KR0168853B1 - Fungicidal and insecticidal composition - Google Patents

Abstract

A novel fungicidal and pesticidal composition comprising a carboxamide represented by the following general formula (I) or an optical isomer thereof and at least one pesticidal active substance.

Where

Z represents a halogen atom,

R ¹ represents a C _1-4 alkyl group,

R ² represents a hydrogen atom, a methyl group or an ethyl group,

R ³ represents a hydrogen atom or a methyl group.

Description

[Name of invention]

Fungicidal and Insecticidal Compositions

Detailed description of the invention

The present invention relates to novel synergistic fungicidal and pesticidal active substance combinations containing known fungicidally active carboxamides or known optical isomers thereof and known pesticidal active compounds.

It is already known that certain groups of carboxamides have fungicidal activity (see Japanese Patent Laid-Open Nos. 15867/1986, 201855/1987 and 11550/1990).

In rice cultivation, mechanical transplanting method using young seedlings has been widely used in recent years. In addition to simultaneous control of paddy pests and crop diseases, insecticides are applied to the mother beds to simultaneously control pests and crop diseases, as well as to apply pesticides. There has been a strong demand for reducing labor for the workforce.

There is a strong need for substantial reductions in pesticides not only in the amount of use but also in the number of applications for biological safety and environmental protection, which further requires extensive research to minimize the dosage.

In particular, planthoppers and leafhoppers belonging to the group of Hemiptera, such as Lysorhoptrus, belonging to the tree of Coleoptera, a very important control pest, There is a strong demand for simultaneous control of pests and fungi, labor savings in control operations, and even more improved biological safety in relation to blasting, a very important control disease.

According to the present invention, the carboxamide represented by the following general formula (I) or its optical isomer and S, S '-(2-dimethylaminotrimethylene) bis (thiocarbamate), N, N-dimethyl 1,2 , 3-tritian-5-yl-amine, 2-3-butylamino-3-isopropyl-5-phenyl-1,3,5-thiaziazin-4-one, 2- (4-ethoxy Phenyl) -2-methylpropyl 3-phenoxybenzyl ether and (RS) -α-cyano-3-phenoxybenzyl (R, S) -2,2-dichloro-1- (4-ethoxyphenyl)- It has been found that novel active substance combinations of at least one known pesticidal active compound selected from the group consisting of cyclopropane carboxylates exhibit particularly good fungicidal and pesticidal activity.

Where

Z represents a halogen atom,

R ¹ represents a C _1-4 alkyl group,

R ² represents a hydrogen atom, a methyl group or an ethyl group,

R ³ represents a hydrogen atom or a methyl group.

The pesticidal and fungicidal active substance combinations of the present invention are surprisingly used to control pest and crop diseases using fungicidally active carboxamides represented by the general formula (I) or optical isomers thereof and known pesticidal active compounds, respectively. In addition to controlling pests and crop diseases at the same time as opposed to controlling them, the cooperative and synergistic effects of a mixture of two active ingredients, which was not expected from the technical effects created by the simple use of two active compounds separately Due to the use of very low doses it may exhibit excellent insecticidal and fungicidal effects.

In addition, the insecticidal and fungicidal active substance combinations according to the present invention can be used in the plant species of hemiptera and cicada larvae, rice cultivars belonging to the tree choloptera (Lissorhoptrus oryzophilus), and lepidoptera. Major pests resulting from rice cultivation, such as the Blackfly moth (Cnaphalocrocis medinalis) belonging to the order of the Lepidoptera, are resistant to known pesticides such as organic compounds and carbamates, even though they are resistant to them. It is possible to show stable and excellent action and effect at the same time not only for the disease but also for the disease known as the most harmful disease.

One substance in the active substance combination according to the invention is generally defined by the general formula (I) above.

Preferably, in general formula (I)

Z represents a chlorine atom,

R ¹ represents methyl, ethyl, n-propyl or isopropyl,

R ² represents a hydrogen atom or methyl,

R ³ represents a hydrogen atom or methyl.

As specific examples of the compound of general formula (I), the following compounds may be mentioned:

N- [1- (4-bromophenyl) -ethyl] -2,2-dichloro-1,3,3-trimethylcyclopropane carboxamide,

N- [1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1,3,3-trimethylcyclopropane carboxamide,

N- [1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-ethyl-3-methylcyclopropane carboxamide,

N- [1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-isopropylcyclopropane carboxamide,

Diastereomeric mixtures of N- (R)-[1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropane carboxamide,

Diastereomeric mixtures of N- (R)-[1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-isopropylcyclopropane carboxamide,

N- (R)-[1- (4-Chlorophenyl) -ethyl]-(1S) -2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropane carboxamide, and

N- (R)-[1- (4-Chlorophenyl) -ethyl]-(1S) -2,2-dichloro-1-isopropylcyclopropane carboxamide.

The above-mentioned compounds are already known from the above references, i.e., Japanese Patent Publication Nos. 1587/1986, 201855/1987 and 11550/1990.

Known pesticidal active compounds used in the pesticidal and fungicidal active substance combinations of the invention are those disclosed in Pesticide Manual 8th ed., 1987, published by the British Crop Protection Council and Noyaku Binran (Pesticide Handbook), 1988.

According to the present invention, the weight ratio between the active ingredients included in each mixed composition can vary within a relatively wide range. In general, 0.5 to 10 parts by weight, preferably 1 to 8 parts by weight of known insecticidal active compounds can be used per 1 part by weight of the fungicidally active carboxamide represented by the general formula (I) or the optical isomer thereof.

However, the above-mentioned weight ratios can be varied according to the extent of damage caused by pests and fungi, if necessary.

The insecticidal and fungicidal active substance combinations of the present invention exhibit excellent insecticidal and fungicidal activity, and are therefore advantageously used as insecticides and fungicides in applications such as foliar application, underwater or immersion application, soil treatment, soil incorporation application, bedplate treatment and the like. Used.

The insecticidal and fungicidal active substance combinations of the present invention exhibit potent insecticidal and fungicidal effects and can therefore be preferably used as mixed insecticides and fungicides. In addition, the active substance combinations of the present invention have very low phytotoxicity to the plants under cultivation and toxicity to warm-blooded animals, so that the combinations can be used to ensure the protection of crops, especially rice, in various fungi, pests, in particular insect pests and plants. It can be used safely and effectively to control disease. This active composition is usually very active throughout its growth phase or during certain periods of time for normal, susceptible and chemically resistant species of pests and diseases.

As plant diseases and insect pests, the following may be mentioned and specifically exemplified:

Plant disease fungi include Plasmodiophoromycetes, Oomycetes, Chitridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Basidiomycetes. Incomplete fungi (Deuteromycetes) is an example.

In particular, Pyricularia oryzae belonging to incomplete fungi may belong to the fungicidal spectrum of the pesticidal and fungicidally active substance combinations of the present invention.

Pests to be controlled of the present invention include lysoloft lupus orizophilus, Echinocinemus squameus, Oulema oryzae belonging to the tree of Koleopterra; Chilo suppressalis, Knapaloscrossis Medialis, Naranga aenescens, Parnara guttata, belonging to the tree of Repiddorfera; Nehotextics cincticeps, Nilaparvata lugens, Laodelphax striatellus, Sogatella furcifera Nezara spp; And Gryllotalpa africana, Locusta migratoria migratoriodes, belonging to Ortoperra mok.

The pesticidal and fungicidal active substance combinations of the invention may be formulated in conventional formulations.

Such preparations include, but are not limited to, ULV cold and warm agents, as well as solutions, emulsions, suspensions, powders, wetting agents, foams, pastes, granules, aerosols, natural and synthetic materials, microcapsules, seeds impregnated with the active compound. Mention may be made of coating compositions and formulations used with combustion devices such as fumigation cartridges, fumigation cans and fumigation coils.

These formulations are prepared by known methods, for example by optionally using surfactants, ie emulsifiers, dispersants and / or foam formers, by mixing the active compounds with extenders, ie liquid or liquefied gases or solid diluents or carriers. Can be. When water is used as the extender, organic solvents can also be used, for example, as auxiliary solvents.

Liquid diluents or carriers are mainly water, as well as aromatic hydrocarbons such as xylene, toluene alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene and methylene chloride, cyclohexane or paraffin (e.g. mineral oil) Aliphatic or cycloaliphatic hydrocarbons, alcohols such as butanol or glycols, as well as ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or dimethylformamide and Strong polar solvents such as dimethyl sulfoxide are suitable.

By liquefied gas diluent or carrier is meant an aerosol propellant, such as liquids such as butane, propane, nitrogen and carbon dioxide, as well as halogenated hydrocarbons, at normal temperatures and under normal input.

As solid diluents, ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly dispersed silicic acid, alumina and silicates can be used.

Solid carriers for granulation include synthetic granules of inorganic and organic powders as well as crushed and classified natural minerals such as calcite, marble, pumice, calcite and dolomite, and granules of organic materials such as sawdust, coconut husks, corn cobs and tobacco stems. This can be used.

Emulsifiers and / or foam-forming agents include nonionic and anionic emulsifiers, for example polyoxyethylene fatty alcohol ethers such as polyoxyethylene fatty acid esters, alkylarylpolyglycol ethers, alkylsulfonatelus, alkylsulfates As well as arylsulfonates, albumin hydrolysis products can be used. As a dispersing agent, lignin sulfite waste liquid and methyl cellulose are contained, for example.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers (eg, gum arabic, polyvinyl alcohol and polyvinylacetate) can be used in formulations in the form of powders, granules or emulsifiable concentrates.

Trace amounts such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and coloring agents such as alizarin dyes, azo dyes and organic dyes such as metal phthalocyanine dyes and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc You can use elements.

The formulations contain, for example, 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.

The insecticidal and fungicidal active substance combinations of the invention are optionally themselves or in combination with other active agents such as insecticides, bactericides, mildewcies, fungicides, growth regulators or herbicides. It can be used as a preparation or in the form of use prepared therefrom. Examples of insecticides include those derived from organic phosphates, carbamates, carboxylates, hydrocarbon chlorides and pesticidal substances derived from microorganisms.

In addition, the pesticidal and fungicidal active substance combinations of the present invention may be a combination with a synergist in a commercially useful type of formulation or form of use. The term synergist refers to a compound which is in itself inactive but which promotes the action of the active compound. The content of the pesticidal and fungicidal compositions of the present invention in formulations of commercially available type can vary within a significant range, ie, from about 0.00001 to 100% by weight, preferably from about 0.001 to 5% by weight.

The pesticidal and fungicidal active substance combinations of the present invention may be used in a conventional manner suitable for a particular formulation.

The pesticidal and fungicidal active substance combinations of the present invention are a mixture of the active compound represented by the above-mentioned general formula (I) and known pesticidal active compound pairs in the reaction system, and may be prepared in the form of a so-called tank mix formulation. have.

The present invention will be described in more detail later with reference to examples, but they should not be construed as limiting the scope of the invention in any respect.

Biological Example

[Test Compound]

I.1: N- [1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1,3,3-trimethylcyclopropane carboxamide,

1.2: N- [1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-ethyl-3-methylcyclopropane carboxamide,

I.3: N- [1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-isopropylcyclopropane carboxamide,

I.4: diastereomeric mixtures of N- (R)-[1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropane carboxamide,

I.5: N- (R)-[1- (4-Chlorophenyl) -ethyl]-(1S) -2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropane carboxamide,

I.6: N- [1- (4-bromophenyl) -ethyl] -2,2-dichloro-1,3,3-trimethylcyclopropane carboxamide,

I.7: Diastereomeric mixtures of N- (R)-[1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-isopropylcyclopropane carboxamide.

A: S, S '-(2-dimethylaminotrimethylene) bis (thiocarbamate),

B: N, N-dimethyl-1,2,3-tritian-5-yl-amine,

C: 2-3-butylimino-3-isopropyl-5-phenyl-1,3,5-thiaziazin-4-one,

D: 2- (4-ethoxyphenyl) -2-methylpropyl 3-phenoxybenzyl ether, and

E: (RS) -α-cyano-3-phenoxybenzyl (RS) -2,2-dichloro-1- (4-ethoxyphenyl) -cyclopropane carboxylate.

Example 1

Preparation of Active Compounds

Each active compound: 5-25 parts by weight

Carrier: 70 to 90 parts by weight of diatomaceous earth / kaolin mixture (1: 5 mixture)

Emulsifier: 5 parts by weight of polyoxyethylene alkylphenyl ether

To prepare a suitable formulation of each active compound, the specified amount of each active compound, the specified amount of carrier, and the specified amount of emulsifier are grinded and mixed to form a wetting agent for each active compound, followed by The desired formulation is formed by mixing the hydrating agents and diluting to the desired concentration with water.

[Test Methods]

Three bags of rice (Asahi varieties) are cultivated in white porcelain pots with a diameter of 12 cm. In the initial tilling stage of rice, each of the predetermined concentrations of the active compound solution is irrigated through the water in the pot using a pipette until the indicated dosage is reached while the ground portion of the rice is not exposed to the solution.

After 3 days, each pot is covered with a net basket, and at the same time 10 4 larvae of green rice leafhopper are inoculated and 2 days after the inoculation, the mortality of the insects is measured.

Twenty days after treatment, Pyricularia oryzae suspension is inoculated by spraying each port according to conventional methods and placed in the inoculation chamber for 24 hours at a temperature in the range of 25-26 ° C. and 100% relative humidity. Thereafter, each pot was transferred to a glass greenhouse maintained at a temperature in the range of 20 to 28 ° C. and 7 days after inoculation, the infection rate of rice per pot was measured and recorded according to the following evaluation grade, control rate (%) and phytotoxicity. Evaluate the degree as well.

The control value percentage is calculated using the following formula.

Where

A represents the extent of infection in the control (untreated) area:

B represents the extent of infection in the treated area.

In this test, each test area consists of three ports.

The results of this test are shown in Table 1.

Example 2

(i) Leaf application test for brown perilla and leafy moth

Preparation of Active Compounds

Each active compound: 30 to 40 parts by weight

Carrier: 55 to 65 parts by weight of diatomaceous earth / kaolin mixture (1: 5 mixture)

Emulsifier: 5 parts by weight of polyoxyethylene alkylphenyl ether

To prepare a suitable formulation of each active compound, a specified amount of each active compound, a specified amount of carrier, and a specified amount of emulsifier are mixed under grinding to form a wetting agent for each active compound, followed by The desired formulation is formed by mixing the hydrating agents and diluting to the desired concentration with water.

Test Methods

Three acres of rice, each about 15 cm tall, were planted in a pot 13 cm in diameter, and after 10 days of rooting, an aqueous solution of each of the active compound preparations having the predetermined concentrations mentioned above was sprayed with a sprayer 20 ml per pot. After spraying the pot with a dosage of, the sprayed formulations were dried, and each pot was covered with a net basket, while at the same time inoculating the 3rd larva of brown perilla and the 4th larva of leafy moth at a rate of 10 each per port. Later, after 5 days for brown extinction and after 3 days for leafy moths, the number of dead insects is measured to obtain mortality for each type of insect.

(ii) foliar application test for blast disease

Test Methods

Rice (Asahi varieties) are grown in magnetic pots with a diameter of 12 cm. 50 ml of the above-prepared formulation of each active compound in 3 pots in 3-4 leaf stages.

Spray to rice in the amount of. The next day, a spore suspension of the pyrophilic fungus Pyricularia oryzae (artificially cultured) is sprayed twice over rice and placed in a greenhouse at a temperature of 25 ° C. and 100% relative humidity for infection.

Seven days after the inoculation, the infection rate of the blast disease is measured and recorded according to the following evaluation grade; At the same time the percent control and phytotoxicity are also evaluated.

Controlled percentages are calculated using the following formula:

Where

A represents the extent of infection in the control (untreated) region;

B represents the extent of infection in the treated area.

In this test, each test compartment consists of three ports.

The results of the tests mentioned in (i) and (ii) are shown in Table 2.

Claims (5)

(1) a carboxamide represented by the following general formula (I) or an optical isomer thereof, and (2) S, S '-(2-dimethylaminotrimethylene) bis (thiocarbamate), N, N-dimethyl 1, 2,3-tritian-5-yl-amine, 2-3-butylamino-3-isopropyl-5-phenyl-1,3,5-thiaziazin-4-one, 2- (4-e Methoxyphenyl) -2-methylpropyl 3-phenoxybenzyl ether and (RS) -α-cyano-3-phenoxybenzyl (R, S) -2,2-dichloro-1- (4-ethoxyphenyl) A fungicide and pesticidal composition characterized in that it contains an active substance combination consisting of at least one pesticidal active compound selected from the group consisting of cyclopropane carboxylates. In the formula, Z represents a halogen atom, R ¹ represents a C _1-4 alkyl group, R ² represents a hydrogen atom, a methyl group or an ethyl group, and R ³ represents a hydrogen atom or a methyl group. The fungicidal and pesticidal composition according to claim 1, wherein the weight ratio of (1) and (2) in the active substance blend is 1: 0.05 to 1:10. A method for controlling fungi and pests, characterized in that the active substance combinations according to claims 1 or 2 act on fungi and pests or their habitat. A process for preparing fungicidal and pesticidal compositions according to claim 1 or 2, characterized in that the other active substance combination is mixed with at least one component selected from the group consisting of a weighting agent and a surfactant. The fungicidal and pesticidal composition according to claim 2, wherein the weight ratio of (1) and (2) in the active substance combination is from 1: 0.1 to 1: 5.