JPH02129173A - Triazole compound, its production and harmful life controlling agent containing the same - Google Patents

Abstract

NEW MATERIAL:The compound of formula I {X is carbonyl or sulfonyl; R<1> to R<3> are alkyl or cycloalkyl; R<4> is group of formula IV (Y=X; R<5> and R<6> are alkyl or H), formula V [R<7> is (substituted) pyrazyl, (substituted) pyrimidyl, etc.; m is 0 or 1], formula VI (R<8> is tert-butyl or butoxycarbonyl), etc.; excluding the case that X is carbonyl and R<4> is group of formula VII (R<9> is alkyl)} or its salt. EXAMPLE:1-Dimethylcatbamoyl-3-tert-butyl-5-dimethylcarbamoylthio-1,2,4 -1H- triazole. USE:An active component of a harmful life controlling agent. It exhibits excellent activity as an active component of insecticidal, miticidal, nematocidal and soil vermin exterminating agent and fungicide. PREPARATION:The compound of formula I can be produced by reacting a compound of formula II with a compound of formula III (Hal is halogen n) in the presence of a solvent and a base and, as necessary, a catalyst such as 4-dimethylaminopyridine.

Description

Detailed Description of the Invention (Industrial Field of Application) The present invention provides novel triazole compounds or salts thereof,
The present invention relates to methods for producing them and pest control agents containing them.

(Prior art) Triazole compounds are disclosed in, for example, JP-A-51-5152.
Publication No. 3, Publication No. 52-122625, Publication No. 62-70
No. 365, US Pat. No. 4,220,790, West German Patent Application Publication No. 3,031,191, etc. disclose that it is useful as an insecticide. However, there is no disclosure of a compound represented by the following general formula (I).

(Disclosure of the Invention) The present invention relates to the general formula (I) (wherein, X is a carbonyl group or a sulfonyl group, and R
1, R1 and R3 are each independently an alkyl group or a cycloalkyl group, R4 is a nyl group, and RS and R6 are each independently an alkyl group or a hydrogen atom)
, -+CIl tert-butyl group or tert-
butoxycarbonyl group), alkyl group having 4 or more carbon atoms, 3.6.9-) lioxadecanyl group, 2-methyl-1-propenyl group or -CIl□C0OR'1 group (
In the formula, R9 is an alkyl group. However, when X is a carbonyl group and R4 is a -C112COOR9 group, the triazole compounds represented by () or their salts, their production methods, or pest control agents containing them as active ingredients.

Since the compound of general formula (I) has an acidic or basic functional group, the salt of the triazole compound is a salt of the compound with a metal cation, an ammonium cation, or an anion, such as a salt of the compound with a metal cation, an ammonium cation, or an anion. salt, ammonium salt,
Examples include acid addition salts, which can be produced by conventional methods.

In the general formula (I), the alkyl group represented by R1, R2, R3, R5R& and R9 has 1 to 6 carbon atoms;
For example, methyl group, ethyl group, n-1so-propyl group, n-, 1so-, Lert-butyl group, n-
, 1so-, tert-pentyl group, n-1so-,
tert-hexyl group, etc., and they also include structural isomers of linear or branched aliphatic chains, and R1
, RZ and R3 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like. Among them, R3 is Le
rt-butyl group, 1so-propyl group or Ler t-
An amyl group is preferred.

Examples of the alkyl group having 4 or more carbon atoms represented by R4 include butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decanyl group, etc.; Also includes structural isomers.

The substituent for the optionally substituted pyridyl group, optionally substituted pyrazyl group, optionally substituted pyridazyl group, or optionally substituted pyrimidyl group represented by R7 is a halogen atom or a halogen atom-substituted group. Examples of good alkyl groups include halogen atoms such as fluorine, chlorine, bromine, and iodine atoms. The number of these substituents is 1 or 2 or more, and when the number of substituents is 2 or more, they may be the same or different.

The compound represented by the general formula ([) can be produced, for example, by the following method.

The reaction is carried out in the presence of a suitable catalyst. Examples of the base include tertiary amines such as triethylamine and pyridine; examples of the solvent include ethers such as tetrahydrofuran and dioxane; and examples of the catalyst include 4-dimethylaminopyridine and ■,8-diazabicycloundecene. Examples include.

The reaction temperature is usually 0 to 100°C, preferably 60 to 80°C.
The reaction time is usually 0.5 to 24 hours, preferably 2 to 12 hours.

The compound represented by the above general formula (If) can be produced, for example, by the following method.

Manufacturing method (A): (IT) (Ilal is a halogen atom, R1,, RZ,
R3R4 and and 1lal is a halogen atom) In the above manufacturing method (A), the general formula (II
The compound represented by I) is generally known or can be produced by a known method such as the above production method (A), but specifically, for example, JP-A-62-70365
It can be produced by the method described in (a) of [Production method 2] on page 33 of , or according to the method described therein.

The above production method (B) is usually carried out in the presence of a base and a solvent, and examples of the base include alkali metals such as sodium and potassium; alkali metal hydrides such as sodium hydride and potassium hydride; Examples include alkali metal hydroxides such as sodium and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; organic bases such as triethylamine, pyridine, and 1,8-diazabicycloundecene. , solvents include aprotic polar solvents such as dimethylformamide and hexamethylphosphoric triamide; ether necks such as tetrahydrofuran and dioxane; methyl alcohol,
Alcohol necks such as ethyl alcohol; methyl acetate,
Examples include esters such as ethyl acetate. The reaction temperature is usually 0 to 150°C, preferably 60 to 150°C.
and the reaction time is usually 0.5 to 24 hours, preferably 2
~10 hours.

Next, a specific example of synthesis of the compound of the present invention will be described.

Synthesis Example 1 1-dimethylcarbamoyl-3-Lert-butyl-5
Synthesis of -dimethylcarbamoylthio-1,2,4-I H-triazole (compound 3) a) 50 g (0.55 mol) of thiosemicarbazide and 200 mj! A suspension of 10% in tetrahydrofuran
After cooling to °C, 69.4 g (0,
57 mol) of trimethylacetyl chloride and a further 58.3 g (0.57 mol) of triethylamine. The mixture was stirred at room temperature for 1 hour and then heated to reflux for 1 hour, and 150 m/ml of tetrahydrofuran was removed by distillation. Furthermore, 150 ml of water and 92.2 g (I, 15
A 50% aqueous solution of sodium hydroxide (mol) was added and distillation of tetrahydrofuran and triethylamine was continued until the reaction mixture reached 80° C. The reaction mixture was heated under reflux for an additional 3 hours and then cooled to room temperature. reaction mixture to 100
After washing with 1 ml of ethyl acetate, the ethyl acetate layer was removed and 400 g of ice and 100 ml of concentrated aqueous hydrochloric acid were added to the residue, resulting in a white solid precipitate. The solid was filtered, washed with hexane, water, then hexane and dried in air to give 3-tart-butyl-5-mercapto-1,2,4-I H-1-lyazole as a white solid with a melting point of 195-198°C. 74g was obtained.

b) 1.4 g in a solution of 2 g (0,013 mol) of 3-tert-butyl-5-mercapto-1,2,4-I H-triazole and 15 ml of ethyl acetate
(0,013 mol) of N,N-dimethylcarbamoyl chloride and 1.3 g (0,013 mol) of triethylamine were added and heated at reflux for 5 h. The reaction mixture was cooled to room temperature and diluted with 50 ml of water. It was washed and the aqueous and oil layers were separated. The aqueous layer was extracted with 50 m/ml of ethyl acetate before being discarded, and the oil layer was combined with this ethyl acetate extract and
Qm7! The mixture was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The product was recrystallized from hexane to give a 3-ter
t-Butyl-5-dimethylcarbamoylthio-1,2,
4-I 11-triazole as white crystals 2.2
I got g.

c) 3 ter of 2 g (0,0087 mol)
t-Butyl-5-dimethylcarbamoylthio-L2,4
-IH-triazole and 1.1 g (0,0102 mol) of N,N-dimethylcarbamoyl chloride in a solution of 15 ml of tetrahydrofuran.
(0,0108 mol) of triethylamine and 0.1
g (0,0008 mol) of 4-dimethylaminopyridine was added and heated under reflux for 2 hours. The reaction mixture was cooled to room temperature, washed with 50 ml of water, and the aqueous and oil layers were separated.

