JPS63150204A - Insecticidal and fungicidal composition for agriculture - Google Patents

Abstract

PURPOSE:To obtain the titled composition exhibiting strong insecticidal and fungicidal effect, free from phytotoxicity to cultured plant, having low toxicity to warm-blooded animals and effective especially in controlling pathogens and vermin of rice plant, by using an imino-substituted heterocyclic compound and 4,5,6,7-tetrachlorophthalide as active components. CONSTITUTION:The objective composition contains an active compound mixture 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) 4,5,6,7-tetrachlorophthalide as active component. The amount of the component B is preferably 0.1-10pts.wt. per 1pt.wt. of the component A. The above active components are used in the form of a mixture or are separately prepared and mixed with each other in use. The concentration of the mixture in use is preferably 0.001-5wt%.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides a novel agricultural insecticidal and fungicidal composition which contains an imino-substituted heterocyclic compound of formula (1) below and a known fungicidal active compound as active ingredients and exhibits excellent insecticidal and bactericidal activity. relating to things.

The imino-substituted heterocyclic compounds of formula (I) 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.

Furthermore, it has already been described in Japanese Patent Publication No. 32592/1983 that 4,5,6,7-titrachloro7thalide (7thalide fthalide) 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, X represents S, CH2 or N-R2 (in the formula, R2 represents a hydrogen atom or an alkylcarbonyl group), and R1 is an optionally substituted pyridyl group (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) ), and the argument is 2
or 3, and Z represents NO2 or CN, and (2) a novel active mixture containing 4,5,6,7-titrachloro7thallide as an active ingredient is superior. It was found to exhibit insecticidal and bactericidal activity.

Conventionally, various pesticides have been developed as agricultural and horticultural insecticides, and can be 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 properties such as low toxicity, systemic transferability, low toxicity to fish and warm-blooded animals, reduced environmental pollution, and reduced number of applications and amount of applied drugs.

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

In particular, planthoppers and leafhoppers, which are bovine insect pests that have recently acquired resistance to organophosphorus insecticides and cicabamate insecticides, have been found in rice fields in various regions, including the warm southwest region of the country.
(For example, black leafhopper) have appeared and it has become difficult to control them, and there is a desire for the development of superior drugs. In addition, pests such as aphids, mites, vegetable pests that attack cruciferous vegetables, and cotton ballworms have acquired drug resistance, and it is necessary to control such resistant pests or treat susceptible 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 cultivation, WK box application is an excellent and non-toxic agent for pest control. development 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 species of these. There is a desire to develop a drug that has even better effects against pests of agricultural crops, soil pests such as wireworms, sweat-absorbing and feeding insects such as grain storage pests, and other various pests.

Furthermore, in addition to the development of excellent insecticides as described above, there is a desire to develop insecticides and fungicides that can simultaneously control rice blast, planthoppers, and leafhoppers, which are major diseases and pests in rice cultivation.

As a result of intensive research aimed at solving 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 4°5.6 The active mixture according to the invention consisting of .7-titrachlor 47-thallide exhibits a broad spectrum of effects that cannot be achieved by the effects of each active compound alone, and exhibits excellent insecticidal and fungicidal effects against rice diseases and insect pests. discovered.

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 represents an extremely outstanding technological advance in terms of industrial usefulness. It provides sex.

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

In the formula, (represents at least one selected from the group) or an optionally substituted thiazolyl group (the substituent represents at least one selected from a halogen atom or an alkyl group; the argument is 2).
or 3, and Z li:N O□ or CN.

In the general formula (1), preferably, ' 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 pyrinone The bonding position of the ring is the 3-position (or 5-position), the bonding position of the thiazole ring is the 5-position, and the eyelid is the 2-position.
or 3, and Z represents NO2 or CN.

As examples of imino-substituted heterocyclic compounds of general formula (1) used in the active substance combinations according to the invention, mention may be made of the following compounds:

1-(3-pyridylmethyl)-2-troimino)imidazoliqune, 1-(2-chloro-5-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-chloro-5-pyrimidylmethyl)-2 -troimino)tetrahydropyridine, 1-(2-fluoro-5-pyridylmethyl)-2-troimino)imidazoliqune, 1-(2-fluoro-5-pyridylmethyl)-2-troimino)tetrahydropyrimidine, 1- (2-bromo-5-pyridylmethyl)-2-troimino)imidazoliqune, 1-(2,3-cyclo5-pyridylmethyl)-2-
1-(2-methyl-5-pyridylmethyl)-2-troimino)imidazoliqune, 1-(2-methyl-5-pyridylmethyl)-2-troimino)imigzolin, 1-(2-methyl-5-pyridylmethyl)-2-troimino)tetrahydropyrimidine, -Chloro-5-thiazolylmethyl)-2-troimino)imidazolidine, 1-(2-chloro-5-thiazolylmethyl)-2-troimino)tetrahydropyrimidine, 1-(2-fluoro-5-thiazolylmethyl)-2- 1-(2-methyl-5-thiazolylmethyl)-2-troimino)imidazolidine, 1-(2-methyl-5-thiazolylmethyl)-2-troimino)tetrahydropyrimidine, 1-acetyl- 3
-(2-chloro-5-pyridylmethyl)-2-totroimino)imidazoliqune, 1-7 cetyl-3-(2-rip
rho-5-pyridylmethyl)-2-troimino)tetrahydropyrimidine, 1-butyryl-3-(2-chloro-
4-Fluoro-5-pyridylmethyl)-2-troimino)imidazolidine, 3-(2-chloro-5-pyridylmethyl)-2-troimino)thiazolidine, 3-(2-chloro-5-pyridylmethyl)- 2-troimino)tetrahydro-2H-1,3-thianone, 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)picridine, 1-( 2-chloro-5-pyridylmethyl)-2-(cyanoimino)imidacilline, 1-(2-chloro-5-pyridylmethyl)-2-(cya/imi/)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-28-1,3-thiazine ,1
~(2-Fluoro-5-pyridylmethyl)-2-(cyanoimino)thiazolidine, 1-(2-rya-5-thiazolylmethyl)-2-(
cyanoimino)thiazolidine, 1-(2-chloro-5-thiazolylmethyl)-2-(cyanoimino)tetrahydro-2H-1,3-thiazine.

4,5,6,7-titrachloro7, one of the fungicidal active substances used in the active substance combination according to the invention
Talid is expressed by the following formula.

In the present invention, the weight ratios of the active compounds of each group in the active substance combination can vary within a relatively wide range, generally (1) the activity of the imino-substituted heterocyclic compound of general formula (1); per part by weight of active compound of the group of compounds (
The active compound of 4.5.6.7-titrachloro7thallide in 2), for example 0.05 to 20 parts by weight, preferably 0.1 to 20 parts by weight.
It can be used at 10 parts by weight.

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. 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.

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

Insects include Coleoptera pests, such as the rice weevil (
Lissorhoptrus oryzophilu
s), rice weevil (Echinoeinemus)
squareus), rice beetle (Oulema
oryzae); lepidopteran insects, such as Chilo 5uppressal
is), Robnomeiff (Cnaphalocroci)
s medinalis), 7 Taobikoya (N B
r1lB aenescens), P. arnara guttata'.

Cathopteran insects, such as N ephotettix ei
netieeps), brown planthopper (Nilapar)
vata lugens), brown planthopper (L a
odelphax lugens), white-legged planthopper (
S ogatella furcifera)s green stink bug (Nezara spp, L orthoptera, e.g.
, locust (Locusta migratoria)
As diseases, for example, archaeal fungi [ArchiBeetes], algal fungi [Phycomycetes];
es)], Ascomycetes [Ascomycetes (A 5coII
Iycetes)], Basidiomycetes [Basidiomycetes (B
asidiomycetes), Deuteromycetes [7.
ecti)] and various other plant diseases caused by bacteria.

As a representative example of the bactericidal spectrum of the above-mentioned plant diseases, for example, rice blast mW (Pyricularia or
yzae), Sesame leaf blight fungus (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 can be in the form of a mixture of components (1) and (2) or each can be in the form of customary preparations individually for extemporaneous mixing. And such forms include solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active compound infiltration - natural and synthetic, Microkabcef 1 seed coatings, with combustion devices. Preparations (e.g. combustion equipment such as fumigation and fume cartridges, guns and coils), ULV [cold mist]
, warm mist (warm m1st)].

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 (e.g., aObenzenes, ethylene chloride, etc.). , methylene chloride, etc.), aliphatic hydrocarbons [e.g., cyclohexane, etc., puffins (e.g., mineral oil fractions, etc.) 1, alcohols (e.g., butanol, glycol, and their ethers, esters, etc.), ketones (e.g., , acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strongly polar solvents (eg dimethyl formamide, dimethyl sulfoxide, etc.) and water.

Liquefied gas diluents or carriers are gases at room temperature and pressure, examples of which include butane, propane, nitrogen gas, carbon dioxide, and aerosol propellants such as adenated hydrocarbons. can.

Solid diluents include soil natural minerals (e.g. kaolin, clay, talc, chalk, quartz, attapulgite,
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,
J1 albumin hydrolysis products (alkyl sulfonates, alkyl sulfates, arylsulfonates, etc.) can be mentioned here.

Dispersants include, for example, genin sulfide waste liquor and methylcellulose.

Adhesives can also be used in the formulation (powders, granules, emulsions); examples of such adhesion 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 alizarin dyes, azo dyes or gold II
organic dyes such as L7 talocyanine dye, and furthermore,
Mention may be made of trace elements such as iron, manganese, boron, copper, lobalt, molybdenum, their salts of zinc.

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

The active substance combinations 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 or It can also be present as a mixture with herbicides. Here, the above-mentioned insecticides include, for example, organic phosphorus agents, carbamate agents, chlorinated hydrocarbon agents,
Examples include carboxylate drugs and insecticidal substances produced by microorganisms.

Furthermore, the active substance combinations 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
, ooooi 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.

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 algae 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 form each wettable powder, and a predetermined amount of the powder is diluted with water and mixed. do.

Test method: Three rice plants with a plant height of 15 cm were planted in pots with a diameter of about 13 cm, and 10 days after planting, a pre-prepared water dilution of Active Co., Ltd. at a predetermined concentration was applied to each pot using a spray gun.
- After spraying and air-drying the sprayed chemical solution, the pots were screened and inoculated with 10 4th instar brown planthopper larvae per pot, and after 3 days, the dead insects were counted and the killing 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 diluted solution of the active compound at a predetermined concentration was sprayed at 950 ml 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 per pot 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 Table 1.

Table 1 Note 1: No drug 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
-(=)loimino)imigzolin, compound No. 2
1-(2-chloro-5-pyridylmethyl)-2-totroimino)tetrahydrotetrapyrimidine, Compound No. 3 1-(2-chloro-5-thiazolylmethyl)-2-totroimino)imidazolidine, Compound No. 4 1-acetyl-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)imigzolidine.

3. Compounds used in the present invention: Compound (A) Niathalide 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 were occurring at the same time. Complete simultaneous control was achieved with a control value of %.

Example 3 (hydrating powder) 25 parts of active compound of formula (I), 25 parts of fusaride, 45 parts of a mixture of powdered diatomaceous earth and powdered clay (1:5),
2 parts of sodium alkylbenzene sulfonate and 3 parts of sodium alkylnaphthalene sulfonate formalin complex are pulverized and mixed to prepare an irrigation agent.

Example 4 (Powder) 1 part of the active compound of formula (I), 2.5 parts of 7 salide, and 96.5 parts of powdered clay were ground and mixed to make a powder.

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) 4,5,6,7-tetrachlorophthalide.