JPH11193277A - Pyrimidine derivative, its production and harmful organism controller - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound having a pyrimidine skeleton, useful as an active ingredient for a harmful organism controller having secure effects, safely usable. SOLUTION: This compound is shown by formula I [R<1> to R<5> and R<10> to R<14> are each independently H, nitro, cyano, a halogen, a 1-6C alkyl, a 1-6C alkoxy or the like; R<6> to R<9> are each independently H, nitro, a halogen, a 1-6C alkyl, a 1-6C haloalkyl or the like; X<1> to X<4> are each O or the like; Q is a group of formula II (r<1> to r<10> are each independently H, a halogen, hydroxy or the like), phenylene or the like] such as 4,4'-[1,2-ethanediylbis(oxy)]bis[6-(4- fluoro-3-trifluoromethylphenoxy)pyrimidine]. The compound of formula I can be obtained, for example, by reacting a compound of formula III with a compound of formula IV (hal is a halogen) in the presence of a base such as triethylamine. Consequently the compound effective for controlling agriculturally harmful organisms, sanitary insect pests, grain insect pests, insect pests for clothing, etc., can be provided.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel compound having a pyrimidine skeleton and a pesticidal composition containing the compound as an active ingredient.

[0002]

2. Description of the Related Art Conventionally, a large number of insecticides and acaricides have been used, but their efficacy is insufficient, their use is limited due to problems with drug resistance, and phytotoxicity to plants is hindered. In many cases, it is difficult to say that it is a satisfactory control agent because of its high toxicity to humans, fish, and the like. Therefore, there is a need for the development of a drug that can be used safely with few such disadvantages. As a compound related to the present invention, WO94 /
JP-A-02470 describes the following compounds.

[0003]

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(Wherein r _{1 to} r ₁₀ represent a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, etc.
X ₁ and X ₂ simultaneously represent an oxygen atom, a sulfur atom, Nr ₁₁ or the like. )

[0005]

SUMMARY OF THE INVENTION An object of the present invention is to provide a pesticidal agent which has a certain effect and can be used safely.

[0006]

That is, the general formula (1)

[0007]

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[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
R ¹⁰ , R ¹¹ , R ¹² , R ¹³ and R ¹⁴ each independently represent a hydrogen atom, a nitro group, a cyano group, a halogen atom,
R 1 represents a pyridyloxy group which may be substituted with a _1-6 alkyl group, C _1-6 haloalkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group or C _1-6 haloalkyl group;
⁶ , R ⁷ , R ⁸ and R ⁹ each independently represent a hydrogen atom, a nitro group, N (R ¹⁸ ) (R ¹⁹ ), a halogen atom,
Represents a C _1-6 alkyl group or a C _1-6 haloalkyl group. X ¹ , X ² , X ³ and X ⁴ are the same or different,
Represents O or N (R ¹⁵ ), and R ¹⁵ , R ¹⁸ and R ¹⁹ each independently represent a hydrogen atom, a C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a COR ¹⁶ (R ¹⁶ is
C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _1-6 alkoxy, and optionally substituted phenyl. ), SOnR ¹⁷ (R ¹⁷ represents a C _1-6 alkyl group, a C _2-6 alkenyl group, or a C _2-6 alkynyl group,
n represents 0, 1 or 2. ), And Q is the following equation

[0009]

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(Wherein r ¹ , r ² , r ³ , r ⁴ , r ⁵ ,
r ⁶ , r ⁷ , r ⁸ , r ⁹ or r ¹⁰ each independently represents a hydrogen atom, a halogen atom, a hydroxy group, a C _1-6 alkoxy group, a C _1-6 alkylcarbonyloxy group,
Represents a C _1-6 alkyl group which may be substituted with an amino group mono- or di-substituted with a _1-6 alkyl group or a benzyl group, or a phenyl group which may be substituted. ). And a pesticidal agent containing the compound as an active ingredient.

In the present invention, R ^{1 to} R ⁵ and R ^{10 to} R ¹⁴
Represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc., and the C _1-6 alkyl group represents a methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t
-Butyl and the like, and as the C _1-6 haloalkyl group,
Fluoromethyl, 1-fluoroethyl. Represents 2-fluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, fluorochloromethyl, trichloromethyl, tribromomethyl, trifluoroethyl, pentafluoroethyl, etc., and the C _1-6 alkoxy group is methoxy, ethoxy , Propoxy, isopropoxy, butoxy, etc., and the C _1-6 haloalkoxy group represents trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, trichloromethoxy, difluoromethoxy, etc., and has a substituent. Examples of the pyridyloxy group that may be used include a 2-pyridyloxy group, a 3-pyridyloxy group, a 4-pyridyloxy group, a 5-trifluoromethyl-2-pyridyloxy group, and the like.

