JP2990541B2 - Combined fungicide - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel composite fungicide having a fungicidal activity, comprising a known fungicidal carboxamide or its optical isomer and a known insecticidal carbamate compound.

[0002]

BACKGROUND OF THE INVENTION The bactericidal carboxamides and their optical isomers according to the present invention are known compounds described in JP-A-61-15867, JP-A-62-201855 and JP-A-2-11550. . Similarly, insecticidal compounds are available from The Pesticide Manual (the
Pestyside Manual) Eighth Edition 1987 (T
he British Crop Protection
n Council) or Agrochemical Handbook (1988)
Are known. In rice cultivation, mechanical transplantation is widely performed mainly by seedling transplanters. Simultaneous control of pests and crop diseases in paddy rice Honda, simultaneous control of pests and crop diseases by applying a nursery box of chemicals and labor saving. Is desired. In addition, reduction of the amount of pesticide used and the number of times of use are strongly desired from the viewpoint of safety and environmental protection, and the use of even lower amount of pesticide is being studied. Particularly in rice cultivation, for example, simultaneous control of important insect pests to be controlled, for example, Coleoptera pests (rice weevil, etc.), Hemiptera pests (hoppers, leafhoppers), and important disease to be controlled, potato disease, and labor saving And further improvement in safety aspects are expected.

[0003]

SUMMARY OF THE INVENTION As described above, the present invention is to realize the simultaneous control of desired pests and crop diseases in rice cultivation, and the use of such a drug at a lower dose. It is.

[0004]

Means for Solving the Problems The present inventors have calculated the formula:

Embedded image 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, Bactericidal carboxamides or optical isomers thereof, 2-isopropoxyphenyl methyl carbamate, o-cumenyl methyl carbamate, 2-se
c-butylphenyl methyl carbamate, 3,4-xylyl methyl carbamate, m-tolyl methyl carbamate, 3,5-xylyl methyl carbamate, 1
-Naphthyl methyl carbamate, 2,2-dimethyl-
1,3-benzodioxol-4-yl methylcarbamate, 2,3-dihydro-2,2-dimethylbenzofuran-7-ylmethylcarbamate, butyl 2,3-dihydro-2,2-dimethylbenzofuran-7-yl
N, N-dimethyl-N, N-thiodicarbamate, 2,
3-dihydro-2,2-dimethylbenzofuran-7-yl (dibutylaminothio) methyl carbamate, S-methyl N- (methylcarbamoyloxy) thioacetimidate, and ethyl N- [2,3-dihydro-2,
A novel composition comprising, as an active ingredient, at least one selected from the group of known insecticidal carbamate compounds consisting of 2-dimethylbenzofuran-7-oxycarbonyl (methyl) aminothio] -N-isopropyl-β-alaninate is excellent. Germicidal insecticidal activity.

According to the present invention, the compound fungicides of the present invention surprisingly and surprisingly surprisingly combine the fungicidal carboxamides of the formula (I) or their optical isomers and the known insecticidal compounds. Compared to the case of using each alone, of course, it enables simultaneous control of pests and crop diseases,
It exhibits a synergistic and synergistic effect by mixing, which is very unlikely to be expected from the effects of its use alone, whereby a particularly pronounced bactericidal and insecticidal effect can be achieved at lower doses. The complex fungicides of the present invention are particularly the main insect pests of rice, and the Hemiptera insecthoppers, leafhoppers and leafhoppers, which are resistant to existing drugs (organophosphorus and carbamate insecticides), Coleoptera pest rice weevil, etc.
It exerts an excellent and simultaneous effect on blast, which is the greatest disease against the lepidopteran insect pests such as the flea beetle and rice.

In the formula (I) of the fungicidally active ingredient in the composite fungicide of the present invention, preferably, Z represents chloro, R ¹ represents methyl, ethyl, n-propyl or isopropyl; ² represents a hydrogen atom or methyl, and R ³ represents a hydrogen atom or methyl.

Specific examples of the compound of the formula (II) include, for example, N- [1- (4-bromophenyl) -ethyl] -2,
2-dichloro-1,3,3-trimethylcyclopropanecarboxamide, N- [1- (4-chlorophenyl)-
Ethyl] -2,2-dichloro-1,3,3-trimethylcyclopropanecarboxamide, 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-
Mixture of diastereomers of 1r-cyclopropanecarboxamide, mixture of diastereomers of N- (R)-[1- (4-chlorophenyl) -ethyl] -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.

In the present invention, the weight ratio between the fungicidal compound group and the pesticidal compound group in the composite fungicide can be varied within a relatively wide range. In general, 1 to 20 parts by weight, preferably 1 to 10 parts by weight, of known insecticidal compounds are used per part by weight of the fungicidal carboxamides of the active compound formula (I) or their optical isomers. However, the weight ratios listed here depend on the extent of the occurrence of the pests and diseases.
It can be changed as needed. The combined bactericidal insecticide according to the present invention exhibits excellent bactericidal and insecticidal activity, and can be used as a bactericidal insecticide, for example, by foliage application, underwater or water application, soil application, soil mixing treatment, nursery box application, and the like. The combined fungicidal insecticides according to the present invention exhibit a strong fungicidal insecticidal action. Therefore, it can be used as a bactericidal insecticide. The active compound according to the present invention has no phytotoxicity to cultivated plants and low toxicity to warm-blooded animals, and is useful for pests in agriculture, especially in protection of rice,
In particular, it can be used to precisely control pests and diseases. They are usually active against sensitive and resistant species, and at all or some stages of development. Examples of the above-mentioned pests (disease and pests) include the following. Examples of such pests include the following pests.

[0009] Diseases include Plasmodiophoromycetes
(Coleoptera), Oomycetes (Oomycetes), Chytridiomycetes
(Acupuncture), Zygomycetes (Zygomycetes), Ascomycete
s (Ascomycetes), Basidiomycetes (Basidiomycetes), Deuterom
ycetes (incomplete fungi). In particular, rice blast fungus (Pyricularia oryzae) belonging to imperfect fungi
Can be mentioned as a bactericidal spectrum of the composite bactericidal insecticide of the present invention. As insects, Coleoptera insects, for example, rice weevil (Lissorhoptrus oryzophilus), rice weevil (Echinocinemus squameus), rice weevil (Oulema oryzae); lepidoptera, for example, Chilo suppressalis, Cnaphalocr
ocis medinalis), Naranga aenescen
s), Ichinomidiseseri (Parnaraguttata); Hemiptera, for example, Nephotettix cincticep
s), brown planthopper (Nilaparvatalugens), brown planthopper (Laodelphax striatellus), brown planthopper (So
gatella furcifera), green stink bug (Nezara spp.)
Orthoptera, for example, Kera (Gryl-lotalpa africana)
Locust (Locusta migratoria migratoriodes); and the like.

[0010] The complex fungicide of the present invention can be made into a usual preparation form as a mixed composition containing an active compound of the formula (I) and a known insecticidal compound as active ingredients. And such forms include solutions, emulsions, suspensions, powders, wettable powders, foams, pastes, granules, active compound infiltration-natural and synthetic, microcapsules, seed coatings,
And ULV (cold mist, warm mist) can be mentioned. These preparations can be manufactured by a known method. Such a method is
For example, the active compounds are mixed with a spreading agent, ie, a liquid diluent; a solid diluent, or a carrier, optionally with a surfactant, ie, an emulsifier and / or dispersant and / or a foam former. It can be done by doing. If water is used as the spreading agent, for example, organic solvents can also be used as auxiliary solvents. As the liquid diluent or carrier, for example, aromatic hydrocarbons (eg, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg,
Chlorobenzenes, ethylene chlorides, methylene chloride, etc.), aliphatic hydrocarbons (eg, cyclohexane, etc., paraffins (eg, mineral oil fractions, etc.)), alcohols (eg, butanol, glycol and their ethers)
Esters), ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), strong polar solvents (eg, dimethylformamide, dimethylsulfoxide, etc.) and water.

Examples of the solid diluent include soil natural minerals (eg, kaolin, clay, talc, chalk, quartz, attapull guide, montmorillonite, and diatomaceous earth), and soil synthetic minerals (eg, 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 the emulsifier and / or foaming agent include nonionic and anionic emulsifiers [eg, polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (eg, alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates). , 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. Coloring agents can also be used, such as inorganic pigments (eg, 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, copper, cobalt, molybdenum, zinc and their salts such as zinc. The preparation may, for example, contain the active ingredient in an amount of 0.1-9.
5% by weight, preferably 0.5 to 90% by weight.

The complex fungicides of the present invention can be used in their commercially useful formulations and in the use forms prepared by these formulations to provide other active compounds such as insecticides, fungicides, fungicides, They can also be present as admixtures with growth regulators or herbicides. Here, examples of the insecticide include organophosphorus agents, carbamates, carboxylates, chlorinated hydrocarbons, and insecticides produced by microorganisms. Furthermore, the complex fungicide of the present invention can also be present as a mixture with a synergist, and such preparations and forms of use include those that are commercially useful. The synergist is itself a compound that need not be active but amplifies the action of the active compound. The content of the composite fungicides of the present invention in commercially useful forms of use can vary within wide limits. The use concentration of the combined fungicide of the present invention is, for example, 0.00001 to 100% by weight, preferably 0.001 to 5% by weight. The combined germicidal insecticide of the present invention can be used in a usual manner suitable for the use form.

[0013] The active compound of the formula (I) and the known insecticidal compound are used in the form of a so-called tank mix which can be mixed and used in actual use. Is also included. EXAMPLES The content of the present invention will be specifically described with reference to examples, but the present invention should not be limited to these.

[0014]

EXAMPLES Biological tests:-Test compounds 1: N- [1- (4-chlorophenyl) -ethyl]
-2,2-dichloro-1,3,3-trimethylcyclopropanecarboxamide 2: N- [1- (4-chlorophenyl) -ethyl]
-2,2-Dichloro-1-ethyl-3-methylcyclopropanecarboxamide 3: N- [1- (4-chlorophenyl) -ethyl]
-2,2-dichloro-1-isopropylcyclopropanecarboxamide 4: N- (R)-[1- (4-chlorophenyl)-
Mixture of diastereomers of [ethyl] -2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropanecarboxamide. 5: N- (R)-[1- (4-chlorophenyl)-
Ethyl]-(1S) -2,2-dichloro-1-ethyl-
3t-methyl-1r-cyclopropanecarboxamide 6: N- [1- (4-bromophenyl) -ethyl]
-2,2-dichloro-1,3,3-trimethylcyclopropanecarboxamide 7: N- (R)-[1- (4-chlorophenyl)-
Mixture of diastereomers of [ethyl] -2,2-dichloro-1-isopropylcyclopropanecarboxamide

A: 2-isopropoxyphenyl methyl carbamate B: o-cumenyl methyl carbamate C: 2-sec-butylphenyl methyl carbamate D: 3,4-xylyl methyl carbamate E: m-tolyl methyl carbamate F: 2,3 -Dihydro-2,2-dimethylbenzofuran-7-yl methyl carbamate G: 2,3-dihydro-2,2-dimethylbenzofuran-7-yl (dibutylaminothio) methyl carbamate H: ethyl N- [2,3 -Dihydro-2,2-dimethylbenzofuran-7-oxycarbonyl (methyl) aminothio] -N-isopropyl-β-alaninate I: 2,2-dimethyl-1,3-benzoxol-4-
Il methyl carbamate

Test Example 1 Test of foliar spraying effect Preparation of test compound Active compound: 30 to 40 parts by weight Carrier: 55 to 65 parts by weight of a mixture of diatomaceous earth and kaolin (1: 5) Emulsifier: polyoxyethylene alkylphenyl 5 parts by weight of ether The above-mentioned amounts of the active compound, the carrier and the emulsifier are pulverized and mixed to obtain each wettable powder, and the mixture is prepared by diluting a predetermined amount of the water with water and mixing.

(I) Test on brown planthopper Test method: Three rice plants having a plant height of about 15 cm were planted in a pot having a diameter of about 13 cm, and 10 days after planting, a water dilution of a predetermined concentration of the active compound prepared in advance using a spray gun was used. After spraying the sprayed drug solution and air-drying it, the pot was covered with a net basket, and 4th-instar larvae of the organophosphate resistant strain, brown planthopper, were found.
Ten animals were inoculated per pot, and three days later, dead insects were counted and the insecticidal rate was calculated.

(Ii) Efficacy test of foliage application on rice blast Test method: Paddy rice (cultivar: Asahi) is grown in a clay pot having a diameter of 12 cm, and a predetermined concentration dilution of the active compound prepared beforehand in the 3-4 leaf stage Was sprayed at a rate of 50 ml per three pots. Spray inoculation of the suspension of rice blast spores artificially cultured the next day (twice)
Then, the cells were infected in a moist chamber at 25 ° C. and 100% relative humidity. Seven days after inoculation, the degree of illness per pot was categorized and evaluated according to the following criteria, and the control value (%) was determined. At the same time, phytotoxicity was investigated.

Degree of morbidity Lesion area percentage (%) 0.0 Less than 0.5 2 Less than 2 to 5 Less than 5 to 10 3 Less than 10 to 20 4 Less than 20 to 40 540 or more

(Equation 1) This test is the result of 3 pots per section. The results of the tests (i) and (ii) are summarized and shown in Table 1.

[0020]

[Table 1]

Test Example 1 Nursery Box Application Efficacy Test Preparation of test compounds: 5 (or 2) parts of active compound, 30 parts of bentonite (montmorillonite), 6 parts of talc (talc)
To a mixture of 3 parts (or 66 parts) and 2 parts of ligninsulfonate, 25 parts of water is added and kneaded well. The mixture is extruded into granules of 10 to 40 mesh by an extruder and dried at 40 to 50 ° C to obtain granules. Agent. Nursery box (30cm x 60cm x
The seedlings 21 days after germination, planted at 2 cm), were treated with granules of 5% of an insecticidal compound and granules of 2% of a fungicidal compound, respectively.
A predetermined amount was uniformly applied, and after the application, three rice seedlings were taken out together with the soil and transplanted into a pot in a 1 / 10000a greenhouse. Three days after the transplantation, the pot was covered with a plastic net cage, and the fourth-instar larvae of the organic phosphorus-resistant line Leafhopper leafhopper were released 10 per pot, and two days after release, the number of dead insects was counted to calculate the insecticidal rate. Further, after the rice seedlings are colored and grow well on the 20th day of planting, a suspension of rice blast spores is spray-inoculated by a conventional method, and the suspension is inoculated at a temperature of 23 to 25 ° C and a relative humidity of 100%. Hold for 24 hours. After that, it was transferred to a glass greenhouse at a temperature of 20 to 28 ° C., and 7 days after inoculation, the degree of disease per pot was classified and evaluated in the same manner as in Test Example 1, and the control value (%) was determined. At the same time, phytotoxicity was investigated. Table 2 shows the results.

[0022]

[Table 2]

[0023]

Industrial Applicability As shown in the above Examples, the composite fungicide of the present invention exhibits excellent control action against pests and diseases, and exhibits a composite composition which is more effective than the concentration when a single drug is used. Shows an effective control effect at lower concentrations.

Continuation of front page (58) Field surveyed (Int.Cl. ⁶ , DB name) A01N 53/12 A01N 47/10

Claims (2)

(57) [Claims] (1) Formula (1): 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, Bactericidal carboxamides or optical isomers thereof, 2-isopropoxyphenyl methyl carbamate, o-cumenyl methyl carbamate, 2-se
c-butylphenyl methyl carbamate, 3,4-xylyl methyl carbamate, m-tolyl methyl carbamate, 3,5-xylyl methyl carbamate, 1
-Naphthyl methyl carbamate, 2,2-dimethyl-
1,3-benzodioxol-4-yl methylcarbamate, 2,3-dihydro-2,2-dimethylbenzofuran-7-ylmethylcarbamate, butyl 2,3-dihydro-2,2-dimethylbenzofuran-7-yl
N, N-dimethyl-N, N-thiodicarbamate, 2,
3-dihydro-2,2-dimethylbenzofuran-7-yl (dibutylaminothio) methyl carbamate, S-methyl N- (methylcarbamoyloxy) thioacetimidate, and ethyl N- [2,3-dihydro-2,
A composite bactericidal insecticidal composition comprising, as an active ingredient, at least one member selected from the group of known insecticidal carbamate compounds consisting of 2-dimethylbenzofuran-7-oxycarbonyl (methyl) aminothio] -N-isopropyl-β-alaninate. Agent. 2. The bactericidal carboxamide or its optical isomer is N- [1- (4-bromophenyl) -ethyl].
-2,2-dichloro-1,3,3-trimethylcyclopropanecarboxamide, N- [1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1,3,3-trimethylcyclopropanecarboxamide, 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)-
A mixture of diastereomers of ethyl] -2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropanecarboxamide, N- (R)-[1- (4-chlorophenyl) -ethyl] -2, A mixture of diastereomers of 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.