JPH0370697B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention provides novel substituted N-alkyl-N-
Sulfenyl-carbamic acid-[2-(4-phenoxyphenoxy)- and 2-(4-phenylthiophenoxy)-ethyl] esters, processes for their preparation, and their use for pest control Regarding use. The carbamate ester of the present invention has the general formula: (In the formula, R ₁ represents an alkyl group having 1 to 4 carbon atoms; R ₂ represents a phenyl group, 1 or 2 halogen atoms or 1 to 2 carbon atoms; represents a phenyl group substituted by an alkyl group or the group -C( _CH3 ) ₂ -C≡
represents N, R ₃ represents a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms substituted with up to 3 halogen atoms; A is an oxygen atom or represents a sulfur atom, and n represents 0, 1, or 2. ). Desired compounds of the formula of the invention are:
R ₂ is a phenyl group, 1 or 2 fluorine atoms,
represents a phenyl group substituted by a chlorine or bromine atom or by one or two methyl groups, or a group -C( _CH3 ) ₂ -C≡N, and _R3 is a fluorine atom, A compound representing a chlorine atom, a bromine atom, a methyl group or a trifluoromethyl group. Among the compounds represented by the formula, particularly important compounds are those in which R ₂ is a phenyl group, 1 or 2
phenyl group substituted by chlorine atoms or methyl groups, or the group -C(CH ₃ ) ₂ -C≡N, and R ₃ is a chlorine atom or a trifluoromethyl group. A more desirable compound represented by the formula is
A compound in which R ₃ is bonded to the 2-position and/or 4-position of the phenyl ring, or R ₂ is a phenyl group,
4-chlorophenyl group, group -C( _CH3 ) _2- C≡N
Or it is a compound representing a 2,4-dimethylphenyl group. R ₃ is 2-Cl, 4-Cl or 4
- Compounds represented by the formula representing CF ₃ ; Compounds in which R ₁ represents a methyl group or an ethyl group; and n
Compounds in which is 0 are also of great interest because of their activity. Compounds of formula
No. 1573620). For example, a compound represented by the formula (a) is: (In the formula, R ₃ , A, and n represent the meanings defined in the above formula.) A compound represented by the following formula: (In the formula, R ₁ and R ₂ represent the meanings defined in the above formula, and X represents a halogen atom, preferably a chlorine atom.) or (b) a compound represented by the following formula: (In the formula, R ₁ , R ₃ and n represent the meanings defined in the above formula.) A compound represented by _the following _formula : X represents a halogen atom, preferably chlorine). The above steps (a) and (b) are preferably carried out at normal pressure,
It is carried out in the presence of an organic solvent or diluent. Suitable solvents or diluents are, for example, ethers and ethereal compounds, such as dipropyl ether,
dibutyl ether, dioxane, dimethoxyethane and tetrahydrofuran; N,N-dialkylated carboxylic acid amides, aliphatic, aromatic and halogenated hydrocarbons, especially benzene, toluene, xylene, chloroform, methylene chloride, carbon tetrachloride and chlorobenzene; acetone , methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone. Step (a) is generally carried out at temperatures from -10 to 200°C, preferably from 20° to 150°C, in particular at the boiling point of the inert solvent used and preferably in the presence of an acid acceptor. Step (b) is carried out at temperatures from -20 to 100°C, in particular from 0 to 50°C, and preferably also in the presence of an acid acceptor. In customary manner, the acid acceptors used in the aforementioned steps are bases and basic substances. Preferred bases are tertiary amines such as trialkylamines (eg triethylamine), pyridine, lutidine, which, when used in excess of a stoichiometric amount, act at the same time as a solvent. The starting materials of the formulas are known and can be prepared analogously to known methods. N-carboxycarbamic acid phenyl esters with insecticidal and acaricidal properties are known from DE 21 32 936 A1. moreover,
Substituted N-(4-phenoxyphenoxyethyl)- and N-(4-phenyl-thiophenoxyethyl)
- Carbamic acid alkyl esters are described in European Patent Application No. 0004334 as growth inhibitors with pesticidal activity. Substituted N-alkyl-carbamic acid-(4-phenoxyphenoxyethyl) esters, which also have an insecticidal and acaricidal effect, form the subject of British Patent Specification No. 1573620. On the other hand, in the case of the compounds of the invention, they are novel substituted N-alkyl-N-sulfenyl-carbamic acids-(4-phenoxyphenoxyethyl)- and 4-phenylthiophenoxyethyl-esters. and shows surprisingly increased activity as a pest control active substance. A further advantage of the compounds of the formula according to the invention is that they have negligible toxicity to warm-blooded animals and are virtually harmless to plants. The compounds represented by the above formula are particularly suitable for the orders Lepidoptera, Coleoptera, Homoptera, Heteroptera,
