)
(1) 3-Fluoro-2-methoxybenzaldehyde To a solution of 3.01 g (21.5 mmol) of commercially available 3-fluoro-2-hydroxybenzaldehyde in acetonitrile (50 mL), 5.92 g (42.8 mmol) of potassium carbonate and 6.66 mL of methyl iodide ( 107 mmol) was added and the mixture was stirred with heating at 90 ° C. for 3 hours. After standing overnight at room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 3.22 g of a crude product of 3-fluoro-2-methoxybenzaldehyde. .
(2) 1-Fluoro-2-methoxy-3-vinylbenzene In a nitrogen atmosphere, 273.2 mg (6.83 mmol) of 60% sodium hydride washed with hexane was suspended in dry dimethyl sulfoxide (3 mL). After heating and stirring at 85 ° C. for 30 minutes, the solution was returned to room temperature and further a solution of 2.44 g (6.83 mmol) of methyl (triphenyl) phosphonium bromide in dry dimethyl sulfoxide (8 mL) was slowly added dropwise under ice cooling. After stirring at room temperature for 30 minutes, a solution of 877.4 mg of the crude product of 3-fluoro-2-methoxybenzaldehyde obtained in (1) in dry dimethyl sulfoxide (5 mL) was added dropwise and stirred at room temperature for 30 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 0.38 g (2.5% of 1-fluoro-2-methoxy-3-vinylbenzene). Mmol).
(3) 1-Cyclopropyl-3-fluoro-2-methoxybenzene In a nitrogen atmosphere, put dry diethyl ether (5 mL) into a dry flask and add dropwise diethyl zinc (1 mol / L hexane solution) 9.20 mL (9.20 mmol). A solution of 0.56 g (3.7 mmol) of 1-fluoro-2-methoxy-3-vinylbenzene obtained in (2) in dry diethyl ether (10 mL) was added dropwise. After stirring at room temperature for 5 minutes, 1.48 mL (18.4 mmol) of diiodomethane was added dropwise and heated to reflux for 5 hours. After cooling to room temperature, 9.20 mL (9.20 mmol) of diethylzinc (1 mol / L hexane solution) and 1.48 mL (18.4 mmol) of diiodomethane were added, and the mixture was heated to reflux again for 4 hours. After standing overnight at room temperature, the reaction mixture was poured into saturated aqueous ammonium chloride solution. A saturated aqueous sodium hydrogen carbonate solution was added thereto, and the mixture was stirred for 30 minutes and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give a crude product of 1-cyclopropyl-3-fluoro-2-methoxybenzene 0.82 g was obtained.
(4) 6-chloro-3- {2- [1- (ethylsulfanyl) ethyl] -6-fluorophenoxy} pyridazine 1-oxide (step B-2)
Under a nitrogen atmosphere, 288.8 mg (7.22 mmol) of 60% sodium hydride was suspended in dry N, N-dimethylformamide (3 mL), and ethanethiol 0.55 mL (7.5 mmol) was slowly added dropwise thereto. After stirring for 15 minutes, a solution of 402.1 mg of the crude product of 1-cyclopropyl-3-fluoro-2-methoxybenzene obtained in (3) in dry N, N-dimethylformamide (6 mL) was added dropwise at 160 ° C. The mixture was heated and stirred for 5 hours. After standing overnight at room temperature, a 1 mol / L aqueous potassium hydroxide solution and diethyl ether were added to the reaction mixture. The aqueous layer was separated, washed with diethyl ether, and adjusted to pH 2 by adding dilute hydrochloric acid. This was extracted with diethyl ether, and the ether extracts were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (developed with ethyl acetate: hexane = 4: 1 using three 1.05744 manufactured by MERCK) to obtain 299.9 mg of a mixture.
152.7 mg of this mixture was dissolved in a mixed solvent of 1,4-dioxane (3 mL) and dimethyl sulfoxide (3 mL), and 116.1 mg (1.03 mmol) of potassium tert-butoxide was added to this solution, and then 3,6-dichloropyridazine 1 162.6 mg (0.988 mmol) of oxide was added, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed with ethyl acetate: hexane = 2: 1), and 6-chloro-3 46.6 mg (0.144 mmol) of-{2- [1- (ethylsulfanyl) ethyl] -6-fluorophenoxy} pyridazine 1-oxide was obtained.
(5) 4,6-Dichloro-3- {2- [1- (ethylsulfanyl) ethyl] -6-fluorophenoxy} pyridazine (Step B-3)
6-chloro-3- {2- [1- (ethylsulfanyl) ethyl] -6-fluorophenoxy} pyridazine 1-oxide 46.6 mg (0.144 mmol) obtained in (4) in a solution of phosphorus oxychloride (0.5 mL) Was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (MERCK, 1.05744, 1 plate used, developed with ethyl acetate: hexane = 4: 1), and 4,6-dichloro 9.8 mg (0.028 mmol, 19% yield) of 3- {2- [1- (ethylsulfanyl) ethyl] -6-fluorophenoxy} pyridazine was obtained.
(6) 6-chloro-3- {2- [1- (ethylsulfanyl) ethyl] -6-fluorophenoxy} -4-pyridazinol (Compound No. 728, Step B-4)
9.8 mg (0.028 mmol) of 4,6-dichloro-3- {2- [1- (ethylsulfanyl) ethyl] -6-fluorophenoxy} pyridazine obtained by (5) was added to 1,4-dioxane (1 mL) and Dissolved in a mixed solvent of dimethyl sulfoxide (1 mL), to this solution was added 0.07 mL (0.14 mmol) of a 2 mol / L aqueous sodium hydroxide solution and stirred at room temperature overnight. The reaction mixture was poured into water, adjusted to pH 2 with dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (MERCK, 1.05744, 1 plate used, developed with ethyl acetate) to give 6-chloro-3- {2- [1 There was obtained 2.2 mg (0.0067 mmol, yield 24%) of-(ethylsulfanyl) ethyl] -6-fluorophenoxy} -4-pyridazinol (Compound No. 728).
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.42 (1H, d, J = 8.1 Hz), 7.26-7.15 (1H, m), 7.07-6.97 (1H, m), 6.46 (1H, s), 4.33 (1H, q, J = 7.0Hz), 2.42-2.20 (2H, m), 1.43 (3H, d, J = 7.0Hz), 1.02 (3H, t, J = 7.0Hz).
Physical properties: amorphous.

(Example 18)
6-Chloro-3- (2-chloro-6-isopropylphenoxy) -4-pyridazinol (Compound No. 738)
(1) 1-Isopropyl-2-[(2-methoxyethoxy) methoxy] benzene
4.80 g (120 mmol) of 60% sodium hydride was suspended in dry tetrahydrofuran (60 mL). To this suspension, a solution of 13.6 g (100 mmol) of 2-isopropylphenol in dry tetrahydrofuran (80 mL) was added dropwise at 0 ° C. . After stirring at 0 ° C. for 10 minutes, a solution of 14.9 g (119 mmol) of 2-methoxyethoxymethyl chloride in dry tetrahydrofuran (80 mL) was added dropwise. The reaction mixture was stirred for 2 hours under ice cooling, poured into ice cold water (250 mL), and extracted with ethyl acetate. The organic layers were combined, washed successively with 1 mol / L aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (eluting with hexane: ethyl acetate = 50: 1), and 18.1 g (80.8 g) of 1-isopropyl-2-[(2-methoxyethoxy) methoxy] benzene was obtained. Mmol, yield 80.8%).
(2) 1-chloro-3-isopropyl-2-[(2-methoxyethoxy) methoxy] benzene 1-isopropyl-2-[(2-methoxyethoxy) methoxy] benzene 8.00 g (35.7 Mmol) was dissolved in dry ether (100 mL), and 34.4 mL (55.0 mmol) of n-butyllithium hexane solution (1.60 M) was added dropwise to the solution under ice cooling (reaction temperature 5-10 ° C.). Stir for 5 hours. Chlorine gas (2.51 g, 35.4 mmol) was blown into the reaction solution while maintaining the reaction solution temperature at 5-10 ° C. The reaction mixture was stirred for 1 hour under ice cooling, poured into 1 mol / L hydrochloric acid (300 mL), and extracted with ether. The organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluting with hexane: ethyl acetate = 100: 1), and 4.38 g (16.9 mmol, 16.9 mmol, 1-chloro-3-isopropyl-2-[(2-methoxyethoxy) methoxy] benzene) was obtained. Yield 47.3%).
(3) 2-Chloro-6-isopropylphenol 4.38 g (16.9 mmol) of 1-chloro-3-isopropyl-2-[(2-methoxyethoxy) methoxy] benzene obtained from (2) was added to dichloromethane (15 mL). To this solution was added 2.70 g (23.7 mmol) of trifluoroacetic acid, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into 1 mol / L hydrochloric acid and extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (eluted with hexane) to obtain 2.50 g (14.7 mmol, yield 87.0%) of 2-chloro-6-isopropylphenol.
(4) 3-Chloro-6- (2-chloro-6-isopropylphenoxy) pyridazine (Step A-1)
1.98 g (17.7 mmol) of potassium tert-butoxide, 2.50 g (14.7 mmol) of 2-chloro-6-isopropylphenol obtained in (3) and 1,4-dioxane (100 mL) were mixed, and the mixture was mixed at room temperature. For 20 minutes. To this, 2.18 g (14.6 mmol) of 3,6-dichloropyridazine was added and heated under reflux for 4 hours. To the reaction mixture, 0.50 g (4.5 mmol) of potassium tert-butoxide was added, and the mixture was further heated to reflux for 3 hours. The reaction mixture was allowed to cool, poured into 1N hydrochloric acid (100 mL), and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate, gradient) to give 3.18 g (11.2%) of 3-chloro-6- (2-chloro-6-isopropylphenoxy) pyridazine. Mmol, yield 76.2%).
(5) A mixture of 6-chloro-3- (2-chloro-6-isopropylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-chloro-6-isopropylphenoxy) pyridazine 1-oxide (Step C- 1)
3.17 g (11.2 mmol) of 3-chloro-6- (2-chloro-6-isopropylphenoxy) pyridazine obtained in (4) was dissolved in dry dichloromethane (90 mL), and 80-85% m-chloroperoxide was added to this solution. 2.90 g (13.4-14.3 mmol) of benzoic acid was added and heated to reflux for 13 hours. The reaction mixture was poured into 1N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate, gradient) to give 6-chloro-3- (2-chloro-6-isopropylphenoxy) pyridazine 1-oxide and 3 2.82 g (9.43 mmol, yield 84.2%) of a mixture of -chloro-6- (2-chloro-6-isopropylphenoxy) pyridazine 1-oxide was obtained.
(6) Mixture of 4,6-dichloro-3- (2-chloro-6-isopropylphenoxy) pyridazine and 3,4-dichloro-6- (2-chloro-6-isopropylphenoxy) pyridazine (Step C-2)
Mixture of 6-chloro-3- (2-chloro-6-isopropylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-chloro-6-isopropylphenoxy) pyridazine 1-oxide obtained by (5) 2.80 g (9.36 mmol) was mixed with 17.5 mL (189 mmol) of phosphorus oxychloride and the mixture was heated to reflux for 2 hours 30 minutes. The reaction mixture was allowed to cool, poured into ice-cold water, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 20: 1) to give 4,6-dichloro-3- (2-chloro-6-isopropylphenoxy) pyridazine. 0.850 g (2.67 mmol, mp 90-91 ° C.), 4,6-dichloro-3- (2-chloro-6-isopropylphenoxy) pyridazine and 3,4-dichloro-6- (2-chloro-6-isopropylphenoxy) 1.78 g (5.60 mmol) of a pyridazine mixture was obtained.
(7) 6-chloro-3- (2-chloro-6-isopropylphenoxy) -4-methoxypyridazine and 3-chloro-6- (2-chloro-6-isopropylphenoxy) -4-methoxypyridazine (Step C- 3)
Sodium (0.080 g, 3.5 mmol) was added to methanol (10 mL), and the mixture was stirred at room temperature for 30 minutes. To this, 0.830 g (2.61 mmol) of 4,6-dichloro-3- (2-chloro-6-isopropylphenoxy) pyridazine obtained in (6) was added and stirred at room temperature for 2 hours. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate, and the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1), washed with hexane to crystallize, and 6-chloro-3- (2-chloro-6-isopropylphenoxy) -4 0.720 g (2.30 mmol, yield 88.1%) of -methoxypyridazine was obtained. Meanwhile, 1.78 g (5.60 mmol) of a mixture of 4,6-dichloro-3- (2-chloro-6-isopropylphenoxy) pyridazine and 3,4-dichloro-6- (2-chloro-6-isopropylphenoxy) pyridazine By reacting in the same manner, 1.25 g (3.99 mmol, 71.3% yield) of 6-chloro-3- (2-chloro-6-isopropylphenoxy) -4-methoxypyridazine, 3-chloro-6- (2-chloro- 0.300 g (0.958 mmol, yield 17.1%) of 6-isopropylphenoxy) -4-methoxypyridazine was obtained.
(8) 6-chloro-3- (2-chloro-6-isopropylphenoxy) -4-pyridazinol (Compound No. 738, Step C-4)
1.46 g (4.66 mmol) of 6-chloro-3- (2-chloro-6-isopropylphenoxy) -4-methoxypyridazine obtained by (7) was dissolved in dimethyl sulfoxide (13 mL), and 2 mol / L water was added to this solution. 3 mL (6.0 mmol) of an aqueous sodium oxide solution was added, and the mixture was stirred at 80 ° C. for 3 hours. The reaction mixture was poured into water and acidified with hydrochloric acid. The precipitated solid was collected by filtration, washed with water and air dried. 1.33 g (4.45 mmol, yield 95.5%) of 6-chloro-3- (2-chloro-6-isopropylphenoxy) -4-pyridazinol (Compound No. 738) was obtained.
¹ H-NMR (60MHz, DMSO-d ₆ ) δppm: 7.40-7.05 (3H, m), 6.70 (1H, s), 2.98 (1H, septet, J = 6.2Hz), 1.13 (6H, d, J = 6.2Hz).
Melting point (° C): 218-233.

(Example 19)
3- (2-Bromo-6-isopropylphenoxy) -6-chloro-4-pyridazinol (Compound No. 760)
(1) 1-Bromo-3-isopropyl-2-[(2-methoxyethoxy) methoxy] benzene 1-isopropyl-2-[(2-methoxyethoxy) methoxy] benzene 5.18 obtained in Example 18 (1) g (23.1 mmol) was dissolved in dry ether (100 mL), and 22.3 mL (35.7 mmol) of n-butyllithium hexane solution (1.60M) was added dropwise to the solution under ice cooling (reaction temperature 5-10 ° C.). The mixture was stirred for 5 hours under ice cooling. To this, 8.20 g (69.7 mmol) of 90% cyanogen bromide was added while keeping the reaction solution temperature at 5-10 ° C. The reaction mixture was stirred for 2 hours under ice cooling, poured into ice cold water (300 mL), and extracted with ether. The organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluted with hexane: ethyl acetate = 100: 1) to give 3.40 g (11.2 mmol, 1-bromo-3-isopropyl-2-[(2-methoxyethoxy) methoxy] benzene. Yield 48.5%).
(2) 2-Bromo-6-isopropylphenol 1.40 g (11.2 mmol) of 1-bromo-3-isopropyl-2-[(2-methoxyethoxy) methoxy] benzene obtained by (1) was added to dichloromethane (10 mL). After dissolution, 2.50 g (21.9 mmol) of trifluoroacetic acid was added to the solution and stirred overnight at room temperature. The reaction mixture was poured into 1 mol / L hydrochloric acid and extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (eluted with hexane) to obtain 2.27 g (10.6 mmol, yield 94.6%) of 2-bromo-6-isopropylphenol.
(3) 3- (2-Bromo-6-isopropylphenoxy) -6-chloropyridazine (Step A-1)
Potassium tert-butoxide 1.52 g (13.6 mmol), 1,4-dioxane (60 mL) and 2.27 g (10.6 mmol) of 2-bromo-6-isopropylphenol obtained from (2) were mixed, and the mixture was mixed at room temperature. Stir for 20 minutes. To this, 1.58 g (10.6 mmol) of 3,6-dichloropyridazine was added and heated under reflux for 7 hours and 20 minutes. The reaction mixture was allowed to cool, poured into ice-cold water (110 mL), and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was recrystallized (isopropyl ether) and then purified by silica gel column chromatography (hexane: ethyl acetate, gradient) to give 3- (2-bromo-6-isopropylphenoxy) -6 -2.68 g (8.17 mmol, yield 77.1%) of -chloropyridazine was obtained.
(4) A mixture of 3- (2-bromo-6-isopropylphenoxy) -6-chloropyridazine 1-oxide and 6- (2-bromo-6-isopropylphenoxy) -3-chloropyridazine 1-oxide (Step C- 1)
3.68 g (8.17 mmol) of 3- (2-bromo-6-isopropylphenoxy) -6-chloropyridazine obtained by (3) was dissolved in dry dichloromethane (35 mL), and 80-85% m-chloroperoxide was added to this solution. 2.12 g (9.80-10.4 mmol) of benzoic acid was added, and the mixture was heated to reflux for 12 hours and 30 minutes. The reaction mixture was poured into 1 mol / L aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 5: 1) to give 3- (2-bromo-6-isopropylphenoxy) -6-chloropyridazine 1-oxide. And 2.26 g (6.57 mmol, yield 80.4%) of a mixture of 6- (2-bromo-6-isopropylphenoxy) -3-chloropyridazine 1-oxide.
(5) Mixture of 3- (2-bromo-6-isopropylphenoxy) -4,6-dichloropyridazine and 6- (2-bromo-6-isopropylphenoxy) -3,4-dichloropyridazine (Step C-2)
Mixture of 3- (2-bromo-6-isopropylphenoxy) -6-chloropyridazine 1-oxide and 6- (2-bromo-6-isopropylphenoxy) -3-chloropyridazine 1-oxide obtained by (4) 2.14 g (6.22 mmol) was mixed with 11.6 mL (125 mmol) phosphorus oxychloride and the mixture was heated to reflux for 3 hours. The reaction mixture was allowed to cool, poured into ice-cold water, and extracted with ethyl acetate. The organic layers were combined, washed successively with 1 mol / L sodium hydroxide aqueous solution, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 20: 1) to give 3- (2-bromo-6-isopropylphenoxy) -4,6-dichloropyridazine and There was obtained 2.22 g (6.13 mmol, yield 98.6%) of a mixture of 6- (2-bromo-6-isopropylphenoxy) -3,4-dichloropyridazine.
(6) 3- (2-Bromo-6-isopropylphenoxy) -6-chloro-4-methoxypyridazine (Step C-3)
Sodium (0.180 g, 7.8 mmol) was added to methanol (20 mL), and the mixture was stirred at room temperature for 30 minutes. Here, a mixture of 3- (2-bromo-6-isopropylphenoxy) -4,6-dichloropyridazine and 6- (2-bromo-6-isopropylphenoxy) -3,4-dichloropyridazine obtained by (5) 2.22 g (6.13 mmol) was added and stirred at room temperature for 4 hours. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate = 15: 1), washed with hexane to crystallize, and 3- (2-bromo-6-isopropylphenoxy) 1.48 g (4.13 mmol, yield 67.4%) of -6-chloro-4-methoxypyridazine was obtained. At the same time, 0.21 g (0.59 mmol, yield 9.6%) of 6- (2-bromo-6-isopropylphenoxy) -3-chloro-4-methoxypyridazine was obtained.
(7) 3- (2-Bromo-6-isopropylphenoxy) -6-chloro-4-pyridazinol (Compound No. 760, Step C-4)
3- (2-Bromo-6-isopropylphenoxy) -6-chloro-4-methoxypyridazine 0.72 g (2.0 mmol) obtained in (6) was dissolved in dimethyl sulfoxide (10 mL), and this solution was added to an aqueous sodium hydroxide solution. (100 mg of sodium hydroxide dissolved in 1.5 mL of water, 2.4 mmol) was added, and the mixture was stirred at 80 ° C. for 3 hours. The reaction mixture was poured into water and acidified with hydrochloric acid. The precipitated solid was collected by filtration, washed with water and air dried. 0.56 g (1.6 mmol, yield 80%) of 3- (2-bromo-6-isopropylphenoxy) -6-chloro-4-pyridazinol (Compound No. 760) was obtained.
¹ H-NMR (60MHz, DMF-d ₇ ) δppm: 7.70-7.00 (3H, m), 6.89 (1H, s), 2.94 (1H, septet, J = 7.0Hz), 1.16 (6H, d, J = 7.0Hz).
Melting point (° C): 232-253 (dec.).

(Example 20)
3- (2-Bromo-6-tert-butylphenoxy) -6-chloro-4-pyridazinol (Compound No. 761)
(1) tert-Butyl-2-[(2-methoxyethoxy) methoxy] benzene
Suspend 4.80 g (120 mmol) of 60% sodium hydride in dry tetrahydrofuran (25 mL), and add dropwise a solution of 15.0 g (100 mmol) of 2-tert-butylphenol in dry tetrahydrofuran (80 mL) at 0 ° C. did. After stirring at 0 ° C. for 10 minutes, a solution of 14.9 g (119 mmol) of 2-methoxyethoxymethyl chloride in dry tetrahydrofuran (80 mL) was added dropwise. The reaction mixture was stirred for 4 hours 30 minutes under ice-cooling and left at room temperature overnight. To the reaction mixture, 1.20 g (30 mmol) of 60% sodium hydride and 3.8 g (30 mmol) of 2-methoxyethoxymethyl chloride were added at 0 ° C., and the mixture was stirred at 0 ° C. for 7 hours. The reaction mixture was poured into ice-cold water (250 mL) and extracted with ethyl acetate. The organic layers were combined, washed with 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was purified by silica gel column chromatography (eluted with hexane: ethyl acetate = 20: 1), and 19.7 g (82.8 g) of tert-butyl-2-[(2-methoxyethoxy) methoxy] benzene was obtained. Mmol, yield 82.8%).
(2) 1-bromo-3-tert-butyl-2-[(2-methoxyethoxy) methoxy] benzene 10.0 g of tert-butyl-2-[(2-methoxyethoxy) methoxy] benzene obtained from (1) (42.0 mmol) was dissolved in dry ether (120 mL), and 42.1 mL (64.4 mmol) of n-butyllithium hexane solution (1.53M) was added dropwise to the solution under ice cooling, followed by stirring for 3 hours under ice cooling. A solution of 14.8 g (126 mmol) of 90% cyanogen bromide in dry ether (20 mL) was added dropwise thereto. The reaction mixture was stirred for 3 hours under ice cooling, poured into ice cold water (300 mL), and extracted with ether. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (eluting with hexane: ethyl acetate = 20: 1) to give 1-bromo-3-tert-butyl-2-[(2-methoxyethoxy) methoxy] 8.48 g (26.8 mmol, yield 63.8%) of benzene was obtained.
(3) 2-Bromo-6-tert-butylphenol 8.38 g (26.4 mmol) of 1-bromo-3-tert-butyl-2-[(2-methoxyethoxy) methoxy] benzene obtained by (2) was added to dichloromethane ( 30 mL), and a solution of 9.03 g (79.2 mmol) of trifluoroacetic acid in dichloromethane (20 mL) was added to this solution and stirred overnight at room temperature. The reaction mixture was poured into ice-cold 1 mol / L hydrochloric acid and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (eluted with hexane) to obtain 5.68 g (24.8 mmol, yield 93.9%) of 2-bromo-6-tert-butylphenol.
(4) 3- (2-Bromo-6-tert-butylphenoxy) -6-fluoropyridazine (Step A-1)
2-Bromo-6-tert-butylphenol 4.84 g (21.1 mmol) obtained in (3) was dissolved in 1,4-dioxane (40 mL), and potassium tert-butoxide 3.55 g (31.7 mmol) and 1,4-dioxane were added to this solution. 4-dioxane (40 mL) was added and stirred at room temperature for 15 minutes. To this, 2.45 g (21.1 mmol) of 3,6-difluoropyridazine was added and heated under reflux for 24 hours. The reaction mixture was allowed to cool, poured into ice-cold water, and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate, gradient) to obtain 1.70 g of 3- (2-bromo-6-tert-butylphenoxy) -6-fluoropyridazine. (5.23 mmol, yield 24.8%).
(5) 6- (2-Bromo-6-tert-butylphenoxy) -3-pyridazinol 1.70 g of 3- (2-bromo-6-tert-butylphenoxy) -6-fluoropyridazine obtained by (4) ( To a mixture of 5.23 mmol) and acetic acid (9 mL) was added 1.04 g (10.6 mmol) of potassium acetate, and the mixture was stirred at 130-140 ° C. for 3 hours. The reaction mixture was allowed to cool, poured into ice-cold water, and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, the resulting residue was washed with benzene, and 1.54 g (4.77 mmol, 91.2% yield, mp 255-257) of 6- (2-bromo-6-tert-butylphenoxy) -3-pyridazinol. C).
(6) 3- (2-Bromo-6-tert-butylphenoxy) -6-chloropyridazine 1.54 g of 6- (2-bromo-6-tert-butylphenoxy) -3-pyridazinol obtained from (5) ( 4.77 mmol) was mixed with 15 mL (162 mmol) phosphorus oxychloride and the mixture was heated to reflux for 70 minutes. Phosphorus oxychloride was distilled off from the reaction mixture, poured into ice-cold water, and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 1.55 g (4.53 mmol, yield 95.0%) of 3- (2-bromo-6-tert-butylphenoxy) -6-chloropyridazine.
(7) Mixture of 3- (2-bromo-6-tert-butylphenoxy) -6-chloropyridazine 1-oxide and 6- (2-bromo-6-tert-butylphenoxy) -3-chloropyridazine 1-oxide (Process C-1)
1.42 g (4.15 mmol) of 3- (2-bromo-6-tert-butylphenoxy) -6-chloropyridazine obtained in (6) was dissolved in dry dichloromethane (20 mL), and 80% m-chloroperoxide was added to this solution. A solution of 1.08 g (4.99 mmol) of benzoic acid in dry dichloromethane (10 mL) was added, and the mixture was heated to reflux for 20 hours. To the reaction mixture was added 0.275 g (1.27 mmol) of 80% m-chloroperbenzoic acid, and the mixture was refluxed for 3 hours and 30 minutes, poured into a 1 mol / L aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1) to give 3- (2-bromo-6-tert-butylphenoxy) -6-chloropyridazine 1 0.704 g (1.97 mmol, yield 47.5%) of a mixture of 2-oxide and 6- (2-bromo-6-tert-butylphenoxy) -3-chloropyridazine 1-oxide was obtained.
(8) 3- (2-bromo-6-tert-butylphenoxy) -4,6-dichloropyridazine and 6- (2-bromo-6-tert-butylphenoxy) -3,4-dichloropyridazine (Step C- 2)
3- (2-Bromo-6-tert-butylphenoxy) -6-chloropyridazine 1-oxide and 6- (2-bromo-6-tert-butylphenoxy) -3-chloropyridazine 1 obtained by (7) 0.704 g (1.97 mmol) of the oxide mixture was mixed with 5 mL (54 mmol) of phosphorus oxychloride and the mixture was heated to reflux for 2 hours. The reaction mixture was allowed to cool, poured into ice-cold water, and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate = 20: 1) to give 3- (2-bromo-6-tert-butylphenoxy) -4,6-dichloro 0.474 g (1.26 mmol, yield 64.0%) of pyridazine and 0.119 g (0.316 mmol, yield 16.0%) of 6- (2-bromo-6-tert-butylphenoxy) -3,4-dichloropyridazine were obtained.
(9) 3- (2-Bromo-6-tert-butylphenoxy) -6-chloro-4-methoxypyridazine (Step C-3)
3- (2-Bromo-6-tert-butylphenoxy) -4,6-dichloropyridazine obtained by (8) was dissolved in 0.443 g (1.18 mmol) of methanol (10 mL), and 28% sodium methoxy was dissolved in this solution. 0.545 g (2.83 mmol) of de-methanol solution and methanol (5 mL) were added and stirred at room temperature for 80 minutes. After adding 0.10 g (0.52 mmol) of 28% sodium methoxide-methanol solution to the reaction mixture and stirring at room temperature for 2 hours, 0.15 g (0.78 mmol) of 28% sodium methoxide-methanol solution was further added at room temperature. Stir overnight. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 0.428 g (1.15 mmol, yield 97.5%) of 3- (2-bromo-6-tert-butylphenoxy) -6-chloro-4-methoxypyridazine.
(10) 3- (2-Bromo-6-tert-butylphenoxy) -6-chloro-4-pyridazinol (Compound No. 761, Step C-4)
3- (2-Bromo-6-tert-butylphenoxy) -6-chloro-4-methoxypyridazine (0.395 g, 1.06 mmol) obtained in (9) was dissolved in dimethyl sulfoxide (5 mL), and the solution was hydroxylated. An aqueous sodium solution (prepared by dissolving 50.8 mg of sodium hydroxide in 3 mL of water, 1.27 mmol) was added, and the mixture was stirred at 80 ° C. for 3 hr. An aqueous sodium hydroxide solution (prepared by dissolving 42 mg of sodium hydroxide in 3 mL of water, 1.1 mmol) and dimethyl sulfoxide (10 mL) were added, and the mixture was further stirred at 80 ° C. for 5 hours. After allowing to cool, the reaction mixture was poured into ice-cold water and acidified with hydrochloric acid. The precipitated solid was collected by filtration, washed successively with water, hexane and isopropyl ether and air dried. 0.309 g (0.863 mmol, yield 81.4%) of 3- (2-bromo-6-tert-butylphenoxy) -6-chloro-4-pyridazinol (Compound No. 761) was obtained.
¹ H-NMR (270 MHz, CDCl ₃ ) δ ppm: 9.55 (1H, br.s), 7.47 (1H, dd, J = 8.1, 1.7 Hz), 7.41 (1H, dd, J = 8.1, 1.7 Hz), 7.08 (1H, t, J = 8.1Hz), 6.58 (1H, br.s), 1.34 (9H, s).
Melting point (° C): 240-247.

(Example 21)
6-Chloro-3- (2,6-dimethylphenoxy) -4-pyridazinol (Compound No. 801)
(1) 6-chloro-3- (2,6-dimethylphenoxy) pyridazine 1-oxide (step B-2)
268 mg (2.20 mmol) of 2,6-dimethylphenol, 1,4-dioxane (3 mL) and dimethyl sulfoxide (3 mL) were mixed, and 270 mg (2.41 mmol) of potassium tert-butoxide was added to the mixture under ice cooling. Stir for minutes. Thereto was added 370 mg (2.24 mmol) of 3,6-dichloropyridazine 1-oxide, and the mixture was stirred at room temperature for 10 hours and allowed to stand for 2 days. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was purified by silica gel column chromatography (hexane: ethyl acetate, gradient), and 350 mg (1.39 mmol, 6-chloro-3- (2,6-dimethylphenoxy) pyridazine 1-oxide was collected. Rate 63.1%).
(2) 4,6-Dichloro-3- (2,6-dimethylphenoxy) pyridazine (Step B-3)
6-chloro-3- (2,6-dimethylphenoxy) pyridazine 1-oxide 330 mg (1.31 mmol) obtained by (1) was mixed with dichloromethane (0.6 mL) and phosphorus oxychloride 0.60 mL (6.5 mmol), The mixture was stirred for 1 hour and left for another 5 days. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was purified by silica gel column chromatography (hexane: ethyl acetate, gradient), and 322 mg (1.20 mmol, yield) of 4,6-dichloro-3- (2,6-dimethylphenoxy) pyridazine 91.6%).
(3) 6-chloro-3- (2,6-dimethylphenoxy) -4-pyridazinol (Compound No. 801, Step B-4)
300 mg (1.12 mmol) of 4,6-dichloro-3- (2,6-dimethylphenoxy) pyridazine obtained in (2) was dissolved in dimethyl sulfoxide (8 mL), and 10% (W / V) water was added to this solution. Sodium oxide aqueous solution 0.80mL (2.0 mmol) was added, and it stirred at room temperature overnight. Further, 0.80 mL (2.0 mmol) of 10% (W / V) aqueous sodium hydroxide solution was added, and after the disappearance of the raw materials, the reaction mixture was poured into ice-cold water. The mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate, gradient) and preparative thin layer chromatography (Merck, 1.05744, developed in dichloromethane: methanol = 9: 1), 128 mg (0.510 mmol, yield 45.5%) of 6-chloro-3- (2,6-dimethylphenoxy) -4-pyridazinol (Compound No. 801) was obtained.
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.18-7.05 (3H, m), 6.83 (1H, s), 2.05 (6H, s).
Melting point (° C): 214-215.

(Example 22)
3- (2-tert-Butyl-6-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 805)
(1) 3- (2-tert-butyl-6-methylphenoxy) -6-chloropyridazine (Step A-1)
17.5 g (107 mmol) of 2-tert-butyl-6-methylphenol, 11.9 g (106 mmol) of potassium tert-butoxide and 1,4-dioxane (250 mL) were mixed, and the mixture was stirred at room temperature for 30 minutes. To this was added 15.0 g (101 mmol) of 2,6-dichloropyridazine, and the mixture was stirred at 100 ° C. for 3 hours and 15 minutes. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was crystallized from isopropyl ether to obtain 15.3 g (55.2 mmol, yield 54.6%) of 3- (2-tert-butyl-6-methylphenoxy) -6-chloropyridazine.
(2) 3- (2-tert-butyl-6-methylphenoxy) -6-chloropyridazine 1-oxide (step C-1)
3- (2-tert-butyl-6-methylphenoxy) -6-chloropyridazine (8.00 g, 28.9 mmol) obtained by (1) was added to dry dichloromethane (200 mL) and 70% m-chloroperbenzoic acid (8.50 g) ( 34.4 mmol) and the mixture was stirred at room temperature for 4 days. The reaction mixture was poured into ice-cold saturated aqueous sodium sulfite and extracted with dichloromethane. The organic layers were combined, washed sequentially with water and brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was crystallized from an ether-hexane mixed solvent or purified by silica gel column chromatography, and 3- (2-tert-butyl-6-methylphenoxy) -6-chloropyridazine 1-oxide 7.04 g (24.0 mmol, yield 83.0%) was obtained.
(3) 3- (2-tert-butyl-6-methylphenoxy) -4,6-dichloropyridazine (Step C-2)
1.00 g (3.41 mmol) of 3- (2-tert-butyl-6-methylphenoxy) -6-chloropyridazine 1-oxide obtained by (2) was added to chloroform (10 mL) and 0.48 mL (5.2 mmol) of phosphorus oxychloride. And the mixture was stirred at reflux for 24 hours and at room temperature for 2 days. The reaction mixture was poured into ice cold water and extracted with dichloromethane. The organic layers were combined, washed successively with saturated aqueous sodium hydrogen carbonate solution, water and brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was crystallized from an ether-hexane mixed solvent. 0.767 g (2.47 mmol, yield 72.4%) of 3- (2-tert-butyl-6-methylphenoxy) -4,6-dichloropyridazine Got.
(4) 3- (2-tert-Butyl-6-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 805, Step C-3)
354 mg (1.14 mmol) of 3- (2-tert-butyl-6-methylphenoxy) -4,6-dichloropyridazine obtained in (3), dimethyl sulfoxide (10 mL) and 1.6 mL of 1 mol / L aqueous sodium hydroxide solution (1.6 mmol) and the mixture was stirred at room temperature for 2 hours 30 minutes. The reaction mixture was poured into ice cold water and washed with ether. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was crystallized with a mixed solvent of ether-hexane, and 172 mg (0.587 mmol) of 3- (2-tert-butyl-6-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 805) was obtained. Yield 51.5%).
¹ H-NMR (90 MHz, CDCl ₃ ) δ ppm: 7.35-6.80 (3H, m), 6.50 (1H, s), 1.80 (3H, s), 1.18 (9H, s).
Melting point (° C): 135-136.

(Example 23)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol (Compound No. 806)
(1) 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-cyclopropyl-6-methylphenoxy) pyridazine 1-oxide (Step B- 2)
2-Cyclopropyl-6-methylphenol 221 mg (1.49 mmol) was mixed with 1,4-dioxane (2 mL) and dimethyl sulfoxide (2 mL). Under ice cooling, 184 mg (1.64 mmol) of potassium tert-butoxide was added to the mixture. Added and stirred for 10 minutes. Thereto was added 258 mg (1.56 mmol) of 3,6-dichloropyridazine 1-oxide, and the mixture was stirred at room temperature for 10 hours and allowed to stand for 3 days. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate, gradient) to give 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) pyridazine 1-oxide and 3-chloro 222 mg (0.801 mmol, yield 53.8%) of a mixture of -6- (2-cyclopropyl-6-methylphenoxy) pyridazine 1-oxide was obtained.
(2) 4,6-Dichloro-3- (2-cyclopropyl-6-methylphenoxy) pyridazine (Step B-3)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-cyclopropyl-6-methylphenoxy) pyridazine 1-oxide obtained by (1) 210 mg (0.758 mmol) of the above mixture was dissolved in chloroform (1 mL). To this solution was added 0.106 mL (1.14 mmol) of phosphorus oxychloride, and most of the chloroform was distilled off with a nitrogen stream, followed by stirring at room temperature for 2 days. . Further, chloroform (2 mL) and 0.150 mL (1.62 mmol) of phosphorus oxychloride were added, and most of chloroform was distilled off with a nitrogen stream, followed by stirring for 3 hours. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was purified by silica gel column chromatography (hexane: ethyl acetate, gradient), and 167 mg (0.566 mmol) of 4,6-dichloro-3- (2-cyclopropyl-6-methylphenoxy) pyridazine was obtained. Yield 74.7%).
(3) 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol (Compound No. 806, Step B-4)
150 mg (0.508 mmol) of 4,6-dichloro-3- (2-cyclopropyl-6-methylphenoxy) pyridazine obtained in (2) was dissolved in dimethyl sulfoxide (3 mL), and 10% (W / V ) A sodium hydroxide aqueous solution (0.37 mL, 0.925 mmol) was added, and the mixture was stirred at room temperature for 4 days. The reaction mixture was poured into ice-cold 5% aqueous sodium hydroxide and extracted with ether. The aqueous layer was acidified with hydrochloric acid and extracted with ether. The organic layer was dried and concentrated. The residue was purified by preparative thin layer chromatography (Merck, 1.05744, developed with dichloromethane: methanol = 20: 1) and 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4 -Pyridazinol (Compound No. 806) was obtained in an amount of 114 mg (0.412 mmol, yield 81.1%).
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.13-7.03 (2H, m), 6.84-6.79 (2H, m), 2.06 (3H, s), 1.83-1.68 (1H, m), 0.82- 0.72 (2H, m), 0.64-0.51 (2H, m).
Melting point (° C): 201-202.

(Example 24)
6-Chloro-3- [2- (2,2-dichlorocyclopropyl) -6-methylphenoxy] -4-pyridazinol (Compound No. 827)
(1) 1- (2,2-dichlorocyclopropyl) -2-methoxy-3-methylbenzene
2-Methoxy-1-methyl-3-vinylbenzene (304 mg, 2.05 mmol) was dissolved in chloroform (12 mL), and 50 mL of 50% aqueous sodium hydroxide solution (63 mmol) was added dropwise to this solution, followed by benzyl (triethyl) ammonium. 59.9 mg (0.263 mmol) of chloride was added and stirred at room temperature overnight. The reaction mixture was poured into water and extracted with chloroform. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed with hexane: ethyl acetate = 4: 1), and 1- (2, 390 mg (1.69 mmol, yield 82.4%) of 2-dichlorocyclopropyl) -2-methoxy-3-methylbenzene was obtained.
(2) 2- (2,2-dichlorocyclopropyl) -6-methylphenol 102 mg (0.442 mmol) of 1- (2,2-dichlorocyclopropyl) -2-methoxy-3-methylbenzene obtained from (1) ) Was dissolved in dichloromethane (5 mL), the solution was ice-cooled, and 0.045 mL (0.47 mmol) of boron tribromide was added dropwise with stirring. The reaction mixture was stirred for 2 hours under ice-cooling, poured into water, and extracted with dichloromethane. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 2 plates used, developed with hexane: ethyl acetate = 2: 1), and 2- (2, 76.9 mg (0.354 mmol, yield 80.1%) of 2-dichlorocyclopropyl) -6-methylphenol was obtained.
(3) 6-chloro-3- [2- (2,2-dichlorocyclopropyl) -6-methylphenoxy] pyridazine 1-oxide (step B-2)
198 mg (0.912 mmol) of 2- (2,2-dichlorocyclopropyl) -6-methylphenol obtained by (2) was mixed with 1,4-dioxane (3 mL) and dimethyl sulfoxide (3 mL). Under ice cooling, 113 mg (1.01 mmol) of potassium tert-butoxide was added and stirred for 10 minutes. Thereto was added 151 mg (0.915 mmol) of 3,6-dichloropyridazine 1-oxide, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed 3 times with hexane: ethyl acetate = 2: 1), and 6-chloro-3- 257 mg of a crude product of [2- (2,2-dichlorocyclopropyl) -6-methylphenoxy] pyridazine 1-oxide was obtained.
(4) 4,6-Dichloro-3- [2- (2,2-dichlorocyclopropyl) -6-methylphenoxy] pyridazine (Step B-3)
The crude product of 6-chloro-3- [2- (2,2-dichlorocyclopropyl) -6-methylphenoxy] pyridazine 1-oxide obtained in (3) was mixed with phosphorus oxychloride (3 mL). The mixture was stirred overnight at room temperature. Water and dichloromethane were added to the reaction mixture and stirred for 30 minutes. The mixture was separated, and the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin layer chromatography (MERCK, 1.05744, 3 plates used, developed with hexane: ethyl acetate = 2: 1), and 4,6-dichloro-3- [2- (2,2-dichlorocyclopropyl) -6-methylphenoxy] pyridazine 209 mg (0.574 mmol, 2-step yield from 2- (2,2-dichlorocyclopropyl) -6-methylphenol, 62.9% )Obtained.
(5) 6-chloro-3- [2- (2,2-dichlorocyclopropyl) -6-methylphenoxy] -4-pyridazinol (Compound No. 827, Step B-4)
209 mg (0.574 mmol) of 4,6-dichloro-3- [2- (2,2-dichlorocyclopropyl) -6-methylphenoxy] pyridazine obtained by (4) was added to 1,4-dioxane (3 mL) and dimethyl The mixture was mixed with sulfoxide (3 mL), and 1.43 mL (2.86 mmol) of a 2 mol / L aqueous sodium hydroxide solution was added to the mixture and stirred overnight at room temperature. The reaction mixture was poured into water and acidified with dilute hydrochloric acid. This mixture was extracted with dichloromethane. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed with ethyl acetate) to give 6-chloro-3- [2- (2,2- 120 mg (0.349 mmol, yield 60.8%) of dichlorocyclopropyl) -6-methylphenoxy] -4-pyridazinol (Compound No. 827) was obtained.
¹ H-NMR (200MHz, CD ₃ OD) δppm: 7.25 (1H, br.d, J = 6.3Hz), 7.16 (1H, t, J = 7.7Hz), 6.98 (1H, d, J = 7.7Hz) , 6.72 (1H, s), 2.85 (1H, dd, J = 10.6, 8.8Hz), 2.22 (3H, s), 2.05-1.86 (2H, m).
Melting point (° C): 213-215.

(Example 25)
6-Chloro-3-[(5-methyl-1-benzofuran-4-yl) oxy] -4-pyridazinol (Compound No. 1109)
(1) 6,7-Dihydro-1-benzofuran-4 (5H) -one
11.2 g (0.100 mol) of 1,3-cyclohexanedione was dissolved in methanol (40 mL). To this solution, an aqueous solution (8 mL) of 6.60 g (0.100 mol) of 85% potassium hydroxide was added dropwise and stirred at room temperature for 30 minutes. This mixture was iced, and 21.6 g (0.110 mol) of a 40% aqueous chloroacetaldehyde solution was added with stirring, followed by stirring overnight at room temperature. A 2 mol / L aqueous hydrochloric acid solution was added dropwise to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes, and then extracted with ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 6,7-dihydro-1-benzofuran-4 (5H) -one. 8.63 g (0.0635 mol, yield 63.5%) was obtained.
(2) Methyl 4-oxo-4,5,6,7-tetrahydro-1-benzofuran-5-carboxylate 6,7-dihydro-1-benzofuran-4 (5H) -one 3.00 obtained by (1) g (22.1 mmol) was dissolved in dry tetrahydrofuran (10 mL), and 48.5 mL (48.5 mmol) of lithium bis (trimethylsilyl) amide (1.0 M tetrahydrofuran solution) was added dropwise to this solution at −78 ° C. under a nitrogen stream. After stirring at −78 ° C. for 30 minutes, 1.87 mL (24.1 mmol) of methyl chlorocarbonate was added dropwise, and the reaction mixture was allowed to warm to room temperature and stirred for 10 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain methyl 4-oxo-4,5,6,7-tetrahydro-1- 3.93 g (20.3 mmol, yield 91.9%) of benzofuran-5-carboxylate was obtained.
(3) Methyl 4-hydroxy-1-benzofuran-5-carboxylate 3.93 g of methyl 4-oxo-4,5,6,7-tetrahydro-1-benzofuran-5-carboxylate obtained from (2) (20.3 Mmol) was dissolved in 1,4-dioxane (100 mL). To this solution, 5.51 g (24.3 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was added and stirred at 120 ° C. for 3 hours. . The reaction mixture was allowed to cool, insoluble material was filtered off through celite, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 2.04 g (10.6 mmol, yield 52.2%) of methyl 4-hydroxy-1-benzofuran-5-carboxylate. It was.
(4) Methyl 4-methoxy-1-benzofuran-5-carboxylate Methyl 4-hydroxy-1-benzofuran-5-carboxylate obtained by (3) was added to a solution of 2.04 g (10.6 mmol) in acetonitrile (60 mL). Then, 2.53 g (18.3 mmol) of potassium carbonate and 2.85 mL (45.8 mmol) of methyl iodide were added, and the mixture was heated to reflux for 3 hours. After standing at room temperature overnight, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 2.01 g of methyl 4-methoxy-1-benzofuran-5-carboxylate ( 9.76 mmol, yield 92.1%).
(5) (4-Methoxy-1-benzofuran-5-yl) methanol A solution of 1.01 g (4.90 mmol) of methyl 4-methoxy-1-benzofuran-5-carboxylate obtained in (4) in dry tetrahydrofuran (20 mL) To the solution, 0.479 g (12.6 mmol) of lithium aluminum hydride was added little by little with stirring on ice. The reaction mixture was stirred for 2 hours under ice cooling, and ethyl acetate was added little by little. Subsequently, water (0.5 mL), 3N sodium hydroxide (0.5 mL), and water (1.5 mL) were sequentially added, and the mixture was stirred for 30 minutes. The mixture was filtered through celite, and the filtrate was concentrated to give 0.89 g of a crude product of (4-methoxy-1-benzofuran-5-yl) methanol.
(6) 4-Methoxy-5-methyl-1-benzofuran 0.65 g of the crude product of (4-methoxy-1-benzofuran-5-yl) methanol obtained from (5) was dissolved in dichloromethane (10 mL). To the solution, 0.56 mL (4.03 mmol) of triethylamine and 0.31 mL (3.99 mmol) of methanesulfonyl chloride were added dropwise with stirring under ice cooling, followed by stirring for 1 hour under ice cooling. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, dry dimethyl sulfoxide (20 mL) was added to the obtained residue, and 0.276 g (7.30 mmol) of sodium borohydride was added little by little. The mixture was stirred at room temperature for 1 hour, poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05717, 3 plates used, developed with hexane: ethyl acetate = 9: 1), and 4-methoxy-5 0.284 g (1.75 mmol, 48.9% yield from methyl 4-methoxy-1-benzofuran-5-carboxylate) was obtained.
(7) 5-Methyl-1-benzofuran-4-ol
268 mg (6.71 mmol) of 60% sodium hydride was suspended in dry N, N-dimethylformamide (11 mL), and 0.51 mL (6.9 mmol) of ethanethiol was added dropwise to the suspension under a nitrogen gas stream. Stir for minutes. To this was added a solution of 4-methoxy-5-methyl-1-benzofuran 362 mg (2.23 mmol) obtained in (6) in N, N-dimethylformamide (7 mL), and the mixture was heated to reflux for 1 hour 30 minutes. The reaction mixture was allowed to cool, and 1 mol / L aqueous potassium hydroxide solution and diethyl ether were added. The aqueous layer was washed with diethyl ether and adjusted to pH 2 by adding dilute hydrochloric acid. This was extracted with diethyl ether, and the obtained organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (development using MERCK 1.05744, 3 hexanes: ethyl acetate = 2: 1), and 5-methyl-1-benzofuran- 276 mg (1.86 mmol, yield 83.4%) of 4-ol was obtained.
(8) 6-chloro-3-[(5-methyl-1-benzofuran-4-yl) oxy] pyridazine 1-oxide (step B-2)
121 mg (0.818 mmol) of 5-methyl-1-benzofuran-4-ol obtained in (7) was mixed with 1,4-dioxane (3 mL) and dimethyl sulfoxide (3 mL). 101 mg (0.902 mmol) of tert-butoxide was added and stirred for 10 minutes. Thereto was added 134 mg (0.812 mmol) of 3,6-dichloropyridazine 1-oxide, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed 3 times with hexane: ethyl acetate = 2: 1), and 6-chloro-3- 199 mg of a crude product of [(5-methyl-1-benzofuran-4-yl) oxy] pyridazine 1-oxide was obtained.
(9) 4,6-Dichloro-3-[(5-methyl-1-benzofuran-4-yl) oxy] pyridazine (Step B-3)
199 mg of a crude product of 6-chloro-3-[(5-methyl-1-benzofuran-4-yl) oxy] pyridazine 1-oxide obtained by (8) and 3 mL of phosphorus oxychloride were mixed, and this mixture was mixed. Stir at room temperature overnight. Water and dichloromethane were added to the reaction mixture and stirred for 30 minutes. The mixture was separated, and the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was subjected to preparative thin layer chromatography (MERCK, 1.05744, 3 plates, hexane: ethyl acetate = 2: 1, developed 3 times, then MERCK, 1.05717, 2 plates) Use, hexane: ethyl acetate = 2: 1, developed three times), and 4,6-dichloro-3-[(5-methyl-1-benzofuran-4-yl) oxy] pyridazine 120 mg (0.407 mmol) 4-hydroxy-5-methyl-1-benzofuran, yield of 2 steps, 49.8%).
(10) 6-Chloro-3-[(5-methyl-1-benzofuran-4-yl) oxy] -4-pyridazinol (Compound No. 1109, Step B-4)
120 mg (0.407 mmol) of 4,6-dichloro-3-[(5-methyl-1-benzofuran-4-yl) oxy] pyridazine obtained by (9) was added to 1,4-dioxane (3 mL) and dimethyl sulfoxide ( 3 mL), 2 mol / L aqueous sodium hydroxide solution (1.01 mL, 2.02 mmol) was added to the mixture, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water and acidified with dilute hydrochloric acid. This mixture was extracted with dichloromethane. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 2 plates used, developed with ethyl acetate), and 6-chloro-3-[(5-methyl-1- 70.0 mg (0.253 mmol, 62.2% yield) of benzofuran-4-yl) oxy] -4-pyridazinol (Compound No. 1109) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.65 (1H, d, J = 2.2 Hz), 7.32 (1H, d, J = 8.8 Hz), 7.18 (1H, d, J = 8.8 Hz), 6.73 (1H, s), 6.60 (1H, dd, J = 2.2, 0.7Hz), 2.23 (3H, s).
Melting point (° C): 222-225.

(Example 26)
6-chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl trifluoromethanesulfonate (Compound No. 2081, Step I-1)
50.3 mg (0.191 mmol) of 6-chloro-3- (2-cyclopropylphenoxy) -4-pyridazinol (Compound No. 139) obtained according to Example 6 was dissolved in methylene chloride (2 mL), and triethylamine 0.027 was dissolved in this solution. mL (0.19 mmol) was added dropwise, then 0.031 mL (0.19 mmol) of trifluoromethanesulfonic anhydride was added dropwise, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was directly purified by preparative thin-layer chromatography (MERCK, 1.05744, using 2 plates, developed with ethyl acetate: hexane = 2: 1) to give 6-chloro-3- (2-cyclopropyl 64.7 mg (0.164 mmol, yield 85.8%) of phenoxy) -4-pyridazinyl trifluoromethanesulfonate (Compound No. 2081) was obtained.
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.51 (1H, s), 7.26-7.19 (2H, m), 7.14-7.05 (2H, m), 1.89-1.81 (1H, m), 0.85-0.62 ( 4H, m).
Melting point (° C): 54-61.

(Example 27)
6-chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2225, Step I-1)
53.4 mg (0.203 mmol) of 6-chloro-3- (2-cyclopropylphenoxy) -4-pyridazinol (Compound No. 139) obtained according to Example 6 was dissolved in acetonitrile (3 mL). -Diazabicyclo [2.2.2] octane (23.1 mg, 0.206 mmol) was added, followed by 4-methylbenzenesulfonyl chloride (39.2 mg, 0.205 mmol), and the mixture was stirred at room temperature for 1 hour and 30 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (MERCK, 1.05744, developed with ethyl acetate: hexane = 2: 1) to give 6-chloro-3- (2- 68.8 mg (0.165 mmol, 81.3% yield) of cyclopropylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2225) was obtained.
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.87 (2H, d, J = 8.1Hz), 7.58 (1H, s), 7.36 (2H, d, J = 8.1Hz), 7.26-7.11 (2H, m ), 6.97-6.93 (1H, m), 6.74-6.70 (1H, m), 2.45 (3H, s), 1.67-1.59 (1H, m), 0.71-0.56 (4H, m).
Physical property: Oily substance.

(Example 28)
2-[(6-Chloro-4-{[(4-methylphenyl) sulfonyl] oxy} -3-pyridazinyl) oxy] phenyl 4-methylbenzenesulfonate (Compound No. 2233, Step I-1)
6-Chloro-3- (2-hydroxyphenoxy) -4-pyridazinol (Compound No. 384) 0.60 g (2.5 mmol) obtained in Example 10, 4-methylbenzenesulfonyl chloride 1.06 g (5.5 mmol), 1, 4-Diazabicyclo [2.2.2] octane (0.56 g, 5.0 mmol) and acetonitrile (30 mL) were mixed, and the mixture was stirred with heating under reflux for 3 hours and at room temperature for 4 days. Acetonitrile was distilled off, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was washed with a mixed solvent of hexane-ethyl acetate (3: 1) to give 2-[(6-chloro-4-{[(4-methylphenyl) sulfonyl] oxy} -3-pyridazinyl ) Oxy] phenyl 4-methylbenzenesulfonate (Compound No. 2233) was obtained in an amount of 1.0 g (1.8 mmol, yield 72%).
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 7.98-6.65 (13H, m), 2.40 (3H, s), 2.36 (3H, s).
Melting point (° C): 125.5-126.5.

(Example 29)
6-Chloro-5-methyl-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 2372)
(1) 3-chloro-4-methyl-2,5-furandion and 3-chloro-4- (chloromethyl) -2,5-furandion
224 g (2.00 mol) of 3-methyl-2,5-furandione and 11.2 g (0.415 mol) of iron (III) chloride hexahydrate were mixed, and the mixture was heated to 140 ° C. and 346 g of chlorine gas was stirred. (4.88 mol) was blown in over 7 hours 30 minutes. The mixture was then heated at 175 ° C. for 3 hours 30 minutes. The reaction mixture was distilled under reduced pressure (5 mmHg) to collect a fraction at 80 ° C to 85 ° C. 223.5 g of crude product (including 3-chloro-4-methyl-2,5-furandion and 3-chloro-4- (chloromethyl) -2,5-furandion) was obtained.
(2) 4-chloro-5-methyl-1,2-dihydro-3,6-pyridazinedione and 4-chloro-5- (chloromethyl) -1,2-dihydro-3,6-pyridazinedione (1) 147 g (including 3-chloro-4-methyl-2,5-furandione and 3-chloro-4- (chloromethyl) -2,5-furandione) obtained by mixing with 400 ml of water, this mixture Was heated to reflux to give a solution. To this heated and refluxed solution, an aqueous solution of 116 g (1.10 mol) of hydrazine dihydrochloride (dissolved in 400 mL of water) was added dropwise over 40 minutes. Thereafter, the mixture was heated to reflux for 1 hour 30 minutes and allowed to cool. The precipitated crystals were collected by filtration and washed with hot water and then with ethyl acetate to obtain 81.8 g of 4-chloro-5-methyl-1,2-dihydro-3,6-pyridazinedione (mp305-310 ° C.). . On the other hand, the filtrate was extracted with ethyl acetate, and the organic layers were combined, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and 8.06 g of a mixture containing 4-chloro-5- (chloromethyl) -1,2-dihydro-3,6-pyridazinedione as a residue was obtained.
(3) 3,4,6-Trichloro-5-methylpyridazine Oxygenate 24.1 g (0.150 mol) of 4-chloro-5-methyl-1,2-dihydro-3,6-pyridazinedione obtained from (2) The mixture was mixed with 250 mL (2.76 mol) of phosphorus chloride, and the mixture was heated to reflux for 1 hour and 40 minutes. Excess phosphorus oxychloride was distilled off from the reaction mixture, and the residue was mixed with ice water. The crystals were collected by filtration and extracted with ethyl acetate. The organic layer was washed with water and the solvent was distilled off. The obtained residue was distilled under reduced pressure (0.7 mmHg), and the fraction at 105 ° C to 110 ° C was collected, and 25.1 g (0.127 mol, yield 84.7%, mp67) of 3,4,6-trichloro-5-methylpyridazine was collected. .5-70 ° C).
(4) 3,6-dichloro-4-methoxy-5-methylpyridazine 3.90 g (40.1 mmol) of 3,4,6-trichloro-5-methylpyridazine obtained from (3) was mixed with methanol (100 mL). To this mixture was added dropwise a methanol solution (50 mL) of 0.92 g (40 mmol) of sodium under ice cooling, and then the mixture was stirred for 1 hour under ice cooling and 15 minutes under heating and reflux. Under ice cooling, 0.20 g (8.7 mmol) of sodium was added, and the mixture was further heated to reflux for 15 minutes. The reaction solution was allowed to cool and methanol was distilled off. The residue was mixed with ice water and extracted with ethyl acetate. The organic layers were combined and washed with water, and the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (eluted with Wakogel C-100, hexane: ethyl acetate = 5: 1) to obtain 5.1 g of a crude product. This was distilled under reduced pressure (0.07 mmHg), and a fraction at 125 ° C. was collected to obtain 4.50 g (23.3 mmol, yield 58.1%) of 3,6-dichloro-4-methoxy-5-methylpyridazine.
(5) Mixture of 3-chloro-5-methoxy-4-methyl-6- (2-methylphenoxy) pyridazine and 3-chloro-4-methoxy-5-methyl-6- (2-methylphenoxy) pyridazine (process) D-1)
While stirring, 1.66 g (38.0 mmol) of 55% sodium hydride was gradually added to 30.8 g (285 mmol) of 2-methylphenol. After stirring at room temperature for 20 minutes, the mixture was heated to 90 ° C. and the sodium hydride solid disappeared. The mixture was cooled to 50 ° C., 3.69 g (19.1 mmol) of 3,6-dichloro-4-methoxy-5-methylpyridazine obtained in (4) was added, and the mixture was stirred at 110 ° C. for 3 hours and 30 minutes. The reaction mixture was allowed to cool, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with 20% aqueous sodium hydroxide and the solvent was distilled off. The obtained residue was purified by silica gel column chromatography to obtain 3-chloro-5-methoxy-4-methyl-6- (2-methylphenoxy) pyridazine and 3-chloro-4-methoxy-5-methyl-6- 1.38 g (5.21 mmol, yield 27.3%) of a mixture of (2-methylphenoxy) pyridazine was obtained.
(6) 6-chloro-5-methyl-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 2372, Step D-2)
3-chloro-5-methoxy-4-methyl-6- (2-methylphenoxy) pyridazine and 3-chloro-4-methoxy-5-methyl-6- (2-methylphenoxy) pyridazine obtained by (5) 1.38 g (5.21 mmol) of a mixture of the following was mixed with 1,4-dioxane (8 mL), and 0.282 g (6.78 mmol) of 96% sodium hydroxide in water (using 13 mL of water) was added to this mixture, and 4.5% at 110 ° C. Stir for hours. The reaction mixture was poured into water and extracted with ethyl acetate. The aqueous layer was acidified with hydrochloric acid, and the precipitated crystals were collected by filtration, and 0.249 g (0-2) of 6-chloro-5-methyl-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 2372) was collected.
.992 mmol, yield 19.0%, mp 209-213 ° C.).
¹ H-NMR (60 MHz, DMF-d ₇ ) δ ppm: 7.50-6.95 (4H, m), 2.28 (3H, m), 2.11 (3H, m).
Melting point (° C): 209-213.
Crystals precipitated from the filtrate were collected by filtration to obtain 0.187 g (0.745 mmol, yield 14.3%) of 3-chloro-5-methyl-6- (2-methylphenoxy) -4-pyridazinol. On the other hand, after drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off to recover 0.57 g of raw material (41% recovery rate).

(Example 30)
6-Chloro-5- (methoxymethyl) -3- (2-methylphenoxy) -4-pyridazinol (Compound No. 2378)
(1) 3,4,6-trichloro-5- (chloromethyl) pyridazine containing 4-chloro-5- (chloromethyl) -1,2-dihydro-3,6-pyridazinedione obtained in Example 29 To 7.8 g of the mixture, 50 mL of phosphorus oxychloride was added and heated to reflux for 1 hour. Excess phosphorus oxychloride was distilled off from the reaction mixture, and the residue was mixed with ice water. This mixture was extracted with ethyl acetate, and the organic layers were combined, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Merck, 9385, eluted with hexane: ethyl acetate = 10: 1) to obtain 3,4,6-trichloro-5- (chloro This gave 3.63 g (15.6 mmol, mp 102-104 ° C.) of methyl) pyridazine.
(2) 3,6-dichloro-4-methoxy-5- (methoxymethyl) pyridazine 2.32 g (10.0 mmol) of 3,4,6-trichloro-5- (chloromethyl) pyridazine obtained from (1) was methanolized. After being dissolved in (50 ml) by heating, the solution was cooled to −60 ° C. and a methanol solution of sodium methoxide (prepared from 0.23 g of sodium and 5 mL of methanol, 10.0 mmol) was added dropwise. The solution was stirred at −10 ° C. for 2 hours 30 minutes, and a methanol solution of sodium methoxide (prepared from 0.23 g of sodium and 5 mL of methanol, 10.0 mmol) was further added dropwise. After stirring at -10 ° C for 2 hours, the mixture was left overnight at room temperature. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (Merck, 9385, eluted with hexane: ethyl acetate = 5: 1) and 3,6-dichloro-4-methoxy-5- (methoxymethyl). ) 1.85 g (8.30 mmol, 83.0% yield, mp 28-32 ° C.) of pyridazine were obtained.
(3) 3-Chloro-5-methoxy-4- (methoxymethyl) -6- (2-methylphenoxy) pyridazine (Step D-1)
432 mg (4.00 mmol) of 2-methylphenol, methanol (20 mL) and 92 mg (4.0 mmol) of sodium were mixed and stirred at room temperature until sodium disappeared. Methanol of this mixture was distilled off, 50 mL of toluene was added to the residue, and the mixture was heated to reflux. This mixture was ice-cooled, and a toluene solution (10 mL) of 3,6-dichloro-4-methoxy-5- (methoxymethyl) pyridazine obtained in (2) in 892 mg (4.00 mmol) was added dropwise and heated to reflux for 3 hours. . The reaction mixture was allowed to stand overnight at room temperature, washed with water and then with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was subjected to silica gel column chromatography (first time; elution with Merck, 9385, hexane: ethyl acetate = 5: 1, second time; Merck, 9385, hexane: ethyl acetate = 8: 1) and 0.487 g (1.65 mmol, 41.3% yield) of 3-chloro-5-methoxy-4- (methoxymethyl) -6- (2-methylphenoxy) pyridazine, 3-chloro-4 0.266 g (0.902 mmol, yield 22.6%) of -methoxy-5- (methoxymethyl) -6- (2-methylphenoxy) pyridazine was obtained.
(4) 6-chloro-5- (methoxymethyl) -3- (2-methylphenoxy) -4-pyridazinol (Compound No. 2378, Step D-2)
3-Chloro-5-methoxy-4- (methoxymethyl) -6- (2-methylphenoxy) pyridazine obtained by (3) 0.354 g (1.20 mmol), 1,4-dioxane (2 mL), 96% water Sodium oxide (62 mg, 1.49 mmol) and water (8 mL) were mixed, and the mixture was stirred at room temperature for 2 days and further with heating under reflux for 3 hours. The reaction mixture was adjusted to pH 1 with hydrochloric acid, and extracted with ethyl acetate. The organic layers were combined, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 0.336 g (1.20 mmol, 100% yield) of 6-chloro-5- (methoxymethyl) -3- (2-methylphenoxy) -4-pyridazinol (Compound No. 2378).
¹ H-NMR (60 MHz, DMF-d ₇ ) δppm: 8.92 (1H, br.s), 7.45-6.80 (4H, m), 4.39 (2H, s), 3.25 (3H, s), 2.25 (3H, s).
Melting point (° C): 123-126.

(Example 31)
Ethyl 6- (2-tert-butylphenoxy) -3-chloro-5-hydroxy-4-pyridazinecarboxylate (Compound No. 2386)
(1) 3- (2-tert-Butylphenoxy) -6-chloro-4-methoxypyridazine
5.87 g (39.1 mmol) of 2-tert-butylphenol, dimethyl sulfoxide (80 mL) and 4.38 g (39.0 mmol) of potassium t-butoxide were mixed, and the mixture was stirred at room temperature for 20 minutes. To this mixture, 6.92 g (38.7 mmol) of a dimethyl sulfoxide solution (60 mL) of 3,6-dichloro-4-methoxypyridazine was added and stirred at room temperature for 40 minutes and at 80 ° C. for 45 minutes. The reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layers were combined, washed with water and then with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Merck, 9385, hexane: ethyl acetate, gradient) to give 3- (2-tert-butylphenoxy) -6-chloro-4-methoxypyridazine 2.66 g (9.09 mmol, yield 23.5%) and 6- (2-tert-butylphenoxy) -3-chloro-4-methoxypyridazine 1.82 g (6.22 mmol, yield 16.1%).
(2) Ethyl 6- (2-tert-butylphenoxy) -3-chloro-5-methoxy-4-pyridazinecarboxylate (Step G-1)
3- (2-tert-Butylphenoxy) -6-chloro-4-methoxypyridazine 783 mg (2.68 mmol) obtained in (1) was dissolved in dry tetrahydrofuran (26 mL), and the solution was cooled to -78 ° C. 1.20 mL (2.80 mmol) of n-butyllithium hexane solution (2.33M) was added and stirred for 20 minutes. To this was added 0.330 mL (3.45 mmol) of ethyl chlorocarbonate, and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was poured into saturated aqueous ammonium chloride and extracted with ether. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (eluted with hexane: ethyl acetate = 5: 1) and purified with ethyl 6- (2-tert-butylphenoxy) -3-chloro-5-methoxy. 603 mg (1.65 mmol, yield 61.6%) of 4-pyridazinecarboxylate was obtained.
(3) Ethyl 6- (2-tert-butylphenoxy) -3-chloro-5-hydroxy-4-pyridazinecarboxylate (Compound No. 2386, Step G-2)
Ethyl 6- (2-tert-butylphenoxy) -3-chloro-5-methoxy-4-pyridazinecarboxylate 419 mg (1.15 mmol) obtained from (2), 1,4-dioxane, 1 mol / L sodium hydroxide An aqueous solution (2.0 mL, 2.0 mmol) and dimethyl sulfoxide (2.0 mL) were mixed, and the mixture was stirred at room temperature for 2 hours 30 minutes and at 80 ° C. for 4 hours 30 minutes. After allowing to cool, the reaction mixture was acidified with hydrochloric acid and extracted with dichloromethane. The organic layers were combined, washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography. Ethyl 6- (2-tert-butylphenoxy) -3-chloro-5-hydroxy-4-pyridazinecarboxylate (Compound No. 2386) (337 mg, 0.960) Mmol, yield 83.5%).
Physical properties: amorphous.

(Example 32)
3,6-bis (2-methylphenoxy) -4-pyridazinol (Compound No. 2395)
(1) 3-Chloro-5-methoxy-4,6-bis (2-methylphenoxy) pyridazine (Step D-1)
Dissolve 5.32 g (49.3 mmol) of 2-methylphenol in toluene (100 mL) and add 1.13 g (49.1 mmol) of sodium followed by 5.80 g (27.2 mmol) of 3,4,6-trichloro-5-methoxypyridazine to this solution. In addition, the mixture was stirred for 4 hours while heating under reflux. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate, gradient) and recrystallization from isopropyl ether to give 3-chloro-5-methoxy-4,6-bis (2-methylphenoxy). ) 3.0 g (8.4 mmol, 31% yield) of pyridazine was obtained.
(2) 6-chloro-3,5-bis (2-methylphenoxy) -4-pyridazinol (Compound No. 2395, Step D-2)
To a mixture of trimethylsilyl chloride 0.60 mL (4.7 mmol), sodium iodide 0.60 g (4.0 mmol) and acetonitrile (15 ml) 3-chloro-5-methoxy-4,6-bis (2-methyl) obtained by (1) 0.72 g (2.0 mmol) of phenoxy) pyridazine was added and stirred overnight. The reaction mixture was poured into ice cold water and extracted with methylene chloride. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (chloroform: methanol, gradient), and 0.45 g of 6-chloro-3,5- (2-methylphenoxy) -4-pyridazinol (Compound No. 2395) (1.3 mmol, yield 65%).
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.32-7.05 (7H, m), 6.91 (1H, br.d, J = 7.3 Hz), 2.29 (3H, s), 2.19 (3H, s).
Melting point (° C): 110-115.

(Example 33)
3- (2-tert-Butylphenoxy) -6-chloro-5- (trimethylsilyl) -4-pyridazinol (Compound No. 2405)
(1) 3- (2-tert-Butylphenoxy) -6-chloro-4-methoxy-5- (trimethylsilyl) pyridazine (Step G-1)
498 mg (1.70 mmol) of 3- (2-tert-butylphenoxy) -6-chloro-4-methoxypyridazine obtained in Example 31 (1) was dissolved in dry tetrahydrofuran (15 mL), and the solution was brought to -78 ° C. After cooling, 1.10 mL (1.87 mmol) of n-butyllithium hexane solution (1.70 M) was added and stirred for 20 minutes. To this was added 0.370 mL (2.91 mmol) of trimethylsilyl chloride, and the mixture was stirred at the same temperature for 10 minutes. The reaction mixture was poured into saturated aqueous ammonium chloride and extracted with ether. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography to obtain 596 mg (1.63 mmol, 3- (2-tert-butylphenoxy) -6-chloro-4-methoxy-5- (trimethylsilyl) pyridazine. Yield 95.9%).
(2) 3- (2-tert-Butylphenoxy) -6-chloro-5- (trimethylsilyl) -4-pyridazinol (Compound No. 2405, Step G-2)
Sodium iodide (0.17 g, 1.1 mmol), trimethylsilyl chloride (0.14 mL, 1.1 mmol) and acetonitrile (3.5 mL) were mixed. ) -6-chloro-4-methoxy-5- (trimethylsilyl) pyridazine (340 mg, 0.932 mmol) was added, and the mixture was stirred at room temperature for 1 hour and 35 minutes. The reaction mixture was poured into a saturated aqueous sodium sulfite solution and ice-cold dilute hydrochloric acid was added. This mixture was extracted with ethyl acetate, and the organic layers were combined and washed with saturated brine. The solvent was distilled off, the residue was purified by silica gel column chromatography, and 275 mg (0.783) of 3- (2-tert-butylphenoxy) -6-chloro-5- (trimethylsilyl) -4-pyridazinol (Compound No. 2405) was obtained. Mmol, yield 84.0%).
¹ H-NMR (90 MHz, CDCl ₃ ) δ ppm: 10.12 (1H, br.s), 7.39-6.75 (4H, m), 1.24 (9H, s), 0.31 (9H, s).
Melting point (° C): 160-163.

(Example 34)
6-Bromo-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 2411)
(1) 5-Chloro-6- (2-methylphenoxy) -3-pyridazinol (Process P-1)
A mixture of 578 mg (2.27 mmol) of 4,6-dichloro-3- (2-methylphenoxy) pyridazine obtained in Example 1 (2), acetic acid (10 mL) and 0.45 g (4.6 mmol) of potassium acetate was heated for 5 hours. Refluxed. The reaction mixture was allowed to cool, 50 mL of water was added, and the mixture was extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled off to obtain 461 mg (1.95 mmol, yield 85.9%) of 5-chloro-6- (2-methylphenoxy) -3-pyridazinol.
(2) 4,6-Dibromo-3- (2-methylphenoxy) pyridazine (Step P-2)
151 mg (0.637 mmol) of 5-chloro-6- (2-methylphenoxy) -3-pyridazinol obtained by (1), chloroform (3 mL) and 913 mg (3.18 mmol) of phosphorus oxybromide were mixed. Heated to reflux for 5 hours. The reaction mixture was allowed to cool, water and dichloromethane were added, and the mixture was stirred at room temperature for 1 hr. This mixture was extracted with dichloromethane. The organic layers were combined and washed sequentially with water and saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography to obtain 176 mg (0.512 mmol, yield 80.4%) of 4,6-dibromo-3- (2-methylphenoxy) pyridazine.
(3) 6-bromo-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 2411, Step P-3)
114 mg (0.331 mmol) of 4,6-dibromo-3- (2-methylphenoxy) pyridazine obtained in (2) was dissolved in dimethyl sulfoxide (3 mL), and 0.8 mol (1.6 mol) of a 2 mol / L aqueous sodium hydroxide solution was added to this solution. Mmol) and stirred at room temperature for 3 hours. Water was added to the reaction mixture and washed with ethyl acetate. The aqueous layer was acidified with 4 mol / L hydrochloric acid and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was washed with an ethyl acetate-ether mixed solvent, and 56.0 mg (0.199 mmol, yield 60.1) of 6-bromo-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 2411) was obtained. %)Obtained.
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.35-7.05 (4H, m), 6.82 (1H, br.s), 2.10 (3H, s).
Melting point (° C): 197-198.

(Example 35)
6-Cyclopropyl-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 2423)
(1) 6-cyclopropyl-4-methoxy-3- (2-methylphenoxy) pyridazine (Step L-1)
To 2.94 mL (1.47 mmol) of 9-borabicyclo [3.3.1] nonane in tetrahydrofuran (0.5 mol / l) was added 87.5 mg (0.735 mmol) of propargyl bromide, and the mixture was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature, 0.74 mL (2.2 mmol) of 3 mol / L sodium hydroxide aqueous solution was added, and the mixture was stirred at room temperature for 70 minutes. Here, 168 mg (0.669 mmol) of 6-chloro-4-methoxy-3- (2-methylphenoxy) pyridazine obtained in Example 2 (1) and 38.7 mg (0.00334 mmol) of tetrakis (triphenylphosphine) palladium were sequentially added. In addition, the mixture was heated to reflux overnight. The reaction mixture was allowed to cool, water was added, and the mixture was extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography to obtain 121 mg (0.473 mmol, yield 70.1%) of 6-cyclopropyl-4-methoxy-3- (2-methylphenoxy) pyridazine.
(2) 6-cyclopropyl-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 2423, Step L-2)
2-hydroxypyridine (45.6 mg, 0.479 mmol) was dissolved in dimethyl sulfoxide (2 mL), potassium tert-butoxide (53.8 mg, 0.480 mmol) was added to the solution at room temperature, and the mixture was stirred at room temperature for 10 minutes. To this was added a solution of 112 mg (0.438 mmol) of 6-cyclopropyl-4-methoxy-3- (2-methylphenoxy) pyridazine obtained in (1) in dimethyl sulfoxide (1 mL), and the mixture was added at 60 ° C. for 5 hours. Stir at 15 ° C. for 15 hours. Further, 45.6 mg (0.479 mmol) of 2-hydroxypyridine and 53.8 mg (0.480 mmol) of potassium tert-butoxide were added, followed by stirring at 80 ° C. for 4 hours and 30 minutes. The reaction mixture was allowed to cool, water was added, and the mixture was washed with ethyl acetate. The aqueous layer was acidified with 4 mol / L hydrochloric acid and extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled off. The obtained residue was purified by preparative thin layer chromatography (Merck, 1.05744, developed with ethyl acetate) to give 6-cyclopropyl-3- (2-methylphenoxy) -4-pyridazinol (Compound No. 2423) 28.6 mg (0.118 mmol, yield 26.9%) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.30-7.01 (4H, m), 6.19 (1H, s), 1.98-1.82 (1H, m), 1.23-1.12 (2H, m), 0.99-0.88 (2H, m).
Melting point (° C): 214-215.

(Example 36)
3- (2-Methylphenoxy) -6-vinyl-4-pyridazinol (Compound No. 2436)
(1) 4-Methoxy-3- (2-methylphenoxy) -6-vinylpyridazine (Step L-1)
123 mg (0.490 mmol) of 6-chloro-4-methoxy-3- (2-methylphenoxy) pyridazine obtained in Example 2 (1) was dissolved in toluene (2 mL), and this solution was dissolved in tributyl (vinyl) at room temperature. 246 mg (0.776 mmol) of tin and then 119 mg (0.103 mmol) of tetrakis (triphenylphosphine) palladium were sequentially added and heated to reflux for 3 hours. The reaction mixture was allowed to cool, ethyl acetate (5 mL), water (3 mL) and sodium fluoride were added and stirred for 30 minutes and left at room temperature overnight. The mixture was filtered through celite, ethyl acetate was added to the filtrate, the organic layer was separated, and washed with saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (eluting with hexane: ethyl acetate = 1: 2), and 105 mg (0.434 mmol, 4-methoxy-3- (2-methylphenoxy) -6-vinylpyridazine was collected. Rate 88.6%).
(2) 3- (2-Methylphenoxy) -6-vinyl-4-pyridazinol (Compound No. 2436, Step L-2)
2-hydroxypyridine (33.7 mg, 0.354 mmol) was dissolved in dimethyl sulfoxide (1 mL), and potassium tert-butoxide (39.7 mg, 0.354 mmol) was added to the solution at room temperature, followed by stirring at room temperature for 10 minutes. To this was added a solution of 4-methoxy-3- (2-methylphenoxy) -6-vinylpyridazine obtained in (1) in 85.8 mg (0.354 mmol) in dimethyl sulfoxide (1 mL), and at room temperature overnight at 50 ° C. For 4 hours 30 minutes. The reaction mixture was allowed to cool, water was added, and the mixture was washed with ethyl acetate. The aqueous layer was acidified with 4 mol / L hydrochloric acid and extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate, and then the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (developed with hexane: ethyl acetate = 1: 4) to give 51.7 mg of 3- (2-methylphenoxy) -6-vinyl-4-pyridazinol (Compound No. 2436). (0.227 mmol, yield 64.1%).
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.35-7.03 (4H, m), 6.56-6.43 (2H, m), 6.16 (1H, d, J = 17.9 Hz), 6.16 (1H, d, J = 11.4Hz), 2.11 (3H, s).
Melting point (° C): 195-197.

(Example 37)
3- (2-Methylphenoxy) -6- (1-propenyl) -4-pyridazinol (Compound No. 2442)
(1) 6-allyl-4-methoxy-3- (2-methylphenoxy) pyridazine (Step L-1)
200 mg (0.797 mmol) of 6-chloro-4-methoxy-3- (2-methylphenoxy) pyridazine obtained in Example 2 (1) was dissolved in toluene (4 mL), and this solution was dissolved in allyl (tributyl) at room temperature. Tin (305 mg, 0.921 mmol) and then tetrakis (triphenylphosphine) palladium (96.8 mg, 0.0838 mmol) were sequentially added, and the mixture was heated to reflux for 3 hours and 20 minutes. The reaction mixture was allowed to stand overnight at room temperature, and then ethyl acetate, water and sodium fluoride were added and stirred for 2 hours. The mixture was filtered through celite, ethyl acetate was added to the filtrate, the organic layer was separated, and washed successively with water and saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate, gradient), and 62.1 mg (0.243 mmol, yield 30.5%) of 6-allyl-4-methoxy-3- (2-methylphenoxy) pyridazine. )Obtained.
(2) 3- (2-Methylphenoxy) -6- (1-propenyl) -4-pyridazinol (Compound No. 2442, Step L-2)
2-hydroxypyridine (25.3 mg, 0.267 mmol) was dissolved in dimethyl sulfoxide (2 mL), potassium tert-butoxide (29.9 mg, 0.267 mmol) was added to the solution at room temperature, and the mixture was stirred at room temperature for 10 minutes. To this was added 62.1 mg (0.243 mmol) of dimethyl sulfoxide (3 mL) of 6-allyl-4-methoxy-3- (2-methylphenoxy) pyridazine obtained in (1), and the mixture was added at 100 ° C. for 8 hours and 130 ° C. Stir at 5 ° C. for 5 hours 30 minutes. Further, 25.3 mg (0.267 mmol) of 2-hydroxypyridine and 29.9 mg (0.267 mmol) of potassium tert-butoxide were added, followed by stirring at 130 ° C. for 5 hours. The reaction mixture was allowed to cool, water was added, and the mixture was washed with ethyl acetate. The aqueous layer was acidified with 4 mol / L hydrochloric acid and extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate, and then the solvent was distilled off. The obtained residue was purified by preparative thin layer chromatography (Merck, 1.05744, 3 plates used, developed with ethyl acetate), and 3- (2-methylphenoxy) -6- (1-propenyl) -4 -21.3 mg (0.0880 mmol, yield 36.2%) of pyridazinol (Compound No. 2442) was obtained.
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.32–7.03 (4H, m), 6.75-6.60 (1H, m), 6.44 (1H, s), 6.22-6.10 (1H, m), 2.10 ( 3H, s), 1.86 (3H, br.d, J = 6.6 Hz).
Melting point (° C): 208-210.

(Example 38)
6- (2,6-Dimethylphenoxy) -5-hydroxy-3-pyridazinecarbonitrile (Compound No. 2453)
(1) 6-chloro-3- (2,6-dimethylphenoxy) -4-methoxypyridazine 1-oxide (step K-1)
6-chloro-3- (2,6-dimethylphenoxy) -4-methoxypyridazine 3.42 g (12.9 mmol), dichloromethane (110 mL) and 80% m-chloroperbenzoic acid 3.34 g (15.4 mmol) were mixed together. The mixture was stirred at room temperature for 16 days. The reaction mixture was poured into ice-cold saturated aqueous sodium sulfite and extracted with dichloromethane. The organic layers were combined, washed successively with saturated aqueous sodium hydrogen carbonate solution, water and brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was purified by silica gel column chromatography, and 2.06 g (7.33 mmol, yield 56.8%) of 6-chloro-3- (2,6-dimethylphenoxy) -4-methoxypyridazine 1-oxide. )Obtained.
(2) 3- (2,6-Dimethylphenoxy) -4-methoxypyridazine 1-oxide (Step K-2)
6-chloro-3- (2,6-dimethylphenoxy) -4-methoxypyridazine 1-oxide (6.00 g, 21.4 mmol) obtained in (1), methanol (200 mL), triethylamine 3.0 mL, acetone (5 mL) and 0.5 g of 5% palladium on carbon was mixed, and this mixture was shaken using a Parr reducing apparatus at a hydrogen pressure of 3.5 atm for 2 hours. The reaction mixture was filtered and the filtrate was concentrated. Water was added to the residue and extracted with chloroform. The organic layers were combined, washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was crystallized with an ether-dichloromethane mixed solvent to obtain 4.32 g (17.6 mmol, yield 82.2%) of 3- (2,6-dimethylphenoxy) -4-methoxypyridazine 1-oxide. .
(3) 6- (2,6-Dimethylphenoxy) -5-methoxy-3-pyridazinecarbonitrile (Step M-1)
3- (2,6-Dimethylphenoxy) -4-methoxypyridazine 1-oxide 0.720 g (2.92 mmol) obtained in (2) was dissolved in dry N, N-dimethylformamide (15 mL) and trimethylsilyl cyanide was dissolved in this solution. 1.10 mL (8.25 mmol) of nido and 2.00 mL (14.4 mmol) of triethylamine were added and stirred at 90 ° C. for 1 hour 30 minutes. The reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was purified by silica gel column chromatography, and 0.675 g (2.65 mmol, yield 90.8%) of 6- (2,6-dimethylphenoxy) -5-methoxy-3-pyridazinecarbonitrile was obtained. Obtained.
(4) 6- (2,6-Dimethylphenoxy) -5-hydroxy-3-pyridazinecarbonitrile (Compound No. 2453, Step M-2)
6- (2,6-Dimethylphenoxy) -5-methoxy-3-pyridazinecarbonitrile 0.500 g (1.96 mmol) obtained in (3) was dissolved in acetonitrile (5 mL), and trimethylsilyl chloride 0.300 mL ( 2.36 mmol) and 0.350 g (2.33 mmol) of sodium iodide were added and stirred at room temperature. 5 mL of acetonitrile was added and stirred for 1 hour, and then 3 mL of 1,4-dioxane was added and stirred overnight. The reaction mixture was poured into an aqueous sodium sulfite solution and acidified with 1 mol / L hydrochloric acid. Extracted with dichloromethane, washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was purified by silica gel column chromatography, and 0.121 g (0.502 mmol, 6- (2,6-dimethylphenoxy) -5-hydroxy-3-pyridazinecarbonitrile (Compound No. 2453) was collected. Rate 25.6%).
¹ H-NMR (90 MHz, CDCl ₃ ) δ ppm: 11.3 (1H, br.s), 7.09-6.99 (4H, m), 1.90 (6H, s).
Physical properties: amorphous.

(Example 39)
1- [5-Hydroxy-6- (2-methylphenoxy) -3-pyridazinyl] ethanone (Compound No. 2455)
(1) 6- (1-Ethoxyvinyl) -4-methoxy-3- (2-methylphenoxy) pyridazine (Step L-1)
321 mg (1.28 mmol) of 6-chloro-4-methoxy-3- (2-methylphenoxy) pyridazine obtained in Example 2 (1) was dissolved in toluene (6.5 mL), and this solution was dissolved in (1- Ethoxyvinyl) (tributyl) tin (534 mg, 1.48 mmol) and tetrakis (triphenylphosphine) palladium (155.3 mg, 0.134 mmol) were sequentially added, and the mixture was heated to reflux for 3 hours and 20 minutes. The reaction mixture was allowed to stand overnight at room temperature, and then ethyl acetate, water and sodium fluoride were added and stirred for 2 hours. The mixture was filtered through celite, ethyl acetate was added to the filtrate, the organic layer was separated, and washed successively with water and saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate, gradient), and 51.8 mg (0.181 mmol) of 6- (1-ethoxyvinyl) -4-methoxy-3- (2-methylphenoxy) pyridazine was obtained. Yield 14.1%).
(2) 1- [5-hydroxy-6- (2-methylphenoxy) -3-pyridazinyl] ethanone (Compound No. 2455, Step L-2)
2-Hydroxypyridine (18.4 mg, 0.194 mmol) was dissolved in dimethyl sulfoxide (2 mL), potassium tert-butoxide (21.7 mg, 0.194 mmol) was added to the solution at room temperature, and the mixture was stirred at room temperature for 10 minutes. To this was added a solution of 60.4- (1-ethoxyvinyl) -4-methoxy-3- (2-methylphenoxy) pyridazine obtained in (1) in 50.4 mg (0.176 mmol) in dimethyl sulfoxide (3 mL), and 100 ° C. And stirred at 130 ° C. for 5 hours and 30 minutes. Further, 18.4 mg (0.194 mmol) of 2-hydroxypyridine and 21.7 mg (0.194 mmol) of potassium tert-butoxide were added, followed by stirring at 130 ° C. for 2 hours. The reaction mixture was allowed to cool, water was added, and the mixture was washed with ethyl acetate. The aqueous layer was acidified with 4 mol / L hydrochloric acid and extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate, and then the solvent was distilled off. The obtained residue was purified by preparative thin layer chromatography (Merck, 1.05744, 3 plates used, developed with ethyl acetate), and 1- [5-hydroxy-6- (2-methylphenoxy) -3- 28.5 mg (0.117 mmol, 66.5% yield) of pyridazinyl] ethanone (Compound No. 2455) was obtained.
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.48-7.05 (5H, m), 2.58 (3H, s), 2.10 (3H, s).
Melting point (° C): 182-185.

(Example 40)
3- (2-Methylphenoxy) -6-phenyl-4-pyridazinol (Compound No. 2464)
(1) 4-Methoxy-3- (2-methylphenoxy) -6-phenylpyridazine (Step L-1)
210 mg (0.837 mmol) of 6-chloro-4-methoxy-3- (2-methylphenoxy) pyridazine obtained according to Example 2 (1), toluene (4 mL) and water (0.5 mL) were mixed. At room temperature, 161 mg (1.32 mmol) of phenylboronic acid, 365 mg (2.64 mmol) of potassium carbonate and 102 mg (0.0879 mmol) of tetrakis (triphenylphosphine) palladium were sequentially added and heated under reflux for 2 hours and 50 minutes. The reaction mixture was allowed to stand overnight at room temperature, and then the mixture was filtered through celite. Ethyl acetate and water were added to the filtrate. The organic layer was separated and washed with saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (eluting with hexane: ethyl acetate = 3: 1), and 146 mg (0.500 mmol, 4-methoxy-3- (2-methylphenoxy) -6-phenylpyridazine was collected. Rate 59.7%).
(2) 3- (2-Methylphenoxy) -6-phenyl-4-pyridazinol (Compound No. 2464, Step L-2)
91.9 mg (0.966 mmol) of 2-hydroxypyridine was dissolved in dimethyl sulfoxide (1.5 mL), and 95.4 mg (0.850 mmol) of potassium tert-butoxide was added to this solution at room temperature, followed by stirring at room temperature for 10 minutes. To this, a solution of 4-methoxy-3- (2-methylphenoxy) -6-phenylpyridazine obtained in (1) in 82.8 mg (0.283 mmol) in dimethyl sulfoxide (1 mL) was added and stirred at 60 ° C. for 3 hours. . The reaction mixture was allowed to cool, water was added, and the mixture was washed with ethyl acetate. The aqueous layer was acidified with 4 mol / L hydrochloric acid and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (Merck, 1.05744, 3 plates used, developed with ethyl acetate), and 3- (2-methylphenoxy) -6-phenyl 70.8 mg (0.255 mmol, 90.1% yield) of 4-pyridazinol (Compound No. 2464) was obtained.
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.78-7.66 (2H, m), 7.58-7.48 (3H, m), 7.35-7.08 (4H, m), 6.69 (1H, s), 2.15 ( 3H, s).
Melting point (° C): 236-237.

(Example 41)
3,6-bis (2-fluorophenoxy) -4-pyridazinol (Compound No. 2485)
(1) 3,6-bis (2-fluorophenoxy) pyridazine
2.69 g (24.0 mmol) of 2-fluorophenol was dissolved in dimethyl sulfoxide (20 mL), and 2.69 g (24.0 mmol) of potassium tert-butoxide was added to this solution at room temperature. To this, 1.49 g (10.0 mmol) of 2,6-dichloropyridazine was added and stirred at 100 ° C. for 3 hours. The reaction mixture was allowed to cool, poured into ice-cold water, and extracted with ethyl acetate. The organic layers were combined, washed successively with 1 mol / L sodium hydroxide aqueous solution, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was washed with heated hexane and then heated isopropyl ether to obtain 1.71 g (5.70 mmol, yield 57.0%) of 3,6-bis (2-fluorophenoxy) pyridazine. It was.
(2) 3,6-bis (2-fluorophenoxy) pyridazine 1-oxide (step C-1)
3.14 g (13.8 mmol) of 3,6-bis (2-fluorophenoxy) pyridazine obtained by (1) was dissolved in dry dichloromethane (40 mL), and 3.19 g (14.8 mmol) of 80% m-chloroperbenzoic acid was dissolved in this solution. ) And stirred at room temperature for 7 days. The reaction mixture was poured into ice-cold 1 mol / L sodium hydroxide aqueous solution and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (eluting with hexane: ethyl acetate = 3: 1) to obtain 2.24 g of 3,6-bis (2-fluorophenoxy) pyridazine 1-oxide. (7.09 mmol, yield 51.4%).
(3) 4-Chloro-3,6-bis (2-fluorophenoxy) pyridazine (Step C-2)
2,6-bis (2-fluorophenoxy) pyridazine 1-oxide (2.20 g, 6.96 mmol) obtained in (2) was mixed with 50 mL of phosphorus oxychloride, and the mixture was stirred at 90 ° C. for 1 hour. The reaction mixture was allowed to cool, poured into ice-cold water, and extracted with ethyl acetate. The organic layers were combined, washed successively with 1 mol / L sodium hydroxide aqueous solution, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1) to obtain 1.95 g of 4-chloro-3,6-bis (2-fluorophenoxy) pyridazine ( 5.82 mmol, yield 83.6%).
(4) 3,6-bis (2-fluorophenoxy) -4-methoxypyridazine (Step C-3)
1.44 g (4.30 mmol) of 4-chloro-3,6-bis (2-fluorophenoxy) pyridazine obtained by (3) was dissolved in methanol (20 mL), and 0.206 g (4.72 mmol) of 55% sodium hydride was dissolved in this solution. ) And stirred at 60 ° C. for 1 hour. The reaction mixture was allowed to cool, poured into ice-cold water, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (eluted with hexane: ethyl acetate = 10: 1) to give 3,6-bis (2-fluorophenoxy) -4-methoxypyridazine as 1.03. g (3.12 mmol, yield 72.6%) was obtained.
(5) 3,6-bis (2-fluorophenoxy) -4-pyridazinol (Compound No. 2485, Step C-4)
3,6-bis (2-fluorophenoxy) -4-methoxypyridazine 450 mg (1.36 mmol), 96% sodium hydroxide 77 mg (1.85 mmol), dimethyl sulfoxide (5 mL) and water (1 mL) obtained by (4) And the mixture was stirred at 90 ° C. for 2 hours. The reaction mixture was poured into ice-cold water and acidified with hydrochloric acid. This was extracted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 0.380 g (1.20 mmol, yield 88.2%) of 3,6-bis (2-fluorophenoxy) -4-pyridazinol (Compound No. 2485).
¹ H-NMR (60 MHz, DMSO-d ₆ ) δ ppm: 7.60-7.08 (8H, m), 6.34 (1H, br.s).
Melting point (° C): 228.

(Example 42)
(2,4-Dichlorophenyl) (5-{[5-hydroxy-6- (2-methylphenoxy) -3-pyridazinyl] oxy} -1,3-dimethyl-1H-pyrazol-4-yl) methanone (compound number 2506)
(1) (5-{[5-Chloro-6- (2-methylphenoxy) -3-pyridazinyl] oxy} -1,3-dimethyl-1H-pyrazol-4-yl) (2,4-dichlorophenyl) methanone
109 mg (0.382 mmol) of (2,4-dichlorophenyl) (5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl) methanone, 4,6-dichloro-3 obtained according to Example 1 (2) 1.62 g (6.35 mmol) of-(2-methylphenoxy) pyridazine and 107 mg (0.775 mmol) of potassium carbonate were mixed and the mixture was stirred at 130 ° C. for 14 hours. The reaction mixture was cooled to room temperature and purified by silica gel column chromatography (hexane: ethyl acetate, gradient) to give (5-{[5-chloro-6- (2-methylphenoxy) -3-pyridazinyl] oxy} -1 Thus, 155 mg (0.308 mmol, yield 80.6%) of 3,3-dimethyl-1H-pyrazol-4-yl) (2,4-dichlorophenyl) methanone was obtained.
(2) (2,4-Dichlorophenyl) (5-{[5-hydroxy-6- (2-methylphenoxy) -3-pyridazinyl] oxy} -1,3-dimethyl-1H-pyrazol-4-yl) methanone (Compound No. 2506, Step A-3)
(5-{[5-Chloro-6- (2-methylphenoxy) -3-pyridazinyl] oxy} -1,3-dimethyl-1H-pyrazol-4-yl) (2,4) obtained by (1) -Dichlorophenyl) methanone 12.3 mg (0.0244 mmol), dimethyl sulfoxide 0.2 mL and 10% (W / V) aqueous sodium hydroxide solution 0.012 mL were mixed and stirred overnight at room temperature. The reaction mixture was poured into ice-cold water, acidified with hydrochloric acid and extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by preparative thin layer chromatography (Merck, 1.05744, developed with dichloromethane: methanol = 10: 1) and (2,4-dichlorophenyl) (5-{[5 -Hydroxy-6- (2-methylphenoxy) -3-pyridazinyl] oxy} -1,3-dimethyl-1H-pyrazol-4-yl) methanone (Compound No. 2506) 3.2 mg (0.00784 mmol, 32% yield) ) And 4-[{[5-chloro-6- (2-methylphenoxy) -3-pyridazinyl] oxy} (2,4-dichlorophenyl) methylene] -2,5-dimethyl-2,4-dihydro- 10.5 mg (0.0208 mmol, yield 85.4%) of 3H-pyrazol-3-one was obtained.
Compound No. 2506:
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.36-7.04 (7H, m), 6.20 (1H, br.s), 3.64 (3H, s), 2.31 (3H, s), 2.20 (3H, s) .
Physical properties: amorphous.

In addition, the following compounds were produced by or according to the methods of Examples 1-42 or Examples 622-646 described below.

(Example 43)
3-phenoxy-4-pyridazinol (Compound No. 1)
¹ H-NMR (90 MHz, DMSO-d ₆ ) δppm: 12.66 (1H, br.s), 8.21 (1H, d, J = 6.6 Hz), 7.09-7.54 (5H, m), 6.38 (1H, d, J = 6.6Hz).
Melting point (° C): 193.5.

(Example 44)
6-chloro-3- {2- [1- (methoxymethyl) cyclopropyl] phenoxy} -4-pyridazinol (Compound No. 163)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.47-7.35 (1H, m), 7.32-7.02 (3H, m), 6.71 (1H, s), 3.47 (2H, s), 3.21 (3H, s ), 0.80-0.70 (4H, m).
Melting point (° C): 187-190.

(Example 45)
3- (2-Isopropylphenoxy) -4-pyridazinol (Compound No. 6)
¹ H-NMR (90 MHz, DMSO-d ₆ ) δppm: 12.65 (1H, br.s), 8.29 (2H, d, J = 6.6 Hz), 7.49-6.98 (4H, m), 6.36 (1H, d, J = 6.6Hz), 3.20-2.89 (1H, m, J = 6.6Hz), 1.16 (6H, d, J = 6.6Hz).
Melting point (° C): 181.5-182.

(Example 46)
6-Chloro-3- [2- (1-methoxycyclopropyl) phenoxy] -4-pyridazinol (Compound No. 202)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.50-7.10 (4H, m), 6.67 (1H, s), 3.03 (3H, s), 1.00-0.85 (4H, m).
Melting point (° C): 157-165.

(Example 47)
2- {2-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] phenyl} cyclopropanecarbonitrile (Compound No. 226)
Trans form:
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.40-7.10 (4H, m), 6.75 (1H, s), 2.65-2.50 (1H, m), 1.65-1.45 (3H, m).
Melting point (° C): 203-207.
Cis body:
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.40-7.15 (4H, m), 6.64 (1H, s), 2.59 (1H, q, J = 8.4 Hz), 2.05-1.90 (1H, m), 1.67-1.40 (2H, m).
Melting point (° C): 225-227.

(Example 48)
6-Chloro-3-phenoxy-4-pyridazinol (Compound No. 123)
¹ H-NMR (60 MHz, DMF-d ₇ ) δ ppm: 7.60-7.00 (5H, m), 6.87 (1H, s).
Melting point (° C): 222-224.

(Example 49)
6-Chloro-3- (2-fluorophenoxy) -4-pyridazinol (Compound No. 124)
¹ H-NMR (90 MHz, CD ₃ OD) δ ppm: 7.50-7.05 (4H, m), 6.70 (1H, s).
Melting point (° C): 210-212.

(Example 50)
6-Chloro-3- (2-chlorophenoxy) -4-pyridazinol (Compound No. 125)
¹ H-NMR (60 MHz, DMF-d ₇ ) δ ppm: 7.70-7.10 (4H, m), 6.95 (1H, s).
Melting point (° C): 208-212.

(Example 51)
3- (2-Bromophenoxy) -6-chloro-4-pyridazinol (Compound No. 126)
¹ H-NMR (90 MHz, CD ₃ OD) δ ppm: 7.68 (1H, dd, J = 7.5, 1.8 Hz), 7.53-7.10 (3H, m), 6.73 (1H, s).
Melting point (° C): 201-203.

(Example 52)
6-Chloro-3- (2-iodophenoxy) -4-pyridazinol (Compound No. 127)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.89 (1H, dd, J = 7.7, 1.5 Hz), 7.45 (1H, td, J = 7.7, 1.5 Hz), 7.22 (1H, dd, J = 7.7 , 1.5Hz), 7.04 (1H, td, J = 7.7, 1.5Hz), 6.74 (1H, s).
Melting point (° C): 216-217.

(Example 53)
6-Chloro-3- [2- (2-ethoxycyclopropyl) phenoxy] -4-pyridazinol (Compound No. 249)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.26-7.05 (4H, m), 6.68 (1H, s), 3.46 (1H, q, J = 5.2 Hz), 3.30-3.15 (2H, m), 2.17-1.96 (1H, m), 1.10 (2H, dd, J = 5.2Hz, 8.5Hz), 0.93 (3H, t, J = 7.0Hz).
Melting point (° C): 145-152.

(Example 54)
6-Chloro-3- [2- (2,2-difluorocyclopropyl) phenoxy] -4-pyridazinol (Compound No. 264)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.40-7.15 (4H, m), 6.72 (1H, s), 2.85-2.65 (1H, m), 1.90-1.65 (2H, s).
Melting point (° C): 215-216.

(Example 55)
6-Chloro-3- (2-ethylphenoxy) -4-pyridazinol (Compound No. 130)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.35-7.15 (3H, m), 7.10-7.02 (1H, m), 6.70 (1H, s), 2.56 (2H, q, J = 7.7 Hz), 1.17 (3H, t, J = 7.7Hz).
Melting point (° C): 217-218.

(Example 56)
6-Chloro-3- (2-propylphenoxy) -4-pyridazinol (Compound No. 131)
¹ H-NMR (60 MHz, DMF-d ₇ ) δppm: 7.45-7.05 (4H, m), 6.90 (1H, s), 3.00-2.35 (2H, m), 1.95-1.26 (2H, m), 1.05- 0.68 (3H, m).
Melting point (° C): 170-172.

(Example 57)
6-Chloro-3- (2-isopropylphenoxy) -4-pyridazinol (Compound No. 132)
¹ H-NMR (60MHz, DMF-d ₇ ) δppm: 7.60-7.00 (4H, m), 6.92 (1H, s), 3.11 (1H, septet, J = 7.0Hz), 1.18 (6H, d, J = 7.0Hz).
Melting point (° C): 183.

(Example 58)
3- (2-Butylphenoxy) -6-chloro-4-pyridazinol (Compound No. 133)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 11.8 (1H, br.s), 7.30-6.70 (4H, m), 6.53 (1H, s), 2.60-2.00 (2H, m), 1.80-0.60 ( 7H, m).
Melting point (° C): 149.5-150.

(Example 59)
6-Chloro-3- (2-isobutylphenoxy) -4-pyridazinol (Compound No. 134)
¹ H-NMR (60MHz, CDCl ₃ ) δppm: 12.90 (1H, br.s), 7.40-6.85 (4H, m), 6.50 (1H, s), 2.25 (2H, d, J = 10.0Hz), 2.20 -1.45 (1H, m, J = 10.0Hz), 0.75 (6H, d, J = 10.0Hz).
Melting point (° C): 151.5-152.5.

(Example 60)
3- (2-sec-Butylphenoxy) -6-chloro-4-pyridazinol (Compound No. 135)
¹ H-NMR (60MHz, CDCl ₃ + DMF-d ₇ ) δppm: 7.35-6.80 (4H, m), 6.60 (1H, s), 3.05-2.50 (1H, m), 1.80-1.25 (2H, m) , 1.13 (3H, d, J = 6.2Hz), 0.95-0.50 (3H, m).
Melting point (° C): 158-159.

(Example 61)
3- (2-tert-Butylphenoxy) -6-chloro-4-pyridazinol (Compound No. 136)
¹ H-NMR (60 MHz, DMF-d ₇ ) δ ppm: 7.55-6.85 (4H, m), 6.91 (1H, s), 5.32 (1H, br.s), 1.35 (9H, s).
Melting point (° C): 215-216.

(Example 62)
6-Chloro-3- (2-pentylphenoxy) -4-pyridazinol (Compound No. 137)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 11.70 (1H, br.s), 7.40-6.80 (4H, m), 6.50 (1H, s), 2.60-2.20 (2H, m), 1.80-0.60 ( 9H, m).
Melting point (° C): 151.5-152.5.

(Example 63)
6-Chloro-3- (2-hexylphenoxy) -4-pyridazinol (Compound No. 138)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 7.40-6.70 (4H, m), 6.53 (1H, s), 2.70-2.20 (2H, m), 2.00-0.60 (11H, m).
Melting point (° C): 118-118.5.

(Example 64)
6-Chloro-3- [2- (2,2-dichlorocyclopropyl) phenoxy] -4-pyridazinol (Compound No. 265)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.55-7.15 (4H, m), 6.69 (1H, s), 2.90 (1H, dd, J = 11.0, 10.8 Hz), 2.05-1.85 (2H, m ).
Melting point (° C): 158-163.

(Example 65)
6-Chloro-3- [2- (2,2-dibromocyclopropyl) phenoxy] -4-pyridazinol (Compound No. 266)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.41-7.36 (1H, m), 7.29-7.13 (3H, m), 6.71 (1H, s), 2.97-2.87 (1H, dd, J = 11.0, 8.4Hz), 2.21-2.01 (2H, m).
Melting point (° C): 208-210 (decomposition).

Example 66
6-Chloro-3- [2- (1-methylcyclopropyl) phenoxy] -4-pyridazinol (Compound No. 144)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.40-7.35 (1H, m), 7.22-7.17 (2H, m), 6.99-6.94 (1H, m), 6.59 (1H, s), 1.25 (3H, s), 0.85-0.60 (2H, m), 0.60-0.45 (2H, m).
Melting point (° C): 196-198.

(Example 67)
6-Chloro-3- [2- (1-ethylcyclopropyl) phenoxy] -4-pyridazinol (Compound No. 145)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.35-7.10 (3H, m), 6.98 (1H, br.d, J = 7.3 Hz), 6.59 (1H, s), 1.50 (2H, q, J = 7.0Hz), 1.26 (3H, t, J = 7.0Hz), 0.67-0.50 (4H, m).
Melting point (° C): 162-165.

Example 68
6-Chloro-3- {2- [1- (cyclopropyl) cyclopropyl] phenoxy} -4-pyridazinol (Compound No. 151)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.35-7.29 (1H, m), 7.26-7.10 (2H m), 7.00-6.92 (1H, m), 6.58 (1H, s), 1.30-1.15 (1H , m), 0.60-0.40 (4H, m), 0.27-0.15 (2H, m), 0.07-0.00 (2H, m).
Melting point (° C): 180-182.

(Example 69)
1- {2-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] phenyl} cyclopropanecarbonitrile (Compound No. 173)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.55-7.15 (5H, m), 1.65-1.20 (4H, m).
Melting point (° C): 63-64.

(Example 70)
6-Chloro-3- [2- (1-phenylcyclopropyl) phenoxy] -4-pyridazinol (Compound No. 184)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.65-7.55 (1H, m), 7.28-7.20 (2H, m), 7.17-6.95 (6H, m), 6.41 (1H, s), 1.19 (4H, s).
Melting point (° C): 172-173.

(Example 71)
6-Chloro-3- (2-isopropenylphenoxy) -4-pyridazinol (Compound No. 304)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.36-7.10 (4H, m), 6.66 (1H, s), 5.06 (1H, br.s), 5.02 (1H, br.s), 2.01 (3H , d, J = 1.5 Hz).
Melting point (° C): 187-188.

(Example 72)
6-Chloro-3- [2- (2-methylcyclopropyl) phenoxy] -4-pyridazinol (Compound No. 217)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.32-6.97 (4H, m), 6.82 (1H, br.s), 1.89-1.78 (0.8H, m), 1.52-1.43 (0.2H, m ), 1.05-0.60 (6H, m).
Melting point (° C): 192-208.

(Example 73)
6-Chloro-3- [2- (2-ethoxycyclopropyl) phenoxy] -4-pyridazinol (Compound No. 249)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.30-7.05 (4H, m), 6.68 (1H, s), 3.51-3.15 (3H, m), 2.07-1.95 (1H, m), 1.13-1.06 (2H, m), 0.93 (3H, t, J = 7.1Hz).
Melting point (° C): 145-152.

(Example 74)
(2E) -3- {2-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] phenyl} acrylonitrile (Compound No. 306)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.80-7.40 (3H, m), 7.35-7.15 (2H, m), 6.72 (1H, s), 6.30 (1H, d, J = 6.9 Hz).
Melting point (° C): 190-192.

(Example 75)
6-Chloro-3- [2- (2,2-dimethylcyclopropyl) phenoxy] -4-pyridazinol (Compound No. 267)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.30-7.10 (4H, m), 1.57 (1H, dd, J = 8.4, 6.2 Hz), 0.91-0.85 (1H, m), 0.85 (3H, s), 0.72-0.65 (1H, m), 0.65 (3H, s).
Melting point (° C): 187-188.

(Example 76)
6-chloro-3- {2-[(cis-2, cis-3-dimethyl) -ref-1-cyclopropyl] phenoxy} -4-pyridazinol (Compound No. 269)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.36-7.11 (4H, m), 6.68 (1H, s), 1.60 (1H, t, J = 8.4 Hz), 1.09-0.93 (8H, m).
Physical properties: amorphous.

(Example 77)
6-Chloro-3- {2-[(cis-2, trans-3-dimethyl) -ref-1-cyclopropyl] phenoxy} -4-pyridazinol (Compound No. 270)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.30-7.09 (4H, m), 6.80 (1H, br.s), 1.56-1.50 (1H, m), 1.10-0.95 (1H, m), 1.03 (3H, s), 0.80-0.67 (1H, m), 0.71 (3H, s).
Melting point (° C): 157-160.

(Example 78)
6-chloro-3- {2-[(trans-2, trans-3-dimethyl) -ref-1-cyclopropyl] phenoxy} -4-pyridazinol (Compound No. 271)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.22-6.96 (4H, m), 6.70 (1H, s), 1.18-0.95 (9H, m).
Melting point (° C): 181-183.

(Example 79)
3- {2-[(ref-1, cis-5, cis-6) -bicyclo [3.1.0] hex-6-yl] phenoxy} -6-chloro-4-pyridazinol (Compound No. 272)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.40-7.05 (4H, m), 6.68 (1H, s), 2.05-1.60 (5H, m), 1.53 (2H, s), 1.35-1.20 (1H , m), 0.25-0.05 (1H, m).
Melting point (° C): 215-240.

(Example 80)
3- {2-[(ref-1, cis-5, trans-6) -bicyclo [3.1.0] hex-6-yl] phenoxy} -6-chloro-4-pyridazinol (Compound No. 273)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.20-7.10 (2H, m), 7.10-6.90 (2H, m), 6.58 (1H, s), 1.80-1.40 (8H, m), 1.20-1.00 ( 1H, m).
Melting point (° C): 137-139.

(Example 81)
3- {2-[(ref-1, cis-6, cis-7) -bicyclo [4.1.0] hept-7-yl] phenoxy} -6-chloro-4-pyridazinol (Compound No. 274)
¹ H-NMR (200MHz, CD ₃ OD) δppm: 7.44 (1H, br.d, J = 6.3Hz), 7.35-7.10 (3H, m), 6.66 (1H, s), 2.00-1.50 (5H, m ), 1.20-1.00 (4H, m), 0.90-0.65 (2H, m).
Melting point (° C):> 260.

(Example 82)
3- {2-[(ref-1, cis-6, trans-7) -bicyclo [4.1.0] hept-7-yl] phenoxy} -6-chloro-4-pyridazinol (Compound No. 275)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.20-7.10 (2H, m), 7.05-6.85 (2H, m), 6.58 (1H, s), 1.90-1.70 (2H, m), 1.60-1.40 ( 3H, m), 1.30-1.05 (6H, m).
Melting point (° C): 191-193.

(Example 83)
6-Chloro-3- {2-[(2,2, cis-3-trimethyl) -ref-1-cyclopropyl] phenoxy} -4-pyridazinol (Compound No. 279)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 7.30-7.00 (4H, m), 6.56 (1H, s), 1.42-1.22 (2H, m), 1.05-0.70 (9H, m).
Melting point (° C): 118-120.

(Example 84)
6-Chloro-3- {2-[(2,2, trans-3-trimethyl) -ref-1-cyclopropyl] phenoxy} -4-pyridazinol (Compound No. 280)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.26-7.06 (4H, m), 6.59 (1H, s), 1.70-1.50 (1H, m), 1.30-1.25 (1H, m), 1.09 (3H, s), 0.96 (3H, s), 0.75 (3H, s).
Melting point (° C): 160-162.

(Example 85)
6-Chloro-3- (2-cyclobutylphenoxy) -4-pyridazinol (Compound No. 284)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.43-7.30 (1H, m), 7.30-7.18 (2H, m), 7.08-6.98 (1H, m), 6.69 (1H, s), 3.68-3.50 (1H, m), 2.25-1.70 (6H, m).
Melting point (° C): 188-189.

(Example 86)
1- {2-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] phenyl} cyclobutanecarbonitrile (Compound No. 287)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.50-7.20 (5H, m), 2.70-1.80 (6H, m).
Melting point (° C): 213-215.

(Example 87)
1- {2-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] phenyl} cyclobutanecarboxylic acid (Compound No. 288)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.42-7.35 (1H, m), 7.35-7.20 (2H, m), 7.08-7.03 (1H, m), 6.66 (1H, s), 2.80-2.45 (4H, m), 2.22-1.95 (1H, m), 1.90-1.70 (1H, m).
Melting point (° C): 173-175.

(Example 88)
6-Chloro-3- (2-cyclopentylphenoxy) -4-pyridazinol (Compound No. 292)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.41-7.35 (1H, m), 7.25-7.17 (2H, m), 7.08-7.02 (1H, m), 6.70 (1H, s), 3.14-3.06 (1H, m), 1.98-1.52 (8H, m).
Melting point (° C): 178-180.

Example 89
6-Chloro-3- (2-cyclohexylphenoxy) -4-pyridazinol (Compound No. 293)
¹ H-NMR (60 MHz, CDCl ₃ + DMF-d ₇ ) δ ppm: 7.40-6.70 (4H, m), 6.55 (1H s), 2.75 (1H, br.s), 2.10-0.90 (10H, m).
Melting point (° C): 158-159.

(Example 90)
6-Chloro-3- [2- (trifluoromethyl) phenoxy] -4-pyridazinol (Compound No. 300)
¹ H-NMR (90 MHz, CD ₃ OD) δ ppm: 7.76-7.27 (4H, m), 6.75 (1H, s), 5.47 (1H, s).
Melting point (° C): 188.

(Example 91)
6-Chloro-3- [2- (1-propenyl) phenoxy} -4-pyridazinol (Compound No. 305)
¹ H-NMR (60 MHz, DMF-d ₇ ) δppm: 7.70-6.90 (5H, m), 6.76 (1H, s), 6.50-6.20 (2H, m), 1.81 (3H, d, J = 5.0 Hz) .
Melting point (° C): 204-206.

(Example 92)
3- (2-Allylphenoxy) -6-chloro-4-pyridazinol (Compound No. 307)
¹ H-NMR (60 MHz, DMF-d ₇ ) δppm: 7.46-7.24 (4H, m), 6.96 (1H s), 6.20-5.60 (1H, m), 5.20-4.80 (2H, m), 3.46-3.26 (2H, m).
Melting point (° C): 200-202.5.

(Example 93)
6-Chloro-3- [2- (1-propynyl) phenoxy] -4-pyridazinol (Compound No. 309)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.43-7.32 (2H, m), 7.23-7.16 (2H, m), 6.73 (1H, s), 1.87 (3H, s).
Melting point (° C): 182-284.

(Example 94)
6-Chloro-3- [2- (cyclopropylmethyl) phenoxy] -4-pyridazinol (Compound No. 311)
¹ H-NMR (200MHz, DMSO-d ₆ ) δppm: 7.45 (1H, dd, J = 7.3, 1.8Hz), 7.31-7.17 (2H, m), 7.10 (1H, dd, J = 7.3, 1.8Hz) , 2.38 (2H, d, J = 7.0Hz), 1.00-0.88 (1H, m), 0.50-0.40 (2H, m), 0.22-0.11 (2H, m).
Melting point (° C): 165-168.

(Example 95)
3- (2-Benzylphenoxy) -6-chloro-4-pyridazinol (Compound No. 315)
Melting point (° C): 185-187.

Example 96
6-Chloro-3- [2- (methoxymethyl) phenoxy] -4-pyridazinol (Compound No. 324)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.47 (1H, br.d, J = 7.7Hz), 7.42-7.20 (2H, m), 7.15 (1H, br.d, J = 7.7Hz) , 6.83 (1H, br.s), 4.35 (2H, s), 3.23 (3H, s).
Melting point (° C): 211-212.

(Example 97)
6-Chloro-3- [2- (ethoxymethyl) phenoxy] -4-pyridazinol (Compound No. 325)
¹ H-NMR (200MHz, DMSO-d ₆ ) δppm: 7.47 (1H, br.d, J = 7.7Hz), 7.42-7.20 (2H, m), 7.16 (1H, br.d, J = 7.7Hz) , 6.82 (1H, br.s), 4.38 (2H, s), 3.39 (2H, q, J = 7.0Hz), 1.03 (3H, t, J = 7.0Hz).
Melting point (° C): 173-174.

(Example 98)
6-Chloro-3- [2- (1,3-dioxolan-2-yl) phenoxy] -4-pyridazinol (Compound No. 329)
Melting point (° C): 143-145.

Example 99
1- {2-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] phenyl} ethanone O-methyloxime (Compound No. 334)
¹ H-NMR (200MHz, DMSO-d ₆ ) δppm: 7.47 (2H, t, J = 7.7Hz), 7.31 (1H, d, J = 7.7Hz), 7.24 (1H, d, J = 7.7Hz), 6.85 (1H, br.s), 3.76 (2.8H, s), 3.58 (0.2H, s), 2.02 (2.8H, s), 1.99 (0.2H, s).
Melting point (° C): 165-167.

(Example 100)
Methyl 2-[(6-chloro-4-hydroxy-3-pyridazinyl) oxy] benzoate (Compound No. 339)
¹ H-NMR (60 MHz, CDCl ₃ + DMF-d ₇ ) δ ppm: 8.10-7.18 (4H, m), 6.80 (1H, s), 5.75 (1H, br.s), 3.70 (3H, s).
Melting point (° C): 188-191.

(Example 101)
3-([1,1'-biphenyl] -2-yloxy) -6-chloro-4-pyridazinol (Compound No. 344)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 7.30-6.70 (10H, m), 6.25 (1H, s).
Melting point (° C): 98-100.

(Example 102)
6-Chloro-3-{[3 '-(trifluoromethyl) [1,1'-biphenyl] -2-yl] oxy} -4-pyridazinol (Compound No. 348)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 7.65-7.58 (2H, m), 7.51-7.26 (5H, m), 7.12-7.06 (1H, m), 6.41 (1H, br.s).
Physical properties: Pasty.

(Example 103)
6-Chloro-3-{[3 '-(trifluoromethyl) [1,1'-biphenyl] -2-yl] oxy} -4-pyridazinol (Compound No. 349)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 7.71-7.64 (2H, m), 7.55-7.30 (5H, m), 7.20-7.13 (1H, m), 6.43 (1H, s).
Physical properties: Pasty.

(Example 104)
6-Chloro-3- [2- (1-pyrrolidinyl) phenoxy] -4-pyridazinol (Compound No. 355)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.19-6.73 (4H, m), 5.64 (1H, s), 3.32-3.25 (4H, m), 1.91-1.84 (4H, m).
Physical properties: amorphous.

(Example 105)
6-Chloro-3- [2- (1H-pyrrol-1-yl) phenoxy] -4-pyridazinol (Compound No. 356)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.41-7.27 (4H, m), 6.95-6.93 (2H, m), 6.46 (1H, m), 6.10-6.08 (2H, m).
Physical properties: amorphous.

(Example 106)
6-Chloro-3- [2- (2-thienyl) phenoxy] -4-pyridazinol (Compound No. 359)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 7.68-7.60 (1H, m), 7.45-7.05 (5H, m), 7.01-6.95 (1H, m), 6.52 (1H, s).
Physical properties: amorphous.

(Example 107)
6-Chloro-3- [2- (3-thienyl) phenoxy] -4-pyridazinol (Compound No. 361)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.46-7.37 (3H, m), 7.30-7.15 (4H, m).
Melting point (° C): 207-209.

(Example 108)
6-Chloro-3- [2- (1H-pyrazol-1-yl) phenoxy] -4-pyridazinol (Compound No. 362)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 8.09 (1H, d, J = 2.2 Hz), 7.70 (1H, dd, J = 7.5, 2.4 Hz), 7.62 (1H, d, J = 2.2 Hz) , 7.50-7.27 (3H, m), 6.55 (1H, s), 6.39 (1H, t, J = 2.2Hz).
Physical properties: amorphous.

(Example 109)
6-Chloro-3- [2- (3,5-dimethyl-1H-pyrazol-1-yl) phenoxy] -4-pyridazinol (Compound No. 364)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.60-7.32 (4H, m), 6.52 (1H, s), 5.86 (1H, s), 2.17 (3H, s), 2.10 (3H, s).
Physical properties: amorphous.

(Example 110)
6-Chloro-3- {2- [3- (trifluoromethyl) -1H-pyrazol-1-yl] phenoxy} -4-pyridazinol (Compound No. 365)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.79 (1H, br.s), 7.70-7.35 (5H, m), 7.06 (1H, br.s), 6.68 (1H, s).
Physical properties: amorphous.

(Example 111)
6-chloro-3- {2- [4- (trifluoromethyl) -1H-pyrazol-1-yl] phenoxy} -4-pyridazinol (Compound No. 366)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 8.75 (1H, s), 8.11 (1H, s), 7.80-7.74 (1H, m), 7.58-7.38 (3H, m), 6.77 (1H, s).
Physical property: Oily substance.

