JPH0251883B2 - - Google Patents

Description

[Detailed Description of the Invention] The present invention relates to the general formula (In the formula, l is 0 or 1, and R ₁ represents a hydrogen atom or a methyl group. However, when l is 0, R ₁
represents only a methyl group. R ₂ is an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, or a halo group having 2 to 4 carbon atoms. Alkenyl group and formula (), (),
Indicates a group represented by (). [Formula] [Formula] [Formula] Here, R ₅ and R ₆ are a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a methoxy group, a methylthio group, a halomethyl group, a halomethoxy group, a nitro group, or R ₅ , R ₆ represents a methylenedioxy group.
Moreover, m and n are integers of 2 to 5, and R ₇ and R ₈ represent a hydrogen atom or a methyl group. R ₃ represents a hydrogen atom, a cyano group, an ethynyl group, or a methyl group, and R ₄ represents a hydrogen atom, a halogen atom, or a methyl group. ) The present invention relates to an insecticide and acaricide characterized by containing a cyclopropanecarboxylic acid ester derivative represented by the following. Up until now, organic phosphorus agents, carbamate insecticides, and chlorine insecticides have been the mainstream agricultural chemicals and have contributed to increased production of agricultural products, but they have caused environmental pollution and
Alternatively, from the standpoint of chronic toxicity, etc., there is a strong desire to search for safer compounds. Natural pyrethrins are excellent insecticides that are fast-acting and have low toxicity to humans, but their use has been limited to household use because they are susceptible to oxidative decomposition outdoors. In recent years, research into its acid and alcohol components has become active.
Several compounds have been discovered that are more photo-stable than conventional pyrethroids. For example, the present inventors found that the compound group represented by the general formula () is (JP-A-52-144712, 53-5717, etc., here l,
R ₁ , R ₂ and R ₃ have the same meanings as above. ) 1 It has high insecticidal power and is fast-acting. 2 It has a high residual effect, but there is no risk of environmental pollution. 3. Low toxicity to humans and animals. It has been revealed that it has the following characteristics and is extremely useful as an alternative to conventional organic phosphorus and carbamate insecticides. As a result of further intensive research, the present inventors found that the compound represented by the general formula () exhibits insecticidal power superior to the compound of the general formula (), and is particularly superior in acaricidal activity. They discovered that the toxicity was greatly reduced and completed the present invention. The compound represented by the above formula () used as an active ingredient in the present invention can be prepared using the general formula (In the formula, l is 0 or 1, and R ₁ represents a hydrogen atom or a methyl group. However, when l is 0, R ₁ represents only a methyl group. R ₂ is an alkyl group having 1 to 6 carbon atoms. , an alkenyl group having 3 to 5 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, a haloalkenyl group having 2 to 4 carbon atoms, and the formula (),
Indicates a group represented by () or (). [Formula] [Formula] [Formula] Here, R ₅ and R ₆ are a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a methoxy group, a methylthio group, a halomethyl group, a halomethoxy group, a nitro group, or R ₅ , R ₆ represents a methylenedioxy group.
Moreover, m and n are integers of 2 to 5, and R ₇ and R ₈ represent a hydrogen atom or a methyl group. ) Cyclopropanecarboxylic acid or its reactive derivative and the general formula (In the formula, R ₃ represents a hydrogen atom, a cyano group, an ethynyl group, or a methyl group, and R ₄ represents a hydrogen atom, a halogen atom, or a methyl group.) or a reactive derivative thereof. It can be prepared by Examples of reactive derivatives of cyclopropanecarboxylic acid include acid halides, acid anhydrides, lower alkyl esters, and alkali metal salts. Examples of reactive derivatives of alcohol include chloride, bromide, and p-toluenesulfonic acid ester. The reaction is carried out in a suitable solvent, optionally in the presence of an organic or inorganic base or acid as a deoxidizer or catalyst, and optionally with heating. The compound of the present invention of general formula () has two asymmetric carbon atoms in the acid component and one asymmetric carbon atom in the alcohol component when R ₃ is other than a hydrogen atom. The compounds of the present invention include their optical isomers and racemic mixtures, but unless otherwise specified in the Examples and Compound Examples described below, the produced compounds are racemic mixtures. Next, representative examples of the compound represented by the above formula () will be shown, but the present invention is of course not limited to these. 6'-Phenoxy-α'-cyano-2'-pyridylmethyl 2,2,3-trimethyl-3-methoxycyclopropanecarboxylate n ²⁰ _D 1.5319 6'-Phenoxy-α'-cyano-2'-pyridylmethyl 2,2,3-trimethyl-3-methoxymethylcyclopropanecarboxylate n ²⁰ _D
1.5350 6′-(4-methylphenoxy)-α′-ethynyl-
2'-Pyridylmethyl 2,2-dimethyl-3-cyclopropylmethoxymethylcyclopropanecarboxylate n ²⁰ _D 1.5548 6′-(4-bromophenoxy)-α′-methyl-
2'-pyridylmethyl 2,2-dimethyl-3-
(2-nitro-4-chloromethylphenoxymethyl)cyclopropanecarboxylate n ²⁰ _D
1.5608 6′-(4-methylphenoxy)-α′-cyano-
2'-pyridylmethyl 2,2,3-trimethyl-
(3-ethyl-4-difluoromethoxyphenoxy)cyclopropanecarboxylate n ²⁰ _D
1.5986 6'-Phenoxy-α'-ethynyl-2'-pyridylmethyl 2,2,3-trimethyl-3-(3-bromo-4-methylthiophenoxymethyl)cyclopropanecarboxylate n ²⁰ _D 1.5603 6'-(4-methylphenoxy)-2'-pyridylmethyl 2,2,3-trimethyl-3-(3-isopropyl-5-trifluoromethylphenoxy)
Cyclopropane carboxylate n ²⁰ _D 1.5975 6'-4-Fluorophenoxy)-α'-ethynyl-2'-pyridylmethyl 2,2,3-trimethyl-3-(3-methylcyclobutoxy)cyclopropanecarboxylate n ²⁰ _D 1.5670 6'-(4-bromophenoxy)-2'-pyridylmethyl 2,2,3-trimethyl-3-(3-methylcyclopentylmethoxymethyl)cyclopropanecarboxylate n ²⁰ _D 1.5769 6'-Phenoxy-α'-methyl-2'-pyridylmethyl 2,2,3-trimethyl-3-cyclopropoxymethylcyclopropanecarboxylate
n ²⁰ _D 1.5538 6′-(4-bromophenoxy)-α′-ethynyl-
2'-pyridylmethyl 2,2,3-trimethyl-
3-(2,2-dichloroethoxy)cyclopropanecarboxylate n ²⁰ _D 1.5748 6'-(4-methylphenoxy)-2'-pyridylmethyl 2,2-dimethyl-3-allyloxymethylcyclopropanecarboxylate n ²⁰ _D 1.5519 6′-(4-chlorophenoxy)-α′-methyl-
2'-pyridylmethyl 2,2,3-trimethyl-
3-(1-methyl-2-butynyloxymethyl)
Cyclopropane carboxylate n ²⁰ _D 1.5641 6'-phenoxy-2'-pyridylmethyl 2,2
-dimethyl-3-hexyloxymethylcyclopropanecarboxylate n ²⁰ _D 1.5583 6′-(4-fluorophenoxy)-α′-cyano-
2'-pyridylmethyl 2,2-dimethyl-3-
(2,2,2-trifluoroethoxymethyl)cyclopropanecarboxylate n ²⁰ _D 1.5425 6'-Phenoxy-α'-ethynyl-2'-pyridylmethyl 2,2,3-trimethyl-3-(2-bromoethoxymethyl)cyclopropanecarboxylate n ²⁰ _D 1.5690 6'-(4-bromophenoxy)-2'-pyridylmethyl 2,2,3-trimethyl-3-(2,3-
dibromoallyloxy)cyclopropanecakylboxylate n ²⁰ _D 1.5737 6'-(4-chlorophenoxy)-2'-pyridylmethyl 2,2,3-trimethyl-3-ethoxycyclopropanecarboxylate n ²⁰ _D 1.5409 6'-(4-methylphenoxy)-2'-pyridylmethyl 2,2,3-trimethyl-3-difluoromethoxymethylcyclopropanecarboxylate
n ²⁰ _D 1.5395 6′-(4-bromophenoxy)-α′-methyl-
2'-pyridylmethyl 2,2,3-trimethyl-
3-(3-methyl-2-butenyloxy)cyclopropanecarboxylate n ²⁰ _D 1.5680 6'-phenoxy-2'-pyridylmethyl 2,2
-dimethyl-3-propargyloxymethylcyclopropanecarboxylate n ²⁰ _D 1.5537 6'-(4-fluorophenoxy)-2'-pyridylmethyl 2,2-dimethyl-3-(2-chloro-
4-Trifluoromethylphenoxymethyl)cyclopropanecarboxylate n ²⁰ _D 1.5761 6'-(4-Fluorophenoxy)-α'-ethynyl-2'-pyridylmethyl 2,2,3-trimethyl-(2-methylallyloxymethyl)cyclopropanecarboxylate n ²⁰ _D 1.5423 6′-phenoxy-2′-pyridylmethyl 2,
2,3-trimethyl-(2-butynyloxy)cyclopropanecarboxylate n ²⁰ _D 1.5380 6′-(4-chlorophenoxy)-α′-cyano-
2'-pyridylmethyl 2,2-dimethyl-3-
(3,3-dichloroallyloxymethyl)cyclopropanecarboxylate n ²⁰ _D 1.5609 6′-(4-methylphenoxy)-α′-methyl-
2'-pyridylmethyl 2,2,3-trimethyl-
3-(2-trifluoromethylallyloxymethyl)cyclopropanecarboxylate n ²⁰ _D
1.5471 6'-Phenoxy-α'-cyano-2'-pyridylmethyl 2,2,3-trimethyl-3-(4-methoxyphenoxy)cyclopropanecarboxylate n ²⁰ _D 1.5804 6′-(4-bromophenoxy)-α′-ethynyl-
2'-pyridylmethyl 2,2-dimethyl-3-
(3,4-methylenedioxyphenoxymethyl)
Cyclopropane carboxylate n ²⁰ _D 1.5735 6'-Phenoxy-α'-methyl-2'-pyridylmethyl 2,2,3-trimethyl-3-(2-fluoro-4-tert-butylphenoxymethyl)cyclopropanecarboxylate n ²⁰ _D
1.5812 6'-(4-Fluorophenoxy)-2'-pyridylmethyl 2,2,3-trimethyl-3-(3-methylphenoxymethyl)cyclopropanecarboxylate n ²⁰ _D 1.5791 6′-(4-chlorophenoxy)-α′-cyano-
2'-Pyridylmethyl 2,2-dimethyl-3-cyclopentyloxymethylcyclopropanecarboxylate n ²⁰ _D 1.5575 6'-(4-Methylphenoxy)-2'-pyridylmethyl 2,2,3-trimethyl-3-(4-methylcyclohexyloxymethyl)cyclopropanecarboxylate n ²⁰ _D 1.5714 6'-phenoxy-α'-methyl-2'-pyridylmethyl 2,2,3-trimethyl-3-cyclobutylmethyloxycyclopropanecarboxylate
n ²⁰ _D 1.5487 6′-(4-chlorophenoxy)-α′-cyano-
2'-pyridylmethyl 2,2-dimethyl-3-
(4-methylcyclohexylmethyloxymethyl)
Cyclopropane carboxylate n ²⁰ _D 1.5629 6'-(4-fluorophenoxy)-α'-ethynyl-2'-pyridylmethyl 2,2,3-trimethyl-3-isobutoxymethylcyclopropanecarboxylate n ²⁰ _D 1.5496 Insecticide and acaricide of the present invention The compound used as an active ingredient in the agent is a new compound, solid or liquid at room temperature, and generally easily soluble in organic solvents. Therefore, as an insecticide for spraying, it can be used as an emulsion, oil, powder, wettable powder, aerosol, etc.
It can also be mixed with wood flour or other suitable base material and used as an insecticide for fumigation such as mosquito coils.
