JPS62169766A - Pyridines and pesticide containing same - Google Patents

Abstract

NEW MATERIAL:A pyridine of formula I [X is halogen, trifluoromethyl, nitro; Y is H, amino which may substituted with halogen, phenyl which may be substituted, pyridyl which may be substituted; Z is carbonyl thiocarbonyl, formula II, formula III (Q, Q2 are O, S, -NH-; R1, R2 are H, alkyl); n is integer of 0-2]. EXAMPLE:3-[2-(2,4-Dichloro-alpha-methylenebenzyl)-1,3-dioxolan-2-yl-]p yridine. USE:An agent for controlling pests. PREPARATION:For example, the reaction of a compound of formula IV (Z1 is carbonyl, thiocarbonyl) with another compound of formula V is carried out in an organic solvent in the presence of an acid catalyst to give a compound of formula I where Z is formula II and formula III.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to -pyridine compounds and pest control agents containing them.

(Disclosure of the Invention) The compound of the present invention has the general formula (■): [In the formula, X is a halogen atom, a trifluoromethyl group, or a nitro group, and Y is a hydrogen atom; It is a pyridine compound represented by (1 alkyl group; may be substituted with an alkyl group, 7 amino groups; substituted, n is an integer from O to 2).

In the general formula (I), the denene atom represented by X and the halogen atom substituted with a halogen atom (in one alkyl group) include a chlorine atom, a bromine atom, a fluorine atom; , an iodine atom, and a fluorine atom is more desirable as a halogen atom of an alkyl group even if it is substituted with a gen atom represented by Y. Also, the alkyl group similarly represented by Y and the alkyl group of Ami 7 which may be substituted with an alkyl group, and R15R2, R1,
The alkyl group and alkyl moiety of the alkoxyalkyl group represented by and R4 include methyl, ethyl, propyl, butyl, etc., and an alkyl group having 1 to 6 carbon atoms is preferable. Furthermore, the substituents for the optionally substituted phenyl group and the optionally substituted pyridyl group represented by Y include a chlorine atom, a bromine atom, a fluorine atom, an iodine atom, a trifluoromethyl group, a nitro group, a cyano group. (■)
1-60 o'clock r", n <■>
The acid catalyst used in the above reaction is particularly a mineral acid such as sulfuric acid, hydrochloric acid, sulfonic acid, etc. - Toluenesulfonic acid, methanesulfonic acid, etc. are mentioned, and solvents include acetone, methanol, ethanol, n-butanol, tetrahydro7rane, benzene, toluene, dimethylformamide, dimethylsulforide, etc., and these are mixed. The reaction temperature is 50-180℃.
℃, preferably 80 to 120℃. When carrying out this reaction, it is preferable to carry out the reaction while removing water by-produced during the reaction from the reaction system, since the reaction often proceeds smoothly.

Some of the compounds of the present invention have asymmetric carbon atoms, and these compounds can be obtained in the form of a mixture of optical isomers, but this mixture can be separated into each isomer by known methods such as chromatography. You can also do it.

Among the compounds represented by the general formula (II), when Zl is a carbonyl group, it can be easily produced by reacting a known pyridyl ketone with an aldehyde or an aldehyde derivative; Among the compounds represented by the general formula (II), when Zl is a thiocarbonyl group, the compound represented by the general formula (II) in which Zl is a carbonyl group and a sulfurizing reagent, such as phosphorus pentasulfide or Lawson's reagent 1. (Lau+esson reagent) by a known method.

Next, a specific synthesis example will be described.

Synthesis Example 1 Synthesis of 3-[2-(2,4-dichloro-α-methylenebenzyl)-1゜3-dioxolane-2-ylcopyridine (Compound No. 7) N) 2.4-dichloropenecury 3-pyridyl 2.66 g of ketone was dissolved in 5 ml of total acetic anhydride, and N,N,N',N'-tetramethylnoaminomethane was added dropwise while stirring and cooling to keep the temperature of the reaction mixture below 40'C. After the dropwise addition, the mixture was reacted at room temperature for 2 hours with stirring.

After the reaction, the solvent was distilled off under reduced pressure and 2
-(2,4,-dichlorophenyl)-1,-(3-pyridyl)-2-7'lopen-1-one (compound Nol) 2
I got g.

[2] 2-(2,4-dichlorophenyl)-1-(3-pyridyl)-2-propene-1 obtained in the above step [1]
-on 1.31. g, ethylene glycol 0.55g
and P-) 1.25 g of luenesulfonic acid monohydrate was dissolved in 20 ml of toluene and reacted under heating under reflux for 38 hours.

After the reaction was completed, the solvent was distilled off under reduced pressure, and the residue was dissolved in methylene chloride, washed with an 8% aqueous sodium hydroxide solution, and then washed with water. After washing with water, the residue was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.15 g of the desired product with a refractive index (,60·2) of 1.5604.

Example 2 Synthesis of 3-(2-(2,4-dichloro-α-methylenebenzyl)-4,5-:)methyl-1,3-dioxolan-2-ylcopyridine (Compound No. 10) Synthesis Example 1 2-(2,4-dichlorophenyl)-1-(3-pyrinol)-2-propene-1 obtained in step [1]
-On 1. ．． 5g -,2,,3-butanol 0.
9g and p-) luenesulfonic acid monohydrate 1.44Fi
2,3-
Butanediol 1.8g and P-)luenesulfonic acid 1
2.8 g of hydrate was added and the reaction was further continued for 24 hours.

After the reaction was completed, the solvent was distilled off under reduced pressure, and the residue was dissolved in methylene chloride, washed with an 8% aqueous sodium hydroxide solution, and then washed with water.

After washing with water, drying with 17 um of anhydrous sulfuric acid, distilling off the solvent under reduced pressure, and purifying with silica gel column chromatography, the desired product with a refractive index (n6s・2) of 1.5448 was obtained.
5gt! -I got it.

Synthesis Example 3 3-[:2-(1,2-bis(2,4-dichlorophenyl)vinyl)-1,,3-dioxolane-2
-Synthesis of Ilkopyridine (Compound No. 8) H) 1.33 g of 2,4-dichlorobenno-3-pyridyl ketone and 0 2,4-dichlorobenzaldehyde
．． 88 g was dissolved in 10 ml of toluene, 1 drop of piperidine and 2 drops of acetic acid were added with stirring, and the mixture was reacted under heating under reflux for 14 hours.

After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was dissolved in methylene chloride, then washed with water, dried over 17 um of anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography. Refractive index (n3') 1.5504
2,3-bis(2,4-dichlorophenyl)-1-(
3-pyridyl)-2-propen-1-one (compound N
o,5) 2.0g was obtained.

[2] 2,3-bis(2,4-
dichlorophenyl)-1-(3-pyrinol)-2-propen-1-one 1 g 1 ethylene glycol 0,3. and P-) luenesulfonic acid monohydrate 0. [37gwo) Ruen 20m! After 15 hours, 0.3 g of ethylene glycol and 0.67 g of r-)toluenesulfonic acid monohydrate were added, and the reaction was further continued for 9 hours.

After the reaction is complete, the reaction mixture is cooled and the solvent is distilled off under reduced pressure.
The residue was dissolved in methylene chloride and washed with 8% aqueous sodium hydroxide solution and then with water. After washing with water, drying with anhydrous sodium sulfate, distilling off the solvent under reduced pressure, and purifying with silica gel column chromatography.
) 0.3 g of the target product of 1.4945 was obtained.

Synthesis Example 4 2-(2,4-dichlorophenyl)-1-(
3-pyridyl)-2-buten-1-one (compound No.
2) Synthesis [1] 2.4-dichlorobenzyl-3
- 2.66 g of pyrinorketone and N,N-trimethylformamide were reacted under heating under reflux.

