JP2004262940A5

JP2004262940A5 -

Info

Publication number: JP2004262940A5
Application number: JP2004036026A
Authority: JP
Filing date: 2004-02-13
Publication date: 2007-04-05
Anticipated expiration: 2024-02-13

Claims

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 -C ₇ alkoxycarbonyl group, a carbamoyl group, a di (C ₁ -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 a di (C ₁ -C ₆ alkyl) sulfamoyl group. ]
And one or two or more 3-phenoxy-4-pyridazinol derivatives selected from the group consisting of compounds represented by the following formulas, salts thereof and ester derivatives thereof, and 4- (2-chlorophenyl)- N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide, 3- [1- (3,5-dichlorophenyl) -1-methylethyl] -2,3-dihydro -6-methyl-5-phenyl-4H-1,3-oxazin-4-one, 2,3-dihydro-3,3-dimethyl-5-benzofuranyl ethanesulfonate, (RS) -2- (2, One or more compounds selected from the group consisting of 4-dichloro-m-tolyloxy) propionanilide and 3- (4,6-dimethoxypyrimidin-2-yl) -1- (2-ethoxyphenoxysulfonyl) urea A herbicidal composition containing as an active ingredient.

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. It's okay. 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.) 1 to 2 substituents which are the same or different and are selected from the group consisting of: }, 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. pieces _{_{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 substituted pyrazolyloxy group (the substituent is two one benzoyl group and two C ₁ -C ₃ alkyl group substituted by a chlorine atom.), And
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. It's okay. 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.) 1 to 2 substituents which are the same or different and are selected from the group consisting of: }, 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.