JPS6049193B2 - Cyclopropanecarboxylic acid ester derivatives, methods for producing cyclopropanecarboxylic acid ester derivatives, insecticides containing cyclopropanecarboxylic acid ester derivatives - Google Patents

Description

Detailed Description of the Invention The present invention is based on the general formula (where n represents an integer of 1 to 6, m represents an integer of 1 to 2, and R represents the general formula (■), (■), (■), (■) or (■
) represents a group represented by

Here, x represents an oxygen atom or a (-CH=CH-) group, and R1 represents an allyl group, a propargyl group, a benzyl group,
It represents a phenoxyl group, a phenylthio group, or a 2,2 dichlorovinyloxyl group, and R2 represents a hydrogen atom, a methyl group, or a halogen atom.

t is an integer of 1 to 2, and R3 represents a hydrogen atom, a cyano group, or an ethynyl group. R4 represents a phthalimide group, a tetrahydrophthalimide group or a dialkylmaleimide group. R5 represents an allyl group, a propargyl group or an alkadienyl group. Y is a methyl group or a halogen atom, R6
represents a phenyl group or a furyl group. Z represents a methylene group or an oxygen atom, R7 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group or a halogen atom, and I represents an integer of 1 to 2. ), its optical and geometric isomers, its production method, and an insecticide characterized by containing this compound as an active ingredient. Although various alcohol components of chrysanthemum acid esters have been studied and put into practical use, their use outdoors has been restricted because they are susceptible to oxidative decomposition by light. Recently, research into acid components has become active, and a compound that is more stable to light than conventional pyrethroids by replacing the methyl group with a halogen atom has been discovered. However, when considering issues such as environmental pollution and chronic toxicity, compounds with structures similar to naturally occurring organic compounds, mainly consisting of carbon, water, FO, oxygen, and nitrogen, are considered to be advantageous as future insecticidal ingredients. Conceivable. As a result of repeated research, the inventor has found the above formula (1), (■
) has an extremely excellent insecticidal effect on various sanitary pests and agricultural and horticultural pests as an insecticidal ingredient,
We learned that it has extremely low toxicity to warm-blooded animals and is much more stable against light than conventional pyrethroids. In this way, the compounds represented by formulas (1) and (n) above overcome the drawback of conventional pyrethroids, such as being unstable to light, and are excellent pest control compositions that have a wide insecticidal spectrum and low toxicity. Moreover, the cyclopropanecarboxylic acids constituting the above formulas (1) and (n) can be easily obtained at low cost.

The present invention was completed based on the above findings.
The compounds represented by the above formulas (1) and (H) used as active ingredients in the present invention are prepared according to the general method for producing esters according to the general formula (where n is an integer of 1 to 6 and m is an integer of 1 to 2). represents.

) or its reactive derivative represented by the general formula R-0H...(X) (wherein R is the general formula (111), (IV), (V), (
VI) or (V[I).

here\Rl9R29R39ROR59R69R7
9X9Y, Z, t, l represent the same meanings as above. ) or a reactive derivative thereof.

Examples of reactive derivatives of carboxylic acids include acid halides, acid anhydrides, lower alkyl esters, and alkali metal salts. Examples of reactive derivatives of alcohol include chloride. The reaction is carried out in a suitable solvent, optionally in the presence of an organic or inorganic base or acid as a deoxidizing agent or catalyst, and optionally with heating. Representative examples of the compounds represented by the above formulas (1) and (n) are as follows, but the present invention is of course not limited to these. 3'-phenoxy a-cyanobenzyl 2,2-dimethyl-3-(oxetane-2-ynole)-cyclopropanecarboxylate NROl. 563
85'-benzyl-3'-furylmethyl 2,2-dimethyl-3-(oxetan-2-yl)-cyclopropanecarboxylate NROl. 55247゜-Methyl-2゜,3゜-dihydrobenzofuran-3゛-yl 2,
2-dimethyl-3-(oxetane-2-yl)-cyclopropanecarboxylate NgOl. 55O73'-Phenoxya'-cyanobenzyl 2,2-dimethyl-3-(oxiran-2-yl)-cyclopropanecarboxylate NHOl. 548O5'-propargyl-2'-furylmethyl-2,2-dimethyl-3-(oxirane-2-yl)cyclopropanecarboxylate NgOl. 54l63゛-Phenoxya゛-cyanobenzyl 2,2-dimethyl-3-(oxetane-3
-yl) monocyclopropanecarboxylate NgOl.
56443゛-(2,2dichlorovinyloxy)benzyl 2,2-dimethyl-3-(oxetan-3-yl)
-Cyclopropanecarboxylate n 1.5536 5'-propargyl-2' -furylmethyl-2,2-dimethyl-3-(oxetan-2-yl)-cyclopropanecarboxylate NZOl. 54733゛,4゛,5゛,6゛-Tetrahydrophthalimidomethyl 2,2
-dimethyl-3-(oxetan-21-yl)-cyclopropanecarboxylate NKOl. 549O2'-aryl-3'-methyl 2'-cyclopenten-1'-one-4'-yl 2,2-dimethyl-3-,(oxetane-2-yl)-cyclopropanecarboxylate NROl
．． 55O53'-phenoxylbenzyl 2,2-dimethyl-3-(oxirane-2-yl)-cyclopropyl,
Carboxylate NgOl. 54384'-Phenyl-3'-methyl-2'-buten-1-yl 2,2-dimethyl-3-(oxirane-2,oxy-inole)-cyclopropanecanoleboxylate NKOl. 53967゛-
Allylindan-3゜-yl2,2-dimethyl-3
-(oxiran-2-yl)-cyclopropanecarboxylate NROl. 54583'', 4', 5', 6'-tetrahydrophthalimidomethyl 2,2-dimethyl-3-(oxirane-2'-yl)-cyclopropanecarboxylate NLO1.543O5'-benzyl-3
'-furylmethyl2,2-dimethyl-3-(oxetan-3-yl)-cyclo. ^Propane carboxylate N
BOL. 55357゛-Methyl-2゛,3'-dihydrobenzofuran-3゜-yl2,2-dimethyl-3-(
oxetan-3-yl)-cyclopropanecarboxylate n votes 1.55142゛-aryl-3゛-methyl-2
゛-Cyclopentene-1゛-one-4゛-yl 2,2-
Dimethyl-3-(oxetane-3-ynole)-cyclopropanecanoleboxylate n 1.5527-phenoxy-a '1-ethynylbenzyl 2,2-dimethyl-3-(oxolan-2-yl)-cyclopropanecarboxylate NROl ．． 5677 4-Friru 3″-chloro7-buten-1″-yl 2
,2-dimethyl-3-(oxolane-3-monyl)-cyclopropanecarboxylate
Tf).

1.5642 dimethylmaleimidomethyl 2,2-dimethyl-3-(oxan-2-yl)-cyclopropanecarboxylate n 01.56215″
-aryl2''-methyl-3''-furylmethyl2,2-
Dimethyl-3-(oxan-3-yl)-cyclopropanecarboxylate NLOl. 55892″,6″-dichloro4″-phenylthioα″monoethynylbenzyl 2,2-dimethyl-3-(oxan-4-yl)-cyclopropanecarboxylate
n? 01.5735 Phthalimidomethyl 2,2
-Dimethyl-3-(oxolan-2-yl)-cyclopropanecarboxylate nBa01
．． 55602゛-(24-pentadienyl)3゛-methyl-2゜-cyclopenten-1゛-one-4゛-yl 2
,2-.

゜Dimethyl-3-(oxolan-2-yl)-cyclopropanecarboxylate NgOl. 55935゛,7
'-Dichloroindan-3'-yl 2,2-dimethyl-3-(oxolan-3-yl)-cyclopropanecarboxylate 01.56022'-Propargyl-3'-methyl-2'-cyclopenten-1'-one-4 -yl2,2-dimethyl-3-(oxane-4
-yl)-cyclopropanecarboxylate NgOl.
56l53'-Phenoxybenzyl 2,2-dimethyl-3-(oxetan-2-yl)-cyclopropane carboxylate NUOl. 55985゛-benjiru 3゛-
Furylmethyl 2,2-dimethyl-3-(oxiran-2-yl)-cyclopropanecarboxylate NgOl
．． 54773″-Phenoxybenzyl 2,2-dimethyl-3-(oxetan-3-yl)-cyclopropanecarboxylate nBa01.56015′
-Propargyl-2'-furylmethyl 2,2-dimethyl-3-(oxetan-2-yl)-(chloropropanecarboxylate) n 01.54853'', 4'', 5
″,6″-tetrahydrophthalimidomethyl 2,2-dimethyl-3-(oxetan-3★-yl)-cyclopropanecarboxylate
NLOL. 54972''-aryl-3''-methyl-2'-cyclopentene-1''-one-4''-yl2,2-dimethyl-3-~(oxirane-2-yl)-
Cyclopropane carboxylate
n? 01.54534″-phenyl-3′-methyl-7
-butene-1″-yl 2,2-dimethyl-3-(oxetane-2,L-yl)-cyclopropanecarboxylate
n milk 01.547
23″-(2,2 dichlorovinyloxy)-α5-cyanobenzyl 2,2-dimethyl-3-(oxetane-2-
yl)-cyclopropanecarboxylate 3゛-phenoxyaゝ-cyanobenzyl 2,2-dimethyl-3
-(oxolan-2-yl)-, *cyclopropanecarboxylate NUOl. 56842ゝ-methyl-4'
-Benzyl a゛-ethynylbenzyl 2,2-dimethyl-3-(oxane-2](-yl)-cyclopropanecarboxylate NgOl.57653゛-phenoxya゛-cyanobenzyl 2,2-dimethyl-3-(oxolane-3- 1.5691 The compound of the present invention is a novel compound, which is solid or liquid at room temperature and is generally easily soluble in organic solvents.

Therefore, it can be used as an insecticide for spraying as an emulsion, oil, ice 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. I can do it. In addition, when using the active ingredient 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, and has a broader insecticidal spectrum.
Since it has low toxicity and is inexpensive, it can be used as an agricultural and horticultural insecticide in place of conventional organic phosphorus agents and organic chlorine insecticides. In addition, N-octylbicycloheptenedicarboximide (trade name M
GK-264), a mixture of N-octylbicycloheptenedicarboximide and aryl sulfonate (trade name MGK-5026), cinepirin 50s octachlorodipropyl ether, piperonyl butoxide, and other synergists are added. and its insecticidal effect can be further enhanced.

The compounds of the present invention may also be used with other insecticides such as Sumithion, D.
DVP, organic phosphorus agents such as diazinon, carbamate agents such as 1-naphthyl-N-methyl carbamate, 3,4-dimethylphenyl-N-methyl carbamate, pyrethrin, allethrin, phthalthrin, flamethrin, phenotrin, permethrin, cypermethrin, decamethrin, Conventional pyrethroid insecticides such as fuenvalerate and fuenpropanate, insecticides such as pattern, galecuron, and raninate, or miticides, fungicides, nematicides, herbicides, plant growth regulators, fertilizers, etc. By mixing these pesticides, a multipurpose composition with excellent efficacy can be obtained, and labor savings and synergistic effects between the drugs can be fully expected. In order to make it clearer that the composition provided by the present invention is excellent, the results of the efficacy test are shown below. Test Example 1 Insecticidal test by spraying 0.2% of the compound of the present invention of Compound Example 31 in a white light solution (B), 0.2% and piperonyl butoxide 0.8% in a white light solution (B); The falling and turning rates of house flies were determined for a white light solution (C) of 1% and 0.1% phthalthrin, and a white light solution of 0.2% each of allethrin and phthalthrin, and the relative effectiveness of the test drug was calculated. Furthermore, the mortality rate after two servings was determined as follows.

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 carried out in Insect Control Science 1-(1951), p. 176. The relative effectiveness of the incense sticks was calculated according to the method of Nagasawa, Katsuta et al., and the results were as follows. The test drug number is the same as that of the active ingredient drug. Test Example 3 Insecticidal test by microdropping method Allethrin and the compound of the present invention were added with piperonyl butoxide in an amount twice the amount of the active ingredient, respectively, to make an acetone solution of a predetermined concentration, which was then used to inject adult houseflies using a microsyringe. The relative insecticidal efficacy against allethrin and the synergistic effect with piperonyl butoxide were investigated based on the mortality rate after 2 hours, and the results were as follows.

Next, examples will be shown for representative examples, but other compounds of the present invention also show similar trends. The compound names are the same as those in the active ingredient examples above. Example 1 3.7 g of 2,2-dimethyl-3-(oxetan-2-yl)-cyclopropanecarboxylic acid is dissolved in 50 ml of dimethylformamide, and 5.1 g of 3-phenoxy α-cyanobenzyl chloride is added thereto.

Add 4 ml of triethylamine while stirring, react at 60-80°C for 3 hours, and then dissolve in ether. The ether solution was thoroughly washed with dilute hydrochloric acid, aqueous sodium bicarbonate, and brine, dried over sulfur, and the ether was distilled off under reduced pressure. Te3″-Phenoxy α5-
6.7 g of cyanobenzyl 2,2-dimethyl-3-(oxetan-2-yl)-cyclopropanecarboxylate
I got it. Example 2 2.8 g of 2,2-dimethyl-3-(oxirane-2-yl)-cyclopropanecarboxylic acid and 3
,4,5,6-tetrahydrophthalimidomethylol 3
．． 7g and dissolved in 50ml of dry benzene, 6.0g
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 filtered off. The oily substance obtained by concentrating the filtrate was passed down a 100 g silica gel column to obtain 3″,4″,5″,6″-tetrahydrophthalimidomethyl 2,2-dimethyl-3-(oxirane-2-yl)-cyclopropane. 4.3 g of carboxylate was obtained. Example 3 2,2-dimethyl-3-(oxetane-3-
3. Sodium salt of cyclopropanecarboxylic acid)
9 g and 4.5 g of 3-phenoxybenzyl chloride were dissolved in 50 ml of benzene and reacted under reflux for 3 hours under a nitrogen stream. The reaction solution was then cooled and the precipitated salt was separated in the furnace. After thorough washing with brine, The residue was dried over nitrogen and benzene was distilled off under reduced pressure to obtain 6.7 g of 3-phenoxybenzyl 2,2-dimethyl-3-(oxetan-3-yl)-cyclopropanecarboxylate.

Example 4 3.8 g of 2,2-dimethyl-3-(oxetan-2-yl)-cyclopropanecarboxylic acid chloride was dissolved in 15 ml of dry benzene, and 3.7 g of 5-benzy-3-furyl methyl alcohol was dissolved in 20 ml of dry benzene. When 3 ml of dry pyridine is added as a condensation aid, crystals of pyridine hydrochloride are precipitated.

After sealing the cap and leaving it at room temperature overnight, the crystals of pyridine hydrochloride were separated, the benzene solution was dried with sulfuric acid, and the benzene was distilled off under reduced pressure to obtain 5''-benzyl-3''-furylmethyl 2.
, 6.2 g of 2-dimethyl-3-(oxetan-2-yl)-cyclopropanecarboxylate were obtained. Example 5
Methyl ester of 2,2-dimethyl-3-(oxolan-3-yl)-cyclopropanecarboxylic acid 3. ? and 5
, 4.1 g of 7-dichloroindan-3-ol to 150
Heat to ℃. When the temperature reaches 150° C., 0.25 g of sodium is added and methanol distillation is started. When the distillation of methanol has stopped, 0.25 g of sodium is further added to obtain the theoretical amount of methanol.The above operation is repeated while keeping the temperature at around 150°C. The mixture was then cooled and dissolved in ether, and the ether solution was washed with dilute hydrochloric acid, aqueous sodium bicarbonate, and brine, dried over sulfur, and the ether was distilled off under reduced pressure to give 5',7'-dichloroindan-3'-yl 2. ,2-
6.2 g of dimethyl-3-(oxolan-3-yl)-cyclopropanecarboxylate were obtained. Example 6 5.3 g of 2,2-dimethyl-3-(oxirane-2-yl)-cyclopropanecarboxylic acid anhydride and 3.2 g of 4-phenyl-3-methyl-2-buten-1-ol were added to
It was dissolved in 0ml of dry pyridine and stirred overnight at room temperature.

The next day, the reaction solution was poured into 100 g of ice water, and 20 m of ether was added.
1 was used for extraction three times. The ether layers were combined and extracted twice with 30 mL of a 5% aqueous sodium hydroxide solution to remove by-produced carboxylic acid. The ether layer is further diluted with hydrochloric acid,
After washing with aqueous sodium bicarbonate and saturated saline, drying with sodium chloride and removing ether under reduced pressure, crude ester was obtained, and activated alumina 20
g column to obtain 4.7 g of 4''-phenyl-3''-methyl-2''-buten-1''-yl 2,2-dimethyl-3-(oxirane-2-yl)-cyclopropanecarboxylate. Reference Example 1 White kerosene was added to 0.2 parts of the compound (1) of the present invention, and the total amount was 1 part.
A 0.2% oil solution is obtained as 0C5.

Reference Example 2 White kerosene is added to 0.2 part of the compound (2) of the present invention and 0.8 part of piperonyl butoxide to make a total of 1 (1) part to obtain an oil solution.

Reference Example 3 Compound (4) of the present invention 2Cif1, Solpol SM-2
Part W of 00 (registered trademark of Toho Chemical) and m part of xylene were added and mixed and dissolved with stirring to obtain a 20% emulsion.

Reference example 4 0.4 part of the present compound (6), 0.1 part of resmethrin,
Refined 1.5 parts of octachlorodipropyl ether to 2 parts of kerosene
Aerosol 3 is obtained by dissolving 8 parts of the aerosol into a Niazol container and attaching a valve part, and then filling m parts of a propellant (liquefied petroleum gas) under pressure through the valve part.

Reference Example 5 Compound of the present invention AOO. 5y. ．． BHTO. 5y is a base material for mosquito coils such as pyrethrum extracted lees powder, wood flour, starch powder, etc. 99.0
y to obtain a mosquito coil by a known method.

Reference Example 6 Compound (19) of the present invention 0.4y. ．． MGK-50261
．． Of is uniformly mixed with 98.6 g of a mosquito coil base material to obtain a mosquito coil by a known method.

Reference Example 7 3 parts of the compound (25) of the present invention and 97 parts of clay were thoroughly ground and mixed to obtain a 3% powder.

Reference Example 8 Compound of the present invention (35) Kube, 35 parts of diatomaceous earth, 2 parts of clay
A wettable powder is obtained by pulverizing and mixing 3 parts of lauryl sulfonate and 2 parts of carboxymethyl cellulose.

Test Example 4 Compounds (1), (2), (4), ( 7), (12), (1
6), (21), (23), (27), (32) and (36), each of which was diluted 1000 times with water, was sprayed at 100 e/per plate.

A parasitic rate survey two days later showed that the density had decreased to 1,110 or less than the pre-spraying density in each plot.

Among the emulsions obtained in Test Example 5 Reference Column 3, the compound of the present invention (
1), (4), (9), (13), (18), (26)
, (30) and (37), fresh leaves were immersed in the 200@ diluted solution for about 5 seconds, and after the solution had dried, they were placed in a shear dish and 10 healthy larvae of armyworm were released.

The test insects were released by soaking them in fresh leaves. The test was carried out twice 5 days later to determine the mortality rate after 24B1. Test Example 6 One day before applying the insecticidal active ingredient to potted fava beans, one tree was infested with about 200 aphids.

Among the hydrating agents obtained in Reference Example 8, (2) and (5)
, (6), (8), (13), (17), (22), (
25), (31), and 4000-fold dilutions of (35) were sprayed on leaves infested with insects using a compressed air spray method per 10 mt/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 (1), (3), (6), (
12), (20), (25), (28), (33), and (36) were uniformly sprinkled on the bottom of the lasschaare with a waist height of 14 cTn at a rate of 2 g/d, and the bottom was coated with about 1 CrfL. Leave some butter on the wall.

Claims (1)

[Claims] 1. General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I),▲
There are mathematical formulas, chemical formulas, tables, etc.▼...(II) (in the formula,
n represents an integer of 1 to 6, m represents an integer of 1 to 2, and R represents a group represented by general formula (III), (IV), (V), (VI) or (VII). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(III), R
＿４－CH＿２－・・・(IV)▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・(V),▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・(VI)▲Mathematical formulas, chemical formulas, tables, etc. There is▼
...(VII), where X is an oxygen atom or (-CH=C
H-) group, R_1 represents an allyl group, propargyl group, benzyl group, phenoxyl group, phenylthio group, or 2,2 dichlorovinyloxyl group, and R_2 represents a hydrogen atom, a methyl group, or a halogen atom. t is an integer of 1 to 2, and R_3 represents a hydrogen atom, a cyano group, or an ethynyl group. R_4 represents a phthalimide group, a tetrahydrophthalimide group or a dialkylmaleimide group. R_5 represents an allyl group, a propargyl group, or an alkadienyl group. Y is a methyl group or a halogen atom, and R_6 represents a phenyl group or a furyl group. Z is a methylene group or an oxygen atom, R_7 is a hydrogen atom, a lower alkyl group, a lower alkenyl group, or a halogen atom, and l is 1 to 2
represents an integer. ) and its optical and geometric isomers.
2. The compound according to claim 1, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 3. The compound according to claim 1, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 4. The compound according to claim 1, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 5. The compound according to claim 1, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 6. The compound according to claim 1, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 7. The compound according to claim 1, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 8. The compound according to claim 1, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 9 General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ... (VIII) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ... (IX) (In the formula, n
represents an integer of 1 to 6, and m represents an integer of 1 to 2. ) or its reactive derivative represented by the general formula R-OH...(X) (wherein R is the general formula (III), (IV), (V), (VI)
or a group represented by (VII). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(III), R
＿４－CH＿２－・・・・・・(IV)▲Mathematical formula, chemical formula,
There are tables, etc.▼...(V)▲There are mathematical formulas, chemical formulas, tables, etc.▼...(VI)▲There are mathematical formulas, chemical formulas, tables, etc.▼...(VII), where X is an oxygen atom or (-CH
=CH-) group, R_1 represents an allyl group, propargyl group, benzyl group, phenoxyl group, phenylthio group, or 2,2 dichlorovinyloxyl group; R_2
represents a hydrogen atom, a methyl group or a halogen atom. t is an integer of 1 to 2, and R_3 represents a hydrogen atom, a cyano group, or an ethynyl group. R_4 represents a phthalimide group, a tetrahydrophthalimide group or a dialkylmaleimide group. R_5 represents an allyl group, a propargyl group, or an alkadienyl group. Y is a methyl group or a halogen atom, and R_6 represents a phenyl group or a furyl group. Z is a methylene group or an oxygen atom, R_7 is a hydrogen atom, lower alkyl group, lower alkenyl group, or halogen atom, l is 1
Represents an integer between ~2. ) The general formula ▲ is characterized by reacting with an alcohol or its reactive derivative represented by
There are mathematical formulas, chemical formulas, tables, etc. ▼...(I), ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) (here n
, m, and R have the same meanings as above. ) A method for producing a cyclopropanecarboxylic acid ester derivative. 10 General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・(I),▲
There are mathematical formulas, chemical formulas, tables, etc.▼...(II) (in the formula,
n represents an integer of 1 to 6, m represents an integer of 1 to 2, and R represents a group represented by general formula (III), (IV), (V), (VI) or (VII). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(III), R
＿４－CH＿２－・・・・・・(IV) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・(V)▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・(VI)▲Mathematical formulas, chemical formulas, There are tables, etc.▼...(VII), where X represents an oxygen atom or (-CH=CH-) group, and R_1 is an allyl group, propargyl group, benzyl group, phenoxyl group, phenylthio group, or 2, 2 represents a dichlorovinyloxyl group, and R_2 represents a hydrogen atom, a methyl group, or a halogen atom. t is an integer of 1 to 2, and R_3 represents a hydrogen atom, a cyano group, or an ethynyl group. R_4 represents a phthalimide group, a tetrahydrophthalimide group or a dialkylmaleimide group. R_5 represents an allyl group, a propargyl group, or an alkadienyl group. Y is a methyl group or a halogen atom, and R_6 represents a phenyl group or a furyl group. Z is a methylene group or an oxygen atom, R_7 is a hydrogen atom, lower alkyl group, lower alkenyl group, or halogen atom, l is 1
Represents an integer between ~2. ) An insecticide characterized by containing a cyclopropanecarboxylic acid ester derivative represented by: 11. The insecticide according to claim 10, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 12. The insecticide according to claim 10, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 13. The insecticide according to claim 10, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 14. The insecticide according to claim 10, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 15. The insecticide according to claim 10, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 16. The insecticide according to claim 10, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 17. The insecticide according to claim 10, which is a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. 18. The insecticide according to claim 10, which contains a pyrethroid synergist as an adjuvant.