JPH0959115A - Insecticidal/acaricidal composition having excellent light stability - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition suppressing photodecomposition of an oxazoline-based compound and having exceedingly improved insecticidal.acaricidal effect and after-effect by adding more than one kind of a specific ultraviolet ray absorber to an oxazoline compound in a specific ratio. SOLUTION: An oxazoline compound (A) of formula I (R1 and R2 are each H or a halogen; R3 is H, a halogen, an alkyl, etc.; R4 is H, a halogen, an alkyl, phenyl, etc.) is mixed with one or more than two kinds of compounds selected from a cyanoacrylate compound of formula II (R5 is an alkyl), a benzophenone- based compound of formula III (R6 is H or an alkyl) and a compound of formula IV (R7 is t-butyl or H; R8 is methyl, etc.; R9 is H or Cl) in a weight ratio of (the former/the latter) of (1/0.1)-(1/20). As the compound of the formula I, e.g. 2-(2-chloro-6-bromphenyl)-4-(2-methyl-4-chlorophenyl)-2-oxazoline, etc., is exemplified. As the ultraviolet ray absorber, e.g. ethyl-2-cyano-3,3'-diphenylacrylate, etc., is exemplified.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to an insecticidal and acaricidal composition having good photostability.

[0002]

PRIOR ART AND PROBLEMS TO BE SOLVED The following general formula (I)
The oxazoline compound represented by is already known as an insecticidal and acaricidal agent (Japanese Patent Application Nos. 1-142888 and 2-329851). However, the photostability of these oxazoline compounds is not always sufficient like other organic synthetic compounds, and selection of the photostabilizer is important. Further, the use of light stabilizers in the agricultural field is small, and for example, JP-A-59-39807 and 61-148106.
It has been proposed to add a light stabilizer to some insecticidal and acaricidal active compounds. However, nothing is known about a photostable composition using a photostabilizer for an oxazoline compound.

[0003]

Means for Solving the Problems As a result of intensive investigations by the present inventors on a photostable formulation of an oxazoline compound represented by the general formula (I), the oxazoline compound represented by the general formula (I) is provided with a specific ultraviolet ray described below. It was found that the photodecomposition of the oxazoline-based compound is suppressed and the insecticidal and acaricidal effect and the residual effect are remarkably improved by adding one or more absorbents, and the present invention has been completed.

The present invention has the following general formula (I)

Embedded image [Wherein R ₁ and R ₂ represent a hydrogen atom or a halogen atom, and R ₃ represents a hydrogen atom, a halogen atom, a lower alkyl group,
Represents a lower alkoxy group, a lower haloalkyl group or a lower haloalkoxy group, and R ₄ represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a lower haloalkyl group, a lower haloalkoxy group or a phenyl group (a halogen atom, an alkyl group, an alkoxy group). , A lower haloalkyl group, which may be substituted with a lower haloalkoxy group), and an oxazoline derivative represented by the following general formula (II)

[Chemical 6] (In the formula, R ₅ represents a linear or branched alkyl group having 1 to 8 carbon atoms), an anoacrylate compound represented by the following general formula (III)

[Chemical 7] (In the formula, R ₆ represents a hydrogen atom or a linear or branched alkyl group having 1 to 12 carbon atoms) or a benzophenone compound represented by the general formula (IV)

Embedded image (Wherein the R ₇ is tert- butyl or hydrogen atom, R ₈
Is a methyl group or a tert-butyl group, and R ₉ is a hydrogen atom or a chlorine atom), and one or more compounds selected from the benzotriazole compounds are used in a weight ratio of 1: 0.1 to 0.1. An insecticidal and acaricidal composition having good photostability, which is characterized by containing 20 parts by weight.

Examples of the oxazoline compound of the formula I include the following compounds. Compound 1: 2- (2-chloro-6-bromophenyl)-
4- (2-methyl-4-chlorophenyl) -2-oxazoline, compound 2: 2- (2,6-difluorophenyl) -4-
(2-chloro-4-n-propoxyphenyl) -2-oxazoline, compound 3: 2- (2,6-difluorophenyl) -4-
(2-Ethoxy-4-tert-butylphenyl) -2
-Oxazoline, compound 4: 2- (2-fluorophenyl) -4- (2-
Trifluoromethyl-4-chlorophenyl) -2-oxazoline, compound 5: 2- (2,6-difluorophenyl) -4-
(4-octylphenyl) -2-oxazoline, compound 6: 2- (2-fluoro-6-chlorophenyl)
-4- (2-propoxy-4-chlorophenyl) -2-
Oxazoline, compound 7: 2- (2,6-difluorophenyl) -4-
(2-n-propoxyphenyl-4-chlorophenyl)
-2-oxazoline, compound 8: 2- (2,6-difluorophenyl) -4-
(2-Ethoxy-4-trifluoromethylphenyl)-
2-oxazoline, compound 9: 2- (2-fluoro-6-chlorophenyl)
-4- (2-tert-butyl-4-ethoxyphenyl) -2-oxazoline, compound 10: 2- (2,6-difluorophenyl) -4
-(2-chlorodifluoromethoxy-4'-i-propyl-4-biphenyl) -2-oxazoline,

Compound 11: 2- (2,6-difluorophenyl) -4- (4'-trifluoromethoxy-4-biphenyl) -2-oxazoline, Compound 12: 2- (2,6-difluorophenyl)- Four
-(4'-1,1,2,2-tetrafluoroethoxy-
4-biphenyl) -2-oxazoline, compound 13: 2- (2,6-difluorophenyl) -4
-(4'-chloro-4-biphenyl) -2-oxazoline, compound 14: 2- (2,6-difluorophenyl) -4
-(4'-ethoxy-4-biphenyl) -2-oxazoline, compound 15: 2- (2,6-difluorophenyl) -4
-(4'-1,1,2,3,3,3-hexafluoropropoxy-4-biphenyl) -2-oxazoline, compound 16: 2- (2,6-difluorophenyl) -4
-(4'-1,1,2-trifluoro-2-chloroethoxy-4-biphenyl) -2-oxazoline, compound 17: 2- (2,6-difluorophenyl) -4
-(2-Methyl-4'-trifluoromethoxy-4-biphenyl) -2-oxazoline, compound 18: 2- (2,6-difluorophenyl) -4
-(2-chloro-4'-trifluoromethoxy-4-biphenyl) -2-oxazoline, compound 19: 2- (2,6-difluorophenyl) -4
-(2-Fluoro-4'-trifluoromethoxy-4-
Biphenyl) -2-oxazoline,

UV absorber-Cyanoacrylate-based compound Compound A: ethyl-2-cyano-3,3'-diphenylacrylate, compound B: 2-ethylhexyl-2-cyano-3,3 '
-Diphenyl acrylate, -benzophenone compound C: 2-hydroxy-4-methoxybenzophenone, compound D: 2-hydroxy-4-octoxybenzophenone, compound E: 2,4-dihydroxybenzophenone, -benzotriazole compound F : 2- (2'-hydroxy-3 ', 5'-di-
tert-butylphenyl) benzotriazole, Compound G: 2- (2'-hydroxy-3'-tert-
Butyl-5'-methylphenyl) benzotriazole, compound H: 2- (2'-hydroxy-3 ', 5'-di-
tert-butylphenyl) -5-chlorobenzotriazole, Compound I: 2- (2'-hydroxy-3'-tert-
Butyl-5'-methylphenyl) -5-chlorobenzotriazole,

In the insecticidal and acaricidal composition of the present invention, the compound of the general formula (I) and one or more compounds (A) to (I) may be used as they are, or a liquid carrier, a solid carrier or an auxiliary agent. Etc. may be added to prepare a powder, granule, emulsion, oil, wettable powder, flowable formulation or the like for use.
Examples of the liquid carrier include water, aromatic hydrocarbons such as xylene, toluene, benzene, dimethylnaphthalene; chlorinated hydrocarbons such as chlorobenzene, chloromethylene, chloroethylene, carbon tetrachloride; aliphatic or Alicyclic hydrocarbons such as benzine, cyclohexane, hexane and the like; alcohols such as ethanol, propanol, butanol and the like; ketones such as acetone, methyl ethyl ketone, cyclohexanone and the like. Examples of the solid carrier include natural mineral powders such as bentonite, talc, clay, kaolin, montmorillonite, diatomaceous earth and calcium carbonate; synthetic mineral powders such as alumina, white carbon and silicate.

As the auxiliary agent, for example, a surfactant, a dispersant, a fixing agent, a wetting agent, a stabilizer and the like are used. Examples of the surfactant include alkyl sulfates, alkyl sulfonates, polyoxyethylene glycol ethers, polyoxyethylene glycol esters, polyhydric alcohol esters and the like. Examples of the fixing agent and the dispersant include casein, gelatin, arabic gum,
Examples thereof include alginic acid, lignin, bentonite, polyvinyl alcohol and the like. Examples of the stabilizer include PAP
(Isopropyl phosphate), BHT (2,6-di-ter
t-butyl-4-methylphenol), TCP (tricresyl phosphate), vegetable oil, mineral oil, surfactant,
Examples thereof include fatty acids and their esters.

In the insecticidal and acaricidal composition of the present invention, the mixing ratio of the compound of the general formula (I) and the compounds (a) to (I) is 1: 0.1-20, preferably 1: 0. .1
-10 It is particularly preferably 1: 0.3-5.

The effective application amount of the insecticidal and acaricidal composition of the present invention is usually about 0.1 to 10 per 10 ares.
1000 g, preferably 5 to 500 g is suitable.
The insecticidal and acaricidal composition of the present invention can be applied to a place where pests or mites live, for example, by spraying, spraying, dusting, granulating, fumigating or the like directly or by using a device. The insecticidal and acaricidal composition of the present invention includes other insecticides, nematicides,
Acaricide, fungicide, herbicide, plant growth regulator, synergist,
Fertilizers, soil conditioners, animal feeds and the like can be further compounded, or they can be used together without compounding.

[0012]

EXAMPLES The compositions of the present invention will be illustrated below, but the present invention is not limited thereto. The "parts" in the formulation examples mean "parts by weight". Formulation Example 1 [Emulsion] 10 parts of compound (17), 5 parts of compound (A), 8 parts of polyoxyethylene styryl phenyl ether, 2 parts of alkylallyl sulfonate and 75 parts of xylol were uniformly mixed and dissolved to prepare an emulsion.

Formulation Example 2 [Wettable Powder] 10 parts of compound (5), 5 parts of compound (F), polyoxyethylene styryl phenyl ether sulfate salt 10
Parts, 20 parts of white carbon and 55 parts of diatomaceous earth were uniformly mixed and pulverized with a jet air meal to prepare a wettable powder.

Formulation Example 3 [Flowable Agent] 5 parts of compound (D), 5 parts of polyoxyethylene styryl phenyl ether sulfate salt, 20 parts of 1% xanthan gum aqueous solution, 1 part of sucmate type mineral substance and 59 parts of water are uniformly dissolved. Then, 10 parts of compound (3) was added, and the mixture was stirred and wet-ground with a sand mill to prepare a flowable agent.

Formulation Example 4 [Aqueous Emulsion] 30 parts of 15% aqueous solution of polyvinyl alcohol, 5 parts of 1% aqueous solution of xanthan gum, 1 part of sucmate type mineral substance and water 29
Parts of the compound (11), 5 parts of the compound (C) and 20 parts of xylylphenylethane were heated and dissolved, and the resulting mixture was emulsified and dispersed by a homogenizer to prepare an aqueous emulsion. .

Next, the decomposition prevention effect and biological effect test of the active ingredient of the present invention will be specifically described. The oxazoline compound was analyzed by extracting the components in the composition with acetonitrile and measuring it with a high performance liquid chromatograph equipped with an ultraviolet spectrophotometric detector. Further, the decomposition rate with respect to the content after the preparation was determined by the following formula.

[Formula 1] Decomposition rate (%) = (content after formulation-remaining amount after irradiation with sunlight) / content after formulation x 100

Test Example 1 [Test for Decomposition-Preventing Effect of Oxazoline Preparation] Various emulsions were prepared according to Preparation Example 1, 1 ml of the emulsion was diluted with 1000 ml of water, and 10 ml was put into a glass petri dish having a diameter of 9 cm to remove water. After evaporating, the mixture was left under sunlight irradiation for 3 days, and the decomposition rate was determined according to the above-mentioned analysis method. In addition, the weather for 3 days is fine and the accumulated illuminance for 3 days is 19
It was 44 klx · h. The results are shown in Tables 1 to 10.

[0018]

[Table 1]

[0019]

[Table 2]

[0020]

[Table 3]

[0021]

[Table 4]

[0022]

[Table 5]

[0023]

[Table 6]

[0024]

[Table 7]

[0025]

[Table 8]

[0026]

[Table 9]

[0027]

[Table 10]

Test Example 2 [Test for Decomposition Prevention Effect of Oxazoline Preparation] Various flowable agents were prepared according to Preparation Example 3, 1 g of the flowable agent was diluted with 1000 ml of water, and 10 ml was put into a glass petri dish having a diameter of 9 cm to obtain a water content. Was evaporated and left for 3 days under irradiation of sunlight, and the decomposition rate was determined according to the above-mentioned analysis method. The weather for three days was fine, and the integrated illuminance for three days was 2281 klx · h. Table 11 shows the results.
~ 12.

[0029]

[Table 11]

[0030]

[Table 12]

Test Example 3 [Biological effect test against spider mites] Using the emulsions and flowable agents prepared according to Formulation Examples 1 and 3, a potency test against spider mites was carried out in the following manner. The composition of the present invention was dispersed in water to adjust the concentration of the oxazoline compound to 100 ppm, and the drug solution was sprayed on the foliage of kidney beans planted in a pot (diameter 20 cm).
After air-drying, move the pot outdoors and spray the chemical solution on the first day, 15
On day 30 and day 30, each kidney leaf is cut off to make a leaf piece of 1 cm on each side. Ice cream container (diameter 9c
Water was put in m), a hole was made in a part of the lid, a filter paper with a strip-shaped slit was inserted there, and the entire filter paper was absorbed by water to make it wet, and the above kidney bean leaf pieces were placed on it. .
Each leaf was inoculated with 10 female adult mites, which were laid for 24 hours, and then the female adults were removed. After 7 days, the number of hatched larvae was examined under a microscope, and the ovicidal rate was calculated by the following formula. The test was performed in three sections per section. The results are shown in Tables 13 to 14 (emulsion) and Tables 15 to 16 (flowable agent).

[Equation 2] Ovulation rate (%) = number of unhatched larvae / number of test eggs x 100

[0032]

[Table 13]

[0033]

[Table 14]

[0034]

[Table 15]

[0035]

[Table 16]

Test Example 4 [Biological effect test against green peach aphid] Using a wettable powder and an aqueous emulsion prepared according to Formulation Examples 2 and 4, a potency test against green peach aphid was conducted in the following manner. The composition of the present invention was dispersed in water to adjust the concentration of the oxazoline compound to 100 ppm, and the drug solution was sprayed on Japanese radish seedlings planted in a pot (diameter 10 cm). After air-drying, move the pot outdoors and spray the chemical solution one day later,
After 5 days and 10 days, 5 female adults of the green peach aphid were inoculated to the sprayed leaves of each pot and allowed to bear for 24 hours, and then the female adults were removed. After 3 days, the number of larvae was examined, and the larvalicidal rate was calculated by the following formula. The test was performed in three sections per section. The results are shown in Tables 17 to 18 (wettable powder) and Tables 19 to 20 (aqueous emulsion).

[Formula 3] Laricidal rate (%) = number of dead larvae / number of test larvae x 100

[0037]

[Table 17]

[0038]

[Table 18]

[0039]

[Table 19]

[0040]

[Table 20]

[0041]

INDUSTRIAL APPLICABILITY The insecticidal and acaricidal agent of the present invention greatly improves the photostability of oxazoline compounds in sunlight and significantly improves the residual effect. Further, the insecticidal and acaricidal agent of the present invention is physically stable even after long-term storage, chemically suppresses the decomposition of the active ingredient, and sufficiently exerts an insecticidal and acaricidal effect. Furthermore, there is no danger of phytotoxicity to useful plants.

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[Procedure amendment]

[Submission date] December 8, 1995

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] Name of invention

[Correction method] Change

[Correction contents]

Title: Insecticidal / acaricidal composition having good photostability

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Office reference number FI technical display location // C07D 263/10 C07D 263/10 487/04 132 487/04 132 (A01N 43/76 37: 34) (A01N 43/76 35:04) (A01N 43/76 43:90) (72) Inventor Eiichiro Hoshino 173-2 Tomitake, Nagano, Nagano Prefecture Yashima Chemical Industry Co., Ltd.

Claims (1)

[Claims] 1. A compound represented by the following general formula (I) (In the formula, R ₁ and R ₂ represent a hydrogen atom or a halogen atom, R ₃ represents a hydrogen atom, a halogen atom, a lower alkyl group,
Represents a lower alkoxy group, a lower haloalkyl group or a lower haloalkoxy group, and R ₄ represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a lower haloalkyl group, a lower haloalkoxy group or a halogen atom, an alkyl group, an alkoxy group, a lower haloalkyl Group, a phenyl group which may be substituted with a lower haloalkoxy group), and an oxazoline compound represented by the following general formula (II): (In the formula, R ₅ represents a straight-chain or branched alkyl group having 1 to 8 carbon atoms), a cyanoacrylate compound represented by the following general formula (III): (Wherein, R ₆ represents a hydrogen atom or a linear or branched alkyl group having 1 to 12 carbon atoms) or a benzophenone compound represented by the general formula (IV): (In the formula, R ₇ represents a tert-butyl group or a hydrogen atom,
₈ is a methyl group or a tert-butyl group, and R ₉ is a hydrogen atom or a chlorine atom) and one or more compounds selected from the benzotriazole compounds are used in a weight ratio of 1: 0.1. An insecticidal and acaricidal composition having good photostability, which is characterized in that it is contained in a proportion of from 20 to 20.