JPS6197254A - Benzoylphenylurea derivative, manufacture and pesticidal use - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

Detailed Description of the Invention [Industrial Application Field] The present invention relates to a novel substituted N-benzoyl-y-2,5-cyclo-4-haloalkoxyphenylurea, its production method and production intermediate, and the novel compound. Concerning methods of use in pest control.

[Means for solving problems]

The present invention is based on the following formula: and R2 represents a C1-7 haloalkyl group containing 1-15 halogen atoms or a C3-7 halocycloalkyl group containing 1-13 halogen atoms, provided that R2 does not represent -OF or -0HF-OF1. Preferably R2 has 1 to 3 carbon atoms substituted with 1 to 7 halogen atoms.
is an alkyl group.

Among the compounds represented by the formula (2), preferred from the viewpoint of biological activity are those in which, if R3 represents a hydrogen atom, R2 represents a methyl group, methoxy group or methylthio group; and if Peng represents a fluorine atom; When R2 represents a fluorine atom, a methyl group, a methoxy group or a methylthio group; or when R3 represents a chlorine atom, R2 represents a chlorine atom, a methyl group, a methoxy group or a methylthio group.

Compounds of II which are of special interest in terms of effectiveness are those in which H and R3 simultaneously represent a fluorine or chlorine atom and, independently of each other, a methyl, methoxy or methylthio group. things, and especially R1 and R
2 simultaneously represents a fluorine atom or a chlorine atom, preferably a fluorine atom.

- A very preferred compound of formula (1) is a compound in which R3 is the following group:
-0HF! , -OF, , -OF, OHF, ,
-0 Peng OF,.

-0FF 0HCIF, -0Ft 0HO1t,
-0FF Co15, mar, 0HBrl.

-0F10HBrF, -C! F, 0HBr2, -0H1OHBrOH,Br, -0F(OF,)OHFO
F, , -OF,0HFOF (OF,), , -
OF, 0HF (representing OF, OF, or, especially when the horse in the formula is -OF, OHF,
.

-0FtOHFO4-OFtOHalt-&Take-OF
, 001. It represents one of the following. Also of interest are compounds of the formula (1) in which H represents a C5 -C7 haloalkyl radical containing 1 to 15 halogen atoms.

The compound represented by the formula
40975)).

Thus, for example, a compound of formula I can be prepared by a) combining a compound of the formula ■: with a compound of the following formula ■: &; or b) combining a compound of the formula ■: & with a compound of the following formula V: ya or C) can be obtained by reacting a compound represented by the formula (1) with a compound represented by the following formula (2):8.

In formulas (1) to (2) above, avian, avian and R2 have the same meanings as defined for formula I, and R is unsubstituted or substituted with a halogen atom, preferably a chlorine atom, having 1 to 1 carbon atoms. 8 represents an alkyl group.

Processes a) b) and C) above may preferably be carried out under normal pressure and in the presence of organic solvents or diluents.

Examples of suitable solvents or diluents are: ethers and niterial compounds such as diethyl ether, dipropyl ether, dibutyl ether, dioxane, dimethoxyethane and tetrahydro-7ranes: N,N-dialkylated carboxamides: aliphatic, aromatic and halogenated hydrocarbons, especially benzene; toluene, xylene, chloroform,
Methylene chloride, carbon tetrachloride, and chlorobenzene; nitriles such as a7tonitrile or haflopionitrile:
Dimethyl sulfoxide: and ketones, such as acetone,
Methyl ethyl ketone, methyl impropyl ketone and methyl im butyl ketone. a) The process is usually carried out at -10° to +200°C, preferably from 0° to 100°C, for example at room temperature, and if desired in the presence of an organic base such as triethylamine. b) The process is carried out at temperatures between 0° and 15°C.
It is carried out at 0° C., preferably the boiling point of the solvent used, optionally in the presence of an organic base such as dipyridine, and with or without addition of an alkali metal or alkaline earth metal, preferably sodium. For process C), for example the reaction of a urethane of formula (1) with an aniline of formula (2), a temperature range from about 60"Q to the boiling point of the reaction mixture is preferred, and the solvent used is an aromatic hydrocarbon, such as toluene, Preferred are xylene, chloropencene and the like.

