JPH05279211A - Insecticide for beetle - Google Patents

Abstract

PURPOSE:To provide the subject insecticide not only being effective at extremely low level of application, but high in the penetrability into crop and residual effect therein, also causing no chemical injuries on crop. CONSTITUTION:The objective composition containing, as active ingredient, a compound of formula I [R<1> and R<2> are each H, acyl derived from carboxylic acid, or COOR<3> (R<3> is alkyl, phenyl or benzyl)] or a salt thereof, pref. a compound of formula II. This composition is useful for applying on soybean, corn, the gourd family, Cruciferae, feed crop (leguminous pasture), and ornamental crop, having virtually no adverse effects on the environment and natural enemies.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to various insect pests belonging to the Chrysomelidae, which are harmful to crops such as food crops, vegetables, fruit trees, industrial crops, grass / feed crops, ornamental crops and forest trees. The present invention relates to a new insecticide for controlling pests.

[0002]

BACKGROUND OF THE INVENTION Chrysomelidae are generally relatively small beetles, but they have a relatively large number of species, can feed on various plants, and become an important pest when crops are harmed. Chrysomelidae pests include species that mainly feed on the leaves of crops, both larvae and adults. In addition, there are many species of adults that feed on leaves and their larvae damage roots in the underground.
For this reason, the detection of harm is delayed, causing a growth failure in various crops, and melons, cucumbers, and the like may suffer catastrophic damage such as die-off. In addition, even if the degree of damage is relatively low in potatoes, Japanese radish, and the like whose underground products are products, the damage to the food marks may cause the product value to be remarkably reduced or pathogenic bacteria to invade.

[0003] As important pests belonging to the Chrysomelidae in Japan, rice dwarf beetle, mud duck beetle, Urihamushi beetle, sour beetle beetle, Nastobi beetle, Urihamushi beetle, dwarf beetle beetle, beetle leaf beetle beetle, beetle leaf beetle, beetle leaf beetle and the like are known. .. These are rice and wheat, potatoes (potato, sweet potato, etc.), vegetables (radish, Chinese cabbage, cabbage, asparagus, eggplant, cucumber, watermelon, melon, etc.), fruit trees (apple, peach, grape, etc.), It is known to harm industrial crops (such as sugar beet, hemp, mint, etc.), various kinds of flowers, flowering trees, street trees, forest trees and the like.

Delis ^™ (rotenone) agent is known as a control agent for these pests of the Chrysomelidae family. Further, as the organic phosphorus agent, PMP powder, PMP wettable powder, ethylthiomethone granule, PAP powder, emulsion, propaphos granule, isoxathion powder, CYAP emulsion, dimethoate granule, MEP powder, MEP wettable powder and MEP emulsion, diazinon Known are powders, diazinon emulsions, diazinon wettable powders and diazinon granules, DDVP emulsions, CVP powders, phosalone emulsions and the like. Carbamate agents include carbosulfan granules, benfuracarb granules, PHP powder,
Known are PHP granules and PHP emulsions, NAC powders, NAC wettable powders, BPMC powders, BPMC powders, MPMC powders and the like. Known pyrethroids include etofenprox powder and cycloprotoline granules. Further, agricultural insecticides such as cartap powder and granules, bensultap powder and wettable powder are used alone or in combination with other agents for controlling beetle pests.

These known insecticides can be used by spraying a diluted solution of a liquid and a powder on the foliage of a crop, mixing a soil with a seed such as seeding a crop or planting a groove before transplanting,
Known methods include irrigation of liquid in napped hair, application of granules at the root, and seedling box treatment of granules before rice transplantation. However, since adults are generally active, they have the property of escaping when the foliage of the drug is sprayed and hiding in a place where the drug is hard to be exposed. Even if it is possible, it often does not show a practical control effect on the larvae in the underground.

[0006] Although soil-mixing treatment before transplantation and seedling box irrigation treatment of a drug having a systemic migration property are relatively effective methods, they have a short residual effect because they are treatments before the generation of pests. In some cases, the effect of the drug may not be fully exerted. Moreover, there is a problem that increasing the amount of the treated drug causes the drug to remain in the crop and the soil and causes a chemical damage to the crop.

[0007] In addition, the Delis ^™ (rotenone) agent, which is used effectively for Chrysomelidae pests, has a problem that its application is limited due to its strong fish toxicity.

Further, there are problems such as the emergence of Chrysomelidae pests which have recently acquired resistance to the above-mentioned known agricultural insecticides. There is a demand for the development of agricultural insecticides that can effectively control Chrysomelidae pests.

In recent years, nitroguanidine derivative-based pesticide pesticides have been developed and studied (JP-A-3-109374,
EP375907, EP-383091, JP-A-3-15
7308 (EP-376279), EP-471,372, etc.). However, the pesticide pesticide that can effectively control the Chrysomelidae pests has not been developed yet.