The halogen atoms of R ⁶ , R ⁷ , R ⁸ and R ⁹ represent fluorine, chlorine, bromine and the like.
_1-6 alkyl groups include methyl, ethyl, propyl,
Isopropyl, butyl, s-butyl, t-butyl, etc., and the C _1-6 haloalkyl group includes fluoromethyl, 1-fluoroethyl. Represents 2-fluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, fluorochloromethyl, trichloromethyl, tribromomethyl, trifluoroethyl, pentafluoroethyl and the like.

The C _1-6 alkyl group for R ¹⁵ , R ¹⁸ and R ¹⁹ represents methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl, etc.
_{The 2-6} alkenyl group includes vinyl, allyl, crotyl and the like, and the C _2-6 alkynyl group includes ethynyl,
Represents propargyl, etc., and as COR ¹⁶ , acetyl,
Examples of the substituent of the optionally substituted phenyl group of propionyl, methoxycarbonyl, ethoxycarbonyl and R ¹⁶ include a nitro group, a halogen atom such as fluorine, chlorine and bromine, methyl, ethyl, propyl, isopropyl, butyl and s-butyl. represents C _1-6 alkyl group such as t- butyl. R ¹⁵ , R ¹⁸ and R ¹⁹ each represent a group represented by SO ₂ R ¹⁷ such as methylsulfonyl, ethylsulfonyl, vinylsulfonyl, allylsulfonyl, ethynylsulfonyl, propargylsulfonyl, methylsulfinyl, ethylsulfinyl, vinylsulfinyl represents allyl sulfinyl, ethynyl sulfinyl group represented by SOR ^17, such Propulsion Gills sulfinyl, methylthio, ethylthio, vinylthio, allylthio, ethynylthio, a group represented by SR ^17, such Puropagiruchio.

Further, the halogen atom in r ^{1 to} r ¹⁰ represents fluorine, chlorine, bromine and the like, and the C _1-6 alkyl group includes methyl, ethyl, propyl, isopropyl, butyl, s-butyl and t-butyl. Represents butyl, etc.
Examples of the _1-6 alkylcarbonyloxy group include methylcarbonyloxy, ethylcarbonyloxy, propylcarbonyloxy, isopropylcarbonyloxy, butylcarbonyloxy, s-butylcarbonyloxy, t-
Represents butylcarbonyloxy, and the C _1-6 alkyl group includes methoxymethyl, ethoxymethyl, methoxyethyl, methoxypropyl, dimethoxymethyl, diethoxymethyl, methylaminomethyl, dimethylaminomethyl, N-benzylmethylaminomethyl and the like. Represent.

In the compound of the present invention and the intermediate compounds described below, the substituent has 1 to 6 (C _1-6 ) or 2 to 6 (C _2-6 ) carbon atoms. Has 1 to 4 (C _1-4 ) or 2 to 4 carbon atoms.
(C _2-4 ). The same applies to the following.

[0016]

BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention can be produced, for example, as follows. (Production method 1)

[0017]

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(Wherein R ^{1 to} R ¹⁴ , X ^{1 to} X ⁴ and Q are
Hal represents the same meaning as described above, and hal represents a halogen atom. )

That is, the compound represented by the general formula (2) is reacted with the compound represented by the general formula (3) in the presence of a base. Examples of a base that can be used in the reaction include triethylamine, diisopropylethylamine, pyridine, 1,8-diazabicyclo [5.4.
0] Organic bases such as 7-undecene (DBU), carbonates such as potassium carbonate and sodium carbonate, hydroxides such as sodium hydroxide and potassium hydroxide, sodium methoxide, sodium ethoxide, potassium-t-butoxide and the like And the like.
In addition, as a solvent that can be used in this reaction,
Amides such as N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMA) and N-methylpyrrolidone; ethers such as tetrahydrofuran (THF) and diethyl ether; alcohols such as methanol and ethanol; benzene , Toluene, xylene and other aromatic hydrocarbons, ethyl acetate and other esters, acetonitrile, dimethyl sulfoxide (DMS
O), sulfolane and the like. The reaction proceeds smoothly in the temperature range from 0 ° C. to the boiling point of the solvent used.

(Manufacturing method 2)

[0021]

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(Wherein R ^{1 to} R ¹⁴ , X ^{1 to} X ⁴ and Q are
Hal represents the same meaning as described above, and hal represents a halogen atom. )

That is, the compound represented by the formula (4) and the compounds represented by the general formulas (5) and (3) are
The reaction is performed in the presence of a base. Examples of the base that can be used in the reaction include organic bases such as triethylamine, diisopropylethylamine, pyridine, and DBU; carbonates such as potassium carbonate and sodium carbonate; hydroxides such as sodium hydroxide and potassium hydroxide; sodium methoxide; Sodium ethoxide, potassium-t
-Metal alkoxides such as butoxide.

Further, when X ³ or X ⁴ is NR ¹⁵ , the target compound can be obtained by allowing a catalyst such as palladium to coexist with a base in the reaction system. As the palladium catalyst, palladium chloride, bis (triphenylphosphine) dichloropalladium, tetrakis (triphenylphosphine) palladium, tris (benzylideneacetone) dipalladium / chloroform adduct, or the like can be used. The amount of the catalyst is given by the formula (3),
It is preferably from 1 mol% to 20 mol% based on 1 mol of the halopyrimidine represented by (5). When a palladium catalyst is used, triphanylphosphine, tri-o-
The reaction can be carried out in the presence of a phosphorus compound such as triarylphosphine such as tolylphosphine. Solvents that can be used in this reaction include DMF, DM
Amides such as A, N-methylpyrrolidone, ethers such as THF and diethyl ether, alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene, toluene and xylene, esters such as ethyl acetate, acetonitrile, Examples include DMSO and sulfolane. The reaction proceeds smoothly in the temperature range from 0 ° C. to the boiling point of the solvent used.

(Production method 3)

[0026]

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(Where R ^{1 to} R ¹⁴ , X ^{1 to} X ⁴ , and Q are
Hal represents the same meaning as described above, and hal represents a halogen atom. )

That is, after reacting the compound represented by the general formula (6) with the compound represented by the general formula (8) in the presence of a base, the compound represented by the general formula (7) is reacted. The same reaction is performed. Examples of the base that can be used in the reaction include organic bases such as triethylamine, diisopropylethylamine, pyridine, and DBU; carbonates such as potassium carbonate and sodium carbonate; sodium hydroxide;
Hydroxides such as potassium hydroxide, and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium-t-butoxide can be given. Solvents that can be used in this reaction include DM
Amides such as F, DMA, N-methylpyrrolidone, T
Examples include ethers such as HF and diethyl ether, alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene, toluene and xylene, esters such as ethyl acetate, acetonitrile, DMSO, and sulfolane. The reaction proceeds smoothly in the temperature range from 0 ° C. to the boiling point of the solvent used.

The compound represented by the general formula (2) and the compound represented by the general formula (8), which are intermediates of the present invention, can be produced as follows.

[0030]

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Some of the compounds represented by the general formula (8) are described in J. Am. Org. Chem. 44 (22) 3812-3
816 (1979). In addition, general formula (3), which is a raw material compound of the present invention,
The compound represented by (5) can be produced as follows.

[0032]

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After the completion of any of the reactions, the desired product can be obtained by performing post-treatments by a usual synthetic chemistry technique. Also, the determination of the structure of the reaction product
Performed by NMR, IR, MASS and the like.

[0034]

Next, the present invention will be described more specifically with reference to examples and reference examples.

Example 1 Preparation of 4,4 '-[1,2-ethanediylbis (oxy)] bis [6- (4-fluoro-3-trifluoromethylphenoxy) pyrimidine] (Compound No. 1)

[0036]

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0.12 g of 60% sodium hydride in DMF
At room temperature, 2 ml of a DMF solution of 0.51 g of 4-fluoro-3-trifluoromethylphenol was added to 6 ml of the suspension. After about 5 minutes, 0.4 g of 4.4 '-[1,2-ethanediylbis (oxy)] bis (6-chloropyrimidine).
Was added, and the mixture was stirred at 50 to 60 ° C. for about 4 hours while heating. After cooling, the reaction solution was poured into water, extracted with ethyl acetate, washed with water, and the organic layer was dried over anhydrous magnesium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography (hexane / ethyl acetate = 6/1) to obtain 0.68 g of the desired product as white crystals. m. p. 99-1
01 ° C

The intermediate of this example, 4.4 '
-[1,2-ethanediylbis (oxy)] bis (6-
Chloropyrimidine) is described in J. Am. Org. Chem. 44
(22) 3812-3816 (1979). That is, 2 equivalents of 4,6-dichloropyrimidine and 1 equivalent of ethylene glycol are reacted in DMF in the presence of 2 equivalents of sodium hydride.

Reference Example 1 Production of 4-fluoro-3-trifluoromethylphenol

[0040]

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15.0 g of 4-fluoro-3-trifluoromethylaniline was dissolved in 69 ml of concentrated sulfuric acid, and 6.45 g of sodium nitrite was added thereto under ice-cooling, followed by stirring at a temperature of 5 ° C. or lower for 30 minutes. Furthermore, 6.45 g of borohydrofluoric acid
Was added under ice cooling, and the mixture was stirred at 5 ° C. or lower for 10 minutes. To the obtained reaction solution, 202 g of cupric nitrate trihydrate was added, and further, 12.0 g of cupric oxide was added little by little.
The mixture was further stirred for 2 hours. The reaction foamed violently. After the completion of the reaction, insolubles were filtered off, and the filtrate was treated with diethyl ether 5
00 ml was added and the mixture was separated. Then, the organic layer is 2.5N
500 ml of an aqueous sodium hydroxide solution and 300 ml of a 0.1N aqueous sodium hydroxide solution were added for extraction. The aqueous alkaline layer was acidified by adding concentrated hydrochloric acid, extracted with diethyl ether, and the organic layer was dried over anhydrous magnesium sulfate. The residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography to obtain 7.91 g of the desired product. Yield 52%

Example 2 4,4 '-[1,3-benzenediylbis (oxy)]
Production of bis [6- (4-fluoro-3-trifluoromethylphenoxy) pyrimidine] (Compound No. 28)

[0043]

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0.12 g of 60% sodium hydride in DMF
To 10 ml of the suspension, resorcinol 0.16 was added at room temperature.
g was added and stirred for 25 minutes. To this solution was added dropwise a solution of 0.8 g of 4-chloro-6- (4-fluoro-3-trifluoromethylphenoxy) pyrimidine in 5 ml of DMF at room temperature. After stirring for about 1 hour,
The mixture was heated and stirred at 75 ° C. for 7 hours. After cooling, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After evaporating the solvent, silica gel column chromatography (hexane / ethyl acetate = 6 /
1-7 / 3) to give 0.2 g of the desired product as a colorless viscous oil. Yield 23%. ¹ H-NMR (CDCl ₃ , δ ppm) 6.47 (s, 2H), 7.03-7.56 (m, 10H), 8.43 (s, 2H)

Example 3 4,4 '-[1,2-ethanediylbis (oxy)]-
Production of 6- (3-trifluoromethylphenoxy) pyrimidyl-6 ′-(4-fluoro-3-trifluoromethylphenoxy) pyrimidine (Compound No. 79)

[0046]

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0.06 g of 60% sodium hydride in DMF
0.23 g of 3-trifluoromethylphenol was added to 5 ml of the suspension under ice cooling, and the mixture was slowly returned to room temperature and stirred for 10 minutes. This solution was added to 4,4 ′-[1,
2-ethanediylbis (oxy)] bis (6-chloropyrimidine) was slowly added dropwise to a solution of 0.4 g of DMF in 5 ml of DMF, and the mixture was stirred at room temperature overnight. The reaction solution was poured into water, extracted with diethyl ether, and the organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 0.3 g of 4,4 '-[1,2-ethanediylbis (oxy)]-6-chloropyrimidyl-6'-(3-trifluoromethylphenoxy) pyrimidine as an oily crude product. . ¹ H-NMR (CDCl ₃ , δ ppm) 6.47 (brs, 4H), 6.26 (d, 1H), 6.82 (d, 1H), 7.30-7.58 (m, 4
H), 8.57 (s, 1H)

Next, a suspension of 0.03 g of 60% sodium hydride in 5 ml of DMF was added under cooling to 4-fluoro-3-
0.14 g of trifluoromethylphenol was added, and the mixture was slowly returned to room temperature and further stirred for 10 minutes. afterwards,
4,4 '-[1,2-ethanediylbis (oxy)]-
0.3 g of 6-chloropyrimidyl-6 '-(3-trifluoromethylphenoxy) pyrimidine was added and 50 to 60 ° C.
For about 5 hours under heating. After cooling, the reaction solution was poured into water, extracted with diethyl ether, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was subjected to silica gel column chromatography (n-
The product was purified by hexane / ethyl acetate = 10/1) and recrystallized from hexane to obtain 0.31 g of the desired product. Yield 79.7% m. p. 74-78 ° C

