JPS6345206A - Agricultural and horticultural insecticidal composition - Google Patents

Abstract

PURPOSE:To obtain the titled composition, by using a specific nitromethylene derivative and well-known insecticide in combination, capable of exhibiting improved cooperative and synergistic effect and controlling even resistant insect pests in a small amount of chemical and having residual effect property. CONSTITUTION:An agricultural and horticultural insecticidal composition obtained by using (A) a compound expressed by the formula (X is halogen, alkyl or alkoxy; n is 0-2; m is 2 or 3), e.g. 3-(3-pyridylmethyl)-2-(nitromethylene) thiazolidione, and (B) an active substance selected from 11 well-known insecticides, e.g. (B1) S,S'-2-dimethylaminotrimethylene bis(thiocarbamate), (B2) N,N-dimethyl-1,2,3-trithian-5-ylamine, (B3) 1-(4-chlorphenyl)-3-(2,6-difluorobenzoyl) urea, (B4) 3-phenoxybenzyl 2-(4-ethoxyphenyl)-2-methylpropyl ether, etc., in combination. The amount of the component (B) is 0.05-10pts.wt., preferably 0.1-5pts. wt. based on 1pt.wt. component (A).

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel agricultural/horticultural active substance combination having an excellent insecticidal effect of a nitromethylene derivative of the formula (I) below and a known insecticide.

The nitromethylene derivative of the formula (R) used in the present invention is a compound that has not been described in any prior US literature. No. 18627 and Machiko Sho 60-1862
It is disclosed in Specification No. 8.

In addition, it has already been described that the following insecticides have insecticidal activity.
-butylimino-5-iso-propyl-5-phenyl-1,3,5-thiacyacyinan-4-one, N-(2,
6-difluorobenzoyl)-N'-[3,5-7chloro4-(3-chloro-5-trifluoromethyl-2
-pyrinoloxy) phenyl 1 urea, etc. [For example, see Bestayside Manual (7th edition 1983 T
heBritish Crop Protect
tion Council 1) 1. While thinking,
The effects of these known insecticidal compounds are not always satisfactory, especially when the concentration of the active compound is low or when only a small amount is applied. represents an alkyl group or an alkoxy group, n represents 0.1 or 2, and n represents 2 or 3; thiocarpanote), N,N-trimethyl-1,
2,3-) lithium 7-5-ylamine, 2-tert
-butylimino-5-iso-propyl-5-phenyl-1,3,5-thiacyanonan-4-one, 1-(4-
chlorophenyl)-3-(2,6-difluorobenzoyl)urea, N-(2,G-difluorobenzoyl)-
N'-[3+5-ychloro-4-(5-chloro-5-
Trifluoromethyl-2-pyridyloxy)phenyl 1
Urea, 3-phenoxybenzyl 2-(4-ethododiphenyl)-2-methylpropyl ether, 1-(4-
17fluoromethoxyphenyl)-3-(2-chlorobenzoyl)flare, 1-(4-(2-dichloro-1-
nofluoroethoxy)-phenyl)-3-(2-chlorobenzoyl)urea, 1-(4-)lifluorophenyl)-3-(2,6-difluorobenzoyl)flare,
1-(2,4-difluoro-3,5-nochlorophenyl)-3-(2,8-difluorobenzoyl)urea,
and N-[6-(2,2,3-)lifluoro-3-chloro-benzodioxin-(1,4))]-N'-2,
It has been found that a novel active substance combination containing as an active ingredient at least one compound selected from the group consisting of (6-difluorobenzoyl) urea exhibits excellent insecticidal activity.

Conventionally, various insecticides have been developed as insecticides for mourning gardening, and have been used as single agents or mixtures. Especially with M1
Seven-type insecticides and carbamate-based insecticides are mainly used, and later pyrethroid-based insecticides have been used. However, although each of the conventional insecticides has a certain type of insecticidal effect, the insecticidal spectrum, insecticidal effect (insecticidal effect on various insect stages, such as eggs, larvae, and adult insects), residual effect, They do not fully satisfy various properties such as fast-acting, systemic transferability, low toxicity to fish and warm-blooded animals, reduced environmental pollution, and reduced number of applications and amount of the applied drug.