[0010]

SUMMARY OF THE INVENTION In view of the above problems of the prior art, an object of the present invention is to provide a novel insecticide for effectively controlling Chrysomelidae pests with an extremely small amount of active ingredient. Do

..

Means for Solving the Problems The present inventor has paid attention to nitroguanidine derivative-based compounds, and found that, among them, compounds having a specific structure exhibit an excellent insecticidal effect against Chrysomelidae pests. Through repeated studies, the present invention has been completed.

That is, the present invention has the formula (I)

[0013]

[Chemical 2]

[In the formula, R ¹ and R ² are the same or different and each represents an acyl group derived from hydrogen or a carboxylic acid or-
COO-R ³ is shown, and R ³ is an alkyl group, a phenyl group or a benzyl group. ] It is an insecticide for Chrysomelidae which contains the compound or its salt represented by these.

In the formula (I), the acyl group derived from the carboxylic acid represented by R ¹ and R ² preferably has 1 to 7 carbon atoms. Examples of the acyl group include an alkanoyl group, an aromatic acyl group and an aralkylcarbonyl group.

Specific examples of the alkanoyl group include formyl, acetyl, propionyl, butyryl, iso-butyryl, valeroyl, iso-valeroyl, 2,2-dimethylpropionyl, 2-methylbutyryl and the like. Preferred are acetyl, propionyl, butyryl, iso-butyryl, valeroyl.

The aromatic acyl group has 7 carbon atoms.
Alternatively, those of 8 and examples thereof include benzoyl and p-methylbenzoyl. Preferred is benzoyl.

Further, as the aralkylcarbonyl group,
It has 8 or 9 carbon atoms and includes phenylacetyl, 3-phenylpropionyl and the like. Preferred is phenylacetyl.

In the formula (I), the alkyl group represented by R ³ preferably has 1 to 4 carbon atoms. Specifically, methyl,
Examples include ethyl, propyl, iso-propyl, butyl, iso-butyl, tert-butyl and the like. Preferred is a methyl group.

A preferred combination of R ¹ and R ² is the same or different and is hydrogen, formyl, acetyl or methoxycarbonyl.

A preferred formula (I) is the following formula (I
I)

[0022]

[Chemical 3]

[Wherein R ¹ is as defined above. ] Is represented.

Of the formula (II), R ¹ is preferably hydrogen, formyl, acetyl, iso-butyryl, valeroyl, benzoyl, phenylacetyl or methoxycarbonyl. More preferred are hydrogen, formyl, acetyl and methoxycarbonyl. The salt of the compound (I) used in the present invention may be a salt that is acceptable in terms of agrochemical chemistry. For example, salts of inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid, perchloric acid, etc., or formic acid, acetic acid, tartaric acid, malic acid, citric acid, oxalic acid, succinic acid, benzoic acid. , Picric acid, methanesulfonic acid, P
-Salts of organic acids such as toluene sulfonic acid may be used.

The above compounds are known compounds and are disclosed in JP-A-3.
-157308 (EP-376279) and EP-471,372 can be obtained by the method described.

The pesticide of the present invention can be obtained by preparing an agrochemical formulation containing the above compound in an effective amount. The formulation to which the insecticide of the present invention can be applied is not particularly limited. For example, emulsion, oil, wettable powder, wettable powder, tablet, powder DL, granule,
Known agricultural chemical formulations such as propellants, ointments and seed coating agents can be mentioned.

The above-mentioned compound which is the active ingredient may be incorporated in the insecticide of the present invention in an effective amount against the pests of the Chrysomelidae. For example, in an emulsion, a wettable powder, a wettable granule, a sol, etc., 5 to 80% by weight of the above compound may be blended with respect to the total insecticide. The amount of oil or powder is 0.1 to 10% by weight, and the amount of granules is 0.2 to 20% by weight.

Further, the method of applying the insecticide of the present invention, the amount applied,
The frequency of spraying varies depending on the dosage form to be sprayed and the target crop, but may be appropriately selected.

For example, in the case of ordinary spraying of emulsions, wettable powders, etc., an insecticide having a concentration of 5 to 100 ppm is sprayed on vegetables at a rate of 10 to 40 liters / a, 1 to 4 times. Just scatter. In addition, the insecticide of 5 to 100 ppm concentration is applied to fruit trees and the like at a spray amount of 15 to 60 liters / a, and the amount is 1 to 4
Just scatter. Also, for rice, wheat, etc.
The insecticide having a concentration of 100 ppm may be sprayed 1 to 4 times at a spraying rate of 10 to 15 liters / a.

In the case of spraying a concentrated small amount of emulsion, wettable powder or the like or aviation spraying, 0.5 to 5% of insecticide is applied to rice, wheat or the like in an amount of 12 to 25 ml / a, 0.1 to 0.1. It is sufficient to apply 1% of the insecticide at 0.08 liter / a or 250 to 2,500 ppm of the insecticide at a spraying rate of 0.3 to 0.4 liter / a. The amount of drug applied and the number of sprays are the same as for normal spraying.

In the case of irrigation treatment of a stock in a parchment such as an emulsion or a wettable powder, an insecticide having a concentration of 5 to 100 ppm is applied to vegetables at a spraying amount of 50 ml to 500 ml per strain (of crops). Irrigation may be performed 1 to 4 times, depending on the stage).

In the case of treating seedbeds, nursery boxes and pots of emulsions and wettable powders, the insecticide of 5 to 100 ppm concentration is applied to vegetables and rice in an amount of 0.5 to 3 liters / m ² . You can spray or irrigate with.

When the granules are treated in the napped stock, the sprayed amount of 0.5 to 1 kg / a is applied to vegetables, rice, wheat, etc. 1 to 4 times on the soil surface of the stock. To do.

When sowing the granules or mixing the soil at the time of planting (processing the planting ditch and planting hole), mix once with a spray amount of 0.5 to 1 kg / a with respect to vegetables and the like. In the case of granule seedling box treatment, 30 to 120 g /
Mix the seedling box (60 cm x 30 cm x 3 cm) in the soil or spray the seedlings on the surface of the soil during planting.

It is also possible to carry out seed treatment. When seed coating is applied, 5-20 g of the active ingredient together with a bulking agent and a binder are added to the sugar beet seeds of 10,000
A coating treatment is applied to 0 grains (equivalent to 10a seeding). For example, 5 g to 30 g of the active ingredient is coated with a filler and a binder on radish seeds 0.8 to 1.8 (equivalent to 10a seeding). In the case of seed dressing,
A 10% wettable powder is applied to rice (seed paddy) or wheat (seed) weight of 0.5 to 1.0%. 10% for soaking seeds
Seeds such as rice, wheat and corn are immersed in a 50 to 100-fold solution of a wettable powder for 6 to 24 hours. In the case of the seed potato dressing, the insecticide of the present invention, in which 5% wettable powder is dressed with 0.3 to 0.4% of the weight of the potato seed at the time of planting, is a form which can be taken by general pesticides. Any formulation can be applied as long as it is available. For example, one or more compounds (I) or salts thereof as an active ingredient are dissolved or dispersed in a suitable liquid carrier or mixed or adsorbed with a suitable solid carrier depending on the purpose of use to prepare an emulsion, an oil agent. It is used as a dosage form for wettable powders, powders, granules, tablets, sprays, ointments and the like. These formulations may be emulsifiers, suspensions,
Spreading agents, penetrants, moist indigo, mucilages, stabilizers and the like may be added and can be adjusted by a method known per se.

The content ratio of the effective component in the insecticide varies depending on the purpose of use, but usually 10 to 90 for emulsions, wettable powders and the like.
About 10% by weight is suitable, and it is 0.1 for oils, powders, etc.
About 10 to 10% by weight is suitable, and as a granule, 1 to 20
Although the weight% is suitable, these concentrations may be appropriately changed depending on the purpose of use. Emulsions, wettable powders, etc. should be diluted appropriately with water before use (eg, 100 to 100,
000 times) and spray.

The liquid carrier (solvent) used is water,
Alcohols (methyl alcohol, ethyl alcohol,
n-Propyl alcohol, isopropyl alcohol, ethylene glycol, etc.), ketones (acetone, methyl ethyl ketone, etc.), ethers (dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, etc.), aliphatic hydrocarbons (Kerosine, kerosene, fuel oil, machine oil, etc.), aromatic hydrocarbons (benzene, toluene, xylene, solvent naphtha, methylnaphthalene, etc.), halogenated hydrocarbons (dichloromethane, chloroform, carbon tetrachloride, etc.), acids Amides (dimethylformamide, dimethylacetamide, etc.), esters (ethyl acetate, butyl acetate, fatty acid glycerin ester, etc.), nitriles (acetonitrile, propionitrile, etc.), etc. The solvent is suitably, it can be appropriately used by mixing one or two or more in an appropriate ratio.

As the solid carrier (diluting / extending agent), vegetable powder (soybean powder, tobacco powder, wheat flour, wood powder, etc.), mineral powder (kaolin, bentonite, clay such as acid clay, talc powder, wax) Talc such as stone powder, diatomaceous earth, silica such as mica powder, etc.), alumina, sulfur powder, activated carbon and the like can be used, and one or more kinds of these can be mixed and used at an appropriate ratio.

As the ointment base material, polyhydric alcohol ester of higher fatty acid (polyethylene glycol, pectin, glyceryl monostearate, etc.), cellulose derivative (methyl cellulose, etc.), sodium alginate, bentonite, higher alcohol, polyhydric alcohol, etc. One or more of alcohols (glycerin, etc.), petrolatum, white petrolatum, liquid paraffin, lard, various vegetable oils, lanolin, dehydrated lanolin, hydrogenated oil, resins, etc.,
Alternatively, those obtained by adding the various surfactants shown below to these are appropriately used.

As the surfactant used as an emulsifier, a spreading agent, a penetrating agent, a dispersant, etc., if necessary, soaps,
Polyoxyethylene alkyl aryl ethers [eg,
Neugen (trade name), E-A142 (E-A14
2) (trade name); manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd., nonal (trade name); manufactured by Toho Chemical Co., Ltd.], alkyl sulfates [eg,
Emar 10 (trade name), Emar 40 (trade name); manufactured by Kao Corporation], alkyl sulfonates [eg, Neogen (trade name), Neogen T (trade name); manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd., Neoperex; Kao Corporation], polyethylene glycol ethers [eg, Nonipol 85 (trade name), Nonipol 100 (trade name), Nonipol 160
(Brand name); Sanyo Kasei Co., Ltd.], polyhydric alcohol esters [eg, Tween 20 (Brand name), Tween 8]
0 (trade name); manufactured by Kao Corporation, etc., nonionic and anionic surfactants are appropriately used.

In addition, compound (I) or a salt thereof and an insecticide of another kind (pyrethroid insecticide, organophosphorus insecticide,
Carbamate insecticides, natural insecticides, etc., acaricides,
Nematicides, herbicides, plant hormones, plant growth regulators, fungicides (eg copper fungicides, organochlorine fungicides, organic sulfur fungicides, phenolic fungicides, etc.), synergists,
It is also possible to mix with an attractant, a repellent, a pigment, a fertilizer, etc. and use them appropriately.

For example, any of those described in Agricultural Chemicals Handbook (published by the Japan Plant Protection Association) can be used as a mixture with the insecticide of the present invention. In particular,
Pesticide fungicides and insecticides are preferably used as active ingredients. Representative examples of insecticides, acaricides and fungicides that can be used in the present invention are shown below.

Carbamate insecticide: propoxur (p
ropoxur), isoprocarb, BPMC, xylylcarb, metolcarb,
XMC, ethiofencarb, carbaryl, pirimicarb, bendiocarb, carbofuran, furathiocarb, carbosulfane
an), aminosulfulan, methomyl (met)
homyl), cartap (cartap), phenoxy curve (fenox
ycarb), alanicarb (alanycarb), chloetocarb (cl
oethocarb), benfuracarb, fenothiocarb, etc.

-Organophosphorus insecticide: fenthion (ffent
hion), fenitrothion, propaphos
(propaphos), cyanophos, prothiophos (p
rothiofos), sulprofos, profenofolks, EPN, cyanophenphos
nphos), acephate, oxydeprophos (o
xydeprofos), disulfoton, thiomethone
(thiometon), phenthoate, marathon
(malathion), dimethoate, vamidothion, mecarbam, trichlorphon, naled, dichlorphos
(dichlorvos), chlorofenvinpho
s), tetrachlorvinphos, monocrotophos, phosalone, dialifos, chlorpyrifos-methyl (chlorpy)
rifos-methyl), chlorpyrifos, pirimiphos-methyl, diazinon
azinon), etrimfos, pyridaphenthion, quinalphos, isoxathion, methidathione.
n), salithion, pyraclopho
s), chlorthiophos, fortress (fo
rtress), isofenphos, butathiophos
(butathiofos), EDDP, etc.

Pyrethroid insecticide: cyflucarin (c
yfluthrin), permethrin (permethrin), cypermethrin (cypermethrin), deltamethrin (deltamethrin),
Cyhalothrin, fenpropasulin (fenp
ropathrin), fenvalerate, flucythrinate, fluvalinate
ate), ethofenprox, silanophane, fenpropathri
n), tralomethrin, cycloprothrin
(cycloprothrin), acrinathrin, etc.

Urea-based insecticide: diflubenzuron (dif
ulbenzuron), chlorfluazuron,
Nomolt, hexaflumuron
n), flufenoxuron, diafenthiuron, flucycloxuron
xuron), hexythiazox, etc.

Other pesticides: thiocycrum
lam), buprofezin, benzulfap (b
ensultap), imidacloprid, hydroprene, fenazaquin, clofentedine, clofentezine, levamis
ol), dinochlor, cyromazi
ne), fenpyroximate, pyridaben, pyriproxyfen,
Sulfuramide (sufluramid), thiodicarb
Such.

Carbamate fungicide: Zineb (zine
b), maneb, benomyl, thiophanate-methyl, cypendazole (cyp)
endazole), carbendazim, prothiocarb, diethofencar
b) etc.

Antibiotic fungicide: validamycin A (v
alidamycin A), kasugamycin, avermectin, milbemycin, etc.

Anilide fungicide: mepronil
nil), flutolanil, penciclone (pency)
curon), carboxin, oxycarboxin
(oxycarboxin), pyracarbolid (pyracarbolid), mebenil (mebenil), flucarbanil (furcarbanil), cyclaframid (cyclafuramid), benodanil (benodanil), granovax (granovax), metalaxyl (metalaxyl),
Ofurace, benalaxyl, oxadixyl, cyprofuram, clozylacon, metsulfov
ax), tecloftalam, etc.

-Organophosphorus fungicides: edifenphos (edi
fenphos), IBP, pyrazophos, ariette, tolclofos-methy
l) etc.

-Azole-based fungicide: fenarimol (fen
arimol), flurprimidol, fluotrimazole, triadimephone (triadi)
mafon), triadimenole (triadimenole), clobutanol (diclobutazol), paclobutazol (paclobutazo)
l), diniconazole, uniconazole (u
niconazole), triflumizole (triflumizole), propiconazole (propiconazole), flutriafol (flutri)
afol), flusilazole, penconazole
(penconazole), prochloraz, triapenthenol, triarimo
l), fenarimol, bietetanol (biteta)
nol), imazalil, etaconazole (etacona)
zole) paclobutrazol (paclobutrazol), fenapronil (phenapronil), viniconazole (viniconazole),
Difenoconazole (difenoconazole), bromconazole (bromuconazole), microbutanil (myclobutanil),
Hexaconazole, cyproconazole (c
yproconazole), fluconazole-ci (furconazole-ci
s), fenethanil, tebuconazole (tebuc)
onazole) etc.

Dicarboximide fungicides: dichlozoline, iprodione, vinclozolin, procymidon
e), microzoline (myclozolin), fluoroimide (fluor
oimide) etc.

Other fungicides: fthalid
e), Monguard (trade name monguard), Isoprothiolane
(isoprothiolane), tricyclazole,
Probenazole (ferimzo)
n), fluazinam, butiobate (butiobat)
e), pyroquilon, chlobenzon (chlob
enchiazone, TPN, captan, captafol, folpet, thiabendazole, fuberidazol
e), tridemorph, fenpropimorph (f
enpropimorph), triforine, etirimol
(ethirimol), dimethylmol (dimethirimol), hymexazol (hymexazol), ethazol (ethazol), fenpropidin (fenpropidin), pyrifenox (pyrifeno)
x), dimethomorph, fenpiclonil (f
enpiclonil), zalilamide (zarilamid), trichlamide (t
riclamide), flusulfamide, flusulfamide, befran, dimefluazole, oxolinic acid, proxychl
or) etc.

Pheromone: okimerano
lure), cherry little (cherry tlure), diamorure (d
iamolure) etc.

Agrochemical active ingredients other than the above: Nitenpyram
(nitenpyram), fipronil, novaluron
(novaluron), flufenprox, fenpyrad or tebufen
pyrad), methoxadiazone, benfluthrin, pyriproxyfen
en), diafenthiuron, dichlorfluanid, ftalaxy
l), flapenazole, pipanipyrim (pipa
nipirim), thicyofen, ops (trade name, opus), ipconazole, dimetconazole, myxothiazo
l), thioimiconazole, quinconazole, etc.

The target beetle pests (CHRYSOMELIDAE: leaf beetles) and their crops to which the insecticide of the present invention is applied are as follows (listed in order of Japanese name, scientific name and English name).

(1) Rice: Rice duck beetle Oulema oryzae ( Kuwayama ), rice le
af beetle ； Rice Beetle Donacia provosti , Fair
maire rice rootworm etc.

(2) Wheat (winter cereals): Oulema erichsoni (Su
ffrian), wheat leaf beetle, etc.

(3) Millet, Atrachya menetriesi (Faldermann), false
melon beetle etc.

(4) Corn, maize: Atrachya menetriesi (Faldermann), false
melon beetle ； Diabrotica undecimpuctata howardi B
arber, southern corn rootworm ； Diabrotica longicor
nis (Say), northern corn rootworm; Di abrotica virg
ifera LeC., western corn rootworm ； Diabrotica balt
eata LeC., banded cucumber beetle ； Diabro tica unde
cimpunctata undecimpunctata Mannerheim, western sp
ottedcucumber beelte ； Chaetocnema pulicaria Melshe
imer, corn flea beetle; Chaetocnema denticulata (I
lliger), toothed flea beetle; Chaetocnema conofini
s Crotch, sweetpotato flea beetle ； Chaetocnema ect
ypa Horn, desert corn flea beetle ； Systena blanda
Melsheimer, pale-striped flea beetle ； Systena fron
talis (Fabricius), red-headed flea beetle; Phyllotr
eta pusilla Horn, western black flea beetle etc.

(5) Buckwheat: Strawberry leaf beetle Ga
lerucella grisescens (Joannis), strawberry leaf beet
le etc.

(6) Potato: Potato beetle Psylliodes angusticollis Baly,
solanumflea beetle (1) ； nano leaf beetle Psylliodes punctifrons Baly, cabbege fleabeetl
e ； Leptinotarsa decemlineata (Say), colorado potat
o beetle etc.

(7) Sweet potato: Sweet potato beetle Colasposoma dauricum Mannerheim, sweetpot
ato leaf beetle etc.

(8) Soybean: Aobanesarushi beetle, Basilepta fu lvipes (Mots)
chulsky) ； Aulacophora femoralis (Motsc
hulsky), cucurbit leaf beetle (1);
Atrachya menetriesi (Faldermann), false melon beet
le; Kiasinomi beetle Luper mor pha tunebrosa (Jacob
y), soybean flea beetle; leaf beetle, soybean flea beetle, Pagri a signata (Motschulsky), b
ean leaf beetle ； Medythia nigro
bi lineata (Motschulsky); Firefly leaf beetle (Black- winged beetle) Menolepta dichroa Harold etc.

(9) Kidney bean, Frenc
h been), adzuki bean, cowpea (cowpe)
a): Beetle leaf beetl, Pagria sign ata (Motschulsky),
e ； Feder beetle Medythia nif robilineata (Mot
schulsky) etc.

(10) Solanaceae vegetables [eggplant, tomato, chili pepper, pimenta]: eggplant beetle Psylliodes angusticollis Baly, solanumflea bee
tle ； nano leaf beetle Psylliodes puncti
frons Baly, cabbage fleabeetle ； Leptinotarsa decem
lineata (Say), colorado potato beetle etc.

(11) Cucumber [cucumber, melon, orientalpickling melo
n), watermelon (wataer melon), pumpkin (pumpkin, s)
quash)]: Aulacophora femoralis (Motsc)
hulsky), cucurbit leaf beetle; corn rootworm beetle Atr
a chya menetriesi (Faldermann), false melon beetle;
Black corn rootworm A ulacophora nigripennis Motschulsky
Such.

(12) Cruciferous vegetables [radish (radis
h), Chinese cabbage, cabbage
ge), turnip, cauliflower
r)]: Atrachya menetriesi (Falderm
ann), false melon beetle; Phyllotreta striolata (Fabricius), stri
ped flea beetle ； Peedon brassi
cae Baly, brassica leaf beetle; Phyllotreta chu joe Madar, etc.

(13) Liliaceous vegetables [onion, welsh onion, garlic, asparagus]: Crioceri
s orientalis Jacoby ； Cryptomeria japonica Cr
ioceris q uatuordecimp unctata (Scopoli) etc.

[0071] (14) Chinese yam (Chinese yam), yam (Japanese yam): Yellow neck Naga leaf beetle (yam neck Naga beetle) Lilioceris rugata (Baly); key Berri neck bombardier beetle Lema adamsii Baly; yam potato beetle (yam neck bombardier beetle) Lema honorata Baly, dioscorea
leaf beetle etc.

(15) Strawberry: strawberry beetle Altica fragariae (Nakane); strawberry leaf beetle
Galerucella gr isescens (Joannis), strawberry leaf
beetle; Hitomi Hime monkey beetle (Sakura monkey beetle) Cle
oporus variabilis (Baly); (16) citrus:
Cucumber leaf beetle Aulacophora nigripenni s Motschulsk
y; Kuwanomihamushi Luperomorpha funesta (baly), mulb
erry leaf beetle etc.

(17) apple, pear:
Tricholochmaea semifulva Jacob
y ； Cassida ver sicolor (Bohema
n); alder leaf beetle Agelastica coerulea Baly, alder
leaf beetle; leaf beetle Cleoporus variabilis (Baly); apple leaf beetle
Lypesth es ater (Motschulsky) etc.

(18) Peach, plum, Japanese apricot: Fleurtiauxia ar
mata (Baly) ； Varal beetle
C. larvae); Cleoporus variabilis (Baly); Lypesthes ater (Motschulsky) and the like.

(19) Grape: Nodina chalcosoma Baly; Red leaf beetle
Acrothinium gaschkevitschii (Motschulsky); Dougane salmon beetle Scelodonta lewisii Baly and others.

(20) Chestnut: Lypesthes ater (Motschulsky) and the like.

(21) Sugar beet: Acrothini um gaschkevitschii (Motschulsk
y); Urihamushimodoki Atrachya menetriesi (Falderman
n), false melon beetle; Kamenokohamushi Cassida nebu
losa Linnaeus, beet tortoise beetle ； Luperomorpha funesta (baly), mulberry leaf beet
le ； Tensite beetle Chaetocnema con cinna (Marsh
all) etc.

(22) Timer (hema) (hemp): Psylliodes attenuata (Koc)
h), hop flea beetle, etc.

(23) hop: Psylliodes attenuata (Koch), hop fle
abeetle etc.

(24) Mint: Urihamushimodoki
Atrachya mene triesi (Faldermann), false melon beetl
e; mint beetle Chrysolina e xanthematica (Wiedeman
n), peppermint leaf beetle; firefly leaf beetle (Korobane leaf beetle) Menolel pta dichroa Harold etc. (twenty five)
Forage crops [corn and sorghum
rghums)]: Oeder beetle
Oulema dilutipes (Fairmaire) etc.

(26) Forage crops [Graineous grass
forage grasses)]: Firefly beetle Menolelpta dichroa Harold; Chaetocnema cylindrica (Baly), barley flea be
etle etc. (27) Forage crops [leguminous fo
rage plants)]: Aoba ne monkey beetle (Kiashisaruhamushi), Basilepta fulvipes (Motschulsky); corn rootworm Aulacophora femoralis (Motschulsky); corn rootworm beetle Atrachya menetriesi (Faldermann), false melo
n beetle; leaf beetl, Pagria signata (Motschulsky), bean leaf beetl
e; Firefly leaf beetle Menolelpt
a dichro a Harold etc.

(28) Ornamental crops (flowers, garden trees) ornamenta
l plants, flowers and garden trees: Aphid beetle, Basilepta fulvipes (Mo
tschulsky); Itayahamushi Pyrrhalt a fuscipennis (Ja
coby); corn rootworm Aulacophora femoralis (Motschuls
ky), cucurbit leaf beetle; corn rootworm beetle Atrachy
a menetriesi (Faldermann), false melon beetle; Kaedehamushi Pyrrhalta seminigra (Jacoby); Katakuri beetle (Yurihamushi) Sangariola punctatostriata (Motsc
hulsky) ； Rubus chinensis Chaetocnema discreta
(Baly); black cucurbit leaf beetle Aulacophora nigripennis Mot
schulsky; Kuwahamushi Fleutiauxia armata (Baly); Sakura Kebu mosquito beetle Tr icholochmaea semifulva Jacoby;
Coral Ju Beetle Pyrrhalt a humeralis (Chen); Se Mont Zynga Sa Beetle (Se Mont turtle saw beetle), Cassida
v ersicolor (Boheman) ； Varal beetle (Varal beetle, Beetle beetle); Yurykubinaga beetle L
ilioceris merd igera (Linnaeus); Worm beetle Chrys
olina aurichalcea (Mnnerheim); beetle
Nonart hra cyanea Baly etc.

(29) Forest trees: Beetle Beetle Chujoa uetsukii (Chujo); Birch Beetle Syne
ta adamsi Baly ； Walnut Beetle (Walnut Beetle)
Gastrolina depressa Baly, walnut leaf beetle; Lypesthes i toi Chujo; sugi beetle B asilepta pallidula Baly, sugi
leaf beetle; Tenebrio monkey beetle (alder monkey beetle) Basilepta balyi (Harold); Tobisaruhamushi Trich
ochrysea japana (Motschulsky) ； Chrysanthemum beetle Chry
somela populi Linnaeus, red poplar leaf beetle ; Nirehamushi Pyrrhalta maculicollis (Motschulsky); Hagitsutsuhamushi Pachybrachis eruditus (Baly); alder leaf beetle Agelastica coerulea Baly, alder leaf beet
le ； Poplar beetle Chrysomela t
remulae Fabricius ； Gastrolina p
eltoides (gelbler) ； willow beetle C hrysomela vigint
ipunctata (Scopoli) ； Yanagiruri beetle Plagiodera v
ersicolora (Laicharting) ； Lypes
thes ater (Motschulsky) ； Ruri beetle Linaeidea aaen
ea (Linnaeus) etc.

Among the above, the pesticide of the present invention is particularly useful as a pesticide for soybeans, corns, cucurbits, cruciferous vegetables, forage crops (legumes of grasses) and ornamental crops for Chrysomelidae.

[0085]

INDUSTRIAL APPLICABILITY The insecticide provided by the present invention exhibits an excellent controlling effect against insects of the family Chrysomelidae which harm various crops. Not only effective in a very small amount,
Since it is highly permeable and transmissible to crops and has no residual effect, and no phytotoxicity to crops is observed, ordinary spraying, soil admixture treatment, other seedling box treatments, seed treatments, etc. are possible, making the drug more effective. It can be used and becomes an extremely excellent agricultural insecticide with little impact on environmental pollution and natural enemies.

[0086]

Examples [Table 1] and [Table 2] show typical compounds that can be used as the insecticide of the present invention.

[0087]

[Table 1]

[0088]

[Table 2]

[Formulation Example 1] Dust formulation 98.25 parts by weight of DL to 0.25 part by weight of the compound (No. 1),
1.0 parts by weight of white carbon and 0.5 parts by weight of I
P Solvent ^™ (manufactured by Idemitsu Petroleum Co., Ltd .: coagulant) was added and thoroughly mixed in an automatic mortar. Then, it was crushed with a flash mixer to obtain a powder DL.

[Formulation Example 2] Wettable powder 82.0 parts by weight of clay for wettable powder, 10.0 parts by weight of compound (No. 1), 5.0 parts by weight of Newcalgen BX-C ^™.
(Manufactured by Takemoto Yushi Co., Ltd.) and 3.0 parts by weight of white carbon were added and sufficiently mixed in an automatic mortar. Then, it was pulverized with a fine pulverizer to obtain a wettable powder.

Formulation Example 3 Emulsion 85.0 parts by weight of N-methylpyrrolidone were added with 10.0 parts by weight of the compound (No. 1) and 5.0 parts by weight of NP-85 (manufactured by Sanyo Kasei Co., Ltd.). In addition, the mixture was thoroughly stirred with a stirrer to obtain an emulsion.

[Formulation 4] Granules 93.5 parts by weight of finely divided clay, 1.0 part by weight of compound (No. 1), 5.0 parts by weight of dextrin and 0.5 parts by weight of NP-85 (SANYO). Kasei product number) was added and mixed well. Water was added to the mixture and kneaded, and the kneaded product was granulated by an extrusion granulator (screen 1.0 mm diameter) to obtain a wet granulated molded product. This was dried and then sized to obtain a granule.

[Test Example 1] Insecticidal effect against corn rootworm The insecticide of the present invention and the comparative insecticide were dissolved in a mixed solution of dimethylformamide (final concentration 0.1% by weight) and acetone (final concentration 0.1% by weight). Then, Tween 20 ^™ (final concentration: 0.05% by weight) was further added, and the mixture was diluted with water to a predetermined active ingredient concentration.

A spreading agent Dyne ^TM (manufactured by Takeda Pharmaceutical Co., Ltd., 20% by weight of polyoxyethylene nonylphenyl ether and 12% by weight of calcium lignin sulfonate) was added to this liquid.
Was added at a ratio of 0.03% by weight (final concentration) to prepare a drug solution.

Cucumber seedlings (variety: four leaves, second leaf stage) planted in a pot (diameter 6 cm) were placed in a polyethylene cup having a capacity of 860 ml and the succulent beetle ( Aulacophora
Five second-instar larvae of femoralis (Motschulsky) were released to each.

One day after the release of insects, 5.7 ml of the above chemical solution was irrigated on the soil surface of the pot, and five days after the treatment, cucumber seedlings were dug out and the number of surviving insects was investigated to determine the mortality rate.
The degree of feeding damage on the roots was observed and classified according to the following (number of repeats: 3). The test was conducted in a glass constant temperature chamber at 25 ° C. The test results are shown in [Table 3].

Degree of feeding damage: 0: No food marks are found 1: Slight food marks are found on the main root 2: Significant food marks are found on the main root 3: Larvae enter the crop base and cucumber Fall

[0098]

[Table 3]

As is clear from the results shown in [Table 3], the insecticide of the present invention was shown to have an excellent controlling effect on corn rootworm.

[Test Example 2] Controlling effect against the beetle flea beetle and the radish root beetle The insecticide of the present invention and the comparative insecticide were mixed with dimethylformamide (final concentration 0.1% by weight) and acetone (final concentration 0.1% by weight). Dissolve in liquid, and then Tween 2
0 ^™ (final concentration 0.05% by weight) was added, and the mixture was diluted with water to a predetermined active ingredient concentration.

To this liquid, a spreading agent Dyne ^™ (manufactured by Takeda Pharmaceutical Co., Ltd., 20% by weight of polyoxyethylene nonylphenyl ether and 12% by weight of calcium ligninsulfonate) was added.
Was added at a ratio of 0.03% by weight (final concentration) to prepare a drug solution.

Adults of Phyllotreta striola ta (Fabricius) and radish monkeys (average of 5.4) and Japanese radish monkeys were sown in the aboveground part of Japanese radish (variety: Hayatari Okura, 6-7 leaf stage) sown in a field in Kyoto city. Beetle ( Phae don b
Parasitism of adult ( rassicae Baly) heads (average of 4.2) was observed, so 2 m ² (0.8 × 2.5 m ² ) per plot in the field.
Was set up and 150 ml of the above chemical solution was sprayed per 1 m ² .

Two days after spraying the drug solution, the total number of surviving worms of the adult beetle flea beetle and the adult beetle dwarf beetle was investigated per ward, and the control value was calculated according to the following formula. The damage caused by the leaf beetle on the surface of the edible portion was examined by the following (repeat number: 2). The test results are shown in [Table 4].

Control value = 100 × {1- (number of surviving insects in treated area / number of surviving insects in untreated area)} Degree of feeding damage: 0: No trace of food marks 1: Slight trace of food marks 2 : Marked food marks are clearly recognized 3: Marked food marks are recognized and have no commercial value

[0105]

[Table 4]

As is clear from the results shown in [Table 4], the insecticide of the present invention is shown to have an excellent controlling effect on the root beetle and the leaf beetle.

Claims (1)

[Claims] 1. The formula: [In the formula, R ¹ and R ² are the same or different and each represents hydrogen, an acyl group derived from a carboxylic acid or —COO—R ³ , and R ³ represents an alkyl group, a phenyl group or a benzyl group. ] An insecticide for Chrysomelidae containing the compound represented by these or its salt.