JPH0625041B2 - Agro-horticultural insecticidal composition - Google Patents

Description

The present invention relates to novel agricultural and horticultural active compound mixtures of nitromethylene derivatives with known carbamates having excellent insecticidal activity.

It has been found by the present applicant that the nitromethylene derivative has an excellent insecticidal activity and has already been filed [Japanese Patent Application Laid-Open No. 60-172976 (Japanese Patent Application No. 59-26020), Japanese Patent Application Laid-Open No. 60-218386 (Japanese Patent Application No. 59-72966),
Japanese Patent Application Laid-Open No. 61-12682 (Japanese Patent Application No. 59-13294)
3)].

It is already known that the following carbamates have insecticidal activity. For example, 2-iso-propoxyphenylmethylcarbamate, 2-sec-butylphenylmethylcarbamate, o-cumenylmethylcarbamate and the like.

However, the action of these known carbamates is not always satisfactory, especially when the active compound concentration is low and when only small amounts are applied. In addition, as a result of using these insecticides for several years, some pests have acquired resistance, and the control of these pests has become very difficult.

(I) 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 a nitromethylene derivative and (2) 2-isopropoxy group Enyl methyl carbamate, o-cumenyl methyl carbamate, 2-sec-butylphenyl methyl carbamate, 3,4-xylyl methyl carbamate, m-tolyl methyl carbamate, α-ethylthio-o-tolyl methyl carbamate, 2-dimethylamino-5,6 -Dimethylpyrimidine-4
-Yl dimethylcarbamate, 2,2-dimethyl-1,3-benzooxol-4-yl methylcarbamate, 2,3-dihydro-2,2-dimethylbenzofuran-7
-Yl methyl carbamate, 2,3-dihydro-2,2-dimethylbenzofuran-7
-Yl- (dibutylaminothio) (methyl) carbamate and 2,3-dihydro-2,2-dimethylbenzofuran-7
It has been found that a novel active compound mixture of at least one carbamate selected from -yl-N- (N-isopropyl-N-ethoxycarbonylethylaminosulfenyl) -N-methylcarbamate exhibits excellent insecticidal activity. It was

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 pesticides, although each has a certain insecticidal effect, insecticidal spectrum, insecticidal effect (various growth stages, such as eggs, larvae, adult insect insecticidal effect), residual effect, fast-acting. 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 of the hemiptera insect pests (for example, leafhopper leafhoppers) that have acquired resistance to organophosphorus insecticides and carbamate insecticides in paddy fields in various regions including the southwestern warm region of Japan in recent years have emerged, It is becoming difficult to control them, and development of an excellent drug is desired. Furthermore, pests such as aphids, mites, vegetable pests such as diamondback moth and cotton ball worms that injure cruciferous vegetables 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 a 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 petals 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 insects,
It is desired to develop a drug having an even more excellent effect on sucking and feeding of stored grain pests and other various pests.

As a result of earnest studies to solve the above-mentioned various problems, the present inventors have surprisingly found that the active compound mixture of the present invention containing the known carbamate in the nitromethylene derivative has a single insecticidal activity. It has been found that it exerts greater cooperation and synergy than the sum of the effects of.

That is, by applying the insecticidal composition according to the present invention,
For example, effects on paddy field pests, such as hemiptera planthoppers (e.g., brown planthoppers) and vegetable pests, such as hemiptera pest aphids, are cooperative and synergistic at lower concentrations than the sole active compound alone. I have found that I can achieve.

Therefore, the insecticidal composition of the present invention is very effective in cultivating agricultural and horticultural crops, and provides extremely excellent technical suitability in terms of industrial utility.

The nitromethylene derivatives of general formula (I) used in the active compound mixtures according to the invention are defined as follows: 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.

Particularly preferred nitromethylene derivatives of general formula (I) for use in the active compound mixtures according to the invention are defined below.

In the general formula (I), X preferably represents a methyl group, a methoxy group, a chlorine atom, a bromine atom or a fluoro atom, l represents 1 or 2, m represents 2 or 3, and The bonding position is 3-position (or 5-position).

The nitromethylene derivative of the general formula (I) may be present in the form of a salt, and examples of the salt include inorganic acid salts,
Sulfonates, organic acid salts, metal salts and the like, preferably, for example, hydrochloride, p-toluene sulfonate, cupric acetate, succinate and the like can be mentioned. Therefore, the nitromethylene derivative of the formula (I) used in the present invention is a designation including its salt form.

Examples of nitromethylene derivatives of general formula (I) for use in the active compounds according to the invention include the following 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- Pyridylmethyl) -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-full -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- (nitro Methylene) 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- (d Rhomethylene) 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-acetic acid cupric salt, 1- (2-bromo-5- Pyridylmethyl) -2- (nitromethylene) imidazolidine-succinate, 1- (2,4-dichloro-5-pyridinemethyl) -2- (nitromethylene) tetrahydropyrimidine-p-toluenesulfonate.

It has been found by the present applicant that the nitromethylene derivative of the general formula (I) has an insecticidal activity and has been filed [Japanese Patent Application Laid-Open No. 60-172976 (Japanese Patent Application No. 59-2602).
0), JP-A-60-218386 (Japanese Patent Application No. 59-729).
66), Japanese Patent Application Laid-Open No. 61-12682 (Japanese Patent Application No. 59-132).
943)].

The following carbamates which are one component of the active compound mixtures according to the invention are known.

2-iso-propoxyphenyl methyl carbamate (propoxur), o-cumenyl methyl carbamate (isoprocarb
carb), 2-sec-butylphenylmethylcarbamate (BPM
C), 3,4-xylylmethyl carbamate (xylylcarb xy
lylcarb), m-tolylmethyl carbamate
b), α-ethylthio-o-tolylmethylcarbamate (ethiofenecarb ethiofencarb), 2-dimethylamino-5,6-dimethylpyrimidin-4-yldimethylcarbamate (pirimicarb pirimicarb), 2,2-dimethyl-1,3 -Benzodioxol-4-ylmethylcarbamate (benziocarb bendiocarb), 2,3-dihydro-2,2-dimethylbenzofuran-7-ylmethylcarbamate (carbofuran carbofuran), 2,3-dihydro-2,2-dimethyl Benzofuran-7-yl-
(Dibutylaminothio) (methyl) carbamate (carbosulfan carbosulfan), 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N- (N-isopropyl-N-ethoxycarbonylethylaminosulfenyl)- N-methyl carbamate (aminosulfulan), a carbamate which is one component of the active compound mixture according to the invention, is already known. That is, for example, The Pesticide Manual 7th edition 1
983 (The British Crop Protection Council
(Published), etc., and is already known as an insecticide.

The weight ratio of the active compounds of the groups in the active compound mixture can be varied within a relatively wide range. In general,
(2) Active compound of the active compound group of the carbamate, for example 0.1 to 20 parts by weight, preferably 0.2 parts by weight, per 1 part by weight of the active compound of the active compound group of the nitromethylene derivative of the general formula (I). ~ 15 parts by weight are used.

The active compound mixtures according to the invention exhibit an excellent insecticidal activity. Therefore, the active compound mixture, as an insecticide,
It can be used by foliage spraying, underwater or water surface application, soil application, soil admixture treatment, nursery box application and the like.

The active compound mixtures according to the invention exhibit a strong insecticidal action. Therefore, it can be used as an insecticide. The active compound according to the present invention has no phytotoxicity to cultivated plants and has low toxicity to warm-blooded animals, and accurately controls pests, especially insects in the protection of agriculture, forestry, stored crops and products. Can be used for They are usually
Active against sensitive and resistant species, and all or some stages of development.

For example, the insecticidal composition of the present invention, especially planthoppers of hemiptera pests (e.g., planthopper planthopper, stilrow planthopper, brown planthopper), leafhoppers, etc. It can be effectively used for controlling pests of garden crops such as fruit trees and vegetables.

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

As insects, Coleoptera pests such as Azuki bean weevils (Callosobruchus chinensis), Weevil Weevil (Sitophilus zeamais), Welsh beetle (Tri
bolium castaneum)
na vigintioctomaculata)
(Agriotes fuscicollis), Japanese beetle (Anomala rufoc)
uprea), Colorado potato beetle (Leptinotarsa decem)
kineata), Diabrotica spp., Monochamus alternatus, Rice weevil (Lissorhoptrus oryzophilus), Flat beetle (Lyctus bruneus);
oma neustria), caterpillar (Pieres rapae), Spodoptera litura, Spodoptera litura (Mamestra brassic)
ae), Nikameichiyu (Chilo suppressalis), Awanomeiga (Pyrausta nubilalis), Koadamadameiga (Ephes)
tia cautella), Cocamon seaweed (Adoxophyes orana),
Codling moth (Carpocapsa pomonella), Kaburagaga (Agr)
otis fucosa), Honey moth (Galleria mellonella), diamondback moth (Plutella maculipennis), Heliotis (Heliot)
his virsens), citrus fruit moth (Phyllocnistisocitr)
ella); Hemiptera, such as leafhoppers (Nephotettix cincticeps), brown planthoppers (Nilaparvata lugens), and brown planthoppers (Lao)
delphax striatellus), White-tailed planthopper (Sogatella furc)
ifera), scale insect (Pseudococcus comstoc)
ki), Japanese scale aphid (Unaspis yanonensis), green peach aphid (Myzus persicae), apple aphid
(Aphis pomi), cotton aphid (Aphis gossypii), red aphid (Rhopalosiphum pseudobrassica)
s), Nasi Gumbai (Stephanitis nashi), Blue bug
(Nazara spp.), Whitefly (Trial eurodes v)
aporariorum), psyllid (Psylla spp.); Orthoptera, for example, kerula (Gryllotalpa africana), grasshopper (Locustamigrat)
oria migratoriodes) etc.

The active compound mixtures according to the invention can be in the form of mixtures of the components (1) and (2) or in the form of individual formulations, which are each mixed in situ. And as such forms, solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active compound infiltration-natural and synthetic, microcapsules, seed coatings, formulations with combustion devices (For example, as a combustion device, fumigation and fumes cartridges, cans and coils), and ULV (cold mist, warm mist)
Can be mentioned.

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 fixed 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.

Liquid diluents or carriers generally include aromatic hydrocarbons (e.g., xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (e.g., chlorobenzenes, ethylene chloride, chlorides). Methylene etc.), aliphatic hydrocarbons [eg cyclohexane etc., paraffins (eg mineral oil fraction etc.)], alcohols
(E.g., butanol, glycol and their ethers, esters, etc.), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), strong polar solvents (e.g., dimethylformamide, dimethyl sulfoxide, etc.) and water. You can

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.

Examples of the solid diluent include soil natural minerals (e.g., cation, clay, talc, chalk, quartz, attapal guide, montmorillonite, or diatomaceous earth), soil synthetic minerals (e.g., highly dispersed silicon, alumina, silicates, etc.). be able to.

As a solid carrier for granules, crushed and fractionated rocks (e.g., calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic particles of inorganic and organic powders, and fine particles or organic substances ( For example, sawdust, coconut coconut, corn cob, tobacco stem and the like) can be mentioned.

Emulsifiers and / or foaming agents include nonionic and anionic emulsifiers [eg polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers
(For example, alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, etc.)] and albumin hydrolysis products.

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

Adhesives can also be used in the formulation (powder, granules, emulsions), such adhesives including carbomethylcellulose and natural and synthetic polymers (e.g. gum arabic, polyvinyl alcohol and polyvinyl acetate, etc.). be able to.

Colorants 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 phthalocyanine dyes, and also iron. , Manganese, boron, copper cobalt, molybdenum, zinc and their salts.

The formulation may generally contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight, of the active ingredient.

The active compound mixtures according to the invention are in their commercially useful formulations and in the use forms prepared according to these formulations other active compounds, for example insecticides, baits, fungicides,
It can also be present as a mixture with acaricides, nematicides, fungicides, growth regulators or herbicides. Here, examples of the insecticide include organic phosphorus agents, carboxylate agents, chlorinated 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 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 compound mixtures according to the invention in the commercially useful use forms can be varied within wide limits.

The active concentration of the active compound mixtures according to the invention is, for example, 0.00001 to 100% by weight, preferably
It is 0.001 to 1% by weight.

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

Active compounds when used as pests against stocks
Not only good stability against alkali on lime material, but also excellent residual effect on wood and soil,
Have been struck.

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 Test against brown planthopper Preparation of test solution Solvent: 3 parts by weight of xylol Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether 1 part by weight of each of the active compounds described above in order to make a suitable active compound formulation It was mixed with the above amount of solvent containing an emulsifier and the mixture was diluted with water to the specified concentration.

Test method: Plant three rice plants with a plant height of about 15 cm in a pot with a diameter of about 13 cm,
After 10 days from planting, the active compound prepared as described above was diluted with water to a predetermined concentration using a spray gun to give 2 per pot.
After spraying 0 ml of the solution and air-drying the sprayed solution, a net was placed on the pot to inoculate 10 fourth-instar larvae of the brown planthopper per pot, which were placed in a temperature-controlled room and the dead insects were counted 3 days later to calculate the insecticidal rate. still,
The test was conducted in two consecutive cycles.

The results are shown in Table 1.

3. Compounds used in the present invention: [A]: Propoxur [B]: BPMC [C]: Isoprocarbo [D]: Mettlecarb [E]: Xylylcarb [F]: Carbofuran [G]: Carbosulfuan [H]: Amino Sulfuan [I]: Bendiocarb Example 2 Test for cotton aphid Test method: About 100 cotton aphids bred per eggplant seedling planted in a pot having a diameter of 9 cm and a height of about 15 cm were inoculated per seedling, and one day after the inoculation 20 times per pot using a spray gun, a water dilution of the active compound prepared as in Example 1 at a given concentration.
After spraying, the mixture was sprayed and left in a greenhouse at 28 ° C. Two days after spraying, dead insects were counted and the mortality rate was calculated.

The results are shown in Table 2.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification number Office reference number FI technical display location A01N 47/24 H 8930-4H // (A01N 47/24 43:54) (A01N 47/24 43) : 50) (A01N 47/18 43:50) (A01N 47/22 43:50) (A01N 47/22 43:54)

Claims (1)

[Claims] 1. A 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 a nitromethylene derivative of (2) 2-isopropoxy Phenyl methylcarbamate, o-cumenyl methylcarbamate, 2-sec-butylphenyl methylcarbamate, 3,4-xylylmethylcarbamate, m-tolylmethylcarbamate, α-ethylthio-o-tolylmethylcarbamate, 2-dimethylamino-5. 6-dimethylpyrimidine-4
-Yl dimethylcarbamate, 2,2-dimethyl-1,3-benzooxol-4-yl methylcarbamate, 2,3-dihydro-2,2-dimethylbenzofuran-7
-Yl methyl carbamate, 2,3-dihydro-2,2-dimethylbenzofuran-7
-Yl- (dibutylaminothio) (methyl) carbamate and 2,3-dihydro-2,2-dimethylbenzofuran-7
-Nyl-N- (N-isopropyl-N-ethoxycarbonylethylaminosulfenyl) -N-methylcarbamate containing an active compound mixture comprising at least one carbamate selected from agricultural and horticultural insecticides. Composition.