Furthermore, as a result of the reverse use of conventional drugs, various insect pests that have acquired resistance to various insect pests have appeared. In particular, in recent years, planthoppers and leafhoppers (e.g., leafhoppers), which are hemipolar pests, have acquired resistance to phosphorus-based and carbamate-based insecticides in rice fields across the warm southwest region of Japan. have appeared, and it is becoming difficult to control them, so there is a desire to develop a drug that can prevent them. Furthermore, Kona, which is a vegetable pest that regenerates aphids, mites, and cruciferous vegetables, has acquired drug resistance in cotton ballworm and other pests. It is desired to develop a drug that can simultaneously control resistant pests.

In addition, in recent years, paddy rice cultivation in Japan has mainly been carried out by mechanical transplantation using young strawberry transplantation. It is desired to develop a drug that does not One more,
There is a desire to develop an excellent drug against pests that have become a particular problem in recent years, such as the rice weevil.

Therefore, important pests of food crops including rice and other insecticides, pests of horticultural crops such as vegetables, flower petals, and fruit trees, pests of craft crops such as tobacco, cotton, and tea, forest pests, and certain types of these pests. It is desired to develop a drug that has even more excellent effects against pests of greenhouse horticulture crops, soil pests such as nematodes, sweat-absorbing and feeding properties such as storage pests, and various pests in ponds.

As a result of intensive research aimed at solving the various problems described above, the present inventors surprisingly found that the insecticidal activity of the active compound mixture according to the present invention, which is a combination of a nitromethylene derivative and the above-mentioned known insecticides, It has been discovered that the effects of the active compounds are greater than the sum of their effects, exhibit excellent synergistic and synergistic effects, and have residual effects.

That is, by applying the insecticidal composition according to the present invention,
For example, it is effective against paddy field pests, such as Hemiptera pests, such as the Hemiptera larvae (e.g., the Lepidoptera larvae), and horticultural crop pests, such as fruit trees and legumes, such as the Lepidoptera larvae, Crucian carp 7y. It has been found that this can be achieved synergistically and synergistically at lower concentrations than with a single active compound alone, and that it has a residual effect.

Therefore, the insecticidal composition of the present invention is very effective in the cultivation of agricultural and horticultural crops, and provides extremely outstanding technological progress in terms of industrial usefulness.

The nitromethylene derivatives of general formula (1) used in the active substance combinations according to the invention are defined as follows.

In the formula, X represents a herodene atom, an alkyl group or an alkoxy group, n represents 0.1 or 2, and ■ represents 2 or 3.

- In general formula (1), preferably X represents a chlorine atom, a bromine atom, or a fluoro atom, n represents 1 or 2, noodle represents 2 or 3, and the bonding position of the birinone ring is 5. It is - position.

Examples of nitromethylene derivatives of the general formula (1) which can be used in the active substance combinations according to the invention include the following compounds: 3-(3-pyridylmethyl)-2-tromethylene)thiazolidine, 3-( 2-chloro-5-pyridylmethyl)
-2-totromethylene)thiazolidine, 3-(2-chloro-5-pyrinolmethyl-totromethylene)tetrahydro-2)1-1,3-thianone, 3-(2-promo5
-pyridylmethyl)-2-totromethylene)thiazolinone, 3-(2-promo5-pyridylmethyl)-2-totromethylene)tetrahydro-2H-1, 3
-thianone, 3-(2-fluoro-5-pyrinolmethyl)-2-tromethylene)thiazolidine, 3-(2-fluoro-5-pyrinormethyl)-2-tromethylene)
Tetrahydro-2 8- 1 , 3-thianone, 3-(
2.4-fuchloro-5-pyridylmethyl)-2-tromethylene)tetrahydro-2 1(-1.

