JPH072607B2 - Agricultural insecticidal bactericidal composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention comprises a novel agricultural insecticidal and bactericidal composition containing an imino-substituted heterocyclic compound of the formula (I) described below and a known bactericidal active compound as active ingredients and exhibiting an excellent insecticidal and bactericidal action. Regarding things.

The imino-substituted heterocyclic compounds of formula (I) used in the present invention and their use as insecticides are described in Japanese Patent Application No. 60-106854.
Japanese Patent Application No. 60-219082 and Japanese Patent Application No. 61-48629.

It has already been described in JP-B-44-12919 that O-ethyl S, S diphenyl phosphorodithioate (ediphenphos edifenphos) has a control activity against rice blast disease. Furthermore, it has already been described in JP-B-44-32592 that 4,5,6,7-tetrachlorophthalide (fthalide fthalide) has a rice blast control activity.

However, the action of these active compounds alone has either an insecticidal effect or a bactericidal effect, and it is not possible to simultaneously control the disease caused by the disease fungus and the damage caused by the pest.

According to the present inventors, (1) general formula In the formula, X represents S, CH ₂ or NR ² (in the formula, R ² represents a hydrogen atom or an alkylcarbonyl group), and R ¹ is an optionally substituted pyridyl group (the substituent is a halogen atom). And at least one selected from an alkyl group represents a thiazolyl group (wherein the substituent represents at least one selected from a halogen atom and an alkyl group), even if it is substituted, and m is 2 or 3 , And Z represents NO ₂ or CN, and a novel active mixture containing (2) O-ethyl S, S diphenyl phosphorodithioate as an active ingredient is excellent in insecticidal sterilization. It was found to show activity.

Conventionally, various chemicals have been developed as insecticides for concentrated horticulture, and have been used as single agents and mixed agents. In particular, organophosphorus insecticides and carbamate insecticides are mainly used, and then pyrethroid insecticides have been used. However, conventional insecticides have certain insecticidal effects, but they have insecticidal spectrum, insecticidal effect (in various growth stages such as eggs, larvae, and adult worms), residual larvae, and fast-acting effect. However, it is not fully satisfied with various characteristics such as toxicity, osmotic transferability, low toxicity to fish and warm-blooded animals, reduction of environmental pollution, reduction of application frequency and application amount.

Furthermore, as a result of repeated use of conventional chemicals, various pests that have acquired resistance to various pests have appeared.
In particular, planthoppers and leafhoppers (eg, leafhopper leafhoppers), which are hemiptera pests that have acquired resistance to organophosphorus insecticides and carbamate insecticides, have recently appeared in rice fields in various regions including Japan's southwestern warm regions. However, it is becoming difficult to control them, and development of an excellent drug is desired.
Furthermore, pests such as diamondback moth, which is a vegetable pest that infests aphids, mites, and cruciform vegetables, have acquired drug resistance, and control of such resistant pests or susceptible pests and resistant British pests have been acquired. There is a demand for the development of an excellent drug capable of simultaneously controlling the above.

Further, in recent years, paddy rice cultivation in Japan is mainly carried out by mechanical transplantation by a seedling transplanter, and together with pest control in paddy rice Honda, an excellent and non-harmful drug for controlling pests by applying a nursery box. Development is desired. Furthermore,
Development of an excellent drug against pests which have been particularly problematic in recent years, for example, rice weevil and the like has been desired.

Therefore, important pests of food crops including rice and other shells and pests of garden crops such as vegetables, flowers and fruit trees, tobacco,
Pests of industrial crops such as cotton and tea, forest pests, and pests of some of these institutional horticultural crops, soil pests such as cotton,
It is desired to develop a drug having an even more excellent effect on sucking and feeding abilities of stored grain pests and various other pests.

Furthermore, along with the development of the above-mentioned excellent insecticides, it is desired to develop an insecticidal fungicide capable of simultaneously controlling the main diseases and pests such as rice blast and planthoppers and leafhoppers in the cultivation of rice.

As a result of earnest studies to solve the above-mentioned various problems, the present inventors have surprisingly found that (1) the imino-substituted heterocyclic compound of the formula (1) and (2) the known O-ethyl S, S-
The active mixture according to the present invention comprising diphenyl phosphorodithioate exhibits excellent cooperation and synergism, which is unexpected from the effect of each active compound alone, and exhibits excellent insecticidal and bactericidal effects against diseases and pests of rice. I found to show.

Therefore, the insecticidal and bactericidal composition of the present invention is very effective in agricultural crop cultivation, for example, especially for simultaneous control of pests and labor saving, and is a technically excellent technical step in industrial utility. Is provided.

The imino-substituted heterocyclic compounds of general formula (I) used in the active substance combinations according to the invention are defined below.

In the formula, X represents S, CH ₂ or NR ² (in the formula, R ² represents a hydrogen atom or an alkylcarbonyl group), and R ¹ is an optionally substituted pyridyl group (the substituent is a halogen atom). And at least one selected from an alkyl group) or an optionally substituted thiazolyl group (wherein the substituent represents at least one selected from a halogen atom and an alkyl group), and m is 2 or 3 And Z represents NO ₂ or CN.

In the general formula (I), preferably X represents S, CH ₂ or NR ² (in the formula, R ² represents a hydrogen atom or an alkylcarbonyl group having 1 to 3 carbon atoms of the alkyl group), R ¹ represents a pyridyl group substituted with one or two selected from a chloro atom, a bromine atom, a fluor atom and a methyl group, or a chloro atom, a fluor atom, a bromine atom or a thiazolyl group substituted with a methyl group, and The bonding position of the pyridine ring is 3-position (or 5-position), the bonding position of the thiazole ring is 5-position, and m is 2
Or 3 and Z represents NO ₂ or CN.

Examples of imino-substituted heterocyclic compounds of the general formula (I) used in the active substance combination according to the invention are the following compounds:

1- (3-pyridylmethyl) -2- (nitroimino) imidazolidine, 1- (2-chloro-5-pyridylmethyl) -2- (nitroimino) imidazolidine, 1- (2-chloro-5-pyridylmethyl) -2- (Nitroimino) theorahydropyrimidine 1- (2-Fluoro-5-pyridylmethyl) -2- (nitroimino) imidazolidine, 1- (2-Fluoro-5-pyridylmethyl) -2- (nitroimino) tetrahydropyrimidine , 1- (2-bromo-5-pyridylmethyl) -2- (nitroimino) imidazolidine, 1- (2,3-dichloro-5-pyridylmethyl) -2-
(Nitroimino) imidazoline, 1- (2-methyl-5-pyridylmethyl) -2- (nitroimino) imidazolidine, 1- (2-methyl-5-pyridylmethyl) -2- (nitroimino) tetrahydropyrimidine, 1- ( 2-chloro-5-thiazolylmethyl) -2- (nitroimino) imidazolidine, 1- (2-chloro-5-thiazolylmethyl) -2- (nitroimino) tetrahydropyrimidine, 1- (2-fluoro-5-thiazolylmethyl) -2 −
(Nitroimino) imidazolidine, 1- (2-methyl-5-thiazolylmethyl) -2- (nitroimino) imidazolidine, 1- (2-methyl-5-thiazolylmethyl) -2- (nitroimino) tetrahydropyrimidine, 1-acetyl- 3- (2-chloro-5-pyridylmethyl) -2- (nitroimino) imidazolidine, 1-acetyl-3- (2-chloro-5-pyridylmethyl) -2- (nitroimino) tetrahydropyrimidine, 1-butyryl- 3- (2-chloro-4-fluoro-5-
Pyridylmethyl) -2- (nitroimino) imidazolidine, 3- (2-chloro-5-pyridylmethyl) -2- (nitroimino) thiazolidine, 3- (2-chloro-5-pyridylmethyl) -2- (nitroimino) Tetrahydro-2H-1,3-thiazine, 3- (2-fluoro-5-pyridylmethyl) -2- (nitroimino) thiazolidine, 1- (2-chloro-5-pyridylmethyl) -2- (nitroimino) pyrrolidine, 1- (2-chloro-5-pyridylmethyl) -2- (nitroimino) piperidine, 1- (2-bromo-5-pyridylmethyl) -2- (nitroimino) pyrrolidine, 1- (2-fluoro-5-pyridyl Methyl) -2- (nitroimino) pyrrolidine, 1- (2-chloro-5-pyridylmethyl) -2- (cyanoimino) imidazoline, -(2-chloro-5-pyridylmethyl) -2- (cyanoimino) tetrahydropyrimidine, 1- (2-fluoro-5-pyridylmethyl) -2- (cyanoimino) imidazolidine, 1- (2-bromo-5- Pyridylmethyl) -2- (cyanoimino) imidazolidine, 1- (2-methyl-5-pyridylmethyl) -2- (cyanoimino) imidazolidine, 1- (2-methyl-5-pyridylmethyl) -2- (cyanoimino ) Tetrahydropyrimidine, 1- (2-chloro-5-thiazolylmethyl) -2- (cyanoimino) imidazolidine, 1- (2-chloro-5-thiazolylmethyl) -2- (cyanoimino) tetrahydropyrimidine, 1- (2-fluoro -5-thiazolylmethyl) -2-
(Cyanoimino) tetrahydropyrimidine, 1- (2-chloro-5-pyridylmethyl) -2- (cyanoimino) thiazolidine, 1- (2-chloro-5-pyridylmethyl) -2- (cyanoimino) tetrahydro-2H-1, 3-thiazine, 1- (2-fluoro-5-pyridylmethyl) -2- (cyanoimino) thiazolidine, 1- (2-chloro-5-thiazolylmethyl) -2- (cyanoimino) thiazolidine, 1- (2-chloro- 5-thiazolylmethyl) -2- (cyanoimino) tetrahydro-2H-1,3-thiazine.

One bactericidal active substance, O-ethyl S, S-diphenyl, used in the active substance combination according to the invention.
Phosphorodithioate is represented by the following formula.

The 4,5,6,7-tetrachlorophthalide of (3) which can be further contained in the active substance combination of (1) and (2) according to the present invention is represented by the following formula.

In the present invention, the weight ratio of the active compounds of each group in the active substance combination can be varied within a relatively wide range, generally (1) the activity of the imino-substituted heterocyclic compound of general formula (I) Per part by weight of active compound of the compound group,
O-ethyl S, S-diphenyl phosphorodithioate of (2), for example, 0.05 to 20 parts by weight, preferably 0.1 to 10 parts by weight, and 4,5,6,7-tetrachlorophthalide of (3) are added. In this case, the component (3) can be used, for example, in an amount of 0.05 to 20 parts by weight, preferably 0.1 to 10 parts by weight.

The active substance combination according to the present invention exhibits excellent insecticidal and bactericidal activity, and can be used as an insecticidal fungicide, for example, by foliage application, water or water application, soil application, soil admixture treatment, nursery box application and the like.

The active substance combinations according to the invention exhibit a strong insecticidal fungicidal action. Therefore, it can be used as an insecticidal fungicide. And, the active compound according to the present invention has no phytotoxicity to cultivated plants, and also has low toxicity to warm-blooded animals, for controlling pests, particularly insects and pests in agriculture, particularly in protecting rice, in order to accurately control them. Can be used for They are,
It is usually active against sensitive and resistant species, and all or some stages of development.

Examples of the above-mentioned pests (disease and pest) include the following. Examples of such pests include the following pests.

As insects, pests of the order Coleoptera, for example, weevils (Lissorhoptrus oryzophilus), weevils (Echin
ocinemus squameus), rice leafhopper (Oulema oryz)
ae); Lepidoptera, for example, Chilo suppressalis, Cnaphalocrocis medinalis, Nara
nga aenescens), Ichimon Dyseri (Parnara guttat)
a); Hemiptera, such as leafhoppers (Nephotettix cincticeps), brown planthoppers (Nilaparvata lugens), and brown planthoppers (La)
odelphax striatellus), White-faced planthopper (Sogatella fu)
rcifera), green stink bug (Nezara spp.); Orthoptera, for example, kerula (Gryl-lotalpa africana), grasshopper (Locusta mig)
Examples of diseases include archaebacteria [Archimycetes], algae [Phycomycetes], ascomycetes [Ascomycetes], basidiomycetes [Basidiomycetes], Fungi [Eungi Imperfecti], various plant diseases caused by other bacteria; and the like.

Typical examples of the bactericidal spectrum of the above plant diseases include, for example, rice blast fungus (Pyricularia oryzae) and sesame leaf blight fungus (Cohliobolus mi
yabeanus), etc., but the sterilization spectrum should not be limited to these.

The active substance combinations according to the invention can be in the form of mixtures with the components (1) and (2) and optionally component (3) or in the form of individual formulations, each for mixing in situ. And as such a form, a liquid preparation, an emulsion, a suspension, a powder, a foam, a paste, a granule, an aerosol, an active compound infiltrating-natural and synthetic product, a microcapsule, a seed coating, and a preparation provided with a combustion device. (For example, fumigation and fumigation cartridges, cans and coils for combustion equipment), and ULV [cold mist (cold mis
t), warm mist].

These preparations can be manufactured by a known method. Such processes include, for example, spreading the active compound as a spreading agent, ie liquid diluent; liquefied gas diluent; solid diluent, or carrier, optionally surfactant, ie emulsifier and / or dispersant and / or It can be carried out by mixing with a foam forming agent. When using water as a spreading agent,
For example, organic solvents can also be used as cosolvents.

Examples of the liquid diluent or carrier include aromatic hydrocarbons (eg, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg, chlorobenzenes, methylene chlorides, chlorides). Methylene etc.), aliphatic hydrocarbons [eg cyclohexane etc., paraffins (eg mineral oil fraction etc.)], alcohols (eg butanol, glycol and their ethers, esters etc.), ketones (eg acetone,
Mention may also be made of methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strongly polar solvents (eg dimethylformamide, dimethylsulfoxide etc.) and water.

The liquefied gas diluent or carrier is a gas at room temperature and atmospheric pressure, examples of which include aerosol propellants such as butane, propane, nitrogen gas, carbon dioxide, and halogenated hydrocarbons.

As the solid diluent, soil natural minerals (for example, kaolin, clay, talc, chiyoke, quartz, attapal guide, montmorillonide, diatomaceous earth, etc.), soil synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.) Can be mentioned.

Solid carriers for granules include ground and fractionated rocks (eg, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic particles of inorganic and organic powders, and fine particles of organic material (eg, , Sawdust, coconut coconut, corn cob and tobacco stem).

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, alkyl sulphates] , Aryl sulfonates, etc.)], and albumin hydrolysis products.

Dispersants include, for example, lignin sulfite waste liquor and methylcellulose.

Sticking agents can also be used in the formulations (powder, granules, emulsions). Such sticking agents may include carboxymethyl cellulose and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate.

It is also possible to use colorants, which include 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, copper, cobalt, molybdenum, zinc and their salts.

The formulation can contain, for example, 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of the active ingredient.

The active substance combinations according to the invention are in their commercially useful formulations and the use forms prepared according to these formulations,
Other active compounds, such as insecticides, fungicides, fungicides,
It can be present as a growth regulator or as a mixture with herbicides. Here, examples of the insecticide include organic phosphorus agents, carbamate agents, chlorohydrocarbon agents, carbonoxylate agents, and insecticidal substances produced by microorganisms.

Furthermore, the active compound mixtures according to the invention can also be present as admixtures with synergists, such preparations and forms of use being those which are commercially useful. The synergist is a compound which amplifies the action of the active compound, which need not be active in and of itself.

The content of the active substance combinations according to the invention in the commercially useful use forms can be varied within wide limits.

The working concentration of the active compound mixtures according to the invention is, for example, 0.
The amount is 00001 to 100% by weight, preferably 0.001 to 5% by weight.

The active compound mixtures according to the invention can be used in the usual manner depending on the use form.

Next, the contents of the present invention will be specifically described with reference to Examples.
The present invention should not be limited to this.

Example 1 (i) Test against brown planthopper Preparation of test compound Each active compound: 25 to 50 parts by weight Carrier: Mixture of diatomaceous earth and kaolin (1: 5) 45 to 70 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 a predetermined amount of the wettable powder is diluted with water and mixed.

Test method: Planting 3 rice plants with a plant height of about 15 cm in a pot with a diameter of about 13 cm
After 10 days, spray 20 ml of a diluted solution of the active compound prepared in advance with a spray gun on each pot, air-dry the sprayed drug solution, cover the pot with a net cage, and inoculate 4 larvae of the brown planthopper, 10 larvae per pot. Three days after the inoculation, dead insects were counted and the insecticidal rate was calculated.

(Ii) Foliar spraying efficacy test for rice blast test method Paddy rice (quality: 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 the 3 to 4 leaf stage was added per 3 pots. 50 ml was sprayed. The next day, a suspension of rice blast spores artificially cultured on the next day was spray-inoculated (twice) and kept in a humid chamber at 25 ° C and 100% relative humidity for infection. Seven days after the inoculation, the degree of morbidity per pot was classified and evaluated according to the following criteria, and the control value (%) was determined. The drug damage was also investigated at the same time.

Degree of morbidity Lesion area ratio (%) 0 0 less than 0.5 2 12 less than 5 2 5 less than 10 3 10 less than 20 4 20 less than 40 5 40 or more This test is a result of 3 pots in 1 ward.

The results of the tests (i) and (ii) are summarized and shown in Tables 1 and 2.

Note 1: No phytotoxicity is observed in all the mixtures and single agents used in Examples 1 (i) and (ii).

2. Compound of the general formula (I) used in the present invention: Compound NO.1 1- (2-chloro-5-pyridylmethyl)
-2- (Nitroimino) imidazoline, Compound NO.2 1- (2-chloro-5-pyridylmethyl)
-2- (nitroimino) tetrahydropyrimidine, compound NO.3 1- (2-chloro-5-thiazolylmethyl) -2- (nitroimino) imidazolidine, compound NO.4 1-acetyl-3- (2-chloro-5- Pyridylmethyl) -2- (nitroimino) imidazolidine, compound NO.5 3- (2-chloro-pyridylmethyl) -2
-(Nitroimino) thiazolidine, Compound NO.6 1- (2-chloro-5-pyridylmethyl)
-2- (nitroimino) piperidine, compound NO.7 1- (2-chloro-5-pyridylmethyl)
-2- (cyanoimino) imidazolidine.

3. Compound used in the present invention: Compound (A): Edifenphos Compound (B): Fusalide Example 2 The mixture composition of the present invention in Example 1 was used in a test group in which brown planthopper and rice blast occurred at the same time. As a result, the pests were completely simultaneously controlled with a control value of 100%.

Example 3 (Wettable powder) 25 parts of the active compound of formula (I), 25 parts of edifenphos, 45 parts of a mixture of powdered diatomaceous earth and powdered clay (1: 5), 2 parts of sodium alkylbenzenesulfonate, alkylnaphthalenesulfone. 3 parts of sodium acid formalin condensate is ground and mixed to obtain a wettable powder.

Example 4 (Dust) A powder is prepared by pulverizing and mixing 1 part of the active compound of formula (I), 2 parts of edifenphos and 97 parts of powdered clay.

Continuation of front page (51) Int.Cl. ⁶ Identification code Office reference number FI technical display area A01N 43:54 43:78 43:86)

Claims (2)

[Claims] (1) General formula In the formula, X represents S, CH ₂ or NR ² (in the formula, R ² represents a hydrogen atom or an alkylcarbonyl group), and R ¹ is an optionally substituted pyridyl group (the substituent is a halogen atom). And at least one selected from an alkyl group) or an optionally substituted thiazolyl group (wherein the substituent represents at least one selected from a halogen atom and an alkyl group), and m is 2 or 3 And Z is NO ₂ or CN, and an active compound mixture comprising an imino-substituted heterocyclic compound of (2) and (2) O-ethyl S, S diphenyl phosphorodithioate. Insecticidal germicidal composition. 2. A mixture of the active compounds of (1) and (2)
5. The agricultural insecticidal and bactericidal composition according to claim 1, further comprising 5,6,7-tetrachlorophthalide.