JPS6256404A - Insecticidal composition for agriculture and horticulture - Google Patents

Abstract

PURPOSE:The titled composition useful for agricultural, horticultural crop culture, showing effects on insect pests in paddy field, such as leaf-hoppers, etc., insect pests in vegetables,such as plant lice, etc., in a low concentration, comprising an active mixture obtained by blending a nitromethylene derivative with a carbamate as an active ingredient. CONSTITUTION:A composition containing an active mixture consisting of (A) a nitromethylene derivative shown by the formula I(X is lower alkyl, lower alkoxy or halogen; l is 0, 1 or 2; m is 2 or 3), such as 1-(3- pyridylmethyl)-2-(nitromethylene)tetrahydropyrimidine, etc., and (B) a carbamate, preferably a compound shown by the formula II(R<1> is aryl, heterocyclic group or oxime; R<2> is H or lower alkyl; R<3> is lower alkyl, etc.) as an active ingredient. The blending ratio is preferably 0.1-20pts.wt., especially 0.2-15pts.wt. component B based on 1pt.wt. component A and the concentration of the active mixture in use is preferably 0.001-1wt%.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel Ikl# co-active compound mixture of nitromethylene derivatives and known carbamates having excellent insecticidal activity.

It has been discovered by the present applicant that nitromethylene derivatives have excellent insecticidal activity, and has already been published by Teil (Japanese Patent VF Application [1[59-26020, 59-72966,
59-132943).

It has already been described that the following carbamates have insecticidal activity. For example, 2-iso-proboxyphenylmethylcarbamate), 2-see-butylphenylmethylcarbamate, o-cumenylmethylcarbamate, etc.

However, the action of these known carbamates is not always satisfactory, especially when the concentration of active compound is low and when only a few mice are applied. Furthermore, as a result of using these insecticides over several years, some insect pests have acquired resistance, making it extremely difficult to control them.

(1) A nitromethylene derivative of the following general formula, where X represents a lower alkyl group, a lower alkoxy group or a halogen atom, l represents o, i or 2, and 2 or 3; 2) It has been found that a new active compound mixture of carbamates exhibits excellent insecticidal activity.

Conventionally, various pesticides have been developed as agricultural and horticultural insecticides, and have been used as single agents or mixtures. Especially with fi
IJ-type insecticides and carbamate-type insecticides are mainly used, and later, wide-type insecticides containing fins have been used. However, although each conventional insecticide has a certain type of insecticidal effect, the insecticidal spectrum and insecticidal effect (
Insecticidal effect on various live stage (e.g. eggs, larvae, adult insects), residual effect, fast effect, systemic transferability, and fish,
They do not fully satisfy various characteristics such as low toxicity to warm-blooded animals, reduced environmental pollution, and reduced number of applications and dosage.

Furthermore, as a result of the reverse use of conventional drugs, various insect pests have emerged that have acquired resistance to various insect pests. In particular, in recent years, hemiptera pests such as planthoppers and leafhoppers (e.g., leafhoppers) that have acquired resistance to organophosphorus insecticides and carbamate insecticides have appeared in rice paddies in various areas, including the warm southwest region of the country. However, it has become difficult to control them, and the development of superior drugs is desired. In addition, pests such as aphids, mites, and vegetable pests such as Kona and cotton balls, which attack vegetables, have acquired drug resistance, and it is necessary to control such resistant pests or to develop susceptible pests. It is desired to develop a drug that can simultaneously control insects and resistant pests.

In addition, in recent years, paddy rice cultivation in Japan has mainly been carried out by mechanical transplantation using a rice transplanter. There is a desire to develop drugs that are free from drug damage. Furthermore, there is a desire to develop a drug that is effective 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 grains, 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 facilities among these are important pests. It is desired to develop a drug that has even better effects against pests of horticultural crops, soil pests such as nematodes, sweat-absorbing and feeding insects such as storage TI pests, and other various pests.

As a result of intensive research to solve the various problems mentioned above, the present inventors surprisingly found that the insecticidal activity of a mixture of active compounds containing nitromethylene derivatives and known carbamates was higher than that of each individual compound. It has been discovered that the effects of the active compounds are greater than the sum of their parts and exhibit excellent cooperation and synergy.

That is, by applying the insecticidal composition according to the present invention,
For example, paddy field pests, such as Hemiptera pests such as planthoppers (e.g., brown planthopper), and plant pests, such as cattle pests.
It has been found that the effect against the pest aphids can be achieved cooperatively and synergistically at lower concentrations than with a single active compound alone.

