JP2531996B2 - Insecticidal composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel insecticidal composition containing a nitro compound of the formula (I) described below and a known insecticidal compound as active ingredients and exhibiting an excellent insecticidal action.

The nitro compound of the formula (I) used in the present invention is described in Japanese Patent Application No. 63-299419 before the filing date of the present application, and has an insecticidal action itself.

Further, it is already known that the following drugs have insecticidal activity.

O, S-dimethyl acetylphosphoramide thioate, S, S '-[2- (dimethylamino) trimethylene] bis (thiocarbamate), N, N-dimethyl-1,2,3-trithian-5-ylamine, 2-isopropoxyphenyl methylcarbamate, 2-sec-butylphenyl methylcarbamate, 0,0-dimethyl 0-3,5,6-trichloro-2-pyridylphosphorothioate and 2- (4-ethoxyphenyl) -2-methyl Propyl
3-phenoxybenzyl ether, etc. [Pestayside Manual 7th Edition 1983 (The British Crop Protection
Published by Council)].

However, the known insecticidal compounds described above do not always show a satisfactory insecticidal effect, especially when the application concentration is low. In addition, as a result of using these insecticides for many years, some pests have acquired drug resistance and it has become difficult to control them.

The present inventors have now shown, as an active compound, a compound of formula (I): In the formula, R ¹ represents a hydrogen atom or a C _1-4 alkyl group, R ² represents —S—R ³ or Wherein R ³ represents a C _1-4 alkyl group, R ⁴ and R ⁵ each represent a hydrogen atom or a C _1-4 alkyl group, and Y represents CH or N. Compound, O, S-dimethyl acetylphosphoramidothioate, S, S '-[2- (dimethylamino) trimethylene] bis (thiocarbamate), N, N-dimethyl-1,2,3-trithiane-5 -Ylamine, 2-isopropoxyphenyl methylcarbamate, 2-sec-butylphenyl methylcarbamate, 0,0-dimethyl 0-3,5,6-trichloro-2-pyridylphosphorothioate and 2- (4-ethoxyphenyl)- 2-methylpropyl
It has been found that the novel active compound mixtures containing at least one selected from the group consisting of 3-phenoxybenzyl ether show excellent insecticidal activity.

Conventionally, various drugs have been developed as insecticides for agricultural and horticultural use, 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 each have a certain insecticidal effect, but have an insecticidal spectrum, an insecticidal effect (an insecticidal effect on various growth stages such as eggs, larvae, and adult worms), residual effect, 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.

Further, 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 (for example, leafhopper leafhoppers) of the hemiptera insect pest that have acquired resistance to organophosphorus insecticides and carbamate insecticides have recently appeared in paddy fields of various regions including the southwestern warm region of Japan, It is becoming difficult to control them, and development of excellent drugs is desired. In addition, aphids, mites, pests such as diamondback moth, which is a vegetable pest that harms cruciferous vegetables, and cotton ball worms, have acquired drug resistance, and control of such resistant pests or susceptible pests and resistant 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 cereals and pests of garden crops such as vegetables, flowers and fruit trees, tobacco,
For insect pests of industrial crops such as cotton and tea, forest pests, and pests of some of these horticultural crops, soil pests such as nematodes, sucking, feeding, and other various pests such as stored-grain pests. Therefore, the development of a drug having a superior effect is desired.

As a result of intensive studies to solve the above-mentioned various problems, the present inventors have surprisingly found that the nitro compound of the formula (I) is mixed with a known insecticidal compound to obtain the insecticidal activity of the active compound mixture according to the present invention. , Each exhibiting greater synergism and synergism than the sum of the effects of the active compounds alone.

That is, by applying the insecticidal composition according to the present invention, for example, paddy field pests, for example, planthoppers of hemiptera pests (green planthopper, sedge planthopper, etc.), lepidopteran pests and fruit trees, garden crop pests such as vegetable It has been found that, for example, the effects on the lepidopteran pests such as diamondback moth and the hemiptera pests on aphids can be achieved cooperatively and synergistically at a lower concentration than in the case of a single active compound alone.

Therefore, the insecticidal composition of the present invention is very effective in cultivating agricultural and horticultural crops, and provides an extremely outstanding technological progress in industrial utility.

Specific examples of the nitro compound of the formula (I) used in the insecticidal composition of the present invention include the following compounds.

1- (2-chloro-5-pyridylmethylamino) -1
-Methylthio-2-nitroethylene, 1- (2-chloro-5-pyridylmethylamino) -1
-Methylamino-2-nitroethylene, 1- (2-chloro-5-pyridylmethyl) -3-nitro-2-methylisothiourea, 3- (2-chloro-5-pyridylmethyl) -1 methyl-2- Nitroguanidine, 1- (2-chloro-5-pyridylmethylamino) -1
-Dimethylamino-2-nitroethylene, 1- [N- (2-chloro-5-pyridylmethyl) -N
-Methylamino] -1-methylamino-2-nitroethylene, 1- [N- (2-chloro-5-pyridylmethyl) -N
-Methylamino] -1-dimethylamino-2-nitroethylene, 3- (2-chloro-5-pyridylmethyl) -1,1-dimethyl-2-nitroguanidine, 1- (2-chloro-5-pyridylmethyl) Amino) -1
-Ethylamino-2-nitroethylene, 1-amino-1- [N- (2-chloro-5-pyridylmethyl) -N-methylamino] -2-nitroethylene, 3- (2-chloro-5-pyridyl Methyl) -1,3-dimethyl-2-nitroguanidine, 3- (2-chloro-5-pyridylmethyl) -1,1,3-
Trimethyl-2-nitroguanidine, 1-amino-1- [N- (2-chloro-5-pyridylmethyl) -N-ethylamino] -2-nitroethylene, 1- [N- (2-chloro-5- Pyridylmethyl) -N
-Ethylamino] -1-methylamino-2-nitroethylene, 1- [N- (2-chloro-5-pyridylmethyl) -N
-N-Propylamino] -1-methylamino-2-nitroethylene, 1- [N- (2-chloro-5-pyridylmethyl) -N
-Ethylamino] -1-ethylamino-2-nitroethylene, and 3- (2-chloro-5-pyridylmethyl) -3-ethyl-1-methyl-2-nitroguanidine.

The other known insecticidal compounds used in the insecticidal composition of the present invention include the following compounds.

O, S-dimethyl acetylphosphoramide thioate, (hereinafter abbreviated as acephate) S, S ′-[2- (dimethylamino) trimethylene] bis (thiocarbamate), (hereinafter abbreviated as cartap) N, N- Dimethyl-1,2,3-trithian-5-ylamine, (hereinafter abbreviated as thiocyclam) 2-isopropoxyphenyl carbamate, (hereinafter abbreviated as propoxur) 2-sec-butylphenyl methylcarbamate,
(Hereinafter abbreviated as BPMC) 0,0-dimethyl 0-3,5,6-trichloro-2-pyridyl phosphorothioate, (hereinafter abbreviated as chloropyrifosmethyl) and 2- (4-ethoxyphenyl) -2- Methylpropyl 3-phenoxybenzyl ether (hereinafter abbreviated as ethopheneprox).

The above insecticidal compounds are
e Pesticide Manual) 7th edition 1983 (The British Crop
It is already known as an insecticide in the Protection Council, etc.) and is known.

The weight ratio of active compounds of each group in the insecticidal composition can be varied within a relatively wide range. In general, for example, 0.05 to 20 parts by weight, preferably 0.1 to 10 parts by weight, of active compounds of the known insecticidal compound group are used per 1 part by weight of active compounds of the active compound group of the nitro compounds of the formula (I).

The insecticidal composition according to the present invention exhibits an excellent insecticidal activity, and thus can be used as an insecticide by foliage application, water or surface application, soil application, soil admixture treatment, nursery box application, and the like.

The insecticidal composition according to the present invention exhibits a strong insecticidal action. Therefore, it can be used as an insecticide. And, the active compound according to the present invention has no phytotoxicity to cultivated plants, and has low toxicity to warm-blooded animals, farm, forestry,
It can be used to precisely control pests, especially insects, in the protection of stored crops and products. They are usually active against susceptible and resistant species, and all or some stages of development.

For example, the insecticidal composition of the present invention, especially planthoppers such as planthoppers of Hemiptera pests (e.g., brown planthopper, scorpion planthopper, cuticle planthopper), leafhoppers, etc. It can be usefully used for controlling pests of garden crops such as genus and lepidopteran larvae of diamondback moth, bollworm, leaf beetle, and hemiptera pest scales, aphids, and fruit trees, and vegetables.

Further, in addition to the above-mentioned pests, the pests exemplified below can be effectively used.

As insects, pests of the order Coleoptera, such as the weevil Weevil (Callosobruchus chinensis) and the weevil Weevil (Sitoph
ilus zeamais), Tricium castan (Tribolium castan)
eum), Epilachna vigin
tioctomaculata), Black-necked rice (Agriot)
es fuscicollis), Rumex japonicum (Anomala rufocupre)
a), Colorado potato beetle (Leptinotarsa decemlin
eata), Diabrotica spp., Pine beetle (Monochamus alternatus), Rice weevil (Lissorhoptrus oryzophilus), Lyctus brunens: Lepidoptera, for example, Lymantria disparum (Lymantria dispar),
eustria), Atom beetles (Pieris rapae), Spodoptera litura (Spodoptera litura), Spodoptera litura (Mamestra brassica)
e), Nikameichiyu (Chilo suppressalis), Awanomeiga (Pyrausta nubilalis), Koadamadameiga (Ep)
hestia cautella), Red-faced Squirrel (Adoxophyes or
ana), Codling moth (Carpocapsa pomonella), Kaburagaga (Agrotis fucosa), Honey moth (Galleria mello)
nella), diamondback moth (Plutella maculipennis), heliotis (Heliotis virescens), citrus fruit moth (Phyl)
locnistis citrella); Hemiptera, such as leafhopper (Nephotettix cinc)
ticeps), brown planthopper (Nilaparvata lugens), brown planthopper (Laodelphax striatellus), white-bellied planthopper (Sogatella furcifera), stag beetle scale (P)
seudococcus comstocki), the scale bug (Unasp)
is yanonensis), green peach aphid (Myzus persica)
e), apple aphid (Aphis pomi), cotton aphid (Aphis gossypii), radish aphid (Rhop)
acosiphum pseudobrassicas), Nasi Gumbai (Stephan
itis nashi), blue bug (Nezara spp.), whitefly (Trialeurodes vaporariorum), psyllid (Psylla spp.); Orthoptera, for example, Gryllotalpa
africana), grasshopper (Locusta migratoria migratorio)
des); etc.

The pesticidal composition of the present invention may be in the form of a mixture of two components or in the form of a single conventional formulation 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, as a combustion device, fumigation and fumes cartridges, cans and coils), and ULV (cold mist
st), warm mist].

These preparations can be manufactured by a known method.
Such a process comprises, for example, applying an active compound to a developing agent, ie a liquid diluent; a liquefied gas diluent; a solid diluent, or a carrier, optionally a surfactant, ie an emulsifier and / or dispersant and / or This is done by mixing with a foam former. If water is used as the spreading agent, organic solvents, for example, can also be used as auxiliary solvents.

Examples of the liquid diluent or carrier include aromatic hydrocarbons (eg, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg, chlorobenzenes, ethylene chloride, chlorinated compounds). 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 normal temperature and pressure,
Examples include butane, propane, nitrogen gas,
Mention may be made of carbon dioxide, and aerosol propellants such as halogenated hydrocarbons.

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

Solid carriers for granules include crushed and fractionated rocks (e.g., calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic granules of inorganic and organic powders, and fine or organic materials ( For example, sawdust, coconut, corn cob and tobacco stem) can be mentioned.

Examples of 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 sulfates). , Aryl sulfonates, etc.)], and albumin hydrolysis products.

Dispersants include, for example, lignin sulphite waste liquors and methylcellulose.

Adhesives may also be used in the formulation (powder, granules, emulsions), such adhesives including carboxymethyl cellulose and natural and synthetic polymers (eg gum arabic, polyvinyl alcohol and polyvinyl acetate). You can

A colorant can also be used, and as such a colorant,
Inorganic pigments (eg iron oxide, titanium oxide and Prussian blue), and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes, and also iron,
Minor elements may be mentioned, such as salts of manganese, boron, copper, cobalt, molybdenum, zinc.

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

The insecticidal compositions of the present invention, in their commercially useful formulations and in the use forms prepared by these formulations, include other active compounds such as insecticides, baits, fungicides, acaricides, nematicides. It can also be present as a mixture with agents, fungicides, growth regulators or herbicides. Here, examples of the insecticide include carbamate agents, carboxylate agents, chlorinated and hydrocarbon 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 use forms including 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 insecticidal composition of the present invention in the commercially useful use forms can be varied within a wide range.

The use concentration of the insecticidal composition of the present invention is, for example, 0.0000.
1 to 100% by weight, preferably 0.001 to 1% by weight
Is.

The insecticidal composition of the present invention can be used by a usual method suitable for the use form.

When used as insect pests on stocks, active compounds are distinguished by good stability against alkali on lime material, as well as by good residual efficacy in wood and soil.

Next, the content of the present invention will be specifically described with reference to examples, but the present invention should not be limited to these.

Biological test: Test compound Compound of formula (I) No. 1: 1- (2-chloro-5-pyridylmethylamino) -1-methylamino-2-nitroethylene No. 2: 1- (2-chloro- 5-Pyridylmethylamino) -1-dimethylamino-2-nitroethylene No. 3: 1- [N- (2-chloro-5-pyridylmethyl) -N-methylamino] -1-dimethylamino-2-
Nitroethylene No.4: 3- (2-chloro-5-viridylmethyl) -1,1
-Dimethyl-2-nitroguanidine No. 5: 3- (2-chloro-5-pyridylmethyl) -1,3
-Dimethyl-2-nitroguanidine No.6: 1-amino-1- [N- (2-chloro-5-pyridylmethyl) -N-ethylamino] -2-nitroethylene No.7: 1- [N- (2-chloro-5-pyridylmethyl) -N-ethylamino] -1-methylamino-2-nitroethylene No. 8: 1- [N- (2-chloro-5-pyridylmethyl) -Nn- Propylamino] -1-methylamino-
2-Nitroethylene No. 9: 1- [N- (2-chloro-5-pyridylmethyl) -N-ethylamino] -1-ethylamino-2-nitroethylene No. 10: 3- (2-chloro- 5-pyridylmethyl) -3
-Ethyl-1-methyl-2-nitroguanidine Known insecticidal compound (A) Acephate (B) Cartapup (C) Thiocyclam (D) Propoxur (E) BPMC (F) Chlorpyrifos-methyl (G) Etofenproxus Example 1 Test for Preparation of test solution Solvent: Xylol 3 parts by weight Emulsifier: Polyoxyethylene alkylphenyl ether 1 part by weight Each active compound contains 1 part by weight of the above-mentioned amount of emulsifier to make a suitable active compound formulation. The above amount of solvent was mixed, and the mixture was diluted with water to a predetermined concentration.

Test method: Three rice plants with a plant height of about 15 cm planted in a vinyl pot with a diameter of 9 cm were planted, and 10 days after planting, 20 ml per pot of a water diluting solution of a predetermined concentration of the active compound prepared as described above was used with a spray gun. After spraying and air-drying the spray solution, cover it with a plastic net cylinder with a diameter of 9 cm and a height of 25 cm, inoculate 10 larvae of Cobb Noumea 4th instar per pot, place them in a temperature-controlled room and count the dead insects 2 days later to calculate the insecticidal rate. did. In addition, the test was conducted in two consecutive systems.

 The results are shown in Table 1.

Example 2 Test against diamondback moth Test method: A non-heading cabbage seedling of about 15 cm in height planted in a pot with a diameter of 9 cm was prepared by spraying a water-diluted solution of the active compound prepared as in Example 1 with a spray gun at 1 After spraying 20 ml per pot and air-drying the sprayed chemical solution, 10 inoculated 4th-instar larvae of Plutella xylostella, which are resistant to organophosphorus agents, were inoculated per pot and placed in a temperature-controlled room for 2 days to count the dead insects and calculate the insecticidal rate. In addition, the test was conducted in two consecutive systems.

 The results are shown in Table 2.

Example 3 Test against brown planthopper Test method: Three rice plants having a plant height of about 15 cm are planted in a pot having a diameter of about 13 cm, and 10 days after planting, a water-diluted solution of a predetermined concentration of the active compound prepared as in Example 1 is spray-gun. 20 per pot
After spraying, the spray solution was air-dried, a net was placed in the pot, and 10 fourth-instar larvae of the brown planthopper were inoculated per pot, and the pots were placed in a thermostatic chamber and the dead insects were counted 3 days later to calculate the insecticidal rate. The test is 2
I went on a cycle.

 The results are shown in Table 3.

Continuation of the front page (51) Int.Cl. ⁶ Identification number Reference number within the agency FI Technical display area A01N 47/22 A01N 47/22 A 57/16 102 57/16 102B 57/28 57/28 F

Claims (2)

(57) [Claims] 1. An active compound of the formula (I): In the formula, R ¹ represents a hydrogen atom or a C _1-4 alkyl group, R ² represents —S—R ³ or Wherein R ³ represents a C _1-4 alkyl group, R ⁴ and R ⁵ each represent a hydrogen atom or a C _1-4 alkyl group, and Y represents CH or N. Compound, O, S-dimethyl acetylphosphoramidothioate, S, S '-[2- (dimethylamino) trimethylene] bis (thiocarbamate), N, N-dimethyl-1,2,3-trithiane-5 -Ylamine, 2-isopropoxyphenyl methylcarbamate, 2-sec-butylphenyl methylcarbamate, 0,0-dimethyl 0-3,5,6-trichloro-2-pyridylphosphorothioate and 2- (4-ethoxyphenyl)- 2-methylpropyl
An insecticidal composition comprising at least one selected from the group consisting of 3-phenoxybenzyl ether. 2. The formula (I) is represented by 1- (2-chloro-5-pyridylmethylamino) -1-methylthio-2-nitroethylene, 1- (2-chloro-5-pyridylmethylamino) -1-.
Methylamino-2-nitroethylene, 1- (2-chloro-5-pyridylmethyl) -3-nitro-2-methylisothiourea, 3- (2-chloro-5-pyridylmethyl) -1methyl-
2-nitroguanidine, 1- (2-chloro-5-pyridylmethylamino) -1-
Dimethylamino-2-nitroethylene, 1- [N- (2-chloro-5-pyridylmethyl) -N-
Methylamino] -1-methylamino-2-nitroethylene, 1- [N- (2-chloro-5-pyridylmethyl) -N-
Methylamino] -1-dimethylamino-2-nitroethylene, 3- (2-chloro-5-pyridylmethyl) -1,1-dimethyl-2-nitroguanidine, 1- (2-chloro-5-pyridylmethylamino) ) -1-
Ethylamino-2-nitroethylene, 1-amino-1- [N- (2-chloro-5-pyridylmethyl) -N-methylamino] -2-nitroethylene, 3- (2-chloro-5-pyridylmethyl) ) -1,3-Dimethyl-2-nitroguanidine, 3- (2-chloro-5-pyridylmethyl) -1,1,3-trimethyl-2-nitroguanidine, 1-amino-1- [N- (2 -Chloro-5-pyridylmethyl) -N-ethylamino] -2-nitroethylene, 1- [N- (2-chloro-5-pyridylmethyl) -N-
Ethylamino] -1-methylamino-2-nitroethylene, 1- [N- (2-chloro-5-pyridylmethyl) -N-
n-Propylamino] -1-methylamino-2-nitroethylene, 1- [N- (2-chloro-5-pyridylmethyl) -N-
The insecticidal composition according to claim 1, which is ethylamino] -1-ethylamino-2-nitroethylene or 3- (2-chloro-5-pyridylmethyl) -3-ethyl-1-methyl-2-nitroguanidine. Stuff.