The starting materials of formulas I and V are known and can be prepared by known methods. The starting material of formula (1) is a new compound and likewise constitutes an object of the present invention. The compound of the formula (1) can be suitably substituted using the following formula (2) by a known method, as described in Benzene, Journal of Organ Chemistry (J, Org, Ohem, 1964) (see also the references cited herein). (see also) K can be prepared by hydrogenation by a method analogous to that described, except that aniline of formula (I) can also be prepared by chemical reduction of the corresponding nitro compound of formula (e.g. can also be obtained by tin/HCl) [Houben-Wey
l), ``Methodendea organizier hemi- (
Methoden d.

org, Ohemie)]. Nitro compounds of formula (1) can be prepared by haloalkylation of 2,5-dichloro-4-ditrophenol. Another method for preparing aniline of formula
-Hydroxyaniline □ is haloalkylated and the acyl group is then removed, for example, by acid hydrolysis.

Benzoyl isocyanate represented by the formula ■ can be obtained from fF as follows [Journal of Agricultural Food Chemistry (J,
People gr, Food Ohem,) 21゜5A8笈Bi9
page 93; see 1975]: a formula that is new in itself ■
4-(hexafluoropropyloxy)phenylinocyanate (boiling point 95°C 10.01) represented by
can be produced, for example, by phosgenating aniline represented by formula (2) by methods commonly used in the art, and this also constitutes an object of the present invention. Benzamides of the formula V, which are used as further starting materials, are known (for example from Beilstein).
stein)”Handfu-7der Organitschen
Hemy (Handbuch der organisc)
hen Ohemie)” Vol. 9, p. 336).

The urethane represented by 2) can be obtained by reacting a benzoyl inocyanate represented by the formula I with a suitable alcohol, or by reacting a benzamide represented by the formula V with chloroformate Cl in the presence of a base. -00
(by reaction with the corresponding ester of 0R).

Surprisingly, the present inventors have discovered that the compounds of the present invention and their salts have excellent properties as pest control agents, and at the same time have sufficient tolerability to plants and warm-blooded animals. It was discovered that the toxicity was low. They are particularly suitable for controlling insects and representatives of the order Acarina that attack plants and animals.

In particular, the compound represented by the formula
optera), Coleoptera (Ooleoptera),
Homoptera, Hete
roptera), Hymenoptera (Diptera), Thysanoptera (Thysanoptera), Orthoptera (O
rthhoptera), Anop-Iura
), 8iphonaptera, Mallophaga, Thysanu
ra), Isoptera, Psocopte-ra, and Hymenoptera.
insects such as A. menoptera, as well as Acarinae (Ac.
Arina) Makabe abrasive (Ixodidae), Himekabe abrasive (Argasidae), Tetranikiji (Tetr
a-nychidae) and chicken wall abrasive (Dermany
ss 1dae). The compound of formula ■ is
Flies, such as Musca domestica
In addition to its action against ca) and mosquito larvae, insects that damage plants, especially insects that feed on plants,
In crops of ornamental and useful plants, especially in cotton [e.g. Subodoptera littoralis (S.
podoptera 1ittoralis) and Heliothis vi
rescens) and in fruit and vegetable crops [e.g. Lasp.
eyresia po-monella), Leptinotars decemlineata
a decemlineata) and Epilachna varives
It is also suitable for controlling tis). The compounds of the formula I exhibit a marked ovicidal and, in particular, larvicidal action against insects and against the larvae of insects which cause feeding damage. When the compound of formula ■ is ingested with food during the adult stage, the insects become prolific;
Anthonomus grandis (Ant), a member of the Coleoptera order
honomus grandis) K.

Compounds of formula I may further be used to control Lucilia sericata (Lucilia 5eri-c) in farm animals and production livestock.
ectoparasites, such as P. ata), preferably in animals, in cattle sheds,
It can also be used to control barns, stables, etc., as well as pastures by treating them.

The compounds of formula I are furthermore suitable for controlling the following types of mites which are harmful to fruit trees and vegetables: two-spotted spider mite (Te
trannychus urticae), black-necked spider mite (Tetranychus cinnabarinu)
s), Panonychus ul
mi), Fake Clover Hada = (Bryobia r
ubrioculus), orange spider mite (Panony
chus citri), pear rust mite (Erioph
yespiri), Eliof Jesus chorus, K (B
riophyesribis), x riophyesribis
Erio-phyes vitis,
Tarsonemus palidorus
pallidus), Phylocoptes vitis (P.
phyllocoptes vitis), phyllocoptes oleivola (phyllocoptes ole)
ivora).

A good pest control action of the compounds of formula I according to the invention corresponds to a mortality rate of at least 50 to 60,960 of the abovementioned pests.

The action of the compounds of formula (1) and compositions containing them can be substantially extended and adapted to the application environment by adding other insecticides and/or acaricides.

Examples of suitable additives include organophosphorus compounds, nitrophenol and their derivatives, formamide, urea,
Carbamates, pyrethroids, chlorinated hydrocarbons, and Bacillus thuringiensis.
ingiensis) formulations.

The compounds of formula I are used in neat form or as compositions, preferably with auxiliaries customary in formulation technology, and can be prepared in known manner as emulsion stock solutions, directly sprayable or dilutable solutions, diluted emulsions, water-containing emulsions, etc. It is formulated into agents, aqueous solutions, powders, granules, and encapsulates, for example with polymeric substances. The method of application, such as spraying, sprinkling or pouring, as well as the nature of the composition, will be chosen depending on the intended audience and environment of use.

The formulations, i.e. the compositions containing the compound of formula I (active ingredient) and, if appropriate, solid or liquid auxiliaries, can be prepared in a known manner, e.g. by combining the active ingredient with a solvent, a solid carrier and, if appropriate, It is prepared by homogeneously mixing and/or milling with fillers such as surface-active compounds (surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably C8-C12 moieties, such as xylene mixtures or substituted naphthalenes, phthalates such as diptylphthalate or dioctyl heptatalate, hexanes or paraffins. aliphatic hydrocarbons such as ethanol, ethylene glycol monomethyl or monoethyl ether and their ethers and esters; ketones such as cyclohexanone; N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethyl Strong polar solvents such as formamide; and epoxidized vegetable oils such as epoxidized coconut oil or soybean oil; or water.

Solid carriers which can be used, for example in dusts and dispersible powders, are usually natural mineral fillers such as calcite, talc, kaolin, montmorillonite or attapulgite. It is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers to improve the physical properties. Suitable granulated absorbent carriers are of the porous type, e.g. pumice, crushed brick,
Sepiolite or bentonite: and suitable non-absorbent carriers are materials such as calcite or sand. Furthermore, a large number of pre-granulated mineral and organic materials can be used, especially dolomite or pulverized plant debris.

Depending on the nature of the compound of formula I to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants with good emulsifying, dispersing and wetting properties.

It is to be understood that the term "1 surfactant" also includes mixtures of surfactants.

Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic surface-active compounds.

Suitable compounds are alkali metal salts, alkaline earth metal salts, or unsubstituted or substituted ammonium salts of higher fatty acids (C1oSCH), such as oleic acid or stearic acid, or natural fatty acid mixtures obtained, for example, from coconut oil or tallow. is the sodium or potassium salt of Fatty acid methyltaurate salts may also be used.

However, more frequently so-called synthetic surfactants are used, especially aliphatic sulfonates, aliphatic sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates.

The aliphatic sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts and contain C8-C22 alkyl groups, which also include the alkyl part of acyl groups; Examples are the sodium or calcium salts of lignosulfonic acid, dodecyl sulfate or mixtures of fatty alcohol sulfates obtained from natural fatty acids. These compounds also include salts of sulfuric acid esters and salts of sulfonic acids of aliphatic alcohol/ethylene oxide adducts.

The sulfonated benzimidazole derivatives preferably contain two sulfonic acid groups and one fatty acid group containing 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or naphthalenesulfonic acid/formaldehyde condensation products. the corresponding phosphate,
Salts of the phosphoric esters of p-nonylphenol adducts containing, for example, 4 to 14 mol of ethylene oxide are also suitable.

The nonionic surfactants are preferably aliphatic or cycloaliphatic alcohols or polyglycol ether derivatives of saturated or unsaturated fatty acids and alkylphenols, which derivatives contain from 3 to 30 glycol ether groups, (aliphatic) 8 to 20 carbon atoms in the hydrocarbon portion and 6 to 18 carbon atoms in the alkyl portion of the alkylphenol.

Other suitable nonionic surfactants are water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediamine polypropylene glycol and alkyl polypropylene glycols containing 1 to 10 carbon atoms in the alkyl backbone; has 20 to 250 ethylene glycol ether groups and 10
Contains 6100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Typical examples of nonionic surfactants are nonylphenol-polyethoxyethanol and castor oil polyglycol.
Ether, polypropylene/polyethylene oxide adduct, tributylphenoxypolyethoxyethanol,
polyethylene glycol and octylphenoxyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan triolate, are also suitable nonionic surfactants.

The cationic surfactants preferably contain as N-substituent at least one C 8 -C 22 alkyl group and as other substituents lower unsubstituted or halogenated alkyl, benzyl or lower hydroxyalkyl groups. It is a quaternary ammonium salt containing. The salt is preferably in the form of a halide, methyl sulfate or ethyl sulfate, such as stearyltrimethylammonium chloride or benzyl di(2-10 loethyl)ethylammonium bromide.

Surfactants customary in the pharmaceutical industry are described, for example, in the following publications: McCutchan's Detergents and Emulsifiers
Cutcheon a Detergentsand
Emulsifiers Annual), Mack Publishers, Ringwood, New Jersey, 1979: Dr. Helmut Stallahier.

Helmut 5taChe), "'Ten5id-Taschenbuch"
h)”, Carl Hanser Ferler 9ri (Carl H
ILnser Verlag).

Munich and Vienna.

Pest control compositions usually contain a compound of formula I or a combination thereof with other insecticides or acaricides Q, 1 to 99%, preferably α1 to 95%, solid or liquid adjuvants 1 to 95%. 999% and 25% surfactant, preferably α1 to 25%.

Although commercial products are preferably formulated as concentrates, consumers typically use dilute formulations with substantially lower concentrations.

The compositions may also contain other additives such as stabilizers, antifoams, viscosity regulators, binders, viscosity agents and fertilizers or other active ingredients for special effects.

〔Example〕

Example 1 JL) 2e5-dichloro-4-(1*1j2*2-
Preparation of 4-acetylamino-2,5-dichlorophenol 18
．． 6t with powdered caustic potash & 11 and 150 ml of dimethylformamide in an autoclave. Next, 20 tons of tetrafluoroethylene is press-fitted into the closed autoclave. The mixture is stirred at 70° C. for 20 hours under the pressure generated in the autoclave.

After cooling, the mixture is concentrated by rotary evaporation and the residue is dissolved in methylene chloride. The resulting solution is washed with water, dried over sodium sulfate and concentrated. 2 with a melting point of 119-120 °C after recrystallization from a mixture of methylene chloride and hexane.
, 5-dichloro-4-(1',1',2-2'-tetrafluoroethoxy)acetanilide is obtained. 45 above
-dichloro-4-(1y1y2w2-tetrafluoroethoxy)acetanilide is, sr, ethanol 75
Keep under reflux for 10 hours with m1 and 25 ml of 37% hydrochloric acid. The reaction mixture was then concentrated, diluted with ice water,
And make it slightly alkaline. The product is extracted from the mixture with ethylene chloride. Wash the organic phase with water and NazSO
The methylene chloride is distilled off.

The crude product is then subjected to vacuum distillation to obtain a compound represented by the following formula: as a colorless liquid having a boiling point of 81-82° C./α05 torr.

Anilines of the formula I below are also prepared in a corresponding manner.

t t t CL b) Production of N-2-chlorobenzoyl-N-2,5-dichloro-4-(1,1',2,2-tetrafluoroethoxy)phenylurea.

5.5f of 2.5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline was dissolved in 60r of anhydrous toluene.
Dissolve in nll with stirring, and add 10 m of anhydrous toluene while excluding moisture! Add a solution of 2-chlorobenzoyl isocyanate S, 46f in the solution at room temperature. The contents are stirred for an additional 10 hours at room temperature. Next, by rotary evaporation, approximately 7
After removing 5% by volume of solvent, the precipitated residue was aspirated.
Filtration, washing with a small amount of cold toluene and hexane and then drying in vacuo give the title compound of the formula: in the form of colorless crystals with a melting point of 184-185°C. (Compound formula I below
The compound is prepared in a manner corresponding to the method described above: Compound RIR R3 Melting point ('C)2 HF
-CF, CHF, 167-11
583 F-0CHs-cF2CHFt
190-1914 HCL-C
F, CHFCt 165-1665 F
C1-CFzCHFC2165-1676H(?lt
-CF, CH(χ, 165-167
7 HC1-CF, CHFBr 161-1
628 HCL-CFzCHBr*
1729 F C1-CFzCHBr! 188
10 HF-CF*CHBr2
21511 F -0CHs -CFzCHB
r2 202-20314 F F-C
FzCHFctl 74-17522 CL C
L CFsCHBrz 21421
525 F F -CFCtCHFC
Z 148-15024 C1C1-CF
ClCHFCl 141]-14225F
CL 2cHF, 223
22426 F F-CHF2195-19627
HCL-CHFz 1c
pa Compounds of formula (1) below can also be produced by the above method.

28 HCL CFzCHFz Month CI
F-CF(CFs)CHFC
Fs32 Hcz -CFtCHFCF (CF
s) *35 FF -CFs56
-CH5-CH5-CRCHFz57 0CRs
0CHa -CFzCHFzExample 2 Formulation of the active ingredient of formula I according to Example 1 or a combination thereof with other insecticides or acaricides (% throughout)
(% by weight) 1. Wettable powder a) b) c) Compound or combination of formula I 25% 50% 7
5% Sodium Lignosulfonate 5% 5
% - Sodium lauryl sulfate 3%
-5% Highly dispersed silicic acid 5% 10% 10%
Kaolin 62% 27% - After the active ingredient or formulation is thoroughly mixed with the auxiliaries, the mixture is thoroughly ground in a suitable mill and then diluted with water to obtain a suspension of the desired concentration. You can get water conservancy.

2. Emulsion neat compound or formulation of formula I 10
% Calcium dodecylbenzenesulfonate 3
%cyclohexanone 3
0% xylene mixture 5
Emulsilone of a desired concentration can be obtained by diluting this emulsion stock solution with water.

5 Powder a) b) Compound or mixture of formula ■ 5% 8%
Talc 95% - Kaolin
- A ready-to-use powder is obtained by mixing the 92% active ingredient with the carrier and milling the mixture in a suitable mill.

4. Extruded granules Compound or blend of formula I 10%
Sodium lignosulfonate 2
% carboxymethyl cellulose 1
% Kaolin 8
The 7% active ingredient or formulation is mixed and milled with the auxiliaries and the mixture is subsequently moistened with water.

The mixture is extruded and dried in a stream of air.

5. Coating powder Compound or blend of formula I 3%
Polyethylene glycol 200 3%
Kaolin 94%
The finely divided active ingredient or formulation is applied homogeneously to the polyethylene glycol-moistened kaolin in a mixer. This method provides dust-free coated granules.

& Suspension stock formula■ Compound or mixture 40%
ethylene glycol 10
% Sodium Lignosulfonate 1
0% carboxymethylcellulose
1% 37% formaldehyde aqueous solution
(12% water
By homogeneously mixing the 32% finely ground active ingredient or formulation together with the auxiliaries and diluting with water, a suspension of the desired formulation can be obtained! l! ! It is a turbid pycnogenic concentrate.

Actions against each beaker are filled with freshly prepared nutrient media for maggots 502. Pipette an aliquot of a 1% acetone solution of each test compound into the nutrient medium in a beaker and
The active ingredient concentration is 0 ppm. The acetone is then allowed to evaporate for at least 20 hours after thoroughly mixing the medium.

Twenty-five one-day-old housefly maggots are placed in a beaker containing the test nutrient medium containing each active ingredient at the indicated concentrations. After the maggots have transformed, separate them by washing them out of the medium with water and place them in a container closed with a perforated lid.

Each batch of shed maggots is counted to determine the toxic effect of the test compound on maggot infestation. Measurements are made by counting the number of flies scored from the cage after 10 days.

In this test, the compound of formula I obtained in Example 1 showed a good effect.

1 ml aqueous formulation containing test compound at 5'% CL
is added to 9 ml of nutrient medium at 50°C. After that, about 3
The insecticidal effect is determined by adding 0 freshly graded Lucilia cercata larvae to the nutrient medium and assessing mortality after 48 and 96 hours. In this test, Example 1
The compound of formula Ⅰ prepared above showed good action against Lucilia cercata.

Example 5: Aedes aegypt
Effect on i) On the surface of 1 somJ of water in a beaker, (1 somJ of the test compound)
Add a certain amount of 1% acetone solution with a pipette to
A solution with a concentration of ppm is obtained. After the acetone evaporates,
Thirty to forty 2-day-old Egyptian Aedes mosquito larvae are placed in a beaker containing the test compound. Count the number of dead insects after 1, 2 and 5 days.

In this test, the compound of formula I according to Example 1 showed good action against the Egyptian Aedes mosquito.

Example 6: Insecticidal action against feeding insects Cotton plants with a height of about 25 C111 placed in pots are each sprayed with an aqueous emulsion containing the test compound at a concentration of 400 ppm. After the spray coating has dried, Spodoptera littoralis
Heliothisv
iriscens) glue stage 1 larvae inhabit cotton plants. The test is conducted at 24°C and 60% humidity.

The mortality rate (%) of the test insects can be determined after 120 hours.

Compound 1 at 400 ppm gave mortality rates of 80 to 100% for Subodoptera littoralis and Heliotis larvae.

Example 7: Mexican broad bean weevil (Epilach)
-na varivestis) action height 15
or 20cII Phaseolus vulgaris (Pha
seolus vulgaris) plant (red bean: dw
arf beans) are sprayed with an aqueous emulsion of the test compound at a concentration of aoo ppm. After the sprayed coating has dried,
MexiCan bea
Each plant is inhabited by five L4 stage larvae of L. nbeetle. Immediately cover the treated plants with a plastic cylinder and top with copper wire mesh. This test was conducted at 28℃.
Performed at 60% relative humidity.

Mortality is determined after 2 and 3 days. Insects in this test are observed for an additional 3 days to evaluate inhibition of feeding (piling phagocytosis) and inhibition of growth and molting.

In this test the compound of formula I according to Example 1 showed a good effect.

Example 8: Ovicidal activity against Heliothis virescens A corresponding amount of an aquarium containing 25% by weight of the test compound was
Mix with sufficient water to produce an aqueous emulsion containing the active ingredient at a concentration of 400 ppm.

One day old Heliothisvirescens eggs placed on cellophane are immersed in the emulsion for 3 minutes and collected by suction onto a round filter. The treated eggs are immediately placed in a Petri cage and kept in the dark at 28° C. and 60% relative humidity. After 5 to 8 days, the pancreatization rate, ie, the number of larvae hatched from the treated eggs, is determined in comparison with an untreated control group.

In this test, Compound 1 of Example 1 was 80 to 100
% of ovicidal activity.

Las Peiresia pomonella eggs within 24 hours after spawning are immersed on a piece of paper for 1 minute in an acetone solution containing 800 ppm of the test compound. After the solution has dried, the eggs are placed in a Petri dish and kept at a temperature of 28°C. After 6 days, the colony rate and mortality of larvae from treated eggs are evaluated. In this test the compound of formula 1 according to Example 1 showed a good effect.

! Adults of Anthonomus grandis within 24 hours of emergence are placed in groups of 25 in closed cages.

The cage is immersed for 5 to 10 seconds in an acetone solution containing 111% by weight of the test compound. Once the beetles are dry, they are placed in a covered dish containing food and left to mate and lay eggs.

Eggs are flushed under running water two to three times a week, counted, sterilized by placing them in an aqueous disinfectant for 2 to 3 hours, and then placed in a dish containing suitable larval food. After 7 days, the number, ie the number of larvae scored, is checked to determine the mortality of the eggs.

The persistence of the reproductive inhibitory effect of the test compound is determined by examining eggs over a period of 4 weeks. The evaluation is made by the reduction in the number of eggs and evaluated larvae compared to the untreated control group.

In this test, compound 1 according to Example 1 shows a good reproduction-reducing effect.

Cotton plants of the 2m variety at the 6-leaf stage in pots are sprayed with an irrigated emulsion containing the test compound at a concentration of 400 ppm. After the sprayed coating has dried (approximately 1 1/2 hours), each plant is injected with 10 adult beetles (Anthonomus grandis).
make animals live there.

A plastic cylinder with a mesh on top is immediately placed over the treated plant containing the insects to prevent the beetles from moving from the plant. Treated plants are kept at 25°C and 60% relative humidity. The evaluation is carried out after 2, 5.4 and 5 days by examining the mortality rate (percent dorsal) of the beetles and the anti-feeding effect compared to the untreated control group.

In the above test, Compound 1 represented by formula (2) of Example 1 showed a mortality rate of 80 to 100%.

Claims (28)

[Claims] (1) The following formula I: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R_1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, or a methylthio group, and R_2
represents a fluorine atom, a chlorine atom, a methyl group, a methoxy group or a methylthio group, and R_3 is a C1-C7 haloalkyl group containing 1 to 15 halogen atoms or a C1-C7 haloalkyl group containing 1 to 13 halogen atoms. represents a halocycloalkyl group having 3 to 7 carbon atoms, provided that R_3 does not represent -CF_2-CHF-CF_3. ) A compound characterized by being represented by: (2) The compound according to claim 1, wherein in formula I, R_3 represents an alkyl group having 1 to 3 carbon atoms substituted with 1 to 7 halogen atoms. (3) In formula I, if R_1 represents a hydrogen atom, R_2 represents a methyl group, methoxy group or methylthio group; if R_1 represents a fluorine atom, R_2 represents a fluorine atom,
represents a methyl group, a methoxy group or a methylthio group; or if R_1 represents a chlorine atom, R_2 represents a chlorine atom, a methyl group, a methoxy group or a methylthio group; Compounds described in. (4) The compound according to claim 3, wherein in formula I, R_1 and R_2 simultaneously represent a fluorine atom or a chlorine atom, or independently represent a methyl group, a methoxy group, or a methylthio group. (5) The compound according to claim 4, wherein in formula I, R_1 and R_2 simultaneously represent a fluorine atom or a chlorine atom. (6) The compound according to claim 5, wherein in formula I, R_1 and R_2 simultaneously represent a fluorine atom. (7) In formula I, R_3 is a group -CHF_2, -CF
_3, -CF_2CHF_2, -CH_2CF_3, -
CF_2CHClF, -CF_2CHCl, -CF_2
CCl_3, -CF_2CHBr_2, -CF_2CH
BrF, -CF_2CHBr_2, -CH_2CHBf
CH_2Br, -CF (CF_3) CHFCF_3, -
CF_2CHFCF(CF_3)_2, -CF_2CH
The compound according to any one of claims 1 to 6, which represents one of F(CF_2)_4CF_3 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. (8) In formula I, R_3 is a group -CF_2CHF_2
, -CF_2CHFCl, -CF_2CHCl_2 or -CF_2CCl_3. (9) The compound according to claim 1, wherein in formula I, R_3 represents a C5 to C7 haloalkyl group containing 1 to 15 halogen atoms. (10) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 6, which is represented by: (11) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 6, which is represented by: (12) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 6, which is represented by: (13) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 6, which is represented by: (14) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 6, which is represented by: (15) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 2, which is represented by: (16) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 2, which is represented by: (17) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 3, which is represented by: (18) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 3, which is represented by: (19) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 2, which is represented by: (20) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 3, which is represented by: (21) a) The following formula II: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) (In the formula, R_3 represents the following meanings.) The compound represented by the following formula III: ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (III) (In the formula, R_1 and R_2 represent the following meanings.) or b) The following formula IV: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IV) A compound represented by the following formula V: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (V) Or c) A compound represented by formula II is represented by the following formula VI: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ( VI) The following formula I characterized by reacting with a compound represented by (wherein R represents an unsubstituted or halogen-substituted alkyl group having 1 to 8 carbon atoms): ▲Mathematical formula, chemical formula, table, etc. ▼(I) (In the formula, R_1 represents a hydrogen atom, fluorine atom, chlorine atom, methyl group, methoxy group, or methylthio group, and R_2 represents a fluorine atom, chlorine atom, methyl group, methoxy group, or methylthio group. , and R_3 represents a C1 to C7 haloalkyl group containing 1 to 15 halogen atoms or a C3 to C7 halocycloalkyl group containing 1 to 13 halogen atoms, provided that R_3 does not represent -CF_2-CHF-CF_3). (22) The following formula II: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) (In the formula, R_3 is a haloalkyl group having 1 to 7 carbon atoms containing 1 to 15 halogen atoms, or 1 to 13 halogen atoms. represents a C3 to C7 halocycloalkyl group containing a halogen atom, provided that R_3 is -
Does not represent CF_2-CHF-CF_3. ) A compound characterized by being represented by: (23) Following formula IV: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (IV) (In the formula, R_3 is a haloalkyl group having 1 to 7 carbon atoms containing 1 to 15 halogen atoms or 1 to 13 carbon atoms represents a C3 to C7 halocycloalkyl group containing a halogen atom, provided that R_3 is -
Does not represent CF_2-CHF-CF_3. ) A compound characterized by being represented by: (24) The following formula I as an active ingredient: ▲Mathematical formula, chemical formula, table, etc.▼(I) (In the formula, R_1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, or a methylthio group, and R_2
represents a fluorine atom, a chlorine atom, a methyl group, a methoxy group or a methylthio group, and R_3 is a C1-C7 haloalkyl group containing 1 to 15 halogen atoms or a C1-C7 haloalkyl group containing 1 to 13 halogen atoms. represents a halocycloalkyl group having 3 to 7 carbon atoms, provided that R_3 does not represent -CF_2-CHF-CF_3. ) A pest control agent containing a compound represented by formula (1) together with a suitable carrier and/or other auxiliary agents. (25) The following formula I: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R_1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, or a methylthio group, and R_2
represents a fluorine atom, a chlorine atom, a methyl group, a methoxy group or a methylthio group, and R_3 is a C1-7 haloalkyl group containing from 1 to 15 halogen atoms or a C1-C7 haloalkyl group containing 1 to 13 halogen atoms. represents a halocycloalkyl group having 3 to 7 carbon atoms, provided that R_3 does not represent -CF_2-CHF-CF_3. ) is used to control typical insects and acarids. (26) The method according to claim 25 for controlling plant-damaging insects in the larval stage. (27) The method according to claim 25 for controlling insects as an ovicidal agent. (28) Insects and representatives of the order Acarina at their various developmental stages or in their habitats with a pesticidally effective amount of a compound represented by formula I or a pesticidal effective amount of the above compound. 26. The method according to claim 25, wherein the method is carried out by contacting with or treating with a composition containing the above together with an adjuvant and a carrier.