Example 4 Process for producing N, N'-dimethyl N, N'-bis [6- (4-fluoro-3-trifluoromethylphenoxy) -4-pyrimidyl] ethylenediamine

[0050]

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0.99 g of 4-chloro-6- (4-fluoro-3-trifluoromethylphenoxy) pyrimidine
(3.4 mmol), N, N'-dimethylethylenediamine 0.15 g (1.7 mmol), tris (dibenzylideneacetone) dipalladium chloroform adduct.
18 g (0.17 mmol), 0.22 g (0.7 mmol) of tri-m-tolylphosphine, and 0.23 g (2.4 mmol) of sodium-t-butoxide in 100 ml of toluene at 100 ° C. for 3 hours under a nitrogen atmosphere. The above was stirred. Thereafter, the reaction mixture was cooled to room temperature, and filtered through celite while washing unnecessary substances with ether. The filtrate was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.49 g of N, N′-dimethyl N, N′-bis [6- (4-fluoro-3-trifluoromethylphenoxy) -4-pyrimidyl] ethylenediamine. Obtained in a yield of 48%. Table 1 shows typical examples of the compounds of the present invention, including the above Examples.

[0052]

[Table 1001]

[0053]

[Table 1002]

[0054]

[Table 1003]

[0055]

[Table 1004]

[0056]

[Table 1005]

[0057]

[Table 1006]

[0058]

[Table 1007]

[0059]

[Table 1008]

[0060]

[Table 1009]

[0061]

[Table 1010]

[0062]

[Table 1011]

[0063]

[Table 1012]

[0064]

[Table 1013]

[0065]

[Table 1014]

[0066]

[Table 1015]

[0067]

[Table 1016]

[0068]

[Table 1017]

[0069]

[Table 1018]

[0070]

[Table 1019]

[0071]

[Table 1020]

[0072]

[Table 1021]

[0073]

[Table 1022]

[0074]

[Table 1023]

[0075]

[Table 1024]

[0076]

[Table 1025]

[0077]

[Table 1026]

[0078]

[Table 1027]

[0079]

[Table 1028]

[0080]

[Table 1029]

[0081]

[Table 1030]

[0082]

[Table 1031]

[0083]

[Table 1032]

[0084]

[Table 1033]

[0085]

[Table 1034]

[0086]

[Table 1035]

[0087]

[Table 1036]

[0088]

[Table 1037]

[0089]

[Table 1038]

[0090]

BEST MODE FOR CARRYING OUT THE INVENTION (Insecticide and Acaricide) The compound of the present invention can be used for controlling agricultural pests, sanitary pests, storage pests, clothing pests, house pests, etc. Has larvicidal and ovicidal effects. The following are typical examples.

Lepidopteran insect pests, for example, Spodoptera litura, Spodoptera litura, Tamanayaga, Aomushi, Tamanaginiwaba, Konaga, Kanokokakumamonhamaki, Chahamaki, Momomoshiniga, Nashihimeshingui, Mikanhamoguriga, Kanohosoga, Kimmonhoganogomiga, Kimmonhoganogomiga, Komigahoganogomiga, Komigahoganogomiga, Komigahoganogomiga Hemiptera pests, such as the American white-faced starfish, Spodoptera litura, Heliotis, Helicoverpa, Agrotis, Iga, Codlinga, Cottontailed beetle, etc. Green stink bugs, scab beetles, stag beetles, stag beetles, whiteflies, tobacco whiteflies, pear whiteflies, nashigumba Worms, brown planthopper, small brown planthopper, Sejirounka, leafhopper and the like,

Coleoptera pests, for example, cynopodid beetles, burs beetle, colorado potato beetle, rice weevil, weevil weevil, adzuki beetle, beetle beetle, beetle beetle, genus diablotica, tobacco beetle, beetle beetle, pine beetle, beetle beetle , Coconut, cotton weevil, etc.

Diptera pests, for example, house flies, smelt flies, sentinia flies, sea flies, mandarin flies,
Pteridophyta, Rice leaf fly, Drosophila melanogaster, Drosophila melanogaster, Scarf mosquitoes, Aedes aegypti, Aedes aegypti, etc. Pests, for example, German cockroaches, Brown cockroaches, Black cockroaches, Tonosama grasshoppers, etc., Isopteran pests, for example, house termites, Yamato termites, etc., Pteridophyte pests, for example, human fleas, etc., louse pests, for example, human mites, e.g., mites, etc. , Spider mite, Kanzawa spider mite, mandarin spider mite, apple spider mite, mandarin mite,
Plant parasitic nematodes, such as apple rust mite, Dermatophagoid mite, Brevipalpas, Eotetranicus, Robin mite, Dermatophagoides farinae, Dermatophagoides farinae, Oxodid ticks, Phyllocarpus ticks, etc. etc.

[0094] In recent years, conger, planthopper, leafhopper,
Many insect pests such as aphids have developed resistance to organophosphates, carbamates and acaricides, and have caused problems of insufficient efficacy of these drugs. I have. The compound of the present invention is an agent having an excellent insecticidal and acaricidal effect against not only susceptible strains but also pests of an organophosphate, carbamate or pyrethroid-resistant strain and mites of acaricide-resistant strains. In addition, the compound of the present invention is a highly safe drug having little phytotoxicity, low toxicity to fish poisons and mixed-breed animals. The compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to underwater contacts such as ship bottoms and fish nets.

[Insecticide and Acaricide] When the compound of the present invention thus obtained is actually applied, it can be used in a pure form without adding other components, and it can be used in general for the purpose of being used as an agricultural chemical. It can also be used in the form that pesticides can take, ie, wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, flowables and the like. When a solid agent is intended as an additive and a carrier, soybean grains, vegetable powders such as flour, diatomaceous earth, dolomite, gypsum, talc, bentonite,
Mineral fine powders such as pyrophyllite and clay, and organic and inorganic compounds such as sodium benzoate, urea and sodium sulfate are used. When a liquid dosage form is intended, petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, water Is used as a solvent. In order to obtain a uniform and stable form in these preparations, a surfactant may be added, if necessary. Examples of the surfactant include, but are not particularly limited to, alkyl phenyl ether to which polyoxyethylene is added, alkyl ether to which polyoxyethylene is added, higher fatty acid ester to which polyoxyethylene is added, and sorbitan to which polyoxyethylene is added. Nonionic surfactants such as higher fatty acid esters, tristyryl phenyl ether added with polyoxyethylene, sulfates of alkyl phenyl ethers added with polyoxyethylene, alkyl benzene sulfonates, sulfates of higher alcohols, alkyls Examples include naphthalene sulfonate, polycarboxylate, lignin sulfonate, formaldehyde condensate of alkylnaphthalene sulfonate, and copolymer of isobutylene-maleic anhydride. The amount of the active ingredient is preferably 0.0.
The content is 1 to 90% by weight, more preferably 0.05 to 85% by weight. The wettable powder, emulsion, suspension,
The flowable agent is used by diluting it to a predetermined concentration with water to prepare a suspension or an emulsion, and the powder or granule is sprayed as it is.

It goes without saying that the compound of the present invention is effective alone, but it is also possible to use it in a mixture with one or more of various fungicides, insecticides and miticides or synergists. I can do it.

Representative examples of fungicides, insecticides, acaricides, and plant growth regulators which can be used by mixing with the compound of the present invention are shown below.

Fungicides: captan, folpet, thiuram, ziram, zineb, maneb, mancozeb, propineb, polycarbamate, chlorothalonil, kyntosen, captaphor, iprodione, prosimidon, vinclozolin, fluoroimide, thymoxanil, mepronil, flutranil, pencyclon, oxy Carboxin, fosetyl aluminum, propamocarb, triadimefon, triadimenol, propiconazole, diclobutrazole, bitertanol, hexaconazole,
Microbutanil, flusilazole, etaconazole,
Fluotrimazole, flutriafene, benconazole, diconazole, cyproconazoles, fenarimol, triflumizole, prochloraz, imazalil,
Perfurazoate, tridemorph, fenpropimorph,
Triforine, butiobate, pyrifenox, anilazine, polyoxin, metalaxyl, oxadixyl,
Furalaxyl, isoprothiolane, probenazole, pyrrolnitrin, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate, benomyl, carbendazim, thiophanate methyl, himexazole, basic copper chloride, basic copper sulfate, fentin acetate, triphenyl hydroxide Tin, dietofencarb, metasulfocarb, quinomethionate, binapacryl, lecithin, baking soda, dithianon, dinocap, phenaminosulf, diclomedine, guazatine, dozine, IBP, edifenphos, mepanipyrim, fermzone, triclamide, metasulfocarb, fluazinam, ethinolac, etoquinomorph Pyroquilon, Teclophthalam, Fusalide, Phenazine oxide, Thiabendazole, Tricycla Lumpur, vinclozolin, cymoxanil, cyclobutanyl, guazatine, propamocarb hydrochloride, oxolinic acid.

Insecticides and miticides: Organophosphorus and carbamate insecticides: phenthion, fenitrothion, diazinon, chlorpyrifos, ES
P, bamidothion, fentoate, dimethoate, formotion, marathon, trichlorfon, thiomethon,
Hosmet, dichlorvos, acephate, EPBP,
Methyl parathion, oxydimetone methyl, ethion,
Salithione, cyanophos, isoxathion, pyridafenthion, hosalon, methidathion, sulprophos, chlorfenvinphos, tetrachlorvinphos, dimethylvinphos, propaphos, isofenphos, ethylthiometon, profenophos, pyraclophos, monocrotophos, azinphosmethyl, aldicarb, mesomil, thiodicarb, Carbofuran, carbosulfan, benfracarb, flatiocarb, propoxur, BPMC,
MTMC, MIPC, carbaryl, pirimicarb, ethiophencarb, phenoxycarb and the like.

Pyrethroid insecticides: permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatrin, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propmethrin, phenothrin, prothrin, fluvalinate, cyfluthrin, cyhalothrin, flucitrinate, ethitol Fenprox, cycloprothrin, trolametrin, silafluofen, profenprox, acrinatrine and the like.

Benzoylurea and other insecticides: diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, methoprene, benzoepin, diafenthiu Ron, acetamiprid, imidacloprid, nitenpyram, fipronil, cartap, thiocyclam, bensultap, nicotine sulfate, rotenone, metaldehyde, machine oil, microbial pesticides such as BT and insect pathogenic virus.

Nematicides: fenamiphos, phosthiazate and the like.

Acaricides: chlorbenzylate, phenisobromolate, dicophor, amitraz, BPPS, benzomate, hexthiazox, fenbutatin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentezin, cyhexatin, pyridaben, fenpyroximate , Tebufenpyrad, pyrimidifen, phenothiocarb, dienochlor and the like.

Plant growth regulators: Gibberellins (eg, gibberellin A3, gibberellin A4, gibberellin A7) IA
A, NAA.

[0105]

EXAMPLES [Insecticide and acaricide] Next, some examples of the composition of the present invention will be described. However, the additives and the addition ratios are not limited to these examples, and may be varied over a wide range. It is possible. Parts in Formulation Examples are parts by weight.

Example 3 Water-dispersible powder 40 parts of the compound of the present invention 53 parts of diatomaceous earth 4 parts of higher alcohol sulfate ester 3 parts of alkyl naphthalene sulfonate If the above components are uniformly mixed and finely pulverized, the active ingredient 40
% Wettable powder.

Example 4 Emulsion 30 parts of the compound of the present invention 33 parts of xylene 30 parts of dimethylformamide 7 parts of polyoxyethylene alkylaryl ether 7 parts By mixing and dissolving the above, an emulsion having an active ingredient of 30% is obtained.

Example 5 Dusts 10 parts of the compound of the present invention 89 parts of talc 1 part of polyoxyethylene alkylaryl ether 1 part If the above components are uniformly mixed and finely pulverized, the active ingredient 10
% Powder.

Example 6 Granules Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Sodium phosphate 1 part The above components were thoroughly pulverized and mixed, and water was added and kneaded well.
The granules are dried by granulation to obtain granules having an active ingredient of 5%.

Example 7 Suspending agent Compound of the present invention 10 parts Sodium ligninsulfonate 4 parts Sodium dodecylbenzenesulfonate 1 part Xanthan gum 0.2 part Water 84.8 parts Mix above and until particle size is 1 micron or less If wet milled, a 10% active ingredient suspension is obtained.

[0111]

EFFECT OF THE INVENTION Test Example 1 Efficacy against armyworm According to the formula of wettable powder shown in Example 3 of the above-mentioned drug,
Diluted with water to give a compound concentration of 125 ppm.
Corn leaves were immersed in the solution for 30 seconds, air-dried, and then put into a petri dish containing five second-generation larvae of the armyworm. Glass cover, temperature 25 ℃, humidity 65%
And the insecticidal rate was examined after 5 days. Two repetitions. The results are shown in the following table.

[0112]

[Table 2]

Continuing on the front page (72) Inventor Tomohiro Takeda 345 Takada, Odawara-shi, Kanagawa Japan Nippon Soda Co., Ltd.Odawara Research Laboratories (72) Inventor Hidemitsu Takahashi 345 Takada, Odawara-shi, Kanagawa Japan Nippon Soda Co., Ltd.

Claims (5)

[Claims] 1. A compound of the general formula (1) [Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ¹⁰ , R ¹¹ ,
R ¹² , R ¹³ and R ¹⁴ each independently represent a hydrogen atom, a nitro group, a cyano group, a halogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _1-6 alkoxy group,
_{Represents a} pyridyloxy group which may be substituted with a _1-6 haloalkoxy group or a _C1-6 haloalkyl group, and represents R ⁶ , R ⁷ ,
R ⁸ and R ⁹ each independently represent a hydrogen atom, a nitro group, N (R ¹⁸ ) (R ¹⁹ ), a halogen atom, a C _1-6 alkyl group, or a C _1-6 haloalkyl group. X ¹ ,
X ² , X ³ and X ⁴ are the same or different and represent O or N (R ¹⁵ ), and R ¹⁵ , R ¹⁸ and R ¹⁹ are each independently a hydrogen atom, a C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, COR ¹⁶ (R ¹⁶ is a C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group,
Represents a C _1-6 alkoxy group or a phenyl group which may be substituted. ), SOnR ¹⁷ (R ¹⁷ is a C _1-6 alkyl group, C
_{Represents a 2-6} alkenyl group or a C _2-6 alkynyl group, wherein n is
Represents 0, 1 or 2. ), And Q is the following formula: (Where r ¹ , r ² , r ³ , r ⁴ , r ⁵ , r ⁶ , r ⁷ ,
r ⁸ , r ⁹ or r ¹⁰ are each independently a hydrogen atom, a halogen atom, a hydroxy group, a C _1-6 alkylcarbonyloxy group, a C _1-6 alkoxy group, a C _1-6 alkyl group or a benzyl group. Represents a C _1-6 alkyl group which may be substituted with a mono- or di-substituted amino group or a phenyl group which may be substituted. ). ] The compound represented by these. 2. A compound of the general formula (2) (Wherein, R ^{1 to} R ⁷ , X ¹ , X ³ , X ⁴ , and Q have the same meanings as described above) and a compound represented by the general formula (3): (Wherein, R ^{8 to} R ¹⁴ and X ² represent the same meaning as described above;
hal represents a halogen atom. Wherein the compound represented by the general formula (1) is reacted in the presence of a base. (Wherein, R ^{1 to} R ¹⁴ , X ^{1 to} X ⁴ , and Q have the same meanings as described above). (3) Formula (4) (In the formula, X ³ , X ⁴ and Q represent the same meaning as described above.)
And a compound represented by the general formula (5): (Wherein, R ^{1 to} R ⁷ and X ¹ represent the same meaning as described above;
hal represents a halogen atom. And a compound represented by general formula (3): (Wherein, R ^{8 to} R ¹⁴ and X ² represent the same meaning as described above;
hal represents a halogen atom);
General formula (1) characterized in that the reaction is carried out in the presence of a base. (Wherein R ^{1 to} R ¹⁴ , X ^{1 to} X ⁴ , and Q have the same meanings as described above). 4. A compound of the general formula (6) (Wherein, R ^{1 to} R ⁵ and X ¹ have the same meanings as described above) and a compound represented by the general formula (7): (Wherein, R ^{10 to} R ¹⁴ and X ² have the same meanings as described above) and a compound represented by the general formula (8): (Wherein, R ^{6 to} R ⁹ , X ³ , X ⁴ , and Q have the same meanings as described above, and hal represents a halogen atom) in the presence of a base. General formula (1) characterized by the following: (Wherein, R ^{1 to} R ¹⁴ , X ^{1 to} X ⁴ , and Q have the same meanings as described above). 5. A compound of the general formula (1) (Wherein, R ^{1 to} R ¹⁴ , X ^{1 to} X ⁴ , and Q have the same meanings as described above), which is characterized by containing one or more compounds as an active ingredient. Pest control agent.