Also, when used as a so-called electric mosquito repellent, in which the active ingredient is dissolved in an appropriate organic solvent and soaked in a mount, or dissolved in an appropriate solvent and heated and evaporated with an appropriate heating element, it can be used in the same way as a mosquito coil. Shows excellent effects. The compound of the present invention is more stable to light than conventional pyrethroids, has a broader insecticidal spectrum, has low toxicity, and is inexpensive, so it can be used as an agricultural alternative to conventional organophosphorus agents and organochlorine insecticides. Can be used as a horticultural insecticide. The insecticide and acaricide of the present invention can be used for flies,
In addition to sanitary pests such as mosquitoes and cockroaches, organophosphorus and carbamate resistant leafhoppers, planthoppers, stinkbugs, armyworms, diamondback moths, tobacco moths, bean weevils, nocturnal moths, cabbage moths, chestnut beetles, leafhoppers, aphids, and scale insects. It is extremely useful for the control of agricultural pests such as, grain storage pests such as brown elephant, mites, etc.
In addition, the insecticide and acaricide of the present invention include N-octylbicycloheptenedicarboximide (trade name MGK
-264), a mixture of N-octylbicycloheptenedicarboximide and aryl sulfonate (trade name MGK-5026), sinepirin 500, octachlorodipropyl ether, piperonyl butoxide, etc. are added. The insecticidal effect can be further enhanced. In addition to the insecticide and acaricide of the present invention, other insecticides such as fenitrothion,
Organic phosphorus agents such as DDVP, diazinon, propafos, pyridafenethion, NAC, MTMC,
Carbamate agents such as BPMC, PHC, conventional pyrethroid insecticides such as pyrethrin, allethrin, phthalthrin, flamethrin, phenothrin, permethrin, cypermethrin, decamethrin, fuenvalerate, fuenpropanate, cartatu, chlorphenamidine, methomyl, etc. By mixing insecticides, acaricides, fungicides, nematicides, herbicides, plant growth regulators, fertilizers, and other agricultural chemicals, highly effective multipurpose compositions can be obtained, saving labor. , a synergistic effect between the drugs can be fully expected. Next, examples of synthesizing compounds used as active ingredients in the present invention will be shown. The carboxylic acids constituting the compounds of the present invention are, for example, ethers obtained by the methods described in Bull.Soc.Chim.France, 2 , 734 (1966) and J.Chem.Soc., 5225 (1965), and Arch.Pharm. .287 , 129
(1954) using a substituted acrylic ester as a starting material, it can be easily obtained by following the routes shown in step 1 and step 2. Also, the alcohol of general formula () is Chem.Abstr.
80, 59873 and 81 , 13596. The compounds of the present invention can be prepared from acids and alcohols or their reactive derivatives according to general methods for producing esters, and representative examples will be shown below. Other compounds of the present invention show similar trends and can be obtained in good yields by any of the synthetic methods (A), (B), (C), (D), (E), and (F). was completed. Synthesis Example 1 (A) Method by reaction of alcohol and carboxylic acid halide 4.0 g of 2,2,3-trimethyl-3-methoxymethylcyclopropanecarboxylic acid chloride
was dissolved in 15 ml of dry benzene, and 6-phenoxy-α-cyano-2-pyridylmethanol was added to this.
Add 4.6 g dissolved in 20 ml of dry benzene, and then add 3 ml of dry pyridine as a condensation aid to precipitate pyridine hydrochloride. Seal the solution tightly and leave it overnight at room temperature. After separating the crystals of pyridine hydrochloride, dry the benzene solution with sulfuric acid and distill off the benzene under reduced pressure to obtain 6'-phenoxy-α'-cyano-2'-pyridylmethyl 2. , 6.9 g of 2,3-trimethyl-3-methoxymethylcyclopropanecarboxylate were obtained. Synthesis Example 2 (B) Method by reaction of alcohol and carboxylic acid 2,2,3-trimethyl-3-(4-methoxyphenoxy)cyclopropanecarboxylic acid 4.8
g and 4.6 g of 6-phenoxy-α-cyano-2-pyridylmethanol were dissolved in 50 ml of dry benzene, 6.2 g of dicyclohexylcarbodiimide was added, and the mixture was left sealed overnight. The next day, the reaction was completed by heating under reflux for 4 hours, and after cooling, the precipitated dicyclohexyl urea was separated. The oily substance obtained by concentrating the filtrate was passed down a 100 g silica gel column to obtain 6'-phenoxy-α'-cyano-2'-pyridylmethyl 2,2,3-trimethyl-3-(4-methoxyphenyl). 7.5 g of (enoxy)cyclopropane carboxylate were obtained. Synthesis Example 3 (C) Method by reaction of alcohol halide with alkali metal carboxylate 4.8 g of sodium salt of 2,2,3-trimethyl-3-(3-methylcyclobutoxy)cyclopropanecarboxylic acid and 6- Suspend 5.5 g of (4-fluorophenoxy)-α-ethynyl-2-pyridylmethyl chloride in 50 ml of benzene, react under reflux for 3 hours in a nitrogen stream, and then cool the reaction solution to precipitate. After removing the salt by filtration, the salt was thoroughly washed with brine, dried with salt water, and the benzene was distilled off under reduced pressure to obtain 6'-(4-fluorophenoxy)-
α′-ethynyl-2′-pyridylmethyl 2,2,
3-trimethyl-3-(3-methylcyclobutoxy)cyclopropanecarboxylate 7.9g
I got it. Synthesis Example 4 (D) Method by transesterification of alcohol and lower alkyl ester of carboxylic acid Methyl ester of 2,2-dimethyl-3-allyloxymethylcyclopropanecarboxylic acid
4.1 g and 4.3 g of 6-(4-methylphenoxy)-2-pyridylmethanol are heated to 150°C. When the temperature reaches 150°C, add 0.25 g of sodium and start distilling off methanol. When the distillation of methanol has stopped, add another 0.25 g of sodium and increase the temperature to 150 °C until the theoretical amount of methanol is obtained.
Keep the temperature around ℃ and repeat the above operation. The mixture was then cooled, dissolved in ether, and the ether solution was washed with dilute hydrochloric acid, aqueous sodium bicarbonate, and brine, dried over sulfate, and the ether was distilled off under reduced pressure to give 6'-(4
-methylphenoxy)-2'-pyridylmethyl
6.8 g of 2,2-dimethyl-3-allyloxymethylcyclopropanecarboxylate was obtained. Synthesis Example 5 (E) Method by reaction of alcohol and carboxylic acid anhydride 2,2-dimethyl-3-(2-nitro-4-
12.3 g of cyclopropanecarboxylic acid anhydride (chloromethylphenoxymethyl) and 6.0 g of 6-(4-bromophenoxy)-α-methyl-2-pyridylmethanol were dissolved in 50 ml of dry pyridine and stirred overnight at room temperature. . The next day, add 100g of the reaction solution.
of ice water and extracted three times with 20 ml of ether. The ether layers were combined and extracted twice with 20 ml of 5% aqueous sodium hydroxide solution to remove by-produced carboxylic acid. The ether layer was further washed with dilute hydrochloric acid, an aqueous sodium bicarbonate solution, and a saline solution, and then dried over sulfuric acid. The ether was removed under reduced pressure to obtain a crude ester, which was passed down a column containing 20 g of activated alumina to obtain 6'- Bromophenoxy)-α'-methyl-2'-pyridylmethyl 2,2-dimethyl-3
-(2-nitro-4-chloromethylphenoxymethyl)cyclopropanecarboxylate 10.4
I got g. Synthesis Example 6 (F) Method by reaction of alcohol halide and organic tertiary base carboxylate 3.8 g of 2,2,3-trimethyl-3-(isobutoxymethyl)cyclopropanecarboxylic acid is dissolved in 50 ml of acetone. Dissolve and add 5.8 g of 6-(4-fluorophenoxy)-α-ethynyl-2-pyridylmethyl bromide. While stirring, add 4 ml of triethylamine and incubate at 60-80℃ for 30 minutes.
After reacting for an hour, dissolve in ether, wash the ether solution thoroughly with dilute hydrochloric acid, sodium bicarbonate solution, and saline solution.
Dry with salt and remove the ether under reduced pressure.
7.3 g of 6'-(4-fluorophenoxy)-α'-ethynyl-2'-pyridylmethyl 2,2,3-trimethyl-3-(isobutoxymethyl)cyclopropanecarboxylate was obtained. Next, in order to make it clearer that the composition provided by the present invention is excellent, the results of testing the effectiveness will be shown. Test Example 1 Insecticidal test by spraying 0.2% white light solution of the compound of the present invention (A), 0.2% and Cinepirin 500 0.8% white light solution (B), 0.1% and phthalthrin 0.1% white light solution (C), and allethrin The falling and turning rates of houseflies were determined for each 0.2% white light solution of phthalthrin, the relative effectiveness of the test agent was calculated, and the mortality rate after 24 hours was determined as follows. [Table] [Table] Test Example 2 Insecticidal test by fumigation Mosquito coils containing 0.5% of insecticidal ingredients were prepared and tested for their effectiveness in causing adult Culex mosquitoes to fall and roll over. This experiment was published in Insect Control Science Volume 16 (1951).
The relative effectiveness of the incense stick was calculated according to the method of Nagasawa, Katsuta et al., p. 176, and was as follows.
The sample drug number is the same as that of the active ingredient example above. [Table] [Table] Test Example 3 Insecticidal test by microdropping method Control compound phenothrin [3'-phenoxybenzyl 2,2-dimethyl-3-(2,2-dimethylvinyl)cyclopropanecarboxylate] and the present invention Two times the amount of piperonyl butoxide as the active ingredient was added to each of the compounds to make an acetone solution with a predetermined concentration, which was applied to the thoracic dorsal plate of adult house flies using a microsyringe, and death occurred after 24 hours. The insecticidal efficacy relative to the control compound and the synergistic effect of piperonyl butoxide were investigated based on the insect percentage, and the results were as follows. [Table] Examples of formulations are shown below, and formulations can be prepared by methods well known to those skilled in the art without requiring any special conditions in accordance with general agricultural chemicals. Reference example 1 White kerosene was added to 0.2 parts of the present compound (1) and the whole
Obtain 0.2% oil solution as 100 parts. Reference Example 2 White kerosene is added to 0.2 parts of the compound of the present invention (2) and 0.8 parts of piperonyl butoxide to make a total of 100 parts to obtain an oil agent. Reference Example 3 To 20 parts of the compound of the present invention (7), 10 parts of Solpol SM-200 (registered trademark of Toho Chemical) and 70 parts of xylol were added and mixed and dissolved with stirring to obtain a 20% emulsion. Reference example 4 Compound of the present invention (16) 0.4 parts, resmethrin 0.1
1 part, 1.5 parts of octachlorodipropyl ether is dissolved in 28 parts of refined kerosene, and the solution is filled into an aerosol container.
After installing the valve part, 70 parts of propellant (liquefied petroleum gas) is pressurized and filled through the valve part to obtain an aerosol. Reference Example 5 0.5 g of the present compound (20) and 0.5 g of BHT were added to base materials for mosquito coils such as pyrethrum extract lees powder, wood flour, and starch powder.
Mix 99.0g of the mixture uniformly and obtain a mosquito coil by a known method. Reference example 6 Compound of the present invention (24) 0.4g, MGK-5026 1.0g
was uniformly mixed with 98.6 g of a mosquito coil base material to obtain a mosquito coil by a known method. Reference Example 7 0.3 parts of the compound of the present invention (27) and 99.7 parts of clay are thoroughly ground and mixed to obtain a 0.3% powder. Reference Example 8 40 parts of the present compound (32), 35 parts of diatomaceous earth, clay
20 parts of lauryl sulfonate, 3 parts of lauryl sulfonate, and 2 parts of carboxymethyl cellulose are ground and mixed to obtain a hydrate. Test Example 4 5 to 5 on a surface where a large number of green peach aphids appeared
Among the emulsions obtained in Reference Example 3 in a radish field at the 6-leaf stage, compounds of the present invention (2), (7), (8), (13), (18),
A 1000-fold diluted solution of each emulsion containing (24), (30) and (35) with water was sprayed at 100 times per area.
