JPS6237031B2 - - Google Patents

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention relates to a novel acetic acid derivative, a method for producing the same, and an insecticide containing the acetic acid derivative as an active ingredient. [Prior art and problems to be solved by the invention] Conventionally, various alcohol components of cyclopropane carboxylic acid esters used as active ingredients of insecticides have been studied and put into practical use. As for the acid component, there is no one that has been put to practical use yet. [Means for solving the problem] As a result of repeated research, the inventor has developed the following formula ()
It has been found that the compound represented by the following has an extremely excellent insecticidal effect on various sanitary pests and agricultural and horticultural pests as an insecticidal ingredient, while its toxicity to warm-blooded animals is extremely low. The present invention was completed based on the above findings. That is, the acetic acid derivative of the present invention has the general formula (): [In the formula, m represents an integer of 1 to 4, R ₁ represents a lower alkyl group, a lower alkoxy group, or a halogen atom, provided, however, that it contains at least one lower alkoxy group, and R ₂ represents a lower alkyl group. , represents a lower alkenyl group, lower alkoxy group, lower haloalkyl group or lower haloalkenyl group, and R ₃ is the following general formula (), () or ():

[Examples and effects of the invention]

Examples of the present invention will be shown below. The compound names are the same as those in the active ingredient examples above. Synthesis example α-isopropyl-(p-methoxyanilino)
Dissolve 4.8 g of acetic acid chloride in 15 ml of dry benzene, and add m-phenoxybenzyl alcohol to this.
Add 4.2 g dissolved in 20 ml of dry benzene, and then add 3 ml of dry pyridine as a condensation aid to precipitate crystals of pyridine hydrochloride. After sealing and leaving overnight at room temperature, remove the pyridine hydrochloride, dry the benzene solution with nitric acid, and concentrate at low temperature (bath temperature below 50°C) in a nitrogen stream under reduced pressure.
m'-Phenoxybenzyl-α-isopropyl-
7.2 g of (p-methoxyanilino)acetate [compound (1)] was obtained. Compounds (2) to (10) were obtained in the same manner. Formulation example Add white kerosene to 0.2 parts of the compound of the present invention (1) and mix
Obtain 0.2% oil solution as 100 parts. Next, the insecticidal test results of the carboxylic acid ester will be shown. Test Example 1 (Test by Spraying) White light solution containing 0.2% of the active ingredients of the 10 above-mentioned compound examples
(A), a white lamp solution containing 0.2% of the active ingredient and 0.8% piperonyl butoxide (B), a white kerosene solution containing 0.1% of the active ingredient and 0.1% phthalthrin (C), and allethrin,
For each 0.2% white light solution of phthalthrin, the fall inhibition rate of house flies was determined using the spray drop method using house flies, and the relative effectiveness of the test chemicals was calculated.
The mortality rate after 24 hours was determined as shown in Table 1 below.

[Table] Test Example 2 (Test using fumigation) Mosquito coils containing 0.5% of insecticidal ingredients were prepared and tested for their effectiveness in making adult Culex mosquitoes fall and fall upside down. This experiment was published in Insect Control Science Volume 16 (1951)
Page 176: The relative effectiveness of the incense sticks was calculated according to the method of Nagasawa, Katsuta, et al., as shown in Table 2 below. The test drug number is the same as that of the active ingredient example above.

【table】

[Table] Test Example 3 Ten 3rd instar larvae of Spodoptera japonica were placed in a tall glass jar with a diameter of 14 cm, and 20% of the compound of the present invention was added to the spray tower.
Solpol SM-200 (Toho Chemical registered trademark name)
Add 10 parts and 70 parts of xylene and stir to dissolve.
Spray 1 ml of a 200-fold dilution with water of the emulsion containing the compound of the present invention (7) obtained by making it into a 20% emulsion, transfer it to a waist-high tray containing feed, and let it stand. After two days, we were able to kill more than 80% of the armyworms. Test Example 4 5 to 5 on a surface where a large number of green peach aphids appeared
Add Solpol to 20 parts of the compound of the present invention in a radish field at the 6-leaf stage.
Compound (6) of the present invention was obtained from an emulsion obtained by adding 10 parts of SM-200 (registered trademark of Toho Chemical) and 70 parts of xylene and stirring and dissolving to obtain a 20% emulsion.
A 200-fold diluted solution of each emulsion containing (9) and (9) with water was sprayed 100 times per square. 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 Rice was grown 45 days after sowing in a 1:50,000 Wagner pot, and 40 parts of the compound of the present invention and diatomaceous earth were grown.
35 parts, 20 parts of clay, 3 parts of lauryl sulfonate,
Among the wettable powders obtained by grinding and mixing 2 parts of carboxymethyl cellulose to form a wettable powder, the water of each wettable powder containing the compounds (2), (3), and (4) of the present invention Spray a 400-fold dilution of the solution at a rate of 100ml/pot. By covering it with a cylindrical wire mesh and releasing about 20 adult brown planthoppers into it, we were able to kill more than 80% of the insects within one day.

Claims (1)

[Claims] 1 General formula (): [In the formula, m represents an integer of 1 to 4, R ₁ represents a lower alkyl group, a lower alkoxy group, or a halogen atom, provided, however, that it contains at least one lower alkoxy group, and R ₂ represents a lower alkyl group. , represents a lower alkenyl group, lower alkoxy group, lower haloalkyl group or lower haloalkenyl group, R ₃ is the following general formula (), () or (): [Formula] R ₇ −CH ₂ − () (In the formula, R ₄ is a hydrogen atom, an allyl group, a propargyl group,
It represents a benzyl group, thenyl group, furylmethyl group, phenoxy group or phenylthio group, and R ₅ represents a hydrogen atom or a methyl group, or adjacent R ₄ and R ₅ or R ₅ are bonded together at the terminals. forms a tetramethylene chain, t represents an integer of 1 or 2, R ₆ represents a hydrogen atom, an ethynyl group or a nitrile group, and Y represents an oxygen atom, a sulfur atom or -CH=CH-
represents a group, R ₇ is a phthalimide group, a thiophthalimide group,
an acetic acid derivative represented by the following formula: a di- or tetrahydrophthalimide group or a dialkylmaleimide group, R ₁₀ represents a thienyl group or a furyl group, and Z represents a methyl group. 2 General formula (): [In the formula, m represents an integer of 1 to 4, R ₁ represents a lower alkyl group, a lower alkoxy group, or a halogen atom, provided, however, that it contains at least one lower alkoxy group, and R ₂ represents a lower alkyl group. , a lower alkenyl group, a lower alkoxy group, a lower haloalkyl group, or a lower haloalkenyl group] or a reactive derivative thereof, and a carboxylic acid represented by the general formula (): R ₃ −OH () [wherein R ₃ is The following general formula (), () or (): [Formula] R ₇ −CH ₂ − () (In the formula, R ₄ is a hydrogen atom, an allyl group, a propargyl group,
It represents a benzyl group, thenyl group, furylmethyl group, phenoxy group or phenylthio group, and R ₅ represents a hydrogen atom or a methyl group, or adjacent R ₄ and R ₅ or R ₅ are bonded together at the terminals. forms a tetramethylene chain, t represents an integer of 1 or 2, R ₆ represents a hydrogen atom, an ethynyl group or a nitrile group, and Y represents an oxygen atom, a sulfur atom or -CH=CH-
represents a group, R ₇ is a phthalimide group, a thiophthalimide group,
a di- or tetrahydrophthalimide group or a dialkylmaleimide group, R ₁₀ represents a thienyl group or a furyl group, and Z represents a methyl group] or a reactive derivative thereof. A general formula () characterized by: A method for producing an acetic acid derivative represented by [wherein m, R ₁ , R ₂ and R ₃ have the same meanings as defined in the above formulas () and ()]. 3 General formula (): [In the formula, m represents an integer of 1 to 4, R ₁ represents a lower alkyl group, a lower alkoxy group, or a halogen atom, provided, however, that it contains at least one lower alkoxy group, and R ₂ represents a lower alkyl group. , represents a lower alkenyl group, lower alkoxy group, lower haloalkyl group or lower haloalkenyl group, R ₃ is the following general formula (), () or (): [Formula] R ₇ −CH ₂ − () (In the formula, R ₄ is a hydrogen atom, an allyl group, a propargyl group,
It represents a benzyl group, thenyl group, furylmethyl group, phenoxy group or phenylthio group, and R ₅ represents a hydrogen atom or a methyl group, or adjacent R ₄ and R ₅ or R ₅ are bonded together at the terminals. forms a tetramethylene chain, t represents an integer of 1 or 2, R ₆ represents a hydrogen atom, an ethynyl group or a nitrile group, and Y represents an oxygen atom, a sulfur atom or -CH=CH-
represents a group, R ₇ is a phthalimide group, a thiophthalimide group,
a di- or tetrahydrophthalimide group or a dialkylmaleimide group, R ₁₀ represents a thienyl group or a furyl group, and Z represents a methyl group] as an active ingredient. Characteristic insecticide. 4. The insecticide according to claim 3, which contains a pyrethroid as a synergist.