JPH07173010A - Insecticidal composition - Google Patents

Abstract

PURPOSE:To obtain the subject composition capable of manifesting excellent insecticidal effects especially on aleyrodids by synergistic effects by mixing a certain kind of pyrethroid-based compound with a certain kind of aniline derivative having germicidal activities. CONSTITUTION:This insecticidal composition is obtained by combining (A) an aniline derivative selected from dichlofluanid, procymidone and 3-(3,5- dichlorophenyl)-5-methyl-5-vinyl-1,3-oxazin-2,4-dione with (B) a pyrethroid-based compound selected from alpha-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2, 2- dimethylcyclopropanecarboxylate, alpha-cyano-3-phenoxybenzyl 3-(2-chloro-3,3,3- trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate and ethofenprox. For example, aphids, aleyrodids, thripids and tineoids are cited as insect pests which are objects of controlling.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION This invention relates to insecticidal compositions.

2. Description of the Related Art Conventionally, the development of insecticides for controlling whiteflies and the like has been extensively developed, and a wide variety of agents are put to practical use.
However, in recent years, whiteflies in particular have rapidly developed resistance to various drugs, and the effects of various drugs have been significantly reduced, and new insecticides having excellent effects on whiteflies have been particularly desired.

[0002]

In view of such circumstances, the present inventors have made various studies to develop an excellent insecticidal composition, and as a result, some pyrethroid compounds have a certain bactericidal activity. It was found that the use of the aniline derivative (1) as a mixture provides a superior insecticidal effect against whiteflies, due to a synergistic effect, and completed the present invention. That is, the present invention provides (a) N-dichlorofluoromethylthio-N ′, N′-dimethyl-N-phenylsulfamide (Compound A-1: general name diclofluanide), N- (3,5-dichlorophenyl). ) -1,2-Dimethylcyclopropane-1,2-dicarboximide (Compound A-2: general name procymidone) and 3-
An aniline derivative selected from the group consisting of (3,5-dichlorophenyl) -5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione (Compound A-3);
(B) α-cyano-3-phenoxybenzyl 3-
(2,2-Dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (Compound B-1), α-cyano-3-phenoxybenzyl 3- (2-chloro-3,
3,3-trifluoropropenyl) -2,2-dimethylcyclopropanecarboxylate (Compound B-2), α
-Cyano-3-phenoxybenzyl 2,2,3,3-
Tetramethylcyclopropane carbochelate (Compound B
-3), α-cyano-3-phenoxybenzyl 2-
(4-chlorophenyl) -3-methylbutyrate (Compound B-4), 2- (4-ethoxyphenyl) -2-methylpropyl 3-phenoxybenzyl ether (Compound B-5: generic name etofenprox), α -Cyano-
3-phenoxybenzyl 3- (2,2-dibromovinyl) -2,2-dimethylcyclopropanecarboxylate (Compound B-6), 2-methylbiphenyl-3-ylmethyl 3- (2-chloro-3,3,3) 3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate (Compound B-7) and 3-phenoxybenzyl 3- (2,2-dichlorovinyl) -2,
An insecticidal composition (hereinafter, referred to as the composition of the present invention) comprising a pyrethroid compound selected from the group consisting of 2-dimethylcyclopropanecarboxylate (Compound B-8) as an active ingredient. .

The active ingredient compound according to the present invention may have stereoisomers and geometrical isomers, and the present invention includes these isomers and mixtures thereof. Examples of such isomers are shown below with compound numbers. (RS) -3- (3,5-Dichlorophenyl) -5-methyl-5-vinyl-1,3-oxazolidine-2,4-
Dione (Compound A-3a: generic name vinclozolin) α-cyano-3-phenoxybenzyl 3- (2,2-
(1R cis) S and (1S c of dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate
is) R enantiomer pair (compound B-1a: generic name alphamethrin) α-cyano-3-phenoxybenzyl 3- (2-chloro-3,3,3-trifluoroprop-1-enyl)-
(Z)-(1R, 3S), S-ester and (Z)-of 2,2-dimethylcyclopropanecarboxylate
(1S, 3S), 1: 1 mixture of R-esters (Compound B-2a: generic name lambda cyhalothrin) (RS) -α-cyano-3-phenoxybenzyl 2,
2,3,3-Tetramethylcyclopropanecarboxylate (Compound B-3a: generic name phenpropatrine) (RS) -α-cyano-3-phenoxybenzyl (R
S) -2- (4-chlorophenyl-3-methylbutyrate (Compound B-4a: generic name fenvalerate) (S) -α-cyano-3-phenoxybenzyl (1
R, 3R) -3- (2,2-dibromovinyl) -2,2
-Dimethylcyclopropanecarboxylate (Compound B
-6a: generic name deltamethrin) (2-methylbiphenyl-3-yl) methyl 3- (2
-Chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate (Compound B-7a: generic name bifenthrin) In the active ingredient compound of the present invention, compound A-1 ,
Compound A-2 and compound A-3a are respectively described in Farm Chemicals Handbook 1991 (published by Meister Publishing Company) C131, C288 and C322. Compounds B-1a, B-2a, B-3a, B-
4a, B-5, B-6a and B-7a are respectively from Farm Chemicals Handbook 1991 C134, C175, C13.
7, C138, C308, C97 and C44.

Specific examples of the pests to be controlled in the composition of the present invention include the following. Aphids such as the green peach aphid (Myzus persicae) and the cotton aphid (Aphis gossypii), the insect white beetle (Bemisia tabaci), the whiteflies (Trialeurodes rtalis vaporariorum), and the whiteflies (Coleoptera spp.). , Thrips palmi and other thrips, etc. Lepidoptera pests Pluttella xylostella, etc. Hagrigiga of Phyllocnistics citrella and other insect pests such as the tick mites (Tetranychus urticae), kanzawa mites (Tetranychus kanzawai), citrus mites
citri), spider mites such as apple spider mite (Panonychus ulmi), etc., and the like, as crops to which the composition of the present invention is applied, fruit trees, vegetables, cotton, cotton,
Agricultural and horticultural crops such as flowers can be given.

The (a) aniline derivative and (b) pyrethroid compound used as the active ingredients in the present invention may be used as they are without adding any other ingredients, but usually, they are solid carriers and liquids. Mixtures with various carriers such as carriers and gaseous carriers, and if necessary, add surfactants and other auxiliaries for formulation as additives to prepare emulsions, wettable powders, suspensions in water, emulsions in water, etc. Flowables, powders, aerosols,
Used as a ULV agent or the like, or each active ingredient is previously formulated into various dosage forms as described above and then mixed, or further diluted with water to prepare each drug solution and then mixed. You can also In these preparations, the mixing weight ratio of (a) aniline derivative and (b) pyrethroid compound as active ingredients is usually 50: 1 to 1: 1.
The total amount of active ingredients in the preparation is usually 0.1 to 95% by weight. Examples of solid carriers used in the preparation include clays (kaolin clay, diatomaceous earth,
Synthetic hydrous silicon oxide, bentonite, fubasami clay, acid clay, etc., talc, ceramics, other inorganic minerals (serisite, quartz, sulfur, activated carbon, calcium carbonate,
Hydrated silica, etc., chemical fertilizers (ammonium sulfate, phosphorus ammonium, ammonium nitrate, urea,
Examples of liquid carriers include water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzene, benzene, etc.). Toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane,
Kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide, soybean oil, vegetable oils such as cottonseed oil, and the like, and a gaseous carrier, that is, a propellant, Examples thereof include CFC gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide gas and the like. Examples of the surfactant include alkyl sulfate salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenated products thereof, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives and the like. can give. Examples of formulation adjuvants such as sticking agents and dispersants include casein, gelatin, polysaccharides (starch powder, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (polyvinyl alcohol). , Polyvinylpyrrolidone, polyacrylic acids, etc., and examples of the stabilizer include PAP (isopropyl acid phosphate) and BH.
T (2,6-di-tert-butyl-4-methylphenol), BHA (mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil , Surfactants, fatty acids or esters thereof, and the like. The formulation of a flowable agent (suspension in water or emulsion in water) is generally 1 to 7 by weight.
5% by weight of the compound is 0.5 to 15% by weight of the dispersant, 0.1% to 10% by weight of the suspension aid (for example, a compound that imparts protective colloid or thixotropic property), and the weight is 0% by weight. ~ 1
Finely dispersed in water containing 0% of suitable auxiliaries (eg, antifoaming agent, rust preventive, stabilizer, spreading agent, penetration aid, antifreezing agent, antibacterial agent, antifungal agent, etc.) It is obtained by It is also possible to use an oil in which the compound is hardly dissolved in place of water to prepare a suspension in oil. As the protective colloid, for example, gelatin, casein, gums, cellulose ether, polyvinyl alcohol, etc. are used.
Examples of the compound that imparts thixotropic properties include bentonite, aluminum magnesium silicate,
Examples include xanthan gum and polyacrylic acid.

In the agent of the present invention, if necessary, an antioxidant or an ultraviolet absorber, for example, a phenol derivative such as BHT or BHA, a bis-phenol derivative or phenyl-α-naphthylamine, phenyl-β-naphthylamine, phenetidine and acetone. By adding an appropriate amount of arylamines or benzophenone compounds such as condensates as a stabilizer, a composition with more stable effects can be obtained. The formulation thus obtained is
Used as it is or diluted with water or the like. In addition, with or without mixing with other insecticides, nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feed, etc. Can also be used simultaneously. The application amount of the agent of the present invention is generally about 5 g to about 1,000 g, preferably about 5 g, based on the total amount of active ingredients per 10 ares.
It is from 0 g to about 300 g. When an emulsion, wettable powder, flowable agent, etc. is diluted with water, the application concentration is usually about 100 ppm to about 3,000 ppm, preferably about 500 ppm to about 2,
It is 000ppm, and powders, aerosols, ULVs, etc. are applied as they are without any dilution. The application amount and application concentration depend on the type of active ingredient, type of formulation, application period, application location, application method, type of whiteflies, damage level, etc., and increase regardless of the above range. It can be reduced or increased.

[0007]

EXAMPLES The present invention will be described in more detail with reference to production examples and test examples, but the present invention is not limited to these examples. In the production examples, all parts are parts by weight. Production Example 1 Emulsion Compound A-1, Compound A-2 or A-3a 10 parts,
Compounds B-1a, B-2a, B-3a, B-4a, B-
5, B-6a or B-7a (10 parts) were mixed and dissolved in 30 parts of xylene and 30 parts of dimethylformamide. To this, 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzene sulfonate were added. Stir-mix to obtain each 20% emulsion. Production Example 2 Wettable powder Compound A-1, Compound A-2 or A-3a 10 parts,
Compounds B-1a, B-2a, B-3a, B-4a, B-
5, B-6a or B-7a 10 parts were mixed and added to a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of diatomaceous earth, and a juice mixer. Stir mix at to obtain each 20% wettable powder. Production Example 3 Granular wettable powder To compound A-1, compound A-2 or 10 parts of A-3a,
Compounds B-1a, B-2a, B-3a, B-4a, B-
5, B-6a or B-7a (10 parts) are mixed, and sodium formalin sulfonate formalin condensate 10 is added to the mixture.
Parts, sodium alkylnaphthalene sulfonate 1.5 parts,
ASP-400P (Kaolin clay made by Engelhard)
Is added to form 100 parts, and the mixture is thoroughly mixed in a bag, and then finely pulverized using an air mill. The crushed material was placed in a pan granulator with a diameter of 40 cm and rotated at a rotation speed of 45 rpm.
Granules are molded while spraying about 20 parts of distilled water with 100 parts of powder with a hand sprayer. The granulated product is dried in a fluid bed dryer (50 ° C., 20 minutes) and sieved with 14 to 30 mesh to obtain each 20% granular wettable powder (WGD). Production Example 4 Dust agent To compound A-1, compound A-2 or A-3a 1.0 part,
Compounds B-1a, B-2a, B-3a, B-4a, B-
5, B-6a or B-7a 1.0 parts were mixed, dissolved in an appropriate amount of acetone, and 5 parts of synthetic hydrous silicon oxide fine powder, 0.3 parts of PAP and 92.7 parts of clay were added to the mixture, and a juice mixer was added. Stir and mix with to remove acetone by evaporation to give each 2.0% powder. Production Example 5 Flowable Agent Compound A-1, Compound A-2 or A-3a 10 parts,
Compounds B-1a, B-2a, B-3a, B-4a, B-
5, B-6a or B-7a 10 parts were mixed and added to 40 parts of an aqueous solution containing 6 parts of polyvinyl alcohol,
Stir with a mixer to obtain a dispersant. Xanthan gum 0.05 parts and aluminum magnesium silicate 0.
30 parts of an aqueous solution containing 1 part is added, 10 parts of propylene glycol is further added, and the mixture is gently stirred and mixed to obtain each 20% flowable agent. Production Example 6 Oily Aerosol To compound A-1, compound A-2 or A-3a 0.5 part,
Compounds B-1a, B-2a, B-3a, B-4a, B-
5, B-6a or B-7a 0.5 part, trichloroethane 10 parts and deodorizing kerosene 59 parts are mixed and dissolved, filled into an aerosol container, and after a valve part is attached, a propellant (liquefied petroleum gas) is passed through the valve part. 30 parts by pressure is filled to obtain each oil-based aerosol. Production Example 7 Aqueous aerosol To compound A-1, compound A-2 or A-3a 0.5 part,
Compounds B-1a, B-2a, B-3a, B-4a, B-
5, B-6a or B-7a 0.5 parts, xylene 5 parts, deodorized kerosene 3.0 parts and emulsifier {Atmos 300 (Atlas Chemical registered trade name)} 1 part were mixed and dissolved, and pure 50 parts Fill the aerosol container, attach the valve part, and propellant (liquefied petroleum gas) through the valve part.
40 parts under pressure are filled to obtain each aqueous aerosol. Production Example 8 Heating and smoking agent Compound A-1, compound A-2 or A-3a 50 mg, and compound B-1a, B-2a, B-3a, B-4a,
50 mg of B-5, B-6a or B-7a was dissolved in an appropriate amount of acetone and impregnated into a porous ceramic plate having a size of 4.0 cm × 4.0 cm and a thickness of 1.2 cm to obtain each heated smoking agent.

Next, it is shown by a test example that the composition of the present invention exhibits an excellent insecticidal effect by a synergistic action, as compared with the case where the (a) aniline derivative and the (b) pyrethroid compound are used alone. The aniline derivatives used for comparison and control are shown by the following compound symbols. Compound C-1: 3- (3,5-dichlorophenyl) -N
-Isopropyl-2,4-dioxoimidazolidine-1
-Carboximide (generic name: iprodione)

Test Example Compound B-1a (Fastac 10EC manufactured by Shell International Chemical Co.) formulated as an emulsion,
B-2a (Kate 2.5E manufactured by ICI Agro Chemicals)
C), B-3a (Sumitomo Chemical Co., Ltd., Rody 10
EC), B-5 (Trebon 20 manufactured by Kumiai Chemical Co., Ltd.)
EC), B-6a (Decel 2.5 manufactured by Roussel Yuclaf)
EC) and compound A-1 formulated as a wettable powder
(Yupalen 50WP manufactured by Nippon Special Agricultural Chemicals Co., Ltd.), A-
2 (Hokkaido Chemical Co., Ltd. Procymidon 50WP), A-
3a (Sankyo Roniran 50WP), B-7a
(Nissan Kagaku Co., Ltd. Telstar 2WP) and C-1 (Takeda Pharmaceutical Co., Ltd. Lobrar 50WP) are each diluted with water, and the diluted solution is mixed to a predetermined active ingredient concentration to give a reagent. Obtained. 30 ml of the above-mentioned reagent solution was sprayed on kanran (4-5 leaf stage) planted in a polyethylene cup. After air-drying, the leaves were cut out and put into a plastic petri dish (diameter 9 cm, depth 2 cm) one by one, and then 50 to 100 adult whitefly white worms / dishes were released. The petri dish was kept in a room at 25 ° C., and after 24 hours, life and death was examined. (3 repeats) The results are shown in Tables 1 and 2. The theoretical insecticidal rate (%) and the synergistic index (%) were calculated by the following formulas.

## EQU00001 ## Theoretical value insecticidal rate (%) = A + {(100-A) * B} / 100

## EQU00002 ## Synergistic effect index (%) = {insecticidal rate (%) / theoretical value insecticidal rate (%)} × 100 where A is the compound A-1, A-2, A-3a or C.
-1 represents the insecticidal rate (%), B is compound B-1a,
B-2a, B-3a, B-5, B-6a or B-7a
The insecticidal rate (%) of

[Table 1]

[Table 2]

The composition of the present invention exhibits an excellent insecticidal effect.

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Claims (1)

[Claims] (A) N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenylsulfamide N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2- An aniline derivative selected from the group consisting of dicarboximide and 3- (3,5-dichlorophenyl) -5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione; and (b) α-cyano- 3-phenoxybenzyl 3-
(2,2-Dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, α-cyano-3-phenoxybenzyl 3- (2-chloro-3,3,3-trifluoropropenyl) -2,2-
Dimethylcyclopropanecarboxylate, α-cyano-3-phenoxybenzyl 2,2,3,3
-Tetramethylcyclopropane carbochelate, α-cyano-3-phenoxybenzyl 2- (4-chlorophenyl) -3-methylbutyrate, 2- (4-ethoxyphenyl) -2-methylpropyl
3-phenoxybenzyl ether, α-cyano-3-phenoxybenzyl 3- (2,2-
Dibromovinyl) -2,2-dimethylcyclopropanecarboxylate, 2-methylbiphenyl-3-ylmethyl 3- (2-chloro-3,3,3-trifluoroprop-1-enyl)
Containing a pyrethroid compound selected from the group consisting of 2,2-dimethylcyclopropanecarboxylate and 3-phenoxybenzyl 3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate as an active ingredient An insecticidal composition comprising: