JP2010248273A - Oxime compound or salt thereof, and fungicide - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide new oxime compounds or salts thereof, and a fungicide which contains at least one of the compounds as an effective ingredient, exerts a reliable effect and can be safely used. <P>SOLUTION: There are provided the oxime compounds represented by formula (I) or the salts thereof and a fungicide for agricultural gardening which contains at least a kind selected from the compounds or a group consisting of their salts as the effective ingredient. [Wherein A is a heterocyclic group having an unsubstituted or substituted group; B is a single bond or an alkylene group having an unsubstituted or substituted group; Y is an aromatic ring having an unsubstituted or substituted group; and X is an aromatic ring having an unsubstituted or substituted group, or a non-aromatic ring having an unsubstituted or substituted group]. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to a novel oxime compound or a salt thereof and a fungicide containing as an active ingredient at least one selected from the oxime compound or a salt thereof.

  In the cultivation of agricultural and horticultural crops, many control agents are used against crop diseases, but their use is limited and their use is limited by the emergence of drug-resistant pathogens. In many cases, it is difficult to say that it is a sufficiently satisfactory control agent because it causes phytotoxicity and pollution to the plant body, or is highly toxic to human and livestock and has a great impact on the environment. Therefore, there is a strong demand for the emergence of drugs that can be safely used with few such drawbacks.

  In relation to the present invention, the following Patent Document 1 discloses an oxime derivative having a chemical structure similar to that of the compound of the present invention and an agricultural and horticultural fungicide containing it as an active ingredient.

WO2003 / 016303

  An object of the present invention is to provide a novel oxime compound or a salt thereof, and a fungicide that contains at least one of these compounds as an active ingredient and can be used safely and safely.

  The present inventors diligently studied to solve the above problems. As a result, an oxime compound represented by the formula (I) or a salt thereof was obtained. And it discovered that this oxime compound or its salt was useful as an active ingredient of the bactericide which has an effect and can be used safely. The present invention has been further studied and completed based on these findings.

That is, the present invention includes the following aspects.
[1] An oxime compound represented by the formula (I) or a salt thereof.

In formula (I),
A represents an unsubstituted or substituted heterocyclic group.
B represents a single bond or an alkylene group which is unsubstituted or has a substituent.
Y represents an unsubstituted or substituted aromatic ring group.
X represents an unsubstituted or substituted aromatic ring group, or an unsubstituted or substituted non-aromatic ring group.

[2] A fungicide containing as an active ingredient at least one selected from the oxime compound or a salt thereof according to [1].

The oxime compound or a salt thereof of the present invention is a novel compound useful as an active ingredient of a bactericide that has a certain effect and can be used safely.
The disinfectant of the present invention is an agent that has an excellent control effect, does not cause phytotoxicity to plants, and has little toxicity to human fish and environmental impact.

  Hereinafter, the present invention will be described in detail by dividing it into 1) an oxime compound or a salt thereof, and 2) a fungicide.

1) Oxime compound or salt thereof The oxime compound according to the present invention is a compound represented by the formula (I) (hereinafter sometimes referred to as compound (I)).

  The oxime compound or a salt thereof according to the present invention includes hydrates, various solvates and crystal polymorphs. Furthermore, the oxime compound or a salt thereof according to the present invention includes stereoisomers based on asymmetric carbon atoms, double bonds, and the like, and mixtures thereof.

First, the meanings of “unsubstituted” and “having a substituent” in the present specification will be described.
The term “unsubstituted” means only the group that is the mother nucleus. When there is no description of “having a substituent” and only the name of the group serving as a mother nucleus is used, it means “unsubstituted” unless otherwise specified.
On the other hand, the term “having a substituent” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having the same or different structure from the mother nucleus. Accordingly, the “substituent” is another group bonded to a group serving as a mother nucleus. The number of substituents may be one, or two or more. Two or more substituents may be the same or different.
Terms such as “C1-6” indicate that the number of carbon atoms of the group serving as the mother nucleus is 1-6. This number of carbon atoms does not include the number of carbon atoms present in the substituent.
For example, a C1-6 alkyl group having a substituent is an alkyl group having 1 to 6 carbon atoms as a parent group, and any hydrogen atom in the alkyl group is substituted with a group having a different structure It is what has been.

The “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
Examples of groups that can be “substituents” include halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl Group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group and other alkyl groups, preferably C1-6 alkyl group; cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group And the like, preferably a C3-8 cycloalkyl group; vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl Group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl- Alkenyl groups such as 2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, cinnamyl group, preferably C2- 6 alkenyl groups; cycloalkenyl groups such as 2-cyclopropenyl, 2-cyclopentenyl, 3-cyclohexenyl, 4-cyclooctenyl, preferably C3-8 cycloalkenyl; ethynyl, 1-propynyl, 2 -Propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl Group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1 Alkynyl groups such as dimethyl-2-butynyl group, preferably C2~6 alkynyl group;

  Alkoxy group such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group, preferably C1-6 alkoxy group; vinyloxy group An alkenyloxy group such as an allyloxy group, a propenyloxy group or a butenyloxy group, preferably a C2-6 alkenyloxy group; an alkynyloxy group such as an ethynyloxy group or a propargyloxy group, preferably a C2-6 alkynyloxy group; a phenyl group; Aryl groups such as 1-naphthyl group and 2-naphthyl group, preferably C6-10 aryl group; aryloxy groups such as phenoxy group, 1-naphthoxy group, preferably C6-10 aryloxy group; benzyl group, phenethyl group, etc. An aralkyl group, preferably C7-11 ara Aralkyloxy group such as benzyloxy group and phenethyloxy group, preferably C7-12 aralkyloxy group; Acyl group such as formyl group, acetyl group, propionyl group, benzoyl group and cyclohexylcarbonyl, preferably C1-7 acyl Group; acyloxy group such as formyloxy group, acetyloxy group, propionyloxy group, benzoyloxy group, cyclohexylcarbonyloxy group, preferably C1-7 acyloxy group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i An alkoxycarbonyl group such as a propoxycarbonyl group, an n-butoxycarbonyl group or a t-butoxycarbonyl group, preferably a C1-6 alkoxycarbonyl group; a carboxyl group;

  Hydroxyl group; oxo group; haloalkyl group such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group, preferably Is a C1-6 haloalkyl group; a haloalkenyl group such as a 2-chloro-1-propenyl group or a 2-fluoro-1-butenyl group, preferably a C2-6 haloalkenyl group; a 4,4-dichloro-1-butynyl group, Haloalkynyl groups such as 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group, preferably C2-6 haloalkynyl group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, etc. A haloalkoxy group, preferably a C1-6 haloalkoxy group; a 2-chloropropenyloxy group, a 3-bromobutenyloxy group; A haloalkenyloxy group such as a group, preferably a C2-6 haloalkenyloxy group; a haloaryl group such as a 4-chlorophenyl group, a 4-fluorophenyl group, a 2,4-dichlorophenyl group, preferably a C6-10 haloaryl group; Haloaryloxy groups such as fluorophenyloxy groups and 4-chloro-1-naphthoxy groups, preferably C6-10 haloaryloxy groups; chloroacetyl groups, trifluoroacetyl groups, trichloroacetyl groups, 4-chlorobenzoyl groups, etc. A halogen-substituted acyl group, preferably a halogen-substituted C1-7 acyl group;

  Cyano group; isocyano group; nitro group; isocyanato group; cyanato group; amino group; alkylamino group such as methylamino group, dimethylamino group and diethylamino group, preferably C1-6 alkylamino group; anilino group, naphthylamino group, An arylamino group such as an anthracenylamino group, preferably a C6-10 arylamino group; an aralkylamino group such as a benzylamino group or a phenylethylamino group, preferably a C7-11 aralkylamino group; a methylsulfonylamino group, an ethylsulfonyl Alkylsulfonylamino groups such as amino group, n-propylsulfonylamino group, i-propylsulfonylamino group, n-butylsulfonylamino group, t-butylsulfonylamino group; arylsulfonyl such as phenylsulfonylamino group Amino group; heterocyclic sulfonylamino group such as piperazinylsulfonylamino group; acylamino group such as formylamino group, acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group, benzoylamino group, preferably C1-7 acylamino group; alkoxycarbonylamino group such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group, preferably C1-6 alkoxycarbonylamino group; fluoromethylsulfonylamino Group, chloromethylsulfonylamino group, bromomethylsulfonylamino group, difluoromethylsulfonylamino group, dichloromethylsulfonylamino group, 1,1-difluoroethylsulfo Arylamino group, trifluoromethylsulfonyl group, 1,1,1-trifluoroethyl sulfonylamino group, a halo alkylsulfonylamino groups such as pentafluoroethyl sulfonylamino group;

  Bis (methylsulfonyl) amino group, bis (ethylsulfonyl) amino group, (ethylsulfonyl) (methylsulfonyl) amino group, bis (n-propylsulfonyl) amino group, bis (i-propylsulfonyl) amino group, bis (n -Butylsulfonyl) amino group, bis (alkylsulfonyl) amino group such as bis (t-butylsulfonyl) amino group; bis (fluoromethylsulfonyl) amino group, bis (chloromethylsulfonyl) amino group, bis (bromomethylsulfonyl) Amino group, bis (difluoromethylsulfonyl) amino group, bis (dichloromethylsulfonyl) amino group, bis (1,1-difluoroethylsulfonyl) amino group, bis (trifluoromethylsulfonyl) amino group, bis (1,1, 1-trifluoroethylsulfoni ) Bis (haloalkylsulfonyl) amino group such as amino group, bis (pentafluoroethylsulfonyl) amino group; hydrazino group, N′-phenylhydrazino group, N′-methoxycarbonylhydrazino group, N′-acetylhydrazino group , An unsubstituted or substituted hydrazino group such as N′-methylhydrazino group; an unsubstituted group such as aminocarbonyl group, dimethylaminocarbonyl group, phenylaminocarbonyl group, N-phenyl-N-methylaminocarbonyl group; Or an aminocarbonyl group having a substituent; a hydrazinocarbonyl group having an unsubstituted or substituted group such as a hydrazinocarbonyl group, an N′-methylhydrazinocarbonyl group, and an N′-phenylhydrazinocarbonyl group;

  A C1-6 alkyl group substituted with an imino group such as an iminomethyl group, a (1-imino) ethyl group, a (1-imino) -n-propyl group; a hydroxyiminomethyl group, a (1-hydroxyimino) ethyl group, ( A C1-6 alkyl group substituted by a hydroxyimino group such as 1-hydroxyimino) propyl group, methoxyiminomethyl group, (1-methoxyimino) ethyl group; N-methyliminomethyl group, 1-N-phenyliminoethyl N-substituted or N-substituted iminoalkyl groups such as N-hydroxyiminomethyl group and N-methoxyiminomethyl group; mercapto group; isothiocyanato group; thiocyanato group; methylthio group, ethylthio group, n-propylthio group, i- Propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t- An alkylthio group such as a tilthio group, preferably a C1-6 alkylthio group; an alkenylthio group such as a vinylthio group or an allylthio group, preferably a C2-6 alkenylthio group; an alkynylthio group such as an ethynylthio group or a propargylthio group, preferably C2 -6 alkynylthio groups; arylthio groups such as phenylthio groups, naphthylthio groups, preferably C6-10 arylthio groups; heteroarylthio groups such as thiazolylthio groups, 2-pyridylthio groups, 3-pyridylthio groups; benzylthio groups, phenethylthio groups, etc. An aralkylthio group, preferably a C7-11 aralkylthio group; (methylthio) carbonyl group, (ethylthio) carbonyl group, (n-propylthio) carbonyl group, (i-propylthio) carbonyl group, (n-butylthio) carbonyl (C1-6 alkylthio) carbonyl groups such as sulfonyl group, (i-butylthio) carbonyl group, (s-butylthio) carbonyl group, (t-butylthio) carbonyl group; (methyl) thiocarbonyl group, (ethyl) thiocarbonyl group , (N-propyl) thiocarbonyl group, (i-propyl) thiocarbonyl group, (n-butyl) thiocarbonyl group, (i-butyl) thiocarbonyl group, (s-butyl) thiocarbonyl group, (t-butyl) ) A (C1-6 alkyl) thiocarbonyl group such as a thiocarbonyl group;

  Alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group, preferably C1-6 alkylsulfinyl group; alkenylsulfinyl groups such as allylsulfinyl group, preferably C2-6 alkenylsulfinyl group; propargylsulfinyl group, etc. Alkynylsulfinyl group, preferably C2-6 alkynylsulfinyl group; arylsulfinyl group such as phenylsulfinyl group, preferably C6-10 arylsulfinyl group; thiazolylsulfinyl group, 2-pyridylsulfinyl group, 3-pyridylsulfinyl group, etc. A heteroarylsulfinyl group; an aralkylsulfinyl group such as benzylsulfinyl group or phenethylsulfinyl group, preferably C7-11 aralkyl Rufinyl group; alkylsulfonyl group such as methylsulfonyl group, ethylsulfonyl group and t-butylsulfonyl group, preferably C1-6 alkylsulfonyl group; alkenylsulfonyl group such as allylsulfonyl group, preferably C2-6 alkenylsulfonyl group; propargyl Alkynylsulfonyl group such as sulfonyl group, preferably C2-6 alkynylsulfonyl group; arylsulfonyl group such as phenylsulfonyl group, preferably C6-10 arylsulfonyl group; thiazolylsulfonyl group, 2-pyridylsulfonyl group, 3-pyridyl A heteroarylsulfonyl group such as a sulfonyl group; an aralkylsulfonyl group such as a benzylsulfonyl group or a phenethylsulfonyl group, preferably a C7-11 aralkylsulfonyl group;

  Furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, pyrrol-2-yl group, pyrrol-3-yl group, oxazol-2-yl group, oxazole -4-yl group, oxazol-5-yl group, thiazol-2-yl group, thiazol-4-yl group, thiazol-5-yl group, isoxazol-3-yl group, isoxazol-4-yl group, Isoxazol-5-yl group, isothiazol-3-yl group, isothiazol-4-yl group, isothiazol-5-yl group, imidazol-2-yl group, imidazol-4-yl group, imidazole-5 Yl group, pyrazol-3-yl group, pyrazol-4-yl group, pyrazol-5-yl group, 1,3,4-oxadiazol-2-yl group, 1,3,4-thiadi Unsaturated hetero, such as zol-2-yl group, 1,2,3-triazol-4-yl group, 1,2,4-triazol-3-yl group, 1,2,4-triazol-5-yl group 5-membered ring group; pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, 5-chloro-3-pyridyl group, 3-trifluoromethyl-2-pyridyl group, pyridazine-3- Yl group, pyridazin-4-yl group, pyrazin-2-yl group, pyrimidin-2-yl group, pyrimidin-4-yl group, pyrimidin-5-yl group, 1,3,5-triazin-2-yl group An unsaturated hetero 6-membered cyclic group such as 1,2,4-triazin-3-yl group; tetrahydrofuran-2-yl group, tetrahydrapyran-4-yl group, piperidin-3-yl group, pyrrolidin-2- Yl, morpholino, pi Saturated heterocyclic groups such as lysino group and N-methylpiperazinyl group; heterocyclic oxy groups such as 2-pyridyloxy group and 3-oxazolyloxy group; trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group And tri-C1-6 alkyl-substituted silyl groups;

  In these “substituents”, at least one hydrogen atom therein may be substituted with a group having the same or different structure. Examples thereof include those in which a hydrogen atom in an alkyl group is substituted with an alkoxy group, that is, an alkoxyalkyl group.

Y in the formula (I) represents an unsubstituted or substituted aromatic ring group. An aromatic ring group is a monovalent group formed by removing any one hydrogen atom directly bonded to a ring in an aromatic compound. Even if it is an aromatic hydrocarbon group, an aromatic heterocycle It may be a group.
Examples of the aromatic hydrocarbon group include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group. Examples of the aromatic ring group having a substituent include 4-fluorophenyl group, 4-chlorophenyl group, 2,4-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,6-difluorophenyl group, Examples include 4-trifluoromethylphenyl group, 4-methoxyphenyl group, 3,4-dimethoxyphenyl group, 3,4-methylenedioxyphenyl group, 4-trifluoromethoxyphenyl group, and the like.

  Examples of the 5-membered aromatic heterocyclic group include pyrrolyl groups such as a pyrrol-1-yl group, a pyrrol-2-yl group, and a pyrrol-3-yl group; a furan-2-yl group, a furan-3-yl group, and the like. A thienyl group such as a thiophen-2-yl group and a thiophen-3-yl group; an imidazol-1-yl group, an imidazol-2-yl group, an imidazol-4-yl group, and an imidazol-5-yl group Imidazolyl group; pyrazolyl group such as pyrazol-1-yl group, pyrazol-3-yl group, pyrazol-4-yl group, pyrazol-5-yl group; oxazol-2-yl group, oxazol-4-yl group, oxazole Oxazolyl groups such as -5-yl group; isoxazol-3-yl group, isoxazol-4-yl group, isoxazol-5-yl group and the like Isoxazolyl group; thiazolyl group such as thiazol-2-yl group, thiazol-4-yl group, thiazol-5-yl group; isothiazol-3-yl group, isothiazol-4-yl group, isothiazol-5-yl 1,2,3-triazol-1-yl group, 1,2,3-triazol-4-yl group, 1,2,3-triazol-5-yl group, 1,2,4 -Triazolyl groups such as triazol-1-yl group, 1,2,4-triazol-3-yl group, 1,2,4-triazol-5-yl group; 1,2,4-oxadiazole-3- Oxadiazolyl group such as yl group, 1,2,4-oxadiazol-5-yl group, 1,3,4-oxadiazol-2-yl group; 1,2,4-thiadiazol-3-yl group, 1, , 4-thiadiazol-5-yl group, 1,3,4-thiadiazol-2-yl-thiadiazolyl group such as a group; and the like; tetrazol-1-yl group, tetrazolyl group, such as tetrazol-2-yl group.

Examples of the 6-membered aromatic heterocyclic group include pyridyl groups such as pyridin-2-yl group, pyridin-3-yl group and pyridin-4-yl group; pyrazin-2-yl group and pyrazin-3-yl group A pyrazinyl group; a pyrimidinyl group such as a pyrimidin-2-yl group, a pyrimidin-4-yl group and a pyrimidin-5-yl group; a pyridazinyl group such as a pyridazin-3-yl group and a pyridazin-4-yl group; a triazinyl group; Is mentioned.
Examples of the condensed heteroaryl group include indol-1-yl group, indol-2-yl group, indol-3-yl group, indol-4-yl group, indol-5-yl group, indol-6-yl group, and indole. Benzofuran-2-yl group, benzofuran-3-yl group, benzofuran-4-yl group, benzofuran-5-yl group, benzofuran-6-yl group, benzofuran-7-yl group; -2-yl group, benzothiophen-3-yl group, benzothiophen-4-yl group, benzothiophen-5-yl group, benzothiophen-6-yl group, benzothiophen-7-yl group; -Yl group, benzimidazol-2-yl group, benzimidazol-4-yl group, benzimidazol-5-yl group, Benzoxazol-2-yl group, benzoxazol-4-yl group, benzoxazol-5-yl group, benzothiazol-2-yl group, benzothiazol-4-yl group, benzothiazol-5-yl group; quinoline 2-yl group, quinolin-3-yl group, quinolin-4-yl group, quinolin-5-yl group, quinolin-6-yl group, quinolin-7-yl group, quinolin-8-yl group; Can be mentioned.

X in the formula (I) represents an unsubstituted or substituted aromatic ring group, or an unsubstituted or substituted non-aromatic ring group.
Examples of the unsubstituted or substituted aromatic ring group for X include the same groups as those exemplified for Y.

The non-aromatic ring group includes all rings other than the aromatic ring group, and any one hydrogen atom bonded directly to the ring in the non-aromatic hydrocarbon ring compound or non-aromatic heterocyclic compound is eliminated. Is a monovalent group.
Examples of non-aromatic ring groups include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group; 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group, 4-cyclooctenyl group A cycloalkenyl group such as a group; and a non-aromatic heterocyclic group.
The non-aromatic heterocyclic group may be monocyclic or polycyclic.

  Non-aromatic heterocyclic groups include: aziridin-1-yl group, aziridin-2-yl group, epoxy group; pyrrolidin-1-yl group, pyrrolidin-2-yl group, pyrrolidin-3-yl group, tetrahydrofuran-2 -Yl group, tetrahydrofuran-3-yl group; piperidin-1-yl group, piperidin-2-yl group, piperidin-3-yl group, piperidin-4-yl group, piperazin-1-yl group, piperazin-2- Yl group, morpholin-2-yl group, morpholin-3-yl group, morpholin-4-yl group; 1,3-benzodioxol-4-yl group, 1,3-benzodioxol-5-yl Group, 1,4-benzodioxan-5-yl group, 1,4-benzodioxan-6-yl group, 3,4-dihydro-2H-1,5-benzodioxepin-6-yl group, , 4-Dihydro-2H-1,5-benzodioxepin-7-yl group, 2,3-dihydrobenzofuran-4-yl group, 2,3-dihydrobenzofuran-5-yl group, 2,3-dihydro A benzofuran-6-yl group, a 2,3-dihydrobenzofuran-7-yl group; and the like.

A in Formula (I) represents an unsubstituted or substituted heterocyclic group.
Examples of the unsubstituted or substituted heterocyclic group for A include the same as those exemplified for X and Y. Among these, A is preferably a pyridyl group having a substituent.

B in the formula (I) represents a single bond or an alkylene group which is unsubstituted or has a substituent.
An alkylene group is a divalent group formed by removing any two hydrogen atoms from a hydrocarbon compound. Examples of the alkylene group include a methylene group, ethylene, propylene group, and butylene group. Of these, a methylene group is preferred.

  The oxime compound represented by the formula (I) has (E) and (Z) stereoisomers based on the carbon-nitrogen double bond of the oxime moiety. Both of these two stereoisomers and mixtures thereof are included in the present invention. Usually, the synthesized product is obtained only as the (Z) isomer or as a mixture of the (E) isomer and the (Z) isomer. The two isomers can be isolated by separating and purifying a mixture of the (E) and (Z) isomers by a known method such as silica gel column chromatography.

  In the oxime compound represented by the formula (I) and a salt thereof, the (Z) isomer is generally more effective in controlling plant diseases than the (E) isomer. However, the (Z) body is partly converted to the (E) body by the action of light, etc. in the natural environment, and stabilized as a mixture of the (E) body and the (Z) body at a certain ratio. Both compounds and mixtures thereof are also useful. In addition, since the stable ratio of (E) body and (Z) body changes with each compound, it cannot specify collectively.

  The salt of the oxime compound of the present invention is a salt of the compound represented by the formula (I). The salt is not particularly limited as long as the salt is acceptable in agriculture and horticulture. For example, salts of inorganic acids such as hydrochloride, nitrate, sulfate and phosphate; salts of organic acids such as acetate, lactate, propionate and benzoate.

(Method for producing oxime compound and salt thereof)
The oxime compound represented by the formula (I) can be produced, for example, according to the method described in WO03 / 016303 pamphlet.

  For example, the oxime compound represented by the formula (I) is obtained by reacting the compound represented by the formula (II) with the compound represented by the formula (III) in the presence of a base. be able to.

  In the formulas (I), (II) and (III), A, B, X and Y have the same meaning as described above, and L represents a leaving group such as a halogen atom.

Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium carbonate, and potassium carbonate; triethylamine, 4- (dimethylamino) pyridine, pyridine, 1,8-diazabicyclo [5. 4.0] undec-7-ene, organic bases such as 1,5-diazabicyclo [4.3.0] non-5-ene; and the like. These bases can be used alone or in combination of two or more.
The usage-amount of a base is 0.01-100 mol normally with respect to 1 mol of compounds represented by Formula (II), Preferably it is 0.1-5 mol.

This reaction can be performed in the presence or absence of a solvent.
The solvent to be used is not particularly limited as long as it is an inert solvent for this reaction. For example, hydrocarbon solvents such as pentane, hexane, heptane, benzene, toluene and xylene; halogen solvents such as dichloromethane, chloroform and carbon tetrachloride; nitrile solvents such as acetonitrile and propiononitrile; diethyl ether, dioxane and tetrahydrofuran Ether solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, amide solvents such as N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, water, and mixed solvents thereof It is done.

  The temperature at which this reaction is carried out is usually -70 ° C to + 200 ° C, preferably -20 ° C to + 100 ° C. The reaction time is usually 30 minutes to 24 hours, although it depends on the reaction scale.

  Moreover, the salt of the oxime compound represented by the formula (I) can be produced by, for example, reacting an acid with the oxime compound represented by the formula (I) according to a conventional method.

In any of the above reactions, the product can be purified after completion of the reaction. Examples of the purification means include distillation, recrystallization, column chromatography and the like.
The structure of the target product can be identified and confirmed by ¹ H-NMR spectrum, IR spectrum, mass spectrum, elemental analysis and the like.
Some intermediates produced in the production process of the compound of the present invention exhibit bactericidal activity.

2) Disinfectant The disinfectant of this invention contains at least 1 sort (s) chosen from the oxime compound or its salt represented by Formula (I) as an active ingredient.
The bactericidal agent of the present invention may be composed solely of the compound of the present invention, or may be composed of the compound of the present invention and other components.
The disinfectant of the present invention can be formulated into a form that can be taken by general agricultural chemicals, that is, a wettable powder, a granule, a powder, an emulsion, an aqueous solvent, a suspension, a flowable and the like.
Formulation is not particularly limited by the method or procedure, and can be performed by a known method or procedure. In addition, formulation auxiliary materials such as various carriers, additives, and solvents used in formulation are not particularly limited.

  For solid preparations, vegetable powders such as soybean flour and wheat flour, mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, and organic and inorganic compounds such as sodium benzoate, urea, and mirabilite Such additives and / or carriers can be used.

  In liquid preparations, petroleum fractions such as kerosene, xylene and solvent naphtha, solvents such as cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl i-butyl ketone, mineral oil, vegetable oil and water are used. be able to.

  Furthermore, in the disinfectant of the present invention, a surfactant can be added as necessary in order to take a uniform and stable form in these preparations. Examples of the surfactant include alkyl phenyl ether added with polyoxyethylene, alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, sorbitan higher fatty acid ester added with polyoxyethylene, polyoxyethylene Nonionic surfactants such as tristyrylphenyl ether with addition of ethylene; sulfates of alkylphenyl ethers with addition of polyoxyethylene, alkylbenzene sulfonates, sulfates of higher alcohols, alkylnaphthalene sulfonates, poly Examples thereof include a carboxylate, a lignin sulfonate, a formaldehyde condensate of an alkyl naphthalene sulfonate, and an i-butylene-maleic anhydride copolymer.

  Although the amount of the active ingredient in the preparation is not particularly limited, it is usually preferably 0.5 to 95% by mass, more preferably 2 to 70% by mass with respect to the whole preparation.

When the fungicide of the present invention is a wettable powder, emulsion, or flowable, it can be diluted with water to a predetermined concentration and used as a suspension or emulsion. Moreover, when the fungicide of this invention is a powder agent and a granule, it can be used by the method of spraying to a plant as it is.
When a wettable powder, emulsion, suspension, aqueous solvent, granular wettable powder, etc. are diluted with water and applied, the applied concentration is 1-1000 ppm, preferably 10-250 ppm.
The application amount of the fungicide of the present invention varies depending on weather conditions, formulation form, application time, application method, application place, disease to be controlled, target crop, etc., but is usually 1 to 1,000 g as an active ingredient compound amount per hectare. , Preferably 10 to 100 g.

The fungicide of the present invention is excellent against a wide variety of fungi, for example, bacteria belonging to algae (Oomycetes), Ascomycetes, Deuteromycetes, and Basidiomycetes. Has sterilizing power.
Therefore, the fungicide of the present invention can be used for seed treatment, foliage spraying, soil application, water surface application, etc. performed for controlling various diseases occurring in agricultural and horticultural crops including flower buds, turf, and grass. it can.

The disinfectant of the present invention is, for example,
"Sugar beet" of brown spot disease (Cercospora beticola), black root disease (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris);
"Peanut" of brown spot disease (Mycosphaerella arachidis, black astringency (Mycosphaerella berkeleyi);
`` Cucumber '' powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine split (Fusarium oxysporum), mycoses (Sclerotinia sclerotiorum), gray mold (Botrytis) cinerea), anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassicola), seedling blight (Pythium debaryanam, Rhizoctonia solani Kuhn), spot bacterial disease (Pseudomonas syringae pv. Lecrymans)
"Tomato", gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans);
"Golden", gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), subtilis (Mycovellosiella nattrassii);

"Strawberries" of gray mold (Botrytis cinerea), powdery mildew (Sohaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), plague (Phytophthora cactorum);
"Onion" of gray rot (Botrytis allii), gray mold (Botrytis cinerea), white leaf blight (Botrytis squamosa), downy mildew (Peronospora destructor);
"Cabbage", root-knot disease (Plasmodiophora brassicae), soft rot disease (Erwinia carotovora), downy mildew (Peronospora parasitica);
"Green beans", sclerotia (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea);
For apples, powdery mildew (Podosphaera leucotricha), black spot disease (Venturia inaequalis), monilia disease (Monilinia mali), black spot disease (Mycosphaerella pomi), rot disease (Valsa mali), spotted leaf disease (Alternaria mali), red star Diseases (Gymnosporangium yamadae), ring rot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), soot spot (Zygophiala jamaicensis), soot spot (Gloeodes pomigena)
"Oysters" of powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), cornified leaf fall (Cercospora kaki);

"Peach" of Aspen disease (Monilinia fructicola), Black star disease (Cladosporium carpophilum), Homopsis spoilage disease (Phomopsis sp.);
Mongolia fructicola from "auto";
For grapes, gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), black scab (Elsinoe ampelina), brown spot Disease (Pseudocercospora vitis), black rot (Guignardia bidwellII);
"Pear" of black spot disease (Venturia nashicola), red star disease (Gymnosporangium asiaticum), black spot disease (Alternaria kikuchiana), ring-shaped disease (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali);
"Cha" of ring spot disease (Pestalotia theae), anthracnose (Colletotrichum theae-sinensis);
Citrus, scab (Elsinoe fawcetti), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), sunspot (Diaporthe citri), scab (Xanthomonas campestris pv. Citri);
Wheat, powdery mildew (Erysiphe graminis f.sp.tritici), red mold (Gibberella zeae), red rust (Puccinia recondita), brown snow rot (Pythium iwayamai), red snow rot (Monographella nivalis) , Eyespot disease (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), snow rot microbe nuclei (Typhula incarnata), snow rot Mycosclerotia nucleosis (Myriosclerotinia borealis), blight (Gaeumanomyces graminis);

"Barley", leafy leaf disease (Pyrenophora graminea), cloud shape disease (Rhynchosporium secalis), naked smut (Ustilago tritici, U.nuda);
Of rice, rice blast (Pyricularia oryzae), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), sesame leaf blight (Cochliobolus niyabeanus), seedling blight (Pythium graminicola), white leaf blight ( Xanthomonas oryzae), seedling blight (Burkholderia plantarii), brown streak (Acidovorax avenae), blight blight (Burkholderia glumae);
“Tobacco”, Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum);
Botrytis cinerea of "Tulip";
“Bentgrass”, Sclerotinia borealis, Pythium aphanidermatum;
Powdery mildew (Erysiphe graminis) from “Orchardgrass”;
It can be used for controlling such as.

  In addition, bacteria resistant to metalaxyl such as potato tomato plague (Phytophthora infestans), cucumber downy mildew (Pseudoperonospora cubensis), grape downy mildew (Plasmopara viticola); cucumber downy mildew (Pseudoperonospora cubensis), grape beetle The compounds of the present invention are also effective against bacteria having resistance to strobilurin fungicides (eg, cresoxime methyl, azoxystrobin, etc.) such as diseases (Plasmopara viticola).

  Diseases to which the compounds of the present invention are preferably applied include Plasmopara viticola, Pseudoperonospora cubensis, Phythophthora infestans, Pythium aphanidermatum, etc. ), And various diseases caused by oomycetes such as sugar beet root fungus (Aphanomyces cochlloides).

The fungicide of the present invention can be used by mixing with other fungicides, insecticides, acaricides, synergists and the like.
Typical examples of other fungicides, insecticides, acaricides, and plant growth regulators that can be used in combination with the fungicides of the present invention include the following.

<Fungicide>
Copper agent; basic copper chloride, basic copper sulfate and the like. Sulfur agent; thiuram, dineb, manneb, mancozeb, ziram, propineb, polycarbamate, etc. Polyhaloalkylthio agents; captan, phorpet, dichlorofluanide, etc. Organochlorine agents; chlorothalonil, fusalide, etc. Organophosphorus agents; IBP, EDDP, triclophosmethyl, pyrazophos, fosetyl and the like. Benzimidazole agents; thiophanate methyl, benomyl, carbendazim, thiabendazole and the like. Dicarboximide agents; iprodione, procymidone, vinclozolin, fluorimide, etc. Carboxamide agent; oxycarboxin, mepronil, flutolanil, teclophthalam, trichlamide, pencyclon and the like. Acylalanine agents; metalaxyl, oxadixyl, furaxyl and the like. Strobilurins; azoxystrobin, cresoxime methyl, pyraclostrobin, trifloxystrobin, pyribencarb, famoxadone, fenamidone, etc.

  Anilinopyrimidine agents; and purine, mepanipyrim, pyrimethanil, diprodinil and the like. SBI agents; triadimethone, triadimenol, vitertanol, microbutanyl, hexaconazole, propiconazole, triflumizole, prochloraz, pefazoate, phenalimol, pyrifenox, trifolin, flusilazole, etaconazole, diclobutrazole, fluotrimazole, Flutriaphen, penconazole, diniconazole, imazalyl, tridemorph, fenpropimorph, butiobate, epoxiconazole, metconazole, prothioconazole, spiroxamine, fenhexamide, pyributycarb, etc.

  Antibiotic agents; polyoxins, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate, etc. Anilide agents; boscalid, penthiopyrad, fluopyram, bixafen, etc. Guanidine-based agents: iminoctadine acetate, iminoctadine albecylate, dodine, guazatine and the like. Valine agents: dimethomorph, fulmorph, iprovaricarb, benchavaricarb, mandipropamide, etc.

  Other fungicides; simoxanil, cyazofamide, amisulbrom, propamocarb, fluazinam, propamocarb acetate, ethaboxam, fluopicolide, zoxamide, cyflufenamide, metolaphenone, proquinadide, hydroxyisoxazole, metasulfocarb, anilazine, isoprothiolane, ferimthiazole, propenazole , Acibenzoral S methyl, isothianyl, pyroxylone, phthalide, tricyclazole, carpropamide, phenoxanyl, diclocimet, fluazinam, fludioxonil, pyrrolnitrin, hydroxyisoxazole, fursulfamide, dietofencarb, quintozene, metasulfocarb, anilazine, quinomethionate dinodibutin, dithianone , Oki Clinic acid, lecithin, baking soda, Fenaminosurufu, such as phenazine oxide.

<Insecticide, acaricide>
Organic phosphorus and carbamate insecticides; fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, bamidthione, phentoate, dimethoate, formone, marathon, trichlorphone, thiomethone, phosmet, dichlorvos, acephate, EPBP, methylparathion, oxydimethone methyl, ethion, thione Cyanophos, isoxathione, pyridafenthion, hosalon, methidathion, sulprophos, chlorfenvinphos, tetrachlorbinphos, dimethylvinphos, propaphos, isofenphos, ethylthiomethone, propenophos, pyraclophos, monocrotophos, azinephosmethyl, aldicarb, mesomil, thiodicarb, carbofuran, Carbosulfan, Benfuracarb, Fracio Lube, propoxur, BPMC, MTMC, MIPC, carbaryl, pirimicarb, ethiofencarb, such as fenoxycarb.

  Pyrethroid insecticides; permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatoline, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, proprasrin, phenothrin, protorin, fluvinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, Cycloprotonline, tralomethrin, silafluophene, brofenprox, acrinusline and so on.

  Benzoylurea and other insecticides; diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, methoprene, benzoepin, diafenthiuron, acetamiprid , Imidacloprid, nitenpyram, fipronil, cartap, thiocyclam, bensultap, nicotine sulfate, rotenone, metaaldehyde, emamectin, fulvendiamide, spinosad, machine oil, BT and microbial pathogens such as entomopathogenic viruses.

  Nematicides; fenamifos, phostiazates, etc. Acaricides; chlorbenzilate, phenisobromolate, dicophore, amitraz, BPPS, benzomate, hexothiazox, fenbutazin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentezin, cihexatin, pyridaben, fenpyroximate, tebufenpyrad, Pyrimidifen, phenothiocarb, dienochlor, fluacrylpyrim, etc.

<Plant growth regulator>
Gibberellins (eg gibberellin A3, gibberellin A4, gibberellin A7), IAA, NAA and the like.

The disinfectant of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to underwater contact objects such as ship bottoms and fish nets.
Moreover, it can also be used as antibacterial and antifungal agents for walls, bathtubs, shoes and clothes by mixing the bactericidal agent of the present invention into paints and fibers.

  Next, an Example is shown and this invention is demonstrated more concretely. However, the present invention is not limited to these examples.

  Examples of the oxime compound of the present invention that can be produced by a method in which the compound represented by the formula (II) and the compound represented by the formula (III) are reacted in the presence of a base are shown in Tables 1 to 43. . Tables 1 to 43 only show some of the oxime compounds of the present invention that can be produced by the above-described methods. It is described in the present specification that other compounds not specifically shown in the present specification, that is, those substituted with various groups that do not depart from the spirit and scope of the present invention can be produced and used by the above-described methods. It can be easily understood by those skilled in the art.

Among the compounds shown in Tables 1 to 43, physical constants (melting point or refractive index) of the compounds having the following compound numbers were measured. ¹ H-NMR (CDCl ₃ ) was measured for a viscous oil (Visc. Oil) or amorphous (Amorphous). The measurement results are shown below.

Compound 1: melting point 122-123 ° C
Compound 4: Melting point: 123-124 ° C
Compound 5: Melting point 112-114 ° C
Compound 6: Melting point 141-141 ° C.
Compound 7: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.89 (t, 3H, J = 7.4 Hz), 1.35-1.48 (m, 2H), 1.75-1.86 (m, 2H), 3.30 (t, 2H , J = 8.0 Hz) 3.98 (s, 3H), 5.30 (s, 2H), 6.98 (d, 1H, J = 7.5 Hz), 7.12 (d, 1H, J = 8.2 Hz), 7.34-7.52 (m, 5H), 7.66 (dd, 1H, J = 8.2, 7.5 Hz).

Compound 8: Melting point 148-149 ° C
Compound 9: Amorphous; ¹ H-NMR (CDCl ₃ ) 2.87 (s, 6H), 3.98 (s, 3H), 5.29 (s, 2H), 6.95 (d, 1H, J = 7.5 Hz), 7.14 (d, 1H, J = 8.4 Hz), 7.34-7.52 (m, 5H), 7.65 (dd, 1H, J = 8.4, 7.5 Hz).
Compound 10: Amorphous; ¹ H-NMR (CDCl ₃ ) 0.95 (t, 3H, J = 7.2 Hz), 1.40 (tq, 2H, J = 7.5, 7.2 Hz), 1.66 (tt, 2H, J = 7.2, 6.6 H), 3.99 (s, 3H), 4.18 (t, 2H, J = 6.6 Hz), 5.27 (s, 2H), 6.93 (d, 1H, J = 7.5 Hz), 7.18 (m, 2H), 7.52 ( m, 2H), 7.69 (dd, 1H, J = 7.5, 8.1 Hz), 7.90 (d, 1H, J = 8.1 Hz).
Compound 11: Amorphous; ¹ H-NMR (CDCl ₃ ) 0.96 (t, 3H, J = 7.2 Hz), 1.42 (tq, 2H, J = 7.5, 7.2 Hz), 1.66 (tt, 2H, J = 7.2, 6.6 Hz), 3.99 (s, 3H), 4.19 (t, 2H, J = 6.6 Hz), 5.28 (s, 2H), 6.87 (m, 1H), 6.92 (d, 1H, J = 7.8 Hz), 7.10 ( m, 1H), 7.30 (br-s, 1H), 7.69 (dd, 1H, J = 8.4, 7.8 Hz), 7.92 (d, 1H, J = 8.4 Hz).
Compound 12: melting point 106-107 ° C
Compound 13: Amorphous; ¹ H-NMR (CDCl ₃ ) 0.94 (t, 3H, J = 7.5 Hz), 1.41 (tq, 2H, J = 7.5, 7.2 Hz), 1.66 (tt, 2H, J = 7.2, 6.6 Hz), 3.97 (s, 3H), 4.18 (t, 2H, J = 6.6 Hz), 5.27 (s, 2H), 6.95 (d, 1H, J = 8.4 Hz), 7.16 (m, 2H), 7.33 ( m, 2H), 7.56 (br-s, 1H), 7.71 (dd, 1H, J = 8.4, 7.8 Hz), 7.90 (d, 1H, J = 8.4 Hz).
Compound 14: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 4.07 (s, 3H), 5.43 (s, 2H), 7.35-7.50 (m, 6H), 7.64 (d, 1H, J = 7.8 Hz), 7.86 (dd, 1H, J = 7.8, 7.8 Hz) ;.

Compound 15: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 4.06 (s, 3H), 5.37 (s, 2H), 7.18 (d, 1H, J = 7.7 Hz), 7.27 (d, 1H, J = 8.1 Hz), 7.35-7.51 (m, 5H), 7.66 (dd, 1H, J = 8.1, 7.7 Hz).
Compound 16: Amprphous; ¹ H-NMR (CDCl ₃ ) 3.97 (s, 3H), 4.66 (s, 2H), 4.75 (s, 2H), 5.40 (s, 2H), 7.17 (d, 1H), 7.27- 7.68 (m, 11H), 7.73 (dd, 1H).
Compound 17: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 2.54 (s, 3H), 4.00 (s, 3H), 5.35 (s, 2H), 6.93 (d, 1H, J = 7.7 Hz), 7.10 ( d, 1H, J = 7.9 Hz), 7.35-7.55 (m, 6H).
Compound ^{18:. Visc oil; 1 H} -NMR (CDCl 3) 3.40 (s, 3H), 4.02 (s, 3H), 4.69 (s, 2H), 4.79 (s, 2H), 5.40 (s, 2H), 7.17 (d, 1H), 7.34-7.54 (m, 6H), 7.70 (dd, 1H).
Compound 19: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.93 (t, 3H, J = 7.4 Hz), 1.24-1.39 (m, 2H), 1.50-1.60 (m, 2H), 3.02 (s, 3H ), 3.49 (t, 2H, J = 7.4 Hz), 3.99 (s, 3H), 5.22 (s, 2H), 6.39 (d, 1H, J = 8.4 Hz), 6.45 (d, 1H, J = 7.1 Hz) ), 7.35-7.43 (m, 4H), 7.56 (d, 2H, J = 8.1 Hz).
Compound ^{20: oil; 1 H-NMR} (CDCl 3) 0.97 (t, 3H, J = 7.4 Hz), 1.47 (tq, 2H, J = 7.6, 7.4 Hz), 1.74 (tt, 2H, J = 7.6, 6.7 Hz), 4.00 (s, 3H), 4.25 (t, 2H, J = 6.7 Hz), 5.27 (s, 2H), 6.65 (d, 1H, J = 8.4 Hz), 6.81 (d, 1H, J = 7.3 Hz), 7.35-7.44 (m, 3H), 7.52-7.57 (m, 3H).
Compound 21: Amorphous; ¹ H-NMR (CDCl ₃ ) 2.39 (s, 3H), 3.99 (s, 3H), 4.58 (d, 2H), 5.41 (s, 2H), 5.53 (brs, 1H), 6.21 ( d, 1H), 6.46 (d, 1H), 7.14 (d, 1H), 7.20-7.62 (m, 7H), 7.66 (dd, 1H).

Compound 22: Amorphous; ¹ H-NMR (CDCl ₃ ) 3.94 (s, 3H), 4.75 (d, 2H), 5.41 (s, 2H), 7.18-7.88 (m, 13H).
Compound 23: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.94 (t, 3H, J = 7.4 Hz), 1.45 (qt, 2H, J = 7.4, 7.3 Hz), 1.67 (tt, 2H, J = 7.3 , 7.3 Hz), 3.13 (t, 2H, J = 7.3 Hz), 3.98 (s, 3H), 5.34 (s, 2H), 6.91 (d, 1H, J = 7.5 Hz), 7.08 (d, 1H, J = 8.1 Hz), 7.35-7.55 (m, 6H).
Compound 24: Amorphous; ¹ H-NMR (CDCl ₃ ) 0.87 (t, 3H), 1.25-1.37 (m, 10H), 1.74-1.84 (m, 2H), 2.97-3.02 (m, 2H), 4.01 (s , 3H), 4.40 (d, 2H), 5.38 (s, 2H), 5.55 (t, 1H), 7.18-7.72 (m, 8H).
Compound ^{25:. Visc oil; 1 H} -NMR (CDCl 3) 1.44 (t, 3H, J = 7.1 Hz), 4.07 (s, 3H), 4.48 (t, 2H, J = 7.1 Hz), 5.51 (s, 2H), 7.34-7.52 (m, 6H), 7.84 (dd, 1H, J = 7.8, 7.8 Hz), 8.05 (d, 1H, J = 7.1 Hz).
Compound 26: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.89 (t, 3H, J = 7.0 Hz), 1.31-1.36 (m, 4H), 1.65-1.75 (m, 2H), 2.76 (t, 2H , J = 8.0 Hz), 4.10 (s, 3H), 5.38 (s, 2H), 7.07 (d, 1H, J = 7.7 Hz), 7.08 (d, 1H, J = 7.7 Hz), 7.34-7.47 (m , 3H), 7.51-7.54 (m, 2H), 7.58 (dd, 1H, J = 7.7, 7.7 Hz).
Compound ^{27:. Visc oil; 1 H} -NMR (CDCl 3) 0.90 (t, 3H, J = 7.4 Hz), 1.41 (tq, 2H, J = 7.5, 7.4 Hz), 1.66-1.77 (m, 2H), 3.35 (t, 2H, J = 8.0 Hz), 4.05 (s, 3H), 5.48 (s, 2H), 7.36-7.56 (m, 6H), 7.97 (dd, 1H, J = 7.7, 7.5 Hz), 8.03 (d, 1H, J = 7.5 Hz).
Compound 28: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.91 (t, 3H, J = 7.2 Hz), 1.35-1.57 (m, 3H), 1.81-1.92 (m, 1H), 2.86 (ddd, 1H , J = 13.4, 10.0, 4.8 Hz), 3.08 (ddd, 1H, J = 13.4, 9.8, 6.1 Hz), 4.02 (s, 3H), 5.42 (s, 2H), 7.31-7.52 (m, 6H), 7.92-7.94 (m, 2H).

Compound 29: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 1.29 (t, 3H, J = 7.7 Hz), 2.81 (q, 2H, J = 7.7 Hz), 4.02 (s, 3H), 5.39 (s, 2H), 7.08 (d, 1H, J = 7.9 Hz), 7.10 (d, 1H, J = 7.7 Hz), 7.34-7.44 (m, 3H), 7.53 (dd, 2H, J = 8.4, 1.5 Hz), 7.60 (dd, 1H, J = 7.9, 7.7 Hz).
Compound 30: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.97 (t, 3H, J = 7.4 Hz), 1.53 (tq, 2H, J = 7.4, 7.4 Hz), 2.24 (tdd, 2H, J = 7.4 , 7.0, 1.5 Hz), 4.00 (s, 3H), 5.38 (s, 2H), 6.47 (dt, 1H, J = 15.9, 1.5 Hz), 6.72 (dt, 1H, J = 15.9, 7.0 Hz), 7.06 (d, 1H, J = 7.7 Hz), 7.19 (d, 1H, J = 7.9 Hz), 7.34-7.47 (m, 3H), 7.52 (dd, 2H, J = 8.6, 1.3 Hz), 7.59 (dd, 1H, J = 7.9, 7.7 Hz).
Compound 31: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 1.91 (tt, 2H, J = 7.8, 7.5 Hz), 2.64 (t, 2H, J = 7.8 Hz), 3.01 (s, 3H), 3.54 ( t, 2H, J = 7.5 Hz), 3.96 (s, 3H), 5.21 (s, 2H), 6.34 (d, 1H, J = 8.6 Hz), 6.46 (d, 1H, J = 7.3 Hz), 7.15- 7.20 (m, 3H), 7.25-7.30 (m, 2H), 7.34-7.48 (m, 4H), 7.55 (d, 2H, J = 7.7 Hz).
Compound 32: Melting point 103-106 ° C .; ¹ H-NMR (CDCl ₃ ) 4.01 (s, 3H), 5.43 (s, 2H), 7.09-7.14 (m, 2H), 7.29-7.62 (m, 11H), 7.66 (dd, 1H, J = 7.9, 7.7 Hz).
Compound 33: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.93 (s, 9H), 4.39 (s, 3H), 4.99 (d, 2H), 5.25 (s, 2H), 6.39 (d, 1H), 6.63 ( d, 1H), 7.29-7.52 (m, 10H), 7.98 (d, 1H).
Compound ^{35: Amorphous; 1 H-NMR} (CDCl 3) 1.91 (s, 9H), 2.91 (t, 2H), 3.53 (m, 2H), 4.40 (s, 3H), 5.23 (s, 2H), 6.37 ( d, 1H), 6.61 (d, 1H), 7.20-7.51 (m, 10H), 7.85-7.88 (m, 2H).

Compound 36: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.80 (t, 3H), 1.96 (s, 9H), 3.48 (s, 3H), 4.04 (q, 2H), 4.47 (s, 2H), 6.46 ( d, 1H), 6.66 (d, 2H), 7.44-7.50 (m, 5H), 8.07 (dd, 1H).
Compound 37: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 1.89-2.00 (m, 11H), 2.72 (t, 2H), 3.23-3.29 (m, 2H), 4.41 (s, 3H), 5.22 (s , 2H), 6.33 (d, 1H), 6.59 (d, 1H), 7.17-7.49 (m, 10H), 7.85 (dd, 1H).
Compound 38: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.93 (t, 3H), 1.32-1.54 (m, 4H), 2.17-2.30 (m, 2H), 4.00 (s, 3H), 5.38 (s , 2H), 6.46 (d, 1H), 6.73 (dt, 1H), 7.05 (d, 1H), 7.19 (d, 1H), 7.34-7.65 (m, 6H).
Compound 39: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 4.02 (s, 3H), 5.44 (s, 2H), 7.11-7.69 (m, 13H).

Compound 43: ¹ H-NMR (CDCl ₃ ) 2.71 (s, 3H), 4.06 (s, 3H), 5.45 (s, 2H), 7.35-7.52 (m, 5H), 7.82 (s, 2H).
Compound ^{44:. Visc oil; 1 H} -NMR (CDCl 3) 2.53 (s, 3H), 4.03 (s, 3H), 5.33 (s, 2H), 7.10 (s, 1H), 7.11 (s, 1H), 7.35-7.48 (m, 3H), 7.51 (dd, 2H, J = 7.0, 1.7 Hz).
Compound 47: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 2.30 (s, 3H), 2.49 (s, 3H), 4.02 (s, 3H), 5.34 (s, 2H), 6.88 (s, 1H), 6.91 (s, 1H), 7.34-7.47 (m, 3H), 7.53 (d, 2H, J = 7.0 Hz).
Compound 49: melting point 124-125 ° C
Compound 50: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 3.78 (m, 3H), 4.01 (s, 3H), 5.42 (s, 2H), 6.92 (d, 2H), 7.02 (d, 1H), 7.08 (d, 1H), 7.28-7.67 (m, 11H).

Compound ^{51:. Visc oil; 1 H} -NMR (CDCl 3) 1.35 (t, 3H), 2.31 (d, 3H), 3.99 (s, 3H), 4.28 (q, 2H), 5.43 (s, 2H), 7.16 (d, 1H), 7.29-7.61 (m, 7H), 7.71 (dd, 1H).
Compound 52: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 2.46 (s, 3H), 2.48 (s, 3H), 4.02 (s, 3H), 5.33 (s, 2H), 6.84 (s, 1H), 6.89 (s, 1H), 7.35-7.47 (m, 3H), 7.51-7.54 (m, 2H).
Compound 53: mp ^{116~117 ℃; 1 H-NMR (} CDCl 3) 2.67 (s, 3H), 3.10 (s, 3H), 4.06 (s, 3H), 5.44 (s, 2H), 7.35-7.51 (m , 5H), 7.56 (s, 1H), 7.60 (s, 1H).
Compound 54: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.84 (s, 9H), 3.68 (s, 2H), 3.82 (s, 3H), 5.25 (s, 2H), 6.92 (d, 2H, J = 8.4 Hz), 7.18 (d, 1H, J = 7.5 Hz), 7.24-7.42 (m, 5H), 7.49 (d, 2H, J = 8.4 Hz), 7.67 (dd, 1H, J = 8.4, 7.5 Hz), 7.78 (br-s, 1H), 8.09 (d, 1H, J = 8.4 Hz).
Compound 55: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.75 (s, 9H), 3.68 (s, 2H), 3.82 (s, 3H), 5.29 (s, 2H), 6.92 (d, 2H, J = 8.4 Hz), 7.06 (d, 1H, J = 7.8 Hz), 7.25 (d, 2H, J = 8.4 Hz), 7.43-7.45 (m, 3H), 7.56-7.59 (m, 2H), 7.66 (dd, 1H , J = 8.4, 7.8 Hz), 7.76 (br-s, 1H), 8.10 (d, 1H, J = 8.4 Hz).
Compound 56: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.77 (s, 9H), 2.13 (s, 3H), 3.68 (s, 2H), 3.81 (s, 3H), 5.30 (s, 2H), 6.91 ( d, 2H, J = 8.7 Hz), 7.18-7.32 (m, 7H), 7.69 (dd, 1H, J = 8.4, 7.5 Hz), 7.76 (br-s, 1H), 8.10 (d, 1H, J = (8.4 Hz).
Compound 57: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.76 (s, 9H), 2.18 (s, 3H), 3.67 (s, 2H), 3.82 (s, 3H), 5.26 (s, 2H), 6.89- 6.99 (m, 3H), 7.19-7.37 (m, 6H), 7.62 (dd, 1H, J = 8.1, 7.5 Hz), 7.76 (br-s, 1H), 8.08 (d, 1H, J = 8.1 Hz) .

Compound 61: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.93 (t, 3H), 1.36-1.48 (m, 2H), 1.63-1.72 (m, 2H), 4.06 (s, 3H), 4.19 (t , 2H), 5.28 (s, 2H), 7.02 (d, 1H), 7.05 (dd, 1H), 7.20-7.28 (m, 2H), 7.41-7.48 (m, 1H), 7.66 (m, 2H), 7.92 (d, 1H).
Compound 62: Amorphous; ¹ H-NMR (CDCl ₃ ) 2.13 & 2.18 (s, 3H), 3.46 & 3.48 (s, 3H), 3.67 (s, 2H), 3.81 & 3.82 (s, 3H), 5.27 & 5.31 (s, 2H), 5.83 & 5.90 (s, 2H), 6.90-6.99 (m, 2H + 0.5H), 7.20-7.39 (m, 6H + 0.5H), 7.61-7.72 (m, 1H), 7.75 & 7.77 (br-s, 1H), 8.08-8.13 (m, 1H) .The integral ratio of 0.5H indicates that 1H of an isomer.
Compound 64: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.96 (t, 3H), 1.28-1.46 (m, 2H), 4.11 (s, 3H), 4.19 (q, 2H), 5.31 (s, 2H ), 6.92-7.06 (m, 3H), 7.28 (brs, 1H), 7.35-7.46 (m, 1H), 7.70 (dd, 1H), 7.92 (d, 1H).

Compound ^{66:. Visc oil; 1 H} -NMR (CDCl 3) 4.05 (s, 3H), 5.59 (s, 2H), 7.33-7.46 (m, 4H), 7.50-7.58 (m, 3H), 7.73 (ddd , 1H, J = 7.8, 7.8, 1.5 Hz), 7.83 (d, 1H, J = 8.2 Hz), 8.05 (d, 1H, J = 8.4 Hz), 8.17 (d, 1H, J = 8.6 Hz).
Compound 67: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 4.05 (s, 3H), 5.61 (s, 2H), 7.36-7.61 (m, 5H), 7.63-7.68 (m, 2H), 7.76 (ddd , 1H, J = 7.9, 7.7, 1.5 Hz), 7.84 (d, 1H, J = 8.2 Hz), 8.08 (d, 1H, J = 9.2 Hz), 8.20 (d, 1H, J = 8.6 Hz).
Compound 69: Amorphous; ¹ H-NMR (CDCl ₃ ) 4.02 (s, 3H), 5.65 (s, 2H), 7.37-7.58 (m, 7H), 7.90 (d, 1H, J = 7.7 Hz), 8.04 ( d, 1H, J = 7.7 Hz).
Compound 75: Amorphous; ¹ H-NMR (CDCl ₃ ) 3.86 (s, 3H), 5.47 (s, 2H), 7.35-7.53 (m, 6H), 7.69 (dd, 1H, J = 8.6, 1.8 Hz), 7.77 (s, 1H), 8.11 (d, 1H, J = 8.6 Hz), 8.16 (d, 1H, J = 8.4 Hz), 8.94 (dd, 1H, J = 4.2, 1.8 Hz).
Compound 78: Melting point 126-127 ° C

Compound 79: mp 168-170 ° C
Compound 87: Melting point 157-160 ° C
Compound 88: Melting point 151-153 ° C
Compound 90: Amorphous; ¹ H-NMR (CDCl ₃ ) 0.94 (d, 6H), 1.24 (d, 3H), 1.84 (dt, 1H), 3.98 (s, 3H), 4.75 (dt, 1H), 5.25 ( s, 2H), 6.95 (d, 1H), 7.23-7.52 (m, 5H), 7.67 (dd, 1H), 7.90 (d, 1H).
Compound 91: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 4.18 (s, 3H), 5.68 (s, 2H), 7.43 (td, 1H, J = 7.7, 1.1 Hz), 7.49-7.55 (m, 4H ), 7.62-7.65 (m, 2H), 7.91 (d, 1H, J = 7.7 Hz), 8.05 (d, 1H, J = 8.1 Hz).

Compound 100: mp 49-52 ° C.
Compound 101: mp 129-131 ° C
Compound 102: mp 96-98 ° C
Compound 103: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 3.96 (s, 3H), 5.56 (s, 2H), 7.34-7.61 (m, 6H), 7.81 (d, 1H).
Compound 104: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.72 (t, 3H), 1.28 (tq, 2H), 1.61 (s, 6H), 4.02 (s, 3H), 4.40 (t, 1H), 5.38 (s, 2H), 7.25-7.51 (m, 7H), 7.82 (t, 1H).
Compound 105: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.93 (t, 3H), 1.32-1.45 (m, 2H), 1.50 (s, 6H), 1.71-1.80 (m, 2H), 3.97 (s , 3H), 5.25 (s, 2H), 6.92 (d, 1H), 7.19 (br-s, 1H), 7.34-7.53 (m, 5H), 7.65 (t, 1H), 7.86 (d, 1H).
Compound 106: mp 126-127 ° C.

Compound 107: mp 69-71 ° C.
Compound 108: Melting point 90-93 ° C
Compound 109: Refractive index nD (22.4 ° C.) 1.6260
Compound 110: mp 48-52 ° C.
Compound 111: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 2.61-2.64 (m, 4H), 3.17 (s, 2H), 3.76 (m, 4H), 4.00 (s, 3H), 5.31 (s, 2H ), 7.02 (d, 1H), 7.35-7.53 (m, 5H), 7.70 (t, 1H), 8.16 (d, 1H), 9.44 (br-s, 1H).
Compound 112: mp 63-65 ° C.
Compound 113: mp 64-65 ° C.

Compound 114: mp 97-99 ° C.
Compound 115: mp 109-112 ° C
Compound 116: mp 134-136 ° C
Compound 117: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.92 (t, 3H, J = 7.1 Hz), 1.33-1.40 (m, 4H), 1.64-1.74 (m, 2H), 3.99 (s, 3H ), 4.18 (t, 2H, J = 6.8 Hz), 5.27 (s, 2H), 6.94 (d, 1H, J = 7.7 Hz), 7.28-7.44 (m, 4H), 7.60 (dd, 1H, J = 2.0, 1.6 Hz), 7.68 (dd, 1H, J = 8.2, 7.7 Hz), 7.91 (d, 1H, J = 8.2 Hz).
Compound 118: Amorphous; ¹ H-NMR (CDCl ₃ ) 0.89-0.94 (m, 3H), 1.33-1.39 (m, 4H), 1.64-1.73 (m, 2H), 4.00 (s, 3H), 4.18 (t , 2H, J = 6.7 Hz), 5.23 (s, 2H), 6.93 (d, 1H, J = 7.4 Hz), 7.29 (br-s, 1H), 7.33-7.39 (m, 2H), 7.49 (dd, 1H, J = 5.1, 1.6 Hz), 7.67 (dd, 1H, J = 8.4, 7.4 Hz), 7.89 (d, 1H, J = 8.4 Hz).
Compound 119: Amorphous; ¹ H-NMR (CDCl ₃ ) 0.89-0.94 (m, 3H), 1.34-1.39 (m, 4H), 1.64-1.71 (m, 2H), 2.52 (s, 3H), 4.18 (t , 2H, J = 6.7 Hz), 5.20 (s, 2H), 6.91 (d, 1H, J = 7.5 Hz), 7.17-7.19 (m, 1H), 7.39-7.40 (m, 2H), 7.68 (dd, 1H, J = 8.4, 7.5 Hz), 7.90 (d, 1H, J = 8.4 Hz).
Compound 120: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.93 (t, 3H), 1.28 (d, 3H), 1.36-1.66 (m, 4H), 3.98 (s, 3H), 4.92 (q, 1H ), 5.25 (s, 2H), 6.94 (d, 1H), 7.23 (br-s, 1H), 7.34-7.53 (m, 5H), 7.67 (t, 1H), 7.89 (d, 1H).

Compound 121: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 0.97 (s, 9H), 3.88 (s, 2H), 3.97 (s, 3H), 5.26 (s, 2H), 6.95 (d, 1H), 7.34-7.52 (m, 6H), 7.68 (t, 1H), 7.90 (d, 1H).
Compound 122: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 1.53 (s, 9H), 1.67 (s, 6H), 4.04 (s, 3H), 6.82 (d, 1H), 7.10 (br-s, 1H ), 7.28-7.66 (m, 6H), 7.77 (d, 1H).
Compound 123: mp 134-136 ° C
Compound 124: Amorphous; ¹ H-NMR (CDCl ₃ ) 2.78-2.95 (m, 4H), 3.78-3.82 (m, 4H), 3.99 (s, 3H), 5.21 (s, 2H), 5.42 (s, 1H ), 6.64 (d, 1H), 6.96 (d, 1H), 7.34-7.54 (m, 6H).
Compound 125: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.43 (br, 2H), 1.68 (m, 4H), 2.68 (br, 4H), 3.99 (s, 3H), 5.20 (s, 2H), 5.28 ( s, 1H), 6.60 (d, 1H), 6.93 (d, 1H), 7.35-7.54 (m, 6H).
Compound 126: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.72 (s, 6H), 4.00 (s, 3H), 5.42 (s, 2H), 7.33-7.53 (m, 7H), 7.91 (t, 1H).
Compound 127: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.52 (s, 9H), 3.99 (s, 3H), 5.21 (s, 2H), 6.67 (dd, 1H), 7.28 (brs, 1H), 7.35- 7.67 (m, 6H).

Compound 128: mp 155-156 ° C
Compound 129: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.54 (s, 9H), 3.91 (s, 3H), 5.26 (s, 2H), 6.86 (s, 1H), 7.33-7.45 (m, 3H), 7.49-7.53 (m, 2H), 8.79 (br-s, 1H).
Compound 130: Amorphous; ¹ H-NMR (CDCl ₃ ) 3.81 (s, 3H), 5.25 (s, 2H), 6.79 (d, 1H), 6.97 (d, 1H), 7.09-7.19 (m, 3H), 7.31-7.52 (m, 7H), 7.67 (m, 1H).
Compound 131: mp 124-125 ° C.
Compound 132: mp 98-101 ° C.
Compound 133: Amorphous; ¹ H-NMR (CDCl ₃ ) 2.33 (s, 3H), 3.62 (s, 2H), 4.08 (s, 3H), 5.25 (s, 2H), 7.02 (d, 1H), 7.28- 7.52 (m, 5H), 7.69 (dd, 1H), 8.08 (d, 1H), 9.38 (brs, 1H).
Compound 134: Amorphous; ¹ H-NMR (CDCl ₃ ) 3.52 (s, 2H), 3.81 (s, 3H), 4.07 (s, 3H), 5.29 (s, 2H), 7.04 (d, 1H), 7.34- 7.53 (m, 5H), 7.71 (dd, 1H), 8.10 (d, 1H), 9.48 (brs, 1H).

Compound ^{135: Amorphous; 1 H-NMR} (CDCl 3) 3.89 (s, 3H), 5.32 (d, 1H), 7.35-7.57 (m, 9H), 7.55-7.69 (m, 2H), 8.00 (t, 1H ), 8.12 (d, 1H).
Compound 136: mp 124-126 ° C.
Compound 137: Amorphous; ¹ H-NMR (CDCl ₃ ) 3.98 (s, 3H), 4.60 (s, 2H), 5.30 (s, 2H), 6.95 (d, 2H), 7.06 (d, 1H), 7.28- 7.52 (m, 7H), 7.74 (t, 1H), 8.19 (d, 1H), 8.80 (br-s, 1H).
Compound 138: Amorphous; ¹ H-NMR (CDCl ₃ ) 3.93 (s, 3H), 3.97 (s, 3H), 4.67 (s, 2H), 5.30 (s, 2H), 6.91-7.10 (m, 5H), 7.34-7.51 (m, 5H), 7.72 (t, 1H), 8.21 (d, 1H), 9.64 (br-s, 1H).
Compound 139: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 3.82 (s, 3H), 3.96 (s, 3H), 4.62 (s, 2H), 5.30 (s, 2H), 6.57-6.64 (m, 3H ), 7.06 (d, 1H), 7.21-7.53 (m, 6H), 7.74 (t, 1H), 8.21 (d, 1H), 8.82 (br-s, 1H)
Compound 140: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 3.79 (s, 3H), 3.96 (s, 3H), 4.58 (s, 2H), 5.29 (s, 2H), 6.85-6.97 (m, 4H ), 7.05 (d, 1H), 7.34-7.53 (m, 5H), 7.73 (t, 1H), 8.20 (d, 1H), 8.86 (br-s, 1H).
Compound 141: Amorphous; ¹ H-NMR (CDCl ₃ ) 3.98 (s, 3H), 4.61 (s, 2H), 5.30 (s, 2H), 6.89 (dd, 1H), 7.07 (d, 1H), 7.14 ( d, 1H), 7.28-7.52 (m, 6H), 7.75 (t, 1H), 8.19 (d, 1H), 8.78 (br-s, 1H).

Compound 142: Amorphous; ¹ H-NMR (CDCl ₃ ) 3.90 (s, 3H), 4.08 (s, 2H), 4.10 (s, 3H), 5.29 (s, 2H), 6.96-7.03 (m, 5H), 7.70 (dd, 1H), 8.03 (d, 2H), 8.11 (d, 1H), 9.68 (brs, 1H).
Compound 143: Melting point 181 to 182 ° C.
Compound 144: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 3.98 (s, 3H), 4.69 (s, 2H), 5.31 (s, 2H), 7.07 (d, 1H), 7.25-7.52 (m, 7H ), 7.74 (t, 1H), 8.20 (d, 1H), 8.35 (dd, 1H), 8.46 (d, 1H), 8.81 (br-s, 1H).
Compound 145: Refractive index nD (20.1 degreeC) 1.5743
Compound 146: Amorphous; ¹ H-NMR (CDCl ₃ ) 4.01 (s, 3H), 4.21 (s, 2H), 5.30 (s, 2H), 7.06 (d, 1H), 7.35-7.53 (m, 5H), 7.74 (t, 1H), 8.12 (d, 1H), 8.79 (br-s, 1H).
Compound 147: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 4.03 (s, 3H), 4.72 (s, 2H), 5.31 (s, 2H), 6.94-7.12 (m, 4H), 7.34-7.51 (m , 5H), 7.66 (t, 1H), 7.76 (d, 1H), 8.19 (br-s, 1H).
Compound 148: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.44 (t, 3H, J = 7.3 Hz), 4.01 (s, 3H), 4.44 (q, 2H, J = 7.3 Hz), 5.32 (s, 2H) , 7.11 (d, 1H, J = 7.7 Hz), 7.35-7.52 (m, 5H), 7.78 (dd, 1H, J = 8.2, 7.7 Hz), 8.19 (d, 1H, J = 8.2 Hz), 9.37 ( br-s, 1H).

Compound 149: Amorphous; ¹ H-NMR (CDCl ₃ ) 2.32 (m, 1H), 2.56 (m, 1H), 2.95 (m, 1H), 3.13 (m, 1H), 3.27 (m, 1H), 3.55 ( m, 1H), 3.99 (s, 3H), 4.82 (m, 1H), 4.84 (s, 1H), 5.22 (s, 2H), 6.35 (d, 1H), 6.58 (d, 1H), 7.36-7.50 (m, 6H).
Compound 150: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 3.17 (t, 2H, J = 6.5 Hz), 3.69 (s, 3H), 4.69 (t, 2H, J = 6.5 Hz), 7.04 (d, 1H, J = 7.8 Hz), 7.15 (ddd, 1H, J = 7.6, 4.9, 0.9 Hz), 7.34-7.53 (m, 5H), 7.59 (ddd, 1H, J = 7.8, 7.6, 1.8 Hz), 8.54 (dd, 1H, J = 4.9, 1.8 Hz).
Compound 151: Amorphous; ¹ H-NMR (CDCl ₃ ) 3.97 (s, 3H), 5.00 (s, 2H), 5.29 (s, 2H), 7.05 (d, 1H), 7.34-7.54 (m, 5H), 7.73 (t, 1H), 8.13 (d, 1H), 8.19 (d, 1H), 8.26 (d, 1H), 8.49 (d, 1H), 8.65 (br-s, 1H).
Compound 152: melting point 127-130 ° C
Compound 153: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.80 (s, 6H), 3.97 (s, 3H), 5.26 (s, 2H), 6.93 (d, 1H), 7.28-7.52 (m, 9H), 7.60 (dd, 1H), 7.76 (d, 1H).
Compound 154: mp 85-87 ° C
Compound 155: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.40-1.63 (m, 11H), 2.16-2.21 (m, 2H), 3.67 (s, 3H), 5.25 (s, 2H), 6.93 (d, 1H ), 7.25 (s, 1H), 7.34-7.53 (m, 5H), 7.65 (t, 1H), 7.87 (d, 1H).

Compound 156: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.76 (s, 6H), 3.98 (s, 3H), 4.68 (br, 1H), 5.29 (s, 3H), 6.47 (d, 1H), 6.66 ( d, 1H), 7.34-7.56 (m, 6H).
Compound 157: mp 150-152 ° C.
Compound 159: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.59 (s, 6H), 3.91 (s, 3H), 5.26 (s, 2H), 6.97-7.13 (m, 4H), 7.26-7.51 (m, 7H ), 7.73 (t, 1H), 8.23 (d, 1H), 9.13 (br-s, 1H).
Compound 160: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.48-1.58 (m, 2H), 1.98-2.05 (m, 2H), 3.47-3.55 (m, 2H), 3.73 (m, 1H), 3.95-4.01 (m, 5H), 5.15 (br, 1H), 5.20 (s, 2H), 6.33 (d, 1H), 6.50 (d, 1H), 7.34-7.55 (m, 6H).
Compound 161: mp 134-136 ° C.
Compound 162: mp 108-110 ° C.

Compound 163: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.45 (s, 6H), 3.02 (s, 2H), 3.95 (s, 3H), 5.24 (s, 2H), 6.86 (d, 1H), 7.35- 7.52 (m, 6H), 7.60-7.70 (m, 2H).
Compound 165: mp 154-157 ° C.
Compound 166: mp 98-101 ° C.
Compound 167: mp 74-76 ° C.
Compound 168: Amorphous; ¹ H-NMR (CDCl ₃ ) 2.47 (s, 3H), 4.68 (s, 2H), 5.30 (s, 2H), 6.94 (d, 1H), 7.25-7.61 (m, 6H), 9.18 (br-s, 1H).
Compound 169: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.60 (s, 9H), 3.96 (s, 3H), 4.67 (s, 2H), 5.23 (s, 2H), 7.00 (d, 1H), 7.26- 7.52 (m, 6H).

Compound 170: mp 178-187 ° C
Compound 171: melting point 113-117 ° C.
Compound 172: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.92-2.01 (m, 2H), 2.12-2.23 (m, 1H), 2.32-2.41 (m, 1H), 3,93-4.13 (m, 2H) , 4.00 (s, 3H), 4.48 (dd, 1H, J = 8.4, 6.0 Hz), 5.29 (s, 2H), 7.03 (d, 1H, J = 7.5 Hz), 7.35-7.53 (m, 5H), 7.71 (dd, 1H, J = 8.4, 7.5 Hz), 8.18 (d, 1H, J = 8.4 Hz), 8.98 (br-s, 1H).
Compound 173: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.52 (s, 9H), 2.69 (s, 3H), 5.25 (s, 2H), 7.00 (d, 1H, J = 7.4 Hz), 7.18 (br- s, 1H), 7.31-7.41 (m, 3H), 7.44-7.49 (m, 2H), 7.66 (dd, 1H, J = 8.2, 7.4 Hz), 7.82 (d, 1H, J = 8.2 Hz).
Compound 174: mp 95-98 ° C.
Compound 175: mp 75-77 ° C
Compound 176: Melting point 79-80 ° C

Compound 177: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 1.93 (s, 3H), 2.01 (s, 3H), 3.97 (s, 3H), 4.61 (s, 2H), 5.28 (s, 2H), 7.03 (d, 1H), 7.34-7.52 (m, 5H), 7.71 (t, 1H), 8.19 (d, 1H), 8.49 (br-s, 1H).
Compound 178: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 1.77-1.88 (m, 4H), 2.39-2.59 (m, 4H), 3.97 (s, 3H), 4.62 (s, 2H), 5.28 (s , 2H), 7.04 (d, 1H), 7.35-7.51 (m, 5H), 7.71 (t, 1H), 8.19 (d, 1H), 8.55 (br-s, 1H).
Compound 179: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 2.40 (t, 2H), 2.76 (t, 2H), 3.81-3.89 (m, 4H), 3.97 (s, 3H), 4.63 (s, 2H ), 5.29 (s, 2H), 7.03 (d, 1H), 7.35-7.52 (m, 5H), 7.72 (t, 1H), 8.18 (d, 1H), 8.45 (br-s, 1H).
Compound 180: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 1.50 (d, 3H), 1.91 (s, 3H), 2.00 (s, 3H), 3.97 (s, 3H), 4.61-4.72 (q, 1H ), 5.28 (s, 2H), 7.03 (d, 1H), 7.35-7.52 (m, 5H), 7.71 (t, 1H), 8.20 (d, 1H), 8.57 (br-s, 1H).
Compound 181: melting point 136-138 ° C.
Compound 182: Melting point 112-114 ° C
Compound 183: mp 92-95 ° C.

Compound 184: melting point 140-141 ° C.
Compound 185: Melting point 98-101 ° C
Compound 186: mp 102-105 ° C.
Compound 187: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.57-1.86 (m, 6H), 2.78-2.85 (m, 2H), 3.37-3.41 (m, 2H), 4.00 (s, 3H), 5.30 (s , 2H), 7.01 (d, 1H, J = 7.5 Hz), 7.35-7.55 (m, 5H), 7.70 (dd, 1H, J = 8.2, 7.5 Hz), 8.01 (d, 1H, J = 8.2 Hz) , 9.18 (br-s, 1H).
Compound 188: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 1.32 (t, 3H), 3.50 (s, 2H), 4.07 (s, 3H), 4.27 (q, 2H), 5.29 (s, 2H), 7.03 (d, 1H), 7.34-7.53 (m, 5H), 7.71 (t, 1H), 8.11 (d, 1H), 9.62 (br-s, 1H).
Compound 189: Melting point 118-121 ° C.
Compound 190: mp 134-136 ° C

Compound 191: mp 143-145 ° C
Compound 192: mp 141-143 ° C.
Compound 193: mp 114-115 ° C.
Compound 194: mp 122-125 ° C.
Compound 195: Amorphous; ¹ H-NMR (CDCl ₃ ) 2.21 (s, 3H), 3.36 (s, 2H), 4.02 (s, 3H), 5.30 (s, 2H), 7.03 (d, 1H), 7.35- 7.53 (m, 5H), 7.72 (dd, 1H), 8.15 (d, 1H), 9.15 (s, 1H).
Compound 196: melting point 107-109 ° C.
Compound 197: Amorphous; ¹ H-NMR (CDCl ₃ ) 2.31 (s, 6H), 2.62 (t, 2H, J = 5.5 Hz), 3.98 (s, 3H), 4.29 (t, 2H, J = 5.5 Hz) , 5.25 (s, 2H), 6.95 (d, 1H, J = 7.6 Hz), 7.35-7.45 (m, 4H), 7.50-7.53 (m, 2H), 7.67 (dd, 1H, J = 8.1, 7.6 Hz ), 7.89 (d, 1H, J = 8.1 Hz).

Compound 198: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.88 (tt, 2H, J = 7.4, 6.5 Hz), 2.27 (s, 6H), 2.41 (t, 2H, J = 7.4 Hz), 3.98 (s, 3H), 4.25 (t, 2H, J = 6.5 Hz), 5.26 (s, 2H), 6.96 (dd, 1H, J = 7.6, 0.7 Hz), 7.31 (br-s, 1H), 7.35-7.53 (m , 5H), 7.68 (dd, 1H, J = 8.2, 7.6 Hz), 7.89 (d, 1H, J = 8.2 Hz).
Compound 199: mp 163-167 ° C.
Compound 200: Amorphous; ¹ H-NMR (CDCl ₃ ) 3.16 (s, 3H), 4.00 (s, 3H), 4.19 (s, 2H), 5.24 (s, 2H), 7.04 (d, 1H), 7.33- 7.49 (m, 5H), 7.68 (dd, 1H), 8.04 (d, 1H), 9.22 (s, 1H).
Compound 201: Amorphous; ¹ H-NMR (CDCl ₃ ) 2.99 (s, 3H), 3.02 (dd, 2H), 3.49 (dd, 2H), 3.98 (s, 3H), 5.26 (S, 2H), 7.03 ( d, 1H), 7.34-7.50 (m, 5H), 7.70 (dd, 1H), 8.08 (d, 1H), 8.88 (s, 1H).
Compound 202: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.20-1.39 (m, 5H), 1.52 (s, 9H), 1.67-1.79 (m, 5H), 2.48 (s, 3H), 2.75-2.79 (m , 1H), 5.06 (s, 2H), 6.82 (d, 1H, J = 7.5 Hz), 7.12 (br-s, 1H), 7.63 (dd, 1H, J = 8.2, 7.5 Hz), 7.85 (d, 1H, J = 8.2 Hz).
Compound 203: mp 181 ° -183 ° C.
Compound 204: Amorphous; ¹ H-NMR (CDCl ₃ ) 2.48 (s, 4H), 3.97 (s, 3H), 5.03-5.15 (m, 2H), 5.26 (s, 2H), 5.83-5.92 (m, 1H ), 7.13 (d, 1H), 7.34-7.52 (m, 5H), 7.69 (t, 1H), 7.94 (s, 1H), 8.13 (d, 1H).

Compound 205: mp 126-127 ° C
Compound 206: mp 55-56 ° C
Compound 207: mp 78-79 ° C.
Compound 208: mp 131-134 ° C.
Compound 209: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.47 (s, 9H), 1.58 (d, 3H), 4.00 (s, 3H), 4.35 (br, 1H), 5.27 (s, 2H), 7.018 ( d, 1H), 7.35-7.53 (m, 5H), 7.70 (t, 1H), 8.12 (d, 1H), 8.63 (s, 1H).
Compound 210: mp 164-165 ° C
Compound 211: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.60 (d, 3H), 3.42 (s, 3H), 3.99 (s, 3H), 4.41 (s, 1H), 5.28 (s, 2H), 5.45 ( s, 1H), 7.02 (d, 1H), 7.34-7.52 (m, 5H), 7.70 (t, 1H), 8.14 (d, 1H), 8.78 (s, 1H).

Compound 212: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.50 (s, 9H), 1.57 (s, 3H), 1.99-2.23 (m, 2H), 2.59-2.65 (m, 1H), 4.01 (s, 3H ), 5.27 (s, 2H), 7.02 (d, 1H), 7.30-8.12 (m, 7H), 8.59 (s, 1H).
Compound 213: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.43 (s, 9H), 1.58 (d, 3H), 2.63 (t, 2H), 3.41-3.53 (m, 3H), 3.98 (s, 3H), 5.26 (s, 2H), 7.00 (d, 1H), 7.31-8.11 (m, 8H).
Compound 214: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.53 (s, 3H), 1.66 (s, 3H), 1.87-1.96 (m, 2H), 2.47 8t, 2H), 3.19-3.26 (m, 2H) , 4.03 (s, 3H), 4.74 (s, 1H), 5.27 (s, 2H), 7.00 (d, 1H), 7.31-7.71 (m, 4H), 7.68 (t, t, 1H), 8.10 (d , 1H), 8.22 (s, 1H).
Compound 215: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.46 (s, 4H), 1.59 (s, 9H), 1.96-2.26 (m, 2H), 3.53 (s, 2H), 4.01 (s, 3H), 5.27 (s, 2H), 7.00 (d, 1H), 7.34-8.15 (m, 7H).
Compound 216: Amorphous; ¹ H-NMR (CDCl ₃ ) 2.05 (s, 3H), 2.15-2.82 (m, 4H), 4.01 (s, 3H), 4.98-5.06 (m, 1H), 5.27 (s, 2H ), 7.01 (d, 1H), 7.20-8.12 (m, 11H), 8.11 (d, 1H), 8.98 (s, 1H).
Compound 217: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.51 (s, 9H), 2.27 (s, 3H), 3.97 (s, 3H), 5.30 (s, 2H), 6.92-8.01 (m, 7H).
Compound 218: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.51 (s, 9H), 2.25 (s, 3H), 3.97 (s, 3H), 5.25 (s, 2H), 6.92-7.88 (m, 7H).

Compound 219: Amorphous; ¹ H-NMR (CDCl ₃ ) 0.91 (q, 3H), 1.26 (t, 3), 1.28-1.30 (m, 2H), 2.80 (t, 2H), 5.18 (s, 2H), 7.03-7.35 (m, 4H), 7.63-7.89 (m, 2H).
Compound 220: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.51 (s, 9H), 3.97 (s, 3H), 5.25 (s, 2H), 6.90-7.33 (m, 3H), 7.35 (s, 1H), 7.66 (t, 1H), 7.78 (d, 1H).
Compound 221: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.51 (s, 9H), 3.97 (s, 3H), 5.30 (s, 2H), 6.93 (d, 1H), 7.07-8.01 (m, 2H), 7.65 (t, 1H), 7.87 (d, 1H), 8.01 (s, 1H).
Compound 222: Amorphous; ¹ H-NMR (CDCl ₃ ) 4.00 (s, 3H), 5.34 (s, 2H), 7.12 (d, 1H, J = 7.3 Hz), 7.35-7.68 (m, 8H), 7.83 ( dd, 1H, J = 8.4, 7.3 Hz), 8.04-8.07 (m, 2H), 8.32 (d, 1H, J = 8.4 Hz), 8.95 (br-s, 1H).
Compound 224: mp 98-101 ° C.
Compound 225: Melting point 157-158 ° C

Compound 226: mp 50-51 ° C.
Compound 227: melting point 109-110 ° C.
Compound 228: mp 124-125 ° C.
Compound 229: Melting point 148-149 ° C
Compound 230: Amorphous; ¹ H-NMR (CDCl ₃ ) 4.02 (s, 3H), 4.52 (s, 1H), 5.23 (s, 2H), 6.45 (d, 1H), 6.60 (d, 1H), 7.26- 7.54 (m, 6H).

Compound 230a: Amorphous; ¹ H-NMR (CDCl ₃ ) 4.01 (s <3H), 5.39 (s, 2H), 5.46 (d, 2H), 6.58 (d, 1H), 6.96-7.00 (m, 1H), 7.28-7.82 (m, 11H), 8.93 (d, 1H).
Compound 230b: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.35 (s, 6H), 2.28 (t, 2H), 3.28 (q, 4H), 4.01 (s, 3H), 4.57 (t, 1H), 5.26 ( s, 2H), 5.47 (t, 3H), 6.58 (d, 1H), 7.37 (d, 1H), 7.34-7.55 (m, 6H).
Compound 230c: Amorphous; ¹ H-NMR (CDCl ₃ ) 1.26 (t, 3H), 3.99 (s, 3H), 4.14 (q, 2H), 5.08 (d, 2H), 5.27 (s, 2H), 6.68- 6.92 (m, 2H), 7.51-7.64 (m, 6H).
Compound 230d: Amorphous; ¹ H-NMR (CDCl ₃ ) 0.88-0.99 (m, 6 H), 1.33 (d, 2H, 1.47-1.88 (m, 12H), 4.01 (s, 3H), 4.28-4.32 (m , 1H), 5.25 (s, 2H), 5.62 (q, 1H), 6.67-6.81 (m, 2H), 7.35-7.58 (m, 7H).
Compound 230e: mp 182-184 ° C.
Compound 230f: Visc. Oil; ¹ H-NMR (CDCl ₃ ) 1.57 (s, 6H), 2.28 (d, 2H), 3.28 (s, 6H), 4.01 (s, 3H), 4.57 (t, 1H), 5.26 (s, 2H), 6.58 (d, 1H), 7.37 (d, 1H), 7.34-7.55 (m, 6H).

Compound 246: Melting point 158-159 ° C
Compound 247: melting point 73-75 ° C
Compound 248: mp 135-136 ° C.

  Next, some preparation examples of the bactericide of the present invention will be shown. However, the additives and addition ratios are not limited to these examples, and can be changed in a wide range. The part in a formulation example shows a mass part.

Formulation Example 1 Wetting agent Compound of the present invention 40 parts Clay 53 parts Dioctyl sulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 3 parts The above is uniformly mixed and finely pulverized to hydrate 40% active ingredient. Get the agent.

Formulation Example 2 Emulsion Compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts The above components are mixed and dissolved to obtain an emulsion containing 10% active ingredient.

Formulation Example 3 Powder A compound of the present invention 10 parts Clay 90 parts The above is uniformly mixed and finely pulverized to obtain a powder of 10% active ingredient.

Formulation Example 4 Granules Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctylsulfosuccinate sodium salt 1 part Potassium phosphate 1 part After pulverizing and mixing well, adding water and kneading well, granulation drying As a result, granules containing 5% of the active ingredient are obtained.

Formulation Example 5 Suspension Compound of the present invention 10 parts Polyoxyethylene alkyl allyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts The above is mixed and the particle size is 3 microns or less To obtain a suspension containing 10% of the active ingredient.

Formulation Example 6 Granule wettable powder Compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Lignin sulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzenesulfonic acid sodium salt 5 parts After finely pulverizing, add an appropriate amount of water and knead to make a clay. The clay-like product is granulated and then dried to obtain a granule wettable powder containing 40% of the active ingredient.

(Test Example 1) Tomato plague (PN) control test Tomato seedlings (variety “Regina”, 4-5 leaf stage) cultivated in an unglazed pot were sprayed with the emulsion of Formulation Example 2 at a concentration of 100 ppm active ingredient. After spraying, it was naturally dried at room temperature, sprayed with a zoospore suspension of Phytophthora infestans, and kept for 4 days in a high-humidity constant temperature room (20 ° C.) repeating light and dark every 12 hours. The lesion appearance state on the leaf was compared with no treatment, and the control effect (control value) was obtained.

  Compound Nos. 1-3, 10, 12, 13, 19, 30, 31, 33, 35-37, 39, 41, 42, 45, 61, 69-71, 74, 77, 81-86, 90, 92, 94, 95, 98, 100, 103, 105, 108, 109, 111, 112, 114-121, 123, 129, 132, 136, 137, 139, 140, 142-145, 147, 151-153, 155, 158 to 160, 163, 164, 170 to 172, 175 to 178, 180, 182, 185, 187, 188, 190, 193, 195, 196, 204, 206, 209, 211, 213, 218, 221, 222, Tomato plague control trials were conducted on 226, 236, 237, 239, 240, 243, 245, 247, and 248 compounds. All the compounds had a control concentration of 70% or more at a compound concentration of 100 ppm. The compound numbers correspond to the compound numbers in the above table.

Control value [%]
= [(Severity of untreated section-Severity of treated section) / (Severity of untreated section)]
× 100

(Test Example 2) Antibacterial test A compound was dissolved in dimethyl sulfoxide and diluted to a predetermined double concentration on a 96-well microplate using PSY medium to prepare a drug solution. On the other hand, a dimethyl sulfoxide diluted solution was prepared using a PSY medium to prepare a non-treated group.
A liquid cultured suspension of test bacteria (Pythium aphanidermatum) was mixed with an equal amount of the chemical solution and cultured in the dark at 25 ° C. On the third to seventh days of the culture, the hyphal growth was observed to determine the hyphal elongation inhibition rate.
Compound Nos. 2, 4 to 20, 25, 26, 29 to 31, 33 to 38, 40 to 44, 47 to 53, 61, 62, 64, 65, 68, 70 to 74, 76 to 95, 100 to 105, An antibacterial test was conducted on the compounds 107 to 121, 123 to 126, 128 to 156, 158 to 160, 163 to 165, 168 to 185, 187 to 211, 230b, 230c, 230d, 230e, and 230f. At a concentration of 1 ppm, the hyphal elongation inhibition rate was 50% or more. The compound numbers correspond to the compound numbers in the above table.

  As described above, it can be seen that the oxime compound and the salt thereof of the present invention exhibit an excellent disease control effect against plant diseases, although there are some strengths.

Claims (2)

An oxime compound represented by formula (I) or a salt thereof.

In formula (I),
A represents an unsubstituted or substituted heterocyclic group.
B represents a single bond or an alkylene group which is unsubstituted or has a substituent.
Y represents an unsubstituted or substituted aromatic ring group.
X represents an unsubstituted or substituted aromatic ring group, or an unsubstituted or substituted non-aromatic ring group.   A bactericidal agent comprising at least one selected from the oxime compound or a salt thereof according to claim 1 as an active ingredient.