(Example 112)
6-chloro-3- {2- [5- (trifluoromethyl) -1H-pyrazol-1-yl] phenoxy} -4-pyridazinol (Compound No. 367)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 8.30 (1H, br.s), 7.83-7.72 (1H, m), 7.60-7.40 (3H, m), 6.91 (1H, br.d, J = 2.6Hz), 6.78 (1H, s).
Physical properties: amorphous.

(Example 113)
5- {2-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] phenyl} -N, N-dimethyl-1H-pyrazole-1-sulfonamide (Compound No. 369)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.87 (1H, d, J = 2.6Hz), 7.78 (1H, dd, J = 7.3, 1.8Hz), 7.65-7.35 (3H, m), 7.20 (1H , s), 7.03 (1H, d, J = 2.6 Hz), 2.86 (6H, s).
Melting point (° C): 151-152.

(Example 114)
3- {2-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] phenyl} -N, N-dimethyl-1H-pyrazole-1-sulfonamide (Compound No. 368)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 9.19 (1H, d, J = 2.9Hz), 8.12 (1H, s), 7.97 (1H, dd, J = 7.3, 2.2Hz), 7.61 (1H, d , J = 1.5Hz), 7.50-7.33 (2H, m), 6.98 (1H, d, J = 2.9Hz), 2.83 (6H, s).
Melting point (° C): 210-212.

(Example 115)
6-Chloro-3- [2- (4-methyl-1,3-thiazol-2-yl) phenoxy] -4-pyridazinol (Compound No. 370)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.17 (1H, d, J = 7.7Hz), 7.73 (1H, d, J = 7.7Hz), 7.47 (1H, t, J = 7.7Hz), 7.28 ( 1H, t, J = 7.7Hz), 7.02 (1H, s), 6.98 (1H, s), 2.56 (3H, s).
Physical properties: amorphous.

(Example 116)
3- [2- (1,3-Benzoxazol-2-yl) phenoxy] -6-chloro-4-pyridazinol (Compound No. 375)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 8.31 (1H, dd, J = 7.9, 1.6 Hz), 7.73-7.30 (7H, m), 6.78 (1H, s).
Melting point (° C): 165-167.

(Example 117)
3- [2- (1,3-Benzothiazol-2-yl) phenoxy] -6-chloro-4-pyridazinol (Compound No. 376)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.12 (1H, d, J = 7.7Hz), 8.00-7.84 (1H, m), 7.78 (1H, d, J = 7.7Hz), 7.62-7.30 (5H m), 7.05 (1H, br.s).
Melting point (° C): 215-217.

(Example 118)
6-Chloro-3- [2- (dimethylamino) phenoxy] -4-pyridazinol (Compound No. 379)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.17-6.96 (4H, m), 6.61 (1H, s), 2.75 (6H, s).
Physical properties: amorphous.

(Example 119)
6-Chloro-3- (2-nitrophenoxy) -4-pyridazinol (Compound No. 383)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 8.16 (1H, d, J = 6.0 Hz), 7.90-7.33 (3H, m), 6.78 (1H, s).
Melting point (° C): 99-100.

(Example 120)
6-Chloro-3- (2-ethynylphenoxy) -4-pyridazinol (Compound No. 308)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.57-7.41 (2H, m), 7.30-7.20 (2H, m), 6.71 (1H, s), 3.60 (1H, s).
Melting point (° C): 189-191.

(Example 121)
6-Chloro-3- (2-methoxyphenoxy) -4-pyridazinol (Compound No. 385)
¹ H-NMR (60 MHz, CDCl ₃ + DMF-d ₇ ) δ ppm: 7.30-6.80 (4H, m), 6.55 (1H, s), 3.69 (3H, s).
Melting point (° C): 191-194.

(Example 122)
6-Chloro-3- (2-ethoxyphenoxy) -4-pyridazinol (Compound No. 386)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.26-7.02 (2H, m), 6.98-6.85 (2H, m), 6.57 (1H, s), 5.35 (1H, br.s), 3.92 (2H, q, J = 7.0Hz), 1.18 (t, 3H, J = 7.0Hz).
Melting point (° C): 155-175.

(Example 123)
6-Chloro-3- (2-isopropoxyphenoxy) -4-pyridazinol (Compound No. 387)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.28-7.10 (3H, m), 6.97 (1H, td, J = 7.3, 2.3 Hz), 6.83 (1H, br.s), 4.52 (1H, septet, J = 6.2Hz), 1.07 (6H, d, J = 6.2Hz).
Melting point (° C): 178-179.

(Example 124)
6-Chloro-3- [2- (difluoromethoxy) phenoxy] -4-pyridazinol (Compound No. 390)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 7.40 (4H, s), 6.63 (1H, s), 6.53 (1H, t, J = 73.8 Hz).
Melting point (° C): 210-212.

(Example 125)
6-Chloro-3- [2- (trifluoromethoxy) phenoxy] -4-pyridazinol (Compound No. 391)
^{1 H-NMR (200MHz, CDCl} 3 + CD 3 OD) δppm: 7.38-7.20 (4H, m), 6.60 (1H, s).
Melting point (° C): 215.

(Example 126)
6-Chloro-3- [2- (2-methoxyethoxy) phenoxy] -4-pyridazinol (Compound No. 396)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.26-6.93 (4H, m), 6.62 (1H, s), 4.78-4.03 (2H, m), 3.55-3.50 (2H, m), 3.24 (3H , s).
Physical properties: Pasty.

(Example 127)
6-Chloro-3- [2- (2-hydroxyphenoxy) phenoxy] -4-pyridazinol (Compound No. 399)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.27-6.75 (8H, m), 6.61 (1H, s).
Physical properties: amorphous.

(Example 128)
6-chloro-3- {2- {2-[(6-chloro-4-ethoxy-3-pyridazinyl) oxy] phenoxy} phenoxy} -4-pyridazinol (Compound No. 400)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.65-6.70 (8H, m), 6.63-6.59 (2H, m), 4.19 (2H, q, J = 7.0Hz), 1.50 (3H, t, J = 7.0Hz).
Physical properties: amorphous.

(Example 129)
6-Chloro-3- [2- (methylsulfanyl) phenoxy] -4-pyridazinol (Compound No. 401)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.43-7.11 (4H, m), 6.71 (1H, s), 2.40 (3H, s).
Melting point (° C): 174-175.

(Example 130)
6-Chloro-3- [2- (isopropylsulfanyl) phenoxy] -4-pyridazinol (Compound No. 403)
Melting point (° C): 176-177.

(Example 131)
6-Chloro-3- (2-cyanophenoxy) -4-pyridazinol (Compound No. 330)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.82-7.68 (2H, m), 7.46-7.34 (2H, m), 6.79 (1H, s).
Physical properties: amorphous.

(Example 132)
1- {2- [6-Chloro-4-hydroxy-3-pyridazinyl] oxy} phenyl} ethanone (Compound No. 336)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.88-7.85 (1H, m), 7.65-7.57 (1H, m), 7.43-7.26 (2H, m), 6.73 (1H, s), 2.50 (3H, br.s).
Melting point (° C): 186-189.

(Example 133)
6-Chloro-3- (3-chlorophenoxy) -4-pyridazinol (Compound No. 410)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.45-7.10 (5H, m), 6.72 (1H, s).
Melting point (° C): 217.

(Example 134)
6-Chloro-3- (3-iodophenoxy) -4-pyridazinol (Compound No. 412)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.64-7.53 (2H, m), 7.28-6.70 (3H, m).
Melting point (° C): 202-203.

(Example 135)
6-Chloro-3- (3-methylphenoxy) -4-pyridazinol (Compound No. 413)
¹ H-NMR (60 MHz, DMF-d ₇ ) δ ppm: 7.35-6.80 (4H, m), 6.95 (1H, s), 2.35 (3H, s).
Melting point (° C): 205-208.

(Example 136)
6-Chloro-3- (3-isopropylphenoxy) -4-pyridazinol (Compound No. 415)
Melting point (° C): 176-177.

(Example 137)
3- (3-tert-Butylphenoxy) -6-chloro-4-pyridazinol (Compound No. 416)
¹ H-NMR (60 MHz, DMSO-d ₆ ) δ ppm: 7.40-6.65 (4H, m), 6.67 (1H, s), 1.27 (9H, s).
Melting point (° C): 203-207.

(Example 138)
6-Chloro-3- (3-cyclopropylphenoxy) -4-pyridazinol (Compound No. 417)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.35-7.20 (1H, m), 6.98-6.85 (3H, m), 6.78 (1H, br.s), 2.00-1.88 (1H, m), 0.98-0.87 (2H, m), 0.70-0.60 (2H, m).
Melting point (° C): 179-181.

(Example 139)
6-Chloro-3- [3- (trifluoromethyl) phenoxy] -4-pyridazinol (Compound No. 418)
¹ H-NMR (60 MHz, DMF-d ₇ ) δ ppm: 7.70-7.40 (4H, m), 6.95 (1H, s).
Melting point (° C): 213-216.

(Example 140)
6-Chloro-3- [3- (2-furyl) phenoxy] -4-pyridazinol (Compound No. 419)
¹ H-NMR (200 MHz, CDCl ₃ + CD ₃ OD) δppm: 7.55-7.35 (4H, m), 7.08-7.02 (1H, m), 6.67 (1H, d, J = 3.3Hz), 6.59 (1H, br.s), 6.48 (1H, dd, J = 3.3, 1.8 Hz).
Melting point (° C): 200-202.

(Example 141)
3-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] benzonitrile (Compound No. 420)
¹ H-NMR (90 MHz, CD ₃ OD) δ ppm: 7.70-7.40 (4H, m), 6.75 (1H, s).
Melting point (° C): 226-229.

(Example 142)
3-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] benzaldehyde (Compound No. 421)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 9.96 (1H, s), 7.72-7.53 (3H, m), 7.46-7.41 (1H, m), 6.54 (1H, s).
Melting point (° C): 188-192.

(Example 143)
1- {3-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] phenyl} ethanone (Compound No. 422)
Melting point (° C): 195-198.

(Example 144)
Methyl 3-[(6-chloro-4-hydroxy-3-pyridazinyl) oxy] benzoate (Compound No. 423)
¹ H-NMR (90 MHz, CD ₃ OD) δ ppm: 8.00-7.70 (2H, m), 7.70-7.30 (2H, m), 6.75 (1H, s), 3.30 (3H, s).
Melting point (° C): 207.

(Example 145)
6-Chloro-3- (3-nitrophenoxy) -4-pyridazinol (Compound No. 424)
¹ H-NMR (60 MHz, DMF-d ₇ ) δ ppm: 8.30-7.90 (2H, m), 7.90-7.70 (2H, m), 6.50 (1H, s), 5.80-5.15 (1H, br.s).
Melting point (° C): 217-219.

(Example 146)
6-Chloro-3- (3-methoxyphenoxy) -4-pyridazinol (Compound No. 425)
¹ H-NMR (60 MHz, CDCl ₃ + DMF-d ₇ ) δppm: 7.50-7.10 (1H, m), 6.90-6.60 (3H, m), 6.70 (1H, s), 5.88 (1H, br.s) , 3.77 (3H, s).
Melting point (° C): 199-203.

(Example 147)
6-Chloro-3- (4-chlorophenoxy) -4-pyridazinol (Compound No. 427)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.45-7.38 (2H, m), 7.23-7.15 (2H, m), 6.70 (1H, s).
Melting point (° C): 226-231.

(Example 148)
6-Chloro-3- (4-methylphenoxy) -4-pyridazinol (Compound No. 430)
¹ H-NMR (60 MHz, DMSO-d ₆ ) δ ppm: 7.25-6.83 (4H, m), 6.68 (1H, s), 2.25 (3H, s).
Melting point (° C): 261-263.

(Example 149)
6-Chloro-3- (4-isopropylphenoxy) -4-pyridazinol (Compound No. 432)
Melting point (° C): 233-235.

(Example 150)
3- (4-tert-Butylphenoxy) -6-chloro-4-pyridazinol (Compound No. 433)
Melting point (° C): 224-225.

(Example 151)
6-Chloro-3- (4-cyclopropylphenoxy) -4-pyridazinol (Compound No. 434)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.15–7.02 (4H, m), 6.82 (1H, br.s), 2.01-1.90 (1H, m), 0.99-0.90 (2H, m), 0.70-0.62 (2H, m)
Melting point (° C): 221-227.

(Example 152)
6-Chloro-3- (4-methoxyphenoxy) -4-pyridazinol (Compound No. 435)
¹ H-NMR (60 MHz, DMF-d ₇ ) δ ppm: 7.26-6.85 (4H, m), 6.80 (1H, br.s), 3.81 (3H, s).
Melting point (° C): 260-263.5.

(Example 153)
6-Chloro-3- [4- (trimethylsilyl) phenoxy] -4-pyridazinol (Compound No. 436)
Melting point (° C): 197-199.

(Example 154)
6-Chloro-3- (2,3-difluorophenoxy) -4-pyridazinol (Compound No. 437)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.24-7.05 (3H, m), 6.73 (1H, s).
Melting point (° C): 188-193.

(Example 155)
6-Chloro-3- (3-chloro-2-fluorophenoxy) -4-pyridazinol (Compound No. 438)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.43–7.21 (3H, m), 6.75 (1H, s).
Melting point (° C): 187-195.

(Example 156)
6-Chloro-3- [2-fluoro-3- (trifluoromethyl) phenoxy] -4-pyridazinol (Compound No. 441)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.78-7.66 (2H, m), 7.48 (1H, t, J = 8.1 Hz), 6.83 (1H, s).
Melting point (° C): 185-189.

(Example 157)
6-Chloro-3- (2,3-dichlorophenoxy) -4-pyridazinol (Compound No. 443)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.62-7.57 (1H, m), 7.50-7.37 (2H, m), 6.89 (1H, s).
Melting point (° C): 233-238.

(Example 158)
6-Chloro-3- [2-chloro-3- (trifluoromethyl) phenoxy] -4-pyridazinol (Compound No. 446)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.74-7.55 (3H, m), 6.76 (1H, s).
Melting point (° C): 170-200.

(Example 159)
3- (2-Bromo-3-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 450)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.35 (1H, t, J = 7.5 Hz), 7.27 (1H, dd, J = 7.5, 2.2 Hz), 7.16 (1H, dd, J = 7.5, 2.2Hz), 6.87 (1H, br.s), 2.41 (3H, s).
Melting point (° C): 140-141.

(Example 160)
6-Chloro-3- (3-fluoro-2-methylphenoxy) -4-pyridazinol (Compound No. 453)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.30-7.15 (1H, m), 7.08-6.85 (2H, m), 6.73 (1H, s), 2.09 (3H, d, J = 1.8 Hz).
Melting point (° C): 242-244.

(Example 161)
6-Chloro-3- (3-chloro-2-methylphenoxy) -4-pyridazinol (Compound No. 454)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.39-7.12 (4H, m), 2.14 (3H, s).
Melting point (° C): 250-252.

(Example 162)
6-Chloro-3- (2,3-dimethylphenoxy) -4-pyridazinol (Compound No. 456)
¹ H-NMR (60 MHz, DMSO-d ₆ ) δ ppm: 7.22-6.98 (3H, m), 6.77 (1H, s), 2.30 (3H, s), 2.02 (3H, s).
Melting point (° C): 240-241.

(Example 163)
6-Chloro-3- (2-methyl-3-nitrophenoxy) -4-pyridazinol (Compound No. 458)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.89-7.84 (1H, m), 7.58-7.47 (2H, m), 6.90 (1H, br.s), 2.25 (3H, s).
Melting point (° C): 241-244.

(Example 164)
6-Chloro-3- (3-methoxy-2-methylphenoxy) -4-pyridazinol (Compound No. 459)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.14 (1H, t, J = 8.4 Hz), 6.78 (1H, d, J = 8.4 Hz), 6.63 (1H, d, J = 8.4 Hz), 6.55 (1H, s), 3.83 (3H, s), 2.00 (3H, s).
Melting point (° C): 224-237.

(Example 165)
6-chloro-3- {3-[(6-chloro-4-hydroxy-3-pyridazinyl) oxy] -2-methylphenoxy} -4-pyridazinol (Compound No. 460)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.16 (1H, t, J = 8.4 Hz), 6.85 (2H, d, J = 8.4 Hz), 6.48 (2H, s), 2.15 (3H, s) .
Melting point (° C):> 290.

(Example 166)
6-Chloro-3- (2-cyclopropyl-3-methylphenoxy) -4-pyridazinol (Compound No. 472)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.18 (1H, t, J = 7.7 Hz), 7.07 (1H, br.d, J = 7.7 Hz), 6.91 (1H, br.d, J = 7.7Hz), 6.82 (1H, br.s), 2.40 (3H, s), 1.43-1.28 (1H, m), 0.79-0.68 (2H, m), 0.59-0.48 (2H, m).
Melting point (° C): 197-198.

(Example 167)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl tetrahydro-2H-pyran-4-carboxylate (Compound No. 3856)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.38 (1H, s), 7.15-7.04 (2H, m), 6.90-6.78 (1H, m), 4.10-3.95 (2H, m), 3.60-3.43 ( 2H, m), 3.03-2.86 (1H, m), 2.11 (3H, s), 2.06-1.90 (4H, m), 1.80-1.60 (1H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 168)
Methyl 2-[(6-chloro-4-hydroxy-3-pyridazinyl) oxy] -6-fluorobenzoate (Compound No. 491)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.62 (1H, td, J = 8.4, 5.6 Hz), 7.23 (1H, t, J = 8.4 Hz), 7.02 (1H, d, J = 8.4 Hz), 3.83 (3H, s).
Physical properties: amorphous.

(Example 169)
6-Chloro-3- (3-methyl-2-nitrophenoxy) -4-pyridazinol (Compound No. 498)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.48 (1H, t, J = 8.1 Hz), 7.26 (1H, d, J = 8.1 Hz), 7.19 (1H, d, J = 8.1 Hz), 6.66 (1H, s), 2.37 (3H, s).
Melting point (° C): 191-200.

(Example 170)
6-Chloro-3- (2,3-dimethoxyphenoxy) -4-pyridazinol (Compound No. 503)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.14-6.78 (4H, m), 3.84 (3H, s), 3.61 (3H, s).
Melting point (° C): 199-201.

(Example 171)
6-Chloro-3- (2,3-dihydro-1H-inden-4-yloxy) -4-pyridazinol (Compound No. 506)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.20 (1H, t, J = 7.3 Hz), 7.14 (1H, d, J = 7.3 Hz), 6.92 (1H, d, J = 7.3 Hz), 6.83 (1H, br.s), 2.92 (2H, t, J = 7.3Hz), 2.64 (2H, t, J = 7.3Hz), 2.00 (2H, quintet, J = 7.3Hz).
Melting point (° C): 230-232.

(Example 172)
6-Chloro-3-[(3-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinol (Compound No. 507)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.17 (1H, t, J = 7.7 Hz), 7.08 (1H, d, J = 7.7 Hz), 6.88 (1H, d, J = 7.7 Hz), 6.69 (1H, s), 3.35-3.15 (1H, m), 3.10-2.70 (2H, m), 2.40-2.15 (1H, m), 1.80-1.55 (1H, m), 1.15 (3H, d, J = 7.0Hz).
Melting point (° C): 232.

(Example 173)
6-Chloro-3-[(1-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinol (Compound No. 510)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.21 (1H, dd, J = 8.1, 7.3 Hz), 7.09 (1H, d, J = 7.3 Hz), 6.91 (1H, d, J = 8.1 Hz) , 6.70 (1H, s), 3.30-3.05 (1H, m), 2.85-2.50 (2H, m), 2.40-2.20 (1H, m), 1.70-1.45 (1H, m), 1.29 (3H, d, J = 7.0Hz).
Melting point (° C): 228-230.

(Example 174)
6-Chloro-3-[(2,2-dimethyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinol (Compound No. 513)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.17 (1H, t, J = 7.7 Hz), 7.05 (1H, d, J = 7.7 Hz), 6.89 (1H, d, J = 7.7 Hz), 6.69 (1H, s), 2.76 (2H, s), 2.53 (2H, s), 1.13 (6H, s).
Melting point (° C): 220-223.

(Example 175)
6-Chloro-3- {spiro [cyclopropane-1,3 '-(2', 3'-dihydro-1'H-indene)]-4'-yloxy} -4-pyridazinol (Compound No. 514)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.15-6.95 (2H, m), 6.75 (1H, dd, J = 6.6, 2.6 Hz), 6.66 (1H, s), 3.02 (2H, dd, J = 7.7, 7.3Hz), 2.15-1.95 (2H, m), 1.28-1.15 (2H, m), 0.80-0.70 (2H, m).
Physical properties: amorphous.

(Example 176)
6-Chloro-3- (4-fluorophenoxy) -4-pyridazinol (Compound No. 426)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.26-7.05 (4H, m), 6.70 (1H, s).
Melting point (° C): 241-248.

(Example 177)
3- (Bicyclo [4.2.0] octa-1,3,5-trien-2-yloxy) -6-chloro-4-pyridazinol (Compound No. 505)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.22 (1H, dd, J = 8.2, 7.3 Hz), 6.96 (1H, d, J = 8.2 Hz), 6.91 (1H, d, J = 7.3 Hz) , 6.69 (1H, s), 3.19-3.11 (2H, m), 3.10-3.00 (2H, m).
Melting point (° C): 145-155.

(Example 178)
7-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] -2,3-dihydro-1H-inden-1-one O-methyloxime (Compound No. 520)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.50-7.15 (2H, m), 7.07 (1H, dd, J = 8.1, 7.3 Hz), 6.55 (0.4H, s), 5.77 (0.6H, s ), 3.73 (1.8H, s), 3.67 (1.2H, s), 3.15-3.00 (2H, m), 2.90-2.73 (2H, m).
Melting point (° C):> 250.

(Example 179)
6-Chloro-3- (5,6,7,8-tetrahydro-1-naphthalenyloxy) -4-pyridazinol (Compound No. 521)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.14 (1H, t, J = 7.7 Hz), 6.98 (1H, d, J = 7.7 Hz), 6.89 (1H, d, J = 7.7 Hz), 6.82 (1H, br.s), 2.80-2.70 (2H, m), 2.50-2.40 (2H, m), 1.85-1.70 (4H, m).
Melting point (° C): 232-237.

(Example 180)
6-Chloro-3- (1-naphthyloxy) -4-pyridazinol (Compound No. 527)
¹ H-NMR (60 MHz, DMSO-d ₆ ) δ ppm: 8.10-7.20 (7H, m), 6.85 (1H, s), 6.20 (1H, br.s).
Melting point (° C): 243-245.

(Example 181)
6-Chloro-3- (2,3-dihydro-1-benzofuran-4-yloxy) -4-pyridazinol (Compound No. 528)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.11 (1H, t, J = 8.1 Hz), 6.65 (1H, s), 6.60 (1H, d, J = 8.1 Hz), 6.56 (1H d, J = 8.1Hz), 4.53 (2H, t, J = 8.5Hz), 2.97 (2H, t, J = 8.5Hz).
Melting point (° C): 219-221.

(Example 182)
6-Chloro-3-[(3-methyl-2,3-dihydro-1-benzofuran-4-yl) oxy] -4-pyridazinol (Compound No. 529)
¹ H-NMR (200MHz, DMSO-d ₆ ) δppm: 7.15 (1H, t, J = 8.1Hz), 6.85 (1H, br.s), 6.67 (1H, d, J = 8.1Hz), 6.62 (1H , d, J = 8.1Hz), 4.65 (1H, t, J = 8.8Hz), 4.12-4.04 (1H, m), 3.50-3.39 (1H, m), 1.14 (3H, d, J = 7.0Hz) .
Melting point (° C): 238-245.

(Example 183)
3- (1-Benzofuran-4-yloxy) -6-chloro-4-pyridazinol (Compound No. 531)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.99 (1H, d, J = 2.0 Hz), 7.52 (1H, d, J = 7.8 Hz), 7.35 (1H, t, J = 7.8 Hz), 7.06 (1H, d, J = 7.8Hz), 6.87 (1H, s), 6.81 (1H, d, J = 2.0Hz).
Melting point (° C): 220-225.

(Example 184)
6-Chloro-3-[(3-methyl-1-benzofuran-4-yl) oxy] -4-pyridazinol (Compound No. 532)
¹ H-NMR (200MHz, CD ₃ OD) δppm: 7.44 (1H, d, J = 1.5Hz), 7.33-7.20 (2H, m), 6.91 (1H, dd, J = 7.0, 1.5Hz), 6.61 ( 1H, s), 2.01 (3H, s).
Melting point (° C): 218-225.

(Example 185)
3- (1-Benzothienen-4-yloxy) -6-chloro-4-pyridazinol (Compound No. 534)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.75 (1H, d, J = 8.1 Hz), 7.53 (1H, d, J = 5.5 Hz), 7.35 (1H, dd, J = 8.1, 7.7 Hz) , 7.28 (1H, dd, J = 5.5, 0.7Hz), 7.10 (1H, dd, J = 7.7, 0.7Hz), 6.64 (1H, s).
Melting point (° C): 181-183.

(Example 186)
6-Chloro-3- (8-quinolinyloxy) -4-pyridazinol (Compound No. 535)
¹ H-NMR (200MHz, DMSO-d ₆ ) δppm: 8.80 (1H, dd, J = 4.0, 1.5Hz), 8.46 (1H, dd, J = 8.4, 1.5Hz), 7.93-7.87 (1H, m) , 7.70-7.63 (2H, m), 7.57 (1H, dd, J = 8.4, 4.0Hz), 6.82 (1H, s).
Melting point (° C):> 200 (dec.).

(Example 187)
6-Chloro-3- (8-quinolinyloxy) -4-pyridazinol (Compound No. 536)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 8.81 (1H, dd, J = 4.0, 1.5 Hz), 8.41 (1H, dd, J = 8.4, 1.5 Hz), 7.81 (1H, d, J = 7.0Hz), 7.62-7.52 (2H, m), 7.41 (1H, d, J = 7.7Hz), 6.43 (1H, s).
Melting point (° C):> 180 (dec.).

(Example 188)
6-Chloro-3-[(2-methyl-1,3-benzoxazol-4-yl) oxy] -4-pyridazinol (Compound No. 538)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.55-7.32 (2H, m), 7.22-7.10 (1H, m), 6.73 (1H, s), 2.59 (3H, s).
Melting point (° C): 221-222.

(Example 189)
6-Chloro-3- (2,3-dihydro-1-benzofuran-7-yloxy) -4-pyridazinol (Compound No. 539)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.13-7.08 (1H, m), 6.95 (1H, d, J = 7.3 Hz), 6.85 (1H, dd, J = 8.1, 7.3 Hz), 6.67 ( 1H, s), 4.54 (2H, t, J = 8.4Hz), 3.30-3.20 (2H, m).
Physical properties: amorphous.

(Example 190)
6-Chloro-3-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl) oxy] -4-pyridazinol (Compound No. 540)
¹ H-NMR (200MHz, DMSO-d ₆ ) δppm: 7.08 (1H, d, J = 7.3Hz), 6.96 (1H, d, J = 8.1Hz), 6.87-6.79 (2H, m), 3.06 (2H , s), 1.37 (6H, s).
Melting point (° C): 228-229.5.

(Example 191)
3- (1-Benzofuran-7-yloxy) -6-chloro-4-pyridazinol (Compound No. 541)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.73 (1H, d, J = 2.2 Hz), 7.53 (1H, dd, J = 7.7, 1.4 Hz), 7.26 (1H, t, J = 7.7 Hz) , 7.15 (1H, dd, J = 7.7, 1.4 Hz), 6.90 (1H, d, J = 2.2 Hz), 6.76 (1H, s).
Melting point (° C): 201-202.

(Example 192)
3- (1,3-Benzodioxol-4-yloxy) -6-chloro-4-pyridazinol (Compound No. 544)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 6.94-6.75 (4H, m), 6.01 (2H, s).
Melting point (° C): 206-211.

(Example 193)
6-Chloro-3- (2,3-dihydro-1,4-benzodioxin-5-yloxy) -4-pyridazinol (Compound No. 547)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 6.90-6.72 (4H, m), 4.27-4.15 (4H, m).
Melting point (° C): 218-223.5.

(Example 194)
6-Chloro-3-[(2-methyl-1,3-benzoxazol-7-yl) oxy] -4-pyridazinol (Compound No. 549)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.52 (1H, dd, J = 8.1, 1.1 Hz), 7.37 (1H, t, J = 8.1 Hz), 7.21 (1H, dd, J = 8.1, 1.1 Hz), 6.76 (1H, s), 2.65 (3H, s).
Melting point (° C): 197-202.

(Example 195)
6-Chloro-3- (2,4-dichlorophenoxy) -4-pyridazinol (Compound No. 552)
¹ H-NMR (60 MHz, DMF-d ₇ ) δ ppm: 7.55 (1H, t, J = 1.8 Hz), 7.35 (2H, d, J = 1.8 Hz), 6.88 (1H, s).
Melting point (° C): 233-237.

(Example 196)
3- (2-Bromo-4-tert-butylphenoxy) -6-chloro-4-pyridazinol (Compound No. 556)
¹ H-NMR (60MHz, DMSO-d ₆ ) δppm: 7.61 (1H, d, J = 2.0Hz), 7.43 (1H, dd, J = 8.4, 2.0Hz), 7.17 (1H, d, J = 8.4Hz ), 6.73 (1H, s), 1.32 (9H, s).
Melting point (° C):> 202 (dec.).

(Example 197)
6-Chloro-3- (4-chloro-2-methylphenoxy) -4-pyridazinol (Compound No. 558)
¹ H-NMR (60 MHz, DMSO-d ₆ + CDCl ₃ ) δ ppm: 7.40-7.10 (3H, m), 6.65 (1H, s), 2.18 (3H, s).
Melting point (° C): 235-235.5.

(Example 198)
6-Chloro-3- (2,4-dimethylphenoxy) -4-pyridazinol (Compound No. 559)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 7.17-6.98 (3H, m), 6.85 (1H, s), 2.29 (3H, s), 2.07 (3H, s).
Melting point (° C): 217.5.

(Example 199)
6-Chloro-3- (2-ethyl-4-iodophenoxy) -4-pyridazinol (Compound No. 562)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.59 (1H, d, J = 2.2 Hz), 7.49 (1H, dd, J = 8.4, 2.2 Hz), 6.75 (1H, d, J = 8.4 Hz) , 6.48 (1H, s), 2.65-1.95 (2H, m), 1.16 (3H, t, J = 7.7Hz).
Melting point (° C): 199-201.

(Example 200)
3- (4-Bromo-2-isopropylphenoxy) -6-chloro-4-pyridazinol (Compound No. 566)
¹ H-NMR (60 MHz, DMSO-d ₆ ) δppm: 7.44 (1H, br.s), 7.37 (1H, dd, J = 8.0, 2.2 Hz), 7.00 (1H, d, J = 8.0 Hz), 6.73 (1H, s), 3.01 (1H, septet, J = 6.8Hz), 1.15 (6H, d, J = 6.8Hz).
Melting point (° C): 215-225.

(Example 201)
3- (2-tert-Butyl-4-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 567)
¹ H-NMR (90 MHz, CD ₃ OD) δ ppm: 7.25 (1H, d, J = 2.0 Hz), 7.05 (1H, dd, J = 8.0, 2.0 Hz), 6.85 (1H, d, J = 8.0 Hz) , 6.70 (1H, s), 2.30 (3H, s), 1.35 (9H, s).
Melting point (° C): 230-236.

(Example 202)
6-Chloro-3- (2-cyclopropyl-4-methylphenoxy) -4-pyridazinol (Compound No. 571)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.05-6.95 (1H, m), 6.96 (1H, s), 6.81 (1H, s), 6.68 (1H, m), 2.30 (3H, s), 1.90-1.75 (1H, m), 0.90-0.70 (2H, m), 0.70-0.50 (2H, m).
Melting point (° C): 239.

(Example 203)
6-Chloro-3- (2-chloro-5-methylphenoxy) -4-pyridazinol (Compound No. 614)
¹ H-NMR (90 MHz, CD ₃ OD) δ ppm: 7.40 (1H, d, J = 8.5 Hz), 7.15 (1H, s), 7.10 (1H, d, J = 8.5 Hz), 6.70 (1H, s) , 2.35 (3H, s).
Melting point (° C): 170.

(Example 204)
6-Chloro-3- (5-chloro-2-methylphenoxy) -4-pyridazinol (Compound No. 618)
¹ H-NMR (200MHz, CD ₃ OD) δppm: 7.28 (1H, d, J = 8.8Hz), 7.21-7.15 (1H, m), 7.16 (1H, s), 6.72 (1H, s), 2.15 ( 3H, s).
Melting point (° C): 174-180.

(Example 205)
6-Chloro-3- (2,5-dimethylphenoxy) -4-pyridazinol (Compound No. 621)
¹ H-NMR (90 MHz, CD ₃ OD) δ ppm: 7.16 (1H, d, J = 9.0 Hz), 7.08 (1H, d, J = 9.0 Hz), 6.90 (1H, s), 6.70 (1H, s) , 2.30 (3H, s), 2.10 (3H, s).
Melting point (° C): 80-83.

(Example 206)
6-Chloro-3- (5-isopropyl-2-methylphenoxy) -4-pyridazinol (Compound No. 623)
¹ H-NMR (90 MHz, CD ₃ OD) δ ppm: 7.20 (1H, d, J = 7.5 Hz), 7.15-6.98 (1H, m), 6.95 (1H, s), 6.70 (1H, s), 2.88 ( 1H, septet, J = 7.5Hz), 2.10 (3H, s), 1.23 (6H, d, J = 7.5Hz).
Melting point (° C): 168-169.

(Example 207)
3-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] -4-methylbenzoic acid (Compound No. 626)
Melting point (° C): 238-240.

(Example 208)
3- (5-Amino-2-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 627)
Melting point (° C):> 310.

(Example 209)
6-Chloro-3- [5- (dimethylamino) -2-methylphenoxy] -4-pyridazinol (Compound No. 628)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.08 (1H, d, J = 8.4 Hz), 6.68 (1H, s), 6.61 (1H, dd, J = 8.4, 2.6 Hz), 6.50 (1H, d, J = 2.6Hz), 2.88 (6H, s), 2.02 (3H, s).
Melting point (° C): 181-182.

(Example 210)
6-Chloro-3- (5-methoxy-2-methylphenoxy) -4-pyridazinol (Compound No. 629)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.16 (1H, d, J = 8.4 Hz), 6.78-6.67 (3H, m), 3.75 (3H, s), 2.07 (3H, s).
Melting point (° C): 170-172.

(Example 211)
6-Chloro-3- (2-ethyl-5-methoxyphenoxy) -4-pyridazinol (Compound No. 635)
¹ H-NMR (60 MHz, DMF-d ₇ ) δppm: 7.15 (1H, br.d, J = 8.0 Hz), 6.74 (1H, br.s), 6.73 (1H, br.d, J = 8.0 Hz) , 6.63 (1H, s), 3.73 (3H, s), 2.46 (2H, q, J = 7.0Hz), 1.10 (3H, t, J = 7.0Hz).
Melting point (° C): 124-126.

(Example 212)
6-Chloro-3- (2-isopropyl-5-methylphenoxy) -4-pyridazinol (Compound No. 640)
¹ H-NMR (60 MHz, CDCl ₃ + DMF-d ₇ ) δppm: 7.50-6.70 (3H, m), 6.58 (1H, s), 3.30-2.60 (1H, m), 2.26 (3H, s), 1.13 (6H, d, J = 6.60Hz).
Melting point (° C): 193-195.

(Example 213)
6-Chloro-3- (3,5-diisopropylphenoxy) -4-pyridazinol (Compound No. 642)
¹ H-NMR (60MHz, DMSO-d ₆ ) δppm: 7.25 (1H, d, J = 8.0Hz), 7.11 (1H, d, J = 1.8Hz), 6.92 (1H, dd, J = 8.0, 1.8Hz ), 6.73 (1H, s), 2.84 (2H, septet, J = 7.0Hz), 1.18 (6H, d, J = 7.0Hz), 1.12 (6H, d, J = 7.0Hz).
Melting point (° C): 231-235.

(Example 214)
3- (2-tert-Butyl-5-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 650)
¹ H-NMR (90 MHz, CD ₃ OD) δ ppm: 7.35 (1H, d, J = 8.0 Hz), 6.95 (1H, dd, J = 8.0, 1.5 Hz), 6.80 (1H, s), 6.70 (1H, s), 2.27 (3H, s), 1.35 (9H, s).
Melting point (° C): 226.

(Example 215)
6-Chloro-3- (2,5-ditert-butylphenoxy) -4-pyridazinol (Compound No. 653)
¹ H-NMR (60 MHz, DMF-d ₇ ) δppm: 7.50-7.10 (3H, m), 6.94 (1H, s), 4.98 (1H br.s), 1.37 (9H, s), 1.28 (9H, s ).
Melting point (° C): 249-258.

(Example 216)
6-Chloro-3- (2-cyclopropyl-5-fluorophenoxy) -4-pyridazinol (Compound No. 658)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.10-6.85 (3H, m), 6.72 (1H, s), 1.92-1.75 (1H, m), 0.85-0.70 (2H, m), 0.70-0.54 (2H, m).
Melting point (° C): 227-228.

(Example 217)
6-Chloro-3- (5-chloro-2-cyclopropylphenoxy) -4-pyridazinol (Compound No. 659)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.19 (1H, d, J = 7.7 Hz), 7.16 (1H, s), 7.01 (1H, d, J = 7.7 Hz), 6.72 (1H, s) , 1.94-1.79 (1H, m), 0.90-0.75 (2H, m), 0.75-0.58 (2H, m).
Melting point (° C): 194-195.

(Example 218)
6-Chloro-3- (2-cyclopropyl-5-methylphenoxy) -4-pyridazinol (Compound No. 662)
¹ H-NMR (200MHz, CD ₃ OD) δppm: 6.96 (1H, d, J = 7.7Hz), 6.89 (1H, s), 6.87 (1H, d, J = 7.7Hz), 6.68 (1H, s) , 2.28 (3H, s), 1.87-1.73 (1H, m), 0.80-0.51 (4H, m).
Melting point (° C): 150-159.

(Example 219)
6-Chloro-3- (2-cyclopropyl-5-ethylphenoxy) -4-pyridazinol (Compound No. 663)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.01 (1H, d, J = 8.0 Hz), 6.92 (1H, s), 6.92 (1H, d, J = 8.0 Hz), 6.69 (1H, s) , 2.61 (2H, t, J = 7.7Hz), 1.88-1.72 (1H, m), 1.20 (3H, q, J = 7.7Hz), 0.82-0.66 (2H, m), 0.65-0.52 (2H, m ).
Physical properties: amorphous.

(Example 220)
6-Chloro-3- (2-cyclopropyl-5-isopropylphenoxy) -4-pyridazinol (Compound No. 664)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.05 (1H, dd, J = 7.7, 1.8 Hz), 7.00 (1H, br.s), 6.93 (1H, d, J = 7.7 Hz), 6.70 ( 1H, s), 2.87 (1H, septet, J = 7.0Hz), 1.90-1.72 (1H, m), 1.22 (6H, d, J = 7.0Hz), 0.85-0.68 (2H, m), 0.68-0.52 (2H, m).
Melting point (° C): 211-212.

(Example 221)
3-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] -4-cyclopropylbenzonitrile (Compound No. 667)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.58-7.48 (2H, m), 7.15 (1H, d, J = 8.8Hz), 6.74 (1H, s), 2.10-1.90 (1H, m), 1.05-0.93 (2H, m), 0.83-0.70 (2H, m).
Melting point (° C): 211-212.

(Example 222)
6-Chloro-3- [5-fluoro-2- (1-propenyl) phenoxy] -4-pyridazinol (Compound No. 679)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.61-7.53 (1H, m), 7.03-6.90 (2H, m), 6.72 (1H, s), 6.44-6.19 (2H, m), 1.80 (3H , d, J = 5.5Hz).
Melting point (° C): 210-217.

(Example 223)
6-Chloro-3- [5-chloro-2- (1-propenyl) phenoxy] -4-pyridazinol (Compound No. 680)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.55 (1H, d, J = 8.4 Hz), 7.24-7.17 (2H, m), 6.72 (1H, s), 6.46-6.30 (2H, m), 1.81 (3H, d, J = 5.1Hz).
Melting point (° C): 221-224.

(Example 224)
2-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] -4- (dimethylamino) benzaldehyde (Compound No. 692)
¹ H-NMR (90MHz, DMSO-d ₆ ) δppm: 9.78 (1H, s), 7.69 (1H, d, J = 6.0Hz), 6.81 (1H, s), 6.78-6.46 (2H, m), 3.05 (6H, s).
Melting point (° C): 124-127.

(Example 225)
3- (5-Chloro-2-methoxyphenoxy) -6-chloro-4-pyridazinol (Compound No. 701)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.23-7.18 (2H, m), 7.05 (1H, d, J = 8.8 Hz), 6.66 (1H, s), 3.73 (3H, s).
Melting point (° C): 143-155.

(Example 226)
3- (5-Bromo-2-methoxyphenoxy) -6-chloro-4-pyridazinol (Compound No. 702)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.39-7.31 (2H, m), 7.02 (1H, d, J = 8.4 Hz), 6.67 (1H, s), 3.74 (3H, s).
Melting point (° C): 135-137.

(Example 227)
6-Chloro-3- (4-fluoro-2-methylphenoxy) -4-pyridazinol (Compound No. 557)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.14-6.88 (3H, m), 6.71 (1H, s), 2.16 (3H, s).
Melting point (° C): 249-250.

(Example 228)
3-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] -4-methoxybenzonitrile (Compound No. 707)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.66 (1H, dd, J = 8.4, 2.2 Hz), 7.58 (1H, d, J = 2.2 Hz), 7.26 (1H, d, J = 8.4 Hz) , 6.71 (1H, s), 3.85 (3H, s).
Melting point (° C): 187-192.

(Example 229)
6-Chloro-3- (2-methoxy-5-nitrophenoxy) -4-pyridazinol (Compound No. 708)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 8.18 (1H, dd, J = 9.2, 2.6 Hz), 8.04 (1H, d, J = 2.6 Hz), 7.27 (1H, d, J = 9.2 Hz) , 6.59 (1H, s), 3.89 (3H, s).
Physical properties: amorphous.

(Example 230)
6-Chloro-3- (2,5-dimethoxyphenoxy) -4-pyridazinol (Compound No. 709)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.04-6.99 (1H, m), 6.81-6.78 (2H, m), 6.68 (1H, s), 3.76 (3H, s), 3.70 (3H, s ).
Melting point (° C): 150-152.

(Example 231)
6-Chloro-3- (2,6-difluorophenoxy) -4-pyridazinol (Compound No. 710)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.54-7.20 (3H, m), 6.88 (1H, s).
Melting point (° C): 209-213.

(Example 232)
6-Chloro-3- (2-chloro-6-fluorophenoxy) -4-pyridazinol (Compound No. 711)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.35-7.13 (3H, m), 6.61 (1H, s).
Melting point (° C): 235.

(Example 233)
3- (2-Bromo-6-fluorophenoxy) -6-chloro-4-pyridazinol (Compound No. 712)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.31-7.15 (3H, m), 6.65 (1H, s).
Physical properties: amorphous.

(Example 234)
6-Chloro-3- (2-fluoro-6-propylphenoxy) -4-pyridazinol (Compound No. 716)
Melting point (° C): 134-137.

(Example 235)
6-Chloro-3- (2-fluoro-6-isopropylphenoxy) -4-pyridazinol (Compound No. 717)
¹ H-NMR (200MHz, DMSO-d ₆ ) δppm: 7.35-7.15 (3H, m), 6.89 (1H, br.s), 3.02 (1H, septet, J = 7.0Hz), 1.14 (6H, J = 7.0Hz).
Melting point (° C): 215-220.

(Example 236)
6-Chloro-3- (2-cyclopropyl-6-fluorophenoxy) -4-pyridazinol (Compound No. 719)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.22-6.96 (2H, m), 6.81-6.71 (1H, m), 6.72 (1H, s), 2.03-1.89 (1H, m), 0.93-0.80 (2H, m), 0.69-0.62 (2H, m).
Melting point (° C): 200-203.

(Example 237)
6-Chloro-3- {2- [1- (ethylsulfanyl) ethyl] -6-fluorophenoxy} -4-pyridazinol (Compound No. 728)
¹ H-NMR (200MHz, CD ₃ OD) δppm: 7.42 (1H, d, J = 8.1 Hz), 7.26-7.15 (1H, m), 7.07-6.97 (1H, m), 6.46 (1H, s), 4.33 (1H, q, J = 7.0 Hz), 2.42-2.20 (2H, m), 1.43 (3H, d, J = 7.0 Hz), 1.02 (3H, t, J = 7.0 Hz).
Physical properties: amorphous.

(Example 238)
6-Chloro-3- (2-fluoro-6-nitrophenoxy) -4-pyridazinol (Compound No. 731)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 8.03-7.99 (1H, m), 7.78-7.53 (2H, m), 6.89 (1H, s).
Melting point (° C): 210 (sublimation).

(Example 239)
6-Chloro-3- (2-fluoro-6-methoxyphenoxy) -4-pyridazinol (Compound No. 732)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.26 (1H, dd, J = 15.0, 8.1 Hz), 7.02-6.91 (2H, m), 6.84 (1H, s), 3.75 (3H, s) .
Melting point (° C): 190-194 (sublimation).

(Example 240)
6-Chloro-3- (2,6-dichlorophenoxy) -4-pyridazinol (Compound No. 733)
¹ H-NMR (90 MHz, DMSO-d ₆ ) δ ppm: 7.70-7.10 (3H, m), 6.80 (1H, s).
Melting point (° C): 265.

(Example 241)
6-Chloro-3- (2-chloro-6-iodophenoxy) -4-pyridazinol (Compound No. 735)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.90 (1H, d, J = 8.1 Hz), 7.64 (1H, d, J = 8.1 Hz), 7.12 (1H, t, J = 8.1 Hz), 7.02-6.80 (1H, br.m).
Melting point (° C): 262-264.

(Example 242)
6-Chloro-3- (2-chloro-6-methylphenoxy) -4-pyridazinol (Compound No. 736)
¹ H-NMR (90 MHz, CD ₃ OD) δ ppm: 7.50-7.00 (3H, m), 6.75 (1H, s), 2.22 (3H, s).
Melting point (° C): 235.

(Example 243)
6-Chloro-3- (2-chloro-6-ethylphenoxy) -4-pyridazinol (Compound No. 737)
Melting point (° C): 194-195.

(Example 244)
6-Chloro-3- (5-fluoro-2-methoxyphenoxy) -4-pyridazinol (Compound No. 700)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.13-6.94 (3H, m), 6.71 (1H, s), 3.74 (1H, s).
Melting point (° C): 187-191.

(Example 245)
6-Chloro-3- (2-chloro-6-cyclopropylphenoxy) -4-pyridazinol (Compound No. 740)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.30 (1H, dd, J = 8.1, 1.5 Hz), 7.17 (1H, dd, J = 8.1, 7.7 Hz), 6.96 (1H, dd, J = 7.7 1.5Hz), 6.76 (1H, s), 2.00-1.84 (1H, m), 0.95-0.80 (2H, m), 0.70-0.60 (2H, m).
Melting point (° C): 224-225.

(Example 246)
6-Chloro-3- [2-chloro-6- (2-methyl-2-propenyl) phenoxy] -4-pyridazinol (Compound No. 746)
Melting point (° C): 198-200.

(Example 247)
6-Chloro-3- (2-chloro-6-nitrophenoxy) -4-pyridazinol (Compound No. 754)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 8.12 (1H, dd, J = 8.1, 1.5 Hz), 7.95 (1H, dd, J = 8.1, 1.5 Hz), 7.59 (1H, t, J = 8.1 Hz), 6.76 (1H, s).
Physical properties: amorphous.

(Example 248)
6-Chloro-3- (2,6-dibromophenoxy) -4-pyridazinol (Compound No. 756)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.65 (2H, d, J = 8.1 Hz), 7.11 (1H, t, J = 8.1 Hz), 6.74 (1H, br.s).
Melting point (° C): 274-278.

(Example 249)
3- (2-Bromo-6-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 758)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.56 (1H, br.d, J = 7.7 Hz), 7.36 (1H, br.d, J = 7.7 Hz), 7.16 (1H, t, J = 7.7Hz), 6.92 (1H, br.s), 2.14 (3H, s).
Melting point (° C): 242-243.

(Example 250)
3- (2-Bromo-6-ethylphenoxy) -6-chloro-4-pyridazinol (Compound No. 759)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.49 (1H, dd, J = 7.9, 1.6 Hz), 7.32 (1H, dd, J = 7.9, 1.6 Hz), 7.14 (1H, t, J = 7.9 Hz), 6.75 (1H, s), 2.58 (2H, q, J = 7.5Hz), 1.18 (3H, t, J = 7.5Hz).
Melting point (° C): 215-217.

(Example 251)
3-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] -4-methoxybenzonitrile (Compound No. 707)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.66 (1H, dd, J = 8.4, 2.2 Hz), 7.58 (1H, d, J = 2.2 Hz), 7.26 (1H, d, J = 8.4 Hz) , 6.71 (1H, s), 3.85 (3H, s).
Melting point (° C): 187-192.

(Example 252)
3- (2-Bromo-6-chlorophenoxy) -6-chloro-4-pyridazinol (Compound No. 734)
¹ H-NMR (200MHz, CD ₃ OD) δppm: 7.64 (1H, dd, J = 1.5Hz, 8.1Hz), 7.52 (1H, dd, J = 1.5Hz, 8.0Hz), 7.21 (1H, t, J = 8.1Hz), 6.76 (1H, s).
Melting point (° C): 266-274.

(Example 253)
3- (2-Bromo-6-cyclopropylphenoxy) -6-chloro-4-pyridazinol (Compound No. 762)
¹ H-NMR (200MHz, DMSO-d ₆ ) δppm: 7.51 (1H, d, J = 7.8Hz), 7.14 (1H, t, J = 7.8Hz), 7.02 (1H, d, J = 7.8Hz), 6.89 (1H, s), 1,89-1.75 (1H, m), 0.88-0.75 (2H, m), 0.75-0.58 (2H, m).
Melting point (° C): 230-232.

(Example 254)
3-Bromo-2-[(6-chloro-4-hydroxy-3-pyridazinyl) oxy] benzonitrile (Compound No. 775)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 8.00 (1H, dd, J = 8.1, 1.5 Hz), 7.82 (1H, dd, J = 8.1, 1.5 Hz), 7.37 (1H, t, J = 8.1 Hz), 6.75 (1H, s).
Melting point (° C): 188 (dec.).

(Example 255)
3- (2-Bromo-6-methoxyphenoxy) -6-chloro-4-pyridazinol (Compound No. 778)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.26-7.05 (3H, m), 6.70 (1H, s), 3.78 (3H, s).
Melting point (° C): 220-221.

(Example 256)
6-Chloro-3- (2-iodo-6-methylphenoxy) -4-pyridazinol (Compound No. 780)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.70 (1H, d, J = 7.7 Hz), 7.29 (1H, d, J = 8.1 Hz), 6.95 (1H, t, J = 7.7 Hz), 6.76 (1H, s), 2.20 (3H, s).
Melting point (° C): 250-252.

(Example 257)
6-Chloro-3- (2-ethyl-6-iodophenoxy) -4-pyridazinol (Compound No. 781)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.72 (1H, dd, J = 7.7, 1.5 Hz), 7.33 (1H, dd, J = 7.7, 1.5 Hz), 7.00 (1H, t, J = 7.7 Hz), 6.76 (1H, s), 2.57 (2H, q, J = 7.7Hz), 1.17 (3H, t, J = 7.7Hz).
Melting point (° C): 242-244.

(Example 258)
6-Chloro-3- (2-iodo-6-isopropylphenoxy) -4-pyridazinol (Compound No. 782)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.70 (1H, dd, J = 8.0, 1.5 Hz), 7.40 (1H, dd, J = 8.0, 1.5 Hz), 7.03 (1H, t, J = 8.0 Hz), 6.76 (1H, s), 3.01 (1H, septet, J = 7.0Hz), 1.18 (6H, d, J = 7.0Hz).
Melting point (° C): 250-255.

(Example 259)
3-Bromo-2-[(6-chloro-4-hydroxy-3-pyridazinyl) oxy] benzonitrile (Compound No. 775)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 8.00 (1H, dd, J = 8.1, 1.5 Hz), 7.82 (1H, dd, J = 8.1, 1.5 Hz), 7.37 (1H, t, J = 8.1 Hz), 6.75 (1H, s).
Melting point (° C): 188 (dec.).

(Example 260)
6-Chloro-3- (2-ethyl-6-methylphenoxy) -4-pyridazinol (Compound No. 802)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.12-6.97 (3H, m), 6.52 (1H, s), 2.37 (2H, q, J = 7.6Hz), 1.95 (3H, s), 1.04 (3H , t, J = 7.6Hz).
Physical properties: amorphous.

(Example 261)
6-Chloro-3- (2-isopropyl-6-methylphenoxy) -4-pyridazinol (Compound No. 803)
¹ H-NMR (200MHz, CD ₃ OD) δppm: 7.23-7.06 (3H, m), 6.72 (1H, s), 2.96 (1H, septet, J = 7.0Hz), 2.10 (3H, s), 1.16 ( 6H, d, J = 7.0Hz).
Melting point (° C): 215-220.

(Example 262)
3- (2-sec-Butyl-6-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 804)
Melting point (° C): 187-189.

(Example 263)
6-Chloro-3- [2- (2,2-dichlorocyclopropyl) -6-methylphenoxy] -4-pyridazinol (Compound No. 827)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.25 (1H, br.d, J = 6.2 Hz), 7.16 (1H, dd, J = 7.7, 7.3 Hz), 6.98 (1H, br.d, J = 7.7Hz), 6.72 (1H, s), 2.85 (1H, dd, J = 11.0, 10.6Hz), 2.22 (3H, s).
Melting point (° C): 213-215.

(Example 264)
6-Chloro-3- (2-methyl-6-vinylphenoxy) -4-pyridazinol (Compound No. 834)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.46 (1H, dd, J = 6.6, 2.6 Hz), 7.25-7.05 (2H, m), 6.71 (1H, dd, J = 17.6, 11.4 Hz), 6.70 (1H, s), 5.74 (1H, dd, J = 17.6, 1.5Hz), 5.21 (1H, dd, J = 11.4, 1.5Hz), 2.11 (3H, s).
Physical properties: amorphous.

(Example 265)
6-Chloro-3- (6-cyclopropyl-3-fluoro-2-methylphenoxy) -4-pyridazinol (Compound No. 1052)
¹ H-NMR (200MHz, CD ₃ OD) δppm: 6.92-6.70 (3H, m), 2.06 (3H, d, J = 2.2Hz), 1.85-1.70 (1H, m), 0.79-0.45 (4H, m ).
Melting point (° C): 230-231.

(Example 266)
6-Chloro-3- (2-methyl-6-nitrophenoxy) -4-pyridazinol (Compound No. 844)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.95 (1H, d, J = 8.1 Hz), 7.76 (1H, d, J = 7.7 Hz), 7.45 (1H, dd, J = 8.1, 7.7 Hz) ), 6.80 (1H, s), 2.20 (3H, s).
Physical properties: Pasty.

(Example 267)
6-Chloro-3- (2-methoxy-6-methylphenoxy) -4-pyridazinol (Compound No. 845)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.10-7.01 (1H, m), 6.79-6.72 (2H, m), 6.55 (1H, s), 3.64 (3H, s), 2.08 (3H, s) .
Physical properties: amorphous.

(Example 268)
6-Chloro-3- (2,6-diethylphenoxy) -4-pyridazinol (Compound No. 846)
¹ H-NMR (60MHz, CDCl ₃ ) δppm: 10.21 (1H, br.s), 7.02 (3H, br.s), 6.47 (1H, s), 2.27 (4H, q, J = 7.6Hz), 0.98 (6H, t, J = 7.6Hz).
Melting point (° C): 181-185.

(Example 269)
6-Chloro-3- (2-cyclopropyl-6-ethylphenoxy) -4-pyridazinol (Compound No. 850)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.11 (2H, d, J = 4.8 Hz), 6.85 (1H, t, J = 4.8 Hz), 6.71 (1H, s), 2.52 (2H, q, J = 7.5Hz), 1.87-1.72 (1H, m), 1.16 (3H, t, J = 7.5Hz), 0.80-0.65 (2H, m), 0.65-0.50 (2H, m).
Physical properties: amorphous.

(Example 270)
6-Chloro-3- (2,6-dipropylphenoxy) -4-pyridazinol (Compound No. 890)
Melting point (° C): 191-193.

(Example 271)
6-Chloro-3- (2,6-diisopropylphenoxy) -4-pyridazinol (Compound No. 894)
¹ H-NMR (90MHz, DMSO-d ₆ ) δppm: 7.28 (3H, s), 6.80 (1H, s), 2.88 (2H, septet, J = 7.0Hz), 1.15 (12H, d, J = 7.0Hz ).
Melting point (° C):> 285.

(Example 272)
6-Chloro-3- (2-cyclopropyl-6-isopropylphenoxy) -4-pyridazinol (Compound No. 896)
¹ H-NMR (200MHz, DMSO-d ₆ ) δppm: 7.22-7.12 (2H, m), 6.83 (1H, br.s), 6.82 (1H, dd, J = 6.6, 2.2Hz), 2.91 (1H, septet, J = 7.0Hz), 1.74-1.63 (1H, m), 1.11 (6H, d, J = 7.0Hz), 0.75-0.71 (2H, m), 0.58-0.50 (2H, m).
Melting point (° C): 242-245.

(Example 273)
6-Chloro-3- (2-isopropyl-6-nitrophenoxy) -4-pyridazinol (Compound No. 911)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 8.00 (1H, d, J = 7.7 Hz), 7.88 (1H, d, J = 7.7 Hz), 7.54 (1H, t, J = 7.7 Hz), 6.96 (1H, br.s), 3.07 (1H, septet, J = 7.0Hz), 1.16 (6H, d, J = 7.0Hz).
Melting point (° C): 205-209.

(Example 274)
3- (2-tert-Butyl-6-cyclopropylphenoxy) -6-chloro-4-pyridazinol (Compound No. 914)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.28 (1H, br.d, J = 8.1 Hz), 7.10 (1H, dd, J = 8.1 and 7.7 Hz), 6.90 (1H, d, J = 7.7 Hz), 6.70 (1H, s), 1.80-1.55 (1H, m), 1.34 (9H, s), 0.85-0.60 (2H, m), 0.50-0.20 (2H, m).
Melting point (° C): 230-231.

(Example 275)
6-Chloro-3- (2,6-dicyclopropylphenoxy) -4-pyridazinol (Compound No. 931)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.08 (1H, t, J = 7.7 Hz), 6.81 (2H, d, J = 7.7 Hz), 6.71 (1H, s), 1.95-1.75 (2H, m), 0.85-0.70 (4H, m), 0.70-0.50 (4H, m).
Melting point (° C): 232-234.

(Example 276)
6-Chloro-3- (2-cyclopropyl-6-methoxyphenoxy) -4-pyridazinol (Compound No. 964)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.13 (1H, t, J = 8.1 Hz), 6.92 (1H, d, J = 8.1 Hz), 6.81 (1H, br.s), 6.54 (1H , d, J = 8.1Hz), 3.68 (3H, s), 1.87-1.78 (1H, m), 0.87-0.78 (2H, m), 0.64-0.56 (2H, m).
Melting point (° C): 194-199.

(Example 277)
6-Chloro-3- (2-cyclopropyl-6-ethoxyphenoxy) -4-pyridazinol (Compound No. 965)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.07 (1H, t, J = 8.1 Hz), 6.84 (1H, dd, J = 8.4, 1.5 Hz), 6.71 (1H, s), 6.54 (1H, dd, J = 8.4, 1.5Hz), 3.97 (2H, q, J = 7.0Hz), 2.04-1.91 (1H, m), 1.18 (3H, t, J = 7.0Hz), 0.89-0.79 (2H, m ), 0.66-0.60 (2H, m).
Melting point (° C): 174-179.

(Example 278)
6-Chloro-3- {2,6-di [(1E) -1-propenyl] phenoxy} -4-pyridazinol (Compound No. 979)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.40 (2H, d, J = 7.8 Hz), 7.15 (1H, t, J = 7.8 Hz), 6.72 (1H, s), 6.34 (2H, d, J = 16.4Hz), 6.27 (2H, dd, J = 16.4, 4.9Hz), 1.79 (6H, d, J = 4.9Hz).
Melting point (° C): 163-164.

(Example 279)
6-Chloro-3- (2,6-diallylphenoxy) -4-pyridazinol (Compound No. 982)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.20-7.15 (3H, m), 6.70 (1H, s), 5.95-5.75 (2H, m), 5.02-4.87 (4H, m), 3.26 (4H , d, J = 6.8Hz).
Melting point (° C): 131-135.

(Example 280)
6-Chloro-3- (2,6-dimethoxyphenoxy) -4-pyridazinol (Compound No. 987)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 7.19 (1H t, J = 8.3 Hz), 6.79-6.75 (3H m), 3.71 (6H, s).
Melting point (° C): 199-201.

(Example 281)
6-Chloro-3- (3,5-dimethylphenoxy) -4-pyridazinol (Compound No. 998)
¹ H-NMR (60 MHz, DMSO-d ₆ ) δ ppm: 6.90-6.65 (4H, m), 2.27 (6H, s).
Melting point (° C): 178-182.

(Example 282)
6-Chloro-3- (3-isopropyl-5-methylphenoxy) -4-pyridazinol (Compound No. 1000)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 6.94 (1H, s), 6.84 (1H, s), 6.81 (1H, s), 6.69 (1H, s), 2.87 (1H, septet, J = 7.0 Hz), 2.32 (3H, s), 1.23 (6H, d, J = 7.0 Hz).
Melting point (° C): 204-206.

(Example 283)
6-Chloro-3- (3,5-diisopropylphenoxy) -4-pyridazinol (Compound No. 1007)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 6.98 (1H, s), 6.87 (1H, s), 6.86 (1H, s), 6.68 (1H, s), 2.90 (2H, septet, J = 7.0 Hz), 1.24 (12H, d, J = 7.0Hz).
Melting point (° C): 249-253.

(Example 284)
3- [3,5-Bis (trifluoromethyl) phenoxy] -6-chloro-4-pyridazinol (Compound No. 1009)
¹ H-NMR (200 MHz, DMF-d ₇ ) δ ppm: 8.20-7.80 (3H, m), 6.94 (1H, s), 5.50-4.50 (1H, br.s).
Melting point (° C): 237-242.

(Example 285)
3- (2-Bromo-3,5-dimethylphenoxy) -6-chloro-4-pyridazinol (Compound No. 1013)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.11 (1H, s), 7.00 (1H, s), 6.86 (1H, br.s), 2.37 (3H, s), 2.27 (3H, s) .
Melting point (° C): 240-244.

(Example 286)
6-Chloro-3- (2,3,5-trimethylphenoxy) -4-pyridazinol (Compound No. 1016)
¹ H-NMR (90 MHz, CD ₃ OD) δ ppm: 6.90 (1H, s), 6.75 (1H, s), 6.70 (1H, s), 2.30 (6H, s), 2.02 (3H, s).
Melting point (° C): 223-224.

(Example 287)
6-Chloro-3- (3,5-dimethyl-2-propylphenoxy) -4-pyridazinol (Compound No. 1020)
¹ H-NMR (90 MHz, DMSO-d ₆ ) δppm: 6.90 (1H, s), 6.81 (1H, s), 6.77 (1H, s), 2.29 (3H, s), 2.21 (3H, s), 2.53 -2.19 (2H, m), 1.57-1.29 (2H, m), 0.86 (3H, t, J = 6.6Hz).
Melting point (° C): 154.5.

(Example 288)
6-Chloro-3- (2-cyclopropyl-3,5-dimethylphenoxy) -4-pyridazinol (Compound No. 1023)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 6.89 (1H, s), 6.73 (1H, s), 6.69 (1H, s), 2.39 (3H, s), 2.26 (3H, s), 1.45- 1.28 (1H, m), 0.78-0.67 (2H, m), 0.65-0.51 (2H, m).
Melting point (° C): 200-203.

Example 289
6-Chloro-3- [3,5-dimethyl-2- (methylsulfanyl) phenoxy] -4-pyridazinol (Compound No. 1027)
Melting point (° C): 213-214.

(Example 290)
3- (2-Bromo-3,6-dimethylphenoxy) -6-chloro-4-pyridazinol (Compound No. 1040)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.16 (1H, d, J = 7.9 Hz), 7.10 (1H, d, J = 7.9 Hz), 6.72 (1H, s), 2.38 (3H, s) , 2.16 (3H, s).
Melting point (° C): 255-257.

(Example 291)
3- (6-Bromo-3-fluoro-2-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 1050)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.51 (1H, dd, J = 8.8, 5.9 Hz), 7.00 (1H, t, J = 8.8 Hz), 6.96 (1H, s), 2.13 (3H, d, J = 2.2Hz).
Physical properties: amorphous.

(Example 292)
3- (6-Bromo-3-chloro-2-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 1053)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.47 (1H, d, J = 8.1 Hz), 7.23 (1H, d, J = 8.1 Hz), 6.64 (1H, s), 2.24 (3H, s) .
Melting point (° C): 254-260.

(Example 293)
6-Chloro-3- (3-chloro-6-cyclopropyl-2-methylphenoxy) -4-pyridazinol (Compound No. 1055)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.18 (1H, d, J = 8.4 Hz), 6.81 (1H, d, J = 8.4 Hz), 6.64 (1H, s), 2.17 (3H, s) , 1.89-1.76 (1H, m), 0.80-0.71 (2H, m), 0.68-0.51 (2H, m).
Melting point (° C): 233.

(Example 294)
3- (6-Bromo-2,3-dimethylphenoxy) -6-chloro-4-pyridazinol (Compound No. 1058)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.34 (1H, d, J = 8.1 Hz), 6.99 (1H, d, J = 8.1 Hz), 6.71 (1H, s), 2.28 (3H, s) , 2.12 (3H, s).
Melting point (° C): 263-268.

(Example 295)
6-Chloro-3- (2,3,6-trimethylphenoxy) -4-pyridazinol (Compound No. 1060)
¹ H-NMR (90 MHz, CD ₃ OD) δ ppm: 7.00 (2H, s), 6.73 (1H, s), 2.27 (3H, s), 2.07 (3H, s), 2.03 (3H, s).
Melting point (° C): 228.

(Example 296)
6-Chloro-3- (6-cyclopropyl-2,3-dimethylphenoxy) -4-pyridazinol (Compound No. 1061)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 6.96 (1H, d, J = 8.1 Hz), 6.72 (1H, d, J = 8.1 Hz), 6.69 (1H, s), 2.24 (3H, s) , 2.04 (3H, s), 1.85-1.70 (1H, m), 0.75-0.46 (4H, m).
Melting point (° C): 229-234.

(Example 297)
2-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] -3,4-dimethylbenzaldehyde O-methyloxime (Compound No. 1063)
^{1 H-NMR (200MHz, CD} 3 OD) δppm: 7.98 (1H, s), 7.50 (1H, d, J = 8.1Hz), 7.11 (1H, d, J = 8.1Hz), 6.69 (1H, s) , 3.81 (3H, s), 2.32 (3H, s), 2.06 (3H, s).
Physical properties: amorphous.

(Example 298)
6-Chloro-3- (6-methoxy-2,3-dimethylphenoxy) -4-pyridazinol (Compound No. 1064)
¹ H-NMR (200MHz, CD ₃ OD) δppm: 7.00 (1H, d, J = 8.4Hz), 6.78 (1H, d, J = 8.4Hz), 6.66 (1H, s), 3.69 (3H, s) , 2.23 (3H, s), 2.08 (3H, s).
Physical properties: amorphous.

(Example 299)
3- (6-Bromo-3-methoxy-2-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 1066)
¹ H-NMR (200MHz, CD ₃ OD) δppm: 7.42 (1H, d, J = 9.2Hz), 6.82 (1H, d, J = 9.2Hz), 6.69 (1H, s), 3.86 (3H, s) , 2.05 (3H, s).
Melting point (° C): 246-253.

(Example 300)
6-Chloro-3- (6-cyclopropyl-3-methoxy-2-methylphenoxy) -4-pyridazinol (Compound No. 1069)
¹ H-NMR (200MHz, CD ₃ OD) δppm: 6.83 (1H, d, J = 8.8Hz), 6.75 (1H, d, J = 8.8Hz), 6.66 (1H, s), 3.81 (3H, s) , 1.99 (3H, s), 1.78-1.70 (1H, m), 0.69-0.63 (2H, m), 0.52-0.47 (2H, m).
Melting point (° C): 250-253.

(Example 301)
6-Chloro-3- (2-cyclopropyl-3,6-dimethylphenoxy) -4-pyridazinol (Compound No. 1073)
¹ H-NMR (200MHz, CD ₃ OD) δppm: 7.20 (1H, d, J = 7.6Hz), 6.95 (1H, d, J = 7.6Hz), 6.68 (1H, s), 2.39 (3H, s) , 2.10 (3H, s), 1.50-1.25 (1H, m), 0.90-0.70 (2H, m), 0.70-0.50 (2H, m).
Melting point (° C): 171-175.

(Example 302)
3- (2-Allyl-6-ethyl-3-methoxyphenoxy) -6-chloro-4-pyridazinol (Compound No. 1080)
¹ H-NMR (60MHz, DMF-d ₇ ) δppm: 7.11 (1H, d, J = 8.4Hz), 6.85 (1H, s), 6.83 (1H, d, J = 8.4Hz), 6.10-5.30 (1H , m), 5.00-4.60 (2H, m), 3.83 (3H, s), 3.30-3.10 (2H, m), 2.40 (2H, q, J = 7.6Hz), 1.10 (3H, t, J = 7.6 Hz).
Melting point (° C): 183-186.

Example 303
6-chloro-3- {3,6-dimethyl-2-[(methylsulfanyl) methyl] phenoxy} -4-pyridazinol (Compound No. 1083)
^{1 H-NMR (90MHz, CD} 3 OD) δppm: 7.21-6.90 (2H, m), 6.71 (1H, s), 3.68 (2H, s), 2.38 (3H, s), 2.09 (3H, s), 2.00 (3H, s).
Physical properties: amorphous.

(Example 304)
3-[(5-Bromo-2,3-dihydro-1H-inden-4-yl) oxy] -6-chloro-4-pyridazinol (Compound No. 1086)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.39 (1H, d, J = 8.1 Hz), 7.05 (1H, d, J = 8.1 Hz), 6.71 (1H, s), 2.94 (2H, t, J = 7.3Hz), 2.79 (2H, t, J = 7.3Hz), 2.10-2.00 (2H, m).
Physical properties: amorphous.

(Example 305)
6-Chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinol (Compound No. 1088)
^{1 H-NMR (200MHz, DMSO} -d 6) δppm: 7.11-7.01 (2H, m), 6.83 (1H, br.s), 2.88 (2H, t, J = 7.3Hz), 2.59 (2H, t, J = 7.3Hz), 2.06 (3H, s), 2.06-1.91 (2H, m).
Melting point (° C): 222-225.

(Example 306)
6-Chloro-3-[(5-ethyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinol (Compound No. 1089)
¹ H-NMR (200MHz, CD ₃ OD) δppm: 7.06 (2H, s), 6.71 (1H, s), 2.91 (2H, t, J = 7.3Hz), 2.67 (2H, t, J = 7.3Hz) , 2.51 (2H, q, J = 7.7Hz), 2.04 (2H, quintet, J = 7.3Hz), 1.13 (3H, t, J = 7.7Hz).
Melting point (° C): 193-196.

(Example 307)
6-Chloro-3-[(5-cyclopropyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinol (Compound No. 1091)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.02 (1H, d, J = 7.7 Hz), 6.79 (1H, d, J = 7.7 Hz), 6.71 (1H, s), 2.90 (2H, t, J = 7.3Hz), 2.72 (2H, t, J = 7.3Hz), 2.18-1.98 (2H, m), 1.92-1.75 (1H, m), 0.82-0.70 (2H, m), 0.60-0.47 (2H , m).
Melting point (° C): 218-220.

(Example 308)
6-Chloro-3-[(6-methyl-2,3-dihydro-1-benzofuran-7-yl) oxy] -4-pyridazinol (Compound No. 1096)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 6.99 (1H, d, J = 7.7 Hz), 6.72 (1H, d, J = 7.7 Hz), 6.70 (1H, s), 4.53 (2H, t, J = 8.8Hz), 3.20 (2H, br.t, J = 8.8Hz), 2.15 (3H, s).
Melting point (° C): 217-219.

(Example 309)
3-[(6-Bromo-1-benzofuran-7-yl) oxy] -6-chloro-4-pyridazinol (Compound No. 1099)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.75 (1H, d, J = 2.2 Hz), 7.48 (1H, d, J = 8.4 Hz), 7.47 (1H, d, J = 8.4 Hz), 6.92 (1H, d, J = 2.2Hz), 6.78 (1H, s).
Physical properties: amorphous.

(Example 310)
6-Chloro-3-[(6-methyl-1-benzofuran-7-yl) oxy] -4-pyridazinol (Compound No. 1100)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.65 (1H, d, J = 2.2 Hz), 7.40 (1H, d, J = 8.1 Hz), 7.14 (1H, d, J = 8.1 Hz), 6.82 (1H, d, J = 2.2Hz), 6.75 (1H, s), 2.31 (3H, s).
Physical property: Oily substance.

(Example 311)
6-Chloro-3-[(6-cyclopropyl-1-benzofuran-7-yl) oxy] -4-pyridazinol (Compound No. 1102)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.65 (1H, d, J = 2.2 Hz), 7.40 (1H, d, J = 8.1 Hz), 6.87 (1H, d, J = 8.1 Hz), 6.81 (1H, d, J = 2.2Hz), 6.75 (1H, s), 2.10-1.98 (1H, m), 0.98-0.80 (2H, m), 0.80-0.64 (2H, m).
Melting point (° C): 175-180.

(Example 312)
6-Chloro-3-[(5-methyl-1-benzofuran-4-yl) oxy] -4-pyridazinol (Compound No. 1109)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.65 (1H, d, J = 2.2 Hz), 7.32 (1H, d, J = 8.4 Hz), 7.18 (1H, d, J = 8.4 Hz), 6.73 (1H, s), 6.60 (1H, d, J = 2.2Hz), 2.23 (3H, s).
Melting point (° C): 222-225.

(Example 313)
6-Chloro-3- (2,4-dicyclopropyl-6-fluorophenoxy) -4-pyridazinol (Compound No. 1115)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 6.71-6.65 (2H, m), 6.54 (1H, s), 2.02-1.81 (2H, m), 1.01-0.72 (4H, m), 0.68-0.60 (4H, m).
Physical properties: amorphous.

(Example 314)
6-Chloro-3- (2,4-dibromo-3,6-dimethylphenoxy) -4-pyridazinol (Compound No. 1118)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.54 (1H, s), 6..71 (1H, s), 2.56 (3H, s), 2.16 (3H, s).
Melting point (° C): 241-248.

(Example 315)
3- (2-Bromo-4,6-dimethylphenoxy) -6-chloro-4-pyridazinol (Compound No. 1119)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.31 (1H, br.s), 7.10 (1H, br.s), 6.74 (1H, s), 2.31 (3H, s), 2.17 (3H, s ).
Melting point (° C): 254-256.

(Example 316)
6-Chloro-3- (2-ethyl-4,6-diiodophenoxy) -4-pyridazinol (Compound No. 1120)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 8.03 (1H, d, J = 2.2 Hz), 7.66 (1H, d, J = 2.2 Hz), 6.74 (1H, s), 2.52 (2H, q, J = 7.7Hz), 1.17 (3H, t, J = 7.7Hz).
Melting point (° C): 142-144.

(Example 317)
6-Chloro-3- (2,4,6-trimethylphenoxy) -4-pyridazinol (Compound No. 1122)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 6.90 (2H, s), 6.71 (1H, s), 2.27 (3H, s), 2.07 (6H, s).
Melting point (° C): 235-239.

(Example 318)
6-Chloro-3- (2-cyclopropyl-4,6-dimethylphenoxy) -4-pyridazinol (Compound No. 1123)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 6.88 (1H, br.s), 6.69 (1H, s), 6.63 (1H, br.s), 2.26 (3H, s), 2.09 (3H, s ), 1.85-1.70 (1H, m), 0.80-0.65 (2H, m), 0.65-0.50 (2H, m).
Melting point (° C): 215-217.

(Example 319)
3- (2-Bromo-3,5,6-trimethylphenoxy) -6-chloro-4-pyridazinol (Compound No. 1124)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.13 (1H, s), 6.88 (1H, br.s), 2.32 (3H, s), 2.23 (3H, s), 2.01 (3H, s) .
Melting point (° C): 280-290.

(Example 320)
6-Chloro-3- (2,3,5,6-tetramethylphenoxy) -4-pyridazinol (Compound No. 1125)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 6.88 (1H, s), 6.69 (1H, s), 2.22 (6H, s), 1.98 (6H, s).
Melting point (° C): 278-283.

(Example 321)
6-Chloro-3-[(5,6-dimethyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinol (Compound No. 1129)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 6.72 (1H, s), 6.68 (1H, s), 2.88 (2H, t, J = 7.4 Hz), 2.70 (2H, t, J = 7.4 Hz) , 2.24 (3H, s), 2.17 (3H, s), 2.05 (2H, quintet, J = 7.4Hz).
Melting point (° C): 210-213.

(Example 322)
6-Chloro-3- (1,2,3,5,6,7-hexahydro-s-indasen-4-yloxy) -4-pyridazinol (Compound No. 1133)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.95 (1H, s), 6.65 (1H, s), 2.88 (4H, t, J = 7.3 Hz), 2.68 (4H, t, J = 7.3 Hz) , 2.20-1.90 (4H, m).
Physical properties: amorphous.

(Example 323)
6-Chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl acetate (Compound No. 1140)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.40 (1H, s), 7.26-6.98 (4H, m), 2.40 (3H, s), 1.93-1.76 (1H, m), 0.85-0.59 (4H, m).
Physical properties: amorphous.

(Example 324)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl acetate (Compound No. 1151)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.39 (1H, s), 7.15-7.00 (2H, m), 6.90-6.75 (1H, m), 2.42 (3H, s), 2.12 (3H, s) , 1.90-1.67 (1H, m), 0.85-0.50 (4H, m).
Melting point (° C): 98-101.

(Example 325)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl pivalate (Compound No. 1207)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.38 (1H, s), 7.15-7.05 (2H, m), 6.90-6.84 (1H, m), 2.13 (3H, s), 1.81-1.65 (1H, m), 1.41 (9H, s), 0.90-0.50 (4H, m).
Melting point (° C): 84-87.

(Example 326)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl decanoate (Compound No. 1251)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.38 (1H, s), 7.15-7.05 (2H, m), 6.93-6.80 (1H, m), 2.67 (2H, t, J = 7.3Hz), 2.12 (3H, s), 1.85-1.65 (3H, m), 1.55-1.10 (12H, m), 0.95-0.80 (3H, m), 0.80-0.65 (2H, m), 0.65-0.52 (2H, m) .
Physical property: Oily substance.

(Example 327)
6-Chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl cyclopropanecarboxylate (Compound No. 1266)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.43 (1H, s), 7.22-6.98 (4H, m), 2.00-1.75 (2H, m), 1.30-1.08 (4H, m), 0.86-0.51 ( 4H, m).
Melting point (° C): 122-125.

(Example 328)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl benzoate (Compound No. 1387)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.23-8.18 (2H, m), 7.75-7.50 (3H, m), 7.60 (1H, s), 7.30-7.08 (4H, m), 2.18 (3H, s).
Physical property: Oily substance.

(Example 329)
6-Chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl benzoate (Compound No. 1391)
^{1 H-NMR (200MHz, CDCl} 3) δppm: 8.20 (2H, d, J = 7.3Hz), 7.74-7.50 (4H, m), 7.26-7.01 (3H, m), 6.98-6.97 (1H, m) , 1.91-1.80 (1H, m), 0.83-0.57 (4H, m).
Physical properties: amorphous.

(Example 330)
6-Chloro-3- [4- (trimethylsilyl) phenoxy] -4-pyridazinyl benzoate (Compound No. 1396)
Melting point (° C): 100-102.

(Example 331)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl benzoate (Compound No. 1417)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.24-8.20 (2H, m), 7.75-7.68 (1H, m), 7.67-7.52 (3H, m), 7.09-7.07 (2H, m), 6.87- 6.82 (1H, m), 2.16 (3H, s), 1.82-1.71 (1H, m), 0.75-0.71 (2H, m), 0.62-0.53 (2H, m).
Physical properties: amorphous.

(Example 332)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl 2-methylbenzoate (Compound No. 1446)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 8.35-8.08 (2H, m), 7.59 (1H, s), 7.68-7.00 (6H, m), 2.70 (3H, s), 2.21 (3H, s) .
Melting point (° C): 91-93.

(Example 333)
6-Chloro-3- (2-isopropylphenoxy) -4-pyridazinyl 2-methylbenzoate (Compound No. 1448)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 8.15-8.00 (2H, m), 7.58 (1H, s), 7.75-6.90 (6H, m), 3.40-2.85 (1H, m), 2.69 (3H, s), 1.15 (6H, d, J = 7.0 Hz).
Refractive index: n _D ²² 1.5709.

(Example 334)
3- (2-sec-Butylphenoxy) -6-chloro-4-pyridazinyl 2-methylbenzoate (Compound No. 1450)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 8.28-8.05 (1H, m), 7.60-7.05 (7H, m), 7.52 (1H, s), 3.05-2.60 (1H, m), 2.65 (3H, s), 1.70-1.00 (2H, m), 1.10 (3H, d, J = 7.0Hz), 0.90-0.50 (3H, m).
Physical properties: Pasty.

(Example 335)
6-Chloro-3- (2-cyclohexylphenoxy) -4-pyridazinyl 2-methylbenzoate (Compound No. 1455)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 8.30-7.00 (8H, m), 7.54 (1H, s), 2.68 (1H, br.s), 2.67 (3H, s), 2.00-1.00 (10H, m).
Melting point (° C): 89-91.

(Example 336)
3-([1,1'-biphenyl] -2-yloxy) -6-chloro-4-pyridazinyl 2-methylbenzoate (Compound No. 1456)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 8.20-7.90 (1H, m), 7.60-7.10 (13H, m), 2.58 (3H, s).
Refractive index: n _D ²⁸ 1.6055.

(Example 337)
3- (3-tert-Butylphenoxy) -6-chloro-4-pyridazinyl 2-methylbenzoate (Compound No. 1457)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 8.28-8.02 (1H, m), 7.55 (1H, s), 7.65-6.85 (7H, m), 2.64 (3H, s), 1.28 (9H, s) .
Melting point (° C): 63-64.

(Example 338)
6-Chloro-3- (3-methoxyphenoxy) -4-pyridazinyl 2-methylbenzoate (Compound No. 1458)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 8.30-8.00 (1H, m), 7.70-7.10 (4H, m), 7.55 (1H, s), 6.90-6.60 (3H, m), 3.74 (3H, s), 2.64 (3H, s).
Melting point (° C): 66-67.

(Example 339)
6-Chloro-3- (2-isopropyl-5-methylphenoxy) -4-pyridazinyl 2-methylbenzoate (Compound No. 1459)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 8.30-8.00 (1H, m), 7.54 (1H, s), 7.50-6.80 (6H, m), 3.30 -2.75 (1H, m), 2.65 (3H, s), 2.28 (3H, s), 1.15 (6H, d, J = 7.00Hz).
Melting point (° C): 95-97.

(Example 340)
6-Chloro-3- (1-naphthyloxy) -4-pyridazinyl 2-methylbenzoate (Compound No. 1461)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 8.20-7.00 (12H, m), 2.65 (3H, s).
Melting point (° C): 133-134.

(Example 341)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl 2-methoxybenzoate (Compound No. 1509)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 8.11-7.89 (2H, m), 7.70-6.80 (6H, m), 7.50 (1H, s), 3.84 (3H, s), 2.10 (3H, s) .
Melting point (° C): 114-116.

(Example 342)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl 4-methylbenzoate (Compound No. 1553)
^{1 H-NMR (60MHz, CDCl} 3) δppm: 8.07 (2H, d, J = 8.0Hz), 7.58 (1H, s), 7.40-7.03 (4H, m), 7.36 (2H, d, J = 8.0Hz ), 2.51 (3H, s), 2.23 (3H, s).
Melting point (° C): 105-108.

(Example 343)
6-Chloro-3- (2-isopropylphenoxy) -4-pyridazinyl 4-methylbenzoate (Compound No. 1554)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 8.28-7.82 (2H, m), 7.61 (1H, s), 7.51-6.90 (6H, m), 3.30-2.80 (1H, m), 2.46 (3H, s), 1.19 (6H, d, J = 7.0 Hz).
Refractive index: n _D ²² 1.5731.

(Example 344)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl 2,4-dichlorobenzoate (Compound No. 1603)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 8.04 (1H, d, J = 8.4 Hz), 7.58 (1H, s), 7.58-6.92 (6H, m), 2.20 (3H, s).
Melting point (° C): 81-82.5.

(Example 345)
6-Chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl methyl carbonate (Compound No. 1658)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.51 (1H, s), 7.23-6.98 (4H, m), 3.99 (3H, s), 1.91-1.82 (1H, m), 0.84-0.61 (4H, m).
Physical properties: amorphous.

(Example 346)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl ethyl carbonate (Compound No. 1706)
¹ H-NMR (60MHz, CDCl ₃ ) δppm: 7.51 (1H, s), 7.38-7.00 (4H, m), 4.40 (2H, q, J = 7.0Hz), 2.20 (3H, s), 1.40 (3H , t, J = 7.0Hz).
Melting point (° C): 73-74.

(Example 347)
6-Chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl ethyl carbonate (Compound No. 1710)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.51 (1H s), 7.26-6.98 (4H, m), 4.40 (2H, q, J = 7.0Hz), 1.90-1.80 (1H, m), 1.41 ( 3H, t, J = 7.0Hz), 0.84-0.60 (4H, m).
Physical properties: amorphous.

(Example 348)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl isobutyl carbonate (Compound No. 1757)
¹ H-NMR (60MHz, CDCl ₃ ) δppm: 7.45 (1H, s), 7.30-7.00 (4H, m), 4.08 (2H, d, J = 5.8Hz), 2.16 (3H, s), 2.20-1.70 (1H, m), 0.96 (6H, d, J = 5.8Hz).
Melting point (° C): 46-47.

(Example 349)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl 2,2,2-trichloroethyl carbonate (Compound No. 1789)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 7.52 (1H, s), 7.28-7.03 (4H, m), 4.94 (2H, s), 2.18 (3H, s).
Physical properties: amorphous.

(Example 350)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl phenyl carbonate (Compound No. 1840)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.58 (1H, s), 7.50-7.20 (5H, m), 7.20-7.05 (2H, m), 6.92-6.82 (1H, m), 2.16 (3H, s), 1.88-1.72 (1H, m), 0.80-0.55 (4H, m).
Physical property: Oily substance.

(Example 351)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl dimethyl carbamate (Compound No. 1877)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 7.55 (1H, s), 7.40-6.92 (4H, m), 3.10 (3H, s), 3.01 (3H, s), 2.19 (3H, s).
Melting point (° C): 107-109.

(Example 352)
6-Chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl dimethyl carbamate (Compound No. 1879)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.22-6.98 (4H, m), 3.13 (3H, s), 3.04 (3H, s), 1.97-1.80 (1H, m) , 0.85-0.63 (4H, m).
Melting point (° C): 137-138.

(Example 353)
6-Chloro-3- [3- (trifluoromethyl) phenoxy] -4-pyridazinyl dimethyl carbamate (Compound No. 1881)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 7.60 (1H, s), 7.65-7.22 (4H, m), 3.11 (3H s), 3.05 (3H s).
Melting point (° C): 92-93.

(Example 354)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl diethylcarbamate (Compound No. 1898)
¹ H-NMR (60MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.40-6.92 (4H, m), 3.41 (4H, q, J = 6.2Hz), 2.20 (3H, s), 1.27 (6H , t, J = 6.2Hz).
Melting point (° C): 74-75.5.

(Example 355)
6-chloro-3- (2-methylphenoxy) -4-pyridazinyl 1-pyrrolidinecarboxylate (Compound No. 1924)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 7.58 (1H, s), 7.42-7.02 (4H, m), 3.67-3.37 (4H, m), 2.19 (3H, s), 2.07-1.72 (4H, m).
Melting point (° C): 126-127.

(Example 356)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl methanesulfonate (Compound No. 1981)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 7.55 (1H, s), 7.33-7.06 (4H, m), 3.43 (3H, s), 2.20 (3H, s).
Physical property: Oily substance.

(Example 357)
6-Chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl methanesulfonate (Compound No. 1985)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.26-7.23 (2H, m), 7.21-7.02 (2H, m), 3.44 (3H, s), 1.89-1.80 (1H, m), 0.86-0.61 (4H, m).
Melting point (° C): 162-172.

(Example 358)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl methanesulfonate (Compound No. 2010)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.56 (1H, s), 7.18-7.09 (2H, m), 6.91-6.86 (1H, m), 3.47 (3H, s), 2.16 (3H, s) , 1.82-1.68 (1H, m), 0.75-0.69 (2H, m), 0.67-0.55 (2H, m).
Physical properties: amorphous.

(Example 359)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl 1-propanesulfonate (Compound No. 2038)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.34-7.05 (4H, m), 3.48 (2H, t, J = 7.7Hz), 2.20 (3H, s), 2.10 (2H , sixtet, J = 7.7Hz), 1.14 (3H, t, J = 7.7Hz).
Melting point (° C): 72-73.

(Example 360)
6-chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl 1-propanesulfonate (Compound No. 2040)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.28-7.15 (2H, m), 7.12-6.99 (2H, m), 3.52-3.45 (2H, m), 2.17-1.98 ( 2H, m), 1.92-1.78 (1H, m), 1.11 (3H, t, J = 7.3Hz), 0.85-0.73 (2H, m), 0.69-0.60 (2H, m).
Physical properties: Pasty.

(Example 361)
6-Chloro-3- (2,3-dihydro-1H-inden-4-yloxy) -4-pyridazinyl 1-propanesulfonate (Compound No. 2042)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.56 (1H, s), 7.26-7.14 (2H, m), 6.94 (1H, dd, J = 7.0, 1.8Hz), 3.50-3.42 (2H, m) , 2.98 (2H, t, J = 7.3Hz), 2.74 (2H, t, J = 7.3Hz), 2.17-1.98 (4H, m), 1.12 (3H, t, J = 7.3Hz).
Physical properties: Pasty.

(Example 362)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -5-iodo-4-pyridazinol (Compound No. 3849)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.08-7.05 (2H, m), 6.84-6.80 (1H, m), 2.14 (3H, s), 1.86-1.75 (1H, m), 0.81-0.65 (2H, m), 0.60-0.52 (2H, m).
Physical properties: amorphous.

(Example 363)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl trifluoromethanesulfonate (Compound No. 2106)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.52 (1H, s), 7.19-7.09 (2H, m), 6.96-6.89 (1H, m), 2.15 (3H, s), 1.81-1.67 (1H, m), 0.73-0.58 (4H, m).
Melting point (° C): 64-67.

(Example 364)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl benzenesulfonate (Compound No. 2147)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 8.10-7.83 (2H, m), 7.80-7.40 (3H, m), 7.59 (1H, s), 7.30-7.00 (3H, m), 6.90-6.60 ( 1H, m).
Melting point (° C): 91.5-92.

(Example 365)
6-Chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl benzenesulfonate (Compound No. 2151)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.02-7.98 (2H, m), 7.78-7.70 (1H, m), 7.62-7.54 (2H, m), 7.58 (1H, s), 7.26-7.09 ( 2H, m), 6.98-6.93 (1H, m), 6.78-6.69 (1H, m), 1.68-1.54 (1H, m), 0.74-0.52 (4H, m).
Physical property: Oily substance.

(Example 366)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl benzenesulfonate (Compound No. 2176)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.07-8.01 (2H, m), 7.80-7.71 (1H, m), 7.65-7.56 (2H, m), 7.60 (1H, s), 7.11-6.99 ( 2H, m), 6.80 (1H, dd, J = 4.4, 2.4Hz), 1.93 (3H, s), 1.61-1.45 (1H, m), 0.65-0.45 (4H, m).
Melting point (° C): 105-106.

(Example 367)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl 4-chlorobenzenesulfonate (Compound No. 2198)
¹ H-NMR (60MHz, CDCl ₃ ) δppm: 7.94 (2H, d, J = 8.4Hz), 7.60 (1H, s), 7.59 (2H, d, J = 8.4Hz), 7.23-7.09 (3H, m ), 6.90-6.60 (1H, m), 2.93 (3H, s).
Melting point (° C): 93-94.

(Example 368)
3- (2-Isopropylphenoxy) -4-pyridazinyl 4-chlorobenzenesulfonate (Compound No. 2199)
¹ H-NMR (60MHz, CDCl ₃ ) δppm: 7.91 (2H, d, J = 8.4Hz), 7.62 (1H, s), 7.55 (2H, d, J = 8.4Hz), 7.50-7.00 (3H, m ), 6.80-6.60 (1H, m), 3.20-2.50 (1H, m), 1.14 (6H, d, J = 7.0Hz).
Refractive index: n _D ²² 1.5315.

(Example 369)
3- (2-tert-Butylphenoxy) -6-chloro-4-pyridazinyl 4-chlorobenzenesulfonate (Compound No. 2200)
^{1 H-NMR (60MHz, CDCl} 3) δppm: 8.05-7.05 (8H, m), 6.70-6.40 (1H, m), 1.26 (9H, s).
Melting point (° C): 83.5-84.5.

(Example 370)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2220)
¹ H-NMR (60MHz, CDCl ₃ ) δppm: 7.83 (2H, d, J = 8.4Hz), 7.47 (2H, d, J = 8.4Hz), 7.32-6.95 (4H, m), 6.85-6.55 (1H m), 2.43 (3H, s), 1.98 (3H, s).
Melting point (° C): 102-104.

(Example 371)
6-Chloro-3- (2-ethylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2221)
Refractive index: n _D ²⁸ 1.5847.

(Example 372)
6-chloro-3- (2-isopropylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2222)
¹ H-NMR (60MHz, CDCl ₃ ) δppm: 8.00-6.50 (8H, m), 7.55 (1H, s), 2.85 (1H, septet, J = 7.0Hz), 2.42 (3H, s), 1.11 (6H , d, J = 7.0 Hz).
Melting point (° C): 99-100.

(Example 373)
3- (2-sec-Butylphenoxy) -6-chloro-4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2223)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 7.98-6.50 (8H, m), 7.52 (1H, s), 2.99-2.31 (1H, m), 2.41 (3H, s), 1.82-0.95 (2H, m), 1.08 (3H, d, J = 7.0 Hz), 0.90-0.35 (3H, m).
Melting point (° C): 65-66.

(Example 374)
3- (2-tert-Butylphenoxy) -6-chloro-4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2224)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 7.98-7.00 (7H, m), 7.61 (1H s), 6.78-6.45 (1H, m), 2.40 (3H, s), 1.29 (9H, s).
Melting point (° C): 98-99.

(Example 375)
5,6-Dichloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol (Compound No. 3837)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.08-7.06 (2H, m), 6.85-6.80 (1H, m), 2,14 (3H, s), 1.87-1.78 (1H, m), 0.81 -0.72 (2H, m), 0.64-0.52 (2H, m).
Physical properties: amorphous.

(Example 376)
6-Chloro-3- (2-cyclohexylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2230)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 8.00-6.50 (8H, m), 7.50 (1H, s), 2.50 (1H, br.s), 2.40 (3H, s), 2.00-0.90 (10H, m).
Melting point (° C): 120-121.

(Example 377)
3-([1,1'-biphenyl] -2-yloxy) -6-chloro-4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2231)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 7.80-6.60 (14H, m), 2.42 (3H, s).
Melting point (° C): 106-108.

(Example 378)
6-Chloro-3- (2-methoxyphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2232)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 8.00-6.70 (8H, m), 7.56 (1H, s), 3.62 (3H, s), 2.44 (3H, s).
Melting point (° C): 153-157.

(Example 379)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl propionate (Compound No. 1160)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.39 (1H, s), 7.14-7.05 (2H, m), 6.89-6.82 (1H, m), 2.72 (2H, q, J = 7.6Hz), 2.12 (3H, s), 1.82-1.68 (1H, m), 1.31 (3H, t, J = 7.6Hz), 0.74-0.53 (4H, m).
Melting point (° C): 75-77.

(Example 380)
6-chloro-3- (3-chlorophenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2234)
Refractive index: n _D ²⁸ 1.5970.

(Example 381)
3- (3-tert-Butylphenoxy) -6-chloro-4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2235)
¹ H-NMR (60MHz, CDCl ₃ ) δppm: 7.73 (2H, d, J = 8.2Hz), 7.49 (1H, s), 7.23 (2H, d, J = 8.2Hz), 7.14 (1H, d, J = 4.0Hz), 6.90-6.45 (3H, m), 2.38 (3H, s), 1.26 (9H, s).
Melting point (° C): 56-57.

(Example 382)
6-Chloro-3- [3- (trifluoromethyl) phenoxy] -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2236)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 7.95-6.93 (9H, m), 2.40 (3H, s).
Refractive index: n _D ^25.5 1.5556.

(Example 383)
6-Chloro-3- (3-cyanophenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2237)
¹ H-NMR (90 MHz, CDCl ₃ ) δ ppm: 7.85 (2H, d, J = 8.0 Hz), 7.70-7.00 (7H, m), 2.49 (3H, s).
Physical properties: Pasty.

(Example 384)
6-Chloro-3- (3-methoxyphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2238)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 7.90-6.30 (8H, m), 7.47 (1H, s), 3.71 (3H, s), 2.40 (3H, s).
Melting point (° C): 89-90.

(Example 385)
6-Chloro-3- (1-naphthyloxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2240)
¹ H-NMR (60 MHz, CDCl ₃ ) δ ppm: 7.90-6.80 (12H, m), 2.38 (3H, s).
Melting point (° C): 92-94.

(Example 386)
3- (2-Bromo-4-tert-butylphenoxy) -6-chloro-4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2245)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 7.89 (2H, d, J = 8.4 Hz), 7.63 (1H, s), 7.62-7.18 (3H, m), 6.84 (2H, d, J = 8.4 Hz) ), 2.43 (3H, s), 1.29 (9H, s).
Melting point (° C): 110-112.

(Example 387)
6-Chloro-3- (4-chloro-2-methylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2246)
^{1 H-NMR (60MHz, CDCl} 3) δppm: 7.95-7.75 (2H, m), 7.60-7.00 (5H, m), 6.80-6.60 (1H, m), 2.46 (3H, s), 2.00 (3H, s).
Melting point (° C): 115-116.

(Example 388)
6-Chloro-3- (2,4-dimethylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2247)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 7.94-7.78 (2H, m), 7.54 (1H, s), 7.41-7.23 (2H, m), 7.02-6.53 (3H, m), 2.46 (3H, s), 2.30 (3H, s), 1.96 (3H, s).
Melting point (° C): 80-81.

(Example 389)
3- (4-Bromo-2-isopropylphenoxy) -6-chloro-4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2248)
¹ H-NMR (60 MHz, CDCl ₃ ) δppm: 7.80 (2H, d, J = 8.4 Hz), 7.51 (1H, s), 7.45-7.10 (3H, m), 6.56 (2H, d, J = 8.4 Hz) ), 2.85 (1H, septet, J = 6.8Hz), 2.43 (3H, s), 1.10 (6H, d, J = 6.8Hz).
Melting point (° C): 119-122.

(Example 390)
6-Chloro-3- (2-isopropyl-5-methylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2249)
^{1 H-NMR (60MHz, CDCl} 3) δppm: 8.00-6.80 (6H, m), 7.56 (1H, s), 6.46 (1H, br.s), 2.95-2.50 (1H, m), 2.44 (3H, s), 2.25 (3H, s), 1.09 (6H, d, J = 7.0 Hz).
Melting point (° C): 90-92.

(Example 391)
6-Chloro-3- (2,6-dimethylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2263)
Melting point (° C): 89-90.

(Example 392)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2265)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.90 (2H, d, J = 8.1Hz), 7.60 (1H, s), 7.38 (2H, d, J = 8.1Hz), 7.11-7.01 (2H, m ), 6.80 (1H, dd, J = 6.6, 2.6Hz), 2.47 (3H, s), 1.93 (3H, s), 1.59-1.46 (1H, m), 0.64-0.45 (4H, m).
Melting point (° C): 85-87.

(Example 393)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl 4-nitrobenzenesulfonate (Compound No. 2287)
¹ H-NMR (60MHz, CDCl ₃ ) δppm: 8.41 (2H, d, J = 8.4Hz), 8.33 (2H, d, J = 8.4Hz), 7.61 (1H, s), 7.30-7.02 (3H, m ), 6.95-6.63 (1H, m), 2.03 (3H, s).
Melting point (° C): 166-169.

(Example 394)
6-Chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl 4-nitrobenzenesulfonate (Compound No. 2289)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.39 (2H, d, J = 8.8Hz), 8.23 (2H, d, J = 8.8Hz), 7.59 (1H, s), 7.20-7.09 (2H, m ), 6.97-6.92 (1H, m), 6.77-6.73 (1H, m), 1.67-1.59 (1H, m), 0.78-0.54 (4H, m).
Melting point (° C): 158.

(Example 395)
6-Chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl dimethylsulfamate (Compound No. 2351)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.60 (1H, s), 7.26-7.01 (4H, m), 3.09 (6H, s), 1.95-1.78 (1H, m), 0.85-0.63 (4H, m).
Physical property: Oily substance.

(Example 396)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-methylpropanoate (Compound No. 1172)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.38 (1H, s), 7.14-7.05 (2H, m), 6.90-6.83 (1H, m), 2.93 (1H, septet, J = 7.0 Hz), 2.13 (3H, s), 1.80-1.66 (1H, m), 1.36 (6H, d, J = 7.0Hz), 0.78-0.56 (4H, m).
Melting point (° C): 38-39.

(Example 397)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl pentanoate (Compound No. 1178)
^{1 H-NMR (200MHz, CDCl} 3) δppm: 7.38 (1H, s), 7.13-7.00 (2H, m), 6.90-6.77 (1H, m), 2.68 (2H, t, J = 7.3Hz), 2.12 (3H, s), 1.88-1.65 (3H, m), 1.60-1.35 (2H, m), 0.95 (3H, t, J = 7.3Hz), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 398)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-methylbutanoate (Compound No. 1184)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.37 (1H, s), 7.14-7.07 (2H, m), 6.89-6.82 (1H, m), 2.55 (2H, d, J = 7.0Hz), 2.27 (1H, br.septet, J = 6.8Hz), 2.12 (3H, s), 1.80-1.67 (1H, m), 1.07 (6H, d, J = 6.6Hz), 0.77-0.55 (4H, m).
Melting point (° C): 71-74.

(Example 399)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl pentadecanoate (Compound No. 1260)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.37 (1H, s), 7.10-7.00 (2H, m), 6.87-6.77 (1H, m), 2.66 (2H, t, J = 6.4Hz), 2.12 (3H, s), 1.85-1.65 (3H, m), 1.35-1.18 (22H, m), 0.95-0.82 (3H, m), 0.80-0.50 (4H, m).
Melting point (° C): 35-37.

(Example 400)
6-Chloro-3-phenoxy-5- (trimethylsilyl) -4-pyridazinol (Compound No. 2402)
¹ H-NMR (90 MHz, CDCl ₃ ) δ ppm: 12.0 (1H, br.s), 7.30-6.81 (5H, m), 0.28 (9H, s).
Melting point (° C): 119-120.

(Example 401)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl cyclobutanecarboxylate (Compound No. 1286)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.38 (1H, s), 7.14-7.05 (2H, m), 6.89-6.79 (1H, m), 3.58-3.40 (1H, m), 2.60-1.85 ( 6H, m), 2.13 (3H, s), 1.82-1.67 (1H, m), 0.80-0.67 (2H, m), 0.64-0.53 (2H, m).
Physical properties: Pasty.

(Example 402)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl cyclohexanecarboxylate (Compound No. 1298)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.37 (1H, s), 7.15-7.05 (2H, m), 6.90-6.80 (1H, m), 2.78-2.60 (1H, m), 2.12 (3H, s), 1.90-1.20 (10H, m), 0.80-0.50 (4H, m).
Melting point (° C): oily substance.

(Example 403)
3- (2-Isopropylphenoxy) -6-methyl-4-pyridazinol (Compound No. 2418)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.40-7.35 (1H, m), 7.25-7.16 (2H, m), 7.04-6.98 (1H, m), 6.43 (1H, s), 3.06 (1H , septet, J = 7.0Hz), 2.36 (3H, s), 1.18 (6H, d, J = 7.0Hz).
Melting point (° C): 259-260.

(Example 404)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-bromobutanoate (Compound No. 1334)
^{1 H-NMR (200MHz, CDCl} 3) δppm: 7.44 (1H, s), 7.14-7.05 (2H, m), 6.90-6.83 (1H, m), 4.45 (1H, t, J = 7.6Hz), 2.22 (1H, dq, J = 7.3, 7.6Hz), 2.13 (3H, s), 1.81-1.69 (1H, m), 1.17 (3H, t, J = 7.3Hz), 0.74-0.69 (2H, m), 0.58-0.56 (2H, m).
Physical properties: Pasty.

(Example 405)
3- (2-Isopropylphenoxy) -6- (trifluoromethyl) -4-pyridazinol (Compound No. 2431)
¹ H-NMR (60MHz, CDCl ₃ ) δppm: 7.60-6.70 (4H, m), 6.87 (1H, s), 2.97 (1H, septet, J = 7.0Hz), 1.10 (6H, d, J = 7.0Hz ).
Melting point (° C): 126.5.

(Example 406)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-chlorobutanoate (Compound No. 1340)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.40 (1H, s), 7.14-7.05 (2H, m), 6.89-6.82 (1H, m), 3.68 (2H, t, J = 6.2Hz), 2.91 (2H, t, J = 7.0Hz), 2.31-2.18 (2H, m), 2.11 (3H, s), 1.79-1.65 (1H, m), 0.80-0.67 (2H, m), 0.63-0.53 (2H , m).
Physical properties: Pasty.

(Example 407)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-methyl-2-butenoate (Compound No. 1358)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.44 (1H, s), 7.12-7.05 (2H, m), 6.88-6.80 (1H, m), 5.99-5.97 (1H, m), 2.26 (3H, d, J = 1.1Hz), 2.13 (3H, s), 2.04 (3H, d, J = 1.1Hz), 1.83-1.70 (1H, m), 0.77-0.64 (2H, m), 0.60-0.53 (2H , m).
Physical properties: Pasty.

(Example 408)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl (2E) -3-phenyl-2-propenoate (Compound No. 1364)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.96 (1H, d, J = 16.0 Hz), 7.63-7.59 (2H, m), 7.53 (1H, s), 7.48-7.43 (3H, m), 7.09 -7.05 (2H, m), 6.86-6.81 (1H, m), 6.66 (1H, d, J = 16.0Hz), 2.16 (3H, s), 1.83-1.75 (1H, m), 0.79-0.54 (4H , m).
Physical properties Amorphous.

(Example 409)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl methyl succinate (Compound No. 1382)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.44 (1H, s), 7.08-7.02 (2H, m), 6.88-6.74 (1H, m), 3.69 (3H, s), 3.01 (2H, t, J = 7.3Hz), 2.78 (2H, t, J = 7.3Hz), 2.11 (3H, s), 1.85-1.65 (1H, m), 0.80-0.50 (4H, m).
Physical property: Oily substance.

(Example 410)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-chlorobenzoate (Compound No. 1441)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 8.14 (1H, d, J = 8.8 Hz), 7.58 (1H, s), 7.59-7.39 (3H, m), 7.10-7.05 (2H, m), 6.88 -6.80 (1H, m), 2.16 (3H, s), 1.90-1.70 (1H, m), 0.85-0.50 (4H, m).
Physical property: Oily substance.

(Example 411)
3- (2-Methylphenoxy) -6- (2-thienyl) -4-pyridazinol (Compound No. 2478)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.56-7.48 (2H, m), 7.21-7.00 (4H, m), 6.97-6.90 (1H, m), 6.69 (1H, s), 2.11 (3H, s).
Melting point (° C): 86-87.

(Example 412)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-methylbenzoate (Compound No. 1481)
^{1 H-NMR (200MHz, CDCl} 3) δppm: 8.20 (1H, d, J = 7.0Hz), 7.56 (1H, s), 7.52 (1H, d, J = 7.7Hz), 7.40-7.28 (2H, m ), 7.10-7.00 (2H, m), 6.90-6.88 (1H, m), 2.69 (3H, s), 2.16 (3H, s), 1.90-1.70 (1H, m), 0.82-0.65 (2H, m ), 0.65-0.50 (2H, m).
Physical property: Oily substance.

(Example 413)
3,6-Bis (2-methylphenoxy) -4-pyridazinol (Compound No. 2492)
¹ H-NMR (60 MHz, DMF-d ₇ ) δ ppm: 7.40-6.90 (8H, m), 5.79 (1H, s), 2.19 (6H, br.s).
Melting point (° C): 247-250.

(Example 414)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-methoxybenzoate (Compound No. 1522)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.09 (1H, dd, J = 7.9, 2.0Hz), 7.68-7.57 (1H, m), 7.59 (1H, s), 7.15-7.03 (4H, m) , 6.90-6.82 (1H, m), 3.96 (3H, s), 2.17 (3H, s), 1.96-1.72 (1H, m), 0.78-0.65 (2H, m), 0.65-0.51 (2H, m) .
Physical properties: Gummy.

(Example 415)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-methylbenzoate (Compound No. 1531)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.05-8.00 (2H, m), 7.58 (1H, s), 7.55-7.38 (2H, m), 7.10-7.05 (2H, m), 6.88-6.80 ( 1H, m), 2.46 (3H, s), 2.16 (3H, s), 1.90-1.68 (1H, m), 0.80-0.50 (4H, m).
Physical property: Oily substance.

(Example 416)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-chlorobenzoate (Compound No. 1537)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.16 (2H, d, J = 8.8Hz), 7.59 (1H, s), 7.54 (2H, d, J = 8.8Hz), 7.14-7.07 (2H, m ), 6.88-6.83 (1H, m), 2.15 (3H, s), 1.84-1.69 (1H, m), 0.80-0.70 (2H, m), 0.62-0.55 (2H, m).
Physical properties: amorphous.

(Example 417)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-bromobenzoate (Compound No. 1543)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.07 (2H, d, J = 8.6Hz), 7.70 (2H, d, J = 8.6Hz), 7.59 (1H, s), 7.12-7.03 (2H, m ), 6.89-6.82 (1H, m), 2.15 (3H, s), 1.83-1.67 (1H, m), 0.78-0.50 (4H, m).
Physical properties: amorphous.

(Example 418)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-iodobenzoate (Compound No. 1549)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 7.94 (2H, s), 7.93 (1H, m), 7.62 (1H, s), 7.29 (1H, s), 7.12-7.09 (2H, m), 6.89 -6.87 (1H, m), 2.17 (3H, s), 1.84-1.73 (1H, m), 0.79-0.70 (2H, m), 0.62-0.55 (2H, m).
Physical properties: Pasty.

(Example 419)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-methylbenzoate (Compound No. 1566)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.10 (2H, d, J = 8.1Hz), 7.60 (1H, s), 7.34 (2H, d, J = 8.1Hz), 7.12-7.03 (2H, m ), 6.88-6.81 (1H, m), 2.46 (3H, s), 2.15 (3H, s), 1.85-1.71 (1H, m), 0.78-0.65 (2H, m), 0.62-0.52 (2H, m ).
Melting point (° C): 77.5-78.

(Example 420)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-tert-butylbenzoate (Compound No. 1575)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.15 (2H, d, J = 8.8Hz), 7.59 (1H, s), 7.56 (2H, d, J = 8.8Hz), 7.09-7.06 (2H, m ), 6.86-6.82 (1H, m), 2.15 (3H, s), 1.37 (9H, s), 1.82-1.73 (1H, m), 0.76-0.69 (2H, m), 0.60-0.56 (2H, m ).
Melting point (° C): 139-142.

(Example 421)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-nitrobenzoate (Compound No. 1593)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.41 (4H, s), 7.61 (1H, s), 7.14-7.08 (2H, m), 6.89-6.83 (1H, m), 2.17 (3H, s) , 1.81-1.70 (1H, m), 0.80-0.71 (2H, m), 0.62-0.54 (2H, m).
Physical properties: amorphous.

(Example 422)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-methoxybenzoate (Compound No. 1599)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.17 (2H, d, J = 8.8Hz), 7.60 (1H, s), 7.12-7.04 (2H, m), 7.01 (2H, d, J = 8.8Hz ), 6.88-6.82 (1H, m), 3.90 (1H, s), 2.16 (3H, s), 1.85-1.71 (1H, m), 0.78-0.69 (2H, m), 0.60-0.52 (2H, m ).
Physical properties: amorphous.

(Example 423)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,4-dichlorobenzoate (Compound No. 1616)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.11 (1H, d, J = 8.4Hz), 7.60-7.57 (2H, m), 7.42 (1H, dd, J = 8.4, 2.2Hz), 7.14-7.08 (2H, m), 6.89-6.83 (1H, m), 2.15 (3H, s), 1.85-1.72 (1H, m), 0.78-0.67 (2H, m), 0.63-0.54 (2H, m).
Physical properties: amorphous.

(Example 424)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl phthalate (Compound No. 1620)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.98-7.94 (1H, m), 7.88-7.84 (1H, m), 7.81-7.71 (2H, m), 7.57, (1H, s), 7.28-7.17 (6H, m), 7.08-7.03 (1H, m), 3.70 (3H, s), 2.26 (3H, s), 2.15 (3H, s).
Physical properties: amorphous.

(Example 425)
Potassium 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinolate (Compound No. 3811)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.05-6.95 (2H, m), 6.83-6.72 (1H, m), 6.47 (1H, s), 2.00-1.83 (1H, m), 0.80-0.64 (2H, m), 0.64-0.48 (2H, m).
Melting point (° C): 187-189.

(Example 426)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl isophthalate (Compound No. 1631)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.61 (1H, t, J = 1.5Hz), 8.54-8.47 (1H, m), 8.22-8.16 (1H, m), 7.71 (1H, t, J = 8.1Hz), 7.61 (1H, s), 7.15-6.96 (4H, m), 6.89-6.82 (1H, m), 3.67 (3H, s), 2.44 (3H, s), 2.17 (3H, s), 1.88-1.72 (1H, m), 0.83-0.71 (2H, m), 0.64-0.53 (2H, m).
Physical properties: amorphous.

(Example 427)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-furoate (Compound No. 1643)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.74–7.73 (1H, m), 7.56 (1H, s), 7.50 (1H, dd, J = 3.7, 0.7 Hz), 7.13-7.04 (2H, m) , 6.88-6.81 (1H, m), 6.65-6.63 (1H, m), 2.15 (3H, s), 1.85-1.71 (1H, m), 0.78-0.69 (2H, m), 0.62-0.52 (2H, m).
Physical properties: Pasty.

(Example 428)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-thiophenecarboxylate (Compound No. 1649)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.07-8.05 (1H, m), 7.78-7.75 (1H, m), 7,58 (1H, s), 7.24-7.20 (1H, m), 7.13- 7.06 (2H, m), 6.89-6.83 (1H, m), 2.16 (3H, s), 1.83-1.71 (1H, m), 0.80-0.70 (2H, m), 0.65-0.55 (2H, m).
Physical properties: amorphous.

(Example 429)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl isobutyl carbonate (Compound No. 1770)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.49 (1H, s), 7.15-7.05 (2H, m), 6.89-6.82 (1H, m), 4.13 (2H, d, J = 6.6Hz), 2.14 (3H, s), 2.09 (1H, br. Septet, J = 7.0Hz), 1.88-1.68 (1H, m), 1.01 (6H, d, J = 7.0Hz), 0.78-0.52 (4H, m).
Melting point (° C): 72-74.

(Example 430)
Allyl 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl carbonate (Compound No. 1811)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.50 (1H, s), 7.15-7.06 (2H, m), 6.89-6.82 (1H, m), 6.10-5.90 (1H, m), 5.51-5.35 ( 2H, m), 4.84-4.80 (2H, m), 2.14 (3H, s), 1.85-1.70 (1H, m), 0.78-0.53 (4H, m).
Physical property: Oily substance.

(Example 431)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl dimethyl carbamate (Compound No. 1891)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.56 (1H, s), 7.13-7.05 (2H, m), 6.89-6.82 (1H, m), 3.16 (3H, s), 3.05 (3H, s) , 2.15 (3H, s), 1.85-1.71 (1H, m), 0.78-0.54 (4H, m).
Melting point (° C): 136-138.

(Example 432)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl diethylcarbamate (Compound No. 1911)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.58 (1H, s), 7.10-7.07 (2H, m), 6.87-6.83 (1H, m), 3.48 (2H, q, J = 7.3Hz), 3.41 (2H, q, J = 7.0Hz), 2.15 (3H, s), 1.82-1.72 (1H, m), 1.29 (3H, t, J = 7.3Hz), 1.23 (3H, t, J = 7.0Hz) , 0.74-0.57 (4H, m).
Melting point (° C): 119-121.

(Example 433)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl diisopropylcarbamate (Compound No. 1920)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.61 (1H, s), 7.10-7.00 (2H, m), 6.90-6.85 (1H, m), 4.20-3.90 (2H, m), 2.14 (3H, s), 1.87-1.67 (1H, m), 1.45-1.20 (12H, m), 0.80-0.50 (4H, m).
Melting point (° C): 103-105.

(Example 434)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-thiophenesulfonate (Compound No. 3792)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.89-7.82 (2H, m), 7.58 (1H, s), 7.22-7.13 (1H, m), 7.13-7.02 (2H, m), 6.84-6.79 ( 1H, m), 1.99 (3H, s), 1.69-1.53 (1H, m), 0.70-0.48 (4H, m).
Physical properties: amorphous.

(Example 435)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl methyl (phenyl) carbamate (Compound No. 1946)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.40-7.25 (6H, m), 7.11-7.08 (2H, m), 6.87-6.82 (1H, m), 3.42 (3H, br.s), 2.15 ( 3H, br.s), 1.82-1.68 (1H, m), 0.71-0.56 (4H, m).
Physical properties: amorphous.

(Example 436)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl diphenylcarbamate (Compound No. 1952)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.45-7.28 (11H, m), 7.16-7.09 (2H, m), 6.87-6.82 (1H, m), 2.11 (3H, s), 1.79-1.66 ( 1H, m), 0.69-0.56 (4H, m).
Physical properties: amorphous.

(Example 437)
O- [6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] S-methyl thiocarbonate (Compound No. 1958)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.47 (1H, s), 7.13-7.06 (2H, m), 6.89-6.83 (1H, m), 2.49 (3H, s), 2.14 (3H, s) , 1.83-1.69 (1H, m), 0.78-0.65 (2H, m), 0.63-0.55 (2H, m).
Physical properties: Pasty.

(Example 438)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl ethanesulfonate (Compound No. 2034)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.58 (1H, s), 7.15-7.05 (2H, m), 6.92-6.82 (1H, m), 3.58 (2H, q, J = 7.4Hz), 2.15 (3H, s), 1.82-1.68 (1H, m), 1.64 (3H, t, J = 7.4Hz), 0.78-0.52 (4H, m).
Melting point (° C): 96-97.

(Example 439)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-propanesulfonate (Compound No. 2051)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.58 (1H, s), 7.18-7.05 (2H, m), 6.94-6.83 (1H, m), 3.53 (2H, t, J = 7.7Hz), 2.20 -2.00 (2H, m), 2.15 (3H, s), 1.82-1.67 (1H, m), 1.15 (3H, t, J = 7.7Hz), 0.80-0.50 (4H, m).
Melting point (° C): 70.5-71.5.

(Example 440)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-propanesulfonate (Compound No. 2060)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.59 (1H, s), 7.18-7.07 (2H, m), 6.93-6.82 (1H, m), 3.75 (1H, septet, 7.0Hz), 2.15 (3H , S), 1.85-1.65 (1H, m), 1.65 (6H, d, J = 7.0Hz), 0.78-0.50 (4H, m).
Physical property: Oily substance.

(Example 441)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-octanesulfonate (Compound No. 2066)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.15-7.07 (2H, m), 6.89-6.85 (1H, s), 3.60-3.50 (2H, m), 2.15 (3H, s), 2.15-1.98 (2H, m), 1.83-1.67 (1H, m), 1.58-1.15 (10H, m), 0.95-0.83 (3H, m), 0.80-0.68 (2H, m), 0.65- 0.55 (2H, m).
Physical properties: Pasty.

(Example 442)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl chloromethanesulfonate (Compound No. 2072)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.58 (1H, s), 7.18-7.09 (2H, m), 6.92-6.85 (1H, m), 5.02 (2H, s), 2.16 (3H, s) , 1.83-1.68 (1H, m), 0.80-0.68 (2H, m), 0.65-0.55 (2H, m).
Physical properties: Pasty.

(Example 443)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,2,2-trifluoroethanesulfonate (Compound No. 2136)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.19-7.05 (2H, m), 6.90 (1H, dd, J = 6.6, 2.9 Hz), 4.39 (2H, q, J = 8.2Hz), 2.15 (3H, s), 1.80-1.65 (1H, m), 0.80-0.50 (4H, m).
Physical properties: amorphous.

(Example 444)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-chlorobenzenesulfonate (Compound No. 2212)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.01-7.92 (2H, m), 7.62-7.53 (3H, m), 7.13-7.00 (2H, m), 6.85-6.77 (1H, m), 2.04 ( 3H, s), 1.58-1.45 (1H, m), 0.70-0.45 (4H, m).
Physical properties: Gummy.

(Example 445)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-nitrobenzenesulfonate (Compound No. 2300)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.50-8.39 (2H, m), 8.33-8.20 (2H, m), 7.59 (1H, s), 7.15-7.00 (2H, m), 6.85-6.75 ( 1H, m), 1.94 (3H, s), 1.65-1.45 (1H, m), 0.75-0.45 (4H, m).
Physical properties: Gummy.

(Example 446)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-methoxybenzenesulfonate (Compound No. 2309)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.99-7.91 (2H, m), 7.61 (1H, s), 7.11-6.98 (4H, m), 6.80 (1H, dd, J = 2.6Hz, 6.6Hz ), 3.90 (3H, s), 1.95 (3H, s), 1.60-1.45 (1H, m), 0.70-0.45 (4H, m).
Physical properties: candy-like.

(Example 447)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,4,6-trimethylbenzenesulfonate (Compound No. 2315)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.59 (1H, s), 7.13-6.98 (4H, m), 6.85-6.75 (1H, m), 2.70 (6H, s), 2.32 (3H, s) , 2.04 (3H, s), 1.65-1.45 (1H, m), 0.78-0.44 (4H, m).
Physical properties: amorphous.

(Example 448)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,4,6-triisopropylbenzenesulfonate (Compound No. 2321)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.52 (1H, s), 7.28-7.20 (2H, m), 7.10-6.98 (2H, m), 6.85-6.75 (1H, m), 4.16 (2H, septet, J = 6.6Hz), 2.93 (1H, septet, J = 6.6Hz), 1.93 (3H, s), 1.75-1.50 (1H, m), 1.35-1.20 (18H, m), 0.75-0.45 (4H , m).
Physical properties: amorphous.

(Example 449)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazoyl-5-yl 1,2-benzene Disulfonate (Compound No. 2327)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.52-8.40 (1H, m), 8.15-8.07 (1H, m), 8.00-7.82 (2H, m), 7.63 (1H, s), 7.18 (2H, s), 7.15-6.97 (3H, m), 6.79 (1H, dd, J = 7.0, 2.6Hz), 3.84 (3H, s), 2.11 (3H, s), 1.99 (3H, s), 1.75-1.57 (1H, m), 0.74-0.45 (4H, m).
Physical properties: candy-like.

(Example 450)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-chloro-3-nitrobenzenesulfonate (Compound No. 3786)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.55 (1H, d, J = 2.2 Hz), 8.18 (1H, dd, J = 8.8, 2.2 Hz), 7.81 (1H, d, J = 8.8 Hz), 7.59 (1H, s), 7.13-7.06 (2H, m), 6.84-6.79 (1H, m), 1.98 (3H, s), 1.61-1.48 (1H, m), 0.68-0.52 (4H, m).
Physical properties: amorphous.

(Example 451)
6-Chloro-3- [2- (2-chloro-2-fluorocyclopropyl) phenoxy] -4-pyridazinol (Compound No. 2519)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.42-7.15 (4H, m), 6.70 (1H, s), 2.80-2.62 (1H, m), 2.18-1.65 (2H, m).
Melting point (° C): 175-177.

(Example 452)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,5-dichlorobenzenesulfonate (Compound No. 3780)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.09-8.08 (1H, m), 7.61-7.52 (3H, m), 7.12-7.01 (2H, m), 6.81-6.76 (1H, m), 1.98 ( 3H, s), 1.67-1.49 (1H, m), 0.82-0.60 (2H, m), 0.58-0.48 (2H, m).
Physical properties: amorphous.

(Example 453)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 10H-phenothiazine-10-carboxylate (Compound No. 3720)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.76-7.67 (3H, m), 7.49-7.40 (3H, m), 7.40-7.23 (3H, m), 7.20-7.10 (2H, m), 6.95- 6.83 (1H, m), 2.19 (3H, s), 1.88-1.70 (1H, m), 0.85-0.57 (4H, m).
Physical properties: amorphous.

(Example 454)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 9H-carbazole-9-carboxylate (Compound No. 3714)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.40 (2H, d, J = 7.4Hz), 8.02 (2H, d, J = 7.0Hz), 7.99 (1H, s), 7.60-7.35 (4H, m ), 7.13-7.03 (2H, m), 6.92-6.80 (1H, m), 2.19 (3H, s), 1.90-1.73 (1H, m), 0.84-0.50 (4H, m).
Melting point (° C): 157-159.

(Example 455)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,4-dihydro-2 (1H) -isoquinolinecarboxylate (Compound No. 3708)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.59 (1H, s), 7.32-7.02 (6H, m), 6.90-6.78 (1H, m), 4.86 (1H, s), 4.72 (1H, s) , 3.92 (1H, t, J = 5.9Hz), 3.81 (1H, t, J = 5.9Hz), 3.05-2.95 (2H, m), 2.14 (3H, s), 1.86-1.67 (1H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 456)
3- [3- (Benzyloxy) phenoxy] -6-chloro-4-pyridazinol (Compound No. 2547)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.48-7.25 (6H, m), 6.94-6.66 (4H, m), 5.07 (2H, s).
Melting point (° C): 184-185.

(Example 457)
3- [4- (Benzyloxy) phenoxy] -6-chloro-4-pyridazinol (Compound No. 2548)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.48-7.28 (5H, m), 7.12-6.96 (4H, m), 6.58 (1H, s), 5.07 (2H, s).
Melting point (° C): 170-180.

(Example 458)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-thiomorpholine carboxylate (Compound No. 3702)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.53 (1H, s), 7.15-7.04 (2H, m), 6.92-6.80 (1H, m), 4.05-3.78 (4H, m), 2.75-2.64 ( 4H, m), 2.13 (3H, s), 1.85-1.65 (1H, m), 0.80-0.54 (4H, m).
Physical properties: candy-like.

(Example 459)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,6-dimethyl-4-morpholinecarboxylate (Compound No. 3696)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.54 (1H, s), 7.18-7.05 (2H, m), 6.94-6.80 (1H, m), 4.17-3.97 (2H, m), 3.78-3.55 ( 2H, m), 2.95-2.60 (2H, m), 2.14 (3H, s), 1.85-1.67 (1H, m), 1.35-1.15 (6H, m), 0.80-0.54 (4H, m).
Physical properties: candy-like.

(Example 460)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3690)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.13-7.06 (2H, m), 6.90-6.83 (1H, m), 3.70-3.55 (8H, m), 2.14 (3H, s), 1.83-1.68 (1H, m), 0.80-0.65 (2H, m), 0.65-0.53 (2H, m).
Melting point (° C): 102.5-103.5.

(Example 461)
6-Chloro-3-[(1-methyl-1H-indol-4-yl) oxy] -4-pyridazinol (Compound No. 2565)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.29 (1H, d, J = 8.4 Hz), 7.17 (1H, t, J = 7.7 Hz), 7.13 (1H, d, J = 2.9 Hz), 6.85 (1H, d, J = 7.7Hz), 6.72 (1H, s), 6.23 (1H, d, J = 2.9Hz), 4.87 (3H, s).
Melting point (° C): 203-206.

(Example 462)
6-Chloro-3-[(1-methyl-1H-indol-7-yl) oxy] -4-pyridazinol (Compound No. 2568)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.42 (1H, d, J = 7.0 Hz), 7.07 (1H, d, J = 2.9 Hz), 6.99 (1H, t, J = 7.7 Hz), 6.86 (1H, d, J = 6, 6Hz), 6.74 (1H, s), 6.44 (1H, d, J = 2.9Hz), 3.80 (3H, s).
Melting point (° C): 219-221.

(Example 463)
1- {4-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] -3-methylphenyl} ethanone (Compound No. 2570)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.94-7.86 (2H, m), 7.21-7.16 (1H, m), 6.75 (1H, s), 2.60 (3H, s), 2.25 (3H, s ).
Melting point (° C): 182-284.

(Example 464)
1- {4-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] -3-methylphenyl} ethanone O-methyloxime (Compound No. 2571)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.59-7.51 (2H, m), 7.11-7.06 (1H, m), 6.71 (1H, s), 3.95 (3H, s), 2.20 (3H, s ).
Melting point (° C): 189-192.

(Example 465)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-phenyl-1-piperazinecarboxylate (Compound No. 3684)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.60 (1H, s), 7.35-7.23 (2H, m), 7.13-7.04 (2H, m), 7.00-6.80 (4H, m), 3.95-3.84 ( 2H, m), 3.84-3.72 (2H, m), 3.31-3.18 (4H, m), 2.15 (3H, s), 1.86-1.66 (1H, m), 0.80-0.53 (4H, m).
Physical properties: candy-like.

(Example 466)
4-{[4- (Benzoyloxy) -6-chloro-3-pyridazinyl] oxy} -3-methylphenyl benzoate (Compound No. 3850)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 8.21-8.17 (4H, m), 7.72-7.48 (7H, m), 7.22-7.07 (3H, m), 2.21 (3H, s).
Melting point (° C): 118-120.

(Example 467)
Methyl 3-[(6-chloro-4-hydroxy-3-pyridazinyl) oxy] -4-methoxybenzoate (Compound No. 2574)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.95 (1H, dd J = 8.6, 2.2 Hz), 7.78 (1H, d, J = 1.8 Hz), 7.19 (1H, d, J = 8.8 Hz), 6.71 (1H, s), 3.87 (3H, s), 3.84 (3H, s).
Melting point (° C): 115-123.

(Example 468)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-methyl-1-piperazinecarboxylate (Compound No. 3678)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.59 (1H, s), 7.15-7.04 (2H, m), 6.90-6.80 (1H, m), 3.80-3.55 (4H, m), 2.54-2.40 ( 4H, m), 2.32 (3H, s), 2.14 (3H, s), 1.85-1.67 (1H, m), 0.80-0.52 (4H, m).
Physical properties: candy-like.

(Example 469)
6-Chloro-3- (2-isopropenyl-6-methylphenoxy) -4-pyridazinol (Compound No. 2577)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.20-7.10 (3H, m), 6.66 (1H, s), 5.01 (1H, m), 4.95 (1H, m), 2.15 (3H, s), 1.99 (3H, s).
Melting point (° C): 183-186.

(Example 470)
6-Chloro-3-[(1,1-dimethyl-2,3-dihydro-1H-inden-5-yl) oxy-4-pyridazinol (Compound No. 2585)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.15 (1H, d, J = 8.1 Hz), 6.95 (2H, br.d, J = 8.1 Hz), 6.68 (1H, s), 2.89 (2H, t, J = 7.3Hz), 1.96 (2H, t, J = 7.3Hz), 1.27 (6H, s).
Melting point (° C): 209-212.

(Example 471)
3- (3-Bromo-6-cyclopropyl-2-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 2587)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.38 (1H, d, J = 8.4 Hz), 6.78 (1H, d, J = 8.4 Hz), 6.72 (1H, s), 2.22 (3H, s) , 1.85-1.72 (1H, m), 0.85-0.72 (2H, m), 0.65-0.50 (2H, m).
Melting point (° C): 234-235.

(Example 472)
6-Chloro-3- (6-cyclopropyl-2-methyl-3-nitrophenoxy) -4-pyridazinol (Compound No. 2589)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.80 (1H, d, J = 8.4 Hz), 7.02 (1H, d, J = 8.4 Hz), 6.77 (1H, s), 2.32 (3H, s) 1.99-1.88 (1H, m), 0.95-0.88 (2H, m), 0.74-0.70 (2H, m).
Melting point (° C): 140-143.

(Example 473)
6-Chloro-3-[(5-methyl-1,3-dihydro-2-benzofuran-4-yl) oxy] -4-pyridazinol (Compound No. 2592)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.20 (1H, d, J = 7.7 Hz), 7.08 (1H, d, J = 7.7 Hz), 5.06 (2H, br.s), 4.88 (2H, br.s), 2.16 (3H, s).
Melting point (° C): 188-200.

(Example 474)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,2,6,6-tetramethyl-1-piperidinecarboxylate (Compound No. 3672)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7,53 (1H, s), 7.14-7.03 (2H, m), 6.90-6.78 (1H, m), 2.13 (3H, s), 1.90-1.62 ( 7H, m), 1.55 (12H, s), 0.80-0.52 (4H, m).
Physical properties: candy-like.

(Example 475)
6-Chloro-3- (2-fluoro-3,5,6-trimethylphenoxy) -4-pyridazinol (Compound No. 2597)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 6.92 (1H, d, J = 7.0 Hz), 6.73 (1H, s), 2.24 (3H, s), 2.21 (3H, s), 2.06 (3H, s).
Melting point (° C): 258-260.

(Example 476)
6-Chloro-3- (2-chloro-3,5,6-trimethylphenoxy) -4-pyridazinol (Compound No. 2599)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δppm: 7.11 (1H, s), 6.86 (1H, br.s), 2.29 (3H, s), 2.24 (3H, s), 1.99 (3H, s) .
Melting point (° C): 298-300.

(Example 477)
6-Chloro-3- (2-iodo-3,5,6-trimethylphenoxy) -4-pyridazinol (Compound No. 2600)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.06 (1H, s), 6.75 (1H, s), 2.40 (3H, s), 2.26 (3H, s), 2.09 (3H, s).
Melting point (° C): 235 (decomposition).

(Example 478)
6-Chloro-3- (2-ethyl-3,5,6-trimethylphenoxy) -4-pyridazinol (Compound No. 2601)
¹ H-NMR (200MHz, DMSO-d ₆ ) δppm: 6.95 (1H, s), 6.81 (1H, br.s), 2.32 (2H, q, J = 7.5Hz), 2.24 (3H, s), 2.12 (3H, s), 1.94 (3H, s), 1.04 (3H, t, J = 7.5Hz).
Melting point (° C): 188-195.

(Example 479)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1,4-dioxa-8-azaspiro [4.5] decane-8-carboxylate (Compound No. 3666)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.15-7.04 (2H, m), 6.92-6.80 (1H, m), 3.99 (4H, s), 3.85-3.62 (4H, m), 2.14 (3H, s), 1.85-1.65 (5H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 480)
6-Chloro-3- (2-isopropenyl-3,5,6-trimethylphenoxy) -4-pyridazinol (Compound No. 2605)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 6.91 (1H, s), 6.58 (1H, s), 5.00-4.90 (2H, bm), 2.27 (3H, s), 2.20 (3H, s), 2.07 (3H, s), 1.96 (3H, s).
Physical properties: amorphous.

(Example 481)
1- [6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] 4-ethyl 1,4-piperidinedicarboxylate (Compound No. 3660)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.56 (1H, s), 7.13-7.04 (2H, m), 6.90-6.80 (1H, m), 4.30-4.00 (2H, m), 3.35-3.02 ( 2H, m), 2.65-2.45 (1H, m), 2.14 (3H, s), 2.10-1.93 (3H, m), 1.93-1.65 (4H, m), 1.25 (3H, t, J = 7.0Hz) , 0.80-0.54 (4H, m).
Physical properties: candy-like.

(Example 482)
1- {2-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] -3,4,6-trimethylphenyl} ethanone (Compound No. 2607)
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.55 (1H, s), 6.72 (1H, s), 2.45 (3H, s), 2.36 (3H, s), 2.29 (3H, s), 2.11 ( 3H, s).
Physical properties: amorphous.

(Example 483)
6-Chloro-3- (2,3,5-trimethyl-6-nitrophenoxy) -4-pyridazinol (Compound No. 2608)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.11 (1H, s), 6.65 (1H, s), 2.33 (3H, s), 2.28 (3H, s), 2.05 (3H, s).
Melting point (° C): 172-174.

(Example 484)
6-Chloro-3- (2,4-dichloro-3,5,6-trimethylphenoxy) -4-pyridazinol (Compound No. 2609)
¹ H-NMR (200 MHz, DMSO-d ₆ ) δ ppm: 6.91 (1H, s), 2.46 (3H, s), 2.36 (3H, s), 2.10 (3H, s).

(Example 485)
6-Chloro-3- (2,3,4,5,6-pentamethylphenoxy) -4-pyridazinol (Compound No. 2614)
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 6.69 (1H, s), 2.23 (3H, s), 2.21 (6H, s), 2.02 (6H, s).
Melting point (° C): 238-240 (decomposition).

(Example 486)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,3-dimethylbutanoate (Compound No. 2661)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.37 (1H, s), 7.13-7.05 (2H, s), 6.88-6.82 (1H, s), 2.55 (2H, s), 2.12 (3H, s) , 1.82-1.67 (1H, m), 1.15 (9H, s), 0.80-0.65 (2H, m), 0.63-0.52 (2H, m).
Melting point (° C): 91-92.

(Example 487)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-adamantanecarboxylate (Compound No. 2671)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.37 (1H, s), 7.12-7.05 (2H, m), 6.92-6.80 (1H, m), 2.13 (3H, s), 2.08 (9H, s) , 1.76 (7H, br.s), 0.85-0.45 (4H, m).
Physical property: Oily substance.

(Example 488)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-methyl acrylate (Compound No. 2677)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.48 (1H, s), 7.14-7.05 (2H, m), 6.89-6.83 (1H, m), 6.46 (1H, br.s), 5.91 (1H, br.s), 2.13 (3H, s), 2.09 (3H, s), 1.81-1.68 (1H, m), 0.78-0.53 (4H, m).
Melting point (° C): 98-100.

(Example 489)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-bromo-2-methylpropanoate (Compound No. 2697)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.47 (1H, s), 7.11-7.08 (2H, m), 6.89-6.85 (1H, m), 2.13 (3H, s), 2.10 (6H, s) , 1.77-1.69 (1H, m), 0.74-0.58 (4H, m).
Melting point (° C): 69-71.

(Example 490)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-chloro-2,2-dimethylpropanoate (Compound No. 2703)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.43 (1H, s), 7.13-7.05 (2H, m), 6.90-6.84 (1H, m), 3.76 (2H, s), 2.13 (3H, s) , 1.83-1.65 (1H, m), 1.50 (6H, s), 0.85-0.45 (4H, br.s).
Melting point (° C): 112-115.

(Example 491)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5-bromopentanoate (Compound No. 2709)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.83 (1H, s), 7.11-7.05 (2H, m), 6.86-6.82 (1H, m), 3.43 (2H, d, J = 6.2Hz), 2.73 (2H, d, J = 7.0Hz), 2.12 (3H, s), 2.04-1.93 (4H, m), 1.77-1.69 (1H, m), 0.74-0.56 (4H, m).
Physical properties: candy-like.

(Example 492)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl hydratropate (Compound No. 2715)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.42-7.20 (5H, m), 7.32 (1H, s), 7.15-7.02 (2H, m), 6.86-6.75 (1H, m), 4.20-4.00 ( 1H, m), 2.04 (3H, s), 1.66 (3H, d, J = 7.0 Hz), 1.70-1.50 (1H, m), 0.70-0.42 (4H, m).
Physical property: Oily substance.

(Example 493)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl (4-methoxyphenyl) acetate (Compound No. 2721)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.37 (1H, s), 7.27 (2H, d, J = 8.2 Hz), 7.13-7.05 (2H, m), 6.89-6.80 (3H, m), 3.91 (2H, s), 3.76 (3H, s), 2.07 (3H, s), 1.73-1.60 (1H, m), 0.75-0.50 (4H, m).
Physical properties: Pasty.

(Example 494)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl ethyl succinate (Compound No. 2727)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.08-6.92 (2H, m), 6.85-6.68 (1H, m), 6.55 (1H, s), 4.14 (2H, br.q, J = 7.1Hz) , 3.00 (1H, t, J = 7.0Hz), 2.76 (1H, t, J = 7.0Hz), 2.61 (2H, br.s), 1.98 (3H, s), 1.78-1.60 (1H, m), 1.25 (3H, t, J = 7.1Hz), 0.75-0.40 (4H, m).
Physical properties: amorphous.

(Example 495)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-methyl-1-piperidinecarboxylate (Compound No. 3654)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.56 (1H, s), 7.14-7.04 (2H, m), 6.90-6.80 (1H, m), 4.35-4.10 (2H, m), 3.15-2.80 ( 2H, m), 2.14 (3H, s), 1.85-1.50 (4H, m), 1.35-1.06 (2H, m), 0.96 (3H, d, J = 6.2Hz), 0.80-0.50 (4H, m) .
Physical properties: candy-like.

(Example 496)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-bromo-1-piperidinecarboxylate (Compound No. 3648)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.15-7.04 (2H, m), 6.90-6.80 (1H, m), 4.54-4.38 (1H, m), 4.00-3.53 ( 4H, m), 2.30-1.90 (7H, m), 1.85-1.67 (1H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 497)
Bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] succinate (Compound No. 2733)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.32 (2H, s), 7.14-7.03 (4H, m), 6.88-6.81 (2H, m), 3.17 (4H, s), 2.10 (6H, s) , 1.80-1.65 (2H, m), 0.78-0.53 (8H, m).
Physical properties: candy-like.

(Example 498)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl methoxyacetate (Compound No. 2752)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.43 (1H, s), 7.15-7.04 (2H, m), 6.90-6.82 (1H, m), 4.41 (2H, s), 3.55 (3H, s) , 2.12 (3H, s), 1.82-1.67 (1H, m), 0.80-0.67 (2H, m), 0.64-0.55 (2H, m).
Physical properties: Pasty.

(Example 499)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl phenoxyacetate (Compound No. 2758)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.42 (1H, s), 7.29-7.25 (2H, m), 7.23-6.96 (5H, m), 6.89-6.83 (1H, m), 5.00 (2H, s), 2.08 (3H, s), 1.73-1.64 (1H, m), 0.71-0.54 (4H, m).
Physical properties: candy-like.

(Example 500)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-phenoxypropanoate (Compound No. 2764)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 7.33 (1H, s), 7.25-7.19 (2H, m), 7.17-7.04 (2H, m), 7.00-6.91 (3H, m), 6.86-6.82 ( 1H, m), 5.09 (1H, q, J = 6.6Hz), 2.05 (3H, s), 1.84 (3H, d, J = 6.6Hz), 1.64-1.58 (1H, m), 0.68-0.52 (4H , m).
Physical properties: candy-like.

(Example 501)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl methoxy (phenyl) acetate (Compound No. 2770)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.56-7.51 (2H, m), 7.40-7.30 (4H, m), 7.12-7.02 (2H, m), 6.83-6.78 (1H, m), 5.10 ( 1H, s), 3.52 (3H, s), 2.01 (3H, s), 1.67-1.50 (1H, m), 0.70-0.43 (4H, m).
Physical properties: Pasty.

(Example 502)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3- (methylsulfanyl) propanoate (Compound No. 2776)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.42 (1H, s), 7.10-7.00 (2H, m), 6.90-6.77 (1H, m), 3.07-2.83 (4H, m), 2.17 (3H, s), 2.12 (3H, s), 1.85-1.65 (1H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 503)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl oxo (2-thienyl) acetate (Compound No. 2782)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.07 (1H, dd, J = 1.5Hz, 4.1Hz), 7.77 (1H, dd, J = 1.5Hz, 4.1Hz), 7.58 (1H, s), 7.22 (1H, t, J = 4.0Hz), 7.10-7.02 (2H, m), 6.90-6.77 (1H, m), 2.15 (3H, s), 1.90-1.70 (1H, m), 0.85-0.50 (4H , m).
Physical properties: candy-like.

(Example 504)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-fluorobenzoate (Compound No. 2788)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.17-8.09 (1H, m), 7.73-7.62 (1H, m), 7.57 (1H, s), 7.36-7.20 (2H, m), 7.09-7.07 ( 2H, m), 6.87-6.82 (1H, m), 2.16 (3H, s), 1.85-1.72 (1H, m), 0.76-0.56 (4H, m).
Physical properties: amorphous.

(Example 505)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-bromobenzoate (Compound No. 2805)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.20-8.05 (1H, m), 7.85-7.70 (1H, m), 7.59 (1H, s), 7.55-7.38 (2H, m), 7.15-7.00 ( 2H, m), 6.90-6.80 (1H, m), 2.17 (3H, s), 1.88-1.70 (1H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 506)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-iodobenzoate (Compound No. 2814)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.20-8.05 (2H, m), 7.60-7.44 (2H, m), 7.35-7.20 (1H, m), 7.13-7.00 (2H, m), 6.90- 6.78 (1H, m), 2.17 (3H, s), 1.90-1.72 (1H, m), 0.85-0.50 (4H, m).
Physical properties: candy-like.

(Example 507)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2- (trifluoromethyl) benzoate (Compound No. 2820)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.13-8.09 (1H, m), 7.91-7.86 (1H, m), 7.76-7.72 (2H, m), 7.55 (1H, s), 7.11-7.06 ( 2H, m), 6.88-6.83 (1H, m), 2.16 (3H, s), 1.86-1.71 (1H, m), 0.75-0.56 (4H, m).
Physical properties: candy-like.

(Example 508)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-benzylbenzoate (Compound No. 2826)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.22-8.18 (1H, d, J = 7.2 Hz), 7.62-7.54 (1H, t, J = 7.6 Hz), 7.44-7.06 (10H, m), 6.85 -6.81 (1H, m), 4.46 (1H, s), 2.11 (3H, s), 1.80-1.67 (1H, m), 0.75-0.64 (2H, m), 0.60-0.52 (2H, m).
Physical properties: Pasty.

(Example 509)
Bis [6-chloro-3- (2-methylphenoxy) -4-pyridazinyl] phthalate (Compound No. 2827)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.06 (2H, dd, J = 6.0, 3.4 Hz), 7.57 (2H, s), 7.25-7.15 (8H, m), 7.05-7.01 (2H, m) , 2.14 (6H, s).
Melting point (° C): 157-158.

(Example 510)
1- [6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] 2-methyl 1,2-piperidinedicarboxylate (Compound No. 3642)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.60 (0.5H, s), 7.59 (0.5H, s), 7.14-7.03 (2H, m), 6.92-6.80 (1H, m), 5.10-4.90 ( 1H, m), 4.32-4.06 (1H, m), 3.73 (1.5H, s), 3.71 (1.5H, s), 3.40-3.05 (1H, m), 2.43-2.20 (1H, m), 2.15 ( 1.5H, s), 2.13 (1.5H, s), 2.00-1.20 (6H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 511)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-nitrobenzoate (Compound No. 2850)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.15-8.05 (1H, m), 7.95-7.72 (3H, m), 7.65 (1H, s), 7.14-7.05 (2H, m), 6.90-6.80 ( 1H, m), 2.15 (3H, s), 1.85-1.70 (1H, m), 0.78-0.65 (2H, m), 0.65-0.50 (2H, m).
Physical property: Oily substance.

(Example 512)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-phenoxybenzoate (Compound No. 2856)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 8.35 (1H, dd, J = 8.2, 1.8 Hz), 8.15 (1H, dd, J = 8.0, 1.8 Hz), 7.74 (1H, dt, J = 7.0, 1.4Hz), 7.61-7.21 (5H, m), 7.15-6.98 (4H, m), 6.84-6.79 (1H, m), 2.09 (3H, s), 1.80-1.68 (1H, m), 0.70-0.61 (2H, m), 0.59-0.51 (2H, m).
Physical properties: Pasty.

(Example 513)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-chlorobenzoate (Compound No. 2868)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.18 (1H, d, J = 1.8 Hz), 8.10 (1H, d, J = 8.1 Hz), 7.68 (1H, br.d, J = 9.2 Hz), 7.57 (1H, s), 7.50 (1H, t, J = 8.1Hz), 7.08 (1H, d, J = 5.8Hz), 7.07 (1H, d, J = 3.7Hz), 6.85 (1H, dd, J = 5.8, 3.7Hz), 2.15 (3H, s), 1.85-1.66 (1H, m), 0.80-0.50 (4H, m).
Physical properties: amorphous.

(Example 514)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-fluorobenzoate (Compound No. 2862)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 8.02 (1H, dd, J = 6.2, 1.5 Hz), 7.89 (1H, br.d, J = 8.8 Hz), 7.60-7.34 (2H, m), 7.59 (1H, s), 7.13-7.04 (2H, m), 6.90-6.78 (1H, m), 2.15 (3H, s), 1.83-1.68 (1H, m), 0.80-0.50 (4H, m).
Physical property: Oily substance.

(Example 515)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-bromobenzoate (Compound No. 2874)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.33 (1H, s), 8.14 (1H, d, J = 8.0Hz), 7.82 (1H, d, J = 8.0Hz), 7.56 (1H, s), 7.43 (1H, t, J = 8.0Hz), 7.13-7.03 (2H, m), 6.90-6.80 (1H, m), 2.15 (3H, s), 1.85-1.68 (1H, m), 0.80-0.50 ( 4H, m).
Physical properties: candy-like.

(Example 516)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-iodobenzoate (Compound No. 2880)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.54 (1H, d, J = 1.8 Hz), 8.20-8.15 (1H, m), 8.03 (1H, d, J = 8.1 Hz), 7.56 (1H, s ), 7.34-7.26 (1H, m), 7.13-7.05 (2H, m), 6.89-6.82 (1H, m), 2.15 (3H, s), 1.83-1.71 (1H, m), 0.80-0.68 (2H , m), 0.65-0.52 (2H, m).
Physical properties: amorphous.

(Example 517)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3- (trifluoromethyl) benzoate (Compound No. 2900)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.47 (1H, s), 8.41 (1H, d, J = 7.7Hz), 7.96 (1H, d, J = 7.3Hz), 7.75-7.67 (1H, m ), 7.58 (1H, s), 7.12-7.06 (2H, m), 6.89-6.82 (1H, m), 2.16 (3H, s), 1.84-1.71 (1H, m), 0.80-0.53 (4H, m ).
Physical properties: candy-like.

(Example 518)
Bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] isophthalate (Compound No. 2906)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 9.02 (1H, s), 8.53 (2H, d, J = 8.2Hz), 7.78 (1H, t, J = 7.8Hz), 7.58 (2H, s), 7.08-7.06 (4H, m), 6.86-6.82 (2H, m), 2.14 (6H, s), 1.83-1.68 (2H, m), 0.78-0.69 (4H, m), 0.60-0.53 (4H, m ).
Physical properties: Pasty.

(Example 519)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-nitrobenzoate (Compound No. 2918)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 9.05-9.04 (1H, m), 8.59-8.52 (2H, m), 7.79 (1H, t, J = 7.7Hz), 7.59 (1H, s), 7.13 -7.07 (2H, m), 6.89-6.82 (1H, m), 2.15 (3H, s), 1.83-1.72 (1H, m), 0.80-0.54 (4H, m).
Physical properties: candy-like.

(Example 520)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-phenoxybenzoate (Compound No. 2924)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.95-7.90 (1H, m), 7.80-7.78 (1H, m), 7.57 (1H, s), 7.50 (1H, t, J = 8.0Hz), 7.40 -7.30 (3H, m), 7.17-7.10 (1H, m), 7.09-7.03 (3H, m), 7.07 (1H, s), 6.87-6.82 (1H, m), 2.13 (3H, s), 1.81 -1.67 (1H, m), 0.78-0.66 (2H, m). 0.59-0.54 (2H, m).
Physical properties: Pasty.

(Example 521)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-fluorobenzoate (Compound No. 2930)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.30-8.18 (2H. M), 7.59 (1H, s), 7.30-7.15 (2H, m), 7.15-7.02 (2H, m), 6.90-6.78 ( 1H, m), 2.15 (3H, s), 1.85-1.70 (1H, m), 0.80-0.50 (4H, m). 398 (M +), 370, 335, 275.
Physical properties: candy-like.

(Example 522)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-ethylbenzoate (Compound No. 2961)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.13 (2H, d, J = 8.5 Hz), 7.60 (1H, s), 7.36 (2H, d, J = 8.5 Hz), 7.12-7.04 (2H, m ), 6.88-6.81 (1H, m), 2.75 (2H, q, J = 7.6 Hz), 2.04 (3H, s), 1.85-1.71 (1H, m), 1.28 (3H, t, J = 7.6 Hz) , 0.79-0.65 (2H, m), 0.61-0.52 (2H, m).
Physical properties: Pasty.

(Example 523)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-propylbenzoate (Compound No. 2970)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.12 (2H, d, J = 8.4 Hz), 7.59 (1H, s), 7.34 (2H, d, J = 8.4 Hz), 7.12-7.05 (2H, m ), 6.88-6.81 (1H, m), 2.69 (2H, t, J = 7.3 Hz), 2.16 (3H, s), 1.85-1.60 (3H, m), 0.96 (3H, t, J = 7.3 Hz) , 0.80-0.68 (2H, m), 0.63-0.52 (2H, m).
Physical properties: Pasty.

(Example 524)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-isopropylbenzoate (Compound No. 2976)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.14 (2H, d, J = 8.4 Hz), 7.59 (1H, s), 7.40 (2H, d, J = 8.4 Hz), 7.12-7.05 (2H, m ), 6.90-6.82 (1H, m), 3.01 (1H, septet, J = 7.0 Hz), 2.15 (3H, s), 1.85-1.70 (1H, m), 1.29 (6H, d, J = 7.0 Hz) , 0.80-0.65 (2H, m), 0.63-0.52 (2H, m).
Physical properties: Pasty.

(Example 525)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-butylbenzoate (Compound No. 2982)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.12 (2H, d, J = 8.1 Hz), 7.59 (1H, s), 7.35 (2H, d, J = 8.1 Hz), 7.12-7.03 (2H, m ), 6.89-6.81 (1H, m), 2.72 (2H, t, J = 7.3 Hz), 2.16 (3H, s), 1.85-1.57 (3H, m), 1.47-1.22 (2H, m), 0.94 ( 3H, t, J = 7.3 Hz), 0.80-0.68 (2H, m), 0.65-0.55 (2H, m).
Physical properties: Pasty.

(Example 526)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (trifluoromethyl) benzoate (Compound No. 2988)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.34 (2H, d, J = 8.8Hz), 7.83 (2H, d, J = 8.8Hz), 7.60 (1H, s), 7.14-7.07 (2H, m ), 6.89-6.83 (1H, m), 2.15 (3H, s), 1.83-1.72 (1H, m), 0.79-0.71 (2H, m), 0.63-0.54 (2H, m).
Melting point (° C): 127-128.

(Example 527)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-cyanobenzoate (Compound No. 2994)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.33 (2H, d, J = 8.8Hz), 7.86 (2H, d, J = 8.8Hz), 7.60 (1H, s), 7.14-7.07 (2H, m ), 6.89-6.83 (1H, m), 2.14 (3H, s), 1.82-1.68 (1H, m), 0.79-0.53 (4H, m).
Physical properties: candy-like.

(Example 528)
Bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] terephthalate (Compound No. 3001)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.39 (4H, s), 7.62 (2H, s), 7.10-7.07 (4H, m), 6.87-6.83 (2H, m), 2.15 (6H, s) , 1.81-1.68 (2H, m), 0.78-0.70 (4H, m), 0.61-0.53 (4H, m).
Melting point (° C): 247-249.

(Example 529)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl [1,1'-biphenyl] -4-carboxylate (Compound No. 3016)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.31-8.23 (2H, m), 7.79-7.74 (2H, m), 7.67-7.62 (3H, m), 7.54-7.42 (3H, m), 7.09- 7.06 (2H, m), 6.87-6.82 (1H, m), 2.17 (3H, s), 1.84-1.75 (1H, m), 0.77-0.56 (4H, m).
Melting point (° C): 135-137.

(Example 530)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (trifluoromethoxy) benzoate (Compound No. 3022)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.28 (2H, d, J = 9.2Hz), 7.59 (1H, s), 7.38 (2H, d, J = 9.2Hz), 7.14-7.04 (2H, m ), 6.89-6.82 (1H, m), 2.15 (3H, s), 1.83-1.69 (1H, m), 0.78-0.65 (2H, m), 0.62-0.53 (2H, m).
Physical properties: Pasty.

(Example 531)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (benzyloxy) benzoate (Compound No. 3028)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.16 (2H, d, J = 9.2 Hz), 7.60 (1H, s), 7.50-7.30 (5H, m), 7.10-7.03 (4H, m), 6.89 -6.82 (1H, m), 5.17 (2H, s), 2.15 (3H, s), 1.85-1.72 (1H, m), 0.80-0.68 (2H, m), 0.65-0.53 (2H, m).
Physical properties: Pasty.

(Example 532)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,3-difluorobenzoate (Compound No. 3034)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.93-7.85 (1H, m), 7.57 (1H, s), 7.57-7.44 (1H, m), 7.32-7.21 (1H, m), 7.10-7.05 ( 2H, m), 6.87-6.82 (1H, m), 2.15 (3H, s), 1.81-1.73 (1H, m), 0.76-0.72 (2H, m), 0.60-0.56 (2H, m).
Physical properties: Pasty.

(Example 533)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-fluoro-3- (trifluoromethyl) benzoate (Compound No. 3040)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.36-8.28 (1H, m), 7.99-7.92 (1H, m), 7.56 (1H, s), 7.49-7.41 (1H, m), 7.13-7.05 ( 2H, m), 6.89-6.83 (1H, m), 2.15 (3H, s), 1.84-1.72 (1H, m), 0.80-0.54 (4H, m).
Physical properties: amorphous.

(Example 534)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,3-dimethylbenzoate (Compound No. 3046)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.00-7.96 (1H, m), 7.54 (1H, s), 7.45-7.41 (1H, m), 7.27-7.20 (1H, m), 7.14-7.05 ( 2H, m), 6.89-6.82 (1H, m), 2.57 (3H, s), 2.37 (3H, s), 2.16 (3H, s), 1.86-1.72 (1H, m), 0.79-0.69 (2H, m), 0.61-0.53 (2H, m).
Physical properties: Pasty.

(Example 535)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-chloro-2-methylbenzoate (Compound No. 3052)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.04 (1H, d, J = 8.1 Hz), 7.65 (1H, d, J = 8.1 Hz), 7.54 (1H, s), 7.33-7.25 (1H, m ), 7.13-7.06 (2H, m), 6.89-6.83 (1H, m), 2.73 (3H, s), 2.15 (3H, s), 1.83-1.71 (1H, m), 0.79-0.68 (2H, m ), 0.65-0.53 (2H, m).
Physical properties: amorphous.

(Example 536)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,4-difluorobenzoate (Compound No. 3058)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.23-8.12 (1H, m), 7.56 (1H, s), 7.10-6.94 (4H, m), 6.87-6.82 (1H, m), 2.15 (3H, s), 1.81-1.73 (1H, m), 0.75-0.56 (4H, m).
Physical properties: amorphous.

(Example 537)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-chloro-2-fluorobenzoate (Compound No. 3064)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.07 (1H, dd, J = 7.4Hz, 8.5Hz), 7.55 (1H, s), 7.38-7.22 (2H, m), 7.14-7.03 (2H, m ), 6.90-6.78 (1H, m), 2.15 (3H, s), 1.85-1.68 (1H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 538)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-fluoro-4- (trifluoromethyl) benzoate (Compound No. 3070)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.30-8.22 (1H, m), 7.61-7.52 (2H, m), 7.57 (1H, s), 7.14-7.05 (2H, m), 6.87-6.82 ( 1H, m), 2.15 (3H, m), 1.83-1.69 (1H, m), 0.78-0.70 (2H, m), 0.65-0.55 (2H, m).
Physical properties: Pasty.

(Example 539)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-chloro-4-fluorobenzoate (Compound No. 3076)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.25-8.18 (1H, m), 7.57 (1H, s), 7.34-7.29 (1H, m), 7.19-7.05 (3H, m), 6.89-6.82 ( 1H, m), 2.15 (3H, m), 1.84-1.70 (1H, m), 0.79-0.68 (2H, m), 0.64-0.53 (2H, m).
Physical properties: Pasty.

(Example 540)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-bromo-2-chlorobenzoate (Compound No. 3082)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.01 (1H, d, J = 8.4Hz), 7.76 (1H, d, J = 1.8Hz), 7.60-7.55 (2H, m), 7.10-7.07 (2H m), 6.87-6.83 (1H, m), 2.15 (3H, s), 1.83-1.71 (1H, m), 0.77-0.71 (2H, m), 0.62-0.56 (2H, m).
Physical properties: Pasty.

(Example 541)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-bromo-2-methylbenzoate (Compound No. 3088)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.05 (1H, d, J = 8.4 Hz), 7.56-7.48 (3H, m), 7.09-7.07 (2H, m), 6.86-6.82 (1H, m) , 2.14 (3H, s), 2.04 (3H, s), 1.85-1.72 (1H, m), 0.79-0.71 (2H, m), 0.64-0.55 (2H, m).
Physical properties: Pasty.

(Example 542)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,4-dimethylbenzoate (Compound No. 3094)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.11 (1H, d, J = 8.9 Hz), 7.57 (1H, s), 7.16-7.13 (2H, m), 7.09-7.05 (2H, m), 6.88 -6.81 (1H, m), 2.65 (3H, s), 2.41 (3H, s), 2.15 (3H, s), 1.85-1.71 (1H, m), 0.80-0.68 (2H, m), 0.67-0.55 (2H, m).
Physical properties: Pasty.

(Example 543)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,5-dichlorobenzoate (Compound No. 3100)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.10 (1H, d, J = 2.2Hz), 7.60-7.45 (3H, m), 7.15-7.04 (2H, m), 6.90-6.78 (1H, m) , 2.15 (3H, s), 1.85-1.70 (1H, m), 0.80-0.50 (4H, m).
Melting point (° C): 128-130.

(Example 544)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5-bromo-2-chlorobenzoate (Compound No. 3106)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.20 (1H, d, J = 2.2 Hz), 7.68 (1H, dd, J = 2.2 Hz, 8.4 Hz), 7.54 (1H, s), 7.43 (1H, d, J = 8.4Hz), 7.14-7.03 (2H, m), 6.92-6.80 (1H, m), 2.15 (3H, s), 1.87-1.70 (1H, m), 0.85-0.50 (4H, m) .
Physical properties: candy-like.

(Example 545)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-bromo-5-methoxybenzoate (Compound No. 3112)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.67-7.57 (3H, m), 7.12-7.00 (3H, m), 6.87-6.82 (1H, m), 3.85 (3H, s), 2.16 (3H, s), 1.87-1.75 (1H, m), 0.80-0.68 (2H, m), 0.65-0.55 (2H, m).
Physical properties: Pasty.

(Example 546)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,5-dimethylbenzoate (Compound No. 3129)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.99 (1H, s), 7.54 (1H, s), 7.37-7.30 (1H, m), 7.25-7.21 (1H, m), 7.13-7.05 (2H, m), 6.89-6.82 (1H, m), 2.63 (3H, s), 2.40 (3H, s), 2.16 (3H, s), 1.86-1.72 (1H, m), 0.80-0.70 (2H, m) , 0.62-0.54 (2H, m).
Physical property: Oily substance.

(Example 547)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,6-difluorobenzoate (Compound No. 3138)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.68-7.50 (2H, m), 7.15-7.00 (4H, m), 6.90-6.77 (1H, m), 2.15 (3H, s), 1.90-1.70 ( 1H, m), 0.85-0.50 (4H, m).
Physical properties: candy-like.

(Example 548)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-chloro-6-fluorobenzoate (Compound No. 3144)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.57-7.00 (5H, m), 6.90-6.78 (1H, m), 2.16 (3H, s), 1.90-1.75 (1H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 549)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,6-dichlorobenzoate (Compound No. 3150)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.58 (1H, s), 7.43-7.41 (3H, m), 7.11-7.08 (2H, m), 6.88-6.83 (1H, m), 2.17 (3H, s), 1.85-1.77 (1H, m), 0.74-0.56 (4H, m).
Physical properties: amorphous.

(Example 550)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,6-dimethylbenzoate (Compound No. 3156)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 7.48 (1H, s), 7.32 (1H, dd, J = 8.4, 7.0 Hz), 7.15-7.07 (3H, m), 6.87-6.83 (1H, m) , 2.53 (6H, s), 2.16 (3H, s), 1.84-1.76 (1H, m), 0.75-0.69 (2H, m), 0.62-0.57 (2H, m).
Physical properties: Pasty.

(Example 551)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,6-dimethoxybenzoate (Compound No. 3162)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.59 (1H, s), 7.39 (1H, t, J = 8.8Hz), 7.09-7.07 (2H, m), 6.85-6.81 (1H, m), 6.62 (2H, d, J = 6.6Hz), 3.84 (6H, s), 2.17 (3H, s), 1.96-1.81 (1H, m), 0.74-0.55 (4H, m).
Melting point (° C): 127-128.

(Example 552)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,4-difluorobenzoate (Compound No. 3168)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.10-7.99 (2H, m), 7.58 (1H, s), 7.43-7.25 (1H, m), 7.15-7.02 (2H, m), 6.90-6.80 ( 1H, m), 2.15 (3H, s), 1.83-1.67 (1H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 553)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-fluoro-4-methylbenzoate (Compound No. 3185)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.90 (1H, d, J = 8.1 Hz), 7.83 (1H, d, J = 9.9 Hz), 7.59 (1H, s), 7.37 (1H, dd, J = 7.3Hz, 7.7Hz), 7.15-7.00 (2H, m), 6.90-6.78 (1H, m), 2.39 (3H, d, 1.5Hz), 2.15 (3H, s), 1.85-1.67 (1H, m ), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 554)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,4-dichlorobenzoate (Compound No. 3194)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.29 (1H, d, J = 1.8 Hz), 8.03 (1H, dd, J = 8.4, 2.2 Hz), 7.65 (1H, d, J = 8.4 Hz), 7.57 (1H, s), 7.15-7.02 (2H, m), 6.90-6.80 (1H, m), 2.15 (3H, s), 1.82-1.68 (1H, m), 0.78-0.47 (4H, m).
Physical properties: amorphous.

(Example 555)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-chloro-3-nitrobenzoate (Compound No. 3200)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.69 (1H, d, J = 1.8 Hz), 8.33 (1H, dd, J = 8.4, 1.8 Hz), 7.78 (1H, d, J = 8.4 Hz), 7.57 (1H, s), 7.10-7.05 (2H, m), 6.87-6.82 (1H, m), 2.14 (3H, s), 1.77-1.69 (1H, m), 0.75-0.56 (4H, m).
Physical properties: amorphous.

(Example 556)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,5-difluorobenzoate (Compound No. 3217)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.80-7.65 (2H, m), 7.58 (1H, s), 7.32-7.00 (3H, m), 6.90-6.80 (1H, m), 2.15 (3H, s), 1.85-1.65 (1H, m), 0.80-0.50 (4H, m).
Physical properties: amorphous.

(Example 557)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,5-dichlorobenzoate (Compound No. 3226)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.07 (2H, d, J = 2.0 Hz), 7.69 (1H, t, J = 2.0 Hz), 7.55 (1H, s), 7.13-7.00 (2H, m ), 6.89-6.82 (1H, m), 2.15 (3H, s), 1.83-1.60 (1H, m), 0.80-0.70 (2H, m), 0.63-0.55 (2H, m).
Melting point (° C): 168-174.

(Example 558)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,5-dimethylbenzoate (Compound No. 3243)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.82 (2H, s), 7.56 (1H, s), 7.32 (1H, s,), 7.13-7.04 (2H, m), 6.89-6.82 (1H, m ), 2.41 (6H, s), 2.16 (3H, s), 1.85-1.72 (1H, m), 0.80-0.70 (2H, m), 0.63-0.53 (2H, m).
Melting point (° C): 117-119.

(Example 559)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,5-dimethoxybenzoate (Compound No. 3252)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.34 (1H, s), 7.33 (1H, s), 7.08-7.06 (2H, m), 6.87-6.82 (1H, m) , 6.78-6.75 (1H, m), 3.86 (6H, s), 2.16 (3H, s), 1.86-1.72 (1H, m), 0.80-0.72 (2H, m), 0.63-0.54 (2H, m) .
Physical properties: Pasty.

(Example 560)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,4,6-trichlorobenzoate (Compound No. 3258)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.46 (2H, s), 7.15-7.05 (2H, m), 6.90-6.82 (1H, m), 2.16 (3H, s) , 1.86-1.72 (1H, m), 0.78-0.67 (2H, m), 0.65-0.55 (2H, m).
Physical properties: Pasty.

(Example 561)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,4,5-trimethoxybenzoate (Compound No. 3264)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.45 (2H, s), 7.14-7.04 (2H, m), 6.89-6.83 (1H, m), 3.96 (3H, s) , 3.94 (6H, s), 2.16 (3H, s), 1.85-1.72 (1H, m), 0.80-0.67 (2H, m), 0.63-0.54 (2H, m).
Physical properties: amorphous.

(Example 562)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-naphthoate (Compound No. 3270)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 9.02 (1H, d, J = 8.4 Hz), 8.55 (1H, d, J = 7.3 Hz), 8.17 (1H, d, J = 8.0 Hz), 7.95 ( 1H, d, J = 8.0Hz), 7.75-7.54 (4H, m), 7.13-7.00 (2H, m), 6.90-6.80 (1H, m), 2.18 (3H, s), 1.93-1.75 (1H, m), 0.83-0.52 (4H, m).
Physical properties: amorphous.

(Example 563)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-naphthoate (Compound No. 3276)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.81 (1H, s), 8.18 (1H, dd, J = 1.5Hz, 8.5Hz), 8.05-7.87 (3H, m), 7.70-7.52 (3H, m ), 7.10-7.00 (2H, m), 6.90-6.77 (1H, m), 2.18 (3H, s), 1.90-1.73 (1H, m), 0.83-0.53 (4H, m).
Physical properties: amorphous.

(Example 564)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-methyl-1H-pyrrole-2-carboxylate (Compound No. 3282)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.25 (1H, s), 7.08-7.06 (2H, m), 6.96 (1H, s), 6.86-6.81 (1H, m) , 6.24-6.21 (1H, m), 3.97 (3H, s), 2.15 (3H, s), 1.87-1.72 (1H, m), 0.80-0.70 (2H, m), 0.63-0.52 (2H, m) .
Melting point (° C): 143-144.

(Example 565)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5-bromo-2-furoate (Compound No. 3288)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.53 (1H, s), 7.43 (1H, d, J = 3.7 Hz), 7.15-7.03 (2H, m), 6.90-6.78 (1H, m), 6.59 (1H, d, J = 3.7Hz), 2.15 (3H, s), 1.83-1.70 (1H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 566)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-furoate (Compound No. 3294)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.30 (1H, t, J = 0.7 Hz), 7.57-7.53 (1H, m), 7.55 (1H, s), 7.13-7.04 (2H, m), 6.92 -6.81 (2H, m), 2.15 (3H, s), 1.83-1.69 (1H, s), 0.80-0.53 (4H, m).
Physical properties: Pasty.

(Example 567)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5-tert-butyl-2-methyl-3-furoate (Compound No. 3300)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.09-7.07 (2H, m), 6.87-6.83 (1H, m), 6.33 (1H, s), 2.64 (3H, s) , 2.15 (3H, s), 1.78-1.73 (1H, m), 1.29 (9H, s), 0.75-0.57 (4H, m).
Physical properties: candy-like.

(Example 568)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5-methyl-2- (trifluoromethyl) -3-furoate (Compound No. 3306)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.53 (1H, s), 7.13-7.04 (2H, m), 6.89-6.82 (1H, m), 6.64 (1H, s), 2.42 (3H, s) , 2.13 (3H, s), 1.81-1.67 (1H, m), 0.78-0.68 (2H, m), 0.65-0.53 (2H, m).
Physical properties: Pasty.

(Example 569)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5- (4-chlorophenyl) -2- (trifluoromethyl) -3-furoate (Compound No. 3312)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.70-7.66 (2H, m), 7.56 (1H, s), 7.47-7.42 (2H, m), 7.19 (1H, s), 7.14-7.05 (2H, m), 6.90-6.82 (1H, m), 2.14 (3H, s), 1.83-1.69 (1H, m), 0.80-0.68 (2H, m), 0.65-0.53 (2H, m).
Physical properties: Pasty.

(Example 570)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-chloro-2-thiophenecarboxylate (Compound No. 3318)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.68 (1H, d, J = 5.5Hz), 7.58 (1H, s), 7.14 (1H, d, J = 5.5Hz), 7.11-7.03 (2H, m ), 6.90-6.80 (1H, m), 2.16 (3H, s), 1.85-1.70 (1H, m), 0.85-0.50 (4H, m).
Physical properties: candy-like.

(Example 571)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-methyl-2-thiophenecarboxylate (Compound No. 3324)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.65-7.55 (2H, m), 7.13-6.95 (3H, m), 6.90-6.80 (1H, m), 2.63 (3H, s), 2.16 (3H, s), 1.90-1.70 (1H, m), 0.85-0.50 (4H, m).
Physical properties: amorphous.

(Example 572)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-ethoxy-2-thiophenecarboxylate (Compound No. 3330)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.62 (1H, s), 7.59 (1H, d, J = 5.5Hz), 7.08-7.06 (2H, m), 6.90 (1H, d, J = 5.5Hz ), 6.86-6.81 (1H, m), 4.26 (2H, q, J = 7.0Hz), 2.17 (3H, s), 1.86-1.75 (1H, m), 1.46 (3H, t, J = 7.0Hz) , 0.75-0.55 (4H, m).
Physical properties: candy-like.

(Example 573)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5-chloro-2-thiophenecarboxylate (Compound No. 3336)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.86 (1H, d, J = 4.0 Hz), 7.57 (1H, s), 7.14-7.03 (3H, m), 6.90-6.83 (1H, m), 2.15 (3H, m), 1.83-1.68 (1H, m), 0.80-0.68 (2H, m), 0.65-0.53 (2H, m).
Physical properties: Pasty.

(Example 574)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5-bromo-2-thiophenecarboxylate (Compound No. 3342)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.80 (1H, d, J = 4.0Hz), 7.57 (1H, s), 7.19 (1H, d, J = 4.0Hz), 7.10-7.00 (2H, m ), 6.90-6.80 (1H, m), 2.15 (3H, s), 1.85-1.65 (1H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 575)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5-methyl-2-thiophenecarboxylate (Compound No. 3348)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.87 (1H, d, J = 3.7Hz), 7.57 (1H, s), 7.12-7.00 (2H, m), 6.93-6.87 (2H, m), 2.58 (3H, s), 2.15 (3H, s), 1.85-1.70 (1H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 576)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5-acetyl-2-thiophenecarboxylate (Compound No. 3354)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.02 (1H, d, J = 4.0 Hz), 7.72 (1H, d, J = 4.0 Hz), 7.58 (1H, s), 7.10-7.07 (2H, m ), 6.87-6.83 (1H, m), 2.63 (3H, s), 2.15 (3H, s), 1.79-1.71 (1H, m), 0.75-0.56 (4H, m).
Physical properties: amorphous.

(Example 577)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5-nitro-3-thiophenecarboxylate (Compound No. 3360)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.52 (1H, d, J = 1.8Hz), 8.43 (1H, d, J = 1.8Hz), 7.56 (1H, s), 7.13-7.05 (2H, m ), 6.90-6.80 (1H, m), 2.14 (3H, s), 1.85-1.65 (1H, m), 0.85-0.50 (4H, m).
Physical properties: amorphous.

(Example 578)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4,5-dibromo-2-thiophenecarboxylate (Compound No. 3366)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.84 (1H, s), 7.56 (1H, s), 7.14-7.05 (2H, m), 6.90-6.83 (1H, m), 2.14 (3H, s) , 1.83-1.69 (1H, m), 0.79-0.68 (2H, m), 0.65-0.55 (2H, m).
Physical properties: amorphous.

(Example 579)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-thiophenecarboxylate (Compound No. 3372)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.42-8.40 (1H, m), 7.70-7.66 (1H, m), 7.58 (1H, s), 7.47-7.41 (1H, m), 7.13-7.05 ( 2H, m), 6.88-6.82 (1H, m), 2.15 (3H, s), 1.84-1.70 (1H, m), 0.80-0.68 (2H, m), 0.64-0.55 (2H, m).
Physical properties: Pasty.

(Example 580)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-methoxy-3-thiophenecarboxylate (Compound No. 3378)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 8.33 (1H, d, J = 3.5 Hz), 7.59 (1H, s), 7.09-7.06 (2H, m), 6.87-6.82 (1H, m), 6.38 (1H, d, J = 3.5Hz), 3.93 (3H, s), 2.16 (3H, s), 1.82-1.74 (1H, m), 0.75-0.56 (4H, m).
Melting point (° C): 146-149.

(Example 581)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-benzyl-3-tert-butyl-1H-pyrazole-5-carboxylate (Compound No. 3384)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.44 (1H, s), 7.21 (5H, s), 7.09-7.06 (2H, m), 6.98 (1H, s), 6.85-6.80 (1H, m) , 5.72 (2H, s), 2.08 (3H, s), 1.76-1.64 (1H, m), 1.36 (9H, s), 0.75-0.64 (2H, m), 0.59-0.50 (2H, m).
Physical properties: Pasty.

(Example 582)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5-chloro-1,3-dimethyl-1H-pyrazole-4-carboxylate (Compound No. 3390)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.62 (1H, s), 7.09-7.07 (2H, m), 6.87-6.82 (1H, m), 3.86 (3H, s), 2.52 (3H, s) , 2.14 (3H, s), 1.84-1.77 (1H, m), 0.75-0.67 (2H, m), 0.60-0.53 (2H, m).
Physical properties: Pasty.

(Example 583)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3- (2-chlorophenyl) -5-methyl-4-isoxazolecarboxylate (Compound No. 3396)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.53 (1H, s), 7.48-7.42 (2H, m), 7.41-7.30 (2H, m), 7.08-7.06 (2H, m), 6.83-6.78 ( 1H, m), 2.89 (3H, s), 2.02 (3H, s), 1.67-1.53 (1H, m), 0.68-0.50 (4H, m).
Physical properties: amorphous.

(Example 584)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-methyl-1,2,3-thiadiazole-5-carboxylate (Compound No. 3402)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.15-7.05 (2H, m), 6.91-6.84 (1H, m), 3.08 (3H, s), 2.14 (3H, s) , 1.80-1.65 (1H, m), 0.80-0.72 (2H, m), 0.64-0.53 (2H, m).
Physical properties: Pasty.

(Example 585)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 6-methyl-2-pyridinecarboxylate (Compound No. 3408)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.12 (1H, d, J = 7.7Hz), 7.82 (1H, t, J = 7.7Hz), 7.55 (1H, s), 7.46 (1H, d, J = 7.7Hz), 7.12-7.02 (2H, m), 6.85-6.76 (1H, m), 2.71 (3H, s), 2.15 (3H, s), 1.87-1.74 (1H, m), 0.82-0.52 ( 4H, m).
Physical properties: candy-like.

(Example 586)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5-butyl-2-pyridinecarboxylate (Compound No. 3414)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.67 (1H, br.s), 8.22 (1H, d, J = 7.7Hz), 7.74 (1H, br.d, J = 7.7Hz), 7.53 (1H , s), 7.08-7.05 (2H, m), 6.83-6.78 (1H, m), 2.75 (2H, t, J = 7.7Hz), 2.15 (3H, s), 1.84-1.59 (3H, m), 1.48-1.32 (2H, m), 0.95 (3H, t, J = 7.0Hz), 0.75-0.54 (4H, m).
Physical properties: candy-like.

(Example 587)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl nicotinate (Compound No. 3420)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 9.42-9.41 (1H, m), 8.91 (1H, dd, J = 4.8, 0.8 Hz), 8.50-8.44 (1H, m), 7.60 (1H, s) , 7.56-7.49 (1H, m), 7.13-7.04 (2H, m), 6.88-6.78 (1H, m), 2.15 (3H, s), 1.90-1.70 (1H, m), 0.81-0.70 (2H, m), 0.63-0.55 (2H, m).
Physical properties: Pasty.

(Example 588)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-chloronicotinate (Compound No. 3426)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.66 (1H, dd, J = 4.8, 2.0Hz), 8.45 (1H, dd, J = 7.7, 2.0Hz), 7.59 (1H, s), 7.45 (1H , dd, J = 7.7, 4.8Hz), 7.14-7.06 (2H, m), 6.89-6.83 (1H, m), 2.15 (3H, s), 1.84-1.70 (1H, m), 0.80-0.52 (4H , m).
Physical properties: candy-like.

(Example 589)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-methylnicotinate (Compound No. 3432)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.74 (1H, dd, J = 4.8, 1.5 Hz), 8,46 (1H, dd, J = 7.7, 1.5 Hz), 7.58 (1H, s), 7.34 (1H, dd, J = 7.7, 4.8 Hz), 7.13-7.05 (2H, m), 6.89-6.83 (1H, m), 2.93 (3H, s), 2.15 (3H, s), 1.83-1.67 (1H m), 0.80-0.68 (2H, m), 0.65-0.55 (2H, m).
Physical properties: Pasty.

(Example 590)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-phenoxynicotinate (Compound No. 3438)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.50 (1H, dd, J = 7.8, 2.2 Hz), 8.39 (1H, dd, J = 4.8, 2.2 Hz), 7.61 (1H, s), 7.46-7.38 (2H, m), 7.29-7.20 (1H, m), 7.19-7.04 (5H, m), 6.86-6.81 (1H, m), 2.14 (3H, s), 1.85-1.72 (1H, m), 1.36 (9H, s), 0.75-0.65 (2H, m), 0.58-0.52 (2H, m).
Physical properties: Pasty.

(Example 591)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2- (methylsulfanyl) nicotinate (Compound No. 3444)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.70 (1H, dd, J = 4.9, 1.8 Hz), 8.47 (1H, dd, J = 7.7, 1.8 Hz), 7.63 (1H, s), 7.16 (1H , dd, J = 7.7, 4.8 Hz), 7.12-7.05 (2H, m), 6.89-6.82 (1H, m), 2.59 (3H, s), 2.16 (3H, s), 1.84-1.71 (1H, m ), 0.80-0.70 (2H, m), 0.65-0.53 (2H, m).
Physical properties: Pasty.

(Example 592)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2- (allylsulfanyl) nicotinate (Compound No. 3450)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.67 (1H, dd, J = 4.8, 1.8Hz), 8.46 (1H, dd, J = 8.2, 1.8Hz), 7.62 (1H, s), 7.16 (1H , dd, J = 8.2, 4.8Hz), 7.09-7.04 (2H, m), 6.89-6.82 (1H, m), 6.10-5.90 (1H, m), 5.33 (1H, dd, J = 16.8, 1.6Hz ), 5.12 (1H, dd, J = 11.0, 1.2Hz), 3.91 (1H, dd, J = 6.8, 1.2Hz), 2.15 (3H, s), 1.85-1.70 (1H, m), 0.78-0.71 ( 2H, m), 0.60-0.51 (2H, m).
Physical properties: Pasty.

(Example 593)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2- (phenylsulfanyl) nicotinate (Compound No. 3456)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.50 (1H, s), 8.47 (1H, d, J = 2.6Hz), 7.65 (1H, s), 7.59-7.51 (2H, m), 7.48-7.41 (3H, m), 7.17-7.05 (3H, m), 6.90-6.82 (1H, m), 2.18 (3H, s), 1.89-1.74 (1H, m), 0.82-0.70 (2H, m), 0.65 -0.54 (2H, m).
Physical properties: Pasty.

(Example 594)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (trifluoromethyl) nicotinate (Compound No. 3462)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 9.42 (1H, s), 9.08 (1H, d, J = 5.1 Hz), 7.79 (1H, d, J = 5.1 Hz), 7.57 (1H, s), 7.14-7.06 (2H, m), 6.90-6.84 (1H, m), 2.16 (3H, s), 1.84-1.72 (1H, m), 0.79-0.71 (2H, m), 0.63-0.55 (2H, m ).
Melting point (° C): 92-93.

(Example 595)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 6-chloronicotinate (Compound No. 3468)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 9.19 (1H, d, J = 2.0), 8.40 (1H, dd, J = 8.4, 2.6), 7.59 (1H, s), 7.54 (1H, d, J = 8.4Hz), 7.10-7.08 (1H, m), 7.07 (1H, s), 6.87-6.82 (1H, m), 2.14 (3H, s), 1.79-1.65 (1H, m), 0.79-0.70 ( 2H, m), 0.62-0.53 (2H, m).
Physical properties: Pasty.

(Example 596)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,6-dichloronicotinate (Compound No. 3474)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.46 (1H, d, J = 8.1 Hz), 7.67 (1H, s), 7.52 (1H, d, J = 8.1 Hz), 7.13-7.02 (2H, m ), 6.90-6.75 (1H, m), 2.14 (3H, s), 1.85-1.68 (1H, m), 0.85-0.48 (4H, m).
Physical properties: amorphous.

(Example 597)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-chloro-6-methylnicotinate (Compound No. 3480)
^{1 H-NMR (200MHz, CDCl} 3) δppm: 8.37 (1H, d, J = 7.7 Hz), 7.58 (1H, s), 7.27 (1H, d, J = 7.7 Hz), 7.14-7.08 (2H, m ), 6.89-6.80 (1H, m), 2.65 (3H, s), 2.15 (3H, s), 1.83-1.69 (1H, m), 0.80-0.70 (2H, m), 0.68-0.55 (2H, m ).
Physical properties: Pasty.

(Example 598)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 5,6-dichloronicotinate (Compound No. 3486)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 9.07 (1H, d, J = 2.2Hz), 8.50 (1H, d, J = 2.2Hz), 7.57 (1H, s), 7.10-7.07 (2H, m ), 6.87-6.82 (1H, m), 2.13 (3H, s), 1.80-1.65 (1H, m), 0.75-0.70 (2H, m), 0.58-0.55 (2H, m).
Physical properties: Pasty.

(Example 599)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-chloroisonicotinate (Compound No. 3492)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.68 (1H, d, J = 5.0 Hz), 8.05 (1H, s), 7.95-7.92 (1H, m), 7.57 (1H, s), 7.10-7.07 (2H, m), 6.87-6.83 (1H, m), 2.14 (3H, s), 1.77-1.68 (1H, m), 0.75-0.71 (2H, m), 0.58-0.56 (2H, m).
Physical properties: Pasty.

(Example 600)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-benzofuran-2-carboxylate (Compound No. 3498)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.86-7.75 (2H, m), 7.68-7.51 (3H, m), 7.38 (1H, dd, J = 7.7, 7.0 Hz), 7.12-7.05 (2H, m), 6.89-6.80 (1H, m), 2.17 (3H, s), 1.86-1.73 (1H, m), 0.80-0.68 (2H, m), 0.64-0.55 (2H, m).
Physical properties: amorphous.

(Example 601)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-benzothiophene-2-carboxylate (Compound No. 3504)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.34 (1H, s), 7.94 (2H, m), 7.64 (1H, s), 7.59-7.42 (2H, m), 7.09-7.07 (2H, m) , 6.87-6.83 (1H, m), 2.18 (3H, s), 1.88-1.72 (1H, m), 0.77-0.71 (2H, m), 0.61-0.53 (2H, m).
Melting point (° C): 105-107.

(Example 602)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1,3-benzothiazole-6-carboxylate (Compound No. 3510)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 9.24 (1H, s), 8.89 (1H, d, J = 1.4 Hz), 8.36 (1H, dd, J = 8.4, 1.4 Hz), 8.28 (1H, d , J = 8.4 Hz), 7.65 (1H, s), 7.09-7.06 (2H, m), 6.87-6.82 (1H, m), 2.17 (3H, s), 1.86-1.73 (1H, m), 0.78- 0.72 (2H, m), 0.63-0.55 (2H, m).
Physical properties: amorphous.

(Example 603)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1,3-benzodioxol-5-carboxylate (Compound No. 3516)
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 7.85 (1H, dd, J = 8.4, 1.8 Hz), 7.60-7.59 (2H, m), 7.09-7.06 (2H, m), 6.93 (1H, d, J = 8.0Hz), 6.86-6.82 (1H, m), 6.10 (2H, s), 2.15 (3H, s), 1.86-1.74 (1H, m), 0.79-0.70 (2H, m), 0.62-0.53 (2H, m).
Physical properties: Pasty.

(Example 604)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-isoquinolinecarboxylate (Compound No. 3522)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.45 (1H, d, J = 8.1 Hz), 7.78-7.70 (2H, m), 7.61-7.53 (2H, m), 7.16 (1H, d, J = 7.7 Hz), 7.12-7.05 (2H, m), 6.90-6.83 (1H, m), 6.66 (1H, d, J = 7.3 Hz), 2.15 (3H, s), 1.81-1.66 (1H, m), 0.79-0.67 (2H, m), 0.63-0.53 (2H, m).
Physical properties: amorphous.

(Example 605)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl tert-butyl (methyl) carbamate (Compound No. 3528)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.51 (1H, s), 7.15-7.03 (2H, m), 6.90-6.80 (1H, m), 3.11 (3H, s), 2.14 (3H, s) , 1.85-1.70 (1H, m), 1.47 (9H, s), 0.80-0.50 (4H, m).
Melting point (° C): 113-115.

(Example 606)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl dibutylcarbamate (Compound No. 3534)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.58 (1H, s), 7.15-7.03 (2H, m), 6.90-6.78 (1H, m), 3.50-3.26 (4H, m), 2.13 (3H, s), 1.87-1.50 (5H, m), 1.50-1.15 (4H, m), 1.10-0.85 (6H, m), 0.80-0.54 (4H, m).
Physical properties: candy-like.

(Example 607)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl benzyl (methyl) carbamate (Compound No. 3540)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.58 (0.5H, s), 7.57 (0.5H, s), 7.40-7.20 (5H, m), 7.15-7.03 (2H, m), 6.92-6.80 ( 1H, m), 4.68 (1H, s), 4.57 (1H, s), 3.08 (1.5H, s), 3.02 (1.5H, s), 2.15 (1.5H, s), 2.13 (1.5H, s) , 1.85-1.65 (1H, m), 0.80-0.45 (4H, m).
Physical properties: candy-like.

(Example 608)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl cyanomethyl (methyl) carbamate (Compound No. 3546)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.59 (0.4H, s), 7.56 (0.6H, s), 7.15-7.04 (2H, m), 6.90-6.80 (1H, m), 4.42 (0.8H , s), 4.36 (1.2H, s), 3.30 (1.8H, s), 3.19 (1.2H, s), 2.14 (3H, s), 1.85-1.62 (1H, m), 0.80-0.53 (4H, m).
Physical properties: candy-like.

(Example 609)
Ethyl N-({[6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] oxy} carbonyl) -N-methylglycinate (Compound No. 3552)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.61 (0.5H, s), 7.60 (0.5H, s), 7.15-7.02 (2H, m), 6.90-6.80 (1H, m), 4.28-4.11 ( 4H, m), 3.23 (1.5H, s), 3.13 (1.5H, s), 2.15 (1.5H, s), 2.13 (1.5H, s), 1.85-1.65 (1H, m), 1.31-1.18 ( 3H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 610)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl methyl (2-pyridinyl) carbamate (Compound No. 3558)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.35-8.25 (1H, m), 7.70-7.55 (1H, m), 7.05-6.90 (5H, m), 6.85-6.74 (1H, m), 3.56 ( 3H, s), 2.03 (3H, s), 1.72-1.55 (1H, m), 0.75-0.45 (4H, m).
Melting point (° C): 140-147.

(Example 611)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-piperidinecarboxylate (Compound No. 3636)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.56 (1H, s), 7.15-7.03 (2H, m), 6.90-6.80 (1H, m), 3.70-3.60 (2H, m), 3.60-3.45 ( 2H, m), 2.15 (3H, s), 1.86-1.70 (1H, m), 1.70-1.50 (6H, m), 0.80-0.53 (4H, m).
Physical properties: candy-like.

(Example 612)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl bis (2-chloroethyl) carbamate (Compound No. 3570)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.58 (1H, s), 7.15-7.05 (2H, m), 6.92-6.82 (1H, m), 3.98-3.70 (8H, m), 2.13 (3H, s), 1.82-1.65 (1H, m), 0.80-0.50 (4H, m).
Melting point (° C): 166-167.

(Example 613)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl diallylcarbamate (Compound No. 3576)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.56 (1H, s), 7.12-7.04 (2H, m), 6.88-6.80 (1H, m), 6.00-5.70 (2H, m), 5.30-5.15 ( 4H, m), 4.10-3.93 (4H, m), 2.13 (3H, s), 1.85-1.68 (1H, m), 0.80-0.52 (4H, m).
Physical properties: candy-like.

(Example 614)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl bis (cyanomethyl) carbamate (Compound No. 3582)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.59 (1H, s), 7.18-7.05 (2H, m), 6.90-6.80 (1H, m), 4.54 (2H, s), 4.48 (2H, s) , 2.13 (3H, s), 1.80-1.65 (1H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 615)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl bis (2-cyanoethyl) carbamate (Compound No. 3588)
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.61 (1H, s), 7.18-7.05 (2H, m), 6.92-6.82 (1H, m), 3.91 (2H, t, J = 6.6Hz), 3.77 (2H, t, J = 6.2Hz), 2.85 (2H, t, J = 6.6Hz), 2.78 (2H, t, J = 6.2Hz), 2.13 (3H, s), 1.80-1.63 (1H, m) , 0.82-0.53 (4H, m).
Melting point (° C): 159-161.

(Example 616)
Ethyl N-({[6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] oxy} carbonyl) -N- (2-ethoxy-2-oxoethyl) glycinate (Compound No. 3594)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.65 (1H, s), 7.13-7.03 (2H, m), 6.90-6.80 (1H, m), 4.33-4.05 (8H, m), 2.12 (3H, s), 1.83-1.65 (1H, m), 1.28 (3H, t, J = 7.3Hz), 1.19 (3H, t, J = 7.3Hz), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 617)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl bis (2-methoxyethyl) carbamate (Compound No. 3600)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.59 (1H, s), 7.15-7.05 (2H, m), 6.90-6.80 (1H, m), 3.80-3.50 (8H, m), 3.32 (6H, s), 2.15 (3H, s), 1.86-1.69 (1H, m), 0.80-0.52 (4H, m).
Physical properties: candy-like.

(Example 618)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl bis (2-ethoxyethyl) carbamate (Compound No. 3606)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.15-7.03 (2H, m), 6.90-6.80 (1H, m), 3.78-3.55 (8H, m), 3.46 (4H, q, J = 6.9Hz), 2.14 (3H, s), 1.87-1.65 (1H, m), 1.15 (3H, t, J = 6.9Hz), 1.14 (3H, t, J = 6.9Hz), 0.80- 0.53 (4H, m).
Physical properties: candy-like.

(Example 619)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-azetidine carboxylate (Compound No. 3612)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.53 (1H, s), 7.13-7.02 (2H, m), 6.90-6.78 (1H, m), 4.38-4.05 (4H, m), 2.45-2.29 ( 2H, m), 2.15 (3H, s), 1.85-1.67 (1H, m), 0.80-0.50 (4H, m).
Melting point (° C): 134-136.

(Example 620)
1- [6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] 2-methyl 1,2-pyrrolidine dicarboxylate (Compound No. 3618)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.65 (0.5H, s), 7.62 (0.5H, s), 7.15-7.02 (2H, m), 6.90-6.78 (1H, m), 4.63-4.57 ( 0.5H, m), 4.51-4.44 (0.5H, m), 3.91-3.55 (2H, m), 3.75 (1.5H, s), 3.65 (1.5H, s), 2.50-1.90 (4H, m), 2.15 (1.5H, s), 2.13 (1.5H, s), 1.90-1.69 (1H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 621)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-hydroxy-1-pyrrolidinecarboxylate (Compound No. 3624)
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.60 (1H, s), 7.13-7.03 (2H, m), 6.90-6.80 (1H, m), 4.65-4.52 (1H, m), 3.85-3.55 ( 4H, m), 2.14 (3H, s), 2.13-2.00 (2H, m), 1.87-1.70 (2H, m), 0.80-0.50 (4H, m).
Physical properties: candy-like.

(Example 622)
6-Chloro-3- (2-cyclopropyl-3,5,6-trimethylphenoxy) -4-pyridazinol (Compound No. 1126)
(1) 2,3,5-trimethylphenyl acetate
15.09 g (0.1108 mol) of 2,3,5-trimethylphenol was dissolved in dichloromethane (150 mL), 17.82 mL (0.2204 mol) of pyridine and then 20.78 mL (0.2202 mol) of acetic anhydride were added, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane: ethyl acetate, gradient) to give 20.08 g (0.1127 mol, quantitative yield) of 2,3,5-trimethylphenyl acetate. )Obtained.
(2) 1- (2-Hydroxy-3,4,6-trimethylphenyl) ethanone 13.83 g (77.60 mmol) of 2,3,5-trimethylphenyl acetate obtained in (1) was stirred under ice-cooling. While adding 20.69 g (155.2 mmol) of aluminum chloride, a little was added. The mixture was stirred overnight while heating to 100 ° C. After allowing to cool, the reaction mixture was added little by little to ice water. This mixture was extracted with dichloromethane, and the organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane: ethyl acetate, gradient) to give 12.75 g of 1- (2-hydroxy-3,4,6-trimethylphenyl) ethanone. (71.55 mmol, yield 92.20%) was obtained.
(3) 1- (2-Methoxy-3,4,6-trimethylphenyl) ethanone 8.00 g (44.9 mmol) of 1- (2-hydroxy-3,4,6-trimethylphenyl) ethanone obtained from (2) Was dissolved in acetone (100 mL), potassium carbonate (18.6 g, 135 mmol) and methyl iodide (8.40 mL, 135 mmol) were added, and the mixture was heated to reflux for 27 hours and 30 minutes. Further, 18.6 g (135 mmol) of potassium carbonate and 8.40 mL (135 mmol) of methyl iodide were added, and the mixture was heated to reflux for 6 hours. The reaction mixture was concentrated under reduced pressure, water (100 mL) was added to the residue, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Daisogel 1001W, hexane: ethyl acetate, gradient) to obtain 8.04 g (41.9%) of 1- (2-methoxy-3,4,6-trimethylphenyl) ethanone. Mmol, yield 93.3%).
(4) 1- (2-methoxy-3,4,6-trimethylphenyl) ethanol 1- (2-methoxy-3,4,6-trimethylphenyl) ethanone obtained in (3) 5.01 g (26.1 mmol) Was dissolved in methanol (100 mL), and 1.00 g (26.5 mmol) of sodium borohydride was added under ice cooling, followed by stirring for 2 hours 30 minutes under ice cooling. The reaction mixture was poured into 400 mL of ice water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 4.35 g (22.4 mmol, yield 85.8%) of 1- (2-methoxy-3,4,6-trimethylphenyl) ethanol.
(5) 2- (1-Chloroethyl) -3-methoxy-1,4,5-trimethylbenzene 0.652 g of 1- (2-methoxy-3,4,6-trimethylphenyl) ethanol obtained from (4) While stirring, 0.150 mL (1.72 mmol) of oxalyl chloride was added dropwise and stirred at 100 ° C. for 2 hours. Next, dichloromethane (1 mL) and triethylamine (3 mL) were added to the reaction mixture, and the mixture was stirred at 100 ° C. for 3 hours. The reaction mixture was poured into 60 ml of ice water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 0.620 g (2.91 mmol, yield 86.6%) of 2- (1-chloroethyl) -3-methoxy-1,4,5-trimethylbenzene.
(6) 3-methoxy-1,2,5-trimethyl-4-vinylbenzene
Dissolve 0.620 g (2.91 mmol) of 2- (1-chloroethyl) -3-methoxy-1,4,5-trimethylbenzene obtained in (5) in N, N-dimethylformamide (DMF, 6 mL). Potassium 1.20 g (8.70 mmol) was added and heated to reflux for 9 hours. The reaction mixture was poured into 50 ml of ice water and extracted with hexane. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Daisogel 1001W, hexane: ethyl acetate, gradient) to give 0.360 g (2.05 mmol) of 3-methoxy-1,2,5-trimethyl-4-vinylbenzene. Yield 70.4%).
(7) 2-Cyclopropyl-3-methoxy-1,4,5-trimethylbenzene Add 3.07 mL (3.04 mmol) of diethylzinc (0.99 mol / L hexane solution) to dry dichloromethane (5 mL) and stir under ice cooling. Then, a solution of 0.23 mL (3.0 mmol) of trifluoroacetic acid in dichloromethane (2.5 mL) was slowly added dropwise. After completion of the addition, the mixture was stirred for 30 minutes under ice cooling, and 0.24 mL (3.0 mmol) of diiodomethane was added dropwise. Next, a solution of 0.268 g (1.52 mmol) of 3-methoxy-1,2,5-trimethyl-4-vinylbenzene obtained in (6) in dichloromethane (3 mL) was added dropwise and stirred for 1 hour under ice-cooling. The reaction mixture was poured into water, acidified with dilute hydrochloric acid, and extracted with dichloromethane. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05717, 2 plates used, developed with hexane: ethyl acetate = 25: 1), and 2-cyclopropyl- 0.212 g (1.12 mmol, yield 73.7%) of 3-methoxy-1,4,5-trimethylbenzene was obtained.
(8) 2-Cyclopropyl-3,5,6-trimethylphenol Under a nitrogen atmosphere, 134 mg (3.35 mmol) of 60% sodium hydride was suspended in dry N, N-dimethylformamide (5 mL). Ethanethiol 0.26 mL (3.5 mmol) was slowly added dropwise. After stirring for 30 minutes, a solution of 0.212 g (1.12 mmol) of 2-cyclopropyl-3-methoxy-1,4,5-trimethylbenzene obtained in (7) in dry N, N-dimethylformamide (5 mL) was added dropwise. The mixture was heated and stirred at 160 ° C. for 5 hours. After cooling, the reaction mixture was poured into water, acidified with dilute hydrochloric acid, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed with ethyl acetate: hexane = 25: 1), and 2-cyclopropyl- 179 mg (1.02 mmol, yield 91.1%) of 3,5,6-trimethylphenol was obtained.
(9) 6-chloro-3- (2-cyclopropyl-3,5,6-trimethylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-cyclopropyl-3,5,6-trimethylphenoxy) Pyridazine 1-oxide mixture (step B-2)
2-Cyclopropyl-3,5,6-trimethylphenol 179 mg (1.02 mmol), 1,4-dioxane (5 mL) and dimethyl sulfoxide (5 mL) were mixed, and potassium tert-butoxide 125 mg (1.12 mmol) was added to the mixture. Added and stirred for 10 minutes. To this mixture, 167 mg (1.01 mmol) of 3,6-dichloropyridazine 1-oxide was added and allowed to stand at room temperature for 3 days. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05717, 2 plates used, developed with hexane: ethyl acetate = 2: 1), and 6-chloro-3 263 mg of a mixture of 2- (2-cyclopropyl-3,5,6-trimethylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-cyclopropyl-3,5,6-trimethylphenoxy) pyridazine 1-oxide Obtained.
(10) 4,6-Dichloro-3- (2-cyclopropyl-3,5,6-trimethylphenoxy) pyridazine (Step B-3)
6-Chloro-3- (2-cyclopropyl-3,5,6-trimethylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-cyclopropyl-3,5,6) obtained by (9) -Trimethylphenoxy) pyridazine 1-oxide mixture (263 mg) and phosphorus oxychloride (3.0 mL, 32 mmol) were mixed and stirred overnight at room temperature. Dichloromethane and water were added to the reaction mixture, and the mixture was stirred and extracted with dichloromethane. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05717, 2 plates used, developed with hexane: ethyl acetate = 2: 1), and 4,6-dichloro 198 mg (0.613 mmol, 60.7% yield from 3,6-dichloropyridazine 1-oxide) of 3- (2-cyclopropyl-3,5,6-trimethylphenoxy) pyridazine was obtained. 43.8 mg of 3-chloro-6- (2-cyclopropyl-3,5,6-trimethylphenoxy) pyridazine 1-oxide (0.144 mmol, 14.2% yield from 3,6-dichloropyridazine 1-oxide) Obtained.
(11) 6-chloro-3- (2-cyclopropyl-3,5,6-trimethylphenoxy) -4-pyridazinol (Compound No. 1126, Steps A-3 and A-4)
198 mg (0.613 mmol) of 4,6-dichloro-3- (2-cyclopropyl-3,5,6-trimethylphenoxy) pyridazine obtained in (10) was dissolved in dimethyl sulfoxide (10 mL), and 251 mg of sodium acetate ( 3.06 mmol) was added and the mixture was stirred at 120 ° C. for 4 hours. The reaction mixture was cooled, poured into water and acidified with dilute hydrochloric acid. This mixture was extracted with ethyl acetate, and the organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05717, 2 plates used, developed with hexane: ethyl acetate = 1: 2), and 6-chloro-3 116 mg (0.380 mmol, yield 62.0%) of-(2-cyclopropyl-3,5,6-trimethylphenoxy) -4-pyridazinol (Compound 1126) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 6.67 (1H, s), 6.62 (1H, s), 2.22 (3H, s), 2.16 (3H, s), 2.05 (3H, s), 1.85- 1.65 (1H, m), 0.75-0.62 (2H, m), 0.60-0.45 (2H, m).
Melting point (° C): 212-219.

(Example 623)
6-Chloro-3- (2-methoxy-3,5,6-trimethylphenoxy) -4-pyridazinol (Compound No. 1128)
(1) 1- [2- (Benzyloxy) -3,4,6-trimethylphenyl] ethanone 1- (2-hydroxy-3,4,6-trimethylphenyl) ethanone obtained in Example 622 (2) 2.00 g (11.2 mmol) was dissolved in N, N-dimethylformamide (8 mL). To this solution, 0.488 g (11.2 mmol) of 60% sodium hydride was added under ice-cooling, and the mixture was stirred as it was for 10 minutes under ice-cooling. Then, 1.92 g (11.2 mmol) of benzyl bromide was slowly added dropwise, and the mixture was stirred at room temperature. Stir overnight. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 1- [2- (benzyloxy) -3,4,6-trimethyl. 2.36 g (8.81 mmol, 78.7% yield) of phenyl] ethanone were obtained.
(2) 2- (benzyloxy) -3,4,6-trimethylphenyl acetate 500 mg (1.87 mmol) of 1- [2- (benzyloxy) -3,4,6-trimethylphenyl] ethanone obtained from (1) ) Was dissolved in dichloromethane (3 mL), a solution of 921 mg of m-chloroperbenzoic acid (purity 70-75%, 3.73-3.99 mmol) in dichloromethane (6 mL) was added, and the mixture was stirred at room temperature for 2 days. The reaction mixture was poured into a saturated aqueous sodium sulfite solution and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 560 mg of 2- (benzyloxy) -3,4,6-trimethylphenyl acetate.
(3) 2- (benzyloxy) -3,4,6-trimethylphenol 560 mg of 2- (benzyloxy) -3,4,6-trimethylphenyl acetate obtained in (2) was dissolved in ethanol (15 mL), 2N Aqueous sodium hydroxide solution was added, and the mixture was stirred at room temperature overnight and at 60 ° C. for 4 hours. The reaction mixture was cooled to room temperature and poured into water. The mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 290 mg of 2- (benzyloxy) -3,4,6-trimethylphenol. (1.20 mmol, 64.2% yield from 1- [2- (benzyloxy) -3,4,6-trimethylphenyl] ethanone).
(4) 3- (Benzyloxy) -2-methoxy-1,4,5-trimethylbenzene 2- (benzyloxy) -3,4,6-trimethylphenol 290 mg (1.20 mmol) obtained from (3) It was dissolved in acetone (3 mL), 350 mg (2.54 mmol) of potassium carbonate was added, and the mixture was stirred at room temperature for 15 minutes. Next, 0.180 mL (2.89 mmol) of methyl iodide was added, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (MERCK, 1.05744, 3 plates used, developed with ethyl acetate: hexane = 10: 1), and 3- (benzyloxy 196 mg (0.766 mmol, yield 63.8%) of 2-methoxy-1,4,5-trimethylbenzene was obtained.
(5) 2-methoxy-3,5,6-trimethylphenol 180 mg (0.703 mmol) of 3- (benzyloxy) -2-methoxy-1,4,5-trimethylbenzene obtained in (4) was added to methanol (3 mL ), 5% palladium-carbon (0.10 g) was added to the solution, and the mixture was stirred under a hydrogen atmosphere (1 atm) for 4 hours. The reaction mixture was filtered through celite and the filtrate was concentrated. 90.7 mg (0.546 mmol, yield 77.7%) of 2-methoxy-3,5,6-trimethylphenol was obtained.
(6) 6-chloro-3- (2-methoxy-3,5,6-trimethylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-methoxy-3,5,6-trimethylphenoxy) pyridazine 1 -Oxide mixture (step B-2)
2-Methoxy-3,5,6-trimethylphenol (90.0 mg, 0.542 mmol), 1,4-dioxane (1.5 mL) and dimethyl sulfoxide (1.5 mL) obtained in (5) were mixed. 73.5 mg (0.656 mmol) of tert-butoxide was added, and the mixture was stirred for 15 minutes under ice cooling. To this mixture, 93.2 mg (0.565 mmol) of 3,6-dichloropyridazine 1-oxide was added and stirred at room temperature for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed with hexane: ethyl acetate = 2: 1), and 6-chloro-3 140 mg of a mixture of 2- (2-methoxy-3,5,6-trimethylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-methoxy-3,5,6-trimethylphenoxy) pyridazine 1-oxide was obtained. .
(7) 4,6-Dichloro-3- (2-methoxy-3,5,6-trimethylphenoxy) pyridazine (Step B-3)
6-Chloro-3- (2-methoxy-3,5,6-trimethylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-methoxy-3,5,6-trimethyl) obtained by (6) 140 mg of a mixture of phenoxy) pyridazine 1-oxide and 0.25 mL (2.7 mmol) of phosphorus oxychloride were mixed and stirred overnight at room temperature. The reaction mixture was poured into water and extracted with dichloromethane. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed with hexane: ethyl acetate = 2: 1), and 4,6-dichloro 111 mg (0.355 mmol, yield 62.8% from 3,6-dichloropyridazine 1-oxide) of -3- (2-methoxy-3,5,6-trimethylphenoxy) pyridazine was obtained. In addition, 38.3 mg (0.130 mmol, 23.0% yield from 3,6-dichloropyridazine 1-oxide) of 3-chloro-6- (2-methoxy-3,5,6-trimethylphenoxy) pyridazine 1-oxide was obtained. It was.
(8) 6-chloro-3- (2-methoxy-3,5,6-trimethylphenoxy) -4-pyridazinol (Compound No. 1128, Step B-4)
2 mol / L sodium hydroxide was added to a solution of 4,6-dichloro-3- (2-methoxy-3,5,6-trimethylphenoxy) pyridazine obtained in (7) in 111 mg (0.355 mmol) of dimethyl sulfoxide (10 mL). 0.3 mL (0.6 mmol) of an aqueous solution was added, and the mixture was stirred at room temperature for 2 hours and 30 minutes. The reaction mixture was poured into an ice-cooled 1 mol / L aqueous sodium hydroxide solution and extracted with ethyl acetate. The aqueous layer was separated, acidified with concentrated hydrochloric acid under ice cooling, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off, the obtained residue was washed with ether, and 38.9 mg of 6-chloro-3- (2-methoxy-3,5,6-trimethylphenoxy) -4-pyridazinol (Compound No. 1128) ( 0.132 mmol, yield 37.2%).
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 6.73 (1H, s), 6.67 (1H, s), 3.69 (3H, s), 2.29 (3H, s), 2.15 (3H, s), 2.09 ( 3H, s).
Melting point (° C): 209-210.

(Example 624)
6-chloro-3- [2- (1-isopropylvinyl) phenoxy] -4-pyridazinol (Compound No. 2529) and 6-chloro-3- [2- (1,2-dimethyl-1-propenyl) phenoxy]- 4-pyridazinol (Compound No. 2542)
(1) 1- [2- (methoxymethoxy) phenyl] ethanone 3.39 g (24.9 mmol) of commercially available 1- (2-hydroxyphenyl) ethanone was dissolved in N, N-dimethylformamide (25 mL), 1.52 g (38.0 mmol) of% sodium hydride was added, and the mixture was stirred for 20 minutes under ice cooling. To this, 3.00 mL (39.5 mmol) of chloro (methoxy) methane was slowly added dropwise and stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 4.33 g (24.1 g of 2- [2- (methoxymethoxy) phenyl] ethanone. Mmol, yield 96.8%).
(2) 2- [2- (methoxymethoxy) phenyl] -3-methyl-2-butanol 1.00 g (5.56 mmol) of 1- [2- (methoxymethoxy) phenyl] ethanone obtained in (1) was dried in tetrahydrofuran. (3 mL) was dissolved, and 2.8 mL (5.6 mmol) of a 2 mol / L isopropylmagnesium bromide tetrahydrofuran solution was added dropwise under a nitrogen atmosphere and ice cooling. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 1 hour and 30 minutes. The reaction mixture was poured into water, acidified with dilute hydrochloric acid, and extracted with ether. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 2- [2- (methoxymethoxy) phenyl] -3-methyl-2. -0.522 g (2.33 mmol, yield 41.9%) of butanol was obtained.
(3) 6-chloro-3- [2- (1-isopropylvinyl) phenoxy] pyridazine 1-oxide and 6-chloro-3- [2- (1,2-dimethyl-1-propenyl) phenoxy] pyridazine 1- Mixture containing oxide, etc. 2- (2- (methoxymethoxy) phenyl] -3-methyl-2-butanol obtained in (2) was dissolved in 0.522 g (2.33 mmol) in dichloromethane (3 mL), and the mixture was cooled with ice. 0.50 mL (3.6 mmol) of triethylamine and then 0.25 mL (3.2 mmol) of methanesulfonyl chloride were added and stirred overnight at room temperature. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane: ethyl acetate, gradient), and a crude product containing 2- (1,2-dimethyl-1-propenyl) phenol and the like 186 mg was obtained. 132 mg of this crude product was mixed with 1,4-dioxane (2 mL) and dimethyl sulfoxide (2 mL), and 100 mg (0.893 mmol) of potassium tert-butoxide was added to the mixture. Next, 119 mg (0.721 mmol) of 3,6-dichloropyridazine 1-oxide was added to the mixture, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane: ethyl acetate, gradient) to give 6-chloro-3- [2- (1-isopropylvinyl) phenoxy] 220 mg of a mixture containing pyridazine 1-oxide, 6-chloro-3- [2- (1,2-dimethyl-1-propenyl) phenoxy] pyridazine 1-oxide and the like was obtained.
(4) 4,6-dichloro-3- [2- (1-isopropylvinyl) phenoxy] pyridazine and 4,6-dichloro-3- [2- (1,2-dimethyl-1-propenyl) phenoxy] pyridazine ( Step B-3)
6-Chloro-3- [2- (1-isopropylvinyl) phenoxy] pyridazine 1-oxide and 6-chloro-3- [2- (1,2-dimethyl-1-propenyl) phenoxy obtained in (3) ] 200 mg of a mixture containing pyridazine 1-oxide and the like was dissolved in chloroform (0.4 mL), 0.40 mL (4.3 mmol) of phosphorus oxychloride was mixed, and the mixture was stirred at 70 ° C. for 2 hours. The reaction mixture was poured into water and extracted with dichloromethane. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed 3 times with hexane: acetone = 20: 1), and 4,6- Dichloro-3- [2- (1-isopropylvinyl) phenoxy] pyridazine (86% purity, containing 14% 4,6-dichloro-3- [2- (1,2-dimethyl-1-propenyl) phenoxy] pyridazine ) 23 mg, and 4,6-dichloro-3- [2- (1,2-dimethyl-1-propenyl) phenoxy] pyridazine (81% purity, 4,6-dichloro-3- [2- (1-isopropyl) Vinyl) phenoxy] pyridazine (with 19%).
(5) 6-chloro-3- [2- (1-isopropylvinyl) phenoxy] -4-pyridazinol (Compound No. 2529, Steps A-3 and A-4)
4,6-dichloro-3- [2- (1-isopropylvinyl) phenoxy] pyridazine obtained in (4) (purity 86%, 4,6-dichloro-3- [2- (1,2-dimethyl- 23 mg (containing 14% of 1-propenyl) phenoxy] pyridazine) was dissolved in dimethyl sulfoxide (1 mL), 80 mg (0.98 mmol) of sodium acetate was added, and the mixture was stirred at 60 ° C. for 9 hours. The reaction mixture was cooled, poured into water and acidified with dilute hydrochloric acid. This mixture was extracted with ethyl acetate, and the organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 2 plates used, developed with hexane: ethyl acetate = 1: 1), and 6-chloro-3 -[2- (1-Isopropylvinyl) phenoxy] -4-pyridazinol (Compound 2529, 91% purity, 9% 6-chloro-3- [2- (1,2-dimethyl-1-propenyl) phenoxy]- 4.5 mg of 4-pyridazinol was obtained. Also, 77% pure 6-chloro-3- [2- (1-isopropylvinyl) phenoxy] -4-pyridazinol (23% 6-chloro-3- [2- (1,2-dimethyl-1-propenyl) 11.0 mg) containing phenoxy] -4-pyridazinol.
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.40-7.05 (4H, m), 6.59 (1H, s), 5.90 (1H, s), 5.04 (1H, s), 2.71 (1H, septet, J = 6.9Hz), 0.98 (6H, d, J = 6.9Hz).
Physical properties: amorphous.
(6) 6-chloro-3- [2- (1,2-dimethyl-1-propenyl) phenoxy] -4-pyridazinol (Compound No. 2542, Steps A-3 and A-4)
4,6-dichloro-3- [2- (1,2-dimethyl-1-propenyl) phenoxy] pyridazine obtained in (4) (purity 81%, 4,6-dichloro-3- [2- (1 -Isopropylvinyl) phenoxy] pyridazine (19 mg) was dissolved in dimethyl sulfoxide (2 mL), sodium acetate 68 mg (0.83 mmol) was added, and the mixture was stirred at 50 ° C. for 11 hours. The reaction mixture was cooled, poured into water and acidified with dilute hydrochloric acid. This mixture was extracted with ethyl acetate, and the organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 2 plates used, developed with hexane: ethyl acetate = 2: 1), and 6-chloro-3 -[2- (1,2-Dimethyl-1-propenyl) phenoxy] -4-pyridazinol (Compound 2542, 86% purity, 14% 6-chloro-3- [2- (1-isopropylvinyl) phenoxy]- 40.2 mg of 4-pyridazinol was obtained. Also, 73% pure 6-chloro-3- [2- (1,2-dimethyl-1-propenyl) phenoxy] -4-pyridazinol (27% 6-chloro-3- [2- (1-isopropylvinyl) 3.7 mg)) containing phenoxy] -4-pyridazinol.
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.38-7.05 (4H, m), 6.59 (1H, s), 1.78 (3H, s), 1.62 (3H, s), 1.46 (3H, s).
Physical properties: amorphous.

(Example 625)
6-Chloro-3- [2- (2-methyl-1-propenyl) phenoxy] -4-pyridazinol (Compound No. 2540)
(1) 1- (2-Methoxyphenyl) -2-methyl-1-propanol To 1.01 g (7.43 mmol) of commercially available 2-methoxybenzaldehyde was added dry tetrahydrofuran (3 mL) in a nitrogen atmosphere, and the mixture was ice-cooled. To this was added dropwise 3.8 mL (7.6 mmol) of a 2 mol / L isopropylmagnesium bromide tetrahydrofuran solution. After completion of the dropwise addition, the reaction mixture was stirred for 1 hour under ice cooling. The reaction mixture was poured into water, acidified with dilute hydrochloric acid, and extracted with ether. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 1- (2-methoxyphenyl) -2-methyl-1-propanol. 1.00 g (5.56 mmol, yield 74.8%) was obtained.
(2) 1- (1-Chloro-2-methylpropyl) -2-methoxybenzene 630 mg (3.50 mmol) of 1- (2-methoxyphenyl) -2-methyl-1-propanol obtained in (1) After dissolving in dichloromethane (3 mL), 0.70 mL (5.0 mmol) of triethylamine and then 0.35 mL (4.5 mmol) of methanesulfonyl chloride were added and stirred for 1 hour. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 720 mg of 1- (1-chloro-2-methylpropyl) -2-methoxybenzene.
(3) 1-methoxy-2- (2-methyl-1-propenyl) benzene 410 mg of 1- (1-chloro-2-methylpropyl) -2-methoxybenzene obtained in (2) was dried N, N- Dissolved in dimethylformamide (8 mL), 395 mg (3.52 mmol) of potassium tert-butoxide was added thereto under ice cooling. The reaction mixture was heated to reflux for 2 hours, then cooled to room temperature and poured into water. Extraction with hexane was performed, and the obtained organic layers were combined and washed successively with water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off to obtain 460 mg of 1-methoxy-2- (2-methyl-1-propenyl) benzene.
(4) 2- (2-Methyl-1-propenyl) phenol Under a nitrogen atmosphere, 60.0 mg (1.50 mmol) of 60% sodium hydride was suspended in dry N, N-dimethylformamide (3 mL). Under ice cooling, 0.11 mL (1.5 mmol) of ethanethiol was slowly added dropwise. After stirring for 10 minutes, a solution of 200 mg of 1-methoxy-2- (2-methyl-1-propenyl) benzene obtained in (3) in dry N, N-dimethylformamide (0.5 mL) was added dropwise for 2 hours 30 minutes. Heated to reflux. After allowing to cool, the reaction mixture was poured into water, acidified with dilute hydrochloric acid, and extracted with hexane. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 220 mg of 2- (2-methyl-1-propenyl) phenol.
(5) 6-chloro-3- [2- (2-methyl-1-propenyl) phenoxy] pyridazine 1-oxide and 3-chloro-6- [2- (2-methyl-1-propenyl) phenoxy] pyridazine 1 -Oxide mixture (step B-2)
200 mg of 2- (2-methyl-1-propenyl) phenol obtained in (4), 1,4-dioxane (2 mL) and dimethyl sulfoxide (2 mL) were mixed, and 151 mg of potassium tert-butoxide (1. 35 mmol) was added, and the mixture was stirred for 15 minutes under ice cooling. To this mixture was added 207 mg (1.25 mmol) of 3,6-dichloropyridazine 1-oxide, and the mixture was stirred for 15 minutes under ice cooling and then at room temperature for 4 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 6-chloro-3- [2- (2-methyl-1-propenyl). ) Phenoxy] pyridazine 1-oxide and 3-chloro-6- [2- (2-methyl-1-propenyl) phenoxy] pyridazine 1-oxide were mixed in 90.0 mg (0.325 mmol, 1- (2-methoxyphenyl)- Yield 41.2% from 2-methyl-1-propanol).
(6) 4,6-Dichloro-3- [2- (2-methyl-1-propenyl) phenoxy] pyridazine (Step B-3)
6-Chloro-3- [2- (2-methyl-1-propenyl) phenoxy] pyridazine 1-oxide and 3-chloro-6- [2- (2-methyl-1-propenyl) obtained in (5) 90.0 mg (0.325 mmol) of the phenoxy] pyridazine 1-oxide mixture was dissolved in chloroform (0.2 mL), 0.20 mL (2.2 mmol) of phosphorus oxychloride was mixed, and the mixture was stirred at 70 ° C. for 2 hours. The reaction mixture was poured into water and extracted with dichloromethane. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, developed with hexane: ethyl acetate = 9: 1), and 4,6-dichloro- 85.0 mg (0.288 mmol, yield 88.6%) of 3- [2- (2-methyl-1-propenyl) phenoxy] pyridazine was obtained.
(7) 6-chloro-3- [2- (2-methyl-1-propenyl) phenoxy] -4-pyridazinol (Compound No. 2540, Steps A-3 and A-4)
85.0 mg (0.288 mmol) of 4,6-dichloro-3- [2- (2-methyl-1-propenyl) phenoxy] pyridazine obtained in (6) was dissolved in dimethyl sulfoxide (3 mL), and 122 mg of sodium acetate ( 1.49 mmol) was added and the mixture was stirred at 120 ° C. for 2 hours. The reaction mixture was cooled to room temperature, poured into water and acidified with dilute hydrochloric acid. This mixture was extracted with ethyl acetate, and the organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by preparative thin layer chromatography (MERCK, 1.05744, used in 2 plates, developed with ethyl acetate) to give 6-chloro-3- [2- (2 39.6 mg (0.143 mmol, yield 49.7%) of -methyl-1-propenyl) phenoxy] -4-pyridazinol (Compound No. 2540) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.35-7.15 (3H, m), 7.15-7.05 (1H, m), 6.65 (1H, s), 6.05 (1H, s), 1.76 (3H, s ), 1.70 (3H, s).
Melting point (° C): 149-152.

(Example 626)
6-Chloro-3- (3-hydroxyphenoxy) -4-pyridazinol (Compound No. 2544)
(1) 1- {3-[(6-chloro-1-oxide-3-pyridazinyl) oxy] phenyl} ethanone and 1- {3-[(6-chloro-2-oxide-3-pyridazinyl) oxy] phenyl } Ethanone mixture
306 mg (2.25 mmol) of 1- (3-hydroxyphenyl) ethanone, 1,4-dioxane (6 mL) and dimethyl sulfoxide (6 mL) are mixed, and 297 mg (2.65 mmol) of potassium tert-butoxide is added to the mixture, Stir for 15 minutes. To this mixture, 342 mg (2.07 mmol) of 3,6-dichloropyridazine 1-oxide was added under ice cooling, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 1- {3-[(6-chloro-1-oxide-3- 400 mg (1.51 mmol, 72.9% yield) of a mixture of pyridazinyl) oxy] phenyl} ethanone and 1- {3-[(6-chloro-2-oxide-3-pyridazinyl) oxy] phenyl} ethanone was obtained.
(2) A mixture of 3-[(6-chloro-1-oxide-3-pyridazinyl) oxy] phenyl acetate and 3-[(6-chloro-2-oxide-3-pyridazinyl) oxy] phenyl acetate (1) 1- {3-[(6-chloro-1-oxide-3-pyridazinyl) oxy] phenyl} ethanone and 1- {3-[(6-chloro-2-oxide-3-pyridazinyl) oxy] phenyl obtained } 400 mg (1.51 mmol) of a mixture of ethanone was dissolved in 3 mL of dichloromethane, to which was added a solution of 1.1 g of m-chloroperbenzoic acid (purity 70-75%, 4.5-4.8 mmol) in dichloromethane (3 mL) and at room temperature for 4 days. Stir. A saturated aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was stirred and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient), and the raw material and 3-[(6-chloro-1-oxide-3-pyridazinyl ) Oxy] phenyl acetate and 330 mg of a mixture of 3-[(6-chloro-2-oxide-3-pyridazinyl) oxy] phenyl acetate were obtained. 280 mg of this mixture was dissolved in dichloromethane (3 mL), and 1.1 g of m-chloroperbenzoic acid (purity 70-75%, 4.5-4.8 mmol) was added thereto, followed by stirring at room temperature overnight. The reaction mixture was poured into 10% aqueous sodium sulfite and extracted with dichloromethane. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was washed with hexane to give 3-[(6-chloro-1-oxide-3-pyridazinyl) oxy] phenyl acetate and 3-[(6-chloro-2-oxide- 310 mg of a mixture of 3-pyridazinyl) oxy] phenyl acetate was obtained.
(3) 3-[(4,6-Dichloro-3-pyridazinyl) oxy] phenyl acetate (Step B-3)
Mixture of 3-[(6-chloro-1-oxide-3-pyridazinyl) oxy] phenyl acetate and 3-[(6-chloro-2-oxide-3-pyridazinyl) oxy] phenyl acetate obtained in (2) 310 mg was mixed with chloroform (0.4 mL), 0.40 mL (4.3 mmol) of phosphorus oxychloride was mixed, and the mixture was stirred at 70 ° C. for 3 hours. The reaction mixture was poured into water, stirred, and extracted with dichloromethane. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 3-[(4,6-dichloro-3-pyridazinyl) oxy] phenyl 46.0 mg (0.154 mmol, 1- {3-[(6-chloro-1-oxide-3-pyridazinyl) oxy] phenyl} ethanone and 1- {3-[(6-chloro-2-oxide-3- Yield 9.6% from a mixture of pyridazinyl) oxy] phenyl} ethanone).
(4) 6-chloro-3- (3-hydroxyphenoxy) -4-pyridazinol (Compound No. 2544, Steps A-3 and A-4)
Dissolve 40.0 mg (0.134 mmol) of 3-[(4,6-dichloro-3-pyridazinyl) oxy] phenyl acetate obtained in (3) in dimethyl sulfoxide (1 mL) and add 56.0 mg (0.683 mmol) of sodium acetate. The mixture was heated and stirred at 120 ° C. for 1 hour. After cooling to room temperature, the reaction mixture was poured into 0.5 mol / L aqueous sodium hydroxide solution and washed with ethyl acetate. The aqueous layer was acidified with 4 mol / L hydrochloric acid and extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off to obtain 30 mg (0.126 mmol, yield 94.0%) of 6-chloro-3- (3-hydroxyphenoxy) -4-pyridazinol (Compound No. 2544).
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.25-7.10 (1H, m), 6.70-6.57 (4H, m).
Melting point (° C): 248-251.

(Example 627)
6-Chloro-3- (2-iodo-3-methoxyphenoxy) -4-pyridazinol (Compound No. 2551)
(1) 1-methoxy-3- (methoxymethoxy) benzene 3.68 g (29.7 mmol) of commercially available 3-methoxyphenol was dissolved in N, N-dimethylformamide (50 mL), and 1.81 g of 60% sodium hydride under ice cooling. (45.4 mmol) was added and stirred for 20 minutes under ice cooling. Under ice cooling, 4.05 mL (53.3 mmol) of chloro (methoxy) methane was slowly added dropwise thereto, and the mixture was stirred overnight at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient), and 4.81 g (28.6 mmol) of 1-methoxy-3- (methoxymethoxy) benzene was obtained. Yield 96.3%).
(2) 2-Iodo-1-methoxy-3- (methoxymethoxy) benzene 1.70 g (22.0 mmol) of 1-methoxy-3- (methoxymethoxy) benzene obtained in (1) was dissolved in dry ether (50 mL). The mixture was cooled to −78 ° C. under a nitrogen atmosphere, and 5.60 mL (37.2 mmol) of tetramethylethylenediamine was added followed by 22.0 mL (35.2 mmol) of n-butyllithium hexane solution (1.60 M). After stirring at -78 ° C for 30 minutes and then at 0 ° C for 30 minutes, the mixture was cooled to -78 ° C and 9.80 g (38.6 mmol) of iodine was added. The mixture was stirred at -78 ° C for 30 minutes, saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium thiosulfate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 6.59 g of 2-iodo-1-methoxy-3- (methoxymethoxy) benzene.
(3) 2-iodo-3-methoxyphenol 6.59 g of 2-iodo-1-methoxy-3- (methoxymethoxy) benzene obtained in (2) was dissolved in methanol (70 mL), and concentrated hydrochloric acid (0.18 mL) was added. The mixture was added dropwise and stirred at 65 ° C. for 1 hour and 15 minutes. Concentrated hydrochloric acid (0.20 mL) was further added, and the mixture was heated and stirred at 65 ° C. for 2 hours and 40 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 4.61 g (18.4 mmol, 1- 1 mmol of 2-iodo-3-methoxyphenol). The yield from methoxy-3- (methoxymethoxy) benzene was 83.6%).
(4) A mixture of 6-chloro-3- (2-iodo-3-methoxyphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-iodo-3-methoxyphenoxy) pyridazine 1-oxide (Step B- 2)
2-Iodo-3-methoxyphenol 298 mg (1.19 mmol) 1,4-dioxane (2.5 mL) and dimethyl sulfoxide (2.5 mL) obtained in (3) were mixed, and potassium tert-butoxide 215 mg (1.92 Mmol) and stirred for 10 minutes under ice cooling. To this mixture, 196 mg (1.19 mmol) of 3,6-dichloropyridazine 1-oxide was added under ice cooling, and the mixture was stirred at room temperature for 3 days. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (hexane: ethyl acetate = 3: 1, then developed with hexane: ethyl acetate = 1: 1) to give 6-chloro- 324 mg (0.855 mmol, 71.8% yield) of a mixture of 3- (2-iodo-3-methoxyphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-iodo-3-methoxyphenoxy) pyridazine 1-oxide Obtained.
(5) 4,6-Dichloro-3- (2-iodo-3-methoxyphenoxy) pyridazine (Step B-3)
Mixture of 6-chloro-3- (2-iodo-3-methoxyphenoxy) pyridazine 1-oxide and 3-chloro-6- (2-iodo-3-methoxyphenoxy) pyridazine 1-oxide obtained in (4) To 324 mg (0.855 mmol), 1.0 mL (1.1 mmol) of phosphorus oxychloride was added and stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate = 5: 1), and 4,6-dichloro-3- (2-iodo-3-methoxyphenoxy) 225 mg (0.567 mmol, 66.3% yield) of pyridazine was obtained.
(6) 6-chloro-3- (2-iodo-3-methoxyphenoxy) -4-pyridazinol (Compound No. 2551, Steps A-3 and A-4)
105 mg (0.264 mmol) of 4,6-dichloro-3- (2-iodo-3-methoxyphenoxy) pyridazine obtained in (5) was dissolved in dimethyl sulfoxide (2 mL), and 118 mg (1.44 mmol) of sodium acetate was added. The mixture was heated and stirred at 120 ° C. for 1 hour and 30 minutes. After cooling to room temperature, 4 mol / L aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined and washed with saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the resulting residue was washed with isopropyl ether to give 6-chloro-3- (2-iodo-3-methoxyphenoxy) -4-pyridazinol (Compound No. 2551) Of 51.2 mg (0.135 mmol, yield 51.1%).
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.39 (1H, t, J = 8.4 Hz), 6.84 (2H, br.t, J = 8.4 Hz), 6.73 (1H, s), 3.90 (3H, s).
Melting point (° C): 231-234.

(Example 628)
6-chloro-3-{[7- (3-hydroxypropyl) bicyclo [4.2.0] octa-1,3,5-trien-2-yl] oxy} -4-pyridazinol (Compound No. 2555)
(1) 2-Iodo-3-methoxyphenyl trifluoromethanesulfonate 2.75 g (15.0 mmol) of 2-iodo-3-methoxyphenol obtained in Example 627 (3) was dissolved in dry dichloromethane, and 7.28 mL (90.0 mmol) of pyridine was dissolved. ) Was added. The mixture was cooled to −20 ° C., 5.40 mL (32.2 mmol) of trifluoromethanesulfonic anhydride was added, and the mixture was stirred for 3 hours and 50 minutes. The reaction mixture was poured into water and extracted with dichloromethane and then ethyl acetate. The organic layers were combined, washed successively with 4 mol / L hydrochloric acid, water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, the residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate = 10: 1), and 5.52 g (14.5 mmol, 2-iodo-3-methoxyphenyl trifluoromethanesulfonate) Yield 96.7%).
(2) tert-butyl [(8-methoxy-2,3,4,4a-tetrahydro-8bH-benzo [3,4] cyclobuta [1,2-b] pyran-8b-yl) oxy] dimethylsilane (1 ) 1.10 g (2.88 mmol) of 2-iodo-3-methoxyphenyl trifluoromethanesulfonate obtained in 1) was dissolved in dry tetrahydrofuran (15 mL), and commercially available tert-butyl (3,4-dihydro-2H-pyran was added under a nitrogen atmosphere. 1.00 mL (4.37 mmol) of -6-yloxy) dimethylsilane was added. The mixture was cooled to −78 ° C., 4.50 mL (7.20 mmol) of n-butyllithium hexane solution (1.60 M) was added, and the mixture was stirred for 20 minutes. The reaction mixture pH7 buffer was injected into (a 9.1gKH ₂ PO ₄ and 4.3gNa ₂ HPO ₄ prepared by dissolving in water 1L), and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate = 50: 1), and tert-butyl [(8-methoxy-2,3,4,4a-tetrahydro There was obtained 0.897 g (2.79 mmol, yield 96.9%) of -8bH-benzo [3,4] cyclobuta [1,2-b] pyran-8b-yl) oxy] dimethylsilane.
(3) 8- (3-hydroxypropyl) -5-methoxybicyclo [4.2.0] octa-1,3,5-trien-7-one (2) tert-butyl [(8-methoxy- 2,3,4,4a-tetrahydro-8bH-benzo [3,4] cyclobuta [1,2-b] pyran-8b-yl) oxy] dimethylsilane dissolved in 897 mg (2.79 mmol) in acetonitrile (12 mL) Under ice-cooling, 0.30 mL (7.96-8.30 mmol) of a 46-47% aqueous hydrofluoric acid solution was added and stirred for 30 minutes. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate = 7: 3), and 8- (3-hydroxypropyl) -5-methoxybicyclo [4.2.0] 446 mg (2.17 mmol, yield 77.8%) of octa-1,3,5-trien-7-one was obtained.
(4) 8- (3-Hydroxypropyl) -5-methoxybicyclo [4.2.0] octa-1,3,5-trien-7-one 8- (3-hydroxypropyl)-obtained from (3) 474 mg (2.30 mmol) of 5-methoxybicyclo [4.2.0] octa-1,3,5-trien-7-one was dissolved in dichloromethane (22 mL), and 467 mg (3.49 mmol) of N-chlorosuccinimide and tri 917 mg (3.5 mmol) of phenylphosphine was added and stirred at room temperature for 1 hour. The reaction mixture was poured into water, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate = 20: 1), and 8- (3-chloropropyl) -5-methoxybicyclo [4.2.0] 409 mg (1.82 mmol, yield 79.1%) of octa-1,3,5-trien-7-one was obtained.
(5) 7- (3-Chloropropyl) -2-methoxybicyclo [4.2.0] octa-1,3,5-triene Water (6 mL) was dissolved in 111 mg (0.408 mmol) of mercury chloride (HgCl ₂ ). Here, 4.00 g (6.12 mmol) of zinc powder was added, and the mixture was stirred at room temperature for 50 minutes. The supernatant was removed and the remaining solid was washed once with water. To this was slowly added water (6.0 mL), then concentrated hydrochloric acid (5.0 mL), and acetic acid (2.4 mL). Finally, 8- (3-chloropropyl) -5-methoxybicyclo obtained in (4) was added. [4.2.0] Octa-1,3,5-trien-7-one 409 mg (1.82 mmol) was dissolved in toluene (2 mL) and ethanol (2 mL) and added. The mixture was stirred at 115 ° C. overnight and cooled to room temperature. Toluene (20 mL) was added and stirred for 30 minutes, and the organic layer was separated. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate = 20: 1), 7- (3-chloropropyl) -2-methoxybicyclo [4.2.0] 304 mg (1.44 mmol, yield 79.1%) of octa-1,3,5-triene was obtained.
(6) 7- (3-chloropropyl) -2-methoxybicyclo obtained from 7- (3-chloropropyl) bicyclo [4.2.0] octa-1,3,5-trien-2-ol (5) [4.2.0] Octa-1,3,5-triene (304 mg, 1.44 mmol) was dissolved in dichloromethane (2.0 mL). Under ice-cooling, boron tribromide (0.50 mL, 5.32 mmol) was added and the mixture was ice-cooled. Stirred for 1 hour. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate = 4: 1), and 7- (3-chloropropyl) bicyclo [4.2.0] octa-1, 303 mg (1.54 mmol, quantitative yield) of 3,5-trien-2-ol was obtained.
(7) 6-chloro-3-{[7- (3-chloropropyl) bicyclo [4.2.0] octa-1,3,5-trien-2-yl] oxy} pyridazine 1-oxide and 3-chloro- 6-{[7- (3-Chloropropyl) bicyclo [4.2.0] octa-1,3,5-trien-2-yl] oxy} pyridazine 1-oxide mixture (step B-2)
7- (3-Chloropropyl) bicyclo [4.2.0] octa-1,3,5-trien-2-ol 303 mg (1.54 mmol), 1,4-dioxane (2.0 mL) obtained in (6) and Dimethyl sulfoxide (2.0 mL) was mixed, 275 mg (2.46 mmol) of potassium tert-butoxide was added to the mixture, and the mixture was stirred for 10 minutes under ice cooling. To this mixture, 254 mg (1.54 mmol) of 3,6-dichloropyridazine 1-oxide was added under ice cooling, and the mixture was stirred overnight at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (developed with hexane: ethyl acetate = 3: 1) to give 6-chloro-3-{[7- (3-chloropropyl ) Bicyclo [4.2.0] octa-1,3,5-trien-2-yl] oxy} pyridazine 1-oxide and 3-chloro-6-{[7- (3-chloropropyl) bicyclo [4.2.0] 364 mg (1.12 mmol, yield 72.7%) of a mixture of octa-1,3,5-trien-2-yl] oxy} pyridazine 1-oxide was obtained.
(8) 4,6-Dichloro-3-{[7- (3-chloropropyl) bicyclo [4.2.0] octa-1,3,5-trien-2-yl] oxy} pyridazine (Step B-3)
6-chloro-3-{[7- (3-chloropropyl) bicyclo [4.2.0] octa-1,3,5-trien-2-yl] oxy} pyridazine 1-oxide obtained in (7) and 364 mg (1.12 mmol) of a mixture of 3-chloro-6-{[7- (3-chloropropyl) bicyclo [4.2.0] octa-1,3,5-trien-2-yl] oxy} pyridazine 1-oxide To the solution, 1.0 mL (11 mmol) of phosphorus oxychloride was added and stirred at room temperature for 7 hours and 15 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin layer chromatography (developed with hexane: ethyl acetate = 2: 1) to give 4,6-dichloro-3-{[7- (3-chloropropyl) 253 mg (0.735 mmol, yield 65.6%) of bicyclo [4.2.0] octa-1,3,5-trien-2-yl] oxy} pyridazine was obtained.
(9) 6-chloro-3-{[7- (3-hydroxypropyl) bicyclo [4.2.0] octa-1,3,5-trien-2-yl] oxy} -4-pyridazinol (Compound No. 2555, Steps A-3 and A-4)
4,6-dichloro-3-{[7- (3-chloropropyl) bicyclo [4.2.0] octa-1,3,5-trien-2-yl] oxy} pyridazine 253 mg obtained in (8) ( 0.735 mmol) was dissolved in dimethyl sulfoxide (5.0 mL), 250 mg (3.05 mmol) of sodium acetate was added, and the mixture was stirred with heating at 120 ° C. for 2 hr. After cooling to room temperature, 4 mol / L aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined and washed with saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (developed with hexane: ethyl acetate = 2: 1) to give 6-chloro-3-{[ 48.5 mg (0.158 mmol, yield 21.5%) of 7- (3-hydroxypropyl) bicyclo [4.2.0] octa-1,3,5-trien-2-yl] oxy} -4-pyridazinol (Compound No. 2555) )Obtained. Also 28.2 mg 6-chloro-3-{[7- (3-chloropropyl) bicyclo [4.2.0] octa-1,3,5-trien-2-yl] oxy} -4-pyridazinol and 3- A mixture of {2-[(6-chloro-4-hydroxy-3-pyridazinyl) oxy] bicyclo [4.2.0] octa-1,3,5-trien-7-yl} propyl acetate was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.22-7.18 (1H, m), 6.98-6.94 (2H, m), 6.70 (1H, s), 3.62-3.56 (2H, m), 3.46 (1H , br.s), 3.34 (1H, br.s), 3.18 (1H, dd, J = 13.9, 5.5Hz), 2.62 (1H, dd, J = 13.9, 2.2Hz), 1.81-1.62 (4H, m ).
Physical property: Oily substance.

(Example 629)
6-Chloro-3-[(7,7-dimethylbicyclo [4.2.0] octa-1,3,5-trien-2-yl) oxy] -4-pyridazinol (Compound No. 2556)
(1) 5-Methoxy-8,8-dimethylbicyclo [4.2.0] octa-1,3,5-trien-7-one 2-iodo-3-methoxyphenyl obtained by the method of Example 628 (1) Dissolve 723 mg (1.89 mmol) of trifluoromethanesulfonate in dry tetrahydrofuran (10 mL) and add 0.50 mL (2.47 mmol) of commercially available [(1-methoxy-2-methyl-1-propynyl) oxy] (trimethyl) silane under a nitrogen atmosphere. added. The mixture was cooled to −78 ° C., 2.70 mL (4.32 mmol) of n-butyllithium hexane solution (1.60 M) was added, and the mixture was stirred for 20 minutes. The reaction mixture pH7 buffer was injected into (a 9.1gKH ₂ PO ₄ and 4.3gNa ₂ HPO ₄ prepared by dissolving in water 1L), and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, tetrahydrofuran (2.0 mL), water (0.2 mL) and acetic acid (2.0 mL) were added to the residue, and the mixture was stirred at room temperature for 1 hr. Ether was added to the reaction mixture, which was washed successively with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin layer chromatography (developed with hexane: ethyl acetate = 2: 1) to give 5-methoxy-8,8-dimethylbicyclo [4.2.0] octa-1 , 3,5-trien-7-one was obtained (182 mg, 1.03 mmol, yield 54.5%).
(2) 2-Methoxy-7,7-dimethylbicyclo [4.2.0] octa-1,3,5-triene Water (6 mL) was added to 109 mg (0.401 mmol) of mercury chloride (HgCl ₂ ) and dissolved. 3.98 g (6.09 mmol) of zinc powder was added and stirred at room temperature for 1 hour. The supernatant was removed and the remaining solid was washed once with water. Water (6.0 mL) and then concentrated hydrochloric acid (5.0 mL) were slowly added thereto, and acetic acid (2.4 mL) was finally added. Finally, 5-methoxy-8,8-dimethylbicyclo [4.2. 0] Octa-1,3,5-trien-7-one 182 mg (1.03 mmol) was dissolved in toluene (2 mL) and ethanol (2 mL) and added. The mixture was stirred at 115 ° C. overnight and cooled to room temperature. Toluene (20 mL) was added and stirred for 20 minutes, and the organic layer was separated. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin layer chromatography (developed with hexane: ethyl acetate = 25: 1) to give 2-methoxy-7,7-dimethylbicyclo [4.2.0] octa-1 85.1 mg (0.525 mmol, yield 51.0%) of 3,3,5-triene was obtained.
(3) 7,7-dimethylbicyclo [4.2.0] octa-1,3,5-trien-2-ol 2-methoxy-7,7-dimethylbicyclo [4.2.0] octa obtained from (2) Dissolve 85.1 mg (0.525 mmol) of -1,3,5-triene in dichloromethane (5.0 mL), add 0.20 mL (2.12 mmol) of boron tribromide with stirring under ice cooling, and add 2 hours 10 minutes under ice cooling. Stir. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 97.6 mg of 7,7-dimethylbicyclo [4.2.0] octa-1,3,5-trien-2-ol.
(4) 6-chloro-3-[(7,7-dimethylbicyclo [4.2.0] octa-1,3,5-trien-2-yl) oxy] pyridazine 1-oxide and 3-chloro-6- [ (7,7-Dimethylbicyclo [4.2.0] octa-1,3,5-trien-2-yl) oxy] pyridazine 1-oxide (Step B-2)
7,7-dimethylbicyclo [4.2.0] octa-1,3,5-trien-2-ol 97.6 mg, 1,4-dioxane (1.5 mL) and dimethyl sulfoxide (1.5 mL) obtained in (3) Were mixed, 97.8 mg (0.873 mmol) of potassium tert-butoxide was added to the mixture, and the mixture was stirred for 10 minutes under ice cooling. To this mixture, 90.2 mg (0.547 mmol) of 3,6-dichloropyridazine 1-oxide was added under ice cooling, and the mixture was stirred overnight at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (developed twice with hexane: ethyl acetate = 3: 1) to give 6-chloro-3-[(7,7-dimethyl Bicyclo [4.2.0] octa-1,3,5-trien-2-yl) oxy] pyridazine 1-oxide and 3-chloro-6-[(7,7-dimethylbicyclo [4.2.0] octa-1, 3,5-trien-2-yl) oxy] pyridazine 1-oxide mixture from 61.7 mg (0.223 mmol, 2-methoxy-7,7-dimethylbicyclo [4.2.0] octa-1,3,5-triene Yield 42.5%).
(5) 4,6-dichloro-3-[(7,7-dimethylbicyclo [4.2.0] octa-1,3,5-trien-2-yl) oxy] pyridazine (Step B-3)
6-Chloro-3-[(7,7-dimethylbicyclo [4.2.0] octa-1,3,5-trien-2-yl) oxy] pyridazine 1-oxide and 3-chloro obtained in (4) -6-[(7,7-Dimethylbicyclo [4.2.0] octa-1,3,5-trien-2-yl) oxy] pyridazine 1-oxide mixture 61.7mg (0.223mmol) to phosphorus oxychloride 0.50mL (5.4 mmol) was added and stirred at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin layer chromatography (developed with hexane: ethyl acetate = 5: 1) to give 4,6-dichloro-3-[(7,7-dimethylbicyclo [4.2 .0] octa-1,3,5-trien-2-yl) oxy] pyridazine was obtained, 43.7 mg (0.148 mmol, 66.4% yield).
(6) 6-chloro-3-[(7,7-dimethylbicyclo [4.2.0] octa-1,3,5-trien-2-yl) oxy] -4-pyridazinol (Compound No. 2556, Step A- 3 and step A-4)
4,6-dichloro-3-[(7,7-dimethylbicyclo [4.2.0] octa-1,3,5-trien-2-yl) oxy] pyridazine obtained in (5) 43.7 mg (0.148 mmol) ) Was dissolved in dimethyl sulfoxide (2.0 mL), 63.1 mg (0.770 mmol) of sodium acetate was added, and the mixture was stirred with heating at 120 ° C. for 2 hr. After cooling to room temperature, 4 mol / L aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the resulting residue was washed with isopropyl ether to give 6-chloro-3-[(7,7-dimethylbicyclo [4.2.0] octa-1,3, There was obtained 31.6 mg (0.114 mmol, yield 77.0%) of 5-trien-2-yl) oxy] -4-pyridazinol (Compound No. 2556).
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.26-7.19 (1H, m), 6.97-6.89 (2H, m), 6.71 (1H, s), 2.81 (2H, s), 1.41 (6H, s ).
Melting point (° C): 197-199.

(Example 630)
4-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] -3-methylphenyl acetate (Compound No. 2572)
(1) 1- {4-[(6-chloro-1-oxide-3-pyridazinyl) oxy] -3-methylphenyl} ethanone and 1- {4-[(6-chloro-2-oxide-3-pyridazinyl) ) Oxy] -3-methylphenyl} ethanone mixture (step B-2)
784 mg (5.23 mmol) of commercially available 1- (4-hydroxy-3-methylphenyl) ethanone, 1,4-dioxane (5 mL) and dimethyl sulfoxide (5 mL) were mixed, and 938 mg (8.38 mmol) of potassium tert-butoxide was added to this mixture. And stirred for 10 minutes under ice-cooling. To this mixture, 861 mg (5.22 mmol) of 3,6-dichloropyridazine 1-oxide was added under ice cooling, and the mixture was stirred overnight at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate = 5: 1) to give 1- {4-[(6-chloro-1-oxide-3-pyridazinyl ) Oxy] -3-methylphenyl} ethanone and 1- {4-[(6-chloro-2-oxide-3-pyridazinyl) oxy] -3-methylphenyl} ethanone in a mixture of 758 mg (2.74 mmol, yield 52.5 %)Obtained.
(2) 4-[(6-Chloro-1-oxide-3-pyridazinyl) oxy] -3-methylphenyl acetate and 4-[(6-Chloro-2-oxide-3-pyridazinyl) oxy] -3-methyl 1- {4-[(6-Chloro-1-oxide-3-pyridazinyl) oxy] -3-methylphenyl} ethanone and 1- {4-[(6-chloro -2-oxide-3-pyridazinyl) oxy] -3-methylphenyl} ethanone mixture 758mg (2.74mmol) dissolved in 1,2-dichloroethane (13mL), 2.62g m-chloroperbenzoic acid (purity 70-75% 10.6-11.4 mmol), and the mixture was stirred at room temperature for 4 hours and 45 minutes. Further, 1.20 g of m-chloroperbenzoic acid (purity 70-75%, 4.86-5.20 mmol) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into 10% aqueous sodium sulfite and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate = 5: 1), and the starting material, 4-[(6-chloro-1-oxide-3-pyridazinyl) oxy 622 mg of a mixture of] -3-methylphenyl acetate and 4-[(6-chloro-2-oxide-3-pyridazinyl) oxy] -3-methylphenyl acetate was obtained. 30 mL of hydrogen peroxide solution (0.5 mL, 4.85 mmol) was mixed with 1,2-dichloroethane (2.2 mL), and 3.2 mL (22.7 mmol) of trifluoroacetic anhydride was added dropwise under ice cooling, followed by stirring at room temperature. This mixture was mixed with the raw material obtained earlier, 4-[(6-chloro-1-oxide-3-pyridazinyl) oxy] -3-methylphenyl acetate, and 4-[(6-chloro-2-oxide-3 -Pyridazinyl) oxy] -3-methylphenyl acetate (622 mg) was added to a solution of 1,2-dichloroethane (2.2 mL) under ice cooling, and the mixture was stirred under ice cooling for 1 hr and at room temperature overnight. The reaction mixture was poured into 10% aqueous sodium sulfite and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium carbonate, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate gradient) to give 4-[(6-chloro-1-oxide-3-pyridazinyl) oxy] -3- A mixture of methylphenyl acetate and 4-[(6-chloro-2-oxide-3-pyridazinyl) oxy] -3-methylphenyl acetate was obtained (413 mg, 1.40 mmol, yield 51.1%).
(3) 4-[(4,6-Dichloro-3-pyridazinyl) oxy] -3-methylphenyl acetate (Step B-3)
4-[(6-Chloro-1-oxide-3-pyridazinyl) oxy] -3-methylphenyl acetate and 4-[(6-chloro-2-oxide-3-pyridazinyl) oxy] obtained in (2) 413 mg (1.40 mmol) of a mixture of -3-methylphenyl acetate was dissolved in chloroform (2 mL), and 2.0 mL (22 mmol) of phosphorus oxychloride was mixed and stirred at 80 ° C. for 3 hours. The reaction mixture was diluted with dichloromethane and poured into water. This mixture was extracted with dichloromethane and then with ethyl acetate. The organic layers were combined, washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, hexane-ethyl acetate = 6: 1), and 4-[(4,6-dichloro- There was obtained 336 mg (1.07 mmol, yield 76.4%) of 3-pyridazinyl) oxy] -3-methylphenyl acetate.
(4) 4-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] -3-methylphenyl acetate (Compound No. 2572, Step A-3 and Step A-4)
160 mg (0.511 mmol) of 4-[(4,6-dichloro-3-pyridazinyl) oxy] -3-methylphenyl acetate obtained in (3) was dissolved in dimethyl sulfoxide (1.5 mL), and 136 mg (1.66 mmol) of sodium acetate was dissolved. ) And heated and stirred at 120 ° C. for 2 hours. After cooling to room temperature, 4 mol / L aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the resulting residue was washed with isopropyl ether to give 4-[(6-chloro-4-hydroxy-3-pyridazinyl) oxy] -3-methylphenyl acetate ( Compound No. 2572) (37.3 mg, 0.126 mmol, yield 24.7%) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.13-6.94 (3H, m), 6.70 (1H, s), 2.27 (3H, s), 2.17 (3H, s).
Melting point (° C): 255 (dec.).

(Example 631)
6-Chloro-3- [2- (difluoromethyl) -6-methylphenoxy] -4-pyridazinol (Compound No. 2576)
(1) 2- (Methoxymethoxy) -3-methylbenzaldehyde
2.96 g (36.5 mmol) of 2-hydroxy-3-methylbenzaldehyde was dissolved in N, N-dimethylformamide (50 mL), and 2.19 g (54.6 mmol) of 60% sodium hydride was added under ice cooling, followed by stirring for 10 minutes. Under ice cooling, 3.59 mL (47.3 mmol) of chloro (methoxy) methane was added thereto and stirred at room temperature for 1 hour and 30 minutes. The reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was purified by silica gel column chromatography (Daisogel 1001W, hexane: ethyl acetate = 50: 1), and 6.60 g (36.6 mmol, yield) of 2- (methoxymethoxy) -3-methylbenzaldehyde was obtained. 100%).
(2) 1- (Difluoromethyl) -2- (methoxymethoxy) -3-methylbenzene 589 mg (3.27 mmol) of 2- (methoxymethoxy) -3-methylbenzaldehyde obtained from (1) was added to dichloromethane (10 mL). In a nitrogen atmosphere, 0.863 mL (6.52 mmol) of (diethylamino) sulfur trifluoride (DAST) was added and stirred at room temperature for 3 hours. After standing at room temperature overnight, the reaction mixture was poured into water and extracted with dichloromethane. The organic layers were combined, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Daisogel 1001W, hexane: ethyl acetate = 10: 1) to give 229 mg of 1- (difluoromethyl) -2- (methoxymethoxy) -3-methylbenzene. (1.13 mmol, yield 34.6%).
(3) 2- (Difluoromethyl) -6-methylphenol 1- (Difluoromethyl) -2- (methoxymethoxy) -3-methylbenzene 229 mg (1.13 mmol) obtained in (2) was added to methanol (5 mL). Dissolved, 2 drops of concentrated hydrochloric acid was added at room temperature, and the mixture was stirred at 60 ° C. for 30 min. The reaction mixture was cooled to room temperature and the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 135 mg (0.854 mmol, yield 75.6%) of 2- (difluoromethyl) -6-methylphenol.
(4) 6-chloro-3- [2- (difluoromethyl) -6-methylphenoxy] pyridazine 1-oxide and 3-chloro-6- [2- (difluoromethyl) -6-methylphenoxy] pyridazine 1-oxide (Process B-1)
135 mg (0.854 mmol) of 2- (difluoromethyl) -6-methylphenol obtained in (3) was dissolved in 1,4-dioxane (1.5 mL) and dimethyl sulfoxide (1.5 mL), and this mixture was ice-cooled. 115 mg (1.03 mmol) of potassium tert-butoxide was added and stirred for 5 minutes. To this mixture, 141 mg (0.855 mmol) of 3,6-dichloropyridazine 1-oxide was added under ice cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was subjected to silica gel column chromatography (eluted with hexane: ethyl acetate = 2: 1) and preparative thin layer chromatography (MERCK 1.05744, 3 hexanes: ethyl acetate = 2 6-chloro-3- [2- (difluoromethyl) -6-methylphenoxy] pyridazine 1-oxide and 3-chloro-6- [2- (difluoromethyl) -6- 28.6 mg (0.0997 mmol, 11.7% yield) of a mixture of methylphenoxy] pyridazine 1-oxide was obtained.
(5) 4,6-Dichloro-3- [2- (difluoromethyl) -6-methylphenoxy] pyridazine (Step B-3)
6-Chloro-3- [2- (difluoromethyl) -6-methylphenoxy] pyridazine 1-oxide and 3-chloro-6- [2- (difluoromethyl) -6-methylphenoxy] obtained in (4) 28.6 mg (0.0997 mmol) of a mixture of pyridazine 1-oxide was dissolved in chloroform (0.5 mL), 76.5 mg (0.50 mmol) of phosphorus oxychloride was added, and the mixture was heated to reflux for 8 hours. After leaving overnight at room temperature, water and dichloromethane were added to the reaction mixture and stirred for 30 minutes. This was extracted with dichloromethane, and the organic layers were combined, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by preparative thin layer chromatography (developed with MERCK 1.05744 hexane: ethyl acetate = 4: 1), and 4,6-dichloro-3- [2- (difluoromethyl ) -6-methylphenoxy] pyridazine (19.1 mg, 0.0626 mmol, yield 62.8%) was obtained.
(6) 6-chloro-3- [2- (difluoromethyl) -6-methylphenoxy] -4-pyridazinol (Compound No. 2576)
19.1 mg (0.0626 mmol) of 4,6-dichloro-3- [2- (difluoromethyl) -6-methylphenoxy] pyridazine obtained in (5) was dissolved in dimethyl sulfoxide (0.5 mL), and 25.7 mg of sodium acetate ( 0.313 mmol) was added and the mixture was stirred with heating at 120 ° C. for 2 hours. After cooling to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (developed with MERCK 1.05744 ethyl acetate) to give 6-chloro-3- [2- ( 17.8 mg (0.0620 mmol, 99.0% yield) of difluoromethyl) -6-methylphenoxy-4-pyridazinol (Compound No. 2576) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.55-7.25 (3H, m), 6.83 (1H, t, J = 55.1 Hz). 2.15 (3H, s).
Melting point (° C): 204-205.

(Example 632)
6-Chloro-3- [2,4-dibromo-5- (ethylsulfanyl) phenoxy] -4-pyridazinol (Compound No. 2596)
(1) 4,6-dichloro-3- [2,4-dibromo-5- (ethylsulfanyl) phenoxy] pyridazine Commercially available 1-bromo-2-methoxy-4-nitrobenzene (2.05 g, 8.84 mmol) and water (200 mL) ), And then ammonium chloride 11.4 g (213 mmol) and then zinc powder 4.78 g (73.2 mmol) were added. The mixture was stirred at room temperature for 5 hours, filtered through celite, and the filtrate was extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 1.78 g of residue.
This residue was mixed with water (9 mL) and a 47% aqueous hydrobromic acid solution (3 mL), and an aqueous solution (3.6 mL) of sodium nitrite 655 mg (9.49 mmol) was added dropwise with stirring under ice cooling. After completion of the dropwise addition, the mixture was stirred for 10 minutes, and a solution of 973 mg (6.80 mmol) of cuprous bromide in 47% aqueous hydrobromic acid solution (3.6 mL) was added dropwise. The reaction mixture was stirred at 110 ° C. for 2 hours 30 minutes, cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was subjected to silica gel column chromatography (Wakogel C-100, hexane: ethyl acetate = 10: 1) and preparative thin layer chromatography (MERCK, 1.05717 hexane: ethyl acetate = 4). To 1) (multiple development at 1) to obtain 751 mg of a crude product.
Under a nitrogen atmosphere, 339 mg (8.46 mmol) of 60% sodium hydride was suspended in dry N, N-dimethylformamide (5 mL), and 0.65 mL (8.78 mmol) of ethanethiol was slowly added dropwise to the suspension. After stirring for 30 minutes, a solution obtained by dissolving 751 mg of the above composition in N, N-dimethylformamide (8 mL) was added to this mixture, and the mixture was stirred at 160 ° C. for 5 hours. The reaction mixture was left at room temperature overnight, poured into water, acidified with dilute hydrochloric acid, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, multiple development with hexane: ethyl acetate = 4: 1) to produce a crude phenolic product. 109 mg of product was obtained.
109 mg of the obtained phenolic crude product was mixed with 1,4-dioxane (3 mL) and dimethyl sulfoxide (3 mL), and 53.5 mg (0.478 mmol) of potassium tert-butoxide was added to this mixture, followed by stirring for 15 minutes under ice cooling. did. To this mixture, 71.2 mg (0.432 mmol) of 3,6-dichloropyridazine 1-oxide was added under ice cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 3 plates used, multiple development with hexane: ethyl acetate = 2: 1) to produce a crude etheric product. 71.5 mg of product was obtained.
44.8 mg of ethereal crude product was dissolved in phosphorus oxychloride (3 mL) and stirred at 60 ° C. for 21 hours. Water and dichloromethane were added to the reaction mixture and stirred, followed by extraction with dichloromethane. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin-layer chromatography (MERCK, 1.05744, 2 plates used, developed with hexane: ethyl acetate = 2: 1), and 4,6-dichloro-3- 14.4 mg (0.0314 mmol, yield 0.567%) of [2,4-dibromo-5- (ethylsulfanyl) phenoxy] pyridazine was obtained.
(2) 6-chloro-3- [2,4-dibromo-5- (ethylsulfanyl) phenoxy] -4-pyridazinol (Compound No. 2596, Steps A-3 and A-4)
33.4 mg (0.0728 mmol) of 4,6-dichloro-3- [2,4-dibromo-5- (ethylsulfanyl) phenoxy] pyridazine obtained in (1) was dissolved in dimethyl sulfoxide (3 mL), and sodium acetate 29.8 mg (0.363 mmol) was added, and the mixture was stirred with heating at 120 ° C. for 4 hr 30 min. After standing overnight at room temperature, water was added to the reaction mixture, acidified with dilute hydrochloric acid, and extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (multiple development with MERCK 1.05744 ethyl acetate) to give 6-chloro-3- [2, 14.1 mg (0.0297 mmol, yield 40.8%) of 4-dibromo-5- (ethylsulfanyl) phenoxy] -4-pyridazinol (Compound No. 2596) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.84 (1H, s), 7.21 (1H, s), 6.72 (1H, s), 2.97 (2H, q, J = 7.3 Hz), 1.33 (3H, t, J = 7.3Hz).
Melting point (° C): 225-228.

(Example 633)
6-Chloro-3- (2,3,5-trimethyl-6-vinylphenoxy) -4-pyridazinol (Compound No. 2603)
(1) 1- (2-methoxy-3,4,6-trimethylphenyl) ethanone Manufactured by the method described in Chemical Research in Toxicology, 1997, Vol. 10, No. 3, pages 335-343 1- (2-hydroxy-3,4,6-trimethylphenyl) ethanone 2.00 g (11.2 mmol) can be dissolved in acetone (30 mL), potassium carbonate 3.10 g (22.4 mmol), then methyl iodide 1.40 mL (22.5 mmol) ) Was added and heated to reflux for 5 hours. After cooling to room temperature, the reaction mixture was concentrated and the residue was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-100, hexane: ethyl acetate gradient) to obtain 1.90 g of 1- (2-methoxy-3,4,6-trimethylphenyl) ethanone ( 9.90 mmol, yield 88.4%).
(2) 1- (2-methoxy-3,4,6-trimethylphenyl) ethanol 1.00 g (5.21 mmol) of 1- (2-methoxy-3,4,6-trimethylphenyl) ethanone obtained from (1) Was dissolved in methanol (8 mL), and 170 mg (4.50 mmol) of sodium borohydride was added little by little while stirring. After confirming the disappearance of the raw materials by analytical thin layer chromatography (TLC), the reaction mixture was poured into water and acidified with hydrochloric acid. This was extracted with hexane, the organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 1.0 g of 1- (2-methoxy-3,4,6-trimethylphenyl) ethanol.
(3) 2- (1-Chloroethyl) -3-methoxy-1,4,5-trimethylbenzene 1.0 g of 1- (2-methoxy-3,4,6-trimethylphenyl) ethanol obtained from (2) It was dissolved in dichloromethane (10 mL), and 1.10 mL (7.91 mmol) of triethylamine was added with stirring under ice-cooling, and then 0.56 mL (7.21 mmol) of methanesulfonyl chloride was added. The reaction mixture was stirred at room temperature for 20 minutes, poured into water and extracted with dichloromethane. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 1.2 g of 2- (1-chloroethyl) -3-methoxy-1,4,5-trimethylbenzene.
(4) 3-Methoxy-1,2,5-trimethyl-4-vinylbenzene 1.2 g of 2- (1-chloroethyl) -3-methoxy-1,4,5-trimethylbenzene obtained in (3) is dried. Dissolved in N, N-dimethylformamide (12 mL), 1.14 g (10.2 mmol) of potassium tert-butoxide was added with stirring under ice cooling. The reaction mixture was stirred at room temperature for 30 minutes and then stirred for 30 minutes under heating to reflux. After cooling to room temperature, it was poured into water and extracted with hexane. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 870 mg of 3-methoxy-1,2,5-trimethyl-4-vinylbenzene.
(5) 2,3,5-trimethyl-6-vinylphenol and 2- [1- (ethylsulfanyl) ethyl] -3,5,6-trimethylphenol 60% sodium hydride 270 mg (6.75 mmol) under nitrogen atmosphere Was suspended in dry N, N-dimethylformamide (8 mL), and 0.60 mL (8.10 mmol) of ethanethiol was slowly added dropwise to this suspension. After stirring for 15 minutes, 400 mg (2.27 mmol) of 3-methoxy-1,2,5-trimethyl-4-vinylbenzene obtained in (4) was added to dry N, N-dimethylformamide (1.5 mL). The dissolved one was added and heated to reflux for 1 hour. After cooling to room temperature, the reaction mixture was poured into water, acidified with hydrochloric acid, and extracted with hexane. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was subjected to silica gel column chromatography (Wakogel C-100, hexane: ethyl acetate = 20: 1) and preparative thin layer chromatography (MERCK, 1.05744 hexane: ethyl acetate = 8: 1). 2), 3,5-trimethyl-6-vinylphenol 63.0 mg (0.389 mmol, yield 16.2% from 1- (2-methoxy-3,4,6-trimethylphenyl) ethanone) And 2- [1- (ethylsulfanyl) ethyl] -3,5,6-trimethylphenol 330 mg (1.47 mmol, 61.4% yield from 1- (2-methoxy-3,4,6-trimethylphenyl) ethanone) Got.
(6) 6-chloro-3- (2,3,5-trimethyl-6-vinylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2,3,5-trimethyl-6-vinylphenoxy) pyridazine 1 -Oxide mixture (step B-2)
Dissolve 43.0 mg (0.265 mmol) of 2,3,5-trimethyl-6-vinylphenol obtained in (5) in 1,4-dioxane (0.4 mL) and dimethyl sulfoxide (0.4 mL). Then, 36.0 mg (0.321 mmol) of potassium tert-butoxide was added and stirred for 10 minutes. To this mixture, 47.6 mg (0.288 mmol) of 3,6-dichloropyridazine 1-oxide was added under ice cooling, followed by stirring at room temperature for 4 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (using MERCK 1.05744, 2 hexanes: ethyl acetate = 2: 1), and 6-chloro-3- (2 , 3,5-trimethyl-6-vinylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2,3,5-trimethyl-6-vinylphenoxy) pyridazine 1-oxide in a mixture of 27.6 mg (0.0949 mmol, Yield 35.8%).
(7) 4,6-Dichloro-3- (2,3,5-trimethyl-6-vinylphenoxy) pyridazine (Step B-3)
6-Chloro-3- (2,3,5-trimethyl-6-vinylphenoxy) pyridazine 1-oxide and 3-chloro-6- (2,3,5-trimethyl-6-vinyl obtained in (6) 0.02 mL (0.22 mmol) of phosphorus oxychloride was added to 27.6 mg (0.0949 mmol) of the phenoxy) pyridazine 1-oxide mixture, and the mixture was stirred at room temperature for 2 hours. Chloroform 0.4mL was added here, and it stirred at room temperature overnight. The reaction mixture was concentrated, 0.2 mL (2.2 mmol) of phosphorus oxychloride was added to the residue, and the mixture was stirred for 5 hours at room temperature. The reaction mixture was concentrated, and the residue was purified by preparative thin-layer chromatography (developed with hexane: ethyl acetate = 5: 1 using 1 piece of MERCK 1.05744), 4,6-dichloro-3- (2, 5.0 mg (0.016 mmol, 17% yield) of 3,5-trimethyl-6-vinylphenoxy) pyridazine was obtained.
(8) 6-chloro-3- (2,3,5-trimethyl-6-vinylphenoxy) -4-pyridazinol (Compound No. 2603, Step A-3 and Step A-4)
Dissolve 5.0 mg (0.016 mmol) of 4,6-dichloro-3- (2,3,5-trimethyl-6-vinylphenoxy) pyridazine obtained in (7) in dimethyl sulfoxide (1 mL), and add 10.3 mg of sodium acetate. (0.126 mmol) was added and stirred with heating at 120 ° C. for 2 hours. After cooling to room temperature, the reaction mixture was poured into water, acidified with hydrochloric acid, and extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (developed with ethyl acetate, 1.05744 from MERCK) and 6-chloro-3- ( 1.5 mg (0.0052 mmol, yield 33%) of 2,3,5-trimethyl-6-vinylphenoxy) -4-pyridazinol (Compound No. 2603) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.25 (1H, s), 6.67 (1H, dd, J = 11.0 Hz, 17.6 Hz), 6.56 (1H, s), 5.66 (1H, dd, J = 1.5Hz, 17.6Hz), 5.10 (1H, dd, J = 1.5Hz, 11.0Hz), 2.29 (3H, s), 2.20 (3H, s), 2.04 (3H, s).
Physical properties: amorphous.

(Example 634)
6-Chloro-3- {2- [1- (ethylsulfanyl) ethyl] -3,5,6-trimethylphenoxy} -4-pyridazinol (Compound No. 2606)
(1) 6-chloro-3- {2- [1- (ethylsulfanyl) ethyl] -3,5,6-trimethylphenoxy} -4-methoxypyridazine (Step D-1)
150 mg (0.670 mmol) of 2- [1- (ethylsulfanyl) ethyl] -3,5,6-trimethylphenol obtained in Example 633 (5) was added to 1,4-dioxane (2 mL) and dimethyl sulfoxide (2 mL). In an ice-cooled solution, 93 mg (0.83 mmol) of potassium tert-butoxide was added to the solution, and the mixture was stirred at room temperature for 20 minutes. This mixture was ice-cooled again, 120 mg (0.670 mmol) of 3,6-dichloro-4-methoxypyridazine was added, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was subjected to silica gel chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) and preparative thin layer chromatography (MERCK, Inc., using 1.05744 2 sheets. Hexane: ethyl acetate = 2 2-6 mg (0.0728 mmol, 0.0728 mmol, 6-chloro-3- {2- [1- (ethylsulfanyl) ethyl] -3,5,6-trimethylphenoxy} -4-methoxypyridazine). Yield 10.9%). In addition, 60.0 mg (0.163 mmol, yield 24.3%) of 3-chloro-6- {2- [1- (ethylsulfanyl) ethyl] -3,5,6-trimethylphenoxy} -4-methoxypyridazine was obtained.
(2) 6-chloro-3- {2- [1- (ethylsulfanyl) ethyl] -3,5,6-trimethylphenoxy} -4-pyridazinol (Compound No. 2606, Step D-2)
24.0 mg (0.358 mmol) of 2-hydroxypyridine was dissolved in dimethyl sulfoxide (1 mL), and 41.0 mg (0.366 mmol) of potassium tert-butoxide was added to this solution at room temperature, followed by stirring at room temperature for 20 minutes. To this, 26.7 mg (0.0728 mmol) of 6-chloro-3- {2- [1- (ethylsulfanyl) ethyl] -3,5,6-trimethylphenoxy} -4-methoxypyridazine obtained by (1) Of dimethyl sulfoxide (1 mL) was added and stirred at 60 ° C. After completion of the reaction, the reaction mixture was allowed to cool and poured into water. The mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The obtained residue was purified by preparative thin layer chromatography (Merck, 1.05744, developed with ethyl acetate) to give 6-chloro-3- {2- [1- (ethylsulfanyl) ethyl] -3,5 , 6-trimethylphenoxy} -4-pyridazinol (Compound No. 2606) was obtained in an amount of 6.6 mg (0.019 mmol, yield 26%).
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.20 (2H, s), 6.64 (1H, s), 2.40-2.15 (8H, m), 2.03 (3H, s), 1.40 (3H, d, J = 7.0Hz), 1.24 (1H, m), 1.03 (3H, t, J = 7.3Hz).
Physical properties: amorphous.

(Example 635)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl phthalate (Compound No. 1625) ) And bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] phthalate (Compound No. 2838, Step I)
207 mg (0.726 mmol) of (2,4-dichlorophenyl) (5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl) methanone was suspended in acetonitrile (3 mL), and 1,4-diazabicyclo [2.2.2 ] 81.6 mg (0.729 mmol) of octane was added and stirred. To this was added 105 µL (0.729 mmol) of phthaloyl dichloride, and the mixture was stirred at room temperature for 1 hour. And stirred at room temperature for 1 hour and 30 minutes. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Daisogel 1001W, hexane: ethyl acetate, gradient) to give 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4 -Pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl phthalate (Compound No. 1625) 28.0 mg (0.0405 mmol, 5.61% yield) and bis [6-chloro -3- (2-Cyclopropyl-6-methylphenoxy) -4-pyridazinyl] phthalate (Compound No. 2838) was obtained in an amount of 163 mg (0.238 mmol, yield 33.0%).
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl phthalate (Compound No. 1625) ):
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.01-7.96 (1H, m), 7.89-7.68 (3H, m), 7.57 (1H, s), 7.29-7.06 (5H, m), 6.90-6.83 ( 1H, m), 3.71 (3H, s), 2.27 (3H, s), 2.13 (3H, s), 1.82-1.68 (1H, m), 0.77-0.53 (4H, m).
Physical properties: amorphous.
Bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] phthalate (Compound No. 2838):
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.13-8.06 (2H, m), 7.84-7.78 (2H, m), 7.58 (2H, s), 7.15-7.06 (4H, m), 6.90-6.83 ( 2H, m), 2.13 (6H, s), 1.82-1.68 (2H, m), 0.73-0.52 (8H, m).
Physical properties: amorphous.

(Example 636)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl 1,3-benzene Disulfonate (Compound No. 2333) and bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] 1,3-benzenedisulfonate (Compound No. 3755, Step I)
122 mg (0.428 mmol) of (2,4-dichlorophenyl) (5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl) methanone was suspended in acetonitrile (4 mL), and 1,4-diazabicyclo [ 2.2.2] Octane 72.0 mg (0.643 mmol) was added followed by 1,3-benzenedisulfonyl dichloride 117 mg (0.425 mmol) and stirred at room temperature for 30 minutes. The reaction mixture was ice-cooled, 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol 100 mg (0.361 mmol) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane: ethyl acetate, gradient) to give 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) 4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl 1,3-benzenedisulfonate (Compound No. 2333) 135 mg (0.177 mmol, yield 49.0) %) And bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] 1,3-benzenedisulfonate (Compound No. 3755) 38.0 mg (0.0503 mmol, yield 13.9) %)Obtained.
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl 1,3-benzene Disulfonate (Compound No. 2333):
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.67 (1H, t, J = 1.9Hz), 8.40-8.34 (1H, m), 8.31-8.24 (1H, m), 7.86 (1H, t, J = 8.0Hz), 7.56 (1H, s), 7.37 (1H, d, J = 1.9Hz), 7.29-7.23 (1H, m), 7.15-7.00 (3H, m), 6.85-6.78 (1H, m), 3.81 (3H, s), 2.00 (3H, s), 1.94 (3H, s), 1.70-1.52 (1H, m), 0.73-0.45 (4H, m).
Physical properties: amorphous.
Bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] 1,3-benzenedisulfonate (Compound No. 3755):
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 8.77 (1H, dd, J = 1.8Hz, 1.8Hz), 8.41 (2H, dd, J = 7.7Hz, 1.8Hz), 7.88 (1H, t, J = 8.0Hz), 7.48 (2H, s), 7.15-6.95 (4H, m), 6.90-6.75 (2H, m), 1.97 (6H, s), 1.67-1.46 (2H, m), 0.75-0.44 (8H , m).
Physical properties: amorphous.

(Example 637)
Bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] pentanedioate (Compound No. 2746) and 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl pentandioate (Compound No. 2739)
241 mg (0.870 mmol) of 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol is suspended in acetonitrile (8 mL), and 1,4-diazabicyclo [2.2.2] octane 139 mg under ice cooling (1.23 mmol), then 146 mg (0.864 mmol) of pentanedioyl dichloride and 244 mg (0.856 mmol) of (2,4-dichlorophenyl) (5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl) methanone In addition, it was stirred at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was subjected to silica gel column chromatography (Wakogel C-100, hexane: ethyl acetate, gradient) and preparative thin layer chromatography (MERCK, 1.05744, 2 hexanes: ethyl acetate = 2 1 or 1: 1) and bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] pentanedioate (Compound No. 2746) 42.0 mg ( 0.0646 mmol, yield 7.48%) and 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazole As a result, 35.0 mg (0.0532 mmol, yield 6.21%) of 5-yl pentanedioate (Compound No. 2739) was obtained.
Bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] pentanedioate (Compound No. 2746):
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.23 (2H, s), 7.14-7.02 (4H, m), 6.83 (2H, dd, J = 6.6, 2.9Hz), 2.89 (4H, t, J = 7.0Hz), 2.25 (2H, quintet, J = 7.0Hz), 2.10 (6H, s), 1.80-1.65 (2H, m), 0.78-0.52 (8H, m).
Physical properties: candy-like.
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl pentandioate (compound Number 2739):
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.45-7.17 (4H, m), 7.14-7.00 (2H, m), 6.90-6.75 (1H, m), 3.53 (3H, s), 2.83 (2H, t, J = 7.0Hz), 2.57 (2H, t, J = 7.0Hz), 2.20-2.00 (2H, m), 2.11 (3H, s), 2.10 (3H, s), 1.80-1.65 (1H, m ), 0.80-0.50 (4H, m).
Physical properties: amorphous.

(Example 638)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-pyrrolidinecarboxylate (Compound No. 1937)
200 mg (0.722 mmol) of 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol was mixed with toluene (3 mL) and cooled on ice. While stirring in a nitrogen atmosphere, 60 μL (0.742 mmol) of pyridine and then 0.67 mL (0.724 mmol) of a 1.08 mol / L phosgenetoluene solution were added, and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was ice-cooled, 60 μL (0.722 mmol) of pyridine and then 60 μL (0.719 mmol) of pyrrolidine were added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (using MERCK 1.05744 4 plates, developed with hexane: ethyl acetate = 2: 1), and 6-chloro-3- (2 190 mg (0.508 mmol, yield 70.7%) of -cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-pyrrolidinecarboxylate (Compound No. 1937) were obtained.
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.59 (1H, s), 7.15-7.03 (2H, m), 6.90-6.80 (1H, m), 3.62 (2H, dd, J = 6.6Hz, 6.9Hz ), 3.51 (2H, dd, J = 6.9Hz, 6.6Hz), 2.15 (3H, s), 2.05-1.90 (4H, m), 1.88-1.68 (1H, m), 0.80-0.50 (4H, m) .
Melting point (° C): 115-118.

(Example 639)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl methoxy (methyl) carbamate (Compound No. 3564)
200 mg (0.722 mmol) of 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol was mixed with toluene (3 mL) and cooled on ice. While stirring in a nitrogen atmosphere, 60 μL (0.742 mmol) of pyridine and then 0.67 mL (0.724 mmol) of a 1.08 mol / L phosgenetoluene solution were added, and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was ice-cooled, 120 μL (1.48 mmol) of pyridine and then 70.4 mg (0.722 mmol) of N, O-dimethylhydroxylamine hydrochloride were added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane: ethyl acetate, gradient) to give 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) 100 mg (0.275 mmol, yield 38.1%) of 4-pyridazinyl methoxy (methyl) carbamate (Compound No. 3564) was obtained.
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 7.53 (1H, s), 7.15-7.03 (2H, m), 6.90-6.82 (1H, m), 3.84 (3H, s), 3.35 (3H, s) , 2.15 (3H, s), 1.87-1.67 (1H, m), 0.80-0.52 (4H, m).
Melting point (° C): 63-64.5.

(Example 640)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,5-dimethyl-1H-pyrrole-1-carboxylate (Compound No. 3630)
37.4 mg (0.393 mmol) of 2,5-dimethyl-1H-pyrrole was mixed with toluene (1 mL), and while stirring under ice cooling, 40.0 μL (0.407 mmol) of pyridine and then 0.34 mL of 1.08 mol / L phosgene toluene solution ( 0.367 mmol) was added and stirred for 1 hour. To this, 40.0 μL (0.407 mmol) of pyridine and then 100 mg (0.361 mmol) of 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol were added and stirred for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (using MERCK 1.05744, 2 hexanes: ethyl acetate = 2: 1), and 6-chloro-3- (2 24.0 mg (0.0603 mmol, 16.7% yield) of 2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,5-dimethyl-1H-pyrrole-1-carboxylate (Compound No. 3630) was obtained.
¹ H-NMR (200 MHz, CDCl ₃ ) δppm: 8.20-8.03 (1H, m), 7.63 (1H, s), 7.13-7.00 (2H, m), 6.90-6.80 (1H, m), 6.36 (1H, d, J = 2.9Hz), 2.55 (3H, s), 2.22 (3H, s), 2.15 (3H, s), 1.90-1.70 (1H, m), 0.80-0.50 (4H, m).
Melting point (° C): 208-210.

(Example 641)
4-{[4- (Benzoyloxy) -6-chloro-3-pyridazinyl] oxy} -3-methylphenyl benzoate (Compound No. 3850)
(1) 6-chloro-3- (4-hydroxy-2-methylphenoxy) -4-pyridazinol 4-[(4,6-dichloro-3-pyridazinyl) oxy]-obtained in Example 630 (3) Dissolve 173 mg (0.553 mmol) of 3-methylphenyl acetate in 1,4-dioxane (1.4 mL), add 0.7 mL (2.1 mmol) of 3 mol / L sodium hydroxide solution and dimethyl sulfoxide (2.8 mL) overnight at room temperature. Stir. A 4 mol / L aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The obtained residue was purified by preparative thin layer chromatography (developed with dichloromethane: methanol = 36: 1) to give 66.8-chloro-3- (4-hydroxy-2-methylphenoxy) -4-pyridazinol in 66.8. mg was obtained.
(2) 4-{[4- (Benzoyloxy) -6-chloro-3-pyridazinyl] oxy} -3-methylphenyl benzoate (Compound No. 3850)
66.8 mg of 6-chloro-3- (4-hydroxy-2-methylphenoxy) -4-pyridazinol obtained in (1) was dissolved in acetonitrile (1.0 mL), and 1,4-diazabicyclo [2.2.2] octane 60.0 was dissolved. mg (0.536 mmol) and then 61 μL (0.523 mmol) of benzoyl chloride were added and stirred at room temperature for 1 hour 30 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The obtained residue was purified by preparative thin layer chromatography (development with hexane: ethyl acetate = 5: 1), and 4-{[4- (benzoyloxy) -6-chloro-3-pyridazinyl] oxy} There was obtained 36.9 mg (0.0800 mmol, yield of 14.5% from 4-[(4,6-dichloro-3-pyridazinyl) oxy] -3-methylphenyl acetate) (3-methylphenyl benzoate (Compound No. 3850)).
¹ H-NMR (200 MHz, CDCl ₃ ) δ ppm: 8.21-8.17 (4H, m), 7.72-7.48 (7H, m), 7.22-7.07 (3H, m), 2.21 (3H, s).
Melting point (° C): 118-120.

(Example 642)
3- (2-Aminophenoxy) -3-chloro-4-pyridazinol (Compound No. 377)
(1) 2-[(6-Chloro-4-methoxy-3-pyridazinyl) oxy] aniline (Step D-1)
670 mg (6.15 mmol) of 2-aminophenol was dissolved in a mixed solvent of 1,4-dioxane (7 mL) and dimethyl sulfoxide (7 mL), and 690 mg (6.16 mmol) of potassium tert-butoxide was added to the solution under ice cooling. Stir for minutes. To this mixture was added 1000 mg (5.59 mmol) of 3,6-dichloro-4-methoxypyridazine, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into ice water, brine was added, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the resulting residue was purified by silica gel chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to give 2-[(6-chloro-4-methoxy-3-pyridazinyl) oxy] 328 mg (1.30 mmol, 23.3% yield) of aniline and 2-[(6-chloro-4-methoxy-3-pyridazinyl) oxy] aniline and 2-[(6-chloro-5-methoxy-3-pyridazinyl) oxy 100 mg of a mixture of aniline was obtained.
(2) 3- (2-Aminophenoxy) -3-chloro-4-pyridazinol (Compound No. 377, Step D-2)
20.0 mg (0.198 mmol) of 2-[(6-chloro-4-methoxy-3-pyridazinyl) oxy] aniline obtained in (1) is dissolved in dimethyl sulfoxide (0.4 mL), and 2 mol / L aqueous sodium hydroxide solution is dissolved. (0.2 mL, 0.4 mmol) was added and stirred at room temperature for 5 hours. The reaction mixture was poured into saturated brine and extracted with tetrahydrofuran. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin layer chromatography (developed with dichloromethane: methanol = 10: 1 using 2 MERCK 1.05744) and 3- (2-aminophenoxy) -3-chloro. 17.0 mg (0.0714 mmol, yield 36.1%) of 4-pyridazinol (Compound No. 377) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.50-6.94 (2H, m), 6.90-6.82 (1H, m), 6.85-6.63 (2H, m).
Melting point (° C): 249-250.

(Example 643)
N- {2-[(6-Chloro-4-hydroxy-3-pyridazinyl) oxy] phenyl} acetamide (Compound No. 380)
18.0 mg (0.0756 mmol) of 3- (2-aminophenoxy) -3-chloro-4-pyridazinol obtained in Example 641 was mixed with dichloromethane (0.8 mL) and mixed with 0.050 mL of triethylamine with stirring under ice-cooling. 0.36 mmol) and then 0.010 mL (0.14 mmol) of acetyl chloride were added and stirred at room temperature for 3 hours. The reaction mixture was poured into saturated brine and extracted with tetrahydrofuran. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin layer chromatography (developed with MERCK 1.05715 dichloromethane: methanol = 10: 1), and N- {2-[(6-chloro-4-hydroxy- This gave 3.6 mg (0.0129 mmol, 17.1% yield) of 3-pyridazinyl) oxy] phenyl} acetamide (Compound No. 380).
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 8.10-8.00 (1H, m), 7.25-7.08 (3H, m), 6.60 (1H. S), 2.12 (3H, s).
Melting point (° C): 135.

(Example 644)
N, N, N-Tributyl-1-butananium 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinolate (Compound No. 3798)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol 105 mg (0.379 mmol) in ethanol (2 mL) was added to a 2 mol / L aqueous sodium hydroxide solution 0.19 mL (0.38 mmol), followed by 106 mg (0.381 mmol) of tetrabutylammonium chloride was added and stirred at 60 ° C. for 5 hours. The reaction mixture was left at room temperature overnight and the solid was removed by filtration. The filtrate was concentrated and 197 mg (0.380 mmol, yield) of N, N, N-tributyl-1-butananium 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinolate (Compound No. 3798) 100%).
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.05-6.95 (2H, m), 6.80-6.73 (1H, m), 6.43 (1H, s), 3.30-3.15 (8H, m), 2.14 (3H , s), 2.00-1.85 (1H, m), 1.76-1.53 (8H, m), 1.50-1.30 (8H, m), 1.02 (12H, t, J = 7.1Hz), 0.78-0.63 (2H, m ), 0.63-0.48 (2H, m).
Melting point (° C): 113-114.

(Example 645)
Sodium 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinolate (Compound No. 3805)
To a solution of 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol 100 mg (0.361 mmol) in ethanol (2 mL) was added 0.18 mL (0.36 mmol) of a 2 mol / L aqueous sodium hydroxide solution, and 50 Stir at 4 ° C. for 4 hours. The reaction mixture was concentrated to obtain 108 mg (0.361 mmol, 100% yield) of sodium 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinolate (Compound No. 3805).
¹ H-NMR (200 MHz, CD ₃ OD) δ ppm: 7.05-6.95 (2H, m), 6.77 (1H, dd, J = 6.4, 3.1 Hz), 6.43 (1H, s), 2.14 (3H, s), 2.00-1.82 (1H, m), 0.78-0.63 (2H, m), 0.63-0.48 (2H, m).
Melting point (° C):> 260.

(Example 646)
5-Bromo-6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol (Compound No. 3843)
To a solution of 157 mg (0.567 mmol) of 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol in N, N-dimethylformamide (2 mL) was added 108 mg (0.607 mmol) of N-bromosuccinimide. The mixture was further stirred at room temperature for 3 hours and 30 minutes. Water and then a 4 mol / L aqueous hydrochloric acid solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by preparative thin layer chromatography (developed with MERCK 1.05744 hexane: ethyl acetate = 2: 1) to give 5-bromo-6-chloro-3- (2-cyclo 123 mg (0.346 mmol, yield 61.0%) of propyl-6-methylphenoxy) -4-pyridazinol (Compound No. 3843) was obtained.
¹ H-NMR (200 MHz, CD ₃ OD) δppm: 7.08-7.05 (2H, m), 6.85-6.80 (1H, m), 2.14 (3H, s), 1.88-1.76 (1H, m), 0.82-0.72 (2H, m), 0.60-0.56 (2H, m).
Physical properties: amorphous.

(Example 647)
3- (2-Allyl-6-methylphenoxy) -6-chloro-4-pyridazinol (Compound No. 835)
¹ H-NMR (270 MHz, CD ₃ OD) δppm: 7.17-7.10 (3H, m), 6.71 (1H, s), 5.95-5.73 (1H, m), 5.00-4.90 (2H, m), 3.26 (1H , d, J = 7.0Hz), 2.12 (3H, s).
Melting point (° C): 126-128.

(Example 648)
6-Chloro-3- (2,6-dimethylphenoxy) -4-pyridazinyl dimethylcarbamate (Compound No. 1889)
¹ H-NMR (500 MHz, CDCl ₃ ) δ ppm: 7.56 (1H, s), 7.09 (3H, s), 3.15 (3H, s), 3.05 (3H, s), 2.13 (6H, s).
Melting point (° C): 149-150.

(Example 649)
6-Chloro-3- (2-methylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3685)
¹ H-NMR (500MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.29-7.22 (2H, m), 7.17 (1H, t, J = 7.6Hz), 7.09 (1H, d, J = 7.6Hz ), 3.77-3.70 (4H, m), 3.70-3.66 (2H, m), 3.62-3.57 (2H, m), 2.19 (3H, s).
Melting point (° C): 124.

(Example 650)
6-chloro-3- (2-isopropylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3686)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.43-7.33 (1H, m), 7.33-7.18 (2H, m), 7.12-7.02 (1H, m), 3.85-3.55 ( 8H, m), 3.08 (1H, m, J = 6.9Hz), 1.21 (6H, d, J = 6.9Hz).
Melting point (° C): 77-78.

(Example 651)
6-chloro-3- (2-cyclopropylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3687)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.58 (1H, s), 7.26-7.13 (2H, m), 7.13-7.05 (1H, m), 7.05-6.98 (1H, m), 3.79-3.63 ( 6H, m), 3.63-3.52 (2H, m), 1.92-1.81 (1H, m), 0.84-0.74 (2H, m), 0.72-0.61 (2H, m).
Physical properties: Pasty.

(Example 652)
6-Chloro-3- (2,3-dihydro-1H-inden-4-yloxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3688)
¹ H-NMR (500MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.19 (1H, t, J = 7.6Hz), 7.13 (1H, d, J = 7.6Hz), 6.94 (1H, d, J = 7.6Hz), 3.77-3.70 (4H, m), 3.70-3.66 (2H, m), 3.62-3.57 (2H, m), 2.97 (2H, t, J = 7.6Hz), 2.74 (2H, t, J = 7.6Hz), 2.06 (2H, quintet, J = 7.6Hz).
Melting point (° C): 136.

(Example 653)
6-Chloro-3- (2,6-dimethylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3689)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.10 (3H, s), 3.80-3.70 (6H, m), 3.62-3.58 (2H, m), 2.12 (6H, s) .
Melting point (° C): 86-87.

(Example 654)
6-Chloro-3- (2,3,5,6-tetramethylphenoxy) -4-pyridazinyl dimethyl carbamate (Compound No. 3894)
¹ H-NMR (500MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 6.90 (1H, s), 3.15 (3H, s), 3.05 (3H, s), 2.23 (6H, s), 2.04 (6H , s).
Melting point (° C): 200 (sublimation).

(Example 655)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl ethoxy (methyl) carbamate (Compound No. 3918)
200 mg (0.722 mmol) of 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol was mixed with toluene (2 mL). While stirring under a nitrogen atmosphere, 150 μL (1.86 mmol) of pyridine and then 0.68 mL (0.734 mmol) of a 1.08 mol / L phosgenetoluene solution were added and stirred at room temperature for 20 minutes. This mixture was mixed with 150 μL of pyridine (1.86 mmol), O-ethyl-N-methylhydroxylamine hydrochloride 80.0 mg {0.717 mmol, Bioorganic & Medicinal Chemistry Letters, 2001, Vol. 11, No. 13. In the mixture of toluene (2 mL), and stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (using MERCK 1.05744 4 plates, developed with hexane: ethyl acetate = 2: 1) to give 6-chloro-3- (2 96.0 mg (0.254 mmol, yield 35.4%) of -cyclopropyl-6-methylphenoxy) -4-pyridazinyl ethoxy (methyl) carbamate (Compound No. 3918) was obtained.
¹ H-NMR (200MHz, CDCl ₃ ) δppm: 7.54 (1H, s), 7.15-7.05 (2H, m), 6.90-6.80 (1H, m), 4.08 (2H, q, J = 7.0Hz), 3.35 (3H, s), 2.15 (3H, s), 1.84-1.65 (1H, m), 1.30 (3H, t, J = 7.0Hz), 0.80-0.55 (4H, m).
Melting point (° C): 82-83.

(Example 656)
6-chloro-3- (2-chlorophenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3920)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.67 (1H, s), 7.50-7.43 (1H, m), 7.36-7.18 (3H, m), 3.85-3.67 (6H, m), 3.67-3.55 ( 2H, m).
Melting point (° C): 108-113.

(Example 657)
6-Chloro-3- (2,5-dimethylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3939)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.14 (1H, d, J = 7.6 Hz), 6.98 (1H, d, J = 7.9 Hz), 6.90 (1H, s), 3.74-3.58 (8H, m), 2.31 (3H, s), 2.13 (3H, s).
Melting point (° C): 98-100.

(Example 658)
6-Chloro-3- (2-methoxy-5-methylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3941)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.62 (1H, s), 7.01 (1H, d, J = 8.2Hz), 7.00 (1H, s), 6.88 (1H, d, J = 8.2Hz), 3.85-3.65 (6H, m), 3.71 (3H, s), 3.65-3.55 (2H, m), 2.30 (3H, s).
Melting point (° C): 179-180.

(Example 659)
6-chloro-3- (2-chloro-6-methylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3944)
¹ H-NMR (270MHz, CDCl ₃ ) δppm: 7.65 (1H, s), 7.30-7.10 (3H, m), 3.75 (6H, s), 3.62 (2H, br.d, J = 4.6Hz), 2.23 (3H, s).
Melting point (° C): 90-92.

(Example 660)
3- (2-Bromo-6-methylphenoxy) -6-chloro-4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3946)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.67 (1H, s), 7.45 (1H, d, J = 7.6 Hz), 7.23 (1H, d, J = 7.6 Hz), 7.07 (1H, t, J = 7.6Hz), 3.80-3.73 (6H, m), 3.64-3.60 (2H, m), 2.24 (3H, s).
Physical properties: Pasty.

(Example 661)
6-Chloro-3- (2-ethyl-6-methylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3951)
¹ H-NMR (270MHz, CDCl ₃ ) δppm: 7.56 (1H, s), 7.20-7.07 (3H, m), 3.85-3.56 (8H, m), 2.47 (2H, q, J = 7.6Hz), 2.10 (3H, s), 1.14 (3H, t, J = 7.6Hz).
Melting point (° C): 110-115.

(Example 662)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3963)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.56 (1H, s), 7.05 (2H, s), 3.79-3.73 (4H, m), 3.73-3.67 (2H, m), 3.63-3.65 (2H, m), 2.92 (2H, t, J = 7.6 Hz), 2.67 (2H, t, J = 7.6 Hz), 2.14 (3H, s), 2.05 (2H, quintet, J = 7.6 Hz).
Physical properties: amorphous.

(Example 663)
6-Chloro-3- (2,3,5,6-tetramethylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 3970)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.56 (1H, s), 6.91 (1H, s), 3.78-3.68 (6H, m), 3.62-3.57 (2H, m), 2.23 (6H, s) , 1.98 (6H, s).
Melting point (° C): 185-189.

(Example 664)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1,3-oxazolidine-3-carboxylate (Compound No. 4010)
100 mg (0.361 mmol) of 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol was mixed with toluene (0.4 mL). While stirring, 0.20 mL (0.40 mmol) of 2 mol / L sodium hydroxide aqueous solution was added and stirred for 1 hour. Next, 0.35 mL (0.38 mmol) of a 1.08 mol / L phosgene toluene solution was added, and the mixture was stirred at room temperature for 1 hour. Further, 1,3-oxazolidine 50.0 mg {0.684 mmol, Agricultural and Biological Chemistry, 1991, 55, No. 1, can be produced by the method described on pages 37-43}, Stir at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin layer chromatography (using MERCK 1.05744 2 hexanes: ethyl acetate = 2: 1) to give 6-chloro-3- (2 52.7 mg (0.140 mmol, yield 38.8%) of -cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1,3-oxazolidine-3-carboxylate (Compound No. 4010) was obtained.
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.15-7.08 (2H, m), 6.90-6.83 (1H, m), 5.07 (1H, s), 4.99 (1H, s) , 4.18-4.10 (2H, m), 3.77-3.72 (1H, m), 3.66-3.61 (1H, m), 2.14 (3H, s), 1.81-1.70 (1H, m), 0.78-0.68 (2H, m), 0.65-0.55 (2H, m).
Melting point (° C): 97-98.

Example 665
6-Chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl dimethyl carbamate (Compound No. 3887)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.04 (2H, s), 3.14 (3H, s), 3.05 (3H, s), 2.92 (2H, t, J = 7.6 Hz ), 2.68 (2H, t, J = 7.6 Hz), 2.14 (3H, s), 2.07-2.01 (2H, m).
Melting point (° C): 168-170.

(Example 666)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 1,3-oxazolidine-3-carboxylate (Compound No. 4022)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.04 (2H, s), 5.05 (1H, s), 4.97 (1H, s), 4.14-4.09 (2H, m), 3.72 (1H, t, J = 6.5 Hz), 3.62 (1H, t, J = 6.2 Hz), 2.92 (2H, t, J = 7.2 Hz), 2.67 (2H, t, J = 7.6 Hz), 2.14 (3H , s), 2.07-2.01 (2H, m).
Melting point (° C): amorphous.

(Example 667)
6-Chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 4-methylbenzoate (Compound No. 4030)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 8.08 (2H, d, J = 8.0 Hz), 7.57 (1H, s), 7.33 (2H, d, J = 8.0 Hz), 7.01 (2H, s), 2.90 (2H, t, J = 7.4 Hz), 2.69 (2H, t, J = 7.4 Hz), 2.45 (3H, s), 2.14 (3H, s), 2.08-1.97 (2H, m).
Melting point (° C): amorphous.

(Example 668)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-piperidinyl carbonate (Compound No. 4037)
¹ H-NMR (270MHz, CDCl ₃ ) δppm: 7.57 and 7.55 (1H, s), 7.12-7.06 (2H, m), 6.86-6.82 (1H, m), 3.87-3.28 (5H, m), 2.14 ( 3H, s), 1.93-1.58 (6H, m), 0.77-0.67 (2H, br. M), 0.62-0.53 (2H, br. M).
Melting point (° C): amorphous.

(Example 669)
6-Chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 3-piperidinyl carbonate (Compound No. 4038)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.55 and 7.53 (1H, s), 7.03 (2H, s), 3.87-3.24 (5H, m), 2.91 (2H, t, J = 7.4 Hz), 2.67 (2H, t, J = 7.4 Hz), 2.13 (3H, s), 2.09-1.80 (5H, m), 1.66-1.50 (2H, m).
Melting point (° C): amorphous.

(Example 670)
6-Chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl bis (cyanomethyl) carbamate (Compound No. 4040)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.58 (1H, s), 7.06 (2H, s), 4.46 (2H, s), 4.39 (2H, s), 2.92 (2H, t, J = 7.6 Hz ), 2.66 (2H, t, J = 7.2 Hz), 2.13 (3H, s), 2.07-2.01 (3H, m).
Melting point (° C): amorphous.

(Example 671)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-hydroxy-1-piperidinecarboxylate (Compound No. 4047)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.55-7.24 (1H, m), 7.12-7.05 (2H, m), 6.86-6.80 (1H, br. M), 4.95 (1H, s), 4.00 ( 1H, dd, J = 13.7, 5.3 Hz), 3.94-3.39 (4H, m), 2.14-2.04 (6H, m), 1.80-1.70 (2H, m), 0.74-0.64 (2H, br.m), 0.62-0.52 (2H, br. M).
Melting point (° C): amorphous.

(Example 672)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 3-hydroxy-1-piperidinecarboxylate (Compound No. 4048)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.53-7.20 (1H, m), 7.04-7.02 (2H, m), 4.94 (1H, br. S), 4.09-3.46 (5H, m), 2.97- 2.83 (2H, m), 2.70-2.63 (2H, m), 2.13-1.90 (8H, m), 1.76-1.60 (1H, m).
Melting point (° C): candy-like.

(Example 673)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-hydroxy-1-piperidinecarboxylate (Compound No. 4055)
Ethanol (2 ml) was added to 100.7 mg (0.251 mmol) of 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-oxo-1-piperidinecarboxylate (Compound No. 4079) and iced. Chilled. To this mixture, 5.3 mg (0.14 mmol) of sodium borohydride was added and stirred for 1 hour under ice cooling. To the reaction mixture, brine was added under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (developed with hexane: ethyl acetate = 5: 1 using two 1.05744 manufactured by MERCK) to give 6-chloro-3- (2 91.7 mg (0.227 mmol, yield 90.5%) of -cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-hydroxy-1-piperidinecarboxylate (Compound No. 4055) was obtained.
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.10-7.06 (2H, m), 6.84 (1H, dd, J = 6.9, 3.4 Hz), 3.99-3.90 (2H, m) , 3.88-3.83 (1H, m), 3.48-3.42 (1H, m), 3.35-3.30 (1H, m), 2.14 (3H, s), 1.90-1.87 (2H, m), 1.78-1.72 (1H, m), 1.62-1.56 (2H, m), 0.76-0.68 (2H, br. m), 0.59-0.52 (2H, br. m).
Melting point (° C): amorphous.

(Example 674)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 4-hydroxy-1-piperidinecarboxylate (Compound No. 4056)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.03 (2H, s), 4.00-3.82 (3H, m), 3.49-3.29 (2H, m), 2.91 (2H, t, J = 7.4 Hz), 2.67 (2H, t, J = 7.4 Hz), 2.14 (3H, s), 2.09-1.98 (2H, m), 1.96-1.86 (2H, m), 1.69-1.53 (2H, m ).
Melting point (° C): oil.

(Example 675)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (1-pyrrolidinyl) -1-piperidinecarboxylate (Compound No. 4063)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.563 and 7.561 (1H, s), 7.12-7.05 (2H, m), 6.89-6.81 (1H, m), 4.26-4.10 (2H, m), 3.24- 3.14 (1H, m), 3.11-3.00 (1H, m), 2.65-2.50 (4H, m), 2.36-2.18 (1H, m), 2.14 (3H, s), 2.02-1.92 (2H, m), 1.85-1.70 (5H, m), 1.67-1.52 (2H, m), 0.76-0.68 (2H, m), 0.61-0.53 (2H, m).
Melting point (° C.): Paste.

(Example 676)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 4- (1-pyrrolidinyl) -1-piperidinecarboxylate (Compound No. 4064)
¹ H-NMR (270MHz, CDCl ₃ ) δppm: 7.55 and 7.54 (1H, s), 7.03 (2H, s), 4.25-4.08 (2H, m), 3.23-3.13 (1H, m), 3.10-3.00 ( 1H, m), 2.91 (2H, t, J = 7.4 Hz), 2.67 (1H, t, J = 7.4 Hz), 2.61-2.53 (4H, m), 2.32-2.21 (1H, m), 2.13 (3H , s), 2.08-1.90 (5H, m), 1.84-1.74 (4H, m), 1.67-1.52 (2H, m).
Melting point (° C.): Paste.

(Example 677)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (methoxyimino) -1-piperidinecarboxylate (Compound No. 4071)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-oxo-1-piperidinecarboxylate (Compound No. 4079) in 55.8 mg (0.139 mmol) to 1,4-dioxane (1 ml) , Methanol (1 ml) and water (0.6 ml) were added. To this mixture, 24.2 mg (0.29 mmol) of O-methyl-hydroxylamine hydrochloride was added and stirred at room temperature for 4 hours. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off, and 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (methoxyimino) -1-piperidinecarboxylate ( 60.9 mg (0.141 mmol, yield 101%) of Compound No. 4071) was obtained.
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.11-7.06 (2H, m), 6.85 (1H, dd, J = 6.9, 2.7 Hz), 3.85 (3H, s), 3.83 (1H, t, J = 6.2 Hz), 3.78 (1H, t, J = 5.8 Hz), 3.71 (1H, t, J = 5.8 Hz), 3.67 (1H, t, J = 6.2 Hz), 2.70-2.67 (2H, m), 2.50-2.45 (2H, m), 2.14 (3H, s), 1.78-1.72 (1H, m), 0.72 (2H, br.d, J = 7.6 Hz), 0.58 (2H, br d, J = 4.1 Hz).
Melting point (° C): oil.

(Example 678)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 4- (methoxyimino) -1-piperidinecarboxylate (Compound No. 4072)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.54 (1H, s), 7.04 (2H, s), 3.85 (3H, s), 3.81 (1H, t, J = 5.5 Hz), 3.76 (1H, t , J = 5.8 Hz), 3.71 (1H, t, J = 6.2 Hz), 3.66 (1H, t, J = 6.2 Hz), 2.92 (2H, t, J = 7.6 Hz), 2.68-2.65 (4H, m ), 2.47 (2H, q, J = 6.9 Hz), 2.14 (3H, s), 2.07-2.01 (2H, m).
Melting point (° C): oil.

(Example 679)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-oxo-1-piperidinecarboxylate (Compound No. 4079)
21-5.5 mg (0.779 mmol) 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol was mixed with toluene (3 mL). While stirring, 0.32 mL (0.96 mmol) of 3 mol / L sodium hydroxide aqueous solution was added and stirred for 30 minutes. Next, 0.82 mL (0.886 mmol) of a 1.08 mol / L phosgene toluene solution was added, and the mixture was stirred at room temperature for 30 minutes. Furthermore, a mixture of 196.2 mg (1.28 mmol) of 4-piperidinone hydrochloride monohydrate and 0.52 mL (1.6 mmol) of 3 mol / L aqueous sodium hydroxide solution was added, and the mixture was stirred at room temperature for 2 hours 30 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by preparative thin-layer chromatography (development using MERCK 1.05717 4 hexanes: ethyl acetate = 1: 1) to give 6-chloro-3- (2 165.2 mg (0.411 mmol, yield 52.8%) of -cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-oxo-1-piperidinecarboxylate (Compound No. 4079) were obtained.
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.56 (1H, s), 7.13-7.06 (2H, m), 6.88-6.83 (1H, m), 4.01 (2H, t, J = 5.9 Hz), 3.90 (2H, t, J = 6.1 Hz), 2.58 (4H, t, J = 5.8 Hz), 2.14 (3H, s), 1.80-1.70 (1H, m), 0.77-0.69 (2H, br.m), 0.62-0.55 (2H, br. M).
Melting point (° C): oil.

(Example 680)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 4-oxo-1-piperidinecarboxylate (Compound No. 4080)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.05 (2H, s), 3.99 (2H, t, J = 5.8 Hz), 3.89 (2H, t, J = 6.2 Hz), 2.92 (2H, t, J = 7.6 Hz), 2.67 (2H, t, J = 7.2 Hz), 2.57 (4H, q, J = 6.2 Hz), 2.14 (3H, s), 2.07-2.01 (2H, m ).
Melting point (° C): oil.

(Example 681)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-acetyl-1-piperazinecarboxylate (Compound No. 4081)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.57 and 7.53 (1H, s), 7.12-7.07 (2H, m), 6.86-6.84 (1H, m), 3.75-3.65 (4H, m), 3.63- 3.53 (4H, m), 2.14 (3H, s), 2.12 (3H, s), 1.77-1.71 (1H, m), 0.74-0.70 (2H, m), 0.60-0.55 (2H, m).
Melting point (° C.): Paste.

(Example 682)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 4-acetyl-1-piperazinecarboxylate (Compound No. 4088)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.56 and 7.52 (1H, s), 7.04 (2H, s), 3.75-3.65 (4H, m), 3.63-3.55 (4H, m), 2.92 (2H, t, J = 7.2 Hz), 2.66 (2H, t, J = 7.6 Hz), 2.13 (3H, s), 2.11 (3H, s), 2.07-2.01 (2H, m).
Melting point (° C.): Paste.

(Example 683)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (4-morpholinylcarbonyl) -1-piperazinecarboxylate (Compound No. 4095)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.56 (1H, s), 7.13-7.08 (2H, m), 6.87-6.83 (1H, m), 3.77-3.61 (8H, m), 3.36-3.28 ( 8H, m), 2.14 (3H, s), 1.79-1.67 (1H, m), 0.78-0.68 (2H, br. M), 0.60-0.54 (2H, br. M).
Melting point (° C): 134-135.

(Example 684)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 4- (4-morpholinylcarbonyl) -1-piperazinecarboxylate (compound Number 4096)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.54 (1H, s), 7.04 (2H, s), 3.70-3.60 (8H, m), 3.36-3.28 (8H, m), 2.92 (2H, t, J = 7.4 Hz), 2.66 (2H, t, J = 7.4 Hz), 2.13 (3H, s), 2.09-1.98 (2H, m).
Melting point (° C): amorphous.

Example 685
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinylethyl 1,4-piperazine dicarboxylate (Compound No. 4103)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.12-7.07 (2H, m), 6.85 (1H, dd, J = 6.9, 2.1 Hz), 4.17 (3H, q, J = 7.1 Hz), 3.74-3.67 (2H, br.m), 3.65-3.54 (6H, br.m), 2.14 (3H, s), 1.77-1.71 (1H, m), 1.28 (2H, t, J = 7.2 Hz), 0.75-0.69 (2H, br. M), 0.61-0.55 (2H, br.m).
Melting point (° C): oil.

(Example 686)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl ethyl 1,4-piperazine dicarboxylate (Compound No. 4104)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.53 (1H, s), 7.04 (2H, s), 4.17 (2H, q, J = 7.1 Hz), 3.73-3.63 (2H, br. M), 3.57 (6H, br. S), 2.92 (2H, t, J = 7.4 Hz), 2.66 (2H, t, J = 7.4 Hz), 2.13 (3H, s), 2.09-1.98 (2H, m), 1.28 ( 3H, t, J = 7.0 Hz).
Melting point (° C): amorphous.

(Example 687)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-cyano-1-piperazinecarboxylate (Compound No. 4111)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.53 (1H, s), 7.14-7.06 (2H, m), 6.87-6.83 (1H, m), 3.82 (2H, br. S), 3.71 (2H, br) s), 3.35-3.31 (4H, m), 2.13 (3H, s), 1.77-1.67 (1H, m), 0.76-0.68 (2H, br.m), 0.63-0.55 (2H, br. m) ).
Melting point (° C): 147-149.

Example 688 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl 1,4-piperazine dicarboxylate (Compound No. 4119)
While stirring a mixture of 1,4-piperazine dicarbonyl dichloride 111 mg (0.526 mmol) and acetonitrile (3 ml), (2,4-dichlorophenyl) (5-hydroxy-1,3-dimethyl-1H-pyrazole-4 -Il) methanone 151 mg (0.530 mmol) was added followed by 1,4-diazabicyclo [2.2.2] octane 60.0 mg (0.535 mmol) and the mixture was stirred at room temperature for 2 hours. To this mixture was added 147 mg (0.549 mmol) of 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol, followed by 60.0 mg (0.535 mmol) of 1,4-diazabicyclo [2.2.2] octane And stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was subjected to silica gel column chromatography (Daisogel 1001W, hexane (0.1 L) ⇒ hexane: ethyl acetate (1: 1, 1 L) ⇒ hexane: ethyl acetate (2: 3, 1 L) ⇒Elution with ethyl acetate (1 L) and fractionation into 197 fractions). Fractions 46 to 95 were combined and concentrated to give 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4- (2,4-dichlorobenzoyl) -1,3-dimethyl 168 mg (0.240 mmol, yield 45.6%) of 1H-pyrazol-5-yl 1,4-piperazine dicarboxylate (Compound No. 4119) was obtained.
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.56 and 7.54 (1H, s), 7.44 (1H, s), 7.32-7.25 (2H, m), 7.12-7.08 (2H, m), 6.88-6.84 ( 1H, m), 3.79 (2H, br.s), 3.68 (2H, br.s), 3.64 (3H, s), 3.59-3.55 (4H, m), 2.14 (3H, s), 2.13 (3H, s), 1.78-1.68 (1H, m), 0.75-0.70 (2H, br. m), 0.62-0.56 (2H, br. m).
Melting point (° C): amorphous.

Example 689
Bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] 1,4-piperazine dicarboxylate (Compound No. 4127)
While stirring a mixture of 1,4-piperazine dicarbonyl dichloride 111 mg (0.526 mmol) and acetonitrile (3 ml), (2,4-dichlorophenyl) (5-hydroxy-1,3-dimethyl-1H-pyrazole-4 -Il) methanone 151 mg (0.530 mmol) was added followed by 1,4-diazabicyclo [2.2.2] octane 60.0 mg (0.535 mmol) and the mixture was stirred at room temperature for 2 hours. To this mixture was added 147 mg (0.549 mmol) of 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol, followed by 60.0 mg (0.535 mmol) of 1,4-diazabicyclo [2.2.2] octane And stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was subjected to silica gel column chromatography (Daisogel 1001W, hexane (0.1 L) ⇒ hexane: ethyl acetate (1: 1, 1 L) ⇒ hexane: ethyl acetate (2: 3, 1 L) ⇒Elution with ethyl acetate (1 L) and fractionation into 197 fractions). Fractions 14 to 21 were combined and concentrated to give bis [6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl] 1,4-piperazine dicarboxylate (Compound No. 4127) 93.2 mg (0.135 mmol, yield 25.7%) was obtained.
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.53 (1H, s) 7.12-7.06 (4H, m), 6.86-6.83 (2H, m), 3.82 (4H, s), 3.70 (4H, s), 2.13 (6H, s), 1.76-1.69 (2H, m), 0.74-0.68 (4H, br. M), 0.61-0.53 (4H, br. M).
Melting point (° C): amorphous.

(Example 690)
3-[(5-Bromo-2,3-dihydro-1H-inden-4-yl) oxy] -6-chloro-4-pyridazinyl 4-morpholinecarboxylate (Compound No. 4130)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.66 (1H, s), 7.38 (1H, d, J = 8.2 Hz), 7.02 (1H, d, J = 8.2 Hz), 3.78-3.75 (6H, m ), 3.60 (2H, t, J = 4.5 Hz), 2.94 (2H, t, J = 7.6 Hz), 2.80 (2H, t, J = 7.2 Hz), 2.12-2.04 (2H, m).
Melting point (° C): amorphous.

(Example 691)
5,6-Dichloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate (Compound No. 4136)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.14-7.06 (2H, m), 6.86-6.83 (1H, m), 3.80-3.70 (4H, m), 3.68-3.60 (4H, m), 2.14 ( 3H, s), 1.82-1.72 (1H, m), 0.80-0.72 (2H, br. M), 0.65-0.55 (2H, br. M).
Melting point (° C.): Gummy.

(Example 692)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-methyl-4-morpholinecarboxylate (Compound No. 4146)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.13-7.08 (2H, m), 6.87-6.83 (1H, m), 4.10-3.93 (3H, m), 3.71-3.59 ( 2H, m), 3.32-3.06 (1H, m), 2.92 and 2.76 (1H, t, J = 11.9 Hz), 2.14 (3H, s), 1.80-1.69 (1H, m), 1.22 (3H, d, J = 6.1 Hz), 0.77-0.67 (2H, br. M), 0.63-0.53 (2H, br. M).
Melting point (° C): oil.

(Example 693)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3-methyl-4-morpholinecarboxylate (Compound No. 4154)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.55 (1H, s), 7.13-7.06 (2H, m), 6.88-6.83 (1H, m), 4.25 (1H, br. S), 3.96-3.80 ( 2H, m), 3.76-3.66 (2H, m), 3.60-3.30 (2H, m), 2.14 (3H, s), 1.80-1.70 (1H, m), 1.41 (3H, br.s), 0.76- 0.68 (2H, br. M), 0.61-0.55 (2H, br. M).
Melting point (° C): oil.

(Example 694)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 3-methyl-4-morpholinecarboxylate (Compound No. 4155)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.54 (1H, s), 7.04 (2H, s), 4.24 (1H, br. S), 3.96-3.92 (2H, m), 3.75-3.65 (2H, m), 3.59-3.44 (2H, m), 2.92 (2H, t, J = 7.4 Hz), 2.67 (2H, t, J = 7.5 Hz), 2.14 (3H, s), 2.09-1.98 (2H, m ), 1.39 (3H, br. S).
Melting point (° C): oil.

(Example 695)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,2-dimethyl-1,3-oxazolidine-3-carboxylate (Compound No. 4162)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.95 and 7.83 (1H, s), 7.11-7.09 (2H, m), 6.89-6.84 (1H, m), 4.06 (2H, t, J = 6.3 Hz) , 3.82 and 3.68 (2H, t, J = 6.3 Hz), 2.12 (3H, s), 1.85-1.72 (1H, m), 1.70 and 1.57 (6H, s), 0.77-0.68 (2H, br. M) , 0.60-0.50 (2H, br. M).
Melting point (° C): oil.

(Example 696)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 2,2-dimethyl-1,3-oxazolidine-3-carboxylate (compound Number 4163)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.69 and 7.56 (1H, s), 7.04 (2H, s), 4.06 (2H, t, J = 6.3 Hz), 3.79 and 3.71 (2H, t, J = 6.3 Hz), 2.92 (2H, t, J = 7.3 Hz), 2.67 (2H, t, J = 7.3 Hz), 2.14 (3H, s), 2.09-1.98 (2H, m), 1.69 and 1.61 (6H, s).
Melting point (° C): amorphous.

(Example 697)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2-oxo-1,3-oxazolidine-3-carboxylate (Compound No. 4170)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.06-6.98 (2H, m), 6.83-6.74 (1H, m), 6.53 (1H, s), 4.51 and 4.41 (2H, t, J = 7.9 Hz) , 4.20 and 3.47 (2H, t, J = 7.9 Hz), 2.05 (3H, s), 1.82-1.72 (1H, m), 0.77-0.68 (2H, br.m), 0.58-0.48 (2H, m) .
Melting point (° C): amorphous.

(Example 698)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4,4-dimethyl-1,3-oxazolidine-3-carboxylate (Compound No. 4178)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.70 and 7.56 (1H, s), 7.10-7.07 (2H, m), 6.89-6.82 (1H, m), 5.13 and 5.07 (2H, s), 3.88 and 3.84 (2H, s), 2.14 (3H, s), 1.80-1.70 (1H, m), 1.57 and 1.50 (6H, s), 0.77-0.67 (2H, br.m), 0.63-0.53 (2H, br m).
Melting point (° C): candy-like.

(Example 699)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 4,4-dimethyl-1,3-oxazolidine-3-carboxylate (compound Number 4179)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.67 and 7.55 (1H, s), 7.04 (2H, s), 5.11 and 5.06 (2H, s), 3.87 and 3.83 (2H, s), 2.92 (2H, t, J = 7.3 Hz), 2.67 (2H, t, J = 7.3 Hz), 2.14 (3H, s), 2.09-2.01 (2H, m), 1.55 and 1.50 (6H, s).
Melting point (° C): amorphous.

(Example 700)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,5-dihydro-1H-pyrrole-1-carboxylate (Compound No. 4186)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.60 (1H, s), 7.11-7.07 (2H, m), 6.85 (1H, dd, J = 6.2, 2.7 Hz), 5.88 (1H, dt, J = 6.2, 2.1 Hz), 5.85 (1H, dt, J = 6.2, 2.1 Hz), 4.45-4.42 (2H, m), 4.33-4.30 (2H, m), 2.15 (3H, s), 1.81-1.75 (1H m), 0.73 (2H, br. d, J = 8.2 Hz), 0.58 (2H, br. d, J = 4.8 Hz).
Melting point (° C): oil.

(Example 701)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 2,5-dihydro-1H-pyrrole-1-carboxylate (Compound No. 4187 )
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.59 (1H, s), 7.06-7.02 (2H, m), 5.86 (2H, dtd, J = 20.6, 4.5, 2.3 Hz), 4.43-4.40 (2H, m), 4.32-4.30 (2H, m), 2.92 (2H, t, J = 7.2 Hz), 2.68 (2H, t, J = 7.6 Hz), 2.15 (3H, s), 2.07-2.01 (2H, m ).
Melting point (° C): oil.

(Example 702)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,6-dihydro-1 (2H) -pyridinecarboxylate (Compound No. 4194)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.60 (1H, s), 7.11-7.07 (2H, m), 6.86-6.85 (1H, m), 5.94-5.87 (1H, m), 5.75-5.68 ( 1H, m), 4.19 (1H, t, J = 2.7 Hz), 4.06 (1H, t, J = 2.7 Hz), 3.78 (1H, t, J = 5.5 Hz), 3.66 (1H, t, J = 5.8 Hz), 2.30-2.23 (2H, br.m), 2.15 (3H, s), 1.79-1.73 (1H, m), 0.75-0.69 (2H, br.m), 0.60-0.55 (2H, br.m) ).
Melting point (° C): 93-96.

(Example 703)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 3,6-dihydro-1 (2H) -pyridinecarboxylate (Compound No. 4195 )
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.57 (1H, s), 7.03 (2H, s), 5.96-5.83 (1H, m), 5.74-5.66 (1H, m), 4.16 (1H, br. s), 4.04 (1H, br.s), 3.75 (1H, t, J = 5.7 Hz), 3.65 (1H, t, J = 5.7 Hz), 2.91 (2H, t, J = 7.3 Hz), 2.68 ( 2H, t, J = 7.3 Hz), 2.25 (2H, br. S), 2.14 (3H, s), 2.09-1.98 (2H, m).
Melting point (° C): candy-like.

(Example 704)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1,4-oxazepan-4-carboxylate (Compound No. 4202)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.55 and 7.54 (1H, s), 7.13-7.06 (2H, m), 6.87-6.83 (1H, m), 3.86-3.74 (6H, m), 3.72- 3.64 (2H, m), 2.14 (3H, s), 2.08-1.95 (2H, m), 1.81-1.70 (1H, m), 0.79-0.67 (2H, m), 0.62-0.53 (2H, m).
Melting point (° C.): Paste.

(Example 705)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1-indoline carboxylate (Compound No. 4210)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.85 (0.8H, d, J = 8.2 Hz), 7.80-7.75 (0.4H, m), 7.65 (0.8H, s), 7.27-7.05 (5H, m ), 6.87-6.83 (1H, m), 4.30 (1.6H, t, J = 8.2 Hz), 4.18 (0.4H, t, J = 8.2 Hz), 3.26-3.20 (2H, m), 2.16 (3H, s), 1.81-1.76 (1H, m), 0.75-0.70 (2H, m), 0.60-0.55 (2H, m).
Melting point (° C): 172-173.

(Example 706)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 1-indoline carboxylate (Compound No. 4211)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.86 (0.8H, d, J = 7.9 Hz), 7.78-7.72 (0.4H, m), 7.64 (0.8H, s), 7.28-7.02 (5H, m ), 4.28 (1.6H, t, J = 8.6 Hz), 4.18 (0.4H, t, J = 8.7 Hz), 3.25 (2H, t, J = 8.3 Hz), 2.91 (2H, t, J = 7.3 Hz) ), 2.69 (2H, t, J = 7.4 Hz), 2.15 (3H, s), 2.09-1.98 (2H, m).
Melting point (° C): 185-189.

(Example 707)
6-Chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 1,3-dihydro-2H-isoindole-2-carboxylate (Compound No. 4218)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.66 and 7.65 (1H, s), 7.38-7.24 (4H, m), 7.13-7.06 (2H, m), 6.88-6.81 (1H, m), 4.99 ( 2H, s), 4.87 (2H, s), 2.17 (3H, s), 1.85-1.75 (1H, m), 0.79-0.70 (2H, m), 0.62-0.54 (2H, m).
Melting point (° C): amorphous.

(Example 708)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 1,3-dihydro-2H-isoindole-2-carboxylate (compound no. 4219)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.64 and 7.63 (1H, s), 7.34-7.25 (4H, m), 7.03 (2H, s), 4.97 (2H, s), 4.86 (2H, s) , 2.91 (2H, t, J = 7.4 Hz), 2.70 (2H, t, J = 7.4 Hz), 2.16 (3H, s), 2.09-1.98 (2H, m).
Melting point (° C.): Paste.

(Example 709)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 3,4-dihydro-1 (2H) -quinolinecarboxylate (Compound No. 4226)
¹ H-NMR (500 MHz, CDCl ₃ ) δppm: 7.78 (1H, br. S), 7.54 (1H, br. S), 7.19-7.14 (2H, m), 7.11-7.07 (3H, m), 6.85 ( 1H, dd, J = 6.2, 2.7 Hz), 3.94 (2H, br.s), 2.84 (2H, t, J = 6.5 Hz), 2.16 (3H, s), 2.06 (2H, quintet, J = 2.1 Hz ), 1.80-1.74 (1H, m), 0.72 (2H, br. D, J = 8.2 Hz), 0.58 (2H, br. D, J = 4.8 Hz).
Melting point (° C): amorphous.

(Example 710)
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 3,4-dihydro-1 (2H) -quinolinecarboxylate (Compound No. 4227 )
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.75 (1H, br. S), 7.53 (1H, br. S), 7.21-7.04 (5H, m), 4.00-3.87 (2H, br. M), 2.92 (2H, t, J = 7.5 Hz), 2.84 (2H, t, J = 6.6 Hz), 2.69 (2H, t, J = 7.4 Hz), 2.15 (3H, s), 2.10-1.99 (4H, m ).
Melting point (° C): oil.

(Example 711)
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate (Compound No. 4234)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.96 (1H, br. S), 7.57 (1H, br. S), 7.13-7.05 (3H, m), 6.94-6.83 (3H, m), 4.36 ( 2H, t, J = 4.5 Hz), 4.10 (2H, br.s), 2.15 (3H, s), 1.80-1.70 (1H, m), 0.75-0.68 (2H, br.m), 0.60-0.54 ( 2H, br. M).
Melting point (° C): amorphous.

(Example 712)
6-Chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 2,3-dihydro-4H-1,4-benzoxazine-4-carboxy Rate (Compound No. 4235)
¹ H-NMR (270 MHz, CDCl ₃ ) δppm: 7.96 (1H, br. S), 7.56 (1H, br. S), 7.11-7.04 (3H, m), 6.95-6.90 (2H, m), 4.36 ( 2H, t, J = 4.5 Hz), 4.16-4.08 (2H, m), 2.92 (2H, t, J = 7.5 Hz), 2.68 (2H, t, J = 7.4 Hz), 2.14 (3H, s), 2.10-1.99 (2H, m).
Melting point (° C): oil.

  Compound Nos. 1 and 6 can be produced according to the method of Example 2.

  Compound Nos. 123-127, 130-138, 144, 145, 151, 163, 173, 184, 202, 217, 226, 249, 264, 265, 266, 267, 269-275, 279, 280, 284, 287, 288, 292, 293, 300, 304, 305, 306, 307, 308, 309, 311, 315, 324, 325, 329, 330, 334, 336, 339, 344, 348, 349, 355, 356, 359, 361, 362, 364-370, 375, 376, 379, 383, 385-387, 390, 391, 396, 399-401, 403, 410, 412, 413, 415-425, 426, 427, 430, 432 438, 441, 443, 446, 450, 453, 454, 456, 58-460, 472, 491, 498, 503, 505, 506, 507, 510, 513, 514, 520, 521, 527-529, 531, 532, 534-536, 538-541, 544, 547, 549, 552, 556, 557, 558, 559, 562, 566, 567, 571, 614, 618, 621, 623, 626 to 629, 635, 640, 642, 650, 653, 658, 659, 662 to 664, 667, 679, 680, 692, 700, 701, 702, 707-712, 716, 717, 719, 731-733, 734, 735-737, 740, 746, 754, 756, 758, 759, 762, 775, 778, 780 to 782, 802 to 804, 834, 835, 844 to 846, 8 0, 890, 894, 896, 911, 914, 931, 964, 965, 979, 982, 987, 998, 1000, 1007, 1009, 1013, 1016, 1020, 1023, 1027, 1040, 1050, 1052, 1053, 1055, 1058, 1060, 1061, 1063, 1064, 1066, 1069, 1073, 1080, 1083, 1086, 1088, 1089, 1091, 1096, 1099, 1100, 1102, 1115, 1118-1120, 1122-1125, 1129, 1133, 2519, 2547, 2548, 2565, 2568, 2570, 2571, 2574, 2577, 2585, 2587, 2589, 2592, 2597, 2599, 2600, 2601, 2605, 260 The compounds of Nos. 7, 2608, 2609 and 2614 can be produced according to the method described in Example 1, Example 6, Example 13, Example 16, Example 21, Example 22 or Example 23.

  Compound Nos. 1140, 1151, 1160, 1172, 1178, 1184, 1207, 1251, 1260, 1266, 1286, 1298, 1334, 1340, 1358, 1364, 1382, 1387, 1391, 1396, 1417, 1441, 1446, 1448, 1450, 1455-1459, 1461, 1481, 1509, 1522, 1531, 1537, 1543, 1549, 1553, 1554, 1566, 1575, 1593, 1599, 1603, 1616, 1643, 1649, 1658, 1706, 1710, 1757, 1770, 1789, 1811, 1840, 1877, 1879, 1881, 1898, 1924, 1981, 1985, 2010, 2034, 2038, 2040, 2042, 205 , 2060, 2066, 2072, 2106, 2136, 2147, 2151, 2176, 2198-2200, 2212, 2220-2224, 2230-2232, 2234-2238, 2240, 2245-2249, 2263, 2265, 2287, 2289, 2300 , 2309, 2315, 2321, 2351, 2662, 2671, 2677, 2697, 2703, 2709, 2715, 2721, 2727, 2752, 2758, 2764, 2770, 2776, 2782, 2788, 2805, 2814, 2820, 2826, 2850 , 2856, 2862, 2868, 2874, 2880, 2900, 2906, 2918, 2924, 2930, 2961, 2970, 2976, 2982, 2988, 2994, 3 16, 3022, 3028, 3034, 3040, 3046, 3052, 3058, 3064, 3070, 3076, 3082, 3088, 3094, 3100, 3106, 3112, 3129, 3138, 3144, 3150, 3156, 3162, 3168, 3185, 3194, 3200, 3217, 3226, 3243, 3252, 3258, 3264, 3270, 3276, 3282, 3288, 3294, 3300, 3306, 3312, 3318, 3324, 3330, 3336, 3342, 3348, 3354, 3360, 3366, 3372, 3378, 3384, 3390, 3396, 3402, 3408, 3414, 3420, 3426, 3432, 3438, 3444, 3450, 3456, 3462, 3468, Compounds Nos. 3474, 3480, 3486, 3492, 3498, 3504, 3510, 3516, 3780, 3786, 3792, 3856 and 4030 can be prepared according to the method described in Example 26, Example 27 or Example 28. .

  The compound of Compound No. 2402 can be produced according to the method described in Example 33.

  Compounds Nos. 2418 and 2431 can be produced according to the method described in Example 1, Example 6 or Example 22.

  Compound No. 2478 can be produced according to the method described in Example 35, Example 36, Example 37, Example 39 or Example 40.

  The compound of Compound No. 2492 can be produced according to the method described in Example 41.

  Compounds Nos. 1620, 1631, 2827 and 3001 can be produced according to the method described in Example 635.

  Compound Nos. 1889, 1891, 1911, 1920, 1946, 1952, 1958, 3522, 3528, 3534, 3540, 3546, 3552, 3558, 3570, 3576, 3582, 3588, 3594, 3600, 3606, 3612, 3618, 3624, 3636, 3642, 3648, 3654, 3660, 3666, 3672, 3678, 3684-3690, 3696, 3702, 3708, 3714, 3720, 3877, 3894, 3920, 3939, 3944, 3944, 3946, 3951, 3963, 3970, 4022, 4037, 4038, 4040, 4047, 4048, 4055, 4056, 4063, 4064, 4071, 4072, 4080, 4087, 4088, 4095, 409 4103, 4104, 4111, 4130, 4146, 4154, 4155, 4162, 4163, 4170, 4178, 4179, 4186, 4187, 4194, 4195, 4202, 4210, 4211, 4218, 4219, 4226, 4227, 4234 and 4235. Compound No. can be produced according to the method described in Example 26, Example 27, Example 28, Example 638, Example 639, Example 640, Example 655, Example 664 or Example 679.

  The compound of Compound No. 2327 can be produced according to the method described in Example 636.

  The compound of Compound No. 2733 can be produced according to the method described in Example 637.

  The compound of Compound No. 3811 can be produced according to the method described in Example 645.

  The compounds of Compound Nos. 3837, 3849, and 4136 can be produced according to the method described in Example 646.

  The compound of Compound No. 4056 can be produced according to the method described in Example 673.

  The compound of Compound No. 4072 can be produced according to the method described in Example 677.

  In the following formulation examples, “%” indicates mass%.

(Formulation example 1)
Compound (10 parts by mass) of wettable powder compound number 806, Compound B (2 parts by mass), Carplex # 80D (manufactured by Shionogi & Co., Ltd., 10 parts by mass), Gohsenol GL05-S (manufactured by Nippon Synthetic Chemical Co., Ltd.) , 2 parts by mass), Newcol 291PG (dioctyl sulfosuccinate sodium salt, manufactured by Nippon Emulsifier Co., Ltd., 0.5 parts by mass), Neogen Powder (Daiichi Kogyo Seiyaku Co., Ltd., 5 parts by mass), Radiolite # 200 ( Showa Chemical Industry Co., Ltd., 10 parts by mass) and H derivative (Keiwa Furnace Co., Ltd., 60.5 parts by mass) were thoroughly mixed. The mixture was pulverized with an air mill (SK-JET O MIZER model 0101, manufactured by Seishin Enterprise Co., Ltd.) to obtain a mixed wettable powder of Compound No. 806 (10%) and Compound B (2%).

(Formulation example 2)
Compound (10 parts by mass) of wettable powder compound number 736, Compound C (2 parts by mass), Carplex # 80D (manufactured by Shionogi & Co., Ltd., 10 parts by mass), Gohsenol GL05-S (manufactured by Nippon Synthetic Chemical Co., Ltd.) , 2 parts by mass), Newcol 291PG (dioctyl sulfosuccinate sodium salt, manufactured by Nippon Emulsifier Co., Ltd., 0.5 parts by mass), Neogen Powder (Daiichi Kogyo Seiyaku Co., Ltd., 5 parts by mass), Radiolite # 200 ( Showa Chemical Industry Co., Ltd., 10 parts by mass) and H derivative (Keiwa Furnace Co., Ltd., 60.5 parts by mass) were thoroughly mixed. The mixture was pulverized with an air mill (SK-JET O MIZER model 0101, manufactured by Seishin Enterprise Co., Ltd.) to obtain a mixed wettable powder of Compound No. 736 (10%) and Compound C (2%).

(Formulation example 3)
Wetting agent Compound No. 506 (8 parts by mass), Compound B (2 parts by mass), Compound C (2 parts by mass), Carplex # 80D (manufactured by Shionogi & Co., Ltd., 10 parts by mass) , Gohsenol GL05-S (Nippon Synthetic Chemical Co., Ltd., 2 parts by mass), New Coal 291PG (Dioctylsulfosuccinate sodium salt, Nippon Emulsifier Co., Ltd., 0.5 parts by mass), Neogen Powder (Daiichi Kogyo Seiyaku Co., Ltd. Manufactured, 5 parts by mass), Radiolite # 200 (manufactured by Showa Chemical Industry Co., Ltd., 10 parts by mass) and H derivative (manufactured by Keiwa Furnace Co., Ltd., 60.5 parts by mass) were sufficiently mixed. Grind the mixture with an air mill (SK-JET O MIZER model 0101, manufactured by Seishin Enterprise Co., Ltd.), and mix compound No. 506 (8%), Compound B (2 parts by mass), and Compound C (2%) A wettable powder was obtained.

(Formulation example 4)
30 parts by mass of the granule compound (B), 1 part by mass of New Coal 291PG, and 69 parts by mass of water were mixed and pulverized to a particle size of about 5 μm with an attritor (Mitsui Mine Co., Ltd.) to obtain a slurry. 1 part by mass of Toxanone (manufactured by Sanyo Chemical Co., Ltd.) and 1 part by mass of water were added to 98 parts by mass of the slurry, and mixed to obtain slurry 2. Compound No. 1566 1 part by mass, sodium tripolyphosphate (manufactured by Mitsui Chemicals) 2 parts by mass, 1 (dextrin, Nippon Starch Chemical Co., Ltd.) 1.5 parts by mass, bentonite (Toyoshun Mining Co., Ltd.) 25 parts by mass, calcium carbonate Calphine 600 (Adachi Lime Co., Ltd.) 67.1 parts by mass In the FM-NW-5 type manufactured by Fuji Sangyo Co., Ltd.), 3.4 parts by mass of slurry 2 is added and mixed. The kneaded product was extruded and granulated using Dome Gran (Fuji Paudal Co., Ltd., screen 1.0 mmφ). The obtained granulated product was dried with a shelf dryer (manufactured by Tabai Co., Ltd., PERFECT OVEN PS-222 type, 60 ° C.) and then sieved to 600 to 1190 μm to obtain compound 1% of compound number 1566. A mixed granule of 1% of compound (B) was obtained.

(Formulation example 5)
Aqueous Suspension Compound No. 3690 (10 parts by mass), Compound B (10 parts by mass), New Coal 291PG (1 part by mass), lignin sulfonate calcium salt (Pearl Rex CP, Nippon Paper Industries Co., Ltd., 10 parts by mass) Part), propylene glycol (made by Nippon Emulsifier Co., Ltd., 10 parts by mass) and water (59 parts by mass), and pulverized in an attritor (Mitsui Mining Co., Ltd.) until the diameter of the solid particles is 5 μm or less A slurry was obtained. To this slurry (20 parts by mass), 0.05% xanthan gum aqueous solution (10 parts by mass), 8 parts by mass of propylene glycol and 68 parts by mass of water were added and mixed, and compound No. 3690 (10%) and Compound B (10%) A mixed aqueous suspension was obtained.

(Test Example 1)
Test of herbicidal effect and phytotoxicity to transplanted rice
After paddy soil was filled in 1 / 5000a Wagner pots, the seeds of Tainubie, firefly, and annual broad-leaved weeds (Azena and Kikashigusa) awakened to dormancy were mixed in 1 cm of the surface layer. In addition, a tuber of Mizugayatsuri, Urikawa and Krogwei awakened from dormancy was planted, and rice seedlings at 2.2 leaf stage were transplanted, submerged, and grown in a greenhouse. Three days after transplantation, the prescribed amount of wettable powder prepared according to Formulation Example 1 was diluted in water and treated with flooded soil, and 25 days later, herbicidal effects and phytotoxicity to transplanted rice were determined according to the following criteria. The results are shown in Table 2. In the table, “-” represents a composition not containing the active ingredient.

Criterion 0: Growth inhibition rate 0-15%
1: Growth inhibition rate 16-35%
2: Growth suppression rate 36-55%
3: Growth inhibition rate 56-75%
4: Growth inhibition rate 76-95%
5: Growth suppression rate 96-100%.

(Table 2) Test of herbicidal effect and phytotoxicity to transplanted rice

(Test Example 2)
Test of herbicidal effect and phytotoxicity to transplanted rice
After paddy soil was filled in 1 / 5000a Wagner pots, the seeds of Tainubie, firefly, and annual broad-leaved weeds (Azena and Kikashigusa) awakened to dormancy were mixed in 1 cm of the surface layer. In addition, a tuber of Mizugayatsuri, Urikawa and Krogwei awakened from dormancy was planted, and rice seedlings at 2.2 leaf stage were transplanted, submerged, and grown in a greenhouse. Three days after transplantation, the prescribed amount of wettable powder prepared according to Formulation Example 1 was diluted with water and treated with flooded soil, and 25 days later the herbicidal effect and transplanted rice were examined according to the criteria described in Test Example 1. The results are shown in Table 3. In the table, “-” represents a composition not containing the active ingredient.

(Table 3) Herbicidal effect and phytotoxicity test for transplanted rice

Claims (18)

Formula (I):

[Wherein, R ¹ represents a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₂ -C ₆ alkenyl group, a cyano group, C ₂ -C ₇ alkylcarbonyl group, a di (C ₁ -C ₆ alkyl) carbamoyl group, which may be substituted phenyl group (the substituent is a substituent selected from substituent group a.), 5 or 6-membered heterocyclic group (the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and may further contain 1 to 2 nitrogen atoms), C _1- . A C ₆ alkoxy group, an optionally substituted phenoxy group (the substituent is a substituent selected from the following substituent group A) or an optionally substituted 5- or 6-membered heterocyclic oxy group {the heterocyclic ring is Contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and one or two more Of nitrogen atoms. The substituent is a substituent selected from the group consisting of an optionally substituted benzoyl group (the substituent is a substituent selected from the following substituent group A) and a C _{1 to} C ₆ alkyl group. },
R ² is a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a (C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkyl group, a benzoyl group which may be substituted (the substituent is the following substituent group) A substituent selected from A.), a C ₂ -C ₇ alkoxycarbonyl group, an optionally substituted phenoxy group (the substituent is a substituent selected from the following substituent group A), substituted. A good phenylthio group (the substituent is a substituent selected from the following substituent group A) or a tri (C ₁ -C ₆ alkyl) silicon group;
R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, a halogen atom or an optionally substituted C ₁ -C ₆ alkyl group (the substituent is selected from the following substituent group B) A C ₂ -C ₆ alkenyl group which may be substituted (the substituent is a cyano group or a nitro group), a C ₂ -C ₆ alkynyl group, a C ₃ which may be substituted. -C ₆ cycloalkyl group (said substituent is a substituent selected from substituent group C.), C ₄ ~C ₁₀ bicycloalkyl group, a cyano group, a formyl group, C ₂ -C ₇ alkylcarbonyl group , A benzoyl group which may be substituted (the substituent is a substituent selected from the following substituent group A), a carboxyl group, a C _{2 to} C ₇ alkoxycarbonyl group, a carbamoyl group, di (C _{1 to} C _6). Alkyl) carbamoyl group, optionally substituted phenyl A group (the substituent is a substituent selected from the following substituent group A), an optionally substituted 3- to 6-membered heterocyclic group (the heterocyclic ring includes one nitrogen atom, (It contains an oxygen atom or a sulfur atom, may further contain 1 to 2 nitrogen atoms, and may be condensed with a benzene ring. The substituent is a substituent selected from the following substituent group E.) , amino group which may be substituted (the substituent is a substituent selected from substituent group D.), a nitro group, a hydroxyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, (C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkoxy group, optionally substituted phenoxy group (the substituent is selected from the group consisting of _one hydroxyl group or a halogen atom and C ₁ -C ₆ alkoxy group Pyridazinyl substituted by 1 to 3 identical or different substituents A 5- to 6-membered heterocyclic oxy group which may be substituted (the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and further 1 to 2 The substituent is a substituent selected from the following substituent group E.), a phenylsulfonyloxy group which may be substituted (the substituent is selected from the following substituent group A) A C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group or a tri (C ₁ -C ₆ alkyl) silicon group, or Each of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a 3- to 6-membered cyclic hydrocarbon group which may be substituted together with the carbon atom to which each of the adjacent two is bonded (the cyclic carbon Hydrogen is the same or selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. It may be interrupted by a different one or two hetero atoms. The substituents are halogen atom, C ₁ -C ₆ alkyl group, a hydroxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, a oxo group, hydroxyimino group or a C ₁ -C ₆ alkoxyimino group If the C ₁ -C ₆ alkyl group is substituted, may form a new 3-membered ring with other C ₁ -C ₆ alkyl group or a carbon atom on the ring. )
m and n each independently represent 0 or 1,
Substituent Group A consists of halogen atoms, C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₃ -C ₆ cycloalkyl group, a cyano group and a tri (C ₁ -C ₆ alkyl) silyl group A group,
Substituent group B, a halogen atom, C ₃ -C ₆ cycloalkyl group, a cyano group, C ₂ -C ₇ alkylcarbonyl group, C ₂ -C ₇ alkoxycarbonyl group, a phenyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, consisting of C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₄ alkylenedioxy group, hydroxyimino group and C ₁ -C ₆ alkoxyimino group A group,
Substituent group C includes a halogen atom, an optionally substituted C ₁ -C ₆ alkyl group (the substituent is a substituent selected from the above substituent group B), a C ₃ -C ₆ cycloalkyl group, C ₂ -C ₆ alkenyl group, cyano group, C ₂ -C ₇ alkylcarbonyl group, benzoyl group, carboxyl group, C ₂ -C ₇ alkoxycarbonyl group, carbamoyl group, di (C ₁ -C ₆ alkyl) carbamoyl group, A phenyl group which may be substituted (the substituent is a substituent selected from the above substituent group A), a 5- or 6-membered heterocyclic group (the heterocyclic ring has one nitrogen atom in the ring; , An oxygen atom or a sulfur atom, and further may contain 1 to 2 nitrogen atoms.), An amino group which may be substituted (the substituent is a substituent selected from the following substituent group D) .), a nitro group, a hydroxyl group, C ₁ -C ₆ alkoxy Group, a C ₁ -C ₆ haloalkoxy group, a phenoxy group, C ₁ -C ₆ alkylthio group, a phenylthio group, C ₁ -C ₆ alkylsulfinyl group consisting Le group and C ₁ -C ₆ alkylsulfonyl group,
Substituent group D is, C ₁ -C ₆ alkyl group, C ₂ -C ₇ alkylcarbonyl group, C ₂ -C ₇ alkoxycarbonyl group, a di (C ₁ -C ₆ alkyl) carbamoyl group and C ₁ -C ₆ alkyl A group consisting of a sulfonyl group,
Substituent group E includes a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a hydroxyl group, an optionally substituted phenylsulfonyl group (the substituent is a substituent selected from substituent group A above) And di (C ₁ -C ₆ alkyl) sulfamoyl groups. ]
And one or more 3-phenoxy-4-pyridazinol derivatives selected from the group consisting of a compound represented by the formula: salts thereof and ester derivatives thereof; and 3- (2-chloro-4-mesylbenzoyl) -2- Contains phenylthiobicyclo [3.2.1] oct-2-en-4-one and / or N, N-diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide as an active ingredient Herbicidal composition. In the general formula (I), R ¹ is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a C ₁ -C ₃ alkyl group, a C ₁ -C ₃ haloalkyl group (the halogen atom is represented by 1 to 3 fluorine atoms) an atom.), a cyclopropyl group, C ₂ -C ₃ alkenyl group, a cyano group, C ₂ -C ₄ alkylcarbonyl group, a di (C ₁ -C ₃ alkyl) carbamoyl group, which may be substituted phenyl group {said identical substituents are fluorine atom, chlorine atom, bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group (said halogen atom is selected from fluorine atom, the group consisting of chlorine and bromine Or ₁ to 2 different substituents selected from the group consisting of a cyclopropyl group, a cyano group, and a tri (C ₁ -C ₃ alkyl) silicon group. It is. }, A furyl group, a thienyl group, C ₁ -C ₃ alkoxy group, which may be substituted phenoxy group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ A haloalkyl group (the halogen atom is 1 to 3 fluorine atoms), a cyclopropyl group, a cyano group, and a tri (C ₁ -C ₃ alkyl) silicon group selected from the same or different 1 Two substituents. } Or substituted pyrazolyloxy group (the substituent is two one benzoyl group and two C ₁ -C ₃ alkyl group substituted by a chlorine atom.) Is, according to claim 1 Herbicidal composition. The herbicidal composition according to claim 1, wherein in the general formula (I), R ¹ is a chlorine atom, a bromine atom, a trifluoromethyl group or a cyano group. The herbicidal composition according to claim ¹ , wherein R ¹ in formula (I) is a chlorine atom or a bromine atom. The herbicidal composition according to claim ¹ , wherein R ¹ in formula (I) is a chlorine atom. In the general formula (I), R ² is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C ₁ -C ₃ alkyl group, a (C ₁ -C ₃ alkoxy) C ₁ -C ₃ alkyl group, which may be substituted benzoyl group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group (said halogen atom is a fluorine atom, a chlorine atom and a bromine atom The same or different 1 to 3 halogen atoms selected from the group consisting of :), the same or different selected from the group consisting of cyclopropyl group, cyano group and tri (C ₁ -C ₃ alkyl) silicon group. 1 to 2 substituents. }, C ₂ -C ₄ alkoxycarbonyl group, may be substituted phenoxy group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group (said halogen The atoms are the same or different 1 to 3 halogen atoms selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom.), Cyclopropyl group, cyano group and tri (C ₁ -C ₃ alkyl) It is the same or different 1-2 substituents selected from the group consisting of silicon groups. }, Which may be substituted phenylthio group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group (said halogen atom is a fluorine atom, a chlorine atom and The same or different one to three halogen atoms selected from the group consisting of bromine atoms), the same selected from the group consisting of cyclopropyl groups, cyano groups and tri (C ₁ -C ₃ alkyl) silicon groups. Or it is 1 to 2 different substituents. } Or tri (C ₁ -C ₃ alkyl) silyl group, herbicidal composition according to any one of claims 1 to 5. 6. The general formula (I), wherein R ² is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethoxycarbonyl group, or a trimethylsilyl group. Herbicidal composition. In general formula (I), R ² is a hydrogen atom, herbicidal composition according to any one of claims 1 to 5. In the general formula (I), R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or an optionally substituted C _1- C ₄ alkyl group (the substituent is the same or different 1 to 3 substituents selected from the group consisting of fluorine atom, chlorine atom and bromine atom, or C _{3 to} C ₄ cycloalkyl group, C ₁ to A C ₃ alkylthio group or a C ₁ -C ₃ alkoxyimino group.), A C ₂ -C ₃ alkenyl group, a C ₂ -C ₃ alkynyl group, an optionally substituted C ₃ -C ₅ cycloalkyl group (the substituent) It is fluorine atom, chlorine atom, bromine atom, C ₁ -C ₃ alkyl group, C ₃ -C ₄ cycloalkyl group, a cyano group, a C ₁ -C ₃ alkoxy groups and C ₁ -C ₃ alkylthio group 1 to 3 identical or different substituents selected .), C ₆ ~C ₇ bicycloalkyl group, a cyano group, C ₂ -C ₄ alkylcarbonyl group, C ₂ -C ₄ alkoxycarbonyl group, which may be substituted phenyl group {said substituent is a fluorine atom, a chlorine atom , A bromine atom, a C ₁ -C ₃ alkyl group or a C ₁ -C ₃ haloalkyl group (the halogen atom is the same or different 1 to 3 halogens selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom) Is an atom.) }, A 5- to 6-membered heterocyclic group which may be substituted {the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and further contains 1 to 2 nitrogen atoms. You can. The substituents are fluorine atom, chlorine atom, bromine atom, C ₁ -C ₃ alkyl and C ₁ -C ₃ haloalkyl group (said halogen atom is a fluorine atom, selected from the group consisting of chlorine and bromine 1 to 3 halogen atoms which are the same or different. }, Nitro group, C ₁ -C ₃ alkoxy groups, C ₁ -C ₃ haloalkoxy group (said halogen atom is a fluorine atom, 1-3 was selected same or different from the group consisting of chlorine and bromine of a halogen atom.), which may be substituted phenoxy group (the substituent is a fluorine atom, a chlorine atom, the same or different 1 to 2 atoms selected from the group consisting of bromine and C ₁ -C ₃ alkoxy groups Or a C ₁ -C ₃ alkylthio group, or two of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ that are adjacent to each other. Together, -CH ₂ CH _2- ,
-CH ₂ CH ₂ CH _2- , -CH (CH ₃ ) CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ CH _2- , -CH = CH-CH = CH-, -OCH ₂ CH _2- ,
-OCH = CH -, - OCH = C (CH 3) -, - SCH = CH -, - N = CH-CH = CH -, - OCH 2 O -, - OCH 2 CH 2 O-,

The herbicidal composition according to any one of claims 1 to 8, which forms a group represented by: In the general formula (I), R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or an optionally substituted C _1- C ₄ alkyl group (the substituent is 1 to 3 fluorine atoms or 1 cyclopropyl group), C _{2 to} C ₃ alkenyl group, C _{3 to} C ₄ cycloalkyl which may be substituted group (said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₂ alkyl group, the same one or two substituents selected from the group consisting of cyclopropyl group, and C ₁ -C ₂ alkoxy group in a.), a cyano group, C ₂ -C ₃ alkoxycarbonyl group, a nitro group, a C ₁ -C ₃ alkoxy group or a trifluoromethoxy group, or, R ^3, R ^4, R ^5, R ⁶ and R Two of the ⁷ adjacent to each other are joined together to form —CH ₂ CH ₂ CH ₂ —, —CH (CH ₃ ) CH ₂ C H _2- , -OCH ₂ CH _2- , -OCH = CH- or

The herbicidal composition according to any one of claims 1 to 8, wherein R ³ is not a hydrogen atom. In the general formula (I), R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C ₁ -C ₃ alkyl group. , C ₂ -C ₃ alkenyl group, may be substituted C ₃ -C ₄ cycloalkyl group (said substituents may be the same of one to two selected from the group consisting of a chlorine atom and C ₁ -C ₂ alkyl group A cyano group or a C ₁ -C ₂ alkoxy group, or two of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are combined together to form — CH ₂ CH ₂ CH ₂ - or forms a group represented by -OCH = CH-, provided that, R ³ is not a hydrogen atom, herbicidal composition according to any one of claims 1 to 8. In the general formula (I), R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, allyl group A group, an isopropyl group, an optionally substituted cyclopropyl group (the substituent is two chlorine atoms) or a methoxy group, or R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ . Among them, two adjacent groups together form a group represented by —CH ₂ CH ₂ CH ₂ — or —OCH═CH—, wherein R ³ is not a hydrogen atom. The herbicidal composition as described in any one of these.   The herbicidal composition according to any one of claims 1 to 12, wherein in the general formula (I), m and n are both 0. R ¹ is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a C ₁ -C ₃ alkyl group, a C ₁ -C ₃ haloalkyl group (the halogen atom is 1 to 3 fluorine atoms), cyclo Propyl group, C ₂ -C ₃ alkenyl group, cyano group, C ₂ -C ₄ alkylcarbonyl group, di (C ₁ -C ₃ alkyl) carbamoyl group, optionally substituted phenyl group {the substituent is a fluorine atom, Chlorine atom, bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group (the halogen atom is the same or different 1 to 3 selected from the group consisting of fluorine atom, chlorine atom and bromine atom) ₁ or 2 substituents selected from the group consisting of a cyclopropyl group, a cyano group, and a tri (C ₁ -C ₃ alkyl) silicon group. }, A furyl group, a thienyl group, C ₁ -C ₃ alkoxy group, which may be substituted phenoxy group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ A haloalkyl group (the halogen atom is 1 to 3 fluorine atoms), a cyclopropyl group, a cyano group, and a tri (C ₁ -C ₃ alkyl) silicon group selected from the same or different 1 Two substituents. } Or a substituted pyrazolyloxy group (the substituent is one benzoyl group and two C ₁ -C ₃ alkyl groups substituted by two chlorine atoms),
R ² is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C ₁ -C ₃ alkyl group, a (C ₁ -C ₃ alkoxy) C ₁ -C ₃ alkyl group, an optionally substituted benzoyl group { The substituent is a fluorine atom, a chlorine atom, a bromine atom, a C ₁ -C ₃ alkyl group, a C ₁ -C ₃ haloalkyl group (the halogen atom is selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom) 1 to 3 halogen atoms which are the same or different.), ₁ to 2 substituents which are the same or different and are selected from the group consisting of a cyclopropyl group, a cyano group and a tri (C ₁ -C ₃ alkyl) silicon group. It is a group. }, C ₂ -C ₄ alkoxycarbonyl group, may be substituted phenoxy group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group (said halogen The atoms are the same or different 1 to 3 halogen atoms selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom.), Cyclopropyl group, cyano group and tri (C ₁ -C ₃ alkyl) It is the same or different 1-2 substituents selected from the group consisting of silicon groups. }, Which may be substituted phenylthio group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group (said halogen atom is a fluorine atom, a chlorine atom and The same or different one to three halogen atoms selected from the group consisting of bromine atoms), the same selected from the group consisting of cyclopropyl groups, cyano groups and tri (C ₁ -C ₃ alkyl) silicon groups. Or it is 1 to 2 different substituents. } Or a tri (C ₁ -C ₃ alkyl) silicon group,
R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are independently of each other a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an optionally substituted C ₁ -C ₄ alkyl group The group is the same or different 1 to 3 substituents selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom, or a C _{3 to} C ₄ cycloalkyl group, a C _{1 to} C ₃ alkylthio group or C _1. -C is a ₃ alkoxyimino group.), C ₂ -C ₃ alkenyl group, C ₂ -C ₃ alkynyl group may be substituted C ₃ -C ₅ cycloalkyl group (said substituent is a fluorine atom, a chlorine atom , bromine atom, C ₁ -C ₃ alkyl group, C ₃ -C ₄ cycloalkyl group, the same or different 1 selected from the group consisting of cyano group, C ₁ -C ₃ alkoxy groups and C ₁ -C ₃ alkylthio group a to 3 substituents.), C ₆ ~C ₇ Bishiku Roarukiru group, cyano group, C ₂ -C ₄ alkylcarbonyl group, C ₂ -C ₄ alkoxycarbonyl group, which may be substituted phenyl group {said substituent is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group or a C ₁ -C ₃ haloalkyl group (said halogen atom is a fluorine atom, a chlorine atom and one to three halogen atoms selected same or different from the group consisting of bromine atoms.) it is. }, A 5- to 6-membered heterocyclic group which may be substituted {the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom in the ring, and further contains 1 to 2 nitrogen atoms. You can. The substituents are fluorine atom, chlorine atom, bromine atom, C ₁ -C ₃ alkyl and C ₁ -C ₃ haloalkyl group (said halogen atom is a fluorine atom, selected from the group consisting of chlorine and bromine 1 to 3 halogen atoms which are the same or different. }, Nitro group, C ₁ -C ₃ alkoxy groups, C ₁ -C ₃ haloalkoxy group (said halogen atom is a fluorine atom, 1-3 was selected same or different from the group consisting of chlorine and bromine of a halogen atom.), which may be substituted phenoxy group (the substituent is a fluorine atom, a chlorine atom, the same or different 1 to 2 atoms selected from the group consisting of bromine and C ₁ -C ₃ alkoxy groups Or a C ₁ -C ₃ alkylthio group, or two of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ that are adjacent to each other. Together, —CH ₂ CH ₂ —, —CH ₂ CH ₂ CH ₂ —, —CH (CH ₃ ) CH ₂ CH ₂ —, —CH ₂ CH ₂ CH ₂ CH ₂ —, —CH═CH _{-CH = CH -, - OCH 2} CH 2 -, - OCH = CH -, - OC _{= C (CH 3) -,} - SCH = CH -, - N = CH-CH = CH -, - OCH 2 O -, - OCH 2 CH 2 O-,

A group represented by
The herbicidal composition according to claim 1, wherein m and n are both 0 compounds. R ¹ is a chlorine atom, a bromine atom, a trifluoromethyl group or a cyano group,
R ² is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethoxycarbonyl group or a trimethylsilyl group,
R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are independently of each other a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an optionally substituted C ₁ -C ₄ alkyl group Group is 1 to 3 fluorine atoms, or 1 cyclopropyl group), a C _{2 to} C ₃ alkenyl group, an optionally substituted C _{3 to} C ₄ cycloalkyl group (the substituent is A fluorine atom, a chlorine atom, a bromine atom, a C ₁ -C ₂ alkyl group, a cyclopropyl group, and a C ₁ -C ₂ alkoxy group, the same one or two substituents, and a cyano group. , A C ₂ -C ₃ alkoxycarbonyl group, a nitro group, a C ₁ -C ₃ alkoxy group or a trifluoromethoxy group, or two of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ that are adjacent to each other. Together, —CH ₂ CH ₂ CH ₂ —, —CH (CH ₃ ) CH ₂ CH ₂ −,
_{-OCH 2 CH 2 -, - OCH} = CH- or

In which R ³ is not a hydrogen atom,
The herbicidal composition according to claim 1, wherein m and n are both 0 compounds. R ¹ is a chlorine atom or a bromine atom,
R ² is a hydrogen atom,
R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, C ₁ -C ₃ alkyl group, C ₂ -C ₃ alkenyl. A C _{3 to} C ₄ cycloalkyl group which may be substituted (the substituent is the same 1 or 2 substituents selected from the group consisting of a chlorine atom and a C _{1 to} C ₂ alkyl group), A cyano group or a C ₁ -C ₂ alkoxy group, or two of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are joined together to form —CH ₂ CH ₂ CH ₂ —. or to form a group represented by -OCH = CH-, provided that, R ³ is not a hydrogen atom,
The herbicidal composition according to claim 1, wherein m and n are both 0 compounds. R ¹ is a chlorine atom,
R ² is a hydrogen atom,
R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are independently of each other hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, allyl group, isopropyl group, substituted A cyclopropyl group (the substituent is two chlorine atoms) or a methoxy group, or two of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are adjacent to each other. Together, they form a group represented by —CH ₂ CH ₂ CH ₂ — or —OCH═CH—, provided that R ³ is not a hydrogen atom,
The herbicidal composition according to claim 1, wherein m and n are both 0 compounds.   The compound represented by the general formula (I) is 6-chloro-3- (2-iodophenoxy) -4-pyridazinol, 6-chloro-3- (2-methylphenoxy) -4-pyridazinol, 6-chloro- 3- (2-Isopropylphenoxy) -4-pyridazinol, 6-chloro-3- (2-cyclopropylphenoxy) -4-pyridazinol, 6-chloro-3- (2,3-dihydro-1H-indene-4- Yloxy) -4-pyridazinol, 3- (1-benzofuran-7-yloxy) -6-chloro-4-pyridazinol, 6-chloro-3- (2,5-dimethylphenoxy) -4-pyridazinol, 6-chloro- 3- (2-methoxy-5-methylphenoxy) -4-pyridazinol, 6-chloro-3- (2-chloro-6-methylphenoxy) -4-pyridazinol, 6-chloro-3- (2-chloro-6 -Cyclopropylphenoxy) -4-pyridazinol, 3- (2-bromo-6-methylphenoxy) -6-chloro-4-pyridazinol, 6-chloro-3- (2-ethyl-6-methylphenoxy) -4- Pirida , 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol, 3- (2-allyl-6-methylphenoxy) -6-chloro-4-pyridazinol, 6-chloro-3 -(2-Cyclopropyl-3,5-dimethylphenoxy) -4-pyridazinol, 6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4- The herbicidal composition according to claim 1, which is pyridazinol or 6-chloro-3- (2,3,5,6-tetramethylphenoxy) -4-pyridazinol.