JPH06329508A - Agricultural insecticidal composition - Google Patents

Abstract

PURPOSE:To provide a new insecticidal composition giving excellent insecticidal activity, comprising a specific nitro compound and established insecticidal compound(s) selected from seven kinds of compounds in addition to O,S-dimethyl- acetylphosphoroamidothioate. CONSTITUTION:The objective composition comprising (A) a nitro compound of the formula (Z is 2-chloro-5-pyridyl or 2-chloro-5-thiazolyl; R<1> and R<2> are each H or 1-4C alkyl) and (B) at least one kind of compound selected from O,S-dimethylacetylphosphoroamidothioate, S,S'-[2-(dimethylamino) trimethylene]bisthiocarbamate, N,N-dimethyl-1,2,3-trithiane-5-ylamine, 2- isopropoxyphenyl-methylcarbamate, 2-sec-butylphenyl-methylcarbamate, O,O- dimethyl-O-3,5,6-trichloro-2-pyridylphosphorothioate and other two kinds of compounds. This composition gives excellent synergistic effects.

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 showing an excellent insecticidal action. The nitro compound of the formula (I) used in the present invention is disclosed in Japanese Patent Application Laid-Open No.
No. 235881, which itself has an insecticidal action. 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-trithiane-5. -Ylamine, 2-
Isopropoxyphenyl methyl carbamate, 2-s
ec-Butylphenyl methyl carbamate, O, O-
Dimethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate, 2- (4-ethoxyphenyl)-
2-Methylpropyl 3-phenoxybenzyl ether and 2-tert-butylimino-3-isopropyl-
5-phenyl-3,4,5,6-tetrahydro-2H-
1,3,5-thiadiazin-4-one. [Pestay Side Manual 8th Edition 1987 (The Britis
h Crop Protection Council
Issue) description].

In recent years, in the agricultural field, it has been desired to reduce the amount of pesticides used as well as pest control agents in general. From this point, it is effective at a low dose while maintaining the efficacy. Development of drugs is desired.

The present inventors, as active compounds,
Formula (I):

[Chemical 2] In the formula, Z represents 2-chloro-5-pyridyl or 2-chloro-5-thiazolyl, and R ¹ and R ² each independently represent a hydrogen atom or C _1-4 alkyl. Nitro compounds and known insecticidal compounds O and S
-Dimethyl acetyl phosphoroamido 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,
Thiocyclam), 2-isopropoxyphenyl methyl carbamate (hereinafter abbreviated as propoxur), 2-sec-butylphenyl methyl carbamate (hereinafter abbreviated as BPMC), O, O-dimethyl O.
-3,5,6-trichloro-2-pyridyl phosphorothioate (hereinafter abbreviated as chloropyrifosmethyl), 2
-(4-Ethoxyphenyl) -2-methylpropyl 3
-Phenoxybenzyl ether (hereinafter abbreviated as etofenprox) and 2-tert-butylimino-
It was found that the novel active compound mixture containing 3-isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H-1,3,5-thiadiazin-4-one 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, the conventional insecticides have their respective insecticidal effects, but the insecticidal spectrum, the insecticidal effect (the insecticidal effect against various growth stages such as eggs, larvae, and adult worms), residual effect, fast-acting effect, penetration It does not fully satisfy various characteristics such as migration property, 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 an excellent drug is desired.

As a result of intensive studies conducted by the present inventors to solve the above-mentioned various problems, surprisingly, the active compound mixture according to the present invention in which a known insecticidal compound is mixed with the nitro compound of the above formula (I). It has been found that the insecticidal activity of the above is greater than the sum of the effects of the active compounds each alone and exerts excellent synergistic and synergistic effects. That is, by applying the insecticidal composition according to the present invention, the effect on paddy field pests, for example, planthoppers of hemiptera pests (green planthoppers, sedge loachs, etc.), etc., cooperates at a lower concentration than the case of a single active compound alone. We have found that they can be achieved both objectively and synergistically. 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- (6-chloro-3-pyridylmethyl)
-3,5-Dimethyl-2-nitroiminohexahydro-
1,3,5-triazine, 1- (6-chloro-3-pyridylmethyl) -3-methyl-2-nitroiminohexahydro-1,3,5-triazine, 1- (6-chloro-3
-Pyridylmethyl) -5-methyl-2-nitroiminohexahydro-1,3,5-triazine, 1- (6-chloro-3-pyridylmethyl) -5-isopropyl-2-nitroiminohexahydro-1, 3,5-triazine, 1
-(6-Chloro-3-pyridylmethyl) -2-nitroimino-5-propylhexahydro-1,3,5-triazine, 1- (2-chloro-5-thiazolylmethyl)-
3,5-Dimethyl-2-nitroiminohexahydro-
1,3,5-triazine, 1- (2-chloro-5-thiazolylmethyl) -3-methyl-2-nitroiminohexahydro-1,3,5-triazine, 1- (2-chloro-
5-thiazolylmethyl) -5-methyl-2-nitroiminohexahydro-1,3,5-triazine, 1- (2-
Chloro-5-thiazolylmethyl) -5-isopropyl-
2-Nitroiminohexahydro-1,3,5-triazine, 1- (2-chloro-5-thiazolylmethyl) -2-
Nitroimino-5-propylhexahydro-1,3,5
-Triazine.

The weight ratio of active compounds in the insecticidal composition can be varied within a relatively wide range. In general,
Active compounds 1 of the active compounds group of nitro compounds of formula (I)
A known insecticidal compound is used in an amount of 0.01 to 5 parts by weight, for example.
Parts by weight, preferably 0.04 to 1 part by weight are used. The insecticidal composition according to the present invention exhibits an excellent insecticidal action, and thus can be used as an insecticide by foliage application, water or water 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.
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 is particularly useful for controlling paddy field pests such as planthoppers of hemiptera pests (for example, brown planthopper, sedge planthopper, brown planthopper) and leafhoppers.

The insecticidal compositions of the present invention generally do not exclude their use against the pests exemplified below. As insects, pests of the order Coleoptera, such as adzuki bean weevil (Cal)
Losobruchus chinensis), weevil (Sitophilus zeamais),
Tribium castan
eum), Red-tailed Spodoptera (Epilac)
hna vicintioctomaculata),
Agrioles fuso (Agriotes fus)
cicollis), Rabbitfish (Anomala r)
ufocuprea, Colorado potato beetle (Le
ptinotarsa decemlineata),
Diabrotica spp.,
Pine beetle, Monochamus alt
ernatus), rice weevil (Lissorh)
optrus oryzophilus), platypus beetle (Lyctus bruneus); Lepidoptera,
For example, gypsy moth (Lymantria dispa)
r), plum bug (Malacosoma neust)
ria), Aeruginata (Pierisrapae), Spodoptera litura,
Yeast (Mamestra brassicae), Nikameichu (Chilosuppressali)
s), Awanomeiga (Pyrausta nubila)
lis), Ephedra ca
utella), Spodoptera litura (Adoxophy)
es orana), Codling moth (Carpocaps)
a pomonella, Kaburagaga (Agroti)
s fucosa), Honey hemlock (Galleria)
melonella), diamondback moth (Plutella)
maculipennis), Heliotheis (Heli)
otisvirescens), citrus fruit moth (P
hyllocnistis citrella);

Hemiptera, such as leafhopper (Ne)
potatotix cinchticeps), brown planthopper (Nilaparvata lugens),
Red-faced planthopper (Laodelphax straat)
ellus), Sedgerower (Sogatella f)
urcifera), scale insect (Pseu)
dococcus comstocki), Japanese scale insect (Unaspis yanonensis),
Green peach aphid (Myzus persica)
e), apple aphid (Aphis pomi), cotton aphid (Aphis gossypii), radish aphid (Rhopalosiphum p)
seudobrassicas, Nasigumbai (St
ephanitis nashi), green bug (N)
ezara spp. ), Whitefly Whitefly (Tri
aleurodes vapororum), psyllid (Psylla spp.);
Grasshopper (Locusta migratoria mi)
Gratoroides); etc.

The pesticidal composition of the present invention can be in the form of a binary mixture or in the form of a conventional formulation, each for in situ mixing. And as such forms, liquids, emulsions, suspensions, wettable powders, powders, foams, pastes, granules, aerosols, active compound infiltration-natural and synthetic, microcapsules, seed coatings, combustion devices (For example, as a combustion device, fumigation and fumes cartridges, cans and coils), and ULVs (cold mist, 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). , Methylene chloride, etc.), aliphatic hydrocarbons [eg, cyclohexane etc., paraffins (eg mineral oil fractions etc.)], alcohols (eg butanol, glycol and their ethers, esters etc.), ketones (eg , Acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), strong polar solvent (eg, dimethylformamide, dimethyl sulfoxide, etc.)
And we can mention 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, chalk, 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 ground and fractionated rocks (eg, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic particles of inorganic and organic powders, and fine particles or Organic substances such as sawdust, coconut cocoons, corn cobs and tobacco stems may 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. As a dispersant,
Examples include 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

It is also possible to use colorants, such as inorganic pigments (for example iron oxide, titanium oxide and Prussian blue) and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes, and In addition, trace elements can be mentioned such as salts of iron, manganese, boron, copper, cobalt, molybdenum, zinc. The preparation contains, for example, 0.1 to 9 of the active ingredient.
It may be contained in an amount of 5% by weight, preferably 0.5 to 90% by weight.

The insecticidal compositions of the present invention are commercially
Useful formulations and in the use forms prepared by these formulations, with other active compounds, such as insecticides, poison baits, fungicides, acaricides, nematicides, fungicides, growth regulators or herbicides. It can also be present as a mixture of
Here, examples of the insecticide include 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 pesticidal composition according to the invention in the commercially useful use forms can be varied within wide limits. The use concentration of the insecticidal composition of the present invention is, for example, 0.
00001 to 100% by weight, preferably 0.
001 to 1% by weight. 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- (6-chloro-3-pyridylmethyl)-
3,5-Dimethyl-2-nitroiminohexahydro-
1,3,5-triazine, No. 2: 1- (2-chloro-5-thiazolylmethyl)-
3,5-Dimethyl-2-nitroiminohexahydro-
1,3,5-triazine, No. 3: 1- (6-chloro-3-pyridylmethyl) -3
-Methyl-2-nitroiminohexahydro-1,3,5
-Triazine, No. 4: 1- (2-chloro-5-thiazolylmethyl)-
3-methyl-2-nitroiminohexahydro-1,3
5-triazine.

Known insecticidal compound A: 2-tert-butylimino-3-isopropyl-
5-phenyl-3,4,5,6-tetrahydro-2H-
1,3,5-thiadiazin-4-one B: acephate C: cartap D: thiocyclam E: BPMC F: propoxur G: chlorpyrifosmethyl H: etofenprox

[0019]

【Example】

Example 1. Test for brown planthopper Preparation of test solution Solvent: Xylol 3 parts by weight Emulsifier: Polyoxyethylene alkylphenyl ether 1 part by weight Each active compound 1 part by weight contains the above amount of emulsifier in order 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 each having a plant height of about 15 cm were planted in a pot having a diameter of about 13 cm, and 10 days after the planting, 20 ml of the active compound prepared as described above was diluted with a predetermined concentration in water using a spray gun. After air-drying the sprayed drug solution, cover the pot with a basket and place 3rd instar larvae of the brown planthopper 1 per pot.
Zero animals were inoculated, placed in a constant temperature room, and 7 days later, dead insects were counted and the insecticidal rate was calculated. In addition, the test was conducted in two consecutive systems. The results are shown in Table 1.

[0020]

[Table 1]

Example 2. Test against the brown planthopper Test method: 3 rice plants with a plant height of about 15 cm were planted in a pot with a diameter of about 13 cm, and 10 days after planting, a water diluting solution of a predetermined concentration of the active compound prepared as in Example 1 was used 1 using a spray gun. After spraying 20 ml per pot and air-drying the sprayed drug solution, a net was placed in the pot and 10 fourth-instar larvae of the brown planthopper were inoculated per pot, and placed in a thermostatic chamber, and the dead insects were counted 3 days later to calculate the insecticidal rate. In addition, the test was conducted in two consecutive systems. The results are shown in Table 2.

[0022]

[Table 2]

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Claims (3)

[Claims] 1. An active compound of the formula (I): In the formula, Z represents 2-chloro-5-pyridyl or 2-chloro-5-thiazolyl, and R ¹ and R ² each independently represent a hydrogen atom or C _1-4 alkyl. Nitro 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, O, O-dimethyl O-3,5,6-trichloro-2-
Pyridyl phosphorothioate, 2- (4-ethoxyphenyl) -2-methylpropyl
3-phenoxybenzyl ether and 2-tert-butylimino-3-isopropyl-5-phenyl-3,
An insecticidal composition containing at least one selected from the group consisting of 4,5,6-tetrahydro-2H-1,3,5-thiadiazin-4-one. 2. The insecticidal composition according to claim 1, wherein the nitro compound, Z in formula (I) is 2-chloro-5-pyridyl, and R ¹ and R ² are methyl. 3. An insecticidal composition according to claim 1, wherein the nitro compound, Z in formula (I) is 2-chloro-5-thiazolyl, and R ¹ and R ² are methyl.