After the reaction is complete, excess acetal is distilled off under pressure and purified by silica gel column chromatography to obtain a solution with a melting point of 145~
2-(2.4.-dichlorophenyl l 3 at 151 °C
2.5 g of -(dimethylamino)-1-(3-pyridyl)-2-propen-1-one (Compound No. 4) was obtained.

[2] Dissolve 2 g of 2-(2.4-dichlorophenyl)-3-(dimethylamiz)l-(3-pyrinol)-2-propen-1-one obtained in step [1] in 30 ml of tetrahydrofuran. The mixture was cooled to −20° C., and 9.5 ml of a tetrahydrofuran solution containing 1.13 g of methylmagnesium bromide was added dropwise. After the dropwise addition, the mixture was reacted at -20°C for 1 hour, then returned to room temperature, and further reacted for 3 hours.

After the reaction is complete, the product is poured into water and the mixture is diluted with hydrochloric acid.
(2) The temperature was adjusted to 8 and extracted with methylene chloride. Next, the extracted layer was washed with water, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography to obtain the target product with a refractive index (n6a・2) of 1.4906.
55g was obtained.

Synthesis Example 5 2-(2.4-dichlorophenyl)-1
Synthesis of -(3-pyridyl)-2-penten-1-one (Compound No. 3) 2 obtained in step [1] of Synthesis Example 4
-(2,'4-dichlorophenyl)-3-(dimethylamino)-1. -(3-Pyridyl)-2-proben-toone (2 g) was dissolved in 30 ml of tetrahydrofuran, -2
Cool to 0°C and add 0.0% ethylmagnesium chloride.
941? 5.3 ml of tetrahydro7 run solution containing
was dripped. After the dropwise addition, the mixture was reacted for 1 hour at -20°C, then returned to room temperature, and further reacted for 3 hours.

After the reaction is complete, the product is poured into water and the mixture is purified with hydrochloric acid.
118 and extracted with methylene chloride. Next, the extracted layer was washed with water and dried over anhydrous sodium sulfate, and the soln was distilled off under reduced pressure, and purified by silica gel column chromatography to give a refractive index (++69.6) of 1.5495=8.
1 g of the desired product was obtained.

Examples of representative compounds of the present invention are listed below: Compound No.
1 2-(2.4-dikuoe+7.=ru)-4-(
3-pyridyl)-2-propen-1-one
Melting point: 69-73°C Compound No. 2 2-(2.
4-tsukuoo7. =L)-1-(3-pyrinol)-2-
Buten-1-one refractive index (068.2)
1.4906 Compound No. 3 2-(2,4-dichlorophenyl)-1-(3-pyrinol)-2-pentene-
1-on refractive index (n69・G) 1.549
5 Compound No. 4 L (2,4-dichlorophenyl)
-3-7i thylamino-1-(3-pyridyl)-2-7
'open-1-one Melting point 145-151°C Compound No. 5 2, 3-bis(2,4-dichlorophenyl)-1-(3-pyridyl)-2-propene-
1-one Refractive index (nf, 7·') 1.5504 Compound No. 6 1. 3-bis(3-pyrinol)-2-
(2.4-dichlorophenyl)-2-propen-1-one Melting point 116-122°C Compound No. 7 3
-[2-(2,4-Dioxolan-2-yl)-1,3-dioxolan-2-yl]bilinone Refractive index (n?J.・2) 1.5604 Compound No. 8 3-[2-[1,2-bis(2,4
-dichlorophenyl)vinyl)-1,3-dioxolan-2-yl]bilinone Refractive index (n66・2) 1.494
5 Compound No., 9 3-[: 2-[1-(2,4-dikuoo],=l)-2-(3-pyridyl)vinyl)-1,
3-dioxolane-2-ylcopyridine
Refractive index (n66・3) 1.4895 Compound No. 10 3-C2-(2,4-dikuoo-α-
methylenehensyl)-4,5-dimethyl-1,3-dioxolane-2-ylcopyridine refractive index (n65・2) 1
．． 5448 Compound No. 11 3-(2-(2-aa-4-fluoro-a-methylenebenzyl)sugar, 3-dioxolane-
2-ylcopyridine compound No. 12 3-[2-(4
-)lifluoromethyl-Q-1f-lenbenzyl)-1,
, 3-dioxolane-2-ylcopyridine compound No.
13 3-(2-(2,4-dichloro-α-/tylenehensyl)thiazolidin-2-ylcopyridine Compound No., 14 342-(2,4-dichloro-α-
(2,2,2-trifluoro)ethylidenebenzyl)-
1,3-dioxolan-2-yl]pyrinone 11 The compound of the present invention is useful as a pharmaceutical antifungal agent and an agricultural and horticultural fungicide, as shown in the test examples below. rice blast disease,
Rice sheath blight, cucumber anthracnose, cucumber powdery mildew, tomato late blight, tomato ring spot, citrus black spot, citrus green mold, Rinko 1 black spot, apple leaf spot and leaf spot, fungi,
It exhibits excellent control effects against soil diseases caused by plant pathogenic bacteria such as Rhizoctonia fungi, Particillium fungi, and Plasmodiophora fungi. It is particularly effective in controlling powdery mildew, gray mold, sclerotium, and rust. The compound of the present invention has not only a preventive effect but also a therapeutic effect, and furthermore, it has excellent permeability, so by applying it to soil, it can control diseases on foliage and foliage. . The compounds of the present invention also exhibit excellent control effects against mites that are harmful in agriculture and horticulture, such as two-spotted spider mites and red-spotted spider mites.

When used, it can be formulated into various forms such as emulsions, powders, wettable powders, liquids, etc. together with adjuvants, as in the case of conventional agrochemical formulations. 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 auxiliary agents mentioned here 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,
Examples include mineral powders such as calcium carbonate, zeolite, diatomaceous earth, white carbon, clay, alumina, and sulfur powder.As liquid carriers, water, alcohols such as methyl alcohol and ethylene glycol, acetone,
Ketones such as methyl ethyl ketone, ethers such as dioxane and tetrahydrofuran, aliphatic hydrocarbons such as kerosene and kerosene, xylene, trimethylbenzene,
Aromatic hydrocarbons such as tetramethylbenzene, cyclohexane, and solvent naphtha; halogenated hydrocarbons such as chloroform and chlorobenzene; acid amides such as dimethylformamide; esters such as acetic acid ethyl ester, fatty acid esters, and lycerin ester; Examples include nitriles such as acetonitrile, sulfur-containing compounds such as dimethyl sulfoxide, and the like.

The application concentration of the compound of the present invention varies depending on the target crop, application method, formulation form, application amount, etc. - Although it cannot be generally specified, it is usually 1 to 10,000 p per active ingredient.
pm, preferably 20 to 2.000 ppm.

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

For example, as an insecticide, acaricide, or nematicide,
0-(4-bromo-2-chlorophenyl)0-ethyl
S-propyl phosphorothioate, 2,2-dichlorovinyldimethyl phosphate, ethyl 3-methyl-
4-(Methylthio)phenyl isopropyl phosphoramidate, 0.0-dimethyl0-4-nitro-m-1-
Lyle phosphorothioate, 0-ethyl 0-4-nitrophenyl phenylphosphonothioate, 0.0-diethyl 0-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate, 0.0-dimethyl
O-(3,5,6-dolychloro-2-pyridyl) phosphorothioate, 0. S-dimethyl acetyl phosphoramidothioate, O-(2,4-dichlorophenyl)
Organic phosphate ester compounds such as 0-ethyl S-propyl phosphorodithioate; 1-naphthyl methyl carbamate, 2-isopropoxyphenyl methyl carbamate, 2-methyl-2-(methylthio)propionaldehyde O - methylcarbamoyloxime,
2.3-dihydro-2,2-dimethylbenzofuran-7
-yl methyl carhamate, dimethyl N, N'
−[thiobis[(methylimino)carbonyloxy]
] Bisethanimidothioate, S-methyl N-(methylcarbamoyloxy)thioacetimidate, N,
N-dimethyl-2-methylcarbamoyloxyimino-
2-(Methylthio)acetamide, 2-(ethylthiomethyl)phenyl methylcarbamate, 2-dimethylamino-5,6-dimethylpyrimidin-4-yl dimethylcarbamate, S,S''-2-dimethylaminotrimethylenebis( carbamate compounds such as thiocarbamate), 2,2.2-)lichloro1゜1-bis(
(R3)-α-
Cyano-3-phenoxybenzyl (R3)-2-(4
-chlorophenyl)-3-methylbutylene, 3-phenoxybenzyl (IR3)-cis, trans-1-(
2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, (R3)-α-cyano-3-
Phenoxybenzyl (IR3)-cis.

trans-3-(2,2-dichlorovinyl)-2,2-
Dimethyl cyclopropane carboxylate, (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. Pyrethroid compounds such as 3-)lifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate; 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,
2 tert-butylimino-3-isopropyl-5-phenyl-3, 4
, 5゜6-titrahydro2) 1-1.3.5-thiadiazin-4-one, trans-di-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxothiazolidinone-3-carboxamide , N-methylbis(
Compounds such as 2,4-xylyliminomethyl)amine; isopropyl(2E,4E)-11-methoxy-3
,7,11~Juvenile hormone-like compounds such as trimethyl-2,4-dodeccasinoate; Also, as other compounds, dinitrate-18 = mixed use with metals, organic sulfur compounds, urea compounds, tri-pesticides, etc. , can also be used together.

For example, as a fungicide, S-benzyl 0゜0-diisopropyl phosphorothioate, 〇-ethyl S,S
-diphenyl phosphorodithioate, aluminum
Organophosphorus compounds such as ethylhydrogen phosphonate; Organochlorine compounds such as 4,5,6.7-titrachlorophthalide and tetrachloroisophthalonitrile; Manganese ethylene bis(dithiocarbamate)
Polymers of ethylene bis(dithiocarbamate), complexes of zinc and maneb, dizinc
Dithiocarbamate compounds such as polymers of bis(dimethyldithiocarbamate) ethylene bis(dithiocarbamate), zinc propylene bis(dithiocarbamate); 3a,4,7.7a-tetrahydro-N-(
trichloromethanesulfenyl)phthalimide, 3a,
4,7.7a-tetrahydro-N-(1,1,2,2-
Tetrachloroethanesulfenyl)phthalimide, N-
N-halogenothioalkyl compounds such as (trichloromethylsulfenyl)phthalimide; 3-(3,'5
-dichlorophenyl)-N-isopropyl-2,4-dioxoimidazolidine-1-carboxamide, (R3)
-3-(3,5-dichlorophenyl)-5-methyl-
Dicarboximide compounds such as 5-vinyl-1,3-oxazolidine-2,4-dione, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide; Methyl 1-(butylcarbamoyl)benzimidazol-2-yl carbamate, dimethyl 4,4”-(0-phenylene)bis(
benzimidazole-based compounds such as 1-(4-chlorophenoxyl-3,3-dimethyl-1-(IH-1,2,4-)lyazole-1);
-yl)butanone, ■-(biphenyyl-4-yloxy)-3,3-dimethyl-1-(IH-1,2,4-1
-riazol-1-yl)butan-2-ol, ■=(
N-(4-chloro-2-trifluoromethylphenyl)
-2-propoxyacetimidoylcoimidazole, 1
- (2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylmethyl)-1H-1
゜2.4-1-Riazole, 1- (2-(2,4-dichlorophenyl)-4-propyl-1゜3-dioxolan-2-ylmethyl]-IH-1,2,4-) Riazole, 1- (2-(2,4-dichlorophenyl)pentyl]-IH-1.Azole compounds such as 2,4-triazole; 2,4°-dichloro-α-(pyrimidine-
5-yl)benzhydryl alcohol, (±)-2,4
° -Carbinol-based compounds such as -difluoro-α-(IH-1,2,4-)lyazol-1-ylmethyl)benzhydryl alcohol; 3”-isopropoxy-o-toluanilide, α, α, α- Benzanilide compounds such as trifluoro-3'-isopropoxy-0-toluanilide; acylalanine compounds such as methyl N-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate; 3 -ri°koro-N-
Pyridinamine compounds such as (3-chloro-2,6-sinitro 4-α,α,α-trifluorotolyl)-5-trifluoromethyl-2-pyridinamine; other compounds include piperazine compounds, morpholine Examples include anthraquinone-based compounds, quinoxaline-based compounds, crotonic acid-based compounds, sulfenic acid-based compounds, urea-based compounds, antibiotics, and the like.

Test examples and formulation examples related to the present invention are described below.

=22= Test Example 1 Cucumber Gray Mold Prevention Effect Test Diameter 7,
Cultivate cucumbers (variety: four-leaf) in 5 cm plastic pots,
When the first leaf stage was reached, 10 m of a chemical solution containing each test compound adjusted to a predetermined concentration was sprayed using a spray gun. 24
After being kept in a greenhouse at 25°C for 1 day, disks (agar punching) of Botrytis fungi that had been cultured in advance on a potato-dextrose agar medium (PDA medium) were placed on cucumber leaves and inoculated. Three days after inoculation, the lesion length on the first leaf was investigated.
The control value was determined using the formula shown in Table 1, and the results are shown in Table 1.

Table 1 Experimental Example 2 Cucumber Gray Mold Treatment Efficacy Test Diameter 7,
Cultivate cucumbers (variety 24 leaves) in 5 cm plastic pots,
When the cucumber reached the one-leaf stage, disks (agar punching) of the Botrytis blight fungus, which had been cultured in advance on a potato-dextrose agar medium (PDA medium), were placed on cucumber leaves and inoculated.

After keeping it in a greenhouse at 20° C. for one day, 10 m/ml of a chemical solution containing the test compound adjusted to a predetermined concentration was sprayed using a spray gun. Three days after inoculation, the length of the lesion on the first leaf was investigated, and the control value was determined in the same manner as in Test Example 1, and the results shown in Table 2 were obtained.

Table 2 Test Example 3 Cucumber powdery mildew preventive effect test Diameter 7,
Cultivate cucumbers (variety: four-leaf) in 5 cm plastic pots,
When the first leaf stage was reached, 10 m# of a chemical solution containing each test compound adjusted to a predetermined concentration was sprayed using a spray gun. 24
After keeping the seedlings in a greenhouse at 25°C for 1 day, they were inoculated with conidia of powdery mildew. Ten days after inoculation, the lesion area ratio (χ) on the first leaf was investigated, and the control value was calculated using the following formula, and the results shown in Table 3 were obtained.

Table 3 - Experimental Example 4 Cucumber powdery mildew treatment efficacy test Diameter 7.5
Cucumbers (variety: Yotsuba) were grown in cm-sized polyethylene pots, and when they reached the one-leaf stage, they were inoculated with conidia of powdery mildew. Two days later, 10 ml of a chemical solution containing each test compound adjusted to a predetermined concentration was sprayed using a spray gun.

After keeping it in a greenhouse at 24°C to 25°C for 10 days, the lesion area ratio (χ) on the first leaf was investigated, and the control value was determined in the same manner as in Test Example 3, and the results are shown in Table 4. I got it.

Table 4 Test Example 5 Kij, □ Tree Powdery Mildew Treatment Effect Test Diameter 7
Cultivate cucumbers (variety: four-leaf) in 5-cm plastic pots, and when they reach the one-leaf stage, apply 10 m# of a chemical solution containing each test compound to a specified concentration onto the soil surface using a vipe and two pots. Irrigated. After being kept in a greenhouse at 24°C to 25°C for 2 days, the furikake was inoculated with conidia of powdery mildew. Ten days after inoculation, the lesion area ratio (χ) on the first leaf was investigated.
The control value was determined in the same manner as in the case of , and the results shown in Table 5 were obtained.

Table 5 Test Example 6 Cucumber and Disease Prevention Effect Test Diameter 7,5
Cucumbers (variety: Yotsuba) were grown in 1/4-inch plastic pots, and when they reached the two-leaf stage, 10 ml of a chemical solution containing each test compound at a predetermined concentration was sprayed using a spray gun. 24℃～
After being kept in a greenhouse at 25° C. for one day and night, a spore suspension of downy mildew was inoculated by spraying. 6 days after inoculation, the lesion area rate on the first leaf (
χ) was investigated, and the control value was determined using the following formula, and the results shown in Table 6 were obtained.

Table 6 Test Example 7 Rice blast preventive effect test Rice (variety: Chukyo Asahi) was grown in polyethylene pots with a diameter of 7.5 cm, and when it reached the 4-leaf stage, each test compound was adjusted to a predetermined concentration. 10 ml of the chemical solution was sprayed using a spray gun. After being kept in a greenhouse at 24°C to 25°C for one day and night, a spore suspension of rice blast fungus was spray inoculated. Five days after inoculation, the number of lesions on the third leaf was investigated, and the control value was calculated using the following formula, and the results shown in Table 7 were obtained.

Table 7 Test Example 8 Preventive effect on rice sheath blight KM Paddy rice (variety: Chukyo Asahi) was cultivated in a polyethylene pot with a diameter of 7.5 cm, and when it reached the 5-leaf stage, each test compound was adjusted to the specified concentration. 20mm of chemical solution! was sprayed using a spray gun. After being kept in a greenhouse at 24°C to 25°C for one day and night, rice straw on which sheath blight bacteria had been cultured was sandwiched between the leaf sheaths and inoculated. After keeping the plants in an inoculation room at a temperature of 28° C. and a humidity of 100× for 5 days, the lesion length of 5 stems per pot was investigated, and the control value was calculated using the following formula, and the results shown in Table 8 were obtained.

Table 8 Test Example 9 Oat crown rust preventive effect test Diameter 7, 5
Cultivate oats (variety: Shingen) in a cm polyethylene pot,
When the leaf stage is reached, 10 mj of chemical solution containing each test compound adjusted to the specified concentration! was sprayed using a spray gun. 24
After being kept in a greenhouse at 25°C for 1 day, the conidia of the crown rust fungus were inoculated. The number of lesions on the second leaf was investigated 10 days after inoculation, and the control value was calculated using the following formula, and the results shown in Table 9 were obtained.

Table 9 Test Example 10 Antibacterial test (plant pathogenic bacteria) 10091)m
The precultured discs (agar punchings) of various plant pathogenic bacteria were transplanted onto a potato dextrose agar medium (PDA medium) containing 100 ppm of streptomycin and 100 ppm of each active ingredient compound. After culturing at 22°C for a certain period of time, the bacterial flora diameter was investigated, and the mycelial growth inhibition rate was calculated using the following formula.
The results shown in Table 10 were obtained.

Table 10 A: Apple leaf spot fungus (Alternaria ma upper) B: Sugar beet brown leaf spot fungus (Cercospora be, ticola) C
: Fusarium oxysporum f, sp
, raphani) D: Citrus green mold fungus (Penicillium digitatum)
E: Cucumber cotton spot disease fungus (4aphantdermatum) F: Cucumber seedling damping-off fungus (Rh1zoctonia 5olani) G: Apple y, star disease fungus (Venturia 1naequalis) ■:
Verticillium albo-atrum
)□Test'' 1 Example 11 Antibacterial test (fungi) Sabouraud agar medium with 1% 1000ppm kanamycin aqueous solution 10mj! 0 and 5 mfi of each chemical solution of the compound adjusted to a concentration of 200 ppm were added to each medium.

Trichophyton mentagrophytes (Trichophton metagrophytes) was placed on the agar as a test bacterium.
phVtes) and Trichophyton rubrum (Tri
chophto-n rubrum), 28
After culturing at ~30°C for 5 days, the growth status of the test bacteria was observed. As a result, Compound No. 2 was effective against Trichophyton mentagrophytes and Trichophyton rubrum.
3.6.8.9 and 10.

Test Example 12 Kidney bean/Red spider mite Rhinoceros mite; Cultivate kidney bean (variety: Taisho Kintoki) in a plastic pot with an experimental diameter of 7.5c+n, and when it reaches the first leaf stage, cut off the other leaves leaving one first leaf. Ta. Young adult two-spotted spider mite (Dico)
fol and organophosphate resistance) After inoculating about 30 animals,
These seedlings were treated with 20ml of a chemical solution adjusted to a predetermined concentration of each test compound.
11 for about 10 seconds. After air-drying, they were left in a constant temperature chamber with lighting at 25°C, and the survival rate was determined on the second day of release, and the mortality rate was determined using the following formula, and the results shown in Table 12 were obtained.

Table 12 Formulation Example 1゜(A) Compound No. 1 50 parts by weight (B) Di-
Clyte 40 (c) Sodium ligninsulfonate 7 (d) Dialkyl sulfosuccinate 3 The above ingredients were uniformly mixed to prepare a wettable powder.

Formulation example 2. ' (a) Compound No. 4 20 parts by weight (b) Di-
Kryte 72 (c) Sodium ligninsulfonate 84 or more were uniformly mixed to make a wettable powder.

Formulation example 3゜(a) Compound No. 6 5 parts by weight (b)
Talc 954 or higher was uniformly mixed to make a wettable powder.

Formulation Example 4 (a) Compound No. 3 20 parts by weight (b) Xylene 60 (c) Polyoxyethylene alkyl allyl ether 20 The above components were mixed and dissolved to form an emulsion.

Formulation example 5゜(a) Sikurite 78 parts by weight (b) β
-Naphthalenesulfonic acid sodium formalin condensate
2 (c) Polyoxyethylene alkyl sulfate 5 (d) White carbon 15 A mixture of the above components and compound NO61 were mixed in a weight ratio of 4=1 to prepare a wettable powder.

Claims (1)

[Claims] 1. General formula; ▲ Numerical formulas, chemical formulas, tables, etc. an alkyl group that may be substituted with an alkyl group; an amino group that may be substituted with an alkyl group; a phenyl group that may be substituted; or a pyridyl group that may be substituted; Z is a carbonyl group, a thiocarbonyl group, There are tables, etc. ▼ groups or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ groups (in the formula, Q_1 and Q_2 are oxygen atoms, sulfur atoms, or -NH- groups,
R_1 and R_2 are hydrogen atoms or alkyl groups, and n is an integer from 0 to 2. 2. General formula: ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X is a halogen atom, trifluoromethyl group, or nitro group, and Y is a hydrogen atom; an alkyl group that may be substituted with a halogen atom; An amino group that may be substituted with an alkyl group; a phenyl group that may be substituted; or a pyridyl group that may be substituted; Z is a carbonyl group, a thiocarbonyl group, a ▲ mathematical formula, a chemical formula, a table, etc. ▼ group or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ groups (in the formula, Q_1 and Q_2 are oxygen atoms, sulfur atoms or -NH- groups,
R_1 and R_2 are hydrogen atoms or alkyl groups, and n is an integer from 0 to 2.] A pest control agent characterized by containing a pyridine-based compound as an active ingredient.