JPH115708A - Insecticidal and bactericidal composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition having improved insecticidal and bactericidal effects by including a specific insecticidally active compound and a specific bactericidally active compound as active ingredients. SOLUTION: This composition comprises (A) an insecticidally active compound represented by the formula (R1 is H, methyl, etc.; R2 to R4 are each H, a 1-5C alkyl, etc.), and (B) at least one kind of a bactericidally active compound selected from (E)-2- 2-[6-(2-cyanophenoxy)pyrimidin 4-yloxy]phenyl}-3- methoxyacrylic acid methyl ester, N-[1-(2,4dichlorophenyl)ethyl]-2-cyano-3,3- dimethylbutanoic acid amide, 2-(E)-methoxyimino-2-[(2-methylphenoxy) methyl]phenyl acetic acid methyl ester and 7-thiomethoxycarbonyl-1,2,3- benzothiadiazole. The component A is mixed with the component B at the ratio of (500:1) to (1:500) and the active ingredient content is preferably 10<-7> to 95 wt.%.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel insecticidal and fungicidal composition exhibiting excellent insecticidal and fungicidal activities.

[0002]

2. Description of the Related Art The general formula (1) according to the present invention (formula 3)

[0003]

Embedded image (Wherein, R1 is a hydrogen atom or a methyl group, R2 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R3 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R4 is a hydrogen atom or 1 to 5 carbon atoms. (Hereinafter, also referred to as compound 1) is a novel compound having excellent insecticidal activity.

Further, methyl (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate (hereinafter referred to as compound A)
Described EP-382375 for controlling rice sheath blight and N- [1- (2,4-dichlorophenyl) ethyl].
-2-cyano-3,3-dimethylbutanoic acid amide (hereinafter referred to as compound B) is disclosed in JP-A-2-76846,
Methyl 2- (E) -methoxyimino-2-[(2-methylphenoxy) methyl] phenylacetate (hereinafter referred to as Compound C
JP-A-64-90176 describes that DE-4042272 and 7-thiomethoxycarbonyl-1,2,3-benzothiadiazole (hereinafter referred to as compound D) have a rice blast control effect. . However, the action of these active compounds alone is only an insecticidal effect or a bactericidal effect, and cannot simultaneously control pests.

[0005] By the way, in rice cultivation, a variety of pests are attacked during sowing, planting, and harvesting, and at present, a proper harvest cannot be obtained without chemical control. Therefore, it is necessary to perform pest control many times during this cultivation period, which is a great burden in terms of labor and cost. At the same time, the safety of the environment due to unnecessary treatment of the drug is also being viewed as a problem.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide a composition having an improved insecticidal fungicidal activity.

[0007]

Means for Solving the Problems The present inventors have made intensive studies to solve these problems, and as a result, the general formula (1)
A pesticidal fungicidal composition containing one kind of the pesticidally active compound represented by (Chemical Formula 3) and containing at least one kind of a fungicidally active compound selected from the compounds A to D is useful for controlling rice plant diseases and pests. At the same time, it was also found that when both compounds were mixed, the persistence of the insecticidal effect was increased, in addition to exhibiting excellent insecticidal and fungicidal effects over a wide range. Further, the present invention has been completed by considering that pests and diseases can be controlled efficiently at the same time, and that the effects of pests are enhanced, and that they are expected to greatly contribute to the reduction of the number of times of control.

That is, the present invention provides a compound represented by the following general formula (1):

[0009]

Embedded image (Wherein, R1 is a hydrogen atom or a methyl group, R2 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R3 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R4 is a hydrogen atom or 1 to 5 carbon atoms. And (E) -2- {2- [6-
(2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate methyl, N-
[1- (2,4-Dichlorophenyl) ethyl] -2-cyano-3,3-dimethylbutanoic acid amide, 2- (E)-
At least one fungicidally active compound selected from methyl methoxyimino-2-[(2-methylphenoxy) methyl] phenylacetate or 7-thiomethoxycarbonyl-1,2,3-benzothiadiazole. A pesticidal fungicidal composition characterized by the following.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION The production method of compound 1 and its use as an insecticide are described in JP-A-179448. Compound A, which is a fungicidally active compound according to the present invention, can be produced by the method described in EP-A-382375. Compound B, which is a fungicidally active compound according to the present invention, can be produced by the method described in JP-A-2-76846. Compound C, a fungicidally active compound according to the invention, is disclosed in German Patent No. 404.
The compound can be produced by the method described in No. 2272.
Compound D, which is a fungicidally active compound according to the present invention, can be produced by the method described in JP-A-64-90176.

When the insecticidal fungicidal composition of the present invention is actually applied, a mixture of the insecticidal compound and the fungicidal compound may be prepared in advance, or the pesticidal compound and the fungicidal compound may be mixed in situ. Each can be made into a single usual formulation. In preparing the composition of the present invention,
At least one fungicidally active compound selected from A to D is used, but two or more fungicidally active compounds may be used as a mixture. In the present invention, general formula (1)
Insecticidally active compound (compound 1) and compounds A to D
The mixing ratio with the fungicidally active compound is from 500: 1 to 1:50.
0, preferably 20: 1 to 1:20. When two or more fungicidal active compounds are used in combination, the ratio of each fungicidal active compound is from 500: 1 to 1: 500.

In formulating the insecticidal fungicidal composition of the present invention, no special conditions are required, and emulsions, wettable powders, powders, granules, and the like can be prepared by a method well-known in the art according to general pesticides. It can be prepared into any dosage form such as fine granules, flowables, microcapsules, oils, aerosols, surfs, throwing agents, smokers, baits and the like, and these can be used for various purposes according to the respective purposes.

The content of the active ingredient in combination with the insecticidal compound and the fungicidal compound in each dosage form is 0.0000001 to 9
5% by weight, preferably 0.0001 to 50% by weight, particularly 5 to 50% for emulsions, 5 to 50% for wettable powders,
0.1 to 5% for powders, 0.1 to 20% for granules, 0.1 to 5% for fine granules, 5 to 50% for flowables, 5 to 50% for microcapsules, and 0. 5% for oils. 1-2
0%, 0.01 to 5% for aerosol, 0.1 to 20% for surfing agents, 0.1 to 20% for throwing agents, 0.1 to 20% for smokers, 0.01 to 0.01 for poison baits and the like. 5%.

When the insecticidal compound and the fungicidal compound of the present invention are used as an insecticidal fungicidal composition, the drug substance may be directly applied to the insects or plants to be treated, but it is generally mixed with an inert carrier. It is used as a preparation in various preparation forms as described above. If necessary for the preparation, an auxiliary agent can be added.

[0015] The carrier as used in the present invention is intended to help the active ingredient to reach the site to be treated, to store the active ingredient compound,
A liquid, solid or gaseous synthetic or natural inorganic or organic substance that is formulated to facilitate transport and handling.

Suitable solid carriers include, for example, montmorillonite, kaolinite, diatomaceous earth, clay, talc, vermiculite, gypsum, calcium carbonate, silica gel,
Inorganic substances such as ammonium sulfate, soy flour, sawdust, flour, pectin,
Methylcellulose, sodium alginate, petrolatum,
Organic substances such as lanolin, liquid paraffin, lard, and vegetable oil are exemplified.

Suitable liquid carriers include, for example, toluene,
Aromatic hydrocarbons such as cumene and solvent naphtha, paraffinic hydrocarbons such as kerosene and mineral oil, halogenated hydrocarbons such as carbon tetrachloride, ketones such as acetone, methyl ethyl ketone and cyclohexanone, dioxane, tetrahydrofuran, ethylene glycol monomethyl Ethers such as ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, and propylene glycol monomethyl ether; esters such as ethyl acetate, butyl acetate, and fatty acid glycerin; nitriles such as acetonitrile and propionitrile methanol, ethanol, and n-propanol , Isopropanol, alcohols such as ethylene glycol, dimethylformamide, dimethylsulfoxide, water and the like.

Further, in order to enhance the efficacy of the insecticidal fungicidal composition of the present invention, the following adjuvants may be used alone or in combination according to the purpose in consideration of the dosage form of the preparation, the application scene, and the like. Can also be used. Emulsification, dispersion, expansion,
Auxiliaries used for the purpose of wetting, binding, stabilizing, etc. include water-soluble bases such as lignin sulfonates, alkylbenzene sulfonates, alkyl sulfates, polyoxyethylene alkyl aryl ethers, polyhydric alcohol esters And non-ionic surfactants such as calcium stearate, waxes and the like, stabilizers such as isopropylhydrodiene phosphate, and others such as methylcellulose, carboxymethylcellulose, casein and gum arabic. However, these components are not limited to those described above.

The insecticidal and bactericidal composition of the present invention is stable to light, heat, oxidation and the like, but if necessary, an antioxidant or an ultraviolet absorber such as BHT (2,6-di-t-butyl-).
Phenol derivatives such as 4-methylphenol) and BHA (butylhydroxyanisole); bisphenol derivatives; arylamines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, and condensates of phenetidine and acetone; or benzophenone-based compounds. By adding an appropriate amount of as a stabilizer, a composition having more stable effects can be obtained.

The insecticidally active compound and the fungicidally active compound represented by the general formula (1) used in the insecticidal and fungicidal composition of the present invention generally contain 0.001 to 5000 ppm of each of the active ingredients in order to apply the compound. Preferably 0.01 to
It is desirable to use a concentration of 1000 ppm. Also,
The application rate per 10a is generally 1 to 3 for each of the active ingredients.
00 g.

The insecticidal / bactericidal composition of the present invention exhibits an excellent insecticidal / bactericidal effect and exerts an accurate control effect on harmful pests. Such pests include, for example, armyworm, rice armyworm, phlebotoylium japonicus, tamanayaga, cottontailed lipstick, giant tobacco budworm, shirochimodojito, lotus scotch, kaburayaga, yotoga, tamaginawaba, nicameiga, konomeigashimai, suzumei ganiga, suzuka mei gan, suzume swordfish, swordfish, beetle
Wing scales such as cotton red beetle, potato moth, white butterfly, wild turtle moth, chanokomokumakimaki, chinmonhosoga, mandarin mogliga, grape hosohamaki, pear-spotted beetle, mameshinguiga, peach-spotted moth, grape sashiba, chanohosoga, konaga, harmful insects;
Whiteflies, Whiteflies, Whiteflies, White aphids, Cotton aphids, Snowy aphids, Apple aphids, Peach aphids, Japanese radish aphids, Nisedaikon aphids, Bean aphids, Japanese aphids, Citrus aphids, Grapevine aphid Aphids, Chamomidohimebikobi, Futentenhimekabiko, Japanese brown planthopper, brown planthopper, sagebill plant, tunagras leafhopper, Tigerleaf leafhopper, white leafhopper, rubylom beetle, olive beetle, scorpionfish, reddish beetle, reddish beetle Insects, stag beetles, citrus Iseria scale insects, Ringokijirami, Diaphorina citri, southern green stink bug, bombardier helicopter bugs, Hemiptera such Nashigunbai;. Rice water weevil, Inedorooimushi, Kisujinomihamushi, Colorado potato beetle, ten sites bi beetle, Diabrotica spp, maize weevil, clear Keshikisui, Nijuuyahoshi Coleoptera, Scarabaeidae, Scarabaeidae, Scarabaeidae, Scarabaeidae, Scarabaeidae, A. Butterfly, rice flies, houseflies, houseflies,
Diptera pests such as black fly, onion fly, sea flies and citrus flies; thrips insects such as wall thrips, thrips thrips, thrips thrips, thrips thrips, thrips thrips, and thrush; Orthoptera pests; Hymenoptera pests, such as the wasp wasp; spider mite, Kanzawa spider mite, mandarin spider mite, apple spider mite, Dermatophagoids
Acarid pests such as Citrus mite, Dermatophagoides mite, House dust mites, Scrubberid mites, Scarabaeidae; and other dog fleas, head lice, Yamato termites, Yasukusadei and Geji.

The diseases which can be controlled by the composition of the present invention include, for example, blast ( Pyricularia ryzae ) and sheath blight ( Rhizoctonia solani ).

[0023]

EXAMPLES Next, the pesticidal fungicidal composition of the present invention will be described in detail with reference to formulation examples. The content of active ingredients, the type and content of auxiliary components such as carriers and auxiliary agents, and the target pests are Needless to say, it is limited to.

The compound 1 is a compound contained in the general formula (1), R1 is a hydrogen atom, R2 is a hydrogen atom,
R3 represents a methyl group, and R4 represents a compound represented by a hydrogen atom. Further, “parts” means “parts by weight”.

Formulation Example 1 Compound 1 (10 parts), Compound B (40 parts), Solpol 35
5S (Toho Chemical Co., surfactant) 10 parts, Solvesso 1
Emulsion was obtained by uniformly stirring and mixing 50 parts (produced by Exxon) of 40 parts or more.

Formulation Example 2 Compound 1 (10 parts), Compound C (40 parts), Solpol 35
5S (Toho Chemical Co., surfactant) 10 parts, Solvesso 1
Emulsion was obtained by uniformly stirring and mixing 50 parts (produced by Exxon) of 40 parts or more.

Formulation Example 3 10 parts of compound 1, 40 parts of compound D, solpol 35
5S (Toho Chemical Co., surfactant) 10 parts, Solvesso 1
Emulsion was obtained by uniformly stirring and mixing 50 parts (produced by Exxon) of 40 parts or more.

Formulation Example 4 10 parts of compound 1, 20 parts of compound A, 2 parts of sodium alkylnaphthalenesulfonate, 1 part of sodium ligninsulfonate, 5 parts of white carbon, diatomaceous earth 62
Parts and the above were uniformly stirred and mixed to obtain 100 parts of a wettable powder.

Formulation Example 5 0.3 part of Compound 1, 1 part of Compound A, and 0.3 part of white carbon are uniformly mixed, and 98.2 parts of clay and 0.2 part of Drilles A (manufactured by Sankyo) are added. And uniformly pulverized and mixed to obtain 100 parts of powder.

Formulation Example 6 2 parts of compound 1, 2 parts of compound B, white carbon 2
Parts, 2 parts of sodium ligninsulfonate and 92 parts of bentonite, and after uniformly pulverizing and mixing, water was added and kneaded,
The mixture was granulated and dried to obtain 100 parts of granules.

Formulation Example 7 2 parts of compound 1, 2 parts of compound C, white carbon 2
Parts, 2 parts of sodium ligninsulfonate and 92 parts of bentonite, and after uniformly pulverizing and mixing, water was added and kneaded,
The mixture was granulated and dried to obtain 100 parts of granules.

Formulation Example 8 2 parts of compound 1, 2 parts of compound D, white carbon 2
Parts, 2 parts of sodium ligninsulfonate and 92 parts of bentonite, and after uniformly pulverizing and mixing, water was added and kneaded,
The mixture was granulated and dried to obtain 100 parts of granules.

Formulation Example 9 10 parts of the compound 1, 40 parts of the compound B and 5 parts of a 20% aqueous solution of polyvinyl alcohol were sufficiently mixed with stirring.
45 parts of a 0.8% aqueous solution of xanthan gum was added and stirred and mixed again to obtain 100 parts of a flowable agent.

Formulation Example 10 2 parts of compound 1, 2 parts of compound, white carbon 2
Parts, 2 parts of sodium ligninsulfonate and 92 parts of bentonite, and after uniformly pulverizing and mixing, water was added and kneaded,
The mixture was granulated and dried to obtain 100 parts of granules.

Test Example 1 Effect on Emulsion (Spray Test) Emulsion prepared according to Formulation Examples 1 to 3 was used as an aqueous solution of a predetermined concentration, and three rice plants were planted three at a time in a Wagner pot (1/5000 are). (Variety: Koshihikari) was sprayed at 100 ml per 3 pots. One week later, a spore suspension of the rice blast fungus was spray-inoculated, cultivated under high humidity conditions, and the number of lesions was examined 10 days and 20 days after the inoculation. The control rate was calculated by the following equation (Equation 1).

[0036]

(Equation 1) Also, 10 and 20 days after inoculation, the rice was covered with a wire mesh cylinder, and 10 female adult female brown planthoppers were released into the inside.
After 48 hours, the mortality was investigated. The mortality is given by the following equation (Equation 2)
Was calculated by

[0037]

(Equation 2) The results are shown in Table 1 (Table 1).

[0038]

[Table 1]

Test Example 2 Test on Granules (Water Surface Treatment Test) A predetermined amount of the granules prepared according to Formulation Examples 6 to 8 was weighed, and 5 plants were planted three at a time in Wagner pots (1/5000 ares). It was applied to the water surface of paddy rice (variety: Koshihikari).
Five days later, a spore suspension of rice blast fungus was spray-inoculated, cultivated under high humidity conditions, and the number of lesions was examined on the 10th and 20th days after the chemical treatment. The control rate was calculated in the same manner as in Test Example 1. Also, 10 and 20 days after the treatment, the paddy rice was covered with a wire mesh cylinder, 10 female adult female brown planthoppers were released into the inside, and the mortality was examined 48 hours later. The results are shown in Table 2 (Table 2).

[0040]

[Table 2] *: Amount of drug substance per 10 ares

Test Example 3 Test on Granules (Sterling Box Treatment Test) Each of the granules prepared according to Formulation Examples 6 to 8 was treated in a seedling box (30 cm × 60 cm) of paddy rice (variety: Koshihikari) in an amount of 50 g each day, and the next day. Five plants were planted three at a time in Wagner pots (1/5000 ares). The next day, a spore suspension of rice blast fungus was spray-inoculated, cultivated under high humidity conditions, and 10 days after planting.
On days 20 and 20, the number of lesions was investigated. Test Example 1
It was calculated in the same manner as described above. Also, 10 and 20 days after the planting, the rice was covered with a wire mesh cylinder, 10 female adult female brown planthoppers were released into the inside, and the mortality was examined 48 hours later. The results are shown in Table 3 (Table 3).

[0042]

[Table 3]

Test Example 4 Effect of wettable powder (spray test) Rice sheath blight fungus cultivated at the base of rice (cultivar: Koshihikari) in which three plants were planted three in three in Wagner pots (1/5000 ares) After inoculation, the wettable powder prepared according to Formulation Example 4 was made into an aqueous solution of a predetermined concentration at an appropriate time when the sheath blight was transferred to the upper part of the rice body, and the solution was added to a Wagner pot (1/5000 ares).
100 ml per three pots was sprayed on paddy rice (variety: Koshihikari) in which five strains were planted. 20 days and 30 days after treatment
On the day, the rate of diseased strains and the rate of lesions were investigated. The damage degree and control value were calculated by the following formulas (Equations 3, 4, 5).

[0044]

[Equation 3] Sick spot height ratio = Top spot height (cm) ÷ Plant height (c)
m) x 100

[0045]

[Equation 4] Degree of damage = (1.62 × Sick spot high rate−32.4) ×
Disease rate: ¥ 100

[0046]

[Equation 5] Control value = 100− (Damage degree of treated area / Damage degree of untreated area × 100) Further, 20 and 30 days after spraying, paddy rice was covered with a wire mesh cylinder, and 10 female adult female brown planthoppers were placed inside. Let go,
After 48 hours, the mortality was investigated. At the same time, phytotoxicity was investigated. The results are shown in Table 4 (Table 4).

[0047]

[Table 4]

Test Example 5 Effect on Granules [0048] Rice seedling cultivation was inoculated at the root of a paddy rice (variety: Koshihikari) in which five strains were planted in three in Wagner pots (1/5000 ares). Granules (Compound 1: 2) prepared according to Formulation Example 10 at an appropriate time when the disease was transferred to the upper part of the rice body
%, Compound A: 2%). 20 days and 30 days after treatment
On the day, the rate of diseased strains and the rate of lesions were investigated. The degree of damage and the control value were calculated in the same manner as in Test Example 5. Also, 20 and 30 days after spraying, the rice was covered with a wire mesh cylinder, and 10 adult female brown planthoppers were released into the inside, and the mortality was examined 48 hours later. At the same time, phytotoxicity was investigated. The results are shown in Table 5 (Table 5).

[0049]

[Table 5]

Test Example 6 Effect on Granules (Seedling Box Test) 50 g of each of the granules prepared according to Formulation Examples 6 to 8 and 10 was applied to a nursery box of paddy rice (variety: Koshihikari), and the Wagner pot was prepared the next day. (1/5000 are) 3 by 5
The plant was planted. At 20, 40, 60 and 80 days after planting, the paddy rice was covered with a wire mesh cylinder, and 10 adult female brown planthoppers were released into the inside, and the mortality was examined 48 hours later (Equation 2). At the same time, phytotoxicity was investigated. The results are shown in Table 6 (Table 6).

[0051]

[Table 6]

[0052]

The insecticidal fungicidal composition of the present invention has excellent insecticidal and fungicidal effects, as is apparent from the above test results, is very useful for simultaneous control of insect pests and diseases, and has the number of treatments and application of pesticides. The dose can be reduced. Furthermore, the insecticidal fungicidal composition of the present invention can extend the residual effect as an insecticide, when used alone, does not cause harm to plants, and has low toxicity to warm-blooded animals. High safety. The nursery box treatment of paddy rice using the insecticidal / bactericidal composition of the present invention can simultaneously control pests and diseases for a long period of time, not only reducing the labor burden on farmers, but also reducing the amount of drug per unit area. And help reduce environmental impact. further,
Mixing with fertilizer and applying side-strip fertilization at the time of planting rice or planting, or formulating as a surfing agent or a throwing agent contributes to further labor saving. Therefore, the insecticidal fungicidal composition of the present invention is very effective for simultaneous control and labor saving of pests in agricultural and horticultural crops, and provides a remarkable technical advance in industrial effectiveness.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI (A01N 51/00 37:50) (A01N 51/00 43:82)

Claims (6)

[Claims] 1. A compound represented by the general formula (1): (Wherein, R1 is a hydrogen atom or a methyl group, R2 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R3 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R4 is a hydrogen atom or 1 to 5 carbon atoms. And (E) -2- {2- [6-
(2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate methyl, N-
[1- (2,4-Dichlorophenyl) ethyl] -2-cyano-3,3-dimethylbutanoic acid amide, 2- (E)-
At least one fungicidally active compound selected from methyl methoxyimino-2-[(2-methylphenoxy) methyl] phenylacetate or 7-thiomethoxycarbonyl-1,2,3-benzothiadiazole. A pesticidal fungicidal composition characterized by the following. 2. The compound represented by the general formula (1): The insecticidal composition according to claim 1, further comprising an insecticide compound (wherein, R1 is a hydrogen atom, R2 is a hydrogen atom, R3 is a methyl group, and R4 is a hydrogen atom). 3. The fungicidally active compound is (E) -2- ｛2-
The insecticidal / bactericidal composition according to claim 1 or 2, which is methyl [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate. 4. The fungicidally active compound is N- [1- (2,4)
-Dichlorophenyl) ethyl] -2-cyano-3,3-
The insecticidal / bactericidal composition according to claim 1 or 2, wherein the composition is dimethylbutanoic acid amide. 5. The insecticide according to claim 1, wherein the fungicidally active compound is methyl 2- (E) -methoxyimino-2-[(2-methylphenoxy) methyl] phenylacetate. Disinfecting composition. 6. The insecticidal fungicidal composition according to claim 1, wherein the fungicidally active compound is 7-thiomethoxycarbonyl-1,2,3-benzothiadiazole.