The aqueous layer was extracted with 50 ml of ethyl acetate before being discarded, and the oil layer was combined with this ethyl acetate extract and washed with 50 ml of saturated brine, then dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. Distilled away. The product was purified by silica gel column chromatography with a melting point of 104-108°C.
Target compound (compound m3) ('■-NMR (CDC'f
i) δ: 1.39 (s, 911), 3.03 (
1.5 g of a+, 1211) ) was obtained as white crystals.

Synthesis example 2 1-dimethylcarbamoyl-3tert-butyl-5-
Synthesis of dimethylsulfamoylthio-1,2,4-IH-triazole (compound 4) a) Synthesis example 1 (a)
) 3g (0,019 mol) of 3-
tart-butyl-5-mercapto-1,2,4-I
3 g (0,0209 mol) of dimethylsulfamoyl chloride and 2 g (0,0197 mol) of triethylamine were added to a solution consisting of H-triazole and 15 ml of ethyl acetate, and the mixture was heated under reflux for 10 hours. Thereafter, it was treated in the same manner as in Synthesis Example 1(b) above, and the melting point was 193-195°C.
3.8 g of 3-tert-butyl-5-dimethylsulfamoylthio-1,2,4-I H-)riazole was obtained.

b) 1 g (0,0043 mol) of 3-tert
-butyl-5-dimethylsulfamoylthio-1,2,
0.5 g (0,0
046 mol) of dimethylcarbamoyl chloride, 1
g (0,0098 mol) of triethylamine and 0
．． 2 g (0,0016 mol) of 4-dimethylaminopyridine was added, and the mixture was heated under reflux for 10 hours. Thereafter, post-treatment and purification were carried out in the same manner as in Synthesis Example 1(C), and the melting point was 1.
Target product (compound number 4) at 28-129°C ('II-
NMR (CDCI!3) δ: 1.39 (s, 91
1), 3.06 (m, 1211) ) was obtained as white crystals in an amount of 1 g.

Synthesis Example 3 1-dimethylcarbamoyl-3-tert-phthyl-5- (2-pyridylmethylthio) -1,24-I
Synthesis of H-triazole (compound 1'& t5) a)
3g obtained in the same manner as in Synthesis Example 1(a) of rriI
(0,019 mol) of 3-tert-butyl-5-mercapto-1,2,4-I H-1-lyazole and 30 m
3.3 g (0.02
mol) of 2-pyridylmethyl chloride hydrochloride and 4.0
g (0.04 mol) of triethylamine was added and heated under reflux for 4 hours. Thereafter, after post-treatment in the same manner as in Synthesis Example 1(b), the 3-tert-
Butyl-5-(2-pyridylmethylthio)-1,2,
4.7 g of 4-I H-) riazole was obtained as white crystals.

b) 1 g (0,004 mol) of 3-tart-
Butyl 5-(2-pyridylmethylthio)-1,2,4
-I H-triazole and 15mj! of tetrahydrofuran and 0.6 g (0,0056 mol) of dimethylcarbamoyl chloride, 1 g (0
,0099 mol) of triethylamine and 0.2 g
(0,0016 mol) of 4-dimethylaminopyridine was added and refluxed for 4 hours. The formula (II) is almost new, and it is thought that the following three types of tautomers exist.

■ (■' ) (■#) (■#) A typical example thereof is expressed as the general formula (■') and is listed in Table 1 below.

NMR (CDC13) δ: 1.03 (s, 911
), 3.10 (s, 611).

4.56 (s+211), 7.0-7.3 (m, 111
), 7.5-7.8 (m, 211).

8.5-8.66 (m, IH)) was obtained as an oily substance in an amount of 1.4 g.

Next, regarding the intermediate of the compound of the present invention, since the compound of the general formula (n) has three types of tautomers as described above, the above-mentioned production method using the intermediate as a raw material can produce the intermediate. Isomers of the following general formula may exist in the product.

Next, representative examples of the compounds of the present invention are listed in Table 2, represented by the general formula (I').

The structures of the target compounds represented by the general formula (do) in Table 2 above or named in Synthesis Examples 1 to 3 above are considered to be correct for these compounds, respectively. There is a possibility that an isomer compound represented by the corresponding general formula (I"): (R', R" where SR3 and R' are <7) as described above) is mixed.

The compound of the present invention exhibits a control effect against pests, and exhibits excellent activity as an active ingredient of insecticides, acaricides, nematicides, soil insecticides, and fungicides, for example. For example, plant parasitic mites such as two-spotted spider mite, false red spider mite, citrus spider mite, red mite, etc., diamondback moth, armyworm, fall armyworm, codling moth, ballworm, tobacco budworm, gypsy moth, Colorado potato beetle, cucurbit beetle, ballweevil, aphids, planthopper. species, leafhoppers, scale insects, stink bugs, white larvae, thrips, grasshoppers, wasp flies, scarabs, scarab beetles,
Agricultural pests such as cabbage moth, onion fly, ants, sanitary pests such as house dust mite, cockroach, house fly, Culex mosquito, grain storage pest such as dust moth, adzuki bean weevil, brown beetle, mealworm neck, etc.
It is also effective against clothing, house pests such as burrs, termites, fleas, lice, flies, etc. that parasitize livestock, and it is also effective against cat nematodes, cyst nematodes, and insects. It is also effective against plant-parasitic mites such as nematodes, rice nematodes, strawberry nematodes, and pine nematodes.

It is also effective against soil pests. Soil pests mentioned here include gastropods such as slugs and snails,
Examples include isopods such as pill bugs and woodlice. Furthermore, it is effective against insect pests such as dicofol (trade name: Takeda Pharmaceutical Co., Ltd.) and plant parasitic mites that are resistant to organic phosphorus agents, aphids that are resistant to organic phosphorus agents, and house flies.

The compounds of the present invention can also be used to treat rice blast, rice sheath blight, cucumber anthracnose, cucumber powdery mildew, cucumber downy mildew, tomato late blight, tomato ring spot, citrus black spot, citrus green mold, and pear black spot. Diseases such as apple leaf spot leaf rot, grape downy mildew, various types of gray mold, sclerotinia, and rust, and plant pathogenic bacteria such as Fusarium, Bicillum, Rhizoctonia, Particium, and Plasmodiophora. It also shows excellent control effects against soil diseases caused by the plant.

The compound of the present invention exhibits particularly excellent control effects against two-spotted spider mites, red-spotted spider mites, orange spider mites, powdery mildew, and downy mildew among the above-mentioned pests.

When using the compound of the present invention as an active ingredient of a pest control agent, it can be used in emulsions, powders, granules, wettable powders, liquids, aerosols, and pastes together with pesticide adjuvants, as in the case of conventional m-drug formulations. It can be formulated into various forms such as , suspension, etc. The ratio of these ingredients is usually 0.5 of the active ingredient.
~90 parts by weight and 10 to 99.5 parts by weight of agricultural chemical adjuvant. When these preparations are actually used, they can be used as they are, or they can be diluted to a predetermined concentration with a diluent such as water.

The agrochemical auxiliary agents mentioned herein include carriers, emulsifiers, suspending agents, dispersants, spreading agents, penetrants, wetting agents, thickeners, stabilizers, etc., and may be added as appropriate if necessary. Carriers are divided into solid carriers and liquid carriers, and solid carriers include starch, activated carbon, soybean flour, wheat flour, wood flour, fish meal, animal and vegetable powders such as milk powder, talc, kaolin, bentonite, calcium carbonate, zeolite, Examples include mineral powders such as diatomaceous earth, white carbon, clay, alumina, and sulfur powder. Liquid carriers include water, alcohols such as methyl alcohol and ethylene glycol, ketones such as acetone and methyl ethyl ketone, dioxane,
Ethers such as tetrahydrofuran, aliphatic hydrocarbons such as kerosene and kerosene, aromatic hydrocarbons such as xylene, trimethylbenzene, tetramethylbenzene, cyclohexane and solvent naphtha, halogenated hydrocarbons such as chloroform and chlorobenzene, dimethyl Examples include acid amides such as formamide, esters such as ethyl acetate and glycerin ester of fatty acids, nitrites such as acetonitrile, and sulfide-containing metals such as dimethyl sulfoxide.

In addition, other agricultural chemicals such as insecticides, acaricides, nematicides, fungicides, antiviral agents, attractants, herbicides,
It can be mixed or used in combination with plant growth regulators, etc., and may exhibit even better effects in this case.

For example, as an insecticide, acaricide, or nematocide
-(4-bromo-2-chlorophenyl)0-ethyl S-
Propyl phosphorothioate, 212 dichlorovinyl dimethyl phosphate, ethyl 3-methyl-4-(methylthio)phenylisopropyl phosphoramidate, 0.
O-dimethyl〇-4-nitro m-1-lyl phosphorothioate, 0-ethyl 0-4-nitrophenylphosphonothioate, 0.0-diethyl 0-2-isopropyl-6
Methylpyrimidin-4-ylphosphorothioate, 0.
0-dimethyl O-(3,5,6-dolychloro-2-pyridyl) phosphorothioate, ols-dimethylacetylphosphoramidothioate, 0-(2,4=dichlorophenyl)0-ethyl S-propylphosphorodithioate Organic phosphate ester compounds such as: l-naphthyl methyl carbamate, 2-isopropoxyphenyl methyl carbamate, 2-methyl-2-(methylthio)propionaldehyde O-methylcarbamoyl oxime,
2.3-dihydro-2,2-dimethylbenzofuran-7
-ylmethyl carbamate, dimethyl N, N'-(thiobis[(methylimino)carbonyloxy]]bisethanimidothioate, S-methyl N-(methylcarbamoyloxy)thioacetoimizo-), N,N-dimethyl-2- Methylcarbamoyloxyimino-2-(methylthio)acetamide, 2-(ethylthiomethyl)phenylmethylcarbamate, 2-dimethylamino-5,6
- Carbamate compounds such as dimethylpyrimidin-4-yldimethylcarbamate, S, 5t-2-dimethylaminotrimethylenebis(thiocarbamate);2.
2.2-) LichloroLl-bis(4-chlorophenyl)ethanol, 4-chlorophenyl-2,4,5-
Organochlorine compounds such as trichlorophenylsulfone; organometallic compounds such as tricyclohexyltine hydroxide; (R5) -αcyano-3-phenoxybenzyl (RS)-1-(4-chlorophenyl)-
3-methylbutyrate, 3-phenoxybenzyl (IR
5)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 1
-1(R5) -α-cyano-3-phenoxybenzyl(I115)-cis.

trans-3-(2,2-dichlorovinyl)-2,2
=dimethylcyclopropane hydroxylate, (S)-
α-cyano-3-phenoxybenzyl(IR)-cis-
3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate, (R3)-α-cyano-3-phenoxybenzyl (IR3)-cis, trans-3-(2-chloro-3, 3,3-)lifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate, 4-methyl-2,3,5,6-tetrafluorobenzyl-3-(2-chloro-3,3,3-tri Pyrethroid compounds such as fluoro-1-propen-1-yl)-2,2-dimethylcyclopropanecarboxylic acid; 1
-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea, 1-(3,5-dichloro-4-
(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl)-3-(2,6-difluorobenzoyl)urea, 1-(3,5-dichloro-2,4-
benzoylurea compounds such as difluorophenyl)-3-(2,6-difluorobenzoyl)urea; 2
-tert-butylimino-3-isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H-1,3
,5-thiadiazin-4-one, trans-(4-chlorophenyl)-N-cyclhexyl-4-methyl-2-
Compounds such as oxothiapridinone-3-carboxamide, N-methylbis(2,4-xylyliminomethyl)amine; isopropyl(2H,4E)-11-methoxy-3,7,11-)dimethyl-2, Juvenile hormone-like compounds such as 4-dodecagenoate; other compounds include dinitro compounds, organic sulfur compounds,
Examples include urea compounds and triazine compounds.

Furthermore, it can be mixed or used in combination with microbial pesticides such as BT agents and insect pathogenic virus agents.

For example, as a fungicide, an organic phosphorus compound such as S-benzyl O1O diisopropyl phosphorothioate, 0-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate;
Organochlorine compounds such as 4,5.6.7-tetrachlorophthalide and tetrachloroisophthalonitrile; polymers of Manganese ethylene bis(dithiocarbamate);
Zinc ethylene bis(dithiocarbamate) polymer,
A dithiocarbamate-based compound such as a complex compound of zinc and maneb, a polymer of didizinc bis(dimethyldithiocarbamate), ethylene bis(dithiocarbamate), and zinc propylene bis(dithiocarbamate); 3a,
4.7,7a-tetrahydro-N-(trichloromethanesulfenyl)phthalimide, 3a,4.7.7a-tetrahydro-N-(LL2+2-tetrachloroethanesulfenyl)phthalimide, N-(trichloromethylsulfenyl)phthalimide N-halogenothioalkyl compounds such as: 3-(3,5-dichlorophenyl)-
N-isopropyl-2,4-dioxoimidazolidine-
1-carboxamide, (R5) -3-(3,5-dichlorophenyl)-5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione, N-(3,5-dichlorophenyl)-1, 2-dimethylcyclopropane-1,
Dicarboximide compounds such as 2-dicarboximide; methyl 1-(butylcarbamoyl)benzimidazole-2-ylbamate, dimethyl 4.4'-(0-
Benzimidazole compounds such as phenylene)bis(3-thioallophanate); 1-(4-chlorophenoxy)-3,3-dimethyl-1-(I H-1,2,4
-triazol-1yl)butanone, 1-(biphenyyl-4-yloxy) -3,3-dimethyl-1-(
I H-1,2,4-triazol-1-yl)butan-2-ol, 1-(N-(4-chloro-2-trifluoromethylphenyl)-2-propoxyacetimidoylcoimidazole, l- (2-(,2,4-dichlorophenyl)-4-ethyl-1,3-dioxolane-2
-ylmethyl) -111-1,2,4-1-riazole, 1- (2-(2,4-dichlorophenyl)-4-
Propyl-1,3-dioxolan-2-ylmethyl]I
H-1,2,4-triazole, 1-(2-(2,4
=dichlorophenyl)pentyl) -1ll-1,2,
Azole compounds such as 4-triazole; 2,4'
Dichloro-α-(pyrimidin-5-yl)benzhydryl alcohol, (±)-2,4'-difluoro-α-(
I H-Carbinol compounds such as 1,2,4-1-riazol-1-ylmethyl)benzhydryl alcohol; 3'-isopropoxy-0 trianilide, α, α
, benzanilide compounds such as α-trifluoro-3′-isopropoxy-0-trianilide; methyl N-
(2-methoxyacetyl)-N-(2,6-xylyl)
phenylamide compounds such as -DL-alaninate; Pyridinamine compounds such as; other compounds include piperazine compounds, morpholine compounds, anthraquinone compounds,
Examples include quinoxaline compounds, crotonic acid compounds, sulfenic acid compounds, urea compounds, and antibiotics.

The pest control agent of the present invention is effective in controlling various harmful insects, harmful mites, harmful nematodes, harmful soil pests, etc., and the application is generally from 1 to 20. The concentration of the active ingredient is OOOppm, preferably 20 to 2.000 ppm. The concentration of these active ingredients can be appropriately changed depending on the form of the preparation, the method of application, purpose, timing, location, pest outbreak status, etc. For example, in the case of harmful aquatic insects, the concentration range of the active ingredient in water is below the above range, since it can be controlled by spraying a chemical solution with the above concentration range to the place where the pest occurs. The application amount per unit area is approximately 0.0.0% as the active ingredient compound per 10a.
1-5,000 g, preferably 10-1,000 g
is used. However, in special cases it is also possible to depart from these ranges.

Various formulations containing the compound of the present invention or dilutions thereof can be applied by commonly used application methods, namely:
11 Female cloth (e.g. scattering, spraying, misting, atomizing, dusting, water surface application, etc.), soil application (mixing, irrigation, etc.), tree irrigation, surface application (coating, dusting, covering, etc.), dipping poison bait method This can be done by, for example, It can also be applied by a so-called ultra high concentration small volume spraying method. In this way, 100% active ingredient content is possible.

■ Disperse each formulation of the active ingredient compound for the green peach bug in water, and
It was adjusted to 00 ppm.

4-5 cups (diameter 7 cni, height 4C11) planted
Only the third or fourth leaves of the eggplant leaves were left, and an adhesive (Fujitan gel) was applied to the petioles, and two adult green peach aphids were released on the eggplant leaves.

After spawning larvae for 2 days, the adults were removed, and together with the eggplant leaves, they were immersed in the chemical solution adjusted to the predetermined concentration for about 10 seconds, air-dried, and then left in a constant temperature room with lighting at 26°C. Five days after the treatment, survival was determined and the survival rate was calculated using the following formula. Compounds Nos. 1 to 16 showed a survival rate of 90% or more. In addition, insects that detached from the eggplant leaves were also considered to be dead.

Each formulation of active ingredient compound was dispersed in water and adjusted to a predetermined concentration.

Power/knob (diameter 7 cm, height 4 cIl) 4-5 plants
Only the third or fourth leaf from the eggplant leaf stage was left, and an adhesive (Fujitan gel) was applied to the petiole. 800ppm
The soil was irrigated with chemical solution 10II11 and left in a constant temperature room with lighting at 26°C. Two days after the treatment, 10 green peach aphid larvae were grown into adults, and five days after the adults became adults, the survival rate was determined in the same manner as in Test Example 1 above. In addition, insects that detached from the eggplant leaves were also considered to be dead.

As a result, Compounds 3 to 6 showed a 100% mortality rate.

3. Disperse each formulation of the active ingredient compound in water, and
Rice seedlings were immersed in the chemical solution adjusted to 0.00 ppm for 10 seconds, air-dried, the roots were wrapped with absorbent cotton, and the seedlings were placed in a test tube.

Next, we released 10 larvae of the brown planthopper into this.
The tube opening was covered with gauze. After 5 days, the insects were determined to be alive or dead, and the survival rate was determined in the same manner as in Test Example 1. As a result, compounds Nl13-6.8.10 and 12-16 are 1
The mortality rate was 0.00%.

Next, test examples of the compound of the present invention as an agricultural and horticultural fungicide will be described.

The evaluation in the test example was based on the following criteria.

Evaluation: The control effect on pest control was determined by visually observing the degree of disease on the test plants at the time of the survey, and determining the control index using the following five levels.

C control index] [Severity of disease onset] 5: No lesions observed 4: Lesion area, number of lesions, or lesion length is less than 10% of the untreated area 3: Lesion area, number of lesions, or disease Spot length is less than 40% of the untreated area2: The lesion area, number of lesions, or lesion length is less than 70% of the untreated area1: The lesion area, number of lesions, or lesion length is less than the untreated area 70% or more of the area 4 Cucumber 1 Cucumber in a plastic pot with a diameter of 7.5 cm (Variety: Four-leaf)
Cultivate a crane and when it reaches the two-leaf stage, add 500 compounds of Compound 1.
10 ml of a chemical solution adjusted to ppm was sprayed using a spray gun. After keeping it in a constant temperature room at 22-24℃ for 1 day and night,
A spore suspension of Bacillus anthracis was inoculated by spraying. Seven days after inoculation, the area of lesions on the first leaf was investigated and the control index was determined according to the above evaluation criteria, which showed a control index of 5.

5. Cucumber in a plastic pot with a diameter of 7.5 cm
was cultivated, and when it reached the two-leaf stage, 500% of each test compound was added.
Chemical solution 101111 adjusted to a concentration of ppm was sprayed using a spray gun. After being kept in a thermostatic chamber at 22 to 24° C. for one day and night, a spore suspension of downy mildew was inoculated by spraying. Six days after inoculation, the lesion area on the first leaf was investigated and the control index was determined according to the above evaluation criteria. Compounds 6 and 10 showed a control index of 4.

6 Oats (variety: Shingen) were cultivated in plastic pots with a diameter of 7.5 cm, and when they reached the two-leaf stage, 500p of each test compound was added.
10 ml of a chemical solution adjusted to a concentration of pm was sprayed using a spray gun. After keeping it in a thermostatic chamber at 22 to 24°C for one day, it was inoculated by sprinkling conidia of the crown rust fungus. Inoculation 1
After 0 days, the area of the lesion on the second leaf was investigated and the control index was determined according to the above evaluation criteria. Compound pigeons 5 and 6 showed a control index of 4.

Formulation Example 1 (a) Compound 11h3 20 parts by weight (1) N,N'-dimethylformamide 32 parts by weight (c) Xylene 40 parts by weight (d) Polyoxyethylene alkyl phenyl ether
8 parts by weight or more are uniformly mixed and dissolved to form an emulsion.

Formulation Example 2 (a) Compound 5 5 parts by weight (b) Bentonite 45 parts by weight (c) Kaolin
50 parts by weight or more is kneaded with a small amount of water, extruded into granules, and dried to form granules.

Formulation Example 3 (a) Compound PkL6 30 parts by weight (b)
Fine powder silica 35 parts by weight (c) Fine powder clay 25 parts by weight (d) Naphthalene sulfonic acid soda formalin condensate 2 parts (e) Dialkyl sulfosuccinate 3 parts by weight (f) Polyoxyethylene alkylaryl (aryl) ether sulfate 5 parts by weight or more are uniformly ground and mixed to form a wettable powder.

Formulation Example 4 (a) Compound 8 1 part heavy oil (b) 99 parts by weight or more of talc are uniformly mixed to form granules.

Formulation Example 5 (a) Compound 4 50 parts by weight (b) Methyl cellosolve 30 parts heavy oil (c) Polyoxyethylene alkyl phenyl ether
A liquid preparation is prepared by uniformly mixing and dissolving 20 parts by weight or more.

Claims (1)

[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) (In the formula, X is a carbonyl group or a sulfonyl group, and R
^1, R^2 and R^3 are each independently an alkyl group or a cycloalkyl group, and R^4 is ▲ mathematical formula, chemical formula,
There are tables, etc. ▼ groups (in the formula, Y is a carbonyl group or sulfonyl group, and R^5 and R^6 are each independently an alkyl group or a hydrogen atom), ▲ mathematical formulas, chemical formulas, tables, etc. ▼ Group (wherein R^7 is an optionally substituted pyridyl group, an optionally substituted pyrazyl group, an optionally substituted pyridazyl group, or an optionally substituted pyrimidyl group, and m is 0 or 1) ), ▲Mathematical formulas, chemical formulas, tables, etc.▼ groups (R^8 is tert-butyl group or tert-butoxycarbonyl group), alkyl groups with 4 or more carbon atoms,
3,6,9-trioxadecanyl group, 2-methyl-1-
propenyl group or -CH_2COOR^9 group (in the formula R^
9 is an alkyl group). (However, this excludes the case where X is a carbonyl group and R^4 is a -CH_2COOR^9 group) or a salt thereof. 2. General formula (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼... (II) {In the formula, R^3 is an alkyl group or cycloalkyl group, and R^4 is ▲ Numerical formula, chemical formula, There are tables etc. ▼ group (
In the formula, Y is a carbonyl group or a sulfonyl group, and R^
5 and R^6 are each independently an alkyl group or a hydrogen atom), ▲ Numerical formula, chemical formula, table, etc. ▼ group (In the formula, R^7 is an optionally substituted pyridyl group, a good pyrazyl group, an optionally substituted pyridazyl group, or an optionally substituted pyrimidyl group, m is 0 or 1), ▲ mathematical formula, chemical formula, table, etc. ▼ group (R^6 is tert-butyl group or tert-butoxycarbonyl group), alkyl group having 4 or more carbon atoms, 3,6,9-
Trioxadecanyl group, 2-methyl-1-propenyl group, or -CH_2OOR^9 group (in the formula, R^9 is an alkyl group)} and the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, X is a carbonyl group or a sulfonyl group, and R
^1 and R^2 are each independently an alkyl group or a cycloalkyl group). General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼... (I) (In the formula, X, R^1, R^2, R^3 and R^4 are as mentioned above, but , except when X is a carbonyl group and R^4 is -CH_2OOR^9 group) or a method for producing a triazole compound or a salt thereof. 3. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼... (I) {In the formula, X is a carbonyl group or a sulfonyl group, and R
^1, R^2 and R^3 are each independently an alkyl group or a cycloalkyl group, and R^4 is a ▲mathematical formula, chemical formula, table, etc.▼ group (in the formula, Y is a carbonyl group or a sulfonyl group) group, R^5 and R^6 are each independently an alkyl group or a hydrogen atom), ▲ mathematical formula, chemical formula, table, etc. ▼ group (in the formula, R^7 is optionally substituted pyridyl group, optionally substituted pyrazyl group, optionally substituted pyridazyl group, or optionally substituted pyrimidyl group, where m is 0 or 1), ▲ mathematical formula, chemical formula, table, etc. ▼ group (R ^6 is a tert-butyl group or a tert-butoxycarbonyl group), an alkyl group having 4 or more carbon atoms,
3,6,9-trioxadecanyl group, 2-methyl-1-
propenyl group or -CH_2COOR^9 group (in the formula R^
9 is an alkyl group). A pest control agent characterized by containing a triazole compound or a salt thereof as an active ingredient, except when X is a carbonyl group and R^4 is a -CH_2COOR^9 group.