3-thianone, 3-(2-methyl-5-pyridylmethyl)-2-tromethylene)thiazolinone, 3-(2-methyl-5-pyridylmethyl)-2-tromethylene)tetrahydro-28-1.3- thianone, 3-(2-7toxy5-pyridylmethyl)-2-tromethylene)tetrahydro-2l(-1°3-thiazine.

The nitromethylene derivative of the general formula (1) and its use as an insecticide have already been published by the present applicant (see Japanese Patent Application No. 18627/1983 and Japanese Patent Application No. 18628/1988).

The following compounds may be mentioned as one of the insecticides used in the active substance combination according to the invention: S,S'-2-nomethylaminotrimenalene bis(thiocarbamate) (cartap), N,
N-dimethyl-1,2,3-trithian-5-ylamine (thioeycla theory), 2 t
ert-butylimi/-5-iso-propyl-5-phenyl-1,3,5-thianoanonan-4-one (buprofezin), 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)
Urea (noflubenzuron diflubenzuro)
n), N-(2,6-difluorobenzoyl)-N'-[3
゜5-Nochloro-4-(5-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl 1-urea, 3-7eth/xybennol 2-(4-ethoxy7enyl)-2-notylpropyl Ether, 1-(4-)lifluoromethoquine-phenyl)-3-(2-chlorobenzoyl)urea, 1-(4-(2-fuchloro-1-nofluoroethoxy)-phenyl)-3-(2- chlorobenzoyl)urea, 1-(4-)lifluorophenyl)-3-(2,6-)
7fluorobenzoyl 1-(2,4-difluoro-3,5-nochlorophenyl)-3-(2,6-difluorobenzoylrea, and N-[6-(2,2.3-)+7fluoro3 −
Chloropenzonohesin-(1.4>>1-N'-
2.

6-di7fluorobenzoyl) flare.

The above-mentioned insecticides which are components of the active substance ff combination according to the invention are already known. That is, for example, The Pesticide Manual.
nual) m7 version 1983 (The Bri
tissueCrop Protection Cou
It has already been described as an insecticide in publications such as NCI 1, and is well known.

The weight ratio of the active compounds of each group in the active substance combination can be varied within a relatively wide range. in general,(
1) per lffiffi part of the active compound of the active compound group of the nitromethylene derivative of the general formula (I), (2) for example 0.05 to 10 parts by weight, preferably 0.1 to 10 parts by weight of the active compound of the active compound group of known insecticides. 5 heavy electrical parts can be used.

The active substance combination according to the invention exhibits an excellent insecticidal activity. Therefore, the active compound mixture can be used as an insecticide.
Stalk and foliage application, underwater or surface application, soil application, soil core. It can be used by Japanese processing, ¥rM box application, etc.

The active substance combination according to the invention exhibits a strong insecticidal action. Therefore, it can be used as an insecticide. Moreover, the active compound according to the present invention has no phytotoxicity to cultivated plants and is warm-blooded! Low toxicity to IllJ substances, A
It can be used for the precise control of pests, especially insects, in industry, forestry, and the protection of stored crops and products. They are usually active against sensitive and resistant species and at all or some growth stages.

For example, the insecticidal composition of the present invention can be used in particular for insect pests such as the planthopper M (e.g. brown planthopper, seven-spotted planthopper, and brown planthopper), leafhoppers, etc., lepidopteran larvae such as the larvae of the Lepidoptera, and coleopteran pests such as the rice water weevil. Paddy field pests and Lepidoptera pests such as crucian carp, armyworm,
Half-phase ■ Pest insects such as leaf beetles etc.
It can be effectively used to control pests of horticultural crops such as JiL rape.

The above-mentioned pests include, for example, the following: Examples of such pests include Coleoptera pests, such as the 7x Calloso-
bruchus chinensis), brown weevil (SiLopfiluszealIlais), tribolium easLane (Tribolium easLane)
um), Japanese lady beetle (Epilachna)
vigiLioctomaculata), Agriotes rusci
collis), Anomala ru
focusrea), Colorado Boted Beetle (Lep
tinoLarsa d(4cemkineata)
, diabrotica spp.
), Monocha+mu
s alternatus), rice weevil (L.
1ssorl+optrus oryzophil
us), rice weevil (Echinocinemus)
5qua+*eus), rice weevil (Oule
ma oryzac), oyster beetle (L yc
tu; bruneusL lepidoptera, for example, ymantria dispa
r), Malacosoma neus
Lria), Pierisrapae, Spodoptera 1itura
), armyworm (M amestra brassica
e), Chilo 5upres
salis), CnaphaIocro
cis medinalis), 7 Taobikoya If (
Naranga aenescens), 7wa/mayff (Pyrausta nubilalis), E pestia caute
lla), A doxophyes
orana), Kodori (Carpocal+:t
a pomonella), cabraya ff (AHr.

tis fuco3a), Honey If (G al
leria mellonella), crucian carp ff (P
luLclla 1IIaculipennis),
Heliothis viresce
ns), Citrus Hamoglyph F (I) hyllocnis
Lis citrella); Lis citrella (P
arnara guttata): semi-insects, such as the black leafhopper (N epl+oteLtix
cincticaps), brown planthopper (N 1l
aparvaLa lBen5), Japanese brown planthopper (
Laodelphax 5triatellus),
Seven White Planthopper (S ogatella furcif)
era), Pseudococ
cus comstocki), U naspis yanonensis, and peach aphid (Myzus persicae)
, apple aphid (Aphis l), cotton aphid (Aphis I?ossypii), false aphid (Rhopalosiphum)
pseudobrassicas), Nasigunbai (
StephanitiSnashI), green stink bug (
Nazara spp, ), T realeurodes vaporario
rum), Kinorami (Psylla spp,
); orthoptera, such as Gryllotalpa africana
, locust (Locusta migratoria)
ml); etc.

The active substance paper combination of the present invention can be in the form of a mixture of components (1) and V(2) or in the form of a conventional formulation of each separately for ex-situ mixing. Such forms include solutions, emulsions, suspensions, powders, foams,
Pastes, granules, aerosols, active compound infiltration - natural and synthetic products, microcapsules, seed coatings, preparations with combustion devices (e.g. combustion devices include fumigation and fume cartridges, guns and coils), sesame seeds. Then U L
'J [cold mist, warm mist].

These formulations can be manufactured by known methods. Such methods include, for example, combining the active compound with a vehicle, i.e., a liquid diluent; a liquefiable diluent, a solid diluent, or a carrier, optionally a surfactant, i.e., a fluorizing agent and/or a dispersing agent. This is carried out by mixing using agents and/or foam-forming agents. When using water as a developing agent, for example, organic solvents can also be used as co-solvents.

Liquid diluents or carriers are generally aromatic hydrocarbons X1t (e.g. xylene, toluene, furkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons M (e.g. chlorobenzenes, ethylene chloride, etc.). etc., methylene chloride, etc.), aliphatic hydrocarbons @ [e.g., cyclohehethane, etc., paraffin M (e.g., mineral oil fraction, etc.), alcohol M (e.g., butanol, glyfur and their ethers, esters, etc.), Mention may also be made of ketones M (eg acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexane, etc.), strongly polar solvents (eg trimethylformamide, trimethylsulfoxide?) and water.

Liquefied gas diluents or carriers are gases at room temperature and pressure, examples of which include aerosol propellants such as butane, propane, nitrogen, carbon dioxide, and halogenated hydrocarbons. Can be done.

Solid diluents include soil natural minerals (e.g. kaolin, clay, talc, chalk, quartz, heptadaloid,
montmorinite, diatomaceous earth, etc.), and soil synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.).

Solid carriers for granules include crushed and fractionated rocks (e.g. calcite, marble, pumice, sepiolite, white cloud 63
), synthetic grains of inorganic and organic phases, and fine grains or organic substances (for example sawdust, coconut berries, corn cobs and tobacco stalks, etc.).

Examples of emulsifiers and/or foaming agents include nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (
For example, furkylaryl polyglycol ethers,
Alkyl sulfonates, alkyl sulfates, arylsulfonates, etc.) 1, albumin hydrolysis products.

Examples of dispersants include lignin sulfide waste liquor and methylcellulose.

Fixed media can also be used in formulations (powders, granules, powders); such fixing agents include carboxymethyl cellulose and natural and synthetic polymers (e.g. gum arabic, polyvinyl alcohol and polyvinyl acetate). can be mentioned.

Coloring agents may also be used, including inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, 7zo dyes or metal 7 talocyanine dyes, and also , electrifying elements such as those salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be mentioned.

The formulations generally contain 0.1 to 95% by weight or 0.5 to 90% by weight of Mengki active ingredient.

The active substance combinations according to the invention are useful in their commercial applications, in their useful formulations and in the use forms produced by these formulations, and in their use as active compounds for ponds, such as insecticides, poison baits, fungicides, acaricides, etc. , nematocide, fungicide, growth 33
It can also be present as a mixture with I regulators or herbicides. Here, examples of the insecticide include organic phosphorus agents, carbamate agents, carboxylate agents, chlorinated hydrocarbon agents, and insecticidal substances produced from microorganisms.

Furthermore, the active substance combinations of the invention can also be present as admixtures with synergists, and such formulations and usage forms can include those that are commercially useful. The synergist need not be active itself, but is a compound that amplifies the action of the active compound.

The content of the active compound mixtures according to the invention in commercially useful use forms can vary within wide limits.

The working concentration of the active compound mixture according to the invention is, for example, 0.
．． 00001 to 100% by weight, preferably 0
．． 0004~1 double song%.

The active compound mixtures according to the invention can be used in the customary manner adapted to the use form.

When used to combat insect pests, the active compound is
B1 It is distinguished by its good stability against alkalis on the ash material, as well as its excellent persistence in wood and soil.

Next, the contents of the present invention will be explained in a synoptic manner using examples.
The present invention should not be limited to this only.

Example 1 Test sample for Cobb/May %J, liquid Y14 solvent 3 parts by weight of methylformamide Emulsifier: 1 part by weight of polyoxyethylene alkyl phenyl ether Each active compound to prepare the appropriate active compound formulation One part by weight was mixed with the above-mentioned solvent containing the JL-forming agent, and the mixture was diluted with water to a predetermined concentration.

? J, 9 method: Plant height about I planted in a vinyl pot with lrI diameter of about 9c+s
Plant three Sew rice plants, and y as above 10 days after planting.
Using a spray gun, use a spray gun to spread the diluted solution of the active compound in water at a predetermined concentration on a 920 ml cloth per bot, and after air-drying the spray solution, cover with a plastic mesh tube with a diameter of 9 cm and a height of 25 cm. 10 insects were inoculated per pot, and the insects were placed in a constant temperature room after 20 minutes, the number of dead insects was counted and the killing rate was calculated. Note that the test was conducted in duplicate.

The result! It is shown in Table 31.

Table 1 Testability against Fubu/Mei → 1. No drug damage was observed in all the mixtures and single agent uses tested in Example 14 2. Compounds of general formula (+) used in the present invention: Compound N
o, 1 3-(2-chloro-5-pyridylmethyl)-2
-(nitromethylene)thia/linone compound No. 2 3-(2-chloro-5-pyridylmethyl)-2-(nitromethylene)tetrahydro-28-1,3-thiazine 3, known insecticide used in the present invention Agent: Compound [A]: Cartap compound [B1: Thiocyclam Example 2 Test for Sejiroun force Test method: Three rice plants with a plant height of 15c+e were planted in a pot with a diameter of 13 cm, and after 10 plantings, the rice was prepared as in Example 1. Use a spray gun to dilute the active compound in water at a given concentration to 20ml per pot! Spread. After 10 sprayings and 20 days later, the pots were covered with a mesh tube and 10 fi of 3rd instar larvae of the seven-legged planthopper were inoculated per pot.The pots were placed in a constant temperature room, and the number of deaths was counted after 20 and 7 days to calculate the killing rate. Note that the test was conducted in duplicate.

The results are shown in the m2 table.

Table 2 Testability against Senoroun force) 1. No chemical damage was observed in all the mixtures and single agent applications tested in Example 2.

2. Compounds No. 1 and No. 2 of general formula (1) used in the present invention are the same compounds as in Example 1.

3. Known insecticides used in the present invention: Compound [C1 Nibuprophenone Example 3 Test against Kona Test method: As in Example 1, non-heading cabbage seedlings with a height of about 15 cm+A were planted in pots with a diameter of 9 cm. A water diluted solution of the prepared active compound with a predetermined concentration was sprayed at 20 + i/pot per pot using a spray gun, and after air-drying the sprayed chemical solution, 10 2nd instar Kona larvae were inoculated per pot and placed in a thermostatic chamber for 20 back and 7
After 0, the killing rate was calculated based on the number of deaths. By the way, the exam is a two-seat series.

Show the results to a third person.

- Measure ttS3 table Test hole for crucian carp ffl2) 1. No phytotoxicity was observed in all the mixtures and single agent uses tested in Example 3. Compounds No. 1 and No. 2 of general formula (1) used in the present invention were the same as Example 1. Indicates the same compound.

3. Compounds used in the present invention: [DI:1-(2,4-difluoro-3,5-nochlorophenyl)-3-(2,6-)7fluorobenzoyl)urea iE]:N-( 2,6-nofluorobenzoyl)-N
' -[3,S-nochloro-4-(3-chloro-5-trifluoromethyl-2-pyrinoloxy)7enyl l urea Example 4 Test against crucian carp Test method: Plants planted in pots with a diameter of 9 cm About 15c+n of non-heading cabbage seedlings were sprayed with a water diluted solution of the active compound at a predetermined concentration prepared as in Example 1 using a spray gun per 1 bot.
After spraying 20w4 and air drying the sprayed chemical solution, 10 per pot.
The 4th instar larvae of organophosphorus agent-resistant diamondback moth (I) were inoculated, placed in a constant temperature room, and 2 days later, the insecticidal rate was calculated by counting the number of deaths. The test was conducted in duplicate.

The results are shown in Table 4.

Note) 1. No phytotoxicity was observed in all the mixtures and single agent uses tested in Example 4. Compounds No. 1 and No. 2 of general formula (1) used in the present invention were the same compounds as in Example 1. show.

3. Compounds used in the present invention 4&l: [F 1; 3-Phenoxybennol 2-(4-ethoxyphenyl)-2-methylpropyl ether Example (Irrigation agent) Active compound of formula <1) 258S, Cartap 20 Part, mixture of powdered diatomaceous earth and powdered clay (1:5) 5s81
S, 2 parts of sodium alkylbenzene sulfonate, and 3 parts of sodium alkylnaphthalene sulfonate formalin condensate were pulverized and mixed to obtain an irrigation agent.

Claims (1)

[Claims] 1. (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) In the formula, X represents a halogen atom, an alkyl group or an alkoxy group, and n represents 0, 1 or 2. and m represents 2 or 3, and (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-thiadiazinan-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, 3
-Phenoxybenzyl 2-(4-ethoxyphenyl)-
2-Methylpropyl ether, 1-(4-trifluoromethoxy-phenyl)-3-(2-chlorobenzoyl)
Urea, 1-(4-(2-dichloro-1-difluoro-
ethoxy)-phenyl)-3-(2-chlorobenzoyl)urea, 1-(4-trifluorophenyl)-3-(
2,6-difluorobenzoyl)urea, 1-(2,4
-difluoro-3,5-dichloro-phenyl)-3-(
2,6-difluorobenzoyl)urea, and N-[6
-(2,2,3-trifluoro-3-chloro-benzodioxin-(1,4))]-N'-2,6-difluorobenzoyl)urea; An agricultural and horticultural insecticidal composition characterized in that it contains an active substance combination consisting of: