JPS63150205A - Insecticidal and fungicidal composition for agriculture - Google Patents

Abstract

PURPOSE:To obtain the titled composition free from phytotoxicity to cultured plants, having low toxicity to warm-blooded animals and effective in surely controlling pathogens and vermin of especially rice plant, by using a mixture of active compounds consisting of an imino-substituted heterocyclic compound and an O-ethyl compound, etc., as active components. CONSTITUTION:The objective composition contains a mixture of active compounds consisting of (A) an imino-substituted heterocyclic compound of formula [X is S, CH2 or N-R<2> (R<2> is H or alkylcarbonyl; R<1> is pyridyl or thiazolyl; n is 2 or 3; Z is NO2 or CN] and (B) O-ethyl; S,S-diphenyl; phosphorothioate, as active components. The amount of the component B is preferably 0.1-10pts.wt. per 1pt.wt. of the compound of formula. The above components are preferably further incorporated with 0.1-10pts.wt. of 4,5,6,7- tetrachlorophthalide.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides a novel agricultural insecticidal sterilizer that contains an imino-substituted polycyclic compound of formula (1) below and a known fungicidally active compound as an active ingredient and exhibits excellent insecticidal and bactericidal activity. Regarding composition.

The imino-substituted heterocyclic compounds of formula <1) used in the present invention and their use as insecticides are disclosed in Japanese Patent Application No. 60-106
No. 854, Japanese Patent Application No. 1982-219082 and Japanese Patent Application No. 1983
-48629.

In addition, it has already been reported in Japanese Patent Publication No. 12-12 that 0-ethyl S,S diphenyl phosphorodithioate (edifenphos) has control activity against rice blast.
It is described in Publication No. 919. Furthermore, 4°5.6.7
-Chitrak four mouths 7 thalid (7 thalid)
It has already been described in Japanese Patent Publication No. 32592/1983 that e) has a control activity against rice blast.

However, the effect of these active compounds is either an insecticidal effect or a bactericidal effect when used alone, and it is not possible to simultaneously control diseases caused by pathogenic bacteria and damage caused by insect pests.

According to the present inventors, (1) In the general formula, (The substituent represents at least one selected from a halogen atom or an alkyl group) or an optionally substituted thiazolyl group (The substituent represents at least one selected from a halogen atom or an alkyl group) - represents 2
or 3, and Z represents N02 or CN, and a novel active mixture containing as active ingredients an imino-substituted heterocyclic compound of (2) O-ethyl S,S diphenyl phosphorodithioate. It was found to exhibit insecticidal and bactericidal activity.

Conventionally, various pesticides have been developed as insecticides for concentrated horticulture, 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), residual effect, and immediate effect. However, they do not fully satisfy various characteristics such as low toxicity, systemic transferability, low toxicity to fish and blood-stained animals, reduced environmental pollution, and reduced number of applications and amount of applied drug.

Furthermore, as a result of the extensive use of conventional chemicals, various insect pests have emerged that have acquired resistance to them.

In particular, hemiptera pests such as the planthopper leafhopper M (e.g. leafhopper M) have recently acquired resistance to organophosphate insecticides and carbamate insecticides in rice fields across the country, including the warm southwestern regions of the country. Since these insects have appeared and their control has become difficult, the development of superior drugs is desired.

Furthermore, Kona, which is a vegetable pest that attacks aphids, mites, and cruciferous vegetables, has acquired drug resistance in cotton poleworms and other pests. It is desired to develop an excellent drug that can simultaneously control resistant pests.

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 fields, 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, such as the rice weevil, which have become a particular problem in recent years.

Therefore, important pests of food crops including rice and its crustaceans, pests of horticultural crops such as vegetables, flower petals, and fruit trees, pests of craft crops such as tobacco, cotton, and tea, forest pests, and certain types of these pests. It is desired to develop a drug that has even more excellent effects against pests of greenhouse horticulture crops, soil pests such as rays, sweat-absorbing and feeding insects such as grain storage pests, and other various pests.

Furthermore, along with the development of excellent insecticides as mentioned above, it has become especially important for rice cultivation. It is desired to develop an insecticide and fungicide that can simultaneously control rice blast, planthoppers, and leafhoppers, which are diseases and pests.

As a result of intensive research to solve the various problems described above, the present inventors surprisingly found that (1) the imino-substituted heterocyclic compound of the formula (1) and (2) the known 0.ethyl S, S
- The active mixture according to the invention consisting of diphenyl phosphorodithioate exhibits excellent synergistic and synergistic effects unexpected from the effects of each active compound alone, resulting in excellent insecticidal and fungicidal effects against rice diseases and insect pests. I discovered that it shows.

Therefore, the insecticidal and fungicidal composition of the present invention is very effective in agricultural crop cultivation, for example, in particular, simultaneous control of pests and labor saving, and has extremely outstanding technological progress in terms of industrial utility. It provides:

The imino-substituted heterocyclic compounds of general formula (1) used in the active substance combination according to the invention are defined as follows.

In the formula, represents an optionally substituted thiazolyl group (the substituent represents at least one selected from a halogen atom or an alkyl group), and m is 2.
or 3, and Z represents N O2 or CN.

In the general formula (1), preferably, , R1 represents a pyridyl group substituted with one or two selected from chloro atom, bromine atom, fluoro atom, or methyl group, or a thiazolyl group substituted with chloro atom, fluoro atom, bromine atom, or methyl group, and The bonding position of the pyridine ring is the 3-position (or 5-position), the bonding position of the thiazole ring is the 5-position, and the ring is the 2-position.
or 3, and Z represents NO□ or CN.

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

1-(3-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-chloro-5-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-chloro-5-pyridylmethyl) -2-troimino)tetrahydropyridine, 1-(2-fluoro-5-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-fluoro4-5-pyridylmethyl)-2-nitroimino)tetrahydro Pyrimidine, 1-(2-bromo-5-pyridylmethyl)-2-(nitroimino)imidazolidine, 1-(2,3-dichloro-5-pyridylmethyl)-2-
1-(2-methyl-5-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-methyl-5-pyridylmethyl)-2-troimino)imigzolin, 1-(2-methyl-5-pyridylmethyl)-2-troimino)tetrahydropyrimidine, 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, 1-7 Cetyl-3-(2-chloro-5-pyridylmethyl)-2-to-troimino)imidazolidine, 1-7 cetyl-3-(2-chloro-5-pyridylmethyl)-2-to-troimino)tetrahydropyrimidine, 1-butyryl -3-(2-chloro-4-fluoro-5-pyridylmethyl)-2-troimino)imidazolidine, 3-(2-chloro-5-pyritylmethyl)-2-troimino)thiazolidine, 3-(2- chloro-5-pyridylmethyl)-2-to-troimino)tetrahydro-2H-1,3-thiazine, 3-
(2-fluoro-5-pyridylmethyl)-2-troimino)thiazolidine, 1-(2-chloro-5-pyridylmethyl)-2-troimino)pyrrolidine, 1-(2-chloro-5-pyrinolmethyl)- 2-troimino)piperidine, 1-(2-bromo-5-pyridylmethyl)-2-troimino)pyrrolidine, 1-(2-fluoro-5-pyridylmethyl)-2-troimino)bitolysine, 1 -(2-di0-5-pyridylmethyl)-2-(cyanoimino)imigzolin, 1-(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-thiazo2-normethyl)-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)tetrahuman t7-2H-,IJ-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.

11-One of the fungicidal active substances used in the active substance combination according to the invention, 0-ethyl S,S-diphenyl phosphorodithioate, has the following formula:

In addition, the active substance combination of (1) and (2) according to the present invention may further contain 4,5°6.7 of (3).
-Tetrachlorophthalide is represented by the following formula.

In the present invention, the active substance, the weight ratio of each group of active compounds in the substance composition can be varied within a relatively wide range. per part by weight of active compound of the active compound group of cyclic compounds,
0-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 further 4.5, 6.7 parts of (3)
- When adding tetrachlorophthalide, the component (3) should be added, for example, from 0.05 to 20 parts by weight, preferably from 0.1 to 20 parts by weight.
10 parts by weight can be used.

The active substance combination according to the present invention exhibits excellent insecticidal and fungicidal activity and can be used as an insecticidal fungicide, for example, by spraying on foliage, applying in water or on the surface of water, applying to soil, mixing with soil, applying in seedling boxes, etc.

The active substance combinations according to the invention exhibit a strong insecticidal and fungicidal action. Therefore, it can be used as an insecticide and fungicide. Furthermore, the active compound according to the present invention has no phytotoxicity to cultivated plants (and has low toxicity to warm-blooded animals), and can accurately control pests, especially insects and diseases, in agriculture, particularly in the protection of rice. They end up in use for
Usually active against sensitive and resistant species and against all or some growth stages.

The above-mentioned pests (S damage and pests) include, for example, the following. Examples of such pests include the following.

Insects include Coleoptera pests, such as the rice weevil (
L 1ssorhoptrus oryzophil
us), rice weevil (Eel+inoeinemus)
5quaa+eus), rice beetle (Oul
ema oryzae); lepidopteran insects, such as Chilo 5uppressal
is) 1 Cnaphalocroe
is medinalis), 7 taobiko〃ya (N
araBa aenescens), P arnara guttata; bovine insects such as N ephotettix ei
ncticeps), brown planthopper (N 1lapa)
rvata lugens), brown-bottomed planthopper (L.
aodelphax lugens), green planthopper (Sogatella furcifera), green stink bug (Nezara spp,); orthoptera insects, e.g.
), locust (L oeusta migratori)
a migratoriodes); as a disease,
For example, archaeal fungi [Archimycetes]
s)], algae [P hycomycetes
tes)], ascomycetes [A seom
yeetes)], Basidiomycetes [B a
sidiomyetetes), M. imperfecti [7.
ti)], and various other plant diseases caused by bacteria.

As a representative example of the bactericidal spectrum of the above plant diseases, for example, rice blast fungus (Pyricularia or
yzae), Sesame leaf blight (Cohliobolus mlyabeanu), a type of pathogenic fungus that causes rice ear blight.
s), etc., but the bactericidal spectrum should not be limited to these.

The active substance combinations according to the invention end up in the form of a mixture with components (1) and (2) and optionally component (3), or each in the form of a customary preparation on its own for extemporaneous mixing. Such forms include solutions, emulsions, suspensions, powders, foams, bases, granules, aerosols, active compound infiltration - natural and synthetic, microcapsules, seed coatings, combustion devices. Combustion devices such as fumigation and fume cartridges, guns and coils, and ULV [cold mist]
5eist), warm mist (wars m1s
t)].

These formulations can be manufactured by known methods. Such a process can be carried out, for example, by combining the active compound with a spreading agent, i.e. a liquid diluent; a liquefied gas diluent; a solid diluent; or a carrier, optionally a surfactant, i.e. an emulsifying agent and/or a dispersing agent and/or This can be done by using a foam-forming agent and mixing.

When using water as extender, 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 (
For example, chlorobenzenes, ethylene chlorides, methylene chloride, etc.), aliphatic hydrocarbons (e.g., cyclohexane, etc., paraffins (e.g., mineral oil fractions, etc.)), alcohols (e.g., butanol, glycols and their ethers, esters, etc.), ketones (eg acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, etc.), strongly polar solvents (eg dimethylformamide, trimethylsulfoxide, 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, chalk, quartz, heptadaloid,
montmorinite, diatomaceous earth, etc.), and soil synthetic minerals* (for example, highly dispersed silicic acid, alumina, silicates, etc.).

Solid carriers for granules include crushed and fractionated rocks (for example, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic granules of inorganic and organic koji powder, and fine granules of organic substances ( (for example, sawdust, coconut berries, corn cobs, tobacco stalks, etc.).

Examples of emulsifiers and/or foaming agents include nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (
For example, alkylaryl polyglycol ethers,
Examples include alkyl sulfonates, alkyl sulfates, arylsulfonates, and albumin hydrolysis products.

Dispersants include, for example, lignin sulfide 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, such as inorganic pigments (e.g. iron oxide, titanium oxide and Prussian blue), and organic dyes such as alizarin dyes, azo dyes or metal-7 talocyanine dyes, and also Mention may be made of such trace elements as their salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

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

The active substance combinations of the invention, in their commercially useful formulations and in the use forms prepared by their formulations, also contain other active compounds, such as insecticides, fungicides, fungicides, vegetative agents, etc. It can also be present as a mixture with regulators or herbicides. Here, as the above-mentioned insecticide, for example,
Examples include organic phosphorus agents, carbamate agents, chlorinated hydrocarbon agents, carpoxylate 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 formulations and usage forms can 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 substance combinations 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, o
, o o o o i to ioo weight %, preferably o, ooi to 5 weight %.

The active compound mixtures according to the invention can be used in the customary manner adapted to the use form.

Next, the content of the present invention will be specifically explained with reference to Examples.
The present invention should not be limited to this only.

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) 45-7
0 parts by weight Emulsifier: 5 parts by weight of polyoxyethylene alkyl phenyl ether The above-mentioned amounts of active compound, carrier and emulsifier are pulverized and mixed to prepare each irrigation agent, and the prescribed amount is diluted with water and mixed. .

Test method: Three rice plants with a plant height of about 15 cm were planted in pots with a diameter of about 13 cm, and 10 days after planting, a water dilution of the active stock λ company prepared in advance at a predetermined concentration was applied using a spray gun to spray 2 rice plants per pot.
After air-drying the sprayed chemical solution, the pots were covered with net baskets and 10 4th instar brown planthopper larvae were inoculated per pot.After 3 days, dead insects were counted and the insecticidal rate was calculated.

(ii) Test method for foliar spray efficacy test against rice blast disease Paddy rice (quality: Asahi) was cultivated in a clay pot with a diameter of 12 cm.
At the 3rd to 4th leaf stage, a pre-prepared dilution of the active compound at a predetermined concentration was sprayed at 50°C per 3 pots. The next day, a suspension of artificially cultured rice blast fungus spores was spray inoculated (twice), and the temperature was increased to 25°C.
The cells were kept in a greenhouse at 100% relative humidity and infected. Inoculation 7
After a day, the degree of disease in pot @9 was graded and evaluated according to the following criteria, and the control value (%) was determined. At the same time, drug damage was also investigated.

Morbidity Level Lesion area ratio (%) 0.5 Less than 2 1 2 to less than 5 2　　　　　　5～10 3 10 to less than 20 4 20 to less than 40 5 40 or more This test is the result of 3 pots in 1 section.

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

Table 1 Table 2 Note 1: No chemical damage was observed in all the mixtures and single agent uses of Example 1 (i) and (ii).

2. Compound of general formula (1) used in the present invention: Compound N
o, 1 1-(2-chloro-5-pyridylmethyl)-2
Compound No. 2 1-(2-chloro-5-pyridylmethyl)-2-troimino)imidacilline, Compound No. 3 1-(2-chloro-5-thiazolylmethyl)-2-( imidazolidine, compound No. 4 1-7 cetyl-3-(2-chloro-5
-pyridylmethyl)-2-troimino) imidazolidine, compound No. 5 3-(2-chloro-pyridylmethyl)
-2-troimino)thiazolidine, Compound No. 6 1-(2-chloro-5-pyridylmethyl)-2-troimino)piperidine, Compound No. 7 1-(2-chloro-5-pyridylmethyl)-2 -(cyanoimino)imidazolidine.

3. Compounds used in the present invention: Compound (A): Nidifenphos Compound (B): 7 Salide Example 2 The mixture composition of the present invention in Example 1 was used in a test plot where brown planthopper and rice blast disease occur simultaneously. As a result, the pests were completely controlled simultaneously with a control value of 100%.

Example 3 (Irrigation agent) 25 parts of the active compound of formula (I), 25 parts of Niji7konphos,
45 parts of a mixture of powdered diatomaceous earth and powdered clay (1:5), 2 parts of sodium alkylbenzenesulfonate, 3 parts of sodium alkylnaphthalenesulfonate formalin complex
Grind and mix the remaining parts to make an irrigation agent.

Example 4 (Powder) 1 part of the active compound of the formula (1), 2 parts of Niji7-Konphos, and 97 parts of powdered clay were pulverized and mixed to prepare a powder.

Procedural amendment April 21, 1986

Claims (1)

[Claims] 1. (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) In the formula, X is S, CH_2 or N-R^2 (in the formula, R^2
represents a hydrogen atom or an alkylcarbonyl group), and R^1 represents an optionally substituted pyridyl group (the substituent represents at least one selected from a halogen atom or an alkyl group) or a substituted is a thiazolyl group (the substituent represents at least one selected from a halogen atom or an alkyl group), m represents 2 or 3, and Z represents NO_2 or CN, an imino-substituted heterocycle of An agricultural insecticidal and fungicidal composition characterized in that it contains an active compound mixture consisting of a compound of formula (2) and (2) O-ethyl S,S diphenyl phosphorodithioate. 2, 4, 5, 6 in the active compound mixture of (1) and (2)
, 7-tetrachlorophthalide. 7-tetrachlorophthalide.