JPH09315906A - Fungicidal and insecticidal composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new fungicidal and insecticidal composition capable of simultaneously controlling insect pests and crop diseases and showing extremely excellent effects by synergistic effects with a small amount, by combining a specific fungicidal carboxamide with a prescribed insecticidal compound. SOLUTION: This composition comprises a fungicidal carboxamide of the formula (Z is a halogen; R<1> is an alkyl; R<2> is H, methyl, etc.; R<3> is H or methyl) or its optical isomer and one compound selected from the group consisting of (E)-4,5-dihydro-6-methyl-4-(3-pyridylmeethyleneamino)-1,2,4-triazin-3( 2H)-one, 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethyl) sulfinyl-1H- pyrazole-3-carbonitrile, a bisaroylhydrazide derivative, etc. The blending ratio of the former is about 0.1-10 pts.wt., especially preferably about 0.2-5 pts.wt. of the insecticidal compound based on 1 pt.wt. of the compound of the formula.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a germicidal and insecticidal composition. Specifically, it relates to a novel bactericidal and insecticidal mixed composition containing known bactericidal carboxamides and known bactericidal compounds.

[0002]

PRIOR ART AND PROBLEMS TO BE SOLVED BY THE INVENTION JP-A-61-15867 and JP-A-62-20 known from the filing date of the present application.
1855 and JP-A-2-11550 describe fungicidal carboxamides related to the composition of the present invention. Also, similarly known Japanese Patent Laid-Open No. 63-3167.
71, JP-A-3-157308, JP-A-5-163.
No. 266, JP-A-6-192014, and JP-A-7-16.
No. 5508, No. 2-171 and No. 6-776
The publication describes insecticidal compounds relating to the compositions of the invention. In recent years, rice cultivation has been widely carried out by mechanical transplantation using a seedling transplanter. In addition to simultaneous control of pests and crop diseases in paddy rice Honda, simultaneous control and labor saving of pests and crop diseases by application of a nursery box of chemicals are required. Is desired. Also,
From the viewpoints of safety and environmental protection, reduction in the amount and frequency of use of pesticides is strongly desired, and the use of even lower doses is being studied. Particularly, it is an important pest to be controlled in rice cultivation, for example, Lepidoptera pests (Meigas),
Simultaneous control, labor saving and further improvement in safety of pests of the order Coleoptera (rice weevil, etc.), pests of the order Hemiptera (planthopper, leafhoppers) and blast, which is an important disease to be controlled, are expected to be further improved.

[0003]

[Means for Solving the Problems]
formula:

Embedded image (In the formula, Z represents a halogen atom, and R ¹ has 1 to 4 carbon atoms.
R ² is a hydrogen atom, a methyl group or an ethyl group, and R ³ is a hydrogen atom or a methyl group. ), A bactericidal carboxamide or an optical isomer thereof, and (E) -4,5-dihydro-6-methyl-4- (3-pyridylmethyleneamino) -1,2,4 as an insecticidal compound. -Triazine-3 (2H) -one, 5
-Amino-1- [2,6-dichloro-4- (trifluoromethyl) phenyl] -4- (trifluoromethyl) sulfinyl-1H-pyrazole-3-carbonitrile,
N- (6-chloro-3-pyridylmethyl) -N-ethyl-N'-methyl-2-nitrovinylidene diamine, 1-
(2-chloro-5-thiazolylmethyl) -3-methyl-
2-nitroguanidine, 1- (2-chloro-5-thiazolylmethyl) -3,5-dimethyl-2-nitroimino-
A novel mixed composition comprising, as an active ingredient, a compound selected from the group consisting of hexahydro-1,3,5-triazine and a bisaroylhydrazide derivative exhibits a particularly excellent fungicidal and insecticidal action. Found out.

According to the present invention, the fungicidal and insecticidal composition of the present invention is surprisingly characterized by the fact that the fungicidal carboxamides of the formula (I) and the abovementioned insecticidal compounds are used alone in comparison with pests and insecticides. Not only it enables simultaneous control of crop diseases, but it also shows a synergistic and synergistic effect due to the mixture, which cannot be predicted from the effect of crops when used alone, whereby a particularly remarkable fungicidal and insecticidal composition can be obtained at a lower dose. You can reveal things. The bactericidal and insecticidal composition of the present invention is a rice blast, which is the largest disease of rice, and an important insect pest of rice, and has acquired resistance to existing drugs (organophosphorus and carbamate insecticides). It is possible to simultaneously and accurately exhibit an excellent control effect on the plant pests of the eye pests such as planthoppers and leafhoppers, the pod weevil Weevil Weevils, and the lepidopteran pests of the leaf moth, Meichus. Of the active ingredients in the fungicidal and insecticidal composition of the present invention, the fungicidal carboxamides of the formula (I) are preferably Z in the formula (I), Z is chlorine and R ¹ is ethyl or isopropyl. , R ²
Represents a hydrogen atom or methyl, and R ³ represents a hydrogen atom.

Specific examples of the compound of formula (I) include, for example, N- [1- (4-chlorophenyl) -ethyl]-
2,2-Dichloro-1-ethyl-3-methylcyclopropanecarboxamide, N- [1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-isopropylcyclopropanecarboxamide, N- (R)- [1-
(4-chlorophenyl) -ethyl] -2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropanecarboxamide diastereomeric mixture, N-
(R)-[1- (4-chlorophenyl) -ethyl]-
Mixture of diastereomers of 2,2-dichloro-1-isopropylcyclopropanecarboxamide, N-
(R)-[1- (4-chlorophenyl) -ethyl]-
(1S) -2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropanecarboxamide, and N-
(R)-[1- (4-chlorophenyl) -ethyl]-
(1S) -2,2-dichloro-1-isopropylcyclopropanecarboxamide can be exemplified, and these compounds are described in JP-A Nos. 61-15867 and 62-20185.
Known compounds described in JP-A No. 5-11550 and JP-A No. 2-11550.

The other active ingredient in the fungicidal and insecticidal composition of the present invention, the insecticidal compound, is a known compound described in the above publications. In the present invention, the weight ratio of each group of active compounds in the mixed composition can be varied within a relatively wide range. Generally, about 0.1 part of the insecticidal compound per part by weight of the fungicidal carboxamides of formula (I).
It can be used in the range of 1 to 10 parts by weight, preferably about 0.2 to 5 parts by weight. However, the weight ratios mentioned here can be changed as necessary depending on the degree of occurrence of pests and diseases. The active substance combinations according to the invention show an excellent fungicidal and insecticidal activity, and as fungicidal insecticides, for example, foliar application, application in water or on water,
It can be used by applying soil, mixing soil, applying nursery box, and the like. The active substance combinations according to the invention exhibit a strong bactericidal and insecticidal action. Therefore, it can be used as a germicidal insecticide. The mixed composition of the present invention has no phytotoxicity to cultivated plants, and has low toxicity to warm-blooded animals, and controls pests in agriculture, particularly rice protection, particularly pests and pests. Can be used for They are usually active against sensitive and resistant species, and at all or some stages of development.

As the above-mentioned pests (disease and pest),
For example: Examples of such pests include the following pests.
As insects, pests of the order Coleoptera, for example, weevils (Lissorhoptrus oryzophilus), weevils (Echino)
cinemus squameus), rice leaf beetle (Oulema ory)
zae); Lepidoptera, for example, Chilo suppre
ssalis), Cobb Nomeiga (Cnaphalocrocis medinalis)
, Naranga aenescens, Ichon disguise (Parnara guttata); Hemiptera, such as the leafhopper (Nephotettix cincticeps), the brown planthopper (Nilaparvatalugens), the brown planthopper (Laodelphax)
striatellus), White-faced planthopper (Sogatella furcifer)
a), Stink bug (Nezara spp.); Orthoptera, for example, kerula (Gryl-lotalpa africana), grasshopper (Locustamigrato)
ria migratoriodes); Diseases include, for example, archaebacteria [Archimycetes], algae [Phycomycetes], and ascomycetes [Ascomycetes].
comycetes)], basidiomycetes (Basidiomyc
etes)], an incomplete bacterium [Fungi Im Perfection (Fu
ngi Imperfecti)], various plant diseases caused by other bacteria, and the like. Typical examples of the sterilization spectrum of the above plant diseases include rice blast fungus (Pyri)
cularia oryzae) and the like.

The active substance combinations according to the invention can be in the form of mixtures of the fungicidal carboxamides of the formula (I) and of the insecticidal compounds or else in the customary formulations for mixing at the place of application. And as such a form, mention may be made of solutions, emulsions, suspensions, powders, wettable powders, foams, pastes, granules, aerosols, active compound infiltration-natural and synthetic products, microcapsules, seed coating agents. You can These preparations can be manufactured by a known method. Such methods include, for example, applying the active compound to a spreading agent,
Liquid diluents; solid diluents or carriers, optionally surfactants, ie emulsifiers and / or dispersants and / or
Alternatively, it can be carried out by mixing with a foam forming agent. If water is used as the spreading agent, for example, organic solvents can also be used as auxiliary solvents.

Examples of the liquid diluent or carrier include aromatic hydrocarbons (eg, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg, chlorobenzenes, ethylene chloride). , Methylene chloride, etc.), aliphatic hydrocarbons [eg, cyclohexane etc., paraffins (eg mineral oil fractions etc.)], alcohols (eg butanol, glycol and their ethers, esters etc.), ketones (eg , Acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), strong polar solvent (eg, dimethylformamide, dimethyl sulfoxide, etc.)
And we can mention water. As a solid diluent,
Soil natural minerals (for example, kaolin, clay, talc, chalk, quartz, attapal guide, montmorillonite, diatomaceous earth, etc.), soil synthetic minerals (for example, highly dispersed silicic acid,
Alumina, silicate, etc.). Solid carriers for granules include crushed and fractionated rocks (eg, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic granules of inorganic and organic flours, and organic granules (eg, , Sawdust, coconut, corn cob and tobacco stem).

Examples of emulsifiers and / or foaming agents include nonionic and anionic emulsifiers [eg polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (eg alkylaryl polyglycol ethers, alkyl sulfonates, Alkylsulfates, arylsulfonates, etc.)], and albumin hydrolysis products. Dispersants include, for example, lignin sulfite waste liquors and methylcellulose. Fixatives can also be used in the formulation (powder, granules, emulsions) and include carboxymethylcellulose and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate. Can be. Colorants can also be used, such as inorganic pigments (for example iron oxide, titanium oxide and Prussian blue) and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes, and also iron. , Manganese, boron,
Trace elements can be mentioned, such as their salts of copper, cobalt, molybdenum, zinc.

The preparation may contain, for example, 0.1% of the active ingredient.
˜95 wt%, preferably 0.5 to 90 wt%. The fungicidal and insecticidal compositions according to the invention are those commercially useful formulations and the use forms prepared according to these formulations, in addition to other active compounds, for example insecticides,
It can also be present as a mixture with fungicides, fungicides, growth regulators or herbicides. Here, as the insecticide, for example, organic phosphorus agents, carbamate agents, nitromethylene-based agents, nitroguanidine-based agents, cyanoguanidine-based agents, carboxylate-based agents, chlorinated hydrocarbon-based agents, produced from microorganisms. Insecticides can be mentioned. Furthermore, the mixed composition of the present invention can also be present as an admixture with a synergist, and such formulations and use forms can include those which are commercially useful. The synergist need not be active per se, but is a compound which amplifies the action of the active compound. The content of the mixed compositions according to the invention in the commercially useful use forms can be varied within wide limits. The use concentration of the mixed composition of the present invention is
For example, 0.00001 to 100% by weight, preferably
It is 0.001 to 5% by weight. The mixed composition of the present invention can be used by a usual method suitable for the use form.

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION Next, the contents of the present invention will be described in detail with reference to Examples, but the present invention should not be limited thereto.

[0013]

【Example】

Biological test: Test compound I. 1: N- [1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-ethyl-3-methylcyclopropanecarboxamide I. 2: N- (R)-[1- (4-chlorophenyl)
-Ethyl] -2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropanecarboxamide diastereomeric mixture I. 3: N- (R)-[1- (4-chlorophenyl)
-Ethyl]-(1S) -2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropanecarboxamide A: 5-amino-1- [2,6-dichloro-4- (trifluoromethyl) phenyl ] -4- (Trifluoromethyl) sulfinyl-1H-pyrazole-3-carbonitrile B: N- (6-chloro-3-pyridylmethyl) -N-
Ethyl-N'-methyl-2-nitrovinylidene diamine C: 1- (2-chloro-5-thiazolylmethyl) -3
-Methyl-2-nitroguanidine D: 1- (2-chloro-5-thiazolylmethyl)-
3,5-Dimethyl-2-nitroimino-hexahydro-
1,3,5-Triazine E: N- (3-methoxy-2-methylbenzoyl)-
N '-(3,5-dimethylbenzoyl) -N'-tert-
Butylhydrazine

Example 1 Preparation of test compound Each active compound: 5 to 25 parts by weight Carrier: Mixture of diatomaceous earth and kaolin (1: 5) 70
Parts by weight to 90 parts by weight Emulsifier: polyoxyethylene alkylphenyl ether 5 parts by weight The above-mentioned amounts of the active compound, carrier and emulsifier are pulverized and mixed into each wettable powder, and the predetermined amount thereof is diluted with water and mixed. Prepared. Surface application efficacy test Test method Paddy rice (cultivar: Asahi) is planted in a white porcelain pot with a diameter of 12 cm in 3 strains and submerged, and a chemical solution of a predetermined concentration prepared in the early stage of tillering is used directly on the rice paddy field. Irrigation was performed on the water surface so that the indicated dose was obtained so as not to cover the area.
Three days after that, a netted basket was applied to inoculate 10 fourth-instar larvae of the brown planthopper per pot, and two days after the inoculation, dead insects were counted and the insecticidal rate was calculated. In addition, 20 days after the drug treatment, a suspension of rice blast fungus spores is sprayed and inoculated by a conventional method at a temperature of 23 to 25.
It was kept in an inoculation room at ℃ and 100% relative humidity for 24 hours. Then, it was transferred to a glass greenhouse at a temperature of 20 to 28 ° C., and 7 days after the inoculation, the degree of disease per pot was classified and evaluated according to the following criteria, and the control value (%) was determined. The phytotoxicity was also investigated simultaneously.

[0015]

[Table 1] Degree of morbidity Disease area ratio (%) 0 0 less than 0.5 2 1 less than 2 5 less than 2 5 less than 10 3 less than 10 20 4 less than 20 40 less than 540

[0016]

[Equation 1]

This test is a result of 3 pots in 1 ward. The results are shown in Table 1.

[0018]

[Table 2]

[0019]

[Table 3]

No chemical damage was observed in each test section.

Example 2 Stem and leaf spraying efficacy test (i) Test against brown planthopper Preparation of test compound Each active compound: 30 to 40 parts by weight Carrier: Mixture of diatomaceous earth and kaolin (1: 5) 55
Parts by weight to 65 parts by weight Emulsifier: polyoxyethylene alkylphenyl ether 5 parts by weight The above-mentioned amounts of the active compound, carrier and emulsifier are ground and mixed into each wettable powder, and the predetermined amount thereof is diluted with water and mixed. Prepared. Test method: 3 rice plants with a plant height of about 15 cm were planted in a pot with a diameter of about 13 cm, and 10 days after planting, 20 ml of a diluted water solution of a predetermined concentration of the active compound prepared in advance was sprayed with a spray gun and sprayed. After air-drying the drug solution, a net was applied to the pot, and 10 fourth-instar larvae of the brown planthopper were inoculated per pot, and after 3 days, dead insects were counted and the insecticidal rate was calculated. (Ii) Test for Cobb Nosame moth: Similar to the test for the brown planthopper (i) above, the test rice was sprayed with the chemical solution, and after air-drying, the leaf blade part was cut into about 4 cm, and
Eight pieces were placed in a petri dish lined with wet filter paper, 10 second-instar larvae of Cobb Nomeiga were released per petri dish, and 4 days later, dead insects were counted and the insecticidal rate was calculated. (iii) Foliar spraying efficacy test for rice blast test method Paddy rice (cultivar: Asahi) was cultivated in a clay pot with a diameter of 12 cm, and a diluted solution of a predetermined concentration of the active compound prepared in advance in 3 to 4 leaf stages was added per 3 pots. 50 ml was sprayed. Next day, spray-inoculate (twice) a suspension of rice blast fungus spores artificially cultured, and
The specimen was kept in a humid chamber at ℃ and 100% relative humidity for infection. Seven days after the inoculation, the degree of disease per pot was classified and evaluated according to the following criteria, and the control value (%) was determined. The phytotoxicity was also investigated simultaneously.

[0022]

[Table 4] Susceptibility Disease area ratio (%) 0 0 less than 0.5 2 1 less than 2 5 less than 2 5 less than 10 3 less than 10 20 4 less than 20 40 less than 540

[0023]

[Equation 2]

This test is a result of 3 pots in 1 ward. The results of the tests (i), (ii) and (iii) are summarized and shown in Table 2.

[0025]

[Table 5]

[0026]

[Table 6]

No chemical damage was observed in each test section.

Example 3 Nursery box application efficacy test Preparation of test compound: 25 parts of water was added to a mixture of 2 parts of active compound, 30 parts of bentonite (montmorillonite), 66 parts of talc (talc) and 2 parts of lignin sulfonate. The mixture was kneaded well, granulated with an extrusion granulator to 10 to 40 mesh, and dried at 40 to 50 ° C to obtain a granule. For seedlings 21 days after germination planted in a nursery box (30 cm × 60 cm × 2 cm), 50 g per box of the fungicidal carboxamides of the formula (I) prepared above and granules of an insecticidal compound Was uniformly applied to each box at 25 g, and after the application, three rice seedlings were extracted together with the soil and transplanted into a pocket in a greenhouse of 1 / 10000a. Three days after transplantation, the pot was covered with a plastic net basket, 10 fourth-instar larvae of the brown planthopper were released per pot, and two days after the release, the number of dead insects was counted and the insecticidal rate was calculated. Furthermore, after 20 days of planting, the rice seedlings have been colored and have become well grown, and then a suspension of rice blast fungus spores is sprayed and inoculated by a conventional method into an inoculation room at a temperature of 23 to 25 ° C. and a relative humidity of 100%. I kept it for 24 hours. Then, it was transferred to a glass greenhouse at a temperature of 20 to 28 ° C., and 7 days after the inoculation, the degree of disease per pot was classified and evaluated according to the following criteria, and the control value (%) was determined. The phytotoxicity was also investigated simultaneously.

[0029]

[Table 7] Degree of morbidity Disease area ratio (%) 0 0 less than 0.5 2 1 less than 2 5 less than 25 less than 10 3 less than 10 20 4 less than 40 less than 540 more than 40

The results are shown in Table 3.

[0031]

[Table 8]

[0032]

[Table 9]

No chemical damage was observed in each test section.

Example 4 (Wettable powder) 25 parts of the insecticidal compound C, 25 parts of a fungicidal carboxamide of the formula (I), 45 parts of a mixture of powdered diatomaceous earth and powdered clay (1: 5), sodium alkylbenzene sulfonate 2 parts and 3 parts of sodium alkylnaphthalene sulfonate formalin condensate were ground and mixed to obtain a wettable powder.

Example 5 (Granule) 3 parts of the insecticidal compound D, 3 parts of bactericidal carboxamides of the formula (I), bentonite (montmorillonite) 30
Part, talc (talc) 62 parts, and lignin sulfonate 2 parts, 25 parts of water was added, kneaded well, and granulated with an extrusion-type granulator to give particles of 10-40 mesh, 40-
It was dried at 50 ° C to obtain granules.

Continuation of the front page (51) Int.Cl. ⁶ Identification number Office reference number FI technical display area A01N 43:36 43:40 47:44 43:78) C07M 7:00

Claims (2)

[Claims] 1. The formula: (In the formula, Z represents a halogen atom, R ¹ represents an alkyl group having 1 to 4 carbon atoms, R ² represents a hydrogen atom, a methyl group or an ethyl group, and R ³ represents a hydrogen atom or a methyl group. ), A bactericidal carboxamide or an optical isomer thereof, and (E) -4,5-dihydro-6-methyl-4 as an insecticidal compound.
-(3-Pyridylmethyleneamino) -1,2,4-triazin-3 (2H) -one, 5-amino-1- [2,6
-Dichloro-4- (trifluoromethyl) phenyl]-
4- (trifluoromethyl) sulfinyl-1H-pyrazole-3-carbonitrile, N- (6-chloro-3-
Pyridylmethyl) -N-ethyl-N'-methyl-2-nitrovinylidene diamine, 1- (2-chloro-5-thiazolylmethyl) -3-methyl-2-nitroguanidine,
1- (2-chloro-5-thiazolylmethyl) -3,5-
Dimethyl-2-nitroimino-hexahydro-1,3,
A fungicidal and insecticidal composition comprising, as an active ingredient, a compound selected from the group consisting of 5-triazine and a bisaroylhydrazide derivative. 2. The bactericidal carboxamides are N- [1-
(4-Chlorophenyl) -ethyl] -2,2-dichloro-1-ethyl-3-methylcyclopropanecarboxamide, N- [1- (4-chlorophenyl) -ethyl]-
2,2-dichloro-1-isopropylcyclopropanecarboxamide, N- (R)-[1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-ethyl-3t
-Methyl-1r-cyclopropanecarboxamide diastereomeric mixture, N- (R)-[1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-isopropylcyclopropanecarboxamide diastereomer Mixtures of N- (R)-[1- (4-chlorophenyl) -ethyl]-(1S) -2,2-dichloro-1
-Ethyl-3t-methyl-1r-cyclopropanecarboxamide and N- (R)-[1- (4-chlorophenyl) -ethyl]-(1S) -2,2-dichloro-1-isopropylcyclopropanecarboxamide The bactericidal / insecticidal composition according to claim 1, which is one of the following: