JPH0791164B2 - Agricultural and horticultural insecticide composition - Google Patents

Description

The present invention relates to a novel combination of agricultural and horticultural active substances having an excellent insecticidal action between an imino-substituted heterocyclic compound of formula (I) described below and known carbamates.

The imino-substituted heterocyclic compounds of formula (I) used in the present invention and their use as insecticides are disclosed in JP-A-61-267575 (Japanese Patent Application No. 60-106854) and JP-A-62-81382 ( Japanese Patent Application Sho6
0-219082) and JP-A-62-207266 (Japanese Patent Application No. 61-486).
No. 29) described in the specification.

It has already been described that the following carbamates have insecticidal activity. For example, 2-iso-propoxyphenyl methyl carbamate, 2-sec-butylphenyl methyl carbamate, o-cumenyl methyl carbamate, etc. [See, for example, Pestayside Manual (7th Edition, 1983 The British Crop Protection Coun
cil issued)].

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.

According to the present inventors, (1) General formula In the formula, X represents S, CH ₂ or N—R ² (in the formula, R ² represents a hydrogen atom or an alkylcarbonyl group having 1 to 3 carbon atoms of an alkyl group), R ¹ represents a chloro atom or bromine. Represents a pyridyl group substituted with one or two selected from an atom, a fluoro atom or a methyl group, a chloro atom, a fluoro atom, a bromine atom or a thiazolyl substituted with a methyl group, and the bonding position of the pyridine ring is 3- Position (or 5-position), the bonding position of the thiazole ring is the 5-position, m represents 2 or 3, and Z represents NO ₂ or CN. ) General formula In the formula, R ¹ is the same or different and has 1 or 2 carbon atoms of 1 to 4
Represents an alkyl group, an alkoxy group having 1 to 4 carbon atoms, a phenyl group substituted with an ethylthiomethyl group, or R ¹ is a naphthyl group, a dialkylamino group having 1 to 3 carbon atoms, preferably a dimethylamino group, And a pyrimidyl group substituted with two alkyl groups having 1 to 4 carbon atoms, preferably a methyl group, or 2,3-substituted with an alkyl group having 1 to 4 carbon atoms, preferably a methyl group.
R ² represents a dihydrobenzofuranyl group or a benzodioxolyl group, R ² represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, preferably a hydrogen atom or a methyl group, and R ³ represents 1 to 4 carbon atoms. An alkyl group, preferably a methyl group, or (Wherein R ⁴ represents an alkyl group having 1 to 5 carbon atoms, R ⁵ represents an alkyl group having 1 to 5 carbon atoms, and
It has been found that a novel active substance combination containing, as an active ingredient, at least one compound selected from the carbamates represented by (representing an alkoxycarbonyl group or an alkoxycarbonylalkyl group), exhibits 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.

Furthermore, as a result of repeated use of conventional drugs, various pests that have acquired resistance to various drugs 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. 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 vegetables, flowers 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 abilities of stored grain pests and various other pests.

As a result of earnest studies to solve the above-mentioned various problems, the present inventors have surprisingly found that the carbamate represented by the formula (II) known to the imino-substituted heterocyclic compound represented by the formula (1) is known. It has been discovered that the insecticidal activity of the active compound mixtures according to the invention which are formulated with a class of compounds is greater than the sum of the effects of the active compounds each alone, and exerts excellent cooperation and synergism.

That is, by applying the insecticidal composition according to the present invention,
For example, effects on paddy field pests, such as hemiptera pests planthoppers (eg, brown planthoppers) and vegetable pests, such as hemiptera pest aphids, are cooperative and synergistic at lower concentrations than with only one active compound. 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 an extremely outstanding technological progress in industrial utility.

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

In the formula, X represents S, CH ₂ or N—R ² (in the formula, R ² represents a hydrogen atom or an alkylcarbonyl group having 1 to 3 carbon atoms of an alkyl group), R ¹ represents a chloro atom or bromine. Represents a pyridyl group substituted with one or two selected from an atom, a fluoro atom or a methyl group, a chloro atom, a fluoro atom, a bromine atom or a thiazolyl group substituted with a methyl group, and the bonding position of the pyridine ring is 3 -Position (or 5-position), the bonding position of the thiazole ring is 5-position, m represents 2 or 3, and Z represents NO ₂ or CN.

Examples of imino-substituted heterocyclic compounds of general formula (I) for use in the active substance combinations according to the invention include the following compounds: 1- (3-pyridylmethyl) -2- (nitroimino) imidazo Lysine, 1- (2-chloro-5-pyridylmethyl) -2- (nitroimino) imidazolidine, 1- (2-chloro-5-pyridylmethyl) -2- (nitroimino) tetrahydropyrimidine, 1- (2-fluoro -5-pyridylmethyl) -2- (nitroimino) imidazolidine, 1- (2-fluoro-5-pyridylmethyl) -2- (nitroimino) tetrahydropyrimidine, 1- (2-bromo-5-pyridylmethyl) -2 -(Nitroimino) imidazolidine, 1- (2,3-dichloro-5-pyridylmethyl) -2-
(Nitroimino) imidazolidine, 1- (2-methyl-5-pyridylmethyl) -2- (nitroimino) imidazolidine, 1- (2-methyl-5-pyridylmethyl) -2- (nitroimino) tetrahydropyrimidine, 1- (2-chloro-5-thiazolylmethyl) -2- (nitroimino) imidazolidine, 1- (2-chloro-5-thiazolylmethyl) -2- (nitroimino) tetrahydropyrimidine, 1- (2-fluoro-5-thiazolylmethyl)- 2-
(Nitroimino) imidazolidine, 1- (2-methyl-5-thiazolylmethyl) -2- (nitroimino) imidazolidine, 1- (2-methyl-5-thiazolylmethyl) -2- (nitroimino) tetrahydropyrimidine, 1-acetyl- 3- (2-chloro-5-pyridylmethyl) -2- (nitroimino) imidazolidine, 1-acetyl-3- (2-chloro-5-pyridylmethyl) -2- (nitroimino) tetrahydropyrimidine, 1-butyryl- 3- (2-chloro-4-fluoro-5-
Pyridylmethyl) -2- (nitroimino) imidazolidine, 3- (2-chloro-5-pyridylmethyl) -2- (nitroimino) thiazolidine, 3- (2-chloro-5-pyridylmethyl) -2- (nitroimino) Tetrahydro-2H-1,3-thiazine, 3- (2-fluoro-5-pyridylmethyl) -2- (nitroimino) thiazolidine, 1- (2-chloro-5-pyridylmethyl) -2- (nitroimino) pyrrolidine, 1- (2-chloro-5-pyridylmethyl) -2- (nitroimino) piperidine, 1- (2-bromo-5-pyridylmethyl) -2- (nitroimino) pyrrolidine, 1- (2-fluoro-5-pyridyl Methyl) -2- (nitroimino) pyrrolidine, 1- (2-chloro-5-pyridylmethyl) -2- (cyanoimino) iridazolidine, 1- (2-chloro-5-pyridylmethyl) -2- (cyanoimino) 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-2H-1, 3-thiazine, 1- (2-fluoro-5-pyridylmethyl) -2- (cyanoimino) thiazolidine, 1- (2-chloro-5-thiazolylmethyl) -2- (cyanoimino) thiazolidine, 1- (2-chloro- 5-thiazolylmethyl) -2- (cyanoimino) tetrahydro-2H-1,3-thiazine.

The carbamates used in the active substance combinations according to the invention have the general formula In the formula, R ¹ is the same or different and has 1 or 2 carbon atoms of 1 to 4
Represents an alkyl group, an alkoxy group having 1 to 4 carbon atoms, a phenyl group substituted with an ethylthiomethyl group, or R ¹ is a naphthyl group, a dialkylamino group having 1 to 3 carbon atoms, preferably a dimethylamino group, And a pyrimidyl group substituted with two alkyl groups having 1 to 4 carbon atoms, preferably a methyl group, or 2,3-substituted with an alkyl group having 1 to 4 carbon atoms, preferably a methyl group.
R ² represents a dihydrobenzofuranyl group or a benzodioxolyl group, R ² represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, preferably a hydrogen atom or a methyl group, and R ³ represents 1 to 4 carbon atoms. An alkyl group, preferably a methyl group, or (Wherein R ⁴ represents an alkyl group having 1 to 5 carbon atoms, R ⁵ represents an alkyl group having 1 to 5 carbon atoms, and
Represents an alkoxycarbonyl group or an alkoxycarbonialkyl group).

Examples of the carbamates of the general formula (II) include the following compounds: 2-iso-propoxyphenyl methylcarbamate (propoxur propoxur), o-cumenyl methylcarbamate (isoprocarb)
isoprocarb), 2-sec-butylphenyl methyl carbamate (BPM
C), 3,4-xylyl methyl carbamate (xylylcarb
xylylcarb), m-tolyl methyl carbamate (metholcarb meto)
lcarb), 3,5-xylyl methyl carbamate (XMC), α-ethylthio-o-tolyl methyl carbamate (ethiophenecarb ethiofencarb), 1-naphthyl methyl carbamate (carbaryl carb)
aryl), 2-dimethylamino-5,6-dimethylpyrimidine-4-
Il dimethyl carbamate (pirimica pirimica
rb), 2,2-dimethyl-1,3-benzodioxol-4-yl
Methyl carbamate (benziocarb bendiocarb), 2,3-dihydro-2,2-dimethylbenzofuran-7-yl methyl carbamate (carbofuran carbofuran), butyl 2,3-dihydro-2,2-dimethylbenzofuran-
7-yl N, N-dimethyl-N, N-thiodicarbamate (furanthiocarb furathiocarb), 2,3-dihydro-2,2-dimethylbenzofuran-7-yl (dibutylaminosulfenyl) (methyl) carbamate (Carbosulfan carbosulfan), 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N- (N-isopropyl-N-ethoxycarbonylethylaminosulfenyl) -N-methylcarbamate (aminosulfuran aminosulfulan) ), S-methyl N- (methylcarbamoyloxy) thioacetimidate (methomyl methomyl).

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

The weight ratio of active compounds of each group in the active substance combination can be varied within a relatively wide range. In general,
(1) per part by weight of active compound of the active compound group of the imino-substituted heterocyclic compound of general formula (I), (2) general formula (I
The active compound of the active compound group of the carbamate of I),
For example, 0.1 to 20 parts by weight, preferably 0.2 to 15 parts by weight can be used.

The active substance combinations according to the invention show an excellent insecticidal activity. Therefore, the active substance combination 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 active substance combinations 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 for susceptible and resistant species, and all or some stages of development.

For example, the insecticidal composition of the present invention is particularly useful for planthoppers of hemiptera pests (for example, brown planthopper, scorpion planthopper, brown planthopper), leafhoppers, etc., paddy field pests such as rice leaf weevil and rice leaf weevil, and aphids of hemiptera pests It can be effectively used for controlling pests of garden crops such as fruit trees and vegetables.

Examples of the above-mentioned pests include the following. Examples of such pests include the following pests.

Coleoptera pests, such as the weevil Weevils (Callosobru
chus chinensis), weevil (Sitophilus zeama)
is), Tribolium castaneum, and Epilachnavigintioctomacula
ta), Red-breasted beetle (Agriotes fuscicol)
lis), Japanese beetle (Anomala rufocuprea), Colorado potato beetle (Leptinotarsa decemkineata), diabrotica (Diabrotica spp.), pine wilt beetle (Monochamus alternatus), rice weevil (Li)
ssorhoptrus oryzophilus), rice weevil (Echinoci)
nemus squameus), rice leaf beetle (Oulema ory)
zae), flat beetle (Lyctus brunneus); Lepidoptera, for example, gypsy moth (Lymantria dispar), plum bug (Malac)
osoma neustria), caterpillar (Pierisrapae), Spodoptera litura (Spodoptera litura), Spodoptera litura (Mamestra)
brassicae), Nikameichiyu (Chilo suppressali
s), Kobuno-maiga (Cnaphalocrocis medinalis), Phellinus terrestris (Naranga aenescens), Awanomeiga (Pyrausta nubilalis), Koyamamadamaiga (Ephesti)
a cautella), Japanese cabbage (Adoxophyes oran)
a), Codling moth (Carpocapsa pomonella), Kaburagaga (Agrotis fucosa), Honey moth (Galleria mello)
nella), diamondback moth (Plutella maculipennis), Heliothis virescens, orange citrus moth (Phyllocnistis citrella)
nara guttata); Hemiptera, such as leafhopper (Nephotettix cincticeps), brown planthopper (Nilap)
arvata lugens), Greater Planthopper (Laodelphax stri)
atellus), sedge loach (Sogatella furcifera),
Pseudococcus comstocki,
Green aphid (Unaspis yanonensis), green peach aphid (Myzus persicae), apple aphid (Aphis pomi), cotton aphid (Aphis gossypi)
i), Rhopalosiphum pseudo
brassicas), Nasi Gumbai (Stephanitis nashi),
Blue bug (Nezara spp.), Whitefly (Trialeurodes vaporariorum), White lice (Psylla)
spp.); Orthoptera, for example, kerula (Gryllotalpa africana), locust (Locusta mi)
gratoria 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, 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 fumigation cartridges, cans and coils), and ULV [cold mist, warm mist (warm mist)
st)].

These preparations can be manufactured by a known method. Such a process comprises, for example, applying the active compound to a spreading agent, ie a liquid diluent; an oxidizing gas diluent; a solid diluent or a carrier, optionally a surfactant, ie an emulsifier and / or dispersant and / or Alternatively, 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). Methylenes), aliphatic hydrocarbons [eg, cyclohexane, paraffins (eg, mineral oil fractions)], 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 ground and fractionated rocks (eg, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic particles of inorganic and organic powders, and fine particles of organic material (eg, , Sawdust, coconut coconut, corn cob and tobacco stem).

Examples of the emulsifier and / or foaming agent include nonionic and anionic emulsifiers [eg, polyoxyethylene fatty acid ester acid, 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 carboxymethylcellulose and natural and synthetic polymers (eg gum arabic, polyvinyl alcohol and polyvinyl acetates). You can

It is also possible to use colorants, which include 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 also iron , Manganese, boron, copper, cobalt, molybdenum, zinc and their salts.

The formulation generally comprises from 0.1 to 95% by weight of the active ingredient,
Preferably 0.5 to 90% by weight can be contained.

The active substance combinations 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, carboxylate agents, chlorinated hydrocarbon agents, and insecticidal substances produced by microorganisms.

Furthermore, the active substance combinations 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 use concentration of the active compound of the present invention can be appropriately selected and changed, but is, for example, 0.00001 to 100% by weight, preferably 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 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 brown planthopper Preparation of test solution Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether In order to make a suitable active compound formulation, the test is shown in Table 1 below. 1 part by weight of the active compound mixture or active compound alone indicated in the drug column was mixed with the above amount of solvent containing the above amount of emulsifier and the mixture was diluted with water to the given concentration.

Test method: Planting 3 rice plants with a plant height of about 15 cm in a pot with a diameter of 13 cm.
After 10 days, spray 20 ml of a diluted solution of the active compound prepared as above at a predetermined concentration with a spray gun, air-dry the sprayed drug solution, cover the pot with a net basket, and carbamate-resistant brown planthopper 4th instar larvae. 10 animals were inoculated per pot and placed in a thermostatic chamber, and 3 days later, the number of dead insects was counted and the insecticidal rate was calculated. In addition, the test was conducted in two consecutive systems. The results are shown in Table 1.

Note) 1. No phytotoxicity is observed in any of the mixtures and single agents used in the test of Example 1.

2. Compounds of general formula (I) used in the present invention: Compound No. 1 1- (2-chloro-5-pyridylmethyl) -2- (nitroimino) imidazolidine, Compound No. 2 1- (2-chloro -5-pyridylmethyl) -2- (nitroimino) tetrahydropyrimidine, compound No.3 1- (2-chloro-5-thiazolylmethyl) -2- (nitroimino) imidazolidine compound No.4 1-acetyl-3- (2 -Chloro-5-pyridylmethyl) -2- (nitroimino) imidazolidine Compound No. 5 3- (2-chloro-5-pyridylmethyl) -2- (nitroimino) thiazolidine, Compound No. 6 1- (2-chloro -5-pyridylmethyl) -2- (nitroimino) piperidine, compound No. 7 1- (2-chloro-5-pyridylmethyl) -2- (cyanoimino) imidazolidine compound No. 8 1 (2-Methyl-5-pyridylmethyl) -2- (nitroimino) imidazolidine Compound No. 9 1- (2-methyl-5-thiazolylmethyl) -2- (nitroimino) imidazolidine 3. Compound used in the present invention: [A]: Propoxur [B]: BPMC [C]: Isoprocarbo [D]: Metolcarb [E]: Xylylcarb [F]: Carbofuran [G]: Carbosulfan [H]: Aminosulfur [I]: Bendiocarb Example 2 Test against cotton aphid Test method: About 100 cotton aphids bred to eggplant seedlings 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, Table 2 below, Example 1 except that the active compound mixture or the active compound alone shown in the column of reagent agent is used.
Spray 20 ml of a diluted solution of the active compound prepared in the above-mentioned manner with a spray gun, and after spraying 28
The sample was left in a greenhouse at 0 ° C., and two days after the application, dead insects were counted and the insecticidal rate was calculated.

The results are shown in Table 2.

Note) 1. No phytotoxicity is observed in any of the mixtures and single agents used in the test of Example 2.

2. Compounds of general formula (I) used in the present invention: No. 1, No. 2, N
o.3, No.4, No.5, No.6, No7, No8 and No.9 represent the same compounds as in Example 1.

3. Compounds used in the present invention: [J]: ethiofenecarb [K]: pirimicarb Example (wettable powder) 20 parts of active compound of formula (I), 20 parts of active compound propoxur of formula (II), powder 55 parts of a mixture (1: 5) of diatomaceous earth and powdered clay, 2 parts of sodium alkylbenzenesulfonate and 3 parts of sodium alkylnaphthalenesulfonate formalin condensate are ground and mixed to obtain a wettable powder.

Example (Dust) 1 part active compound of formula (I), active compound BPMC of formula (II)
1 part and 98 parts of powdered clay are pulverized and mixed to obtain a powder.

Example (Granule) 96 parts of a clay mineral having a particle size distribution of 0.2 to 2 mm was placed in a rotary mixer and, under rotation, 2 parts of the active compound of the formula (I) and the compound of the formula (II) were dissolved in an organic solvent. 2 parts of the active compound propoxur is sprayed to make it even and then dried at 40 to 50 ° C to give granules.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Office reference number FI technical display location A01N 47:10) (A01N 43/50 Q 47:22) (A01N 43/40 47:10) ( (A01N 43/40 47:24) (A01N 43/40 47:22) (A01N 43/54 F 47:10) (A01N 43/54 F 47:22) (A01N 43/54 F 47:24) (A01N 43 / 78 F 47:10) (A01N 43/78 F 47:22)

Claims (1)

[Claims] 1. A general formula: In the formula, X represents S, CH ₂ or N—R ² (in the formula, R ² represents a hydrogen atom or an alkylcarbonyl group having 1 to 3 carbon atoms of an alkyl group), R ¹ represents a chloro atom or bromine. Represents a pyridyl group substituted with one or two selected from an atom, a fluoro atom or a methyl group, a chloro atom, a fluoro atom, a bromine atom or a thiazolyl group substituted with a methyl group, and the bonding position of the pyridine ring is 3 The -position (or the 5-position), the bonding position of the thiazole ring is the 5-position, m represents 2 or 3, and Z represents NO ₂ or CN; 2) General formula In the formula, R ¹ is the same or different and has 1 or 2 carbon atoms of 1 to 4
Represents an alkyl group, an alkoxy group having 1 to 4 carbon atoms, a phenyl group substituted with an ethylthiomethyl group, or R ¹ is a naphthyl group, a dialkylamino group having 1 to 3 carbon atoms, preferably a dimethylamino group, And a pyrimidyl group substituted with two alkyl groups having 1 to 4 carbon atoms, preferably a methyl group, or 2,3-substituted with an alkyl group having 1 to 4 carbon atoms, preferably a methyl group.
R ² represents a dihydrobenzofuranyl group or a benzodioxolyl group, R ² represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, preferably a hydrogen atom or a methyl group, and R ³ represents 1 to 4 carbon atoms. An alkyl group, preferably a methyl group, or (Wherein R ⁴ represents an alkyl group having 1 to 5 carbon atoms, R ⁵ represents an alkyl group having 1 to 5 carbon atoms, and
An alkoxycarbonyl group or an alkoxycarbonylalkyl group), and an active substance combination comprising at least one compound selected from the carbamates represented by: