JPH0558401B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a novel agricultural insecticidal and fungicidal composition that contains a nitromethylene derivative of formula (2) and a known fungicidally active compound as active ingredients and exhibits excellent insecticidal and fungicidal activity. Most of the nitromethylene derivatives of the formula () used in the present invention are compounds that have not been previously described in known literature,
The compounds and their use as insecticides are disclosed in the prior invention patent application filed in 1983 filed by the same applicant.
No. 72966 and Japanese Patent Application No. 59-132943. Compounds with l=0 in the nitromethylene derivatives of the formula () and their use as insecticides are known, and are disclosed in Japanese Patent Application Laid-Open No. 172976/1989 filed by the same applicant. . Furthermore, it has already been described in Japanese Patent Publication No. 12919/1983 that O-ethyl S,S-diphenyl phosphorodithioate has an activity for controlling rice blast disease. However, the action of these active compounds is
Each alone has only an insecticidal effect or a bactericidal effect, and cannot control diseases caused by pathogenic bacteria and damage caused by insect pests at the same time. By the present inventors, (1) General formula In the formula, X represents a lower alkyl group, a lower alkoxy group, or a halogen atom, l0.1 or 2, and m represents 2 or 3, and (2) O-ethyl S,S It has been found that a new active mixture containing -diphenylphosphorodithioate as an active ingredient exhibits excellent insecticidal and fungicidal activity. Conventionally, various pesticides have been developed as agricultural and horticultural insecticides, and have been used as single agents or mixtures. In particular, organophosphorus insecticides and carbamate insecticides are mainly used, and subsequently pyrethroid insecticides have been used. However, although conventional insecticides each have a certain type of insecticidal effect, they differ in their insecticidal spectrum, insecticidal effect (insecticidal effect on various growth stages, such as eggs, larvae, and adult insects), persistence, and quick-acting effect. sex, systemic migration, and fish;
They do not fully satisfy various characteristics such as low toxicity to warm-blooded animals, reduced environmental pollution, and reduced number of applications and dosage. Furthermore, as a result of repeated use of conventional chemicals, various pests have emerged that have acquired resistance to them. In particular, in recent years, planthoppers and leafhoppers (e.g., leafhoppers), which are hemiptera pests, have developed resistance to organophosphorus and carbamate insecticides in rice paddies across Japan, including the warm southwest region. , it is becoming difficult to control them, and the development of superior drugs is desired.
Furthermore, pests such as aphids, mites, vegetable pests such as the diamondback moth and cotton poleworm, which are vegetable pests that attack cruciferous vegetables, have acquired drug resistance, and it is necessary to control such resistant pests or to separate susceptible and resistant pests. It is desired to develop an excellent drug that can simultaneously control the disease. In addition, in recent years, paddy rice cultivation in Japan has mainly been carried out by mechanical transplantation using seedling transplanters, and in addition to pest control in paddy rice cultivation, seedling box application is an excellent and non-toxic method for pest control. Development of a drug is desired. Furthermore, there is a desire to develop an excellent drug against pests that have become a particular problem in recent years, such as the rice weevil. Therefore, important pests of food crops including rice and other grains, pests of horticultural crops such as vegetables, flowers, and fruit trees, pests of industrial crops such as tobacco, cotton, and tea, forest pests, and certain types of these Suck-sucking properties of greenhouse horticulture crop pests, soil pests such as cotton worms, stored grain pests, etc.
There is a desire for the development of drugs that have even better effects against feeding insects and other various pests. Furthermore, along with the development of excellent insecticides as mentioned above,
In particular, it is desired to develop an insecticide and fungicide that can simultaneously control rice blast, planthoppers, and leafhoppers, which are major diseases and pests in rice cultivation. As a result of intensive research to solve the various problems mentioned above, the present inventors surprisingly found that (1) nitromethylene derivatives were combined with (2) known O-ethyl S,S-diphenylphosphorodithioate. The combined active mixture according to the invention exhibits an excellent cooperative and synergistic effect that is unexpected from the effects of each active compound alone,
It was discovered that it exhibits excellent insecticidal and fungicidal effects against rice diseases and pests. Therefore, the insecticidal and fungicidal composition of the present invention is very effective in the cultivation of agricultural crops, for example, in particular, simultaneous control of pests and diseases, labor saving, etc., and has extremely outstanding technical advantages in terms of industrial usefulness. It provides an inventive step. The nitromethylene derivatives of the general formula () used in the active compound mixtures according to the invention are defined below. For use in the active compound mixtures according to the invention, A particularly preferred nitromethylene derivative of the general formula () is a compound defined as below and not described in any prior art literature. In the general formula (), X preferably represents a methyl group, a methoxy group, a chloro atom, a bromine atom or a fluoro atom, l represents 1 or 2, m represents 2 or 3, and Bonding position is 3-position (or 5-position)
It is. The nitromethylene derivative of the general formula () can also exist in the form of a salt, such as an inorganic acid salt, a sulfonate, an organic acid salt, a metal salt, etc., preferably, for example, a hydrochloride, a p- Examples include toluenesulfonate, cupric acetate, and succinate. Therefore, the nitromethylene derivative of formula () used in the present invention is a term that includes the salt form thereof. Examples of nitromethylene derivatives of the general formula () used in the active compound mixtures according to the invention include the compounds: 1-(3-pyridylmethyl)-2-(nitromethylene)tetrahydropyrimidine, 1-(2 -Methyl-5-pyridylmethyl)-2-(nitromethylene)imidazolidine, 1-(2-methyl-5-pyridylmethyl)-2-(nitromethylene)tetrahydropyrimidine, 1-(2-methoxy-5-pyridyl) methyl)-2-(nitromethylene)imidazolidine, 1-(2-methoxy-5-pyridylmethyl)
-2-(nitromethylene)tetrahydropyrimidine, 1-(2-chloro-5-pyridylmethyl)-2
-(nitromethylene)imidazolidine, 1-(2-
Chloro-5-pyridylmethyl)-2-(nitromethylene)tetrahydropyrimidine, 1-(2-fluoro-5-pyridylmethyl)-2-(nitromethylene)imidazolidine, 1-(2-fluoro-5-
pyridylmethyl)-2-(nitromethylene)tetrahydropyrimidine, 1-(2-bromo-5-pyridylmethyl)-2-(nitromethylene)imidazolidine, 1-(2-bromo-5-pyridylmethyl)-
2-(nitromethylene)tetrahydropyrimidine,
1-(5-chloro-2-pyridylmethyl)-2-
(nitromethylene)imidazolidine, 1-(5-chloro-2-pyridylmethyl)-2-(nitromethylene)tetrahydropyrimidine, 1-(2,4-dichloro-5-pyridylmethyl)-2-(nitromethylene) Tetrahydropyrimidine, 1-(2,4-
Dibromo-5-pyridylmethyl)-2-(nitromethylene)imidazolidine, 1-(2,3-dichloro-5-pyridylmethyl)-2-(nitromethylene)imidazolidine, 1-(3-pyridylmethyl)
-2-(nitromethylene)tetrahydropyrimidine-hydrochloride, 1-(2-methyl-5-pyridylmethyl)-2-(nitromethylene)tetrahydropyrimidine-p-toluenesulfonate, 1-(2-
methoxy-5-pyridylmethyl)-2-(nitromethylene)tetrahydropyrimidine-succinate,
1-(2-chloro-5-pyridylmethyl)-2-
(nitromethylene)imidazolidine hydrochloride, 1
-(2-fluoro-5-pyridylmethyl)-2-
(Nitromethylene)tetrahydropyrimidine-cupric acetate salt, 1-(2-bromo-5-pyridylmethyl)-2-(nitromethylene)imidazolidine-
Succinate, 1-(2,4-dichloro-5-pyridylmethyl)-2-(nitromethylene)tetrahydropyrimidine-p-toluenesulfonate. O-ethyl S,S-diphenyl phosphorodithioate (edifenphos), which is one component of the active compound mixture according to the invention, is already known as a rice blast control agent (Japanese Patent Publication No. 1973-1999).
Publication No. 12919). Further, the other component, 4,5,6,7-tetrachlorophthalide (fthalide), which is optionally added, is already known as a rice blast control agent (Japanese Patent Publication No. 32592/1983). In the present invention, the weight ratio of the active compounds of each group in the active compound mixture can vary within a relatively wide range; Per 1 part by weight of the compound, (2) O-ethyl S,S-diphenylphosphorodithioate, for example 0.05 to 20 parts by weight, preferably 0.1 to 10 parts by weight, and further (3) 4,5,
When adding 6,7-tetrachlorophthalide, the component (3) is, for example, 0.05 to 20 parts by weight, preferably
Can be used in amounts of 0.1 to 10 parts by weight. The active compound mixture according to the invention exhibits excellent insecticidal and fungicidal activity and can be used as an insecticidal fungicide, for example, by foliar spraying, underwater or surface application, soil application, soil mixing treatment, seedling box application, etc. The active compound mixtures according to the invention exhibit a strong insecticidal and fungicidal action. Therefore, it can be used as an insecticide and fungicide. Moreover, the active compound according to the present invention has no phytotoxicity to cultivated plants and has low toxicity to warm-blooded animals, and can be used to accurately control pests, especially insects and diseases in agriculture, particularly in the protection of rice. Can be used for They are usually active against sensitive and resistant species and against all or some growth stages. Examples of the above-mentioned pests (diseases and pests) include the following. Examples of such pests include the following. Insects include Coleoptera pests such as Lissorhoptrus oryzophilus, Echinocinemus squameus, and Oulema oryzae; Lepidoptera insects such as Chilo suppressalis, Cnaphalocrocis medinalis, and Naranga. aenescens), Parnara guttata; Hemiptera, such as Nephotettix cincticeps,
Nilaparvata lugens, Laodelphax striatelluo, Sogatella furcifera, Nazara spp.; orthoptera, such as Gryllotalpa africana, Loc-
usta migratoria migratriodes); as pests, for example, archaeal fungi [Archimycetes],
Phycomycetes, Ascomycetes, Basidiomycetes, Fungi Impefecti, and various other bacteria. Plant diseases; etc. As a representative example of the fungicidal spectrum of the above plant diseases, for example, Pyricuaria ory-
zae) and Sesame leaf blight fungus (Cohliobolus miyabeanus), which is a type of pathogen that causes rice blight, but the bactericidal spectrum is not limited to these. The active compound mixture according to the invention can be in the form of a mixture with components (1) and (2) and optionally component (3) or in the form of customary preparations, each alone for admixture in situ. Such forms include liquid,
Emulsions, suspensions, powders, foams, pastes, granules, aerosols, active compound impregnations - natural and synthetic, microcapsules, seed coatings, preparations with combustion devices (e.g. combustion devices include:
fumigation and fume cartridges, cans and coils), and ULVs (cold mist,
One example is warm mist. These formulations can be manufactured by known methods. Such a process can be carried out, for example, by combining the active compound with a vehicle, i.e. a liquid diluent; a liquefied gas diluent; a solid diluent; or a carrier, optionally a surface-active surface, i.e. an emulsifying agent and/or a dispersing agent; This can be done by mixing and/or using a foam-forming agent. When using water as a developing agent, for example, organic solvents can also be used as co-solvents. Liquid diluents or carriers include, for example, aromatic hydrocarbons (e.g. xylene, toluene, alkylnaphthalenes, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (e.g. chlorobenzenes, chlorinated ethylenes, chlorinated methylene, etc.), aliphatic hydrocarbons [e.g., cyclohexane, etc., paraffins (e.g., mineral oil fractions, etc.)], alcohols (e.g., butanol, glycol, and their ethers and esters, etc.), ketones (e.g., acetone, (such as methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strongly polar solvents (such as dimethyl formamide, dimethyl sulfoxide, etc.) and water. Liquefied gas diluents or carriers are gases at normal temperature and pressure, and include, for example, butane, propane, nitrogen gas, carbon dioxide, and aerosol propellants such as halogenated hydrocarbons. Solid diluents include soil natural minerals [e.g.
kaolin, clay, talc, chiyolk, quartz, attapal guide, montmorinite, diatomaceous earth, etc.),
Soil synthetic minerals (eg, highly dispersed silicic acid, alumina, silicates, etc.) may be mentioned. Solid carriers for granules include crushed and fractionated rocks (for example, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic granules of inorganic and organic powders,
Mention may also be made of fine particles of organic matter (for example, sawdust, coconut shells, corn cobs and tobacco stalks, etc.). Emulsifiers and/or foaming agents include nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (e.g., alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates); , arylsulfonic acid salts, etc.)] and albumin hydrolysis products. Dispersants include, for example, lignin sulfite waste liquor and methylcellulose. Fixing agents can also be used in the formulations (powders, granules, emulsions), such fixing agents include carboxymethylcellulose and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate. I can do it. Coloring agents may also be used, including inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and alizarin dyes,
Organic dyes such as azo dyes or metal phthalocyanine dyes, and also iron, manganese, boron,
Mention may be made of trace elements such as copper, cobalt, molybdenum, their salts of zinc. The formulation may contain, for example, 0.1 to 95% by weight, preferably 0.5 to 90% by weight of the active ingredient. The active compound mixtures according to the invention, in their commercially useful formulations and in the use forms prepared by them, may contain other active compounds, such as insecticides, fungicides, fungicides, growth regulators, etc. It can also be present as a formulation or as a mixture with herbicides. Here, the above-mentioned insecticides include, for example, organic phosphorus agents,
Examples include carbamate agents, chlorhydrocarbon agents, carboxylate agents, and insecticidal substances produced by microorganisms. Furthermore, the active compound mixtures according to the invention can also be present as mixtures with synergists; such formulations and usage forms may include those that are commercially useful. The synergist need not be active itself, but is a compound that amplifies the action of the active compound. The content of the active compound mixtures according to the invention in commercially useful use forms can vary within wide limits. The working concentrations of the active compound mixtures according to the invention are:
For example, it is 0.00001 to 100% by weight, preferably 0.001 to 5% by weight. The active compound mixtures according to the invention can be used in the customary manner adapted to the use form. EXAMPLES Next, the content of the present invention will be specifically explained with reference to Examples, but the present invention should not be limited thereto. Example 1 (i) Preparation of test compounds against brown planthopper Each active compound: 25-50 parts by weight Carrier: Mixture of diatomaceous earth and kaolin (1:5)
45 to 70 parts by weight Emulsifier: 5 parts by weight of polyoxyethylene alkyl phenylniter The above-mentioned amounts of active compound, carrier, and emulsifier are ground and mixed to form each wettable powder, and the prescribed dosage is diluted with water and mixed. Prepare. Test method: Three rice plants with a plant height of approximately 15 cm were planted in pots with a diameter of approximately 13 cm, and 10 days after planting, 20 ml of a diluted solution of the active compound in water with a predetermined concentration prepared in advance was sprayed on each pot using a spray gun. After air-drying the chemical solution, put it in a net basket in a pot and add one brown planthopper 4th instar larva.
Ten insects were inoculated per pot, and dead insects were counted three days later to calculate the insect kill rate. (ii) Test method for foliar spray efficacy test against rice blast disease Paddy rice (variety: Asahi) is cultivated in clay pots with a diameter of 12 cm, and at the 3rd to 4th leaf stage, 50 ml of a diluted solution of the active compound at a predetermined concentration prepared in advance is applied to 3 pots. Spread. The next day, a suspension of artificially cultured rice blast fungus spores was spray inoculated (twice) and kept in a humid room at 25°C and 100% relative humidity to allow infection. Seven days after inoculation, the degree of disease per pot was graded and evaluated according to the criteria below, and the control value (%) was determined. At the same time, drug damage was also investigated. Morbidity Spot area percentage (%) 0 0 0.5 Less than 2 1 3-5 2 6-10 3 11-20 4 21-40 5 Control value of 41 or more (%) = (Severity of disease in untreated area - in treated area Morbidity level / Morbidity level in untreated area) x 100 This test is the result of 3 pots in 1 area. The results of the above tests (i) and (ii) are summarized and shown in Table 1.

【table】

[Table] Example 2 The mixed composition of the present invention in Example 1 was used in a test plot where brown planthopper and rice blast disease occurred simultaneously, and as a result, the pests were completely controlled simultaneously with a control value of 100%. . Example 3 (hydrating powder) 25 parts of active compound of formula (), edifenphos 25
Part, mixture of powdered diatomaceous earth and powdered clay (1:
5) Grind and mix 45 parts of sodium alkylbenzene sulfonate, 2 parts of sodium alkylnaphthalene sulfonate formalin condensate, and prepare a wettable powder. Example 4 (Powder) 1 part of active compound of formula (), edifenphos 2
1 part and 97 parts of powdered clay were ground and mixed to make a powder.

Claims (1)

[Claims] 1 (1) General formula In the formula, X represents a lower alkyl group, a lower alkoxy group or a halogen atom, l represents 0, 1 or 2, and m represents 2 or 3, and (2) O-ethyl S, An agricultural insecticidal and fungicidal composition characterized in that it contains an active compound mixture consisting of S diphenylphosphorodithioate. 2 to the active compound mixture of (1) and (2) 4,5,
The agricultural insecticidal and fungicidal composition according to claim 1, which contains 6,7-tetrachlorophthalide.