Therefore, the insecticidal ML composition of the present invention has #! It is extremely effective in cultivating horticultural crops, and provides extremely outstanding technical progress in terms of industrial utility.

The nitromethylene derivatives of general formula (1) used in the active compound mixture according to the invention are defined as below, in which X represents a lower alkyl group, a lower alkoxy group or a halogen atom, and ! represents 0.1 or 2, and ω represents 2 or 3.

Particularly preferred nitromethylene derivatives of general formula (1) for use in the active compound mixtures of the invention are defined as below.

In the general formula (1), X preferably represents a methyl group, a methoxy group, a ral atom, a bromine atom or a fluoro atom, and! represents 1 or 2, K represents 2 or 3, and the bonding position of the birinone ring is the 3-position (or 5-position).

+ii The nitromethylene derivative of the general formula (1) described in [)-) Luenesulfonate, cupric acetate, succinate, etc. can be mentioned. Therefore,
The nitromethylene derivative of formula (1) used in the present invention is a term that includes the salt form thereof.

Examples of common nitromethylene derivatives used in the active compounds according to the invention include the following compounds: 1-(3-pyridylmethyl)-2-(nitromethylene)
Tetrahydropyrimidine, 1-(2-methyl-5-bilinormethyl)-2-(nitromethylene)imidazolidine, 1-(2-methyl-5-bilinormethyl)-2-tromethylene)tetrahydropyrimidine, 1-(2-methoxy -5-pyridylmethyl)-2-totromethylene)imidazolidine, ]-(2-methoxy-5-bilinormethyl)-2-totromethylene)tetrahydropyrimidine, 1-(2-chloro-5-bilinormethyl)-2-to Tromethylene) imidazolidine, 1-(2-chloro-5-pyridylmethyl)-2-nitromethylene)tetrahydropyrimidine, 1-(2-fluoro-5-pyridylmethyl)-2-nitromethylene)imidazolidine, 1- (2-fluoro-5-pyridylmethyl)-2-tromethylene)tetrahydropyrimidine, 1-(2-bromo-5-pyridylmethyl)-2-nitromethylene)imidazolidine, 1-(2-bromo-5-bilinormethyl) )-2-(nitromethylene)tetrahydropyrimidine, 1-(5-chloro-2-pyridylmethyl)-2-totromethylene)imidazolidine, 1-(5-chloro-2-pyridylmethyl)-2-totromethylene) Tetrahydropyrimidine, 1-(2,4-fuchloro-5-pyridylmethyl)-2-
(nitromethylene)tetrahydropyrimidine, t-(2
, 4-dibromo-5-bilinolmethyl)-2-totromethylene)imidazolidine, 1-(2,3-tsuk aa-5-pyrinolmethyl)-2-
1-(3-pyridylmethyl)-2-tromethylene)tetrahydropyrimidine-hydrochloride, 1-(2-methyl-5-bilinormethyl)-2-nitromethylene)tetrahydropyrimidine-9-) luenesulfonate, 1-(2-7toxy5-pyridylmethyl)-2-tromethylene)tetrahydropyrimidine-succinate, 1
-(2-chloro-5-pyrinolmethyl)-2-totromethylene)imigzolinone-hydrochloride, 1-(2-fluoro-5-pyridylmethyl)-2-totromethylene)tetrahydropyriminone-cuprous acetate salt, 1- (2-Bromo-5-pyridylmethyl)-2-tromethylene)imigzolinone-succinate, 1.(2,4
-fuchloro-5-pyrinonemethyl)-2-tromethylene)tetrahydropyrimidine-p-)yl sulfonate.

It has already been discovered and discovered by the present applicant that the nitromethylene derivative of general formula (1) has insecticidal activity (Japanese patent application No. 59-26020.59-72966).
．． 59-132943).

Preferred carparts to be used in the active compound mixtures according to the invention are of the general formula: in which R1 represents a substituted or unsubstituted aryl group, a polycyclic group or an oxime group, and R2 is a water $ atom. or represents a lower alkyl group, represents (
In the formula, R4 represents a lower alkyl group, and R5 represents a lower alkyl group, a lower alkoxycarbonyl group, or a lower alkoxycarbonyl alkyl group.

In the general formula (It) of the preferred car-bamate a, R
' is the same or different one or two carbon atoms 1 to 4
represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a 7-enyl group substituted with an ethylthiomethyl group, or R1 represents a 7-ethyl group, a noalkylamino group having 1 to 3 carbon atoms, preferably a pyrimidine group substituted with a trimethyl7mino group and two alkyl groups of 1 to 4 carbon atoms, preferably methyl groups, or 2,3 pyrimidine groups each substituted with an alkyl group of 1 to 4 carbon atoms, preferably a methyl group -represents a nohydrobenzo7ranyl group or a benzioxolyl group,
or R represents a furkyl group having 1 to 4 carbon atoms, preferably a methyl group, R7 represents a furkylthio group having 1 to 4 carbon atoms, preferably a methylthio group), and R2 represents a hydrogen atom or a methyl group having 1 to 4 carbon atoms. 4 alkyl group, preferably a methyl group, R3 is a furkyl group having 1 to 4 carbon atoms, preferably, R
Carbamate M is particularly preferred.

Examples of carbamates of general formula (II) include the following compounds: 2-iso-propoxyphenylmethyl carbamate (
propoxur), 0-thumenyl methyl carbamate (isoprocarb 1soprocarb)
, 2-see-phthylphenylmenalcarbame Hr3P
MC), 3.4-xylylmethylcarbamate (xylylcarb), m-lylmenalcarbamate (metolcarb meto
lcarb), 3.5-xylylmethylcarbamate (XMC),
a-ethylthio-〇-)lyl methyl carbamate, ethiofencarb), 1-s7thyl methyl carbamate (carbaryl)
, 2-cyphthyl 7mi/-5,0-tumethylpyrimidine-4
- Irtu methyl carbamate (virimicarb pi ``1 m
1carb), 2,2-methyl-1,3-pendioquine-4-yl methylcarb/-to(bennoocarb bendioc
arb), 2,3-dihydro-2,2-trimethylbenzofuran-furylmethylcarbamate (carbo7 arbof
uran), butyl 2,3-dihydro-2,2-i) methylbenzofuran-7-yl N,N-tumethyl-N,N-thiodicarbamate (furathiocarb
) 2,3-dihydro-2,2-dimethylbenzofuran-fuyl(butylamide/sulfenyl)(methyl)
Carbamate (carbosulfur)
ran), 2,3-dihydro-2,2-noanalbenzofuran-furyl N-(N-isopropyl-N-ethoxycarbonylethylami/sulfenyl)-N-methylcarbamate (7minosulfulan awinosulfulan), S -Methyl N-(methylruvamoyl axy)thio7cetimidate (methomyl me+, bomyl).

Carbamates, which are a key component of the active compound mixture according to the invention 1, are already known. That is, for example, the T be P estieide manual.
Manual) 7th edition 1983 (T I+e B
riLisl+ Crop Protection C
It is already known as an insecticide and has been described in publications such as published by Unci 1.

The weight ratio of the active compounds of each group in the active compound mixture can be varied within a relatively wide range. In general, <1) per 1 part by weight of an active compound of the active compound group of nitromenalene derivatives of the general formula (1), for example 0.1 to 20 parts by weight, preferably 0.1 to 20 parts by weight of an active compound of the active compound group of (2) carbamates. 2 to 15 parts by weight are used.

The active compound mixtures according to the invention exhibit excellent insecticidal activity. Therefore, the active compound can be used as an insecticide by foliar spraying, in water or surface application, soil application, soil mixing treatment,
It can be used by box application etc.

The active compound mixtures according to the invention exhibit a strong insecticidal action. Therefore, it can be used as an insecticide. Furthermore, the active compound according to the present invention has no phytotoxicity to cultivated plants and low toxicity to warm-blooded animals, and can accurately control pests, especially insects, in agriculture, forestry, storage, and product protection. It can be used in vain. They are usually
-C activity for sensitive and resistant species and all or some growth stages.

For example, the insecticide group and product of the present invention is particularly effective against pests of the order Hemiptera, such as planthoppers (e.g., brown planthoppers, brown planthoppers), leafhoppers, etc., rice field pests such as the rice weevil, which is a coleopteran pest, and pests of the order Hemiptera. Aphid gi
It can be effectively used to control pests of fruit trees such as X. and horticultural crops such as canola.

Furthermore, in addition to the above-mentioned pests, for example, the following harmful adzuki bean weevil (Callosobruchus chinen)
ais)-Lophilus z
ea+Ais), Tribol (Tribol)
castaneum), Epilachna vigiLioctomac
ulata), black-spotted woodpecker (Agrio)
tes fuscicoltiS), Himekofune (A
nomala rufocuprca), Colorado Boted Beetle (Leptinotar3a decewk)
ineaLa).

Diabrotica (D 1abroLica 31111
1. ), Monochamu
s alternatus), rice weevil (L
1ssorhoptrus oryzophilus)
, Lyctus bruneus
; Lepidoptera, for example, Lymantria dispar if (Lymantria dispar
), Malacosoma neustr
ia), P 1cres rapae, S podoptera I 1tur
a), Armyworm (Mamestra brassicae)
), Chilo 5uppressa
l is), Awanomei N (Pyraustan
ubiliS), Funamaguramei ff (Epbes)
tia caulella), Fukamon Hamaki (A d
oxophyes orana), robin, f (Ca
rpocapsa poaonella), Cabraya,
f (Asrotis fucosa), honey hemlock (
Galleria mellonella), Kosu W
(P Iutella +n+1culipcn old s)
, Heliotbis virsens
), the citrus leafminer (Pl+yllocnistis
ciLrella); semi-yA orders, e.g. Nepl+ote order, ix cin
eLiceps), Nilapar
vata Lugens), and Lao
delpl+ax 5 triatellus), Seven White Planthopper (S ogaLella furcifera)
, Pseudococcus
comStocki), Unas
pis yanonensis), green peach aphid (Myzus persicae), apple aphid (Aphis pomi), cotton aphid (Apb
is gossypii), false radish aphid (
RI+opalt>siphuw+pseud.

brassicas), Nasigunbai (S jepl+
antis nashi), green stink bug (Naza
ra spp,), T. ria
l eurodes vaporariorum)
, Psylla spp.; Orthoptera insects, e.g.
), locust (L oeustamid (rat, ori)
a migraLoriodes).

The active compound mixture according to the invention may be in the form of a mixture of components (1) and (2) or each ill for mixing in situ.
! It can be made into the usual formulation form of Jl. Such forms include liquid, emulsion, clouding agent, powder,
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), and tJLV (cold mls);
L), warm mist (war so mi!lt)).

These preparations can be manufactured by known methods. Such methods include, for example, combining the active compound with a spreading agent, i.e.
Liquid diluent; liquefied diluent; solid diluent or carrier;
This is carried out by mixing, optionally using surfactants, ie emulsifiers and/or dispersants and/or foam formers. When water is used as a developing agent, for example, hydroxide may also be used as a co-solvent 11'! Ru.

Liquid diluents or carriers include rings (7), aromatic hydrocarbons (such as xylene, toluene, alkylnaphthalenes), chlorinated aromatic or chlorinated aliphatic hydrocarbons (such as chlorobenzene), , ethylene chlorides, methylene chloride '4), aliphatic Ik hydrogen hydrides [e.g., cyclohexane, etc., paraffins (e.g., mineral oil fractions, etc.)], alcohols (e.g., butyl, glycol, and their ethers) , esters, etc.), ketones (eg acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexane, etc.), strongly polar solvents (eg dimethylformamide, trimethylsulfoxide, etc.) and water.

Liquefiable gas diluents or carriers are gases at normal temperature and pressure, examples of which include butane, propane, nitrogen gas, carbon dioxide, and aerosol propellants such as halogenated hydrocarbons. .

Solid diluents include soil natural minerals (e.g., cationic, clay, talc, silica, quartz, attapaloid, montmolinite, diatom, etc.), soil synthetic minerals (e.g., silicic acid, alumina, silicates, etc.) etc.).

Solid carriers for granules include well-pulverized and separated rocks (e.g., marble, pumice, sepiolite, dolomite, etc.), synthetic powders of inorganic and organic powders, and fine granules. Mention may be made of organic substances such as sawdust, coconut berries, corn cobs, tobacco stalks, etc.

Emulsifiers and/or foaming agents include non-ionic and anionic emulsifiers [e.g.
Examples include esters, polyoxyethylene fatty acids/alcohol ethers (e.g., alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonate M, etc.), and albumin hydrolysis products. .

Dispersants include, for example, genin sulfide waste liquor and methylcellulose.

Sticking agents can also be used in the formulations (powders, granules, emulsions), such as carboxymethylcellulose and natural and synthetic polymers (e.g. gum arabic,
polyvinyl alcohol and polyvinyl acetate, etc.)
can be mentioned.

Colorants may also be used, including free pigments (e.g. iron oxide, titanium oxide and Prussian blue), and organic dyes such as alizarin dyes, azo dyes or metal-7 talocyanine dyes, and also Trace elements such as iron, manganese, boron, copper, cobalt, molybdenum, and their salts of lead can be mentioned.

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

The active compound mixtures according to the invention, in their commercially useful formulations and in the use forms produced by them, contain other active compounds, such as insecticides, poison baits, fungicides, acaricides, Nematocide, fungicide, growth il!
It can also be present as a mixture with a trimming or removing agent. Here, the above-mentioned insecticides include, for example, organic phosphorus agents, carpoquinate agents, chlorinated hydrocarbon agents, and insecticidal substances produced from microorganisms.

Furthermore, the active compound mixtures according to the invention may also be present as admixtures with synergists; such formulations and usage forms may be those useful in commercial practice. The synergist does not need to be active per se, 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 concentration of use-L of the active compound mixture according to the invention is, for example, o, ooooi to ioo % overgrowth, preferably
The six active compound mixtures according to the invention of from o,ooi to 1% by weight can be used in the customary manner adapted to the form of use.

When used against stored pests, the active compound is
Not only does limestone have good stability against alkalis, but it also has excellent residual effects on wood and soil.
The content of the present invention will be specifically explained using an example using a dog, which is particularly emphasized, but the present invention should not be limited to this example.

Example 1 Preparation of test sample solution for brown planthopper Solvent: 3 parts by weight of xylene? L compound nQ: 1 part of polyoxyethylene alkylphenyl ether 1 part of polyoxyethylene alkyl phenyl ether 1 part of each active compound is mixed with the abovementioned solvent containing the above amount of emulsifier to prepare a suitable active compound formulation, and the mixture is It was diluted with water to the specified concentration.

Testing method: Plant 3 persimmons of about 15cm in diameter in a pot with a diameter of about 13cm, and after 10 days of constant heating, the is8! A diluted solution of the prepared active compound in water with a predetermined concentration was added using a spray gun.
Spray 20m1 per pot, and after air-drying the sprayed chemical solution, cover the pot with a net basket and kill 4th instar brown planthopper larvae at 910 kg per pot.
The insects were inoculated and placed in a greenhouse for 3 days, and the insecticide rate was calculated by counting the growth. The test was conducted in two consecutive matches.

The results are shown in Table 1.

Table 1: Against brown planthoppers? J, 9. ir,)1
．． No drug was observed in all mixtures and brush applications of the Example 1 test.

2. Compound (general formula) used in the present invention: Compound No.
, 1 1-(2-methyl-5-pyridylmethyl)-2-
Tetrahydropyrimidine Compound No. 2 1-(2-7toxy-5-bilinormethyl)-2-tromethylene) Tetrahydropyrimidine Compound No. 3 1-(2-bromo-5-pyridyl/tyl)-2-tromethylene ) Tetrahydropyrimidine Compound No. 4 1-(2-rioo-5-bilinormethyl)-2-totromethylene) Imidazolidine Compound No. 5 1-(2-fluoro-5-pyridylmethyl)-2-totromethylene) imidazo Lysine 3, compounds used in the present invention: [A]: Proboxur CB]: BPMC [C]: Isoprocarbo [D]: Metolcarb [E]: Xylylcarb [F] dicarbo7ane [G]: Carbosul7ane ( H) Niaminosulfan [■]: Bendiocarb Example 2 Test method: Approximately 100 cotton aphids kept per seedling were inoculated onto Solanum fungus with a height of about 15 cm planted in a pot with a diameter of 9 cm. [After 1 day, a water diluted solution of a predetermined concentration of the active compound prepared in TiI4 as in Example 1 was added using a spray gun.
2<)al was sprayed per bot, and after spraying, the plants were left in a greenhouse at 28°C. Two days after spraying, the dead were counted and the mortality rate was calculated.

The results are shown in Table 2.

Part 2 Test notes for cotton aphids〉1. In all the mixtures and single agent use in the test of Example 2, no -C toxicity was observed.

2. Compound No. of general formula (1) used in the present invention.

1, No. 12, No. 3, No. 4 and No. 5 indicate the same compounds as in Example 1.

3. Compounds used in the present invention: [A] 22,000 Offencarb [B]: Virimicarb 1 other person

Claims (1)

[Claims] 1. (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) In the formula, X represents a lower alkyl group, a lower alkoxy group, or a halogen atom, and l is 0, 1, or 2, and m represents 2 or 3. An agricultural and horticultural insecticidal composition characterized in that it contains an active compound mixture consisting of a nitromethylene derivative and (2) carbamates. 2. The carbamates in (2) described in claim 1 have the following formula ▲ Numerical formula, chemical formula, table, etc. ▼ (II) In the formula, R^1 is a substituted or unsubstituted aryl group, heterocycle represents a formula group or an oxime group, R^2 represents a hydrogen atom or a lower alkyl group, R^3
represents a lower alkyl group or group ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R^4 represents a lower alkyl group, and R^5
The agricultural and horticultural insecticidal composition according to claim 1, which is at least one compound selected from carbamates represented by the following: lower alkyl group, lower alkoxycarbonyl group, or lower alkoxycarbonyl alkyl group.