JPH0643283B2 - Agro-horticultural insecticidal composition - Google Patents

Description

The present invention relates to a novel agricultural and horticultural active compound mixture of a nitromethylene derivative and a known insecticide, which has a superior insecticidal action.

It has been found by the present applicant that the nitromethylene derivative has 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 has already been described that the insecticides below have insecticidal activity. For example, S, S′-2-dimethylaminotrimethylene bis (thiocarbamate), 2-tert-butylimino-3-iso-propyl-5-phenyl-1,
3,5-thiadiazin-4-one, N- (2,6-difluorobenzoyl) -N '-[3,5-dichloro-4
-(3-chloro-5-trifluoromethyl-2-pyridyloxy) phenyl] urea and the like.

However, the action of these known insecticidal compounds is not always satisfactory, especially when the concentration of the active compound is low and when only small amounts are applied.

(1) General formula In the formula, X represents a lower alkyl group, a lower alkoxy group or a halogen atom, represents 0, 1 or 2, and m represents 2 or 3, and a nitromethylene derivative of (2) S, S'-2 -Dimethylaminotrimethylene bis (thiocarbamate), N, N-dimethyl-1,2,3
-Trithian-5-ylamine, 2-tert-butylimino-3-iso-propyl-5-phenyl-1,
3,5-thiadiazin-4-one, 1- (4-chlorophenyl) -3- (2,6-difluorobenzoyl) urea, N- (2,6-difluorobenzoyl) -N'-
[3,5-Dichloro-4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenyl] urea and 3-phenoxybenzyl 2- (4-ethoxyphenyl) -2-methylpropyl ether It has been found that the novel active compound mixtures which consist of at least one selected from the group consisting of the following exhibit 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 of the hemiptera, which have acquired resistance to organophosphorus insecticides and carbamate insecticides (e.g., leafhopper leafhoppers), have recently emerged in paddy fields of various regions including Japan's southwestern warm regions, It is becoming difficult to control them, and development of an excellent drug 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, rice transplantation in Japan has mainly been carried out by mechanical transplantation using 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,
In recent years, it has been desired to develop an excellent drug against harmful insects such as rice weevil.

Therefore, important pests of food crops including rice and other cereals and pests of garden crops such as vegetables, flowers and fruit trees, birch,
Pests of industrial crops such as cotton and tea, forest pests, and pests of horticultural crops in some of these, 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 insecticidal activity of the active compound mixture according to the present invention containing the known insecticide in the nitromethylene derivative is independent. It has been discovered that it exerts greater cooperation and synergism, which is greater than the sum of the effects of the active compounds, and has a residual effect.

That is, by applying the insecticidal composition according to the present invention,
For example, paddy field pests, for example, planthoppers of hemiptera pests (for example, sedge loach), lepidopteran larvae of Kobunomeiga and fruit trees, horticultural crop pests such as vegetable, for example, lepidopteran larvae of Plutella xylostella are the only active compounds. It was found that it can be achieved synergistically and synergistically at a lower concentration than in the case and has a residual effect.

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

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

In the formula, X represents a lower alkyl group, a lower alkoxy group or a halogen atom, represents 0, 1 or 2, and represents 2 or 3 respectively.
Represents

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 chloro atom, a bromine atom or a fluoro atom, represents 1 or 2, m represents 2 or 3, and a bond of the pyridine ring. The position is 3-position (or 5-position).

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

Examples of nitromethylene derivatives of the general formula (I) used in the active compound mixtures according to the invention are 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-fluoro-5-pyridylmethyl) -2- (nitromethyle ) 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-acetic acid cupric salt, 1- (2-bromo-5-pyridylmethyl) -2- (nitromethylene) imidazolidine-succinate, 1- (2,4-dichloro-5) -Pyridylmethyl) -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)].

One of the insecticides used in the active compound mixtures according to the invention is the following compound: S, S'-2-dimethylaminotrimethylene bis (thiocarbamate) (cartap cartap), N, N-dimethyl. -1,2,3-Trithian-5-ylamine (thiocyclam), 2-tert-butylimino-3-iso-propyl-5-phenyl-1,3,5-thiadiazin-4-one (buprofezin), 1 -(4-Chlorophenyl) -3- (2,6-difluorobenzoyl) urea (diflubenzuron diflubenzuro
n), N- (2,6-difluorobenzoyl) -N '-[3,
5-dichloro-4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phanyl] urea, 3-phenoxybenzyl 2- (4-ethoxyphenyl)
-2-Methylpropyl ether.

The above insecticides which are one component of the active compound mixtures according to the invention are already known. That is, for example, The Pesticide Manual, 7th edition 1983.
It is already described and known as an insecticide in the year (published by The British Crop Protection Council).

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,
(1) Per 1 part by weight of active compounds of the active compound group of the nitromethylene derivative of the general formula (I), (2) active compounds of the active compound group of known insecticides, for example 0.05 to 10 parts by weight, preferably 0.
1-5 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 low toxicity to warm-blooded animals, and accurately controls pests, particularly insects in the protection of agriculture, forestry, stored crops and products. Can be used for 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. Of genus and lepidopteran larvae of the diamondback moth, Weevil,
It can be effectively used for the control of fruit trees such as leafworms such as leaf beetles and scale insects of hemiptera, and horticultural crops such as vegetables.

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

Examples of insects include Coleoptera pests such as adzuki bean weevil (Callosobruchus chinensis), weevil (Sitophilus zeamais), and stag beetle (T
ribolium castaneum), Yellow-tailed Spodoptera (Epil)
achnavigintioctomaculata), Red-spotted beetle (Agriotes fuscicollis), Red beetle (Anomala ru)
focuprea), Colorado potato beetle (Leptinotarsa d
ecemkineata), Diablotheca (Diabrotica spp.),
Pine beetle (Monochamus alternatus), rice weevil (Lissorhoptrus oryzophilus), flat beetle (Lyctus bruneus); Lepidoptera, for example, Lymantria dispar, Malaco
soma neustria), Aphid beetle (Pieris rapae), Spodoptera litura (Spodo ptera litura), Spodoptera litura (Mamestra b)
rassicae), Nikameichiyu (Chilo suppressalis),
Pyrausta nubilalis, Ephestia cautella, Adoxoph
yes orana), Codling moth (Carpocapsa pomonella),
Cabbage moth (Agrotis fucosa), Honey moth (Galleria)
mellonella), diamondback moth (Plutella maculipennis), Heliothis virescens, citrus fruit moth (Phyllocnistis citrella);
odelphax striatellus), White-faced planthopper (Sogatella fu)
rcifera), scale insect (Pseudococcus coms)
tocki), the scale insect (Unaspis yanonensi)
s), green peach aphid (Myzus persicae), apple aphid (Aphis pomi), cotton aphid (Aphis go)
ssypii), Japanese radish aphid (Rhopalosiphum ps)
eudobrassicas), Nasigumbai (Stephanitis nash)
i), blue bug (Nazara spp.), whitefly (Trialeurodes vaporariorum), white lice (Psylla)
spp.); Orthoptera, for example, kerula (Gryllotalpa africana), locust (Locusta migr)
atoria 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 for in situ mixing. And as such a form,
Liquids, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active compound infiltrations-natural and synthetic, microcapsules, seed coatings, formulations with a combustion device (e.g. as a combustion device, Fumigation and fumigation cartridges, cans and coils, and ULVs [cold mist, warm mist (warm mis
t)].

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 And / or by using a foam forming agent and mixing. 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 (eg, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg, chlorobenzenes, ethylene chloride, chlorides). 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 room temperature and atmospheric pressure, examples of which include aerosol propellants such as butane, propane, nitrogen gas, carbon dioxide, and 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 (eg, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic particles of inorganic and organic powders, and fine particles or organic materials ( For example, sawdust, coconut coconut, corn cob, tobacco stem and the like) 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 sulfite waste liquor 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

Colorants can also be used, such as inorganic pigments (e.g. iron oxide, titanium oxide and bursian blue) and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes, and also Mention may be made of trace elements such as salts of iron, manganese, boron, copper, cobalt, molybdenum, zinc.

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, such as insecticides, baits, fungicides,
It can also be present as a mixture with acaricides, centrifuges, fungicides, growth regulators or herbicides. Here, examples of the insecticide include organic phosphorus agents, carbamate 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 working concentration of the active compound mixtures according to the invention is, for example, 0.
00001 to 100% by weight, preferably 0.0004 to
It is 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 to alkali on lime material, but also excellent residual effect in 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 Cobb Nougai 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 active compound in order to make a suitable active compound formulation Was mixed with the above-mentioned amount of the solvent containing, and the mixture was diluted with water to a predetermined concentration.

Test method: 3 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, a water diluting solution of a predetermined concentration of the active compound prepared as described above was used at 20 m per pot using a spray gun. After spraying and air-drying the spray solution, cover it with a plastic mesh cylinder with a diameter of 9 cm and a height of 25 cm, inoculate 10 4th instar larvae of Cobb Nomeiga per pot, and place in a temperature-controlled room 2
The dead insect was taught after a day and the insecticidal rate was calculated. The test was carried out in two consecutive systems.

The results are shown in Table 1.

3. Compounds used in the present invention: [A]: Cartap [B]: Thiocycrum Example 2 Test for Sedylon Plant Test method: 3 rice plants with a plant height of about 15 cm are planted in a pot with a diameter of about 13 cm.
Ten days after planting, a water dilution of the active compound prepared in the same manner as in Example 1 at a predetermined concentration was sprayed with a spray gun at 20 m per pot. 10 days after spraying, 20 days later, nets were laid on the pots, and 3rd-instar larvae of the white-necked planthopper were sown per 10
Heads were inoculated and placed in a temperature-controlled room, and after 2 and 7 days, dead insects were counted and the insecticidal rate was calculated. The test was carried out in two consecutive systems.

The results are shown in Table 2.

Example 3 Test against diamondback moth Test method: A non-heading cabbage seedling with a height of about 15 cm planted in a pot having 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 a concentration of 1 20m per spot
After spraying, the sprayed solution was air-dried, 10 second-instar larvae of Plutella xylostella were inoculated per pot, placed in a thermostatic chamber, and after 2 and 7 days, the number of dead was counted and the insecticidal rate was calculated. The test was carried out in two consecutive systems.

The results are shown in Table 3.

Example 4 Test against diamondback moth Test method: A non-heading cabbage seedling with a height of about 15 cm planted in a pot having a diameter of 9 cm was prepared by spraying a water-diluted solution of the active compound prepared as in Example 1 at a predetermined concentration with a spray gun. 20m per spot
After spraying, the sprayed drug solution was air-dried, and 10 spots of 4th-instar larvae of the Plutella xylostella var. The test is 2
I went on a continuous basis.

The results are shown in Table 4.

Continuation of the front page (51) Int.Cl. ⁵ Identification number Office reference number FI technical display location A01N 47/12 B 9159-4H 47/34 C 9159-4H

Claims (1)

[Claims] (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 a nitromethylene derivative of (2) S, S'- 2-dimethylaminotrimethylene bis (thiocarbamate), N, N-dimethyl-1,2,
3-trithian-5-ylamine, 2-tert-butylimino-3-iso-propyl-5-phenyl-1,
3,5-thiadiazin-4-one, 1- (4-chlorophenyl) -3- (2,6-difluorobenzoyl) urea, N- (2,6-difluorobenzoyl) -N'-
[3,5-Dichloro-4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenyl] urea and 3-phenoxybenzyl 2- (4-ethoxyphenyl) -2-methylpropyl ether An agricultural and horticultural insecticidal composition comprising an active compound mixture consisting of at least one selected from the group consisting of: