JPH0892223A - Heterocycle-substituted aniline derivative and agricultural/horticultural germicide with the same as active ingredient - Google Patents

Abstract

PURPOSE: To obtain a new hoterocycle-substituted aniline derivative having excellent disease injury-controlling effect and useful as an agricultural/ horticultural germicide safe to crop. CONSTITUTION: This compound is expressed by formula I[Het is of formula II, III, IV, V (R<1> is H, a 1-4C alkyl, halogen or 1-4C haloalkyl), etc.; R is formula VI-IX (R<2> is a 1-4C alkyl, halogen or 1-4C haloalkyl; R<3> is H or a 1-4C alkyl), etc.], e.g. N- 2-(2-thienyl)phenyl}-2-chloronicotinamide. This compound of formula I is obtained by reaction between a heterocyclic-substituted aniline and a carboxy acid halide in a melt state or in a solvent. Plant disease injuries can be controlled by applying this compound or a germicide containing this compound to plant pathogenic fungi or their inhabited sites.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention is characterized in that a novel heterocyclic-substituted aniline derivative, an agricultural / horticultural fungicide containing the derivative as an active ingredient, and the derivative are applied to plant pathogenic fungi or their habitat. The present invention relates to a method for controlling plant diseases.

[0002]

It has been widely known that a wide variety of carboxylic acid amides have physiological activity as herbicides and fungicides. Among them, benzoic acid amides or heterocyclic carboxylic acid amides are known as fungicides. There are many drugs on the market. For example, 3'-isopropyloxy-2-methylbenzanilide as benzoic acid amide, or α, α, α-trifluoro-3'-isopropyloxy-2-toluanilide is a sterilizer against rice blight, rust of wheat and the like. Marketed as an agent. Also,
As the heterocyclic carboxylic acid amide, 5,6-dihydro-
2-Methyl-1,4-oxathiin-3-carboxyanilide-4,4-dioxide is a chrysanthemum white rust, 3,4-
Dihydro-6-methyl-2H-pyran-5-carboxyanilide is commercially available as a fungicide against wheat rust.

Further, in the case of Pestic. Sci. , 38 ,
1 to 7 (1993), thiazolecarboxylic acid amides inhibit the action of succinate dehydrogenase,
Having activity against Rhizoctonia
Aust. J. Chem. , 36 . 135-147 (1
983) describes that pyrazolecarboxylic acid amides likewise have activity against Rhizoctonia.

On the other hand, in JP-A-5-221,994 and JP-A-6-199,803, an alkyl group, an alkoxy group, an alkenyl group, an alkenyloxy group, an alkynyl group at the o-position of an amino group, Described that various aromatic carboxylic acid anilides substituted with an alkynyloxy group, a cycloalkyl group, a cycloalkenyl group, a cycloalkyloxy group, a cycloalkenyloxy group or a phenyl group have an effect on gray mold (Botrytis bacterium). Has been done. However, the compounds specifically disclosed therein were tested for bactericidal activity against Botrytis cinerea, but the control effect was low and it was not practical.

[0005]

SUMMARY OF THE INVENTION Therefore, an object of the present invention is to provide an agricultural and horticultural fungicide which exhibits an excellent disease control effect and is safe for crops.

[0006]

Means and Actions for Solving the Problems To solve the above problems, the present inventors have studied various carboxylic acid anilide derivatives, and as a result, have a heterocyclic ring at the o-position of an amino group. It was found that the carboxylic acid anilide derivative has a strong controlling effect against Botrytis cinerea,
The present invention has been completed. That is, the present invention provides a compound represented by the general formula (1)
0) A heterocyclic aniline derivative represented by 0), an agricultural and horticultural fungicide containing the derivative as an active ingredient, and a method for controlling plant diseases, which comprises applying the derivative to plant pathogenic fungi or their habitat.

[0007]

[Chemical 10] [However, Het is H1 represented by the following formula (Formula 11).
Represents a heterocyclic group of H11 to

[0008]

[Chemical 11] (In the formula, R ¹ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen atom or a haloalkyl group having 1 to 4 carbon atoms.) R represents G 1 to G 9 represented by the following formula (Formula 12). Means a cyclic group,

[0009]

[Chemical 12] (In the formula, R ² is an alkyl group having 1 to 4 carbon atoms, a halogen atom or a haloalkyl group having 1 to 4 carbon atoms, R ³ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R ⁴ is a halogen atom. The heterocyclic-substituted aniline derivative represented by the general formula (1) of the present invention is a novel compound, and is represented by the reaction formula (1)
It can be produced by the known method shown in 3) by reacting the heterocyclic-substituted aniline represented by the general formula (2) with the carboxylic acid halide represented by the general formula (3) in a molten state or in a solvent.

[0010]

[Chemical 13] (In the formula, Het and R represent the above meanings, and X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.) As a solvent usable in this reaction, any solvent inert to the reaction may be used. For example, aliphatic hydrocarbons such as hexane and petroleum ether, aromatics such as benzene, toluene, chlorobenzene and anisole, ethers such as dioxane, tetrahydrofuran and diethyl ether, nitriles such as acetonitrile and propionitrile. , Esters such as ethyl acetate, dichloromethane, chloroform, 1,
Examples thereof include halogenated hydrocarbons such as 2-dichloroethane, aprotic solvents such as dimethylformamide and dimethylsulfoxide, and mixed solvents thereof can be used.

This reaction may also be carried out in the presence of a base, and as the base, for example, alkali metal and alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide, calcium hydroxide and the like; alkali metal, Alkaline earth metal oxides such as calcium oxide, magnesium oxide; alkali metal and alkaline earth metal hydrides such as sodium hydride, calcium hydride and the like; alkali metal amides such as lithium amide, sodium amide and the like; alkali Metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate, calcium carbonate, magnesium carbonate and the like; alkali metal and alkaline earth metal hydrogen carbonates, such as sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal alkyls, such as Methyllithium, butyric Lithium, phenyl lithium,
Methyl magnesium chloride; alkali metal and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide, dimethoxymagnesium; organic bases such as triethylamine, pyridine, N, N-dimethylaniline, N -Methylpiperidine, lutidine, 4-dimethylaminopyridine and the like can be mentioned, and triethylamine and pyridine can be particularly preferably used. The amount of these bases used is not particularly limited, but is preferably the one represented by the general formula (3)
5 mol% relative to the carboxylic acid chlorides represented by
To 20 mol% excess.

The heterocyclic ring-substituted anilines represented by the general formula (2) and the carboxylic acid chlorides represented by the general formula (3) are generally used in equimolar amounts, but one is used for the other to improve the yield. On the other hand, it may be used in excess of 1 to 20 mol%. The reaction temperature is 0 to 150 ° C, preferably 0 to 40 ° C. Specific examples of the substituent R ¹ of the heterocycle-substituted aniline derivative include a hydrogen atom and a carbon number of 1
To 4 alkyl groups such as methyl, ethyl and isopropyl groups, halogen atoms such as fluorine, chlorine, bromine or iodine atoms, C1 to C4 haloalkyl groups such as trifluoromethyl and difluoromethyl groups, Examples thereof include a fluoromethyl group, a trichloromethyl group and a pentafluoroethyl group.

Specific examples of Het include a furyl group which may be substituted with an alkyl group at any position, for example, 2-furyl, 3-furyl, 5-methyl-2-furyl, 2-methyl-3-furyl. Group etc .; a thienyl group which may be substituted with an alkyl group at any position, for example, 2-thienyl, 3-thienyl, 5-methyl-2-thienyl, 2-methyl-3-
Thienyl, 3-methyl-2-thienyl, 2,5-dimethyl-3-thienyl group, 5-isopropyl-2-thienyl group and the like; isoxazolyl group optionally substituted with an alkyl group at any position, for example, 3- Isoxazolyl, 4-
Isoxazolyl, 5-isoxazolyl, 5-methyl-3-isoxazolyl, 3-methyl-5-isoxazolyl group, etc .; isothiazolyl group optionally substituted with an alkyl group at any position, for example, 3-isothiazolyl, 4
-Isothiazolyl, 5-isothiazolyl, 5-methyl-
3-isothiazolyl, 3-methyl-5-isothiazolyl group, 4-methyl-3-isothiazolyl, 3-methyl-4
-Isothiazolyl group and the like; pyrazolyl group optionally substituted with an alkyl group at any position, for example, 1-methyl-3-
Pyrazolyl, 1-methyl-4-pyrazolyl, 1-methyl-5-pyrazolyl, 3-pyrazolyl, 5-pyrazolyl group and the like; an oxazolyl group which may be substituted with an alkyl group at any position, for example, 2-oxazolyl, 4 -Oxazolyl, 5-oxazolyl, 2-methyl-4-oxazolyl, 2-methyl-5-oxazolyl, 4-methyl-5-
Oxazolyl group and the like; thiazolyl group optionally substituted with an alkyl group at any position, for example, 2-thiazolyl, 4-
Thiazolyl, 5-thiazolyl, 2-methyl-4-thiazolyl, 2-methyl-5-thiazolyl, 4-methyl-5-
Thiazolyl, 5-methyl-4-thiazolyl group, etc .; Pyridyl group which may be substituted with an alkyl group at any position, for example, 2-pyridyl, 3-pyridyl, 4-pyridyl, 6-
Methyl-2-pyridyl group or the like; a pyrimidinyl group which may be substituted with an alkyl group at any position, for example, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 4,6
-Dimethyl-2-pyrimidinyl group and the like; pyrazinyl group optionally substituted with an alkyl group at any position, for example, 2-
Pyrazinyl, 3-methyl-2-pyrazinyl group and the like; pyridazinyl group which may be substituted with an alkyl group at an arbitrary position, for example, 4-methyl-3-pyridazinyl, 3-methyl-4-pyridazinyl group and the like.

On the other hand, specific examples of R ² include a methyl group, an ethyl group, an isopropyl group and the like, which are alkyl groups having 1 to 4 carbon atoms, fluorine, chlorine, bromine or iodine atoms which are halogen atoms, and 1 to 4 carbon atoms. Examples thereof include a trifluoromethyl group, a difluoromethyl group, a fluoromethyl group, a trichloromethyl group, and a pentafluoroethyl group, which are 4 haloalkyl groups, and R ³ is specifically a methyl group having 1 to 4 carbon atoms. Group, ethyl group, isopropyl group, etc., which is a haloalkyl group having 1 to 4 carbon atoms, such as trifluoromethyl group, difluoromethyl group, fluoromethyl group,
Examples thereof include a trichloromethyl group and a pentafluoroethyl group, and specific examples of R ⁴ include a halogen atom such as fluorine, chlorine, bromine or iodine atom.

On the other hand, specifically, R may be substituted with a trifluoromethyl group, a difluoromethyl group, a chlorine atom, a bromine atom or an iodine atom at the 4-position, and a methyl group at the 2-position. A thiazolyl group, eg 2-methyl-4
-Trifluoromethyl-5-thiazolyl group, 2-methyl-4-difluoromethyl-5-thiazolyl group, 2-methyl-4-chloro-5-thiazolyl group, 2-methyl-4-
Iodo-5-thiazolyl group, 4-trifluoromethyl-
5-thiazolyl group etc .; trifluoromethyl group, difluoromethyl group, 1-methyl-4-pyrazolyl group substituted with chlorine atom, bromine atom or iodine atom at 3-position;
A methyl-3-trifluoromethyl-4-pyrazolyl group,
1-methyl-3-difluoromethyl-4-pyrazolyl group, 1-methyl-3-chloro-4-pyrazolyl group, 1-
Methyl-3-bromo-4-pyrazolyl group, 1-methyl-
3-iodo-4-pyrazolyl group, 3-trifluoromethyl-4-pyrazolyl group and the like; 2-methyl-3-furyl group which may be substituted with methyl at 4- and / or 5-position,
For example, 2-methyl-3-furyl group, 2,5-dimethyl-
3-furyl group, 2,4,5-trimethyl-3-furyl group, etc .; methyl group, chlorine atom, bromine atom or iodine atom may be substituted at 2-position, and methyl group may be substituted at 5-position. May be 3-methyl-2-thienyl group, for example, 3-methyl-2-thienyl group, 3-chloro-2-thienyl group, 3-
Iodo-2-thienyl, 3-methyl-2-thienyl group, etc .; phenyl group substituted with trifluoromethyl group, methyl group, chlorine atom, bromine atom or iodine atom at 2-position, for example, 2-chlorophenyl group, 2-bromo Phenyl group, 2
-Iodophenyl group, 2-tolyl group, 2-trifluoromethylphenyl group, etc .; 3-pyridyl group in which chlorine atom, bromine atom or iodine atom is substituted at 2-position, for example, 2-chloro-3-pyridyl group, 2- Bromo-3-pyridyl group, 2-
Iodo-3-pyridyl group, 2-chloro-6-methyl-3
-Pyridyl group and the like; 3-pyrazinyl group substituted with a chlorine atom, a bromine atom or an iodine atom at the 2-position, for example 3-chloro-
2-pyrazinyl group, 3-bromo-2-pyrazinyl group, 3
-Iodo-2-pyrazinyl group and the like; 2-methyl-5,6-
A dihydropyran-3-yl group, a 2-methyl-5,6-dihydro-1,4-oxathin-3-yl group and the like are preferable. Particularly preferred compounds of general formula (1) are shown in Table 1 (Table 1).
To Table 13).

[0016]

[Table 1] Table 1 ──────────────────────────────────── Het R ───── ─────────────────────────────── 2-furyl 2-methyl-4-trifluoromethyl-5-thiazolyl 2-furyl 2-Methyl-4-difluoromethyl-5-thiazolyl 2-furyl 4-trifluoromethyl-5-thiazolyl 2-furyl 4-iodo-5-thiazolyl 2-furyl 1-methyl-3-trifluoromethyl-4-palazolyl 2-furyl 1-methyl-3-iodo-4-parasolyl 2-furyl 2-methyl-3-furyl 2-furyl 2,5-dimethyl-3-furyl 2-furyl 3-methyl-2-thienyl 2-furyl 2 -Chlorophenyl 2-furyl 2-Chloro-3-pyridyl 2-furyl 3-Chloro-2-paradinyl 2-furyl 2-methyl-5,6-dihydroxychloropyran-3-yl 2-furyl 2-methyl-5,6 -Dihydroxy-1,4-oxathiiin-3-yl 3-furyl 2-methyl-4-trifluoromethyl-5-thiazolyl 3-furyl 1-methyl-3-trifluoromethyl-4-parasoleyl 3-furyl 2-chlorophenyl 3-furyl 2-chloro-3-pyridyl 3-furyl 3-chloro-2-paradinyl 3-furyl 2-methyl-5,6-dihydroxy-1,4-oxathiin-3-yl ───────── ────────────────────────────

[0017]

[Table 2] Table 1 (continued) ──────────────────────────────────── Het R ── ────────────────────────────────── 5-methyl-2-furyl 2-methyl-4-trifluoromethyl -5-Thiazolyl 5-Methyl-2-furyl 1-Methyl-3-trifluoromethyl-4-palazolyl 5-methyl-3-furyl 2-chlorophenyl 2-thienyl 2-methyl-4-trifluoromethyl-5-thiazolyl 2-thienyl 2-methyl-4-difluoromethyl-5-thiazolyl 2-thienyl 4-trifluoromethyl-5-thiazolyl 2-thienyl 4-iodo-5-thiazolyl 2-thienyl 1-methyl-3-trifluoromethyl- 4-Pyrazolyl 2-thienyl 1-methyl-3-iodo-4-pyrazolyl 2-thienyl 2-methyl-3-furyl 2-thienyl 2,5-dimethyl-3-furyl 2-thienyl 3-methyl-2-thienyl 2-thienyl 2-chlorophenyl 2-thienyl 2-chloro-3-pyridyl 2-thienyl 3-chloro-2-palladinyl 2-thienyl 2-methyl-5,6-dihydroxychloropyran- 3-yl 2-thienyl 2-methyl-5,6-dihydroxy-1,4-oxathiin-3-yl 3-thienyl 2-methyl-4-trifluoromethyl-5-thiazolyl 3-thienyl 1-methyl-3- Trifluoromethyl-4-pyrazolyl 3-thienyl 2-chlorophenyl 3-thienyl 2-chloro-3-phenyl ──────────────────────────── ─────────

[0018]

[Table 3] Table 1 (continued) ──────────────────────────────────── Het R ── ────────────────────────────────── 3-thienyl 3-chloro-2-paragenyl 3-thienyl 2-methyl -5,6-Dihydroxy-1,4-oxathiiin-3-yl 5-methyl-2-thienyl 2-methyl-4-trifluoromethyl-5-thiazolyl 5-methyl-2-thienyl 1-methyl-3-trifluoro Methyl-4-pyrazolyl 5-methyl-2-thienyl 2-chlorophenyl 5-methyl-2-thienyl 2-chloro-3-pyryl 5-methyl-2-thienyl 3-chloro-2-parasenyl 5-methyl-2-thienyl 2-Methyl-5,6-dihydroxy-1,4-oxathiin-3-yl 5-methyl-4-thienyl 1-methyl-3-trifluoromethyl-4-plasaryl 3-methyl-2-thienyl 1-methyl- 3-trifle Romethyl-4-parasolyl 4-methyl-3-thienyl 1-methyl-3-trifluoromethyl-4-triazolyl 4-methyl-2-thienyl 1-methyl-3-trifluoromethyl-4-parasoryl 2-ethyl-3 -Thienyl 1-methyl-3-trifluoromethyl-4-pyrazolyl 5-isopropyl-2-thienyl 1-methyl-3-trifluoromethyl-4-palazolyl 3-isoxazoaryl 2-methyl-4-trifluoromethyl-5- Thiazolyl 3-isoxazolyl 1-methyl-3-trifluoromethyl-4-pyrazolyl 3-isoxazolyl 1-methyl-3-iodo-4-pyrazolyl 3-isoxazolyl 2-methyl-3-furyl 3-isooxazolyl 3-methyl-2- Thienyl 3-isoxazolyl 2-chlorophenyl 3-isoxazolyl 2-chloro-3-phenyl ────────────────────────── ──────────

[0019]

[Table 4] Table 1 (continued) ──────────────────────────────────── Het R ── ────────────────────────────────── 3-isoxazolyl 3-chloro-2-parasinyl 3-isoxazolyl 2-methyl -5,6-Dihydroxy-1,4-oxathiin-3-yl 4-isoxazolyl 2-methyl-4-trifluoromethyl-5-thiazolyl 4-isoxazolyl 1-methyl-3-trifluoromethyl-4-parasoleyl 4- Isoxazolyl 1-methyl-3-iodo-4-pyrazolyl 4-isoxazolyl 2-methyl-3-furyl 4-isoxazolyl 3-methyl-2-thienyl 4-isooxasoryl 2-chlorophenyl 4-isoxazolyl 2-chloro-3-polybenzyl 4- Isooxazolyl 3-chloro-2-paragenyl 4- Soxazolyl 2-Methyl-5,6-Dichtochloropyran-3-yl 4-Isoxazolyl 2-Methyl-5,6-Dihydroxy-1,4-oxathiin-3-yl 5-Isooxazolyl 2-Methyl-4-trifluoromethyl- 5-Thiazolyl 5-isoxazolyl 1-methyl-3-trifluoromethyl-4-parasoleyl 5-isoxazolyl 1-methyl-3-yodo-4-pyrazolyl 5-isoxazolyl 2-methyl-3-furyl 5-isooxazolyl 3- Methyl-2-thienyl 5-isoxazolyl 2-chlorophenyl 5-isoxazolyl 2-chloro-3-pyridyl 5-isoxazolyl 3-chloro-2-palladinyl 5-isoxazolyl 2-methyl-5,6-dihydroxy-1,4-oxathiin- 3-Ile ────────────────────────────────────

[0020]

[Table 5] Table 1 (continued) ──────────────────────────────────── Het R ── ────────────────────────────────── 5-methyl-3-isoxazolyl 2-methyl-4-trifluoromethyl -5-thiazolyl 5-methyl-3-isooxazolyl 1-methyl-3-trifluoromethyl-4-parasolyl 5-methyl-3-isooxazolyl 2-chlorophenyl 3-isothiazolyl 2-methyl-4-trifluoromethyl-5-thiazolyl 3-isothiazolyl 1-methyl-3-trifluoromethyl-4-pyrazolyl 3-isothiazolyl 1-methyl-3-iodo-4-pyrazolyl 3-isothiazolyl 2-methyl-3-furyl 3-isothiazolyl 3-methyl-2-thienyl 3-isothiazolyl 2-chlorophenyl 3-isothiazolyl 2-chloro -3--3-pyridyl 3-isothiazolyl 3-chloro-2-parasynyl 3-isothiazolyl 2-methyl-5,6-dihydroxy-chloro-thyl-3-yl 3-isothiazolyl 2-methyl-5,6-dihydroxy-1,4-oxathiin -3-yl 4-isothiazolyl 2-methyl-4-trifluoromethyl-5-thiazolyl 4-isothiazolyl 1-methyl-3-trifluoromethyl-4-palazolyl 4-isothiazolyl 1-methyl-3-yodo-4 -Pyrazolyl 4-isothiazolyl 2-methyl-3-furyl 4-isothiazolyl 3-methyl-2-thienyl 4-isothiazolyl 2-chlorophenyl 4-isothiazolyl 2-chloro-3-pyrylyl 4-isothiazolyl 3-chloro-2-parasenyl ───────────────────────────────────

[0021]

[Table 6] Table 1 (continued) ──────────────────────────────────── Het R ── ────────────────────────────────── 4-isothiazolyl 2-methyl-5,6-dihydroxyborolane-3- 4-isothiazolyl 2-methyl-5,6-dihydroxy-1,4-oxathiin-3-yl 5-isothiazolyl 2-methyl-4-trifluoromethyl-5-thiazolyl 5-isothiazolyl 1-methyl-3-trifluoro Methyl-4-pyrazolyl 5-isothiazolyl 1-methyl-3-iodo-4-pyrazolyl 5-isothiazolyl 2-methyl-3-furyl 5-isothiazolyl 3-methyl-2-thienyl 5-isothiazolyl 2-chlorophenyl 5-isothiazolyl 2- Chloro-3-pyridyl 5-isothiazolyl 3-chloro-2-pyrazinyl 5-isothiyl Solyl 2-methyl-5,6-dihydroxy-pyran-3-yl 5-isothiazolyl 2-methyl-5,6-dihydroxy-1,4-oxathiin-3-yl 5-methyl-3-isothiazolyl 2-methyl-4- Trifluoromethyl-5-thiazolyl 5-methyl-3-isothiazolyl 1-methyl-3-trifluoromethyl-4-pyrazolyl 5-methyl-3-isothiazolyl 2-chlorophenyl 1-methyl-3-pyrazolyl 2-methyl-4- Trifluoromethyl-5-thiazolyl 1-methyl-3-pyrazolyl 1-methyl-3-trifluoromethyl-4-pyrazolyl 1-methyl-3-pyrazolyl 1-methyl-3-iodo-4-pyrazolyl 1-methyl-3 -Pyrazolyl 2-methyl-3-furyl 1-methyl-3-pyrazolyl 3-methyl-2-thienyl 1-methyl-3-pyrazolyl 2-chlorophenyl ───────────────── ────────────── ────

[0022]

[Table 7] Table 1 (continued) ──────────────────────────────────── Het R ── ────────────────────────────────── 1-methyl-3-pyrazolyl 2-chloro-3-pyrylyl 1- Methyl-3-pyrazolyl-3-chloro-2-parasinyl 1-methyl-3-pyrazolyl 2-methyl-5,6-dihydroxy-chloropyran-3-yl 1-methyl-3-parasoyryl 2-methyl-5,6-dihydroxy- 1,4-oxathiin-3-yl 1-methyl-5-pyrazolyl 2-methyl-4-trifluoromethyl-5-thiazolyl 1-methyl-5-pyrazolyl 1-methyl-3-trifluoromethyl-4-pyrazolyl 1 -Methyl-5-pyrazolyl 1-methyl-3-iodo-4-pyrazolyl 1-methyl-5-pyrazolyl 2-chlorophenyl 1-methyl-5-pyrazolyl 2-chloro -3-Pyryl 1-Methyl-5-Plasazolyl 3-Chloro-2-Plasagenyl 1-Methyl-5-Plasazolyl 2-Methyl-5,6-Dihydroxy-1,4-oxathiiin-3-yl 2-Oxazolyl 2-Methyl -4-trifluoromethyl-5-thiazolyl 2-oxazolyl 1-methyl-3-trifluoromethyl-4-pyrazolyl 2-oxazolyl 1-methyl-3-iodo-4-parazolyl 2-oxazolyl 2-methyl-3-furyl 2-Oxazolyl 3-Methyl-2-thienyl 2-Oxazolyl 2-Chlorophenyl 2-Oxazolyl 2-Chloro-3-Pyroxyl 2-Oxazolyl 3-Chloro-2-Perasynyl 2-Oxazolyl 2-Methyl-5,6-Jychetro-1 , 4-Oxathiiin-3-yl 4-oxazolyl 2-methyl-4-trifluoromethyl-5-thiazolyl ─────────────────────────── ──────────

[0023]

[Table 8] Table 1 (continued) ──────────────────────────────────── Het R ── ────────────────────────────────── 4-Oxazolyl 1-methyl-3-trifluoromethyl-4-parasoleyl 4-Oxazolyl 1-Methyl-3-iodo-4-pyrazolyl 4-Oxazolyl 2-Methyl-3-furyl 4-Oxazolyl 3-Methyl-2-thienyl 4-Oxazolyl 2-Chlorophenyl 4-Oxazolyl 2-Chloro-3-Phyryl 4-Oxazolyl 3-chloro-2-parasynyl 4-isooxazolyl 2-methyl-5,6-dihydroxy-1,4-oxathiiin-3-yl 5-oxasolyl 2-methyl-4-trifluoromethyl-5-thiazolyl 5- Oxazolyl 1-methyl-3-trifluoromethyl-4-palazolyl 5-oxazolyl 2- Lolophenyl 5-oxasoyryl 2-chloro-3-pyridyl 5-oxasolyl 3-chloro-2-parasynyl 5-oxasolyl 2-methyl-5,6-dihydroxy-1,4-oxathiiin-3-yl 2-methyl-3-oxasazolyl 2-Methyl-4-trifluoromethyl-5-thiazolyl 2-thiazolyl 2-methyl-4-trifluoromethyl-5-thiazolyl 2-thiazolyl 1-methyl-3-trifluoromethyl-4-parasolyl 2-thiazolyl 1- Methyl-3-iodo-4-pyrazolyl 2-thiazolyl 2-methyl-3-furyl 2-thiazolyl 3-methyl-2-thienyl 2-thiazolyl 2-chlorophenyl ──────────────── ─────────────────────

[0024]

[Table 9] Table 1 (continued) ──────────────────────────────────── Het R ── ────────────────────────────────── 2-thiazolyl 2-chloro-3-polyethyl 2-thiazolyl 3-chloro -2-Pyrazinyl 2-thiazolyl 2-methyl-5,6-dihydroxy-1,4-oxathiin-3-yl 4-thiazolyl 2-methyl-4-trifluoromethyl-5-thiazolyl 4-thiazolyl 1-methyl-3 -Trifluoromethyl-4-pyrazolyl 4-thiazolyl 1-methyl-3-iodo-4-pyrazolyl 4-thiazolyl 2-methyl-3-furyl 4-thiazolyl 3-methyl-2-thienyl 4-thiazolyl 2-chlorophenyl 4- Thiazolyl 2-chloro-3-pyridyl 4-thiazolyl 3-chloro-2-parasinyl 4-thiazolyl 2-methyl-5,6- `` Hitoro-1,4-oxathiin-3-yl 5-thiazolyl 2-methyl-4-trifluoromethyl-5-thiazolyl 5-thiazolyl 1-methyl-3-trifluoromethyl-4-parasolyl 5-thiazolyl 2-chlorophenyl 5-thiazolyl 2-chloro-3-pyroxyl 5-thiazolyl 3-chloro-2-parasynyl 5-thiazolyl 2-methyl-5,6-dihydroxy-1,4-oxathiin-3-yl 2-methyl-4-thiazolyl 2 -Methyl-4-trifluoromethyl-5-thiazolyl 2-pyryl 2-methyl-4-trifluoromethyl-5-thiazolyl 2-trifluoromethyl-5-thiazolyl ────────── ──────────────────────────

[0025]

[Table 10] Table 1 (continued) ──────────────────────────────────── Het R ── ────────────────────────────────── 2-Puri 4-4-Yodo-5-thiazolyl 2-Prisil 1 -Methyl-3-trifluoromethyl-4-pyrazolyl 2-pyryl 1-methyl-3-iodo-4-pyrazolyl 2-pyryl 2-methyl-3-furyl 2-polysilyl 3-methyl-2-thienyl 2-pyryl 2 -Chlorophenyl 2-Pyridine 2-Chloro-3-Pyryl 2-Pyryl 3-Chloro-2-Palladinyl 2-Pyryl 2-Methyl-5,6-Dihydroxy-1,4-oxathiin-3-yl 3-Pyryl 2-Chloro -3-Pyryl 4-Pyryl 2-Chloro-3-Pyryl 6-Methyl-2-Pyryl 2-Methyl-4-trifluorome Cyl-5-thiazolyl 6-methyl-2-pyryl 1-methyl-3-trifluoromethyl-4-pyrazolyl 2-pyrimidinyl 2-methyl-4-trifluoromethyl-5-thiazolyl 2-polyimidinyl 4-trifluoromethyl- 5-thiazolyl 2-pyrimidinyl 4-yo-do-5-thiazolyl 2-pyrimidinyl 1-methyl-3-trifluoromethyl-4-pyrazolyl 2-pyrimidinyl 1-methyl-3-iodo-4-pyrazolyl 2-purimidinyl 2- Methyl-3-furyl 2-polyimidinyl 3-methyl-2-thienyl 2-purimidinyl 2-chlorophenyl ────────────────────────────── ───────

[0026]

[Table 11] Table 1 (continued) ──────────────────────────────────── Het R ── ────────────────────────────────── 2-Polimidinyl 2-chloro-3-Pyrimidinyl 2-Poriimidinyl 3-chloro -2-Pyrazinyl 2-Pyrimidinyl 2-Methyl-5,6-Dihydroxy-1,4-oxathiin-3-yl 4-Phyrimidinyl 2-Methyl-4-trifluoromethyl-5-thiazolyl 4-Phriimidinyl 4-trifluoromethyl -5-thiazolyl 4-pyrimidinyl 4-iodo-5-thiazolyl 4-pyrimidinyl 1-methyl-3-trifluoromethyl-4-pyrazolyl 4-pyrimidinyl 1-methyl-3-yo-do-4-pyrazolyl 4-hyrimidinyl 2 -Methyl-3-furyl 4-pyrimidinyl 3-methyl-2-thienyl 4-hi Polyimidinyl 2-chlorophenyl 4-pyrimidinyl 2-chloro-3-pyridyl 4-pyrimidinyl 3-chloro-2-paradinyl 4-pyrimidinyl 2-methyl-5,6-dihydroxy-1,4-oxathiiin-3-yl 5-purimidinyl 2-Methyl-4-trifluoromethyl-5-thiazolyl 5-pyrimidinyl 1-methyl-3-trifluoromethyl-4-pyrazolyl 5-pyrimidinyl 1-methyl-3-iodo-4-parasolyl 5-polyimidinyl 2-methyl- 3-furyl 5-purimidinyl 3-methyl-2-thienyl 5-purimidinyl 2-chlorophenyl 5-purimidinyl 2-chloro-3-puryl ────────────────────── ───────────────

[0027]

[Table 12] Table 1 (continued) ──────────────────────────────────── Het R ── ────────────────────────────────── 5-Polimidinyl 3-Chloro-2-Peragenyl 5-Poriimidinyl 2-methyl -5,6-Dihydroxy-1,4-oxathiiin-3-yl 4,6-dimethyl-2-pyrimidinyl 2-methyl-4-trifluoromethyl-5-thiazolyl 4,6-dimethyl-2-pyrimidinyl 1-methyl -3-Trifluoromethyl-4-Plasazolyl 2-Plasadienyl 2-Methyl-4-trifluoromethyl-5-Thiazolyl 2-Plasadienyl 4-Trifluoromethyl-5-Thiazolyl 2-Plasaenyl 1-Methyl-3-trifluoromethyl -4-Polasoryl 2-Poragenyl 1-Methyl-3-iodo-4-Porasolyl 2-Porajini 2-Methyl-3-furyl 2-Plasalinyl 3-Methyl-2-thienyl 2-Plasalinyl 2-Chlorophenyl 2-Plasalinyl 2-Chloro-3-Purryl 2-Parasinyl 3-Chloro-2-Plasalinyl 2-Methyl-2-methyl -5,6-Dihydroxy-1,4-oxathiiin-3-yl 3-methyl-2-parasynyl 2-chloro-3-phenyl 5,6-dimethyl-2-parasynyl 2-methyl-4-trifluoromethyl-5 -Thiazolyl 2-Pytridenyl 2-Methyl-4-trifluoromethyl-5-Thiazolyl 2-Pytridinyl 4-trifluoromethyl-5-Thiazolyl 2-Phitridienyl 1-Methyl-3-trifluoromethyl-4-Polasolyl 2-Phitridienyl 1 -Methyl-3-yo-do-4-pyrazolyl 2-Pyridinyl 2-chlorophenyl ───────────────────────────── ───────

[0028]

[Table 13] Table 1 (continued) ──────────────────────────────────── Het R ── ────────────────────────────────── 2-polydiphenyl 2-methyl-3-furyl 2-polydiphenyl-3-methyl -2-thienyl 2-pyridinyl 2-chlorophenyl 2-pyridinyl 2-chloro-3-pyridyl 2-pyridinyl 3-chloro-2-paradinyl 2-polydienyl 2-methyl-5,6-dihydroxy-1,4-oxathiin-3 -Il ────────────────────────────────────

In the present invention, the compound represented by the general formula (1) is a gray mold disease of cucumber, tomato, strawberry, grape and the like.
( Botrytis cinerea ) and powdery mildew ( Sphaero ) of cucurbits
theca fuliginea ), powdery mildew of wheat ( Erysiphe gram
inis f. sp. hordei , f. sp. tritici ), strawberry powdery mildew ( Sphaerotheca humuli ), grape powdery mildew ( Uncinula)
necator ), apple powdery mildew ( Podosphaera leucotrich
a ), apple scab ( Venturia inaequalis ), pear scab
( Venturia nashicola ), apple scab ( Gymnosporangium
yamadae ), pear black spot ( Alternaria kikuchiana ), apple spot leaf spot ( Alternaria mali ), rust of wheat ( Pucc)
inia striiformis, P. graminis, P . recondita, P. ho
rdei ), etc. shows an excellent control effect.

When the compound represented by the general formula (1) according to the present invention is used as an agricultural and horticultural fungicide, the raw material may be used as it is for the plant to be treated, but it is generally inactive. Mixing with a liquid carrier or a solid carrier, powders, wettable powders, flowables, which are usually used formulation forms,
Used as emulsions, granules and other commonly used forms of formulations. Further, an auxiliary agent can be added if necessary for formulation. The term "carrier" as used herein means a synthetic or natural inorganic or organic substance formulated to help the active ingredient reach the site to be treated and to facilitate the storage, transportation and handling of the active ingredient compound. . The carrier may be either solid or liquid as long as it is usually used for agricultural and horticultural agents, and is not limited to a particular carrier.

Examples of solid carriers include clays such as montmorillonite and kaolinite, diatomaceous earth, clay, talc, vermiculite, gypsum, calcium carbonate, silica gel, inorganic substances such as ammonium sulfate, soybean powder, sawdust, and wheat flour. Examples include vegetable organic substances and urea. As the liquid carrier, aromatic hydrocarbons such as toluene, xylene and cumene, paraffin hydrocarbons such as kerosene and mineral oil,
Examples thereof include ketones such as acetone and methyl ethyl ketone, ethers such as dioxane and diethylene glycol dimethyl ether, alcohols such as methanol, ethanol, propanol and ethylene glycol, dimethylformamide, dimethyl sulfoxide and water.

In order to further enhance the efficacy of the compound of the present invention, the following auxiliary agents may be used alone or in combination depending on the purpose, taking into consideration the dosage form of the preparation, the application scene, etc. . As the auxiliary agent, a surfactant, a binder (for example, ligninsulfonic acid, alginic acid, polyvinyl alcohol, gum arabic, CMC sodium, etc.) usually used in agricultural and horticultural chemicals, a stabilizer (for example, phenol for antioxidant) Compounds, thiol compounds or higher fatty acid esters, phosphates as pH adjusters, and sometimes light stabilizers), etc., can be used alone or in combination as required. Further, in some cases, an industrial bactericidal agent, an antibacterial and antifungal agent, etc. may be added for antibacterial and antifungal agents.

The auxiliary agent will be described in more detail. Emulsification,
Anionic interfaces such as lignin sulfonate, alkylbenzene sulfonate, alkyl sulfate ester salt, polyoxyalkylene alkyl sulfate salt, polyoxyalkylene alkyl phosphate ester salt for the purpose of dispersing, spreading, wetting, binding, stabilizing, etc. Activator, polyoxyalkylene alkyl ether, polyoxyalkylene alkyl aryl ether, polyoxyalkylene alkyl amine, polyoxyalkylene alkyl amide, polyoxyalkylene alkyl amide, polyoxyalkylene alkyl thioether, polyoxyalkylene fatty acid ester, glycerin fatty acid ester, Nonionic surfactant such as sorbitan fatty acid ester, polyoxyalkylene sorbitan fatty acid ester, polyoxypropylene polyoxyethylene block polymer Agents, calcium stearate, lubricants such as wax, stabilizers such as isopropyl hydroperoxide diene phosphate, other cellulose, carboxymethyl cellulose, casein, gum arabic, and the like. However, these components are not limited to those described above.

The content of the compound represented by the general formula (1) in the agricultural and horticultural fungicide according to the present invention varies depending on the formulation form, but is usually 0.05 to 20% by weight for powders and 0 for wettable powders. 1-80% by weight, 1-50 for emulsion
% By weight, 1 to 50% by weight in a flowable formulation, 1 to 80% by weight in a dry flowable formulation, preferably
0.5 to 5% by weight for powders, 5 to 80% by weight for wettable powders, 0.5 to 8% by weight for granules, 5 to 20% by weight for emulsions, 5 to 30% by weight for flowable formulations and dry flowers. Bull formulation is 5 to 50% by weight. The content of the auxiliary agent is 0 to 80% by weight, and the content of the carrier is 100% by weight minus the contents of the active ingredient compound and the auxiliary agent.

Examples of the application method of the composition of the present invention include seed disinfection, foliage spraying, etc., but any application method usually used by those skilled in the art is sufficiently effective. The application rate and application concentration vary depending on the target crop, target disease, degree of disease occurrence, compound dosage form, application method and various environmental conditions, but when sprayed, the amount of active ingredient is 50 to 1,000 g per hectare. Is suitable, and preferably 100 to 500 g per hectare. When a wettable powder, a flowable agent or an emulsion is diluted with water and sprayed, the dilution ratio is appropriately 200 to 20,000 times, and preferably 1,000 to 5,000 times.

The agricultural and horticultural fungicides of the present invention can be used not only as a mixture with other fungicides, insecticides, herbicides and plant growth regulators, soil improvers or fertilizers, but also with them. Mixed formulations are also possible. Examples of the fungicides include triadimefon, hexaconazole, prochloraz, azole fungicides such as triflumizole, metalaxyl, acylalanine fungicides such as oxadixyl, thiophanate methyl, benzimidazole fungicides such as benomyl, manzeb and the like. Examples of the dithiocarbamate fungicides and tetrachloroisophthalonitrile, sulfur and the like, insecticides such as fenitrothion, diazinon, pyridafenthion, chlorpyrifos, marathon,
Fentate, dimethoate, methylthiomethone, prothiophos, DDVP, acephate, salicione, E
Examples include phosphorus insecticides such as PN, carbamate insecticides such as NAC, MTMC, BPMC, pirimicarb, carbosulfan, and mesomil, and pyrethroid insecticides such as etofenprox, permethrin, and fenvalerate, but are not limited thereto. It is not something that will be done.

[0037]

EXAMPLES Next, the compounds of the present invention will be described more specifically with reference to examples. Example 1 N- {2- (2-thienyl) phenyl} -2-chloronicotinic acid amide (Compound No. 1) 0.6 g of 2-chloronicotinic acid was heated under reflux with 5 ml of thionyl chloride for 1.5 hours, and concentrated under reduced pressure. To prepare a carboxylic acid chloride. Tetrahydrofuran 10
Dissolve in ml and add 0.53 g of pyridine. A solution of 0.56 g of 2- (2-thienyl) aniline in 1 ml of tetrahydrofuran was added to this solution, and the mixture was stirred at room temperature for 1 hour. The reaction solution was discharged into ice water and extracted with ethyl acetate. The organic layer was washed successively with 5% hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was suction filtered to obtain 0.71 g of the desired product (yield: 76
%) Was obtained. Melting point 132 to 133 ° C ¹ H-NMR (CDCl ₃ , δ value): 7.11 to 7.19 (m, 2H), 7.23 (m, 1H), 7.3
5 to 7.47 (m, 4H), 8.17 (dd, J = 7.4,2.2Hz, 1H), 8.46 to 8.54
(m, 3H)

Example 2 N- {2- (5-methyl-2-thienyl) phenyl}-
2-chloronicotinic acid amide (Compound No. 2) 0.75 g of 2-chloronicotinic acid was added to 6 ml of thionyl chloride.
The mixture was heated under reflux for 1.5 hours and concentrated under reduced pressure to prepare carboxylic acid chloride. Tetrahydrofuran 1
Dissolve in 0 ml and add 0.53 g of pyridine. To this solution was added 2- (5-methyl-2-thienyl) aniline.
Add a solution of 7 g of tetrahydrofuran in 1 ml, and add 1 at room temperature.
Stir for hours. The reaction solution was discharged into ice water and extracted with ethyl acetate. The organic layer was washed successively with 5% hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, and dried over magnesium sulfate. The solvent is evaporated under reduced pressure, and the resulting oily substance is purified by column chromatography (eluted with ethyl acetate / n-hexane = 3/7) to obtain 0.5 g of the desired product (yield 42%). It was
Melting point 117-118 ° C ¹ H-NMR (CDCl ₃ , δ value): 2.54 (s, 3H), 6.75 (d, J = 2.2, 1H), 6.9
1 (d, J = 3.6,1H), 7.20 (m, 1H), 7.35-7.44 (m, 3H), 8.16 (dd,
J = 7.3,2.2,1H), 8.46 (m, 2H), 8.60 (brs, 1H)

Example 3 N- {2- (2-pyridyl) phenyl} -2-chloronicotinic acid amide (Compound No. 3) Carboxylic acid chloride was obtained from 0.6 g of 2-chloronicotinic acid in the same manner as in Example 1. Prepare. This is dissolved in 10 ml of tetrahydrofuran, 0.53 g of pyridine is added, and 0.52 of 2- (2-pyridyl) aniline is added to this solution.
A solution of 1 g of tetrahydrofuran in 1 ml was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was discharged into ice water, extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution, and dried over magnesium sulfate. The solution was concentrated under reduced pressure, the solvent was distilled off, and suction filtration was carried out to obtain 0.62 g of the desired product (yield 64%). Melting point 120 to 121.5 ° C. ¹ H-NMR (CDCl ₃ , δ value): 7.24 to 7.28 (m, 3H), 7.34 to 7.38 (m, 1
H), 7.47 ~ 7.52 (m, 1H), 7.71 (dd, J = 8.1,1.5,1H), 7.78 (d, J
= 8.1,1H), 7.84 to 7.88 (m, 1H), 8.05 (dd, J = 8.1,1.5,1H), 8.
45〜8.50 (m, 2H), 8.68 (d, J = 8.8,1H)

Example 4 N- {2- (3-pyridyl) phenyl} -2-chloronicotinic acid amide (Compound No. 4) Example 1 was repeated except that 2- (3-pyridyl) aniline was used as the aniline component. The reaction was performed in exactly the same manner as in (1) to give 0.52 g of the desired product (yield 54%). Melting point 169-17
0.5 ° C. ¹ H-NMR (CDCl ₃ , δ value): 7.29 to 7.41 (m, 4H), 7.49 to 7.53 (m, 1
H), 7.78 (dd, J = 8.1,2.2,1H), 8.11 (dd, J = 8.1,2.2,1H), 8.2
9 (d, J = 8.1,2H), 8.41 (m, 1H), 8.58 ~ 8.62 (m, 2H)

Example 5 N- {2- (4-pyridyl) phenyl} -2-chloronicotinic acid amide (Compound No. 5) Example 1 was repeated except that 2- (4-pyridyl) aniline was used as the aniline component. The reaction was performed in exactly the same manner as in (1) to give 0.4 g of the desired product (yield 42%). Melting point 161-163
¹ H-NMR (CDCl ₃ , δ value): 7.28 to 7.37 (m, 5H), 7.51 (m, 1H), 8.0
9 (m, 1H), 8.18 (brs, 1H) 8.28 (d, J = 8.0,1H), 8.44 (dd, J = 5.
1,2.2,1H), 8.66 (m, 2H)

Example 6 N- {2- (2-thienyl) phenyl} -1-methyl-
3-Trifluoromethylpyrazole-4-carboxylic acid amide (Compound No. 6) 1-Methyl-3-trifluoromethylpyrazole-4-
0.25 g of carboxylic acid was heated under reflux with 3 ml of thionyl chloride for 1.5 hours and concentrated under reduced pressure to prepare carboxylic acid chloride. This is dissolved in 7 ml of tetrahydrofuran and 0.2 g of pyridine is added. 2-in this solution
A solution of 0.23 g of (2-thienyl) aniline in 1 ml of tetrahydrofuran was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was discharged into ice water and extracted with ethyl acetate. The organic layer was washed successively with 5% hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, and dried over magnesium sulfate. Concentrated under reduced pressure to remove the solvent,
After suction filtration, 0.36 g (yield 78%) of the desired product was obtained.
Melting point 170-172 ° C ¹ H-NMR (CDCl ₃ , δ value): 3.96 (S, 3H), 7.11 to 7.25 (m, 2H), 7.3
2 to 7.46 (m, 4H), 7.84 (S, 1H), 7.91 (brs, 1H), 8.35 (d, J = 8.
(8,1H)

Example 7 N- {2- (2-pyridyl) phenyl} -1-methyl-
3-Trifluoromethylpyrazole-4-carboxylic acid amide (Compound No. 7) 1-Methyl-3-trifluoromethylpyrazole-4-
0.46 g of carboxylic acid was heated under reflux with 3 ml of thionyl chloride for 1.5 hours and concentrated under reduced pressure to prepare carboxylic acid chloride. This is dissolved in 7 ml of tetrahydrofuran and 0.2 g of pyridine is added. 2-in this solution
A solution of 0.5 g of (2-pyridyl) aniline in 1 ml of tetrahydrofuran was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was discharged into ice water, extracted with ethyl acetate, the organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, and dried over magnesium sulfate. The solution was concentrated under reduced pressure, the solvent was distilled off, and suction filtration was performed to obtain 0.59 g of the desired product (yield 80%).

¹ H-NMR (CDCl ₃ , δ value): 3.93 (S, 3H), 7.10 (d, J
= 8.1,1H), 7.37 to 7.48 (m, 8H), 8.37 (s, 1H) Some of the compounds of the present invention prepared by such Examples are shown in Table 2 (Tables 14 and 15).

[0045]

[Table 14] Table 2 ──────────────────────────────────── Compound No. Het R Melting point ( ℃) ─────────────────────────────────── 12-thienyl 2-chloro-3-phenyl 132- 133 2 5-Methyl-2-thienyl 2-chloro-3-phenyl 117-118 3 2-poly 2-chloro-3-phenyl 120-121.5 4 3-poly 2-chloro-3-phenyl 169-170.5 5 4- Poly 2-chloro-3-pyridyl 161-163 6 2-thienyl 1-methyl-3-trifluoromethyl 171.5-173 pyrazol-4-yl 7 2-polyyl 1-methyl-3-trifluoromethyl oil Il 8 2-thienyl 2-chlorophenyl 107-108 9 2-thienyl 2-methyl-4-trifluoromethyl 103-104 thiazol-5-yl 10 2- Oxazolyl 1-methyl-3-trifluoromethyl 195 to 198 Parasol-4-yl 11 2-Oxazolyl 2-methyl-4-trifluoromethyl 125 to 127 Thiazol-5-yl 12 5-Oxazolyl 1-methyl-3-tri Fluoromethyl 132-133 Pyrazol-4-yl 13 5-Oxazolyl 2-methyl-4-trifluoromethyl 152-153 Thiazol-5-yl ─────────────────── ─────────────────

[0046]

[Table 15] Table 2 (continued) ──────────────────────────────────── Compound No. Het R Melting point (℃) ─────────────────────────────────── 14 2-furyl 1-methyl-3- Trifluoromethyl 134-135 Pyrazol-4-yl 15 2-furyl 2-methyl-4-trifluoromethyl 129-130 Thiazol-5-yl 16 3-isoxazolyl 2-methyl-4-trifluoromethyl 165-167 Thiazol- 5-yl 17 4-polyimidinyl 2-methyl-4-trifluoromethyl 200-202 thiazol-5-yl 18 4-pyrimidinyl 2-chlorophenyl 139-142 19 4-polyimidinyl 1-methyl-3-trifluoromethyl 192.5-194.5 Pyrazol-4-yl 20 5-polyimidinyl 1-methyl-3-trifluoromethyl 193 to 195 Pyrazol-4-yl ────────────────────────────────────

Reference Example 1 N- (2-isopropylphenyl) -2-methyl-4-
Trifluoromethylthiazole-5-carboxylic acid amide (reference compound A, described in JP-A-5-221994) 2-methyl-4-trifluoromethylthiazole-5-carboxylic acid as carboxylic acid and 2-as aniline It was synthesized by the same method as in Example 1 except that isopropylaniline was used. Melting point 114-115 [deg.] C.

Reference Example 2 N- (2-isopropylphenyl) -2-chloronicotinic acid amide (control compound B, JP-A 5-221,994)
The description was made in the same manner as in Example 1 except that 2-isopropylaniline was used as aniline. Melting point 123-1
24.5 ° C. Formulation Example and Physiological Test Example Next, formulation examples and test examples of the agricultural and horticultural fungicide according to the present invention will be shown.

Formulation Example 1 Dust 3 parts of compound No. 1, 20 parts of diatomaceous earth, 3 parts of clay
0 parts and 47 parts of talc are uniformly pulverized and mixed to give a powder 10
I got 0 copies.

Formulation Example 2 Wettable powder 25 parts of the compound of Compound No. 1, 47 parts of diatomaceous earth, 25 parts of white clay, 1 part of sodium lignin sulfonate and 2 parts of sodium alkylbenzene sulfonate are uniformly pulverized and mixed to obtain a wettable powder 100. I got a part.

Formulation Example 3 Wettable Powder 50 parts of the compound of Compound No. 1, 40 parts of talc, 5 parts of sodium lauryl phosphate and 5 parts of sodium naphthalenesulfonate were mixed to obtain 100 parts of a wettable powder.

Formulation Example 4 Wettable powder 50 parts of the compound of Compound No. 2, 10 parts of sodium lignin sulfonate, 5 parts of sodium alkylnaphthalene sulfonate, 10 parts of white carbon and 25 diatomaceous earth
Parts were mixed and pulverized to obtain 100 parts of a wettable powder.

Formulation Example 5 Emulsion 10 parts of compound No. 2, 10 parts of cyclohexane,
60 parts of xylene and 20 parts of sorbole (surfactant manufactured by Toho Kagaku) were uniformly dissolved and mixed to obtain 100 parts of emulsion.

Formulation Example 6 Floating Agent 40 parts of the compound of Compound No. 2, 3 parts of carboxymethyl cellulose, 2 parts of sodium lignin sulfonate, 1 part of dioctyl sulfosuccinate sodium salt and 54 parts of water.
Part is wet pulverized with a sand grinder, and a flowable agent 1
I got 00 parts. Next, the efficacy of the compound of the present invention as an agricultural and horticultural fungicide will be described with reference to test examples. In addition, in the test example, the compound of the above reference example was used as a control agent.

Test Example 1 Green Bean Mold Control Control Test In accordance with Formulation Example 3, green beans (variety: Tsurunashi Top Crop) grown in a plastic pot having a diameter of 7.5 cm in a greenhouse until two cotyledons were developed were grown. The prepared wettable powder was diluted to a predetermined concentration and sprayed at 50 ml per 4 pots. Conidiospore suspension (1 ×) prepared from Botrytis cinerea (MBC resistant) cultured on PDA medium after the drug solution was dried
10 ⁵ cells / ml) were spray-inoculated on the cotyledons, and 20-23
It was kept in a greenhouse at ℃ and humidity of 95% or more for 7 days. Seven days after the inoculation, the area occupied by gray mold disease lesions per leaf of kidney bean was examined according to the following indexes. The results are shown in Table 3 (Table 1
6, 17).

As a control compound A, N- (2-isopropylphenyl) -2-methyl-4-trifluoromethylthiazole-5-carboxylic acid amide (Japanese Patent Laid-Open Publication No. HEI 5-58
221), and N- (2-isopropylphenyl) -2-chloronicotinic acid amide (described in JP-A-5-221994).

Degree of disease 0: No disease 1: Area of lesions is 5% or less 2: Area of lesions is 5 to 25% 3: Area of lesions is 25 to 50% 4: Area of lesions is 50% The average value of each treatment group and non-treatment group was defined as the disease severity. Control value (%) = (1-degree of disease in treated area / degree of disease in untreated area) × 100

[0058]

[Table 16]

[0059]

[Table 17]

Test Example 2 Strawberry Gray Mold Disease Control Test Strawberries (cultivar: Onamine) grown to fruit set in a unglazed pot with a diameter of 9 cm in a greenhouse were adjusted to a predetermined concentration with a wettable powder prepared according to Formulation Example 3. Diluted and sprayed with 50 ml per 3 pots. Conidiospore suspension prepared from Botrytis cinerea (MBC resistant) cultured on PDA medium after the drug solution was dried (1
X10 ⁵ cells / ml) is spray-inoculated into the whole pot, 20-23
℃, humidity 20% to 23 ℃ after one day in a dark place of 95% or more
Kept in a greenhouse for 7 days. Eight days after the inoculation, the degree of disease on all fruits was examined according to the following index for the area occupied by gray mold disease lesions per fruit. The results are shown in Table 4 (Tables 18 and 19). Control compounds A and B are the same as in Test Example 1.

Disease severity 0: No disease occurrence 1: Area of lesion is 5% or less 2: Area of lesion is 5 to 25% 3: Area of lesion is 25 to 50% 4: Area of lesion is 50% The average value of each treatment group and non-treatment group was defined as the disease severity. Control value (%) = (1-degree of disease in treated area / degree of disease in untreated area) × 100

[0062]

[Table 18]

[0063]

[Table 19] As shown in the above test examples, the general formula (1) of the present invention is used.
The compound represented by the formula (1) shows an excellent disease control effect against gray mold of kidney bean and strawberry, while the control compounds A and B having similar structures are considerably inferior in effect, and at low doses, almost all the effects are recognized. I couldn't do it.

[0064]

INDUSTRIAL APPLICABILITY The compound represented by the general formula (1) of the present invention exhibits an excellent disease control effect against gray mold of green beans and strawberries, and is useful as a fungicide for agriculture and horticulture.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display area A01N 43/56 A 43/58 A 43/60 43/76 43/78 B 43/80 101 102 C07D 213/40 213/61 237/08 239/26 241/12 261/08 263/32 277/28 277/32 277/56 307/52 405/12 213 231 409 409/12 213 231 307 413/12 213 231 307 333 417/12 263 307 333 (72) Inventor Nao Maeda 1144 Togo, Mobara-shi, Chiba Prefecture Mitsui Toatsu Chemical Co., Ltd. 72) Inventor Hiroyuki Katsuta 1144, Togo, Mobara-shi, Chiba Mitsui Toatsu Chemical Co., Ltd. (72) Yuji Yanase, 1144, Togo, Mobara-shi, Chiba Mitsui Toatsu Chemical Co., Ltd. 1144 Togo, Mobara-shi, Habara Mitsui Toatsu Kagaku Co., Ltd. (72) Inventor Hitoshi Shimotori 1144, Togo Mobara-shi, Chiba Mitsui Toatsu Chem. Co., Ltd. Mitsui Toatsu Chemical Co., Ltd.

Claims (3)

[Claims] 1. A heterocyclic aniline derivative represented by the general formula (1) (formula 1). [Chemical 1] [Wherein Het represents a heterocyclic group of H1 to H11 represented by the following formula (Formula 2); (In the formula, R ¹ means a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen atom or a haloalkyl group having 1 to 4 carbon atoms.) R is G1 represented by the following formula (Formula 3).
To G9 cyclic groups, (In the formula, R ² is an alkyl group having 1 to 4 carbon atoms, a halogen atom or a haloalkyl group having 1 to 4 carbon atoms, R ³ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R ⁴ is a halogen atom. Means.)]] 2. A fungicide for agricultural and horticultural use containing a heterocyclic aniline derivative represented by the general formula (1) (Chemical formula 4) as an active ingredient. [Chemical 4] [Wherein Het represents a heterocyclic group of H1 to H11 represented by the following formula (Formula 5); (In the formula, R ¹ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen atom or a haloalkyl group having 1 to 4 carbon atoms.) R represents G 1 represented by the following formula (Formula 6).
To G9 cyclic groups, (In the formula, R ² is an alkyl group having 1 to 4 carbon atoms, a halogen atom or a haloalkyl group having 1 to 4 carbon atoms, R ³ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R ⁴ is a halogen atom. Means.)]] 3. A method for controlling plant diseases, which comprises applying the heterocyclic aniline derivative represented by the general formula (1) (Formula 7) to plant pathogenic fungi or their habitat. [Chemical 7] However, Het represents a heterocyclic group of H1 to H11 represented by the following formula (Formula 8), and (In the formula, R ¹ means a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen atom or a haloalkyl group having 1 to 4 carbon atoms.) R is G1 represented by the following formula (Formula 9).
To G9 cyclic groups, (In the formula, R ² is an alkyl group having 1 to 4 carbon atoms, a halogen atom or a haloalkyl group having 1 to 4 carbon atoms, R ³ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R ⁴ is a halogen atom. Means.)