Diptera, Thysanoptera, Orthoptera, Anoplura, Siphonaptera, Mallophaga, Thysanura,
Orders Isoptera, Psocoptera and Hymenoptera
Suitable for controlling eye pests such as
The compound represented by the formula also acts as an acaricide (acaricidal action). In addition to controlling flies such as the house fly, and mosquito larvae, the compounds of the above formula are useful against insects that damage ornamental and beneficial plants, as well as fruits and foliage, by feeding, such as Las Peyrezia. Suitable for controlling Laspeyresia pomonella, Leptinotarsa decemlineata, Adoxophyesreticulana and Epilachna varivestis. The compounds represented by the above formula are characterized by a pronounced ovicidal action, particularly against the eggs of insects that damage plants by feeding. When the compound represented by the above formula is ingested by adult insects with food, many pests, especially insects of the order Coleoptera, such as Antonomus grandis, exhibit reduced oviposition and/or
or a decrease in hatching may be observed. Furthermore, the compounds of the above formula can be used to control ectoparasites in livestock and productive animals, such as the gold fly (Lucilia sericata) and ectoparasitic mites, for example by treating animals, livestock sheds and pastures. suitable for. The compounds according to the invention are suitable for use in zoonotic parasites such as Rhipicephalus bursa, Amblyomma helvaeum and Boophilus micropulus.
microplus), is particularly suitable for the control of. The action of the compounds of the invention and compositions containing them can be substantially extended and adapted to a given environment by the addition of local pest control agents. Examples of suitable additives include the following active substances: organophosphorus compounds, nitrophenols and their derivatives, formamidines, urea, carbamates, chlorinated hydrocarbons, pyrethroids, and bacillus thuringiensis preparations. . The compound represented by the above formula can be particularly advantageously used in combination with a substance that enhances pest control action. Examples of such compounds include piperonyl butoxide, propynyl ether, propynyl oxime, propynyl carbamate and propynyl phosphonate, 2-(3,4-methylenedioxyphenoxy)-3,6,9-trioxaundecane or S, Examples include S,S-tributyl phosphorotrithioate. The good insecticidal and acaricidal action of the compounds of the formula corresponds to a mortality rate of at least 50 to 60% of the previously mentioned pests. The compounds of the formula are used in neat form or preferably with the auxiliaries customary in pharmaceutical technology and can therefore be prepared in known manner, for example by
Concentrated emulsions, solutions that can be directly sprayed or diluted,
It is processed into dilute emulsions, wettable powders, soluble powders, powders or granules, and also capsules, for example in polymeric substances. The method of application is selected depending on the intended purpose and the given environment, as well as the nature of the composition. The preparations, i.e. compositions or formulations containing the active ingredient of the formula or the combination of this active ingredient with other insecticides or acaricides and optionally solid or liquid additives, can be prepared in a known manner, e.g. The active ingredient may be present in a bulking agent such as a solvent, a solid carrier,
and, if desired, by homogeneously mixing and/or milling with a surface-active compound (surfactant). Suitable solvents are: aromatic hydrocarbons, preferably C8-C12 fractions such as xylene mixtures or substituted naphthalenes; phthalate esters such as dibutyl or dioctyl phthalate; aliphatics such as cyclohexane or paraffin. Hydrocarbons; alcohols and glycols, and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or -ethyl ether; ketones, such as cyclohexanone; N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethyl formamide; and epoxidized vegetable oils such as epoxidized coconut oil or soybean oil; or water. Solid carriers used for example in dusts and dispersible powders are generally 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 granular adsorptive carriers are of porous type, for example 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 inorganic or organic materials can also be used, such as in particular dolomite or ground plant residues. Suitable surface-active compounds can be non-ionic, cationic and/or anionic, depending on the nature of the active ingredient to be incorporated or of the other insecticides or acaricides with which it is to be incorporated. It is a surfactant and has good emulsifying, dispersing and wetting properties. "Surfactant" also refers to mixtures of surfactants. Suitable anionic surfactants are both so-called water-soluble soaps and water-soluble synthetic surface-active compounds. Soaps that may be mentioned are alkali metal, alkaline earth metal or unsubstituted or substituted ammonium salts of higher fatty acids (from 10 to 22 carbon atoms), such as oleic acid or stearic acid or, for example, coconut oil. or sodium or potassium salts of natural fatty acid mixtures obtained from tallow. Also included are fatty acid methyltaurate salts and modified or unmodified phospholipids. However, so-called synthetic surfactants are more frequently used, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates. The fatty sulfonate or sulfate salt is usually an alkali metal, alkaline earth metal, or unsubstituted or substituted ammonium salt, and
It includes alkyl groups having 22 carbon atoms, where "alkyl" also includes the alkyl portion of acyl groups, such as lignin sulfonic acid, dodecyl sulfate or fatty alcohol sulfates prepared from natural fatty acids. A mixture of sodium or calcium salts. These also include sulfuric esters of fatty alcohol/ethylene oxide adducts and salts of sulfonic acids. The sulfonated benzimidazole derivatives preferably contain two sulfonic acid groups and a fatty acid group having 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. Also suitable are the corresponding phosphates, for example the salts of the phosphoric acid esters of the adducts of p-nonylphenol with 4 to 14 mol of ethylene oxide. Suitable nonionic surfactants are in particular polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which contain from 3 to 30 glycol ether groups and (aliphatic) 8 in the hydrocarbon group
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 propylene glycol and alkyl polypropylene glycols having 1 to 10 carbon atoms in the alkyl chain; contains 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. The above compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit. Examples of nonionic surfactants that may be mentioned are nonylphenol-polyethoxyethanol, castor oil polyglycol ether, polypropylene/polyoxyethylene adducts, tributylphenoxy-polyethoxyethanol, polyethylene glycol and octylphenol. Sea-polyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate, are also suitable. In the case of cationic surfactants, in particular at least one alkyl group having 8 to 22 carbon atoms as N-substituent and unsubstituted or halogenated lower alkyl groups, benzyl groups as further substituents. or a quaternary ammonium salt containing a lower hydroxyalkyl group. The salt is preferably in the form of a halide, methyl sulfate or ethyl sulfate, for example stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide. Surfactants commonly used in the pharmaceutical industry are described, for example, in the following publications: “McCutcheon's Detergents and Emulsifiers Annual.
Annual)”, MC Publishing, Ringwood, New Jersey, 1981; and
“Tensid-Taschenbuch” by H. Stache, Karlhausel Publishing, Munich/Vienna, 1981. Preparations for controlling pests usually contain from 0.1 to 99%, preferably from 0.1 to 95% of the compound of the formula or in combination with other insecticides or acaricides, and from 1 to 99.9% of solid or liquid adjuvants. , and 0 to 25%, especially 0.1 to 20%, of surfactants. While commercially available products are preferably in the form of concentrated compositions, products for consumer use are usually formulations with much lower concentrations of active ingredient. The composition may also contain other additives such as stabilizers,
Antifoams, viscosity modifiers, binders, adhesives and also fertilizers or other active substances may be included to obtain specific effects. Examples of formulations of active ingredients expressed by the formula or combinations thereof with other insecticides or acaricides (% = weight percent)

Table The required concentration of emulsion can be prepared from its concentrate by dilution with water.

[Table] Oil ligroin (boiling point limit − − 94% −
160~190℃)
The solution is suitable for application in the form of fine drops. (3) Granules (a) (b) Active ingredient or combination thereof 5% 10% Kaolin 94% - Highly dispersed silicic acid 1% - Attapulgite - 90% Dissolve the active ingredient in methylene chloride and dissolve the resulting solution. Spray onto the support and then evaporate the solvent under reduced pressure. (4) Powder (a) (b) Active ingredient or combination thereof 2% 5% Highly dispersed silicic acid 1% 5% Talc 97% - Kaolin - 90% Powder that can be used as is is a mixture of carrier and active ingredient that is homogeneous. Obtained by mixing. Examples of formulations of active ingredients expressed by the formula or combinations thereof with other insecticides or acaricides (%
= weight percent)

[Table] The active ingredient or combination thereof is thoroughly mixed with the additives and the mixture is thoroughly ground in a suitable mill. A wettable powder is obtained which can be made into a suspension of a desired concentration by diluting with water. (6) Emulsion concentrate active ingredient or combination thereof 10% octylphenol polyethylene glycol ether (4 to 5 moles of ethylene oxide)
3% Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (36 moles of ethylene oxide) 4% Cyclohexanone 30% Xylene mixture 50% The emulsion of the required concentration can be obtained by diluting this concentrate with water. (7) Powders (a) (b) Active ingredients or combinations thereof 5% 8% Talc 95% - Kaolin - 92% Ready-to-use powders are prepared by mixing the active ingredients with the agent and placing the mixture in a suitable mill. Obtained by grinding with (8) Extruded Granules Active Ingredients or Combinations thereof 10% Sodium Lignosulfonate 2% Carboxymethyl Cellulose 1% Kaolin 87% Mix and mill the active ingredients with the additives and moisten the mixture with water. This mixture is extruded, granulated, and then dried in a stream of air. (9) Coated Granules Active Ingredients or Combinations thereof 3% Polyethylene Glycol (MW200) 3% Kaolin 94% The pulverized active ingredients or combination thereof are uniformly applied to the kaolin moistened with polyethylene glycol in a mixer. In this way, dust-free coated granules are obtained. (10) Suspension concentrate active ingredients or combinations thereof 40% Ethylene glycol 10% Nonylphenol-polyethylene glycol (15 moles of ethylene oxide) 6% Sodium lignin sulfonate 10% Carboxymethyl cellulose 1% 37% formaldehyde aqueous solution 0.2% 75% aqueous Silicone oil in emulsion form
0.8% Water 32% When the finely divided active ingredient or combination thereof is homogeneously mixed with the additives, a suspended concentrate is obtained, which is then diluted with water to obtain a suspension of the desired concentration. Example 1 N-methyl-N-(2-isobutyronitrile)-
Preparation of sulfenyl-carbamic acid-[2-(4-phenoxy)-phenoxyethyl] ester 9.2 g of 2-(4-phenoxy)-phenoxy-ethanol were mixed at room temperature with 100 g of (anhydrous) toluene, 5 g of triethylamine and 4-dimethylaminopyridine. (2-fluorocarbonyl-4-cyano-4-methyl)-2-aza-3- was stirred in 0.4 g and then slowly dissolved in 20 ml of anhydrous toluene.
Add 7.05 g of sulfapentane dropwise. mixture
After stirring for 10 hours at 100° C., water is then added to the reaction mixture formed after cooling, the toluene phase is washed repeatedly with water, dried over sodium sulfate and concentrated by evaporation. The yellow oil obtained is chromatographed on silica gel using dichloromethane. After evaporative concentration, the following formula in the form of a light-colored oil with a refractive index n ²⁰ _D = 1.5583: The title compound (compound 1) represented by is obtained. Example 2 Preparation of N-ethyl-N-(4-chlorophenyl)-sulfenyl-carbamic acid-[2-(4-phenoxy)-phenoxyethyl] ester N-ethyl-carbamic acid-[2-(4-phenoxy)- 9 g of phenoxy-ethyl]ester were placed in 30 ml of pyridine and mixed with stirring and cooling.
-Chlorophenylsulfenyl chloride 5.4
Add g slowly and dropwise at 5 to 10℃. The reaction mixture is then stirred at 10° C. for 3 hours and at room temperature for 3 hours and then poured into a mixture of 300 ml of ice/water and 100 ml of toluene. The organic phase is washed with water, dried over sodium sulphate and concentrated by evaporation. The reddish oil formed is chromatographed on silica gel using a dichloromethane/hexane mixture (1:1 by volume) and finally pure dichloromethane. After evaporation and concentration,
Assuming a colorless oil with a refractive index n _20D = 1.5949, the following formula: The title compound (compound 2) represented by is obtained. The following compounds of the general formula are prepared by analogous procedures to those described above.

[Table] The following compounds of the formula can be obtained in a corresponding manner.

【table】

[Table] Example 3 Effect on house fly (Musca domestica) Freshly prepared CSMA nutrient medium for maggots 50
g into each of a series of beakers. The active ingredient concentration was determined by pipetting a specified amount of a 1% (by weight) acetone solution of each active ingredient into the nutrient medium in a beaker.
0.1-0.01%. After mixing the nutrient medium thoroughly,
Allow the acetone to evaporate for at least 20 hours. Twenty-five one-day-old house fly maggots per unit active ingredient and concentration are then placed into each beaker containing the treated nutrient medium. After the maggots pupate, the formed pupae are separated from the nutrient medium by flushing with water and placed in a container covered with a perforated lid. Count the number of shed pupae per batch (toxic effect of active ingredient on maggot development) and then
After 10 days, count the number of flies that have emerged from the pupa. The compounds of the formulas in Examples 1 and 2 show good effects in the above tests. Example 4 Effect on gold fly (Lucilia sericata) 1 ml of an aqueous preparation containing 0.5% of the active ingredient was
Add to 9 ml of medium at °C. Next, about 30 newly hatched golden fly maggots were placed in the medium, and 48 and
The insecticidal effect is determined by evaluating the mortality rate after 96 hours. The compounds of the formula according to Examples 1 and 2 show good action against the golden fly in this test. Example 5 Effect on Aedes aegypti 0.1% of each active ingredient on the surface of 150 ml of water in a container
By pipetting the acetone solution, concentrations of 800 ppm and 400 ppm of active ingredient are obtained, respectively. After the acetone has evaporated, 30 to 40 2-day-old Egyptian Aedes mosquito larvae are placed in each container. Mortality is calculated after 1, 2 and 5 days. The compounds of the formula according to Examples 1 and 2 show good action against the Egyptian Aedes mosquito in this test. Example 6 Gastrotoxic Insecticidal Effect Potted cotton plants approximately 25 cm high are sprayed with an aqueous emulsion containing the compound to be tested at concentrations of 400 and 800 ppm. After the spray coating has dried,
Spodoptera littoralis
The third instar larvae of Heliothis virescens and Heliothis virescens are used to infect cotton plants. The test is carried out at 60% relative humidity and 24°C. Determine mortality (percentage) after 120 hours. The compounds of the formula according to Examples 1 and 2 show a good effect in this test. Example 7 Epilachna varibesteis
Effect on Phaseolus vulgaris plants (shrub legume species) approximately 15-20 cm in height.
400ppm and 800ppm of the compound to be tested, respectively.
Spray an aqueous emulsion formulation containing a concentration of . After the spray coating has dried, five larvae of Epiracuna varibesteis (Mexican bean beetle) in the fourth larval stage are infested onto each plant. Copper-
A plastic cylindrical container covered with a gauge lid is placed over each treated plant. The test is carried out at 28°C and 60% relative humidity. Acute use (% mortality) is determined after 2 and 3 days. The damage to the plants due to feeding damage (anti-feeding effect) and the inhibition of development and molting are evaluated by observing the test insects for a further 3 days. The compounds of the formula according to Examples 1 and 2 show a good effect in this test. Example 8 Heliothis viretuscens
virescens) A corresponding amount of a wettable powder formulation containing 25% by weight of the active ingredient to be tested is mixed with a specified amount of water to form an aqueous emulsion with successively increasing concentrations of the active ingredient. The one-day-old spawn on the Heliothis self-annex is immersed for 3 minutes in the respective emulsion described above containing the active ingredient to be tested and then suctioned onto a round filter. Groups of eggs thus treated are placed in Petri dishes and kept in the dark. Hatching rates compared to untreated controls are determined after 6 to 8 days. Assess by determining the lowest concentration required to kill 100% of the eggs. The compounds of the formula according to Examples 1 and 2 show a good effect in this test. Example 9 Laspeyresia pomonella
(Eggs) 24-hour-old laid eggs of Las Peiresia Pomonella are immersed on paper for 1 minute in acetone/water solutions containing increasing amounts of the active ingredient to be tested. After drying the solution on the eggs, transfer the eggs to a Petri dish and keep at a temperature of 28 °C. Hatching rates from treated eggs are determined after 6 days. Compound No. 1 of Example 1 shows 100% activity in this test at an active ingredient concentration of 0.2 ppm. Compound No. 3,
4, 12, and 13 at an active ingredient concentration of 0.02 ppm
It shows an effect of 80 to 100%. 80 to 100% effect is 0.75 ppm for Compound No. 11 and 14; Compound No.
3ppm for Compound No. 8; 50ppm for Compound No. 2; 100ppm for Compound No. 6 and 15;
200ppm; and 400ppm for compounds No. 7 and 10;
It is shown in Example 10 Antonomus grungis
Adults of Antonomas grandis, which have not been hatched for at least 24 hours, are transferred as a group of 25 beetles into cages with lattice walls. This cage containing the beetles is then immersed for 5 to 10 seconds in an acetone solution containing 1.0% by weight of the active ingredient to be tested. After drying the beetles again, they are placed in a lidded dish containing food for mating and oviposition. Rinse the laid eggs under running water two or three times per week, count the eggs, sterilize them by placing them in an aqueous disinfectant solution for 2 to 3 hours, and then contain the appropriate larval food. Place on a plate. Count the eggs after 7 days to see if larvae have emerged from the eggs. In order to assess the duration of the effect of the active ingredient to be tested on reproduction, the egg laying of the beetles is observed for a period of about 4 weeks. The evaluation is based on the reduction in the number of eggs laid and the number of hatched larvae compared to the untreated control test. The compounds of the formula according to Examples 1 and 2 show good anti-reproductive action in this test. Example 11 Testing the effect on ticks: acaricidal effect at each growth stage The test examples used were Rhipicephalus buras of the tick species, Amblyomma hebraeum, and Boophilus micropulus.
microplus) larvae (approximately 50 cases each), nymphs (approximately 25 cases each), and adults (approximately 10 cases each). The test insects are immersed for a short time in an aqueous emulsion or solution containing the substance to be tested at a specific concentration. The emulsion or solution contained in a small test tube is then absorbed onto woolen cotton, leaving the moist test insect in the treated test tube. Evaluation is carried out after 3 days for larvae and after 14 days for nymphs and adults. The minimum active substance concentration resulting in 100% mortality is determined based on the total volume of emulsion or solution, expressed in ppm of active substance. Compounds of the formulas of Examples 1 and 2 are effective at the concentration ranges listed below. Range: Larva: <0.1-100ppm Nymph: <1-10ppm Adult: <10-500ppm

Claims (1)

[Claims] 1 General formula I: (In the formula, R ₁ represents an alkyl group having 1 to 4 carbon atoms; R ₂ represents a phenyl group, 1 or 2 halogen atoms or 1 to 2 carbon atoms; represents a phenyl group substituted by an alkyl group or the group -C( _CH3 ) ₂ -C≡
represents N, R ₃ represents a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms substituted with up to 3 halogen atoms; A is an oxygen atom or represents a sulfur atom, and n represents 0, 1, or 2. ) Carbamate ester represented by 2. A compound represented by the general formula according to claim 1, wherein R ₃ is substituted with a phenyl ring at the 2- and/or 4-position. 3 R ₂ is a phenyl group; a phenyl group substituted by one or two fluorine atoms, chlorine atoms, or bromine atoms, or by one or two methyl groups; or a group -C ( CH ₃ ) ₂ -C≡N, R ₃ is a fluorine atom, a chlorine atom, a bromine atom,
A compound represented by the general formula according to claim 1 or 2, which represents a methyl group or a trifluoromethyl group. 4 R ₂ represents a phenyl group; a phenyl group substituted by one or two chlorine atoms or a methyl group; or a group -C(CH ₃ ) ₂ -C≡CN, and R ₃ represents a chlorine atom or A compound represented by the general formula according to claim 2, which represents a trifluoromethyl group. 5 R ₂ phenyl group, 4-chlorophenyl group, 2,
4-dimethylphenyl group or group -C( _CH3 ) _2-
Claims 1 to 4 representing C≡N
A compound represented by the general formula described in any one of the following items. 6 Any one of claims 1 to 5, wherein R ₃ is 2-Cl, 4-Cl or 4-CF ₃
A compound represented by the general formula described in section. 7. A compound represented by the general formula according to any one of claims 1 to 6, wherein R ₁ is a methyl group or an ethyl group. 8. Claim 1, in which n is 0,
A compound represented by the general formula described in item 3, item 4, item 5, or item 7. 9 Formula: The compound according to claim 8, which is represented by: 10th formula: The compound according to claim 8, which is represented by: 11 Formula: The compound according to claim 8, which is represented by: 12th equation: The compound according to claim 8, which is represented by: 13th formula: The compound according to claim 8, which is represented by: 14th formula: The compound according to claim 8, which is represented by: 15 (a) The following formula: (In the formula, R ₃ , A, and n represent the meanings given in the following formula.) A compound represented by the following formula: (In the formula, R ₁ and R ₂ represent the meanings given in the following formula, and X represents a halogen atom, preferably a chlorine atom.) or (b) a compound represented by the following formula: (In the formula, R ₁ , R ₃ and n represent the meanings given by the following formula) and _the compound represented by _the following formula: and X represents the meaning given in the above formula.) (In the formula, R ₁ represents an alkyl group having 1 to 4 carbon atoms; R ₂ represents a phenyl group, 1 or 2 halogen atoms or 1 to 2 carbon atoms; represents a phenyl group substituted by an alkyl group or a group -C
(CH ₃ ) ₂ -C≡N, R ₃ is a halogen atom, and has 1 to 4 carbon atoms.
or a C1-C4 alkyl group substituted by up to 3 halogen atoms, A represents an oxygen atom or a sulfur atom, and n represents 0, 1 or 2 . ) A method for producing a compound represented by 16 General formula as an active ingredient: (In the formula, R ₁ represents an alkyl group having 1 to 4 carbon atoms; R ₂ represents a phenyl group, 1 or 2 halogen atoms or 1 to 2 carbon atoms; represents a phenyl group substituted by an alkyl group or the group -C( _CH3 ) ₂ -C≡
represents N, R ₃ represents a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms substituted with up to 3 halogen atoms; A is an oxygen atom or represents a sulfur atom, and n represents 0, 1, or 2. ) with a suitable carrier and/or
or a pest control composition containing it together with other additives. 17. The composition according to claim 16, which is applied to insects and acarina or their habitat in a pesticidal effective amount to control them. 18. The composition according to claim 16 for controlling insects that harm plants. 19. A composition according to claim 17 for use as an ovicide.