Two days later, the parasitism rate was investigated and found that the density had decreased to less than 1/10 of the pre-spraying density in each plot. Test Example 5 Among the emulsions obtained in Reference Example 3, the compound of the present invention
(1), (4), (7), (9), (16), (19), (25), (29)
Fresh leaves were immersed in a 2000-fold dilution of (33) for about 5 seconds, and after drying, they were placed in a shear dish and 10 healthy armyworm larvae were released. The test insects were released twice, once on the day of dipping the fresh leaves, and once for 5 days, and the mortality rate was determined 24 hours later. [Table] [Table] [Table] Control drug () Compound disclosed in U.S. Patent No. 4,238,614 [6'-phenoxy-α'-cyano-2'-pyridylmethyl 2,2-dimethyl-3-(2-cyano-4
-Methylcarbonylphenoxy)cyclopropanecarboxylate] As a result of the test, the drug of the present invention was superior to commercially available salithion emulsions and control drugs in terms of both insecticidal efficacy and residual efficacy. Test Example 6 One day before applying the insecticidal ingredient to potted fava beans, one tree was infested with approximately 200 aphids. Among the hydrating agents obtained in Reference Example 8, (1)
(6), (10), (14), (21), (26), (28), (32)
A 4000-fold diluted solution of (34) was sprayed onto leaves infested with insects using a compressed air spray method (10 ml/pot), and the degree of damage was observed 2 days later. As a result, no increase in the degree of damage was observed in any of the cases. Test Example 7 (5), (10), (12), (17) obtained by Reference Example 7
,
(22), (27) and (31) each with a diameter of 14 mm.
Spread butter evenly at a rate of 2 g/m ² on the bottom of a waist-high glass cholera, and apply butter to the wall, leaving about 1 cm at the bottom. There was one adult German cockroach in it.
If the cockroaches were released in groups of 10 and left in contact for 30 minutes before being transferred to a new container, more than 80% of the cockroaches could be killed by either powder after three days. Test Example 8 1 for 4 leaves of potted green beans 5 days after sowing
Infested with 10 female adult spider mites per leaf.
Store in a constant temperature room at 27℃. After 6 days, a chemical solution prepared by diluting emulsions (3), (7), (11), (15), (20), (23) and (33) obtained in Reference Example 3 with water to 100 ppm of active ingredient was turned. 10 ml of the solution was sprayed per pot on a table, and the number of parasitic spider mites on the plants was investigated 10 days later.
As a result, all of the drugs of the present invention were found to have acaricidal effects superior to the control drugs. [Table] Control drugs () [3'-phenoxy-α'-cyanobenzyl 2,2
-dimethyl-3-isobutoxycyclopropanecarboxylate] Comparative drug () Compound disclosed in U.S. Pat. No. 4,238,614 [6'-phenoxy-2'-pyridylmethyl 2,2
-Dimethyl-3-phenoxycyclopropanecarboxylate] Test Example 9 Carp was used as a control, and the compound of the present invention was tested in accordance with the Fish Toxicity Test Method No. 2735 (November 25, 1966), Notification of Agricultural Policy. (7), (9), (14),
When the TLm48 (ppm) of (18), (22) and (30) was determined, it was 0.8 or more in all cases.

Claims (1)

[Claims] 1. General formula (In the formula, l is 0 or 1, and R ₁ represents a hydrogen atom or a methyl group. However, when l is 0, R ₁
represents only a methyl group. R ₂ is an alkyl group having 1 to 6 carbon atoms, 3 carbon atoms
-5 alkenyl group, C3-5 alkynyl group, C1-3 haloalkyl group, C2-C2
4 haloalkenyl group and formula (), (), ()
The group represented by is shown below. [Formula] [Formula] [Formula] Here, R ₅ and R ₆ are a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a methoxy group, a methylthio group, a halomethyl group, a halomethoxy group, a nitro group, or R ₅ , R ₆ represents a methylenedioxy group. Moreover, m and n are integers of 2 to 5, and R ₇ and R ₈ represent a hydrogen atom or a methyl group. R ₃ represents a hydrogen atom, a cyano group, an ethynyl group, or a methyl group, and R ₄ represents a hydrogen atom, a halogen atom, or a methyl group. ) An insecticide and acaricide characterized by containing a cyclopropanecarboxylic acid ester derivative represented by: