JPH11124306A - Insecticidal, acaricidal and fungicidal composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition showing excellently controlling activity against harmful organisms, having little adverse influence on mammals and useful organisms such as natural enemy, by including a specific acrylonitrile derivative and an active ingredient compound such as a well-known insecticide as active ingredients. SOLUTION: This composition comprises (A) one or more acrylonitrile derivatives of formula I (Q is a phenyl which may be replaced with W, etc.; A is a 5- or 6-membered heterocyclic group which may be replaced with Y such as thiazol-2-yl, etc.; B is H, etc,; Y is a halogen, etc.; W is a halogen, etc.), and (B) one or more active ingredient compounds of well-known insecticide, acaricide and fungicide, preferably fenbutatin oxide, etc., as active ingredients. A compound of formula II is preferable as the component A. The composition is used in the form of an emulsion and is effective for controlling Tetranychus urticae, citrus red mite, Plutella xylostella, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a pesticidal composition comprising a mixture of a novel acrylonitrile derivative and an active compound of a known insecticide, acaricide and fungicide. .

[0002]

2. Description of the Related Art As an acrylonitrile derivative, for example, JP-A-53-92769 discloses 2'-chloro-3-hydroxy-2- (4-phenyl-2-thiazolyl) -cinnamic acid nitrile. . Also, Japanese Unexamined Patent Publication No.
No. 1452 describes 2- (4-chlorophenyl) -3- (3-pyridinyl) -3-oxopropionitrile as a herbicide, and JP-A-60-11401 discloses the compound as a fungicide. Is described.

[0003]

SUMMARY OF THE INVENTION Today, agricultural and horticultural pests,
Development of insecticides, miticides, and fungicides for controlling various pests such as forest pests and sanitary pests has been widely promoted, and a wide variety of drugs have been put to practical use. However, in recent years, pests have acquired insecticide resistance and pathogens have acquired fungicide resistance due to the long-term use of such agents, and as a result, the number of situations where it has become difficult to control with conventional agents has increased. Also, some of these drugs are highly toxic, and some are persisting in the environment for long periods of time, disrupting ecosystems. Therefore, development of a new drug having not only a high pest control effect but also a low toxicity and a low residue is always expected.

[0004] On the other hand, considering the diversity of insects and pathogens as a group of living organisms, their mode of attack, and the variety of situations in which they attack, it is difficult to use these new drugs or existing known drugs alone. It is very difficult to effectively control all pests in pest control situations. Therefore, there is also a strong demand for a new method for inducing a higher control effect by appropriately combining a plurality of insecticides and / or miticides and / or fungicides and controlling pests which are difficult to control.

[0005]

Means for Solving the Problems In view of such circumstances, the present inventors have demonstrated an excellent control activity, and
As a result of intensive studies to develop pest control agents having little adverse effect on useful organisms such as fish and natural enemies, the following compound groups [1] to [4] are highly safe and excellent pest control. Activity. Furthermore, in the course of the research, the insecticidal / miticidal / bactericidal composition of the present invention, which combines these acrylonitrile derivatives with known insecticides, acaricides, and fungicides, cannot be predicted from use alone. The inventors have found that they have excellent synergistic insecticidal, acaricidal and bactericidal effects, and completed the present invention.

[1] Equation (1):

[0007]

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[Wherein Q is a phenyl group optionally substituted by W or a 5-membered heterocyclic group optionally substituted by R (provided that a thiazol-2-yl group, a thiazole-
4-yl group, thiazol-5-yl group, pyrazol-1
-Yl group, pyrazol-3-yl group, pyrazol-4-
Selected from an yl group and a pyrazol-5-yl group. )
A represents a 5-membered ring or a 6-membered ring optionally substituted with Y
Membered heterocyclic group (provided that thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl) Yl group, pyrazol-5-yl group, pyridine-
2-yl group, pyridin-3-yl group and pyridine-4
-Selected from yl groups. And B represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyalkyl group having 2 to 4 carbon atoms, a methoxyethoxymethyl group, a tetrahydropyranyl group, a trimethylsilyl group, or an alkylsulfonyl group having 1 to 4 carbon atoms. , -SO ₂ CF _3, mono or di - 1 to 4 carbon atoms alkyl - aminosulfonyl group, a phenyl aminosulfonyl group, a mono- or di - C1-C4 alkyl - amino thiocarbonyl group, -COT ^1, alkaline N which is a metal, alkaline earth metal or ammonium group
T ² T ³ T ⁴ T ⁵ , provided that when Q is a thiazol-2-yl group, B represents an alkyl group having 1 to 4 carbon atoms and 2 carbon atoms;
To 4 alkoxyalkyl group, methoxyethoxymethyl group, tetrahydropyranyl group, trimethylsilyl group, an alkylsulfonyl group having 1 to 4 carbon atoms, -SO ₂ CF _3, mono or di - C1-C4 alkyl - aminosulfonyl A phenylaminosulfonyl group, a mono- or di-alkyl group having 1 to 4 carbon atoms, an amino-aminothiocarbonyl group,
—COT ¹ represents NT ² T ³ T ⁴ T ⁵ which is an alkali metal, alkaline earth metal or ammonium group;
Are each independently a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms,
6 halocycloalkyl group, cycloalkyl group having 3 to 6 carbon atoms which may be substituted by alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 6 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms An alkylsulfenyl group having 1 to 4 carbon atoms, an alkylsulfinyl group having 1 to 4 carbon atoms, and 1 carbon atom
To 4 alkylsulfonyl groups, nitro groups, cyano groups, amino groups, monoalkylamino groups having 1 to 6 carbon atoms, dialkylamino groups having 1 to 6 carbon atoms which are the same or different, benzyl group, phenoxy group, hydroxy group, Naphthyl group,
An alkoxy-carbonyl group having 1 to 4 carbon atoms, a phenyl group optionally substituted with X, a pyridyl group optionally substituted with X, a thienyl group optionally substituted with X, Alkoxyalkyl group and 2 to 4 carbon atoms
Represents one or more substituents arbitrarily selected from among the alkylcarbonyl groups (however, when the number of the substituents is two or more, they may be the same or different from each other), or two adjacent substituents Represents a 5-, 6-, 7- or 8-membered ring formed by a substituent, wherein W is a halogen atom,
6 alkyl groups, haloalkyl having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms, alkylsulfenyl group having 1 to 4 carbon atoms, 1 carbon atom
An alkylsulfinyl group having 1 to 4 carbon atoms, an alkylsulfonyl group having 1 to 4 carbon atoms, a haloalkylsulfenyl group having 1 to 4 carbon atoms, a haloalkylsulfinyl group having 1 to 4 carbon atoms,
Haloalkylsulfonyl group having 1 to 4 carbon atoms, 2 to 2 carbon atoms
An alkenyl group of 4, a haloalkenyl group having 2 to 4 carbon atoms,
C2-4 alkenyloxy group, C2-4 haloalkenyloxy group, C2-4 alkenylsulfenyl group, C2-4 alkenylsulfinyl group, C2-4 alkenylsulfonyl Group, carbon number 2
A haloalkenylsulfenyl group having 2 to 4 carbon atoms, a haloalkenylsulfinyl group having 2 to 4 carbon atoms, a haloalkenylsulfonyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms,
C2-4 haloalkynyl group, C2-4 alkynyloxy group, C2-4 haloalkynyloxy group, C2-4 alkynylsulfenyl group, C2-4 alkynylsulfinyl group, alkynylsulfonyl group having 2 to 4 carbon atoms, halo alkyl Nils Le phenyl group having 2 to 4 carbon atoms, halo alkynylsulfinyl group having 2 to 4 carbon atoms, halo alkynylsulfonyl group having 2 to 4 carbon atoms, NO _2, CN , Formyl, an alkoxycarbonyl group having 2 to 6 carbon atoms, an alkylcarbonyl group having 2 to 6 carbon atoms, a haloalkylcarbonyl group having 2 to 6 carbon atoms and an alkylcarbonyloxy group having 2 to 6 carbon atoms. Substituents (however, when the number of the substituents is two or more, they may be the same or different from each other), and the number of the substituents is 1, 2, 3, Or a five, T ¹ represents an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, 3 to 6 carbon atoms which may be substituted with an alkyl group having 1 to 3 carbon atoms a cycloalkyl An alkyl group, an alkoxy group having 1 to 6 carbon atoms, a monoalkylamino group having 1 to 6 carbon atoms, a dialkyl-amino group having 1 to 6 carbon atoms, a phenylamino group,
Represents a phenyl group which may be substituted by Z or a naphthyl group which may be substituted by Z, wherein T ² , T ³ , T ⁴ and T ⁵ each independently represent a hydrogen atom, an alkyl having 1 to 6 carbon atoms; A alkenyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a benzyl group which may be substituted by an alkyl group having 1 to 3 carbon atoms, or T ² ,
Any two selected from T ³ , T ⁴ and T ⁵ may be taken together with a nitrogen atom to form a heterocyclic 5-, 6-, 7- which may optionally contain another hetero atom, oxygen, nitrogen or sulfur. −
Or may form an 8-membered ring, X and Z are each independently a halogen atom, an alkyl group having 1 to 4 carbon atoms,
An alkoxy group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, an alkylsulfenyl group having 1 to 4 carbon atoms, an alkylsulfinyl group having 1 to 4 carbon atoms, an alkylsulfonyl group having 1 to 4 carbon atoms, C1-4 haloalkyl group, nitro group, cyano group, C1-4 monoalkylamino group, same or different C1-4 dialkylamino group, phenyl group, benzyl group, phenoxy group, hydroxy And one or more substituents arbitrarily selected from the group and an alkoxy-carbonyl group having 1 to 4 carbon atoms (however, when the number of the substituents is two or more, they may be the same or different from each other). An acrylonitrile derivative represented by the formula:

[2] Q is a thiazol-4-yl group optionally substituted with R or a thiazol-5-yl group optionally substituted with R, wherein R is a halogen atom, and has 1 to 6 carbon atoms. Alkyl group, alkenyl group having 2 to 6 carbon atoms, alkynyl group having 2 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, halocycloalkyl group having 3 to 6 carbon atoms, alkyl group having 1 to 3 carbon atoms A cycloalkyl group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, an alkylsulfenyl group having 1 to 4 carbon atoms, Alkylsulfinyl group having 1 to 4 carbon atoms, alkylsulfonyl group having 1 to 4 carbon atoms, nitro group, cyano group, amino group, monoalkylamino group having 1 to 6 carbon atoms, dialkylamino group having the same or different 1 to 6 carbon atoms , Benzyl group, phenoxy group, naphthyl group, alkoxy-carbonyl group having 1 to 4 carbon atoms, phenyl group optionally substituted with X, pyridyl group optionally substituted with X, and optionally substituted with X One or more substituents arbitrarily selected from a thienyl group, an alkoxyalkyl group having 2 to 4 carbon atoms and an alkylcarbonyl group having 2 to 4 carbon atoms, wherein Y is a halogen atom,
Alkyl group of 1-4, alkoxy group of 1-4 carbon atoms, haloalkoxy group of 1-4 carbon atoms, alkylsulfenyl group of 1-4 carbon atoms, alkylsulfinyl group of 1-4 carbon atoms, 1-carbon atoms 4 alkylsulfonyl groups, having 1 to 1 carbon atoms
4, haloalkyl group, nitro group, cyano group, 1 to 1 carbon atoms
4 monoalkylamino group, same or different dialkylamino group having 1 to 4 carbon atoms, phenyl group, benzyl group, phenoxy group, hydroxy group, alkoxyalkyl group having 2 to 4 carbon atoms, alkyl having 2 to 4 carbon atoms The above-mentioned [1], which is one or more substituents arbitrarily selected from a carbonyl group and an alkoxy-carbonyl group having 1 to 4 carbon atoms;
The acrylonitrile derivative according to the above.

[3] Q is a pyrazol-1-yl group optionally substituted with R, a pyrazol-3-yl group optionally substituted with R, and a pyrazol-4-yl group optionally substituted with R. An yl group or a pyrazol-5-yl group optionally substituted with R, wherein R is a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkynyl having 2 to 6 carbon atoms. Group, haloalkyl group having 1 to 6 carbon atoms, halocycloalkyl group having 3 to 6 carbon atoms, 1 carbon atom
3 to 6 carbon atoms which may be substituted with an alkyl group
Cycloalkyl group, C1-6 alkoxy group, C1-4 haloalkoxy group, C1-4 alkylsulfenyl group, C1-4 alkylsulfinyl group, C1-4 Alkylsulfonyl group, nitro group, cyano group, amino group, monoalkylamino group having 1 to 6 carbon atoms, dialkylamino group having the same or different 1 to 6 carbon atoms, benzyl group, phenoxy group, naphthyl group, carbon number 1-4 alkoxy-carbonyl group, phenyl group optionally substituted with X, pyridyl group optionally substituted with X, thienyl group optionally substituted with X, alkoxyalkyl having 2-4 carbon atoms And at least one substituent arbitrarily selected from a group and an alkylcarbonyl group having 2 to 4 carbon atoms, wherein Y is a halogen atom,
Alkyl group of 1-4, alkoxy group of 1-4 carbon atoms, haloalkoxy group of 1-4 carbon atoms, alkylsulfenyl group of 1-4 carbon atoms, alkylsulfinyl group of 1-4 carbon atoms, 1-carbon atoms 4 alkylsulfonyl groups, having 1 to 1 carbon atoms
4, haloalkyl group, nitro group, cyano group, 1 to 1 carbon atoms
4 monoalkylamino group, same or different dialkylamino group having 1 to 4 carbon atoms, phenyl group, benzyl group, phenoxy group, hydroxy group, alkoxyalkyl group having 2 to 4 carbon atoms, alkyl having 2 to 4 carbon atoms The above-mentioned [1], which is one or more substituents arbitrarily selected from a carbonyl group and an alkoxy-carbonyl group having 1 to 4 carbon atoms;
The acrylonitrile derivative according to the above.

[4] An acrylonitrile derivative selected from the following compound group:

[0012]

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[0013]

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The other active ingredient compound of the composition of the present invention is a well-known compound which is well known as an active ingredient compound of insecticides, acaricides, and fungicides. However, the present invention is not necessarily limited to these.

Examples of insecticides and acaricides include organophosphorus compounds represented by fenitrothion, phentoate, dimethoate, bamidothion, thiomethone, propafos, chloropyrifos, etc., permethrin, cypermethrin, bifenthrin, fenpropathrin, etofen. Pyrexroid compounds represented by Prox, fenvalerate, etc., carbamate compounds represented by carbaryl, carbosulfan, mesomil, thiodicarb, ethiophencarb, pirimicarb, etc.,
Diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, benzoylphenylurea compounds represented by hexaflumuron, etc., acetamiprid, nitenpyram, chlornicotyl compounds represented by imidacloprid, etc., and fipronil, tebufenozide, pyriproxyfen, Chlorofenapyr,
Triazuron, pymetrozine, diafenthiuron, dicofol, phenisobromolate, propargite, clofentezin, amitraz, fenbutane tin oxide,
Hexitiazox, pyridaben, ethoxazole, tebufenpyrad, pyrimidifen, fenpyroximate and the like.

Further, examples of fungicides include dithiocarbamate compounds represented by zineb, maneb, manzeb, polycarbonate, diram, thiuram and the like, and N-haloalkylthioamide compounds represented by captan, folpet, captaphor and the like. , Halogenated aromatic compounds represented by chlorothalonil, PCNB, fusalide and the like, quinone compounds represented by dithianone and the like, iprodione, vinurozolin,
Dicarboximide compounds such as procymidone, benomyl, carbentazim, topzin M, benzimidazole compounds such as thiabendazole, metalaxyl, oxadixyl,
Acylalanine compounds represented by benalaxyl, offrace, cyprofuram, etc .; strobilurin compounds represented by kresoxime methyl, azoxystrobin, methominaphen, etc .; mepanipyrim, pyrimethanil, aniline represented by cyprodinil, etc. Linopyrimidine compounds, propiconazole, prochloraz, triflumizole, triadimefon, triadimenol, bitertanol, microbutanyl, flusilazole, cyproconazole, hexaconazole, imibenconazole, fluquinconazole, metconazole,
Fenbuconazole, epoxyconazole, tebuconazole, bromoconazole, tetraconazole, diconazole, triazole / imidazole compounds represented by diphenoconazole, pyrimidine compounds represented by phenarimol, tridemorph, fenpropi Morpholine compounds represented by morphs, etc .; organophosphate compounds represented by IBP, EDDP, fosetyl, etc .; antibiotics represented by blasticidin S, kasugamycin, polyoxin, validamycin, etc. Substance, organic copper, basic calcium sulfate copper, copper hydroxide sulfate, basic copper chloride, cupric hydroxide, fludioisinyl, quinoxaline, fluazinam, iminoctadine acetate, iminoctadine albecil, carboxyl Emissions, oxycarboxin, diflumetorim, spiroxamine, Kinikishifen, diethofencarb, tricyclazole, probenazole, pyroquilon, ferimzone, carpropamid, flutolanil, pencycuron, thifluzamide, furametpyr, like cymoxanil and inorganic sulfur.

[0017]

BEST MODE FOR CARRYING OUT THE INVENTION The -C (CN) = C (OB)-part of the acrylonitrile derivative represented by the formula (1), which is one of the active ingredient compounds of the composition of the present invention, has an E-form and a Z-form. There are two isomers, both of which are included in the present invention. It is understood that the acrylonitrile derivative which is one of the active ingredient compounds of the composition of the present invention can exist in a tautomeric form represented by the following formula when the substituent B in the formula (1) is a hydrogen atom. There will be.

[0018]

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The compound is thought to exist predominantly in the enol form (1 '), but under certain conditions may take the tautomeric form (2) and the exoolefin form (2').
It is to be understood that the present invention includes all three tautomeric forms and mixtures thereof.

The acrylonitrile derivative, which is one of the active ingredients of the composition of the present invention, is different from conventional drugs such as organochlorine insecticides, organophosphorus insecticides, carbamate insecticides and pyrethroid insecticides. Things,
In addition, some insect pests can die at a low dose and have residual effects, resulting in a remarkable control effect. In addition, acrylonitrile derivatives
It exhibits preventive or curative activity at a low dose for certain diseases, and consequently exerts a remarkable control effect. However, it goes without saying that it is impossible to control all pests or diseases in all fields by using only this oxopropionitrile derivative.

On the other hand, the other active ingredient compound of the composition of the present invention is known as an active ingredient of insecticides, acaricides, and fungicides, and is actually used.
However, these drugs tend to increase the amount and frequency of spraying of drugs due to the emergence of drug-resistant pests or resistant bacteria, and the lack of insecticidal sterilization spectrum and residual efficacy. Alternatively, there are many problems in terms of environmental safety, such as an increase in danger to aquatic organisms.

The characteristics of the insecticidal / miticidal / bactericidal composition of the present invention are, firstly, that the insecticidal / miticidal / bactericidal efficacy is clearly enhanced and immediate effect as compared with the case where each agent is applied alone. In other words, the insecticidal / miticidal / bactericidal effect is imparted. Second, a broad insecticidal / miticidal / bactericidal spectrum not found in existing insecticides and / or miticides and / or fungicides, and long residual efficacy is induced. Third
Another advantage is that the dose of the drug can be reduced as compared with the case where each drug is used alone.

That is, the composition of the present invention has a synergistic insecticidal / miticidal / bactericidal action. This synergistic insecticidal / miticidal / bactericidal action is based on a synergistic effect that cannot be predicted from the insecticidal / miticidal / bactericidal properties of each single agent, and the usefulness of the composition of the present invention is useful for various pests. On the other hand, it can be said that each agent can exert a more reliable control effect than using each agent alone.

The composition of the present invention includes so-called agricultural pests, agricultural diseases that damage agricultural and horticultural crops and trees, so-called livestock pests that infest livestock and poultry, so-called sanitary pests that adversely affect the living environment of humans such as houses, and The present invention can be applied to mites and nematodes that cause and harm in similar situations. Pests that can be controlled using the composition of the present invention, mites, nematodes,
Specific examples of the disease include the following, but are not limited thereto.

The insect pests include Spodoptera litura (Spod)
optera litura) and Cubomeiga (Cna)
phalocrocis medinalis, Plutella xylostella, Giant moth (Mamestrabrassicae), White butterfly (Pieris rapae crucivo)
ra), Kaburaya (Agrotis segetu)
m), Anemone oyster (Adoxophyes)
sp. ), Chahamaki (Homona magnan)
ima), tobacco bat worm (Heliothis)
virscens), European corn borer (Ostoria nubilis), fall army worm (Spodoptera frugip)
erda), Corn ear worm (Helicover)
pzea), lepidopteran pests such as the leafhopper leafhopper (Nephotettix cincticeps),
Brown Planthopper (Nilaparvata lugen)
s), peach moth aphid (Myzus persic)
ae), Halyomorphami
sta), bed bugs (Cimex electrical)
ius)

[0026] A ladybird (Epilach)
na vitignoctunctata), Buddy buoy (Anomala cuprea), Rice weevil (Lissorhopterus ory)
zophilus), Southern corn root worm (, Northern corn root worm (Diacrotica b)
arberi), Western corn rootworm (Di)
abrotica virgifera virgif
era), Scotophilusoryz
ae) and other insects of the order Coleoptera, Musca do
mesica), Culex pipiens (Culex pipi)
ens pallens) and the bean leaf fly (Lir)
iomyza trifolii, sea flies (Da
cucucurbitae), Thrips palmi (Thrips palmi), Thrips tabaci, and Frankliniella ococcus (Thrips tabaci)
citellalis), cat fleas (Ctenocephalidae felis), and keops rat flea (Xenopsylla cheop)
is), pests of the order Isoptera such as chicken psyllid (M
pests such as Enacanthus stramineus, bovine lice (Bovicola bovis),

Bovine lice (Haematopinus)
eurysternus), Lice lice (Lino)
gnathus vitili)
Citrus red mite (Panonychus citri),
Spider mite (Tetranychus urtica)
e), Kanzawa spider mite (Tetranychus ka)
spider mites such as nzawai;
ticks (Polyphag) such as Urops pelekassi, Acaphylla theavagrans and the like.
otersonmus latus, Cyclamen dust mite (Steneotarsonmus pal)
dust mite such as C. lidus,
yrophagus putrescentiae),
Robin mite (Rhizoglyphus robin)
i) and other acarid mites;
usmicroplus), ticks such as tick ticks, rabbit ticks (Psoroptes)
uncunuli), Sheep squash mite (Psor)
optes ovis), sarcoptic mites such as Sarcopes scabiei, sweet potato nematodes (Melo)
idogyne javanica, Pratylenchus penetra
ns) and potato cyst nematode (Globo)
nematodes such as dera rostochiensis).

On the other hand, the disease is rice blast (P
ricularia oryzae, sesame leaf blight (Cochliobolus miyabeanu)
s), sheath blight (Rhizoctonia solan)
i), wheat powdery mildew (Erysiphe gra)
minis f. sp. hordei, f. sp, tr
itici), leaf spot disease (Pyrenophora gr)
aminea), net spot disease (Pyrenophorat)
eres), Fusarium head blight (Gibberella zea)
e) Rust (Puccinia striiform)
is, P. Graminis, P .; recondit
a, P. hordei), snow rot (Tipulas)
p. , Micronectriella nivai
s), naked smut (Ustilago tritici,
U. nuda), eye spot (Pseudocerc)
osporella herpotrichoide
s), cloud disease (Rynchosporium sec.)
alis), Leaf blight (Septoria tritic)
i), blight disease (Leptosphaeria nodo)
rum), citrus black spot (Diaporthe c)
itri), scab (Elsinoe fawcett)
ti), fruit rot (Penicillium dig)
italum, P .; italicum), Monilia disease of apple (Selerotinia mali), rot of rot (Valsa mali),

[0029] Powdery mildew (Podaspera l)
cucotricha), spot leaf spot (Alterna)
ria mali, scab (Venturia in)
aequalis), Pear scab (Venturia)
nasicola), black spot (Alternari)
a kikuchiana), scab (Gymnosp)
orangium haracanum, peach scab (Sclerolinia cinerea), scab (Cradosporium carpophil)
um), Phomopsis rot
p. ), Downy mildew of grape (Plasmopara vi)
ticola), black rot (Elsinoe ampe)
lina), late rot (Glomerella sing)
ulata), powdery mildew (Uncinula nec)
ator), rust (Phakopsora ampe)
lopsidis, oyster anthracnose (Gloeospo)
rium kakj), deciduous disease (Cercospora)
kakj, Mycosphaerella nawa
e), downy mildew of cucumber (Pseudoperenosp)
ora cubensis, anthracnose (Colleto)
trichum lagenarium), powdery mildew (Sphaerotheca fuliginea),
Vine blight (Mycosphaerella melon)
is), Tomato plague (Phytophthora i)
nfestans), ring spot disease (Alternaria)
solani), leaf mold (Cladosporium)
fulvum), brown spot of eggplant (Phomopsis)
vexans), powdery mildew (Erysiphe c)
ichoracoarum),

Black spot of cruciferous vegetables (Alterna)
ria japonica, vitiligo disease (Cercosp)
orella brassicae, green onion rust (Puccinia allii), soybean purpura (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (D)
iaporthe phaseolum, an kidney anthracnose (Colletotrichum Lind)
emutianum), Peanut black spot (Myc)
osphaerella personatum, brown spot (Cercospora arachidicol)
a), Pea powdery mildew (Erysiphe pi)
si), potato summer blight (Alternaria)
solani), strawberry powdery mildew (Sphaero)
theca humuli), tea net blast (Exo)
basidium reticulatum, white scab (Elsinoe leucospila), tobacco scab (Alternarialingipes), powdery mildew (Erysiphe cicholacear)
um), anthracnose (Colletotrichum ta)
bacum), brown spot of sugar beet (Cercospor)
a beticola, rose scab (Diploc)
apon rosae, powdery mildew (Sphaer)
otheca pannosa), brown spot of chrysanthemum (Se)
ptoria chrysanthemiindic
i), white rust (Puccinia horian)
a), Botrytis c of various crops
innerea) and sclerotium disease of various crops (Schler)
otinia sclerotiorum) and the like.

Examples of acrylonitrile derivatives included in the present invention are shown in the following table. The abbreviations in the table have the following meanings. Me: methyl group, Et: ethyl group, nPr: normal propyl group, iPr: isopropyl group, cPr: cyclopropyl group, nBu: normal butyl group, iBu: isobutyl group, sBu: secondary butyl group, tBu: tertiary butyl group , NHex: normal hexyl group, c
Hex: cyclohexyl group, Ph: phenyl group

[0032]

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[0033]

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[0034]

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[0035]

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[0036]

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Table 1

[0038]

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[0039]

[Table 1] ──────────────────────────────── No. R ¹ R ² R ³ BA mp (℃) ─ ─────────────────────────────── I-1 Ph HHH A1 144-145 I-2 Ph Cl HH A1 300 <I -3 Ph H Me H A1 300 <I-4 Ph Me HH A1 141-143 I-5 Ph HH B1 A1 75-77 ^* I-6 Ph HH B2 A1 Viscous oil I-7 Ph CO ₂ Et HH A1 202-203 I-8 Ph HHH A2 300 <I-9 Ph HHH A7 124-125 I-10 Ph HHH A8 265-267 I-11 2-poly HHH A1 290 <I-12 2-poly HHH A2 300 <I -13 2-poly HHH A3 260-267 I-14 2-poly HHH A4 300 <I-15 2-poly HHH A6 297-298 I-16 2-poly HHH A7 163-165 I-17 2-poly HHH A8 300 <I-18 2-poly HHH A9 240-245 I-19 2-poly HHH A10 261-266 I-20 2-poly HHH A11 232-234 I-21 2-poly HHH A12 284-287 I-22 2 - pyridyl HHH A13 300 <I-23 2- pyridyl HH B7 A7 103-110 ^* ───────────────────────────────

[0040]

[Table 2] Table 1 (continued) ──────────────────────────────── No. R ¹ R ² R ³ BA mp (℃) ──────────────────────────────── I-24 2-Phenyl HH B8 A1 Viscous oil I-25 3-poly HHH A1 298-300 I-26 3-poly HHH A2 158-160 I-27 3-poly HHH A7 168-169 I-28 4-poly HHH A1 251-253 I-29 2-F -Ph HHH A1 125-126 I-30 2-F-Ph HHH A2 281-282 I-31 2-F-Ph Cl HH A1 281-287 I-32 3-F-Ph HHH A2 300 <I-33 4 -F-Ph HHH A2 169-173 I-34 2-Cl-Ph HHH A1 Viscous oil I-35 2-Cl-Ph HHH A2 Viscous oil I-36 3-Cl-Ph HHH A1 141-149 I-37 3-Cl-Ph HHH A7 291-293 I-38 4-Cl-Ph HHH A1 186-188 I-39 4-Cl-Ph HHH A7 300 <I-40 2,6-F ₂ -Ph HHH A1 267-269 I-41 2,6-F ₂ -Ph HHH A2 300 <I-42 2,6-F ₂ -Ph HHH A7 242-243 I-43 2,6-Cl ₂ -Ph HHH A1 147- _{148 I-44 2,6-Cl 2} -Ph HHH A2 100-102 I-45 tBu HHH A1 viscous oil ────── ─────────────────────────

[0041]

[Table 3] Table 1 (continued) ──────────────────────────────── No. R ¹ R ² R ³ BA mp (℃) ──────────────────────────────── I-46 tBu HHH A2 65-67 I-47 2 -MeO-Ph HHH A1 300 <I-48 2-MeO-Ph HHH A2 300 <I-49 H CO ₂ Et Ph H A1 236-237 I-50 Me Ph HH A1 Viscous oil I-51 cHex HHH A1 204-205 I-52 1-Naphthyl HHH A1 225-227 I-53 2-Thienyl HHH A1 146-147 I-54 2-Thienyl HHH A7 271-273 I-55 Ph HHH A34 173.3-174.1 I-56 Ph HH B1 A34 Viscous oil ^* I-57 Ph HH B7 A1 140-141 ^* I-58 Ph HH B8 A1 50-51 ^* I-59 Ph HH CO ₂ tBu A1 Viscous oil I-60 tBu CO ₂ Me HH A1 105-106 I-61 tBu CO ₂ Me H B7 A1 125-126 I-62 Ph HH B7 A2 Viscous oil I-63 2,6-F ₂ -Ph HH B8 A2 200-201 I-64 Ph HH B6 A2 Viscous oil I-65 2,6-F ₂ -Ph HH Na 2,6- (MeO) ₂ -Ph 300 <I-66 2,6-F ₂ -Ph HH Na 2-CF ₃ O- Ph 282.8-287.2 I-67 2,6-F ₂ -Ph HH Na 2-MeO-Ph 300 <───────── ───────────────────────

[0042]

[Table 4] Table 1 (continued) ──────────────────────────────── No. R ¹ R ² R ³ BA mp (℃) ──────────────────────────────── I-68 2,6-F ₂ -Ph HHH 2 -CF ₃ O-Ph 157.9-160.1 I-69 2-Pyridyl HH B8 A7 118-119 ^* I-70 2,6-F ₂ -Ph HH B7 A2 Viscous oil I-71 Ph HHH 2-Cl-Ph 108-109 I-72 Ph HHH 2,6-F ₂ -Ph 167-168 I-73 Ph HHH 2,6-Cl ₂ -Ph 170-171 I-74 Ph HHH 2-CF ₃ -Ph Viscous oil I-75 Ph HHH 1-Naphthyl 137-138 I-76 Ph Ph HH A2 145-147 I-77 Ph HHH 2-Cl-4-F-Ph 94-95 I-78 Ph HH B35 A2 164-165 I- 79 2,6-F ₂ -Ph HHH 2-Me-Ph 113.1-119.8 I-80 2,6-F ₂ -Ph HHH 2-Cl-6-F-Ph 144-146 I-81 2,6-F ₂ -Ph HHH 2-NO ₂ -Ph 176-179 I-82 2,6-F ₂ -Ph HHH 2-AcO-Ph Glassy I-83 2,6-F ₂ -Ph HHH 2,6-Me- Ph Glassy I-84 2-Phenyl HHH 2,6-F ₂ -Ph 188-189 I-85 2-Phenyl HHH 2,6-Cl ₂ -Ph 278-280 I-86 2-Phenyl HHH 2-NO ₂ -Ph 285-287 I- 87 2-polyhyl HHH 2-MeO-Ph 275-276 I-88 2-polyhyl HHH 2-CO ₂ Me-Ph 248-249 I-89 2-polyhyl HH B7 2-Cl-Ph 124-125 ──── ────────────────────────────

[0043]

[Table 5] Table 1 (continued) ──────────────────────────────── No. R ¹ R ² R ³ BA mp (℃) ──────────────────────────────── I-90 2-Phenyl HH Na 2-Cl-Ph 278-280 I-91 2-Phenyl HHH Poly-2-yl 216-217 I-92 2-Philid HH COnC ₁₇ H ₃₅ A7 58-59 I-93 tBu CO ₂ Me HH 2-Cl-4-F-Ph 114-115 I-94 tBu CO ₂ Me H B7 A2 105-106 I-95 tBu CO ₂ Me HH A2 102-103 I-96 tBu HH B7 A2 viscous oil I-97 tBu HH B7 A2 viscous oil ^{# 1} I-98 tBu NO ₂ H B7 A2 Viscous oil I-99 tBu Br H B7 A2 Viscous oil I-100 tBu CN HH A2 178-180 I-101 tBu CN H CO ₂ tBu A2 Glassy I -102 tBu CN H CO ₂ tBu A2 201-202.5 ^{# 2} I-103 tBu CN H CO ₂ Ph A2 Glassy I-104 tBu Cl H B7 A2 Viscous oil I-105 tBu CO ₂ Me H CO ₂ iBu A2 155.8-156.9 I-106 tBu Cl HH A2 Viscous oil I-107 tBu NO ₂ HH A2 87-88 I-108 tBu CO ₂ nHex HH A2 Glassy I-109 tBu CO ₂ Me H B8 A2 152.1-153.5 I-110 tBu Me HH A2 Glassy I-111 tBu CO ₂ Me H COnC ₁₇ H ₃₅ A14 Viscous oil ─────────── ─────────────────────

[0044]

[Table 6] Table 1 (continued) ──────────────────────────────── No. R ¹ R ² R ³ BA mp (℃) ──────────────────────────────── I-112 tBu CO ₂ Me H B7 A14 Viscous oil Object I-113 tBu CO ₂ Me HH A14 101-102 I-114 tBu Me H B7 A2 Glassy I-115 tBu CO ₂ Me H B7 A3 131-132 I-116 tBu CO ₂ Me H Me A2 166-167 ^* I-117 tBu CO ₂ Me H B3 A14 Viscous oil I-118 tBu CO ₂ Me HH A21 152.6-154 I-119 tBu CO ₂ Me H COnC ₉ H ₁₉ A3 Viscous oil I-120 tBu CO ₂ Me ^{H B7 A15 125-127 * I-121} tBu CO 2 Me HH A15 138-139 I-122 tBu CO 2 Me H B7 A21 viscous oil _{I-123 tBu CO 2 Me H} COnC 5 H 11 A21 viscous oil I-124 tBu CO ₂ Me H COnC ₅ H ₁₁ A21 Viscous oil ^{# 3} I-125 HH 2,6-F ₂ -Ph H A2 157.4-162.4 I-126 H Ph HH A1 Glassy I-127 H tBu H B7 A2 Glassy I-128 H tBu HH A2 Glassy I-129 2-Philidyl HH B7 A37 86-94 ^{# 4} I-130 2-Philidyl HH B7 A1 0 92-93 I-131 2-polychloride Cl H B7 A7 Viscous oil ^* ─ *: E or Z form, # 1: I-96 geometric isomer, # 2: I-101 geometric isomer, # 3: I-123 geometric isomer, # 4: E / Z = 2 / 1 mixture

Table 2

[0046]

Embedded image

[0047]

[Table 7] ────────────────────────────── No. RBA mp (℃) ───────── ───────────────────── II-1 Ph H A1 200-205 II-2 2-Cl-Ph H A2 137-138 II-3 tBu H A2 151 -153 II-4 tBu B3 A2 147-150 ^* II-5 tBu B7 A2 89.5-92 ^* II-6 tBu H A1 Viscous oil ^* II-7 tBu B7 A1 Viscous oil ^* II-8 tBu H 2 , 6-F ₂ -Ph 90-92.5 II-9 tBu H 2-Cl-Ph 96.2-98.6 II-10 tBu B6 A2 Glassy ^* II-11 tBu B5 A2 Viscous oil II-12 tBu B8 A2 Viscous Oil II-13 tBu SO ₂ (4-Cl-Ph) A2 Glassy ^* II-14 tBu H 2,6-Cl ₂ -Ph 150.3-151.7 II-15 tBu H 2-CF ₃ -Ph 71.9-79.6 II -16 tBu H A3 viscous oil II-17 tBu B7 A3 viscous oil ^* II-18 tBu CO ₂ Et A2 viscous oil II-19 tBu CO ₂ CH ₂ Ph A2 viscous oil II-20 tBu CONMe ₂ A2 136.7-138.2 II-21 tBu CH ₂ CO ₂ Me A2 Viscous oil II-22 tBu PO (OEt) ₂ A2 Viscous oil II-23 2-poly H A2 184.5-188.5 ───── ──────── ─────────────────

[0048]

[Table 8] Table 2 (continued) ────────────────────────────── No. RBA mp (℃) ─── ─────────────────────────── II-24 2-poly H A7 210.3-218.8 II-25 2-poly B7 A7 162.7-167 ^* II-26 2-Phenyl B7 A2 Glassy ^* II-27 2-Phenyl H A3 148-151 II-28 2-Phenyl B7 A3 Glassy ^* II-29 2-Phyllic H A35 188-193 II-30 2-Philyl B7 A35 200.5-202.5 ^* II-31 2-Pyridyl H A36 Viscous oil II-32 2-Pyridyl B7 A36 Viscous oil II-33 cHex H A2 126.5-128.1 II-34 cHex H 2,6-F ₂ -Ph 110.9-112.7 II-35 cHex B7 2,6-F ₂ -Ph 111.2-117.4 ^* II-36 cHex B7 A2 Viscous oil ^* II-37 2,6-F ₂ -Ph H A2 176.8-178.2 II -38 2,6-F ₂ -Ph B7 A2 95.9-98.0 ^* II-39 2-Cl-Ph H A2 172.9-175.2 II-40 tBu B35 A2 glassy II-41 tBu B35 A2 glassy ^{# 5} II-42 tBu B36 A2 Glassy II-43 tBu H A13 168- 173 II-44 tBu B28 A2 Glassy II-45 tBu B30 A2 Glassy ──────────────────────────────

[0049]

[Table 9] Table 2 (continued) ────────────────────────────── No. RBA mp (℃) ─── ─────────────────────────── II-46 tBu B30 A2 Glassy ^{# 6} II-47 tBu CO (2-Me-Ph) A2 Glassy II-48 tBu B38 A2 Glassy II-49 tBu B37 A2 Glassy II-50 tBu Nicotinol A2 Glassy II-51 tBu B40 A2 Glassy II-52 tBu CO ₂ iBu A2 Viscous oil II-53 tBu CO ₂ Ph A2 viscous oil II-54 tBu B41 A2 viscous oil II-55 tBu CO ₂ nHex A2 Viscous oil II-56 tBu H 3-Cl-Ph 89.7-91.1 II-57 tBu H 3-F-Ph 63.7-64.4 II-58 tBu H 2-Br-Ph 86-87 II-59 tBu H 2 -I-Ph Glassy II-60 tBu H 2-Cl-6-F-Ph 109.6-110.6 II-61 tBu CO (2-MeS-Ph) A2 Glassy II-62 tBu H 2-MeS-Ph 120.6- 122.1 II-63 tBu H A22 113-118 II-64 tBu B7 A22 98-99.5 ^* II-65 tBu B15 A22 Viscous oil II-66 tBu B38 A13 Viscous oil II-67 tBu B39 A2 Glassy ── ────────────────────────────

[0050]

[Table 10] Table 2 (continued) ────────────────────────────── No. RBA mp (° C) ─── ─────────────────────────── II-68 tBu CO (4-Cl-Ph) A2 Glassy II-69 tBu CO (3- Cl-Ph) A2 Glassy II-70 tBu B7 2,6-F ₂ -Ph Viscous oil II-71 tBu B8 2,6-F ₂ -Ph Viscous oil II-72 tBu B6 2,6- F ₂ -Ph 150.2-151.3 II-73 tBu CO ₂ nPr A2 Viscous oil II-74 tBu CO ₂ nBu A2 Viscous oil II-75 tBu B6 A13 Viscous oil II-76 tBu CO ₂ CH ₂ CCl ₃ A2 viscous oil II-77 tBu CO (2-Cl-Ph) A2 glassy II-78 tBu CO (3-CF ₃ -Ph) A2 glassy II-79 tBu CO (4-CF ₃ -Ph) A2 Glassy II-80 tBu CO (3-NO ₂ -Ph) A2 Glassy II-81 tBu CO (2-Cl-6-F-Ph) A2 Glassy II-82 tBu CO ₂ cPen 2,6-F ₂ -Ph vitreous II-83 tBu 3-Cl-pivaloyl A2 viscous oil ^* II-84 tBu CO ₂ iPr A2 viscous oil II-85 tBu CO ₂ CH ₂ CH ₂ Cl A2 viscous oil II- 86 tBu CO ₂ CHClCH ₃ A2 Viscous oil II-87 tBu COiPr A2 Viscous oil II-88 tBu Isonicotinoyl A2 Viscous oil II-89 tBu Picolinoyl A2 Viscous oil ────────────── ────────────────

[0051]

[Table 11] Table 2 (continued) ────────────────────────────── No. RBA mp (℃) ─── ─────────────────────────── II-90 tBu CO (4-Me-Ph) A2 Viscous oil II-91 tBu CO ( 4-NO ₂ -Ph) A2 viscous oil II-92 tBu Methacryloyl A2 viscous oil II-93 tBu B15 A2 glassy II-94 tBu PhCH ₂ A2 viscous oil II-95 tBu Me A2 136.5-138 II-96 tBu CBrF ₂ A2 84-86.5 II-97 tBu COnPr A2 Viscous oil II-98 tBu COiBu A2 Viscous oil II-99 tBu B43 A2 Glassy II-100 tBu PhCOCH ₂ A2 148-152 ^* II -101 tBu B42 A2 128-129.5 ^* II-102 tBu H A14 98-99 II-103 tBu H A16 Viscous oil II-104 tBu B7 A16 Viscous oil ^* II-105 tBu Cinnamoyl A2 Glassy II-106 tBu H A23 109-112 II-107 tBu B7 A23 120-122.5 II-108 tBu B7 A14 Viscous oil II-109 tBu B7 A14 Viscous oil ^{# 7} II-110 tBu COnC ₁₇ H ₃₅ A14 Viscous oil II-111 tBu PhCH ₂ CO A2 viscous oil ──────────────────────────────

[0052]

[Table 12] Table 2 (continued) ────────────────────────────── No. RBA mp (℃) ─── ─────────────────────────── II-112 tBu B7 A17 Viscous oil II-113 tBu H A17 140-143 II-114 tBu H A24 115-117 II-115 tBu CO ₂ iBu A24 Glassy II-116 tBu B7 A2 69.5-73.5 ^{# 8} II-117 tBu H A25 107-109 II-118 tBu B7 A25 Viscous oil II-119 tBu H A31 116-117 II-120 tBu CO ₂ (4-Me-Ph) A31 92-93 II-121 tBu H A26 133.2-135.4 II-122 tBu B7 A26 133.9-145 II-123 tBu H A27 46-47 II- 124 tBu H A28 168-169 II-125 tBu H A29 94.7-95.4 II-126 tBu B8 A29 Viscous oil II-127 tBu B8 A29 Viscous oil ^{# 9} II-128 tBu H A32 133.9-134.4 II-129 tBu H A33 220-230 II-130 2-6-F ₂ -Ph H 2,6-F ₂ -Ph 138-143 II-131 2-poly B7 A18 115-145 II-132 2-poly H A18 176- 178 II-133 2-Pyril H A9 191.5-195 ───────────────────── ────────

[0053]

[Table 13] Table 2 (continued) ────────────────────────────── No. RBA mp (℃) ─── ─────────────────────────── II-134 2-Polysil B7 A9 101-103 II-135 2-Polycil H A8 211-216 II -136 2-Polysil H A10 189-193 II-137 2-Polycil CO ₂ (4-F-Ph) A10 137-142 II-138 2-Polycil H A24 188-191.5 II-139 2-Polycil B7 A24 160- 163.5 II-140 2-poly B7 A30 123-125 II-141 2-poly H A30 165-166 II-142 2-poly H A13 149.5-151 II-143 NMePh H A7 161.5-164 II-144 NMePh B7 A7 120 -123 II-145 NMePh H A2 Glassy II-146 NMePh B7 A2 Glassy II-147 1-Phenyl B3 A2 165.5-169 II-148 1-Phenyl H A2 151-153 II-149 1-Phenyl H A7 187- 190 II-150 1-Phenyl B8 A7 Viscous oil II-151 1-Phenyl B8 A2 120-12 1.5 II-152 1-Phenyl B6 A2 Viscous oil II-153 1-Naphthyl H A2 161-163 II-154 1-Naphthyl B7 A2 Glassy II-155 1-Me-1-cHex H A2 Glassy ────────────────────────────

[0054]

[Table 14] Table 2 (continued) ────────────────────────────── No. RBA mp (℃) ─── ─────────────────────────── II-156 nPen H A2 73-75 II-157 tBu B8 A32 108-112 II-158 tBu H A1 Viscous oil II-159 1-Me-1-cHex B7 A2 Glassy II-160 nPen B7 A2 Glassy II-161 1-Me-1-cHex CH ₂ 0 (CH ₂ ) ₂ OCH ₃ A2 97- 98 ^* II-162 tBu B6 A13 104-107 ^* ────────────────────────────── *: E-form or Z-form, # 5: geometric isomer of II-40, # 6: geometric isomer of II-45, # 7: geometric isomer of II-108, # 8: geometric isomer of II-5, # 9: II-126 Geometric isomer of

Table 3

[0056]

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[0057]

[Table 15] ───────────────────────────── No. RBA mp (℃) ────────── ─────────────────── III-1 Ph B4 A1 Viscous oil ^* III-2 Ph B5 A1 40-41 ^* III-3 tBu B1 A1 151-152 ^* III-4 tBu B4 A1 77-79 ^* III-5 tBu B6 A2 55-61 ^* III-6 tBu B7 A2 Viscous oil ^* III-7 2-pentyl B1 A1 Viscous oil III-8 4-tBu- Ph B1 A5 viscous oil III-9 tBu Na A2 165-174 III-10 tBu B9 A2 viscous oil III-11 tBu B10 A2 185-186 ^* III-12 tBu B11 A2 viscous oil III-13 2 -NO ₂ -Ph B9 A1 168-171 ^* III-14 1-Naphthyl B9 A7 136-138 ^* III-15 tBu B7 A2 Viscous oil ^{# 10} III-16 Ph B4 A1 solid ^{# 11} III-17 tBu B4 A1 Viscous oil ^{# 12} III-18 2-Cl-6-F-Ph B7 A2 152-153 III-19 2,6-F ₂ -Ph B7 A2 Glassy * III-20 Ph B5 A1 105-107 ^{# 13} III-21 Ph B7 A2 Viscous oil ───────────────────────────── *: E-form or Z-form, # 10: II I-6 geometric isomer, # 11: III-1 geometric isomer # 12: III-4 geometric isomer, # 13: III-2 geometric isomer

Table 4

[0059]

Embedded image

[0060]

[Table 16] ────────────────────────────── No. GBA mp (℃) ───────── ───────────────────── IV-1 2-CF ₃ H A1 Viscous oil IV-2 3-CF ₃ H A1 159-163 IV-3 3 -CF ₃ B1 A1 174-175 IV-4 4-CF ₃ H A1 176-179 IV-5 4-CF ₃ B1 A1 viscous oil IV-6 2-CF ₃ CSNMe ₂ A1 viscous oil IV-7 3 (1-CN-1-Me) -Et H A1 Viscous oil IV-8 3 (1-CN-1-Me) -Et B1 A1 148-155 IV-9 3-OPh H A1 103-110 IV -10 3-OPh B7 A1 viscous oil IV-11 4-OPh H A1 148-150 IV-12 4-OPh B7 A1 viscous oil IV-13 4-Et H A1 148-149 IV-14 4- Et B7 A1 81-82 IV-15 4-Et B5 A1 Viscous oil IV-16 4-iPr H A1 126-127 IV-17 4-iPr B7 A1 105-106 IV-18 4-tBu H A1 117- 118 IV-19 4-tBu B1 A1 Viscous oil IV-20 4-OCF ₃ H A1 128-129 IV-21 4-OCF ₃ B7 A1 96-99 IV-22 3,4-Methylenedioxy H A1 129 -131 IV-23 3,4-Methylenedioxy B7 A1 Viscous oil ────────────────── ───────────

[0061]

[Table 17] Table 4 (continued) ────────────────────────────── No. GBA mp (℃) ─── ─────────────────────────── IV-24 4-tBu B7 A2 viscous oil IV-25 4-tBu B15 A2 viscous oil Material IV-26 4-tBu H A2 139-140 IV-27 4-tBu B7 A13 87-88 IV-28 4-tBu H A13 141-142 IV-29 4-tBu B8 A2 Glassy IV-30 4-tBu H A19 169.5-173 IV-31 4-tBu H A20 Glassy IV-32 4-tBu B7 A20 146-148 IV-33 4-tBu B15 A14 Viscous oil IV-34 4-tBu B7 A19 Glassy IV- 35 4-tBu B7 A1 Viscous oil ^* IV-36 4-tBu B8 A1 Viscous oil IV-37 4-tBu H A24 Glassy IV-38 4-tBu B8 A24 Glassy IV-39 4-tBu CO ₂ Et A1 viscous oil IV-40 4-tBu CO ₂ iBu A1 viscous oil IV-41 4-tBu COCO ₂ CH ₃ A1 viscous oil IV-42 4-sBu H A2 107-108 IV-43 4-sBu B15 A2 77-85 IV-44 4-iPr B15 A1 100-101 IV-45 4-iPr B15 A2 Viscous oil ─────────────────── ── ────────

[0062]

[Table 18] Table 4 (continued) ────────────────────────────── No. GBA mp (℃) ─── ─────────────────────────── IV-46 4-iPr H A2 98-99 IV-47 4-iPr B8 A2 Viscous oil IV-48 4-iPr CO (4-NO ₂ -Ph) A2 glassy IV-49 4-Et B15 A1 viscous oil IV-50 4-Ph H A1 glassy IV-51 4-PhH A2 glassy IV-52 4-Ph H A12 Glassy IV-53 4-Ph H A13 167-169 IV-54 3,4-Cl ₂ H A1 Glassy IV-55 4-Cl H A1 Glassy IV-56 2-F -4-CF ₃ H A2 Glassy IV-57 2-F-4-CF ₃ B7 A2 Glassy IV-58 2-F-4-CF ₃ B15 A2 Glassy IV-59 4-NO ₂ H A1 186- 188 IV-60 4-MeO H A1 108-110 IV-61 4-MeO B15 A1 Viscous oil ^* IV-62 4-iPrO H A1 127-131 IV-63 4-iPrO H A2 141.4-148.3 IV-64 4-iPrO B15 A1 viscous oil IV-65 4-iPrO B15 A2 viscous oil IV-66 4-iPrO B6 A2 viscous oil IV-67 4-nBuO H A1 101-104 ────── ──────────────── ───────

[0063]

[Table 19] Table 4 (continued) ────────────────────────────── No. GBA mp (℃) ─── ─────────────────────────── IV-68 4-nBuO B15 A1 75-70 IV-69 4-nBuO H A2 104.6-105.4 IV -70 4-nBuO B8 A1 77.1-80.7 IV-71 4-nBuO B15 A2 viscous oil IV-72 4-t-amyl B15 A2 viscous oil IV-73 4-allyloxy H A1 glassy IV-74 4 -Allyloxy B15 A1 Glassy IV-75 4- (Cl ₂ C = CHCH ₂ O) H A1 Glassy IV-76 4- (Cl ₂ C = CHCH ₂ O) B15 A1 Glassy IV-77 4- (ClCCCH ₂ O) H A1 Glassy IV-78 4-PhCH ₂ OH A1 152.9-154.7 IV-79 4-PhCH ₂ OH A2 189-190.5 IV-80 4-PhCH ₂ O B15 A2 123-129 IV-81 4-MeOCH ₂ OH A1 130.4-131.7 IV-82 4-CF ₃ CH ₂ OH A1 100-103 IV-83 4-Pyperroyl B15 A2 Glassy IV-84 4-Pyperroyl H A2 Glassy IV-85 4-Me ₂ NCO ₂ H A2 Glassy IV-86 4-Me ₂ NCO ₂ B15 A2 Glassy IV-87 4-Me ₂ NCO ₂ B7 A2 Glassy IV -88 4-tBu COCO ₂ Et A1 viscous oil IV-89 4-tBu CO ₂ iBu A2 viscous oil ─────────────────────── ───────

[0064]

[Table 20] Table 4 (continued) ────────────────────────────── No. GBA mp (℃) ─── ─────────────────────────── IV-90 4-tBu CO ₂ iBu A13 104-105 IV-91 4-tBu B3 A1 Viscous Oil IV-92 4-tBu B19 A1 Glassy IV-93 4-tBu CO (4-CO ₂ Me-Ph) A2 Glassy IV-94 4-tBu CO (4-CO ₂ Me-Ph) A13 Glassy IV-95 4-tBu B3 A2 71-72 * IV-96 4-CHF ₂ OH A2 glassy IV-97 4-CHF ₂ O B15 A2 glassy IV-98 4-CHF ₂ O B7 A2 glassy IV-99 4-CH ₃ CONH H A2 247.9-251.9 IV-100 4-CH ₃ CONH B7 A2 82.1-84.3 IV-101 4-CO ₂ Me H A2 151-152 IV-102 4-CO ₂ Me B7 A2 Viscous oil ^* IV-103 4-Hydinyl H A2 Glassy IV-104 4-tBu B15 A1 78-82 IV-105 4-tBu Methacryloyl A1 Viscous liquid ^* IV-106 4-tBu COCH = (CH ₃ ) ₂ A1 Viscous liquid IV-107 4-tBu B33 A1 Viscous liquid IV-108 4-tBu CH ₂ OCH ₂ Ph A1 Viscous liquid IV-109 4-tBu B24 A1 Viscous liquid IV-110 HH A1 48-49 IV-111 4- S Me H A2 154-156 ──────────────────────────────

[0065]

[Table 21] Table 4 (continued) ────────────────────────────── No. GBA mp (℃) ─── ─────────────────────────── IV-112 4-SMe B7 A2 Viscous liquid ^* IV-113 4-SOMe H A2 Glassy IV -114 4-tBu B33 A2 Viscous liquid IV-115 4-tBu B3 A13 111-112 ^* IV-116 4-tBu B7 A3 Viscous liquid IV-117 4-tBu B3 A3 Viscous liquid IV-118 4-tBu COCH ₂ (4-OMe-Ph) A1 117-121 IV-119 4-SO ₂ Me B7 A2 glassy ^* IV-120 4-SOMe B7 A2 glassy ^* IV-121 4-OCH ₂ Ph-3-Cl H A2 Glassy IV-122 4-iPrO-3-Cl H A2 Glassy IV-123 4-iBuO-3-Cl H A2 Glassy IV-124 4-tBu B8 A3 Viscous liquid IV-125 4-tBu B7 2 -Cl-4-CF ₃ - 90-91 Chiaso Bu Lumpur 5-yl ────────────────────────────── *: E body Or Z body

In the composition of the present invention, at least one of the acrylonitrile derivatives and at least one of the known compounds can be used as a mixture as it is. Usually, various inert liquids, solids, Alternatively, the active compound of the present invention is retained in a gaseous carrier, and if necessary, auxiliary agents such as surfactants, dispersants, fixing agents, stabilizers, propellants, smokers, fumigants, and formulations such as ULV agents It is convenient to use it in form.

Examples of the liquid carrier include water, alcohols (eg, methanol and ethanol), ketones (eg, acetone, methyl ethyl ketone), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), and fatty acids. Group hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate,
Butyl acetate, etc.), nitriles (acetonitrile, isobutyl nitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), acid amides (N, N-dimethylacetamide, N, N-dimethylformamide, etc.), halogenated hydrocarbons, etc.

[Formulation Examples] Next, formulation examples of the pesticidal composition containing the composition of the present invention as an active ingredient are shown, but the present invention is not limited thereto. In the following formulation examples, the composition of the present invention refers to a mixture of at least one acrylonitrile derivative and at least one known compound, and "parts" means parts by weight. Formulation Example 1 wettable powder 20 parts of composition of the present invention 76 parts of pyrophyllite 2 parts of sorbol 5039 2 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) Plex # 80D 2 parts (Synthetic hydrated silicic acid: trade name of Shionogi & Co., Ltd.) The above is uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 2 Emulsion 5 parts of composition of the present invention 75 parts of xylene 15 parts of N-methylpyrrolidone 15 parts of sorbol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry Co., Ltd. The above are mixed uniformly to form an emulsion.

Formulation Example 3 Suspension (Floable) 25 parts of the composition of the present invention 10 parts of Agrisol S-710 (Nonionic surfactant: trade name of Kao Corporation) 0.5 part of Lunox 1000C (anion Water-soluble surfactant: Toho Chemical Industry Co., Ltd.) Xanthan gum 0.2 part Water 64.3 parts After uniformly mixing the above, wet pulverization is performed to obtain a suspending agent.

Formulation Example 4 Granular wettable powder (dry flowable) 75 parts of the composition of the present invention 5 parts of Hytenol NE-15 (anionic surfactant: trade name of Daiichi Kogyo Seiyaku Co., Ltd.) Vanirex N10 Part (anionic surfactant: trade name of Nippon Paper Industries Co., Ltd.) Carplex # 80D 10 parts (synthetic hydrous silicic acid: trade name of Shionogi & Co., Ltd.) After uniformly mixing and grinding, a small amount of water was added. The mixture is kneaded with stirring, kneaded, granulated by an extrusion granulator, and dried to obtain a wettable powder.

Formulation Example 5 Granules 1 part of the composition of the present invention 50 parts of bentonite 49 parts of talc After uniformly mixing and pulverizing the above, a small amount of water was added, followed by stirring, mixing and kneading, and the mixture was extruded and granulated with a granulator. Granulate and dry to granules.

[Formulation Example 6] Powder 3 parts of the composition of the present invention 0.5 part of Carplex # 80 0.5 part (white carbon: trade name of Shionogi & Co., Ltd.) Clay 95 parts Diisopropyl phosphate 1.5 parts And pulverized into a powder.

When used, the above-mentioned wettable powder, emulsion, suspension and granular wettable powder are diluted 50 to 20,000 times with water to obtain an active ingredient of 0.005 to 50 per hectare (ha).
Sprinkle to reach kg.

[0075]

【Example】

[Test Examples] Next, the usefulness of the composition of the present invention as a pesticide will be specifically described in the following test examples. One example of the formulation and production method of the 5% emulsion used in the following Test Examples 1 to 4 is shown below.

[5% Emulsion] 3.3 parts of the compound of the present invention I-12 1.7 parts fenbutans oxide 1.7 parts 75 parts of xylene 15 parts 15 parts of N-methylpyrrolidone 5 parts of sorbol 2680 5 parts (Nonionic surfactant and anionic interface Mixture with activator: trade name of Toho Chemical Industry Co., Ltd.) The above was uniformly mixed to form an emulsion.

[Test Example 1] Insecticidal test against adult female spider mite (Ibaraki strain) with four kinds of acrylonitrile derivatives, ie, compounds I-1, II-5, II-31 and III-19 shown in Tables 1-4 4
Various known compounds, ie, phenisobromolate, propafos, dicophor, and fluazinam, were formulated into a 5% emulsion, and diluted with tap water containing 3,000-fold diluted Nitten (manufactured by Nissan Chemical Industries, Ltd.) as a spreading agent. Then, they were prepared singly or as a mixture to give a predetermined amount of the active ingredient to obtain a reagent.

The leaves of the kidney beans were punched out using a cork borer, and circular leaf disks having a diameter of 4 cm were prepared. The disc was placed on a wet filter paper, and 10 female female adults of the spider mite (Ibaraki strain) with reduced sensitivity to some drugs such as organophosphorus agents and dicophor were inoculated on the disc. Thereafter, each chemical was sprayed on the spider mites using a rotary spray tower (manufactured by Mizuho Rika Co., Ltd.) at 2.5 ml per leaf disk. The treated spider mite is kept in a constant temperature room at 25 degrees Celsius,
After 48 hours, the survival was determined, and the mortality was determined from the following formula based on the obtained result. The filter paper was kept moist throughout the test in order to prevent the leaf disks of the kidney from drying out. The test was performed in duplicate.

Mortality (%) = Number of dead insects / Number of test insects X100

[0080] From the mortality of each treatment concentration was determined median lethal concentration (LC ₅₀ value) based on probit method. Furthermore, the Sun & Johnson method (Journal of Economic Entomology, 1960, vol. 55, 88) which is usually used to determine the degree of synergistic effect (synergistic effect)
The synergistic coefficient was calculated using the equation of (Page 7). The synergistic coefficient is expressed by the following equation.

Coefficient of synergy = actual toxicity index of the admixture / theoretical toxicity index of the admixture × 100 In this case, if the acrylonitrile derivative is A and the known insecticide and / or acaricide is B, the actual toxicity of the admixture index = a dosage of LC ₅₀ / AB admixture LC ₅₀ X100 theoretical toxicity index of admixtures = (a agent toxicity index XAB% of agent a in admixture + B agents toxic index XAB in admixture of B
Agent% of) 100, however, LC ₅₀ of LC ₅₀ / B agent toxicity index of 100 B agent toxicity index of A agent (A agent) X1
00. A value of the synergistic coefficient greater than 100 indicates a higher synergistic effect, a value equal to 100 indicates an additive effect, and a value smaller than 100 indicates a higher antagonistic effect. Table 5 shows the test results.

Table 5 Insecticidal test on adult female spider mite (Ibaraki strain)

[0083]

[Table 22] ──────────────────────────────────── drug LC ₅₀ (ppm) synergists coefficient ─ ─────────────────────────────────── Compound I-1 51.2-Compound II-5 153.5 -Compound II-31 221.3-compound III-19 62.3-phenisobromolate 923.8-propafos 70.2-dicofol 601.5-fluazinam 499.6-compound I-1 + phenisopromolate 45 6.6 212.9 Compound II-5 + propaphos 71.2 135.3 Compound II-31 + dicofol 220.0 147.1 Compound III-19 + fluazinam 49.0 226.1 ─────────────────────────

[Test Example 2] Citrus red mite (Shiraoka strain)
Pot test against 3 kinds of acrylonitrile derivatives, that is, compounds I-12, IV-21, and IV-27 shown in Tables 1 to 4 and three kinds of known compounds, that is, fenbutane tin oxide, hexthiazox, and bifenthrin % Nitten (Nissan Chemical Industry Co., Ltd.)
) Was diluted with tap water containing) and prepared singly or in a mixture to give a predetermined amount of the active ingredient to obtain a reagent agent.

A 20-cm-diameter pot-planted Unshu mandarin orange was prepared, and red mites (Shiraoka strain) having reduced sensitivity to some drugs such as organophosphates were bred to an appropriate density in a greenhouse. Immediately before the application of the drug solution, the number of parasites of the mandarin red mite parasitizing each tangerine tree was investigated, and the composition of the present invention and a single agent of the control were applied. After air-drying, store the pot in a greenhouse, and on days 5 and 10 after spraying,
On the 20th, 30th, and 40th days, the number of citrus red mite parasites infesting each tangerine tree was investigated. Table 6 shows the results.

The control efficiency was calculated on the basis of the second equation. The closer the value is to 100, the higher the control effect.

Table 6 Pot test on Citrus red mites (Shiraoka strain)

[0088]

[Table 23] ──────────────────────────────────── Drug concentration Number of parasites / pot (ppm) Before spraying After 5 days After 10 days After 20 days After 30 days After 40 days Control efficiency ──────────────────────────────────── Compound I-12 200 105 0 0 25 49 123 85.3 Compound IV-21 200 132 0 0 13 56 82 91.0 Compound IV-27 200 65 0 3 25 63 163 69.3 Fenbutane oxide 100 111 23 12 8 18 58 91.6 Hexythia sox 10 73 31 11 51 20 2 94.5 Perphenthrin 10 89 20 18 11 33 52 88.2 Compound I-12 200 + 100 32 0 0 0 3 2 98.8 + Fenbutane oxide Compound IV-21 200 + 10 162 0 0 0 1 2 99.9 + Hexithia sox Compound IV-27 200 + 10 66 0 0 2 0 5 99.2 + Hibfensulin Untreated-52 88 121 135 205 113-─────────────────────── ─ ───────────

[Test Example 3] Insecticidal test against the third-instar larva of Japanese moth (susceptible strain) Four kinds of acrylonitrile derivatives, that is, compounds II-12, II-153, II-142 and I- shown in Tables 1-4
Six and four kinds of known compounds, that is, phentoate, acephate, cypermethrin, and pyrazophos were prepared in a 5% emulsion, and diluted with tap water containing 3,000-fold diluted Nitten (manufactured by Nissan Chemical Industries, Ltd.) as a spreading agent. , Alone or as a mixture to prepare a predetermined amount of the active ingredient to obtain a reagent.

The leaf pieces of cabbage were immersed in a chemical solution adjusted to a predetermined concentration for 20 seconds, air-dried, and then placed in a petri dish having a diameter of 7 cm. Seven third-stage larvae of the Japanese moth, which is highly sensitive to commonly used drugs, are added to each petri dish.
The animals were released head by head and stored in a constant temperature room at 25 degrees Celsius. Six days after the treatment, the life and death of the test insects were examined. The test was performed in four repetitions. Based on the obtained data, the LC ₅₀ value was calculated in the same manner as in Test Example 1, and the synergy coefficient was further calculated based on the LC ₅₀ value. Table 7 shows the results.

Table 7: Insecticidal tests on the third-instar larvae of the Japanese moth (susceptible strain)

[0092]

[Table 24] 薬 剤 Drug LC ₅₀ (ppm) synergistic coefficient ─化合物 Compound II-12 16.6-Compound II-153 20.1 -Compound II-142 32.0-compound I-6 11.6-phentoate 3.33-acephate 62.32-cypermethrin 2.09-pyrazophos 623.9-compound II-12 + phentoate 3.02 183.7 compound II-153 + acephate 22.0 138.2 Compound II-142 + cypermethrin 1.56 251.5 Compound I-6 + pyrazophos 8.80 258.8 ───────────────────

[Test Example 4] Insecticidal test against female adult peach aphid (Shiraoka strain) Four kinds of oxopropionitrile derivatives, namely,
Compounds I-53, I-23, II-26 and II shown in Table 4
I-17 and four known compounds, i.e., bamidthione, thiomethone, ethiophenecarb, and pyrazophos are formulated into a 5% emulsion, and a 3000-fold diluted nitrate (Nissan Chemical Industries, Ltd.) diluted water is used as a spreading agent. The mixture was diluted with water and prepared singly or as a mixture to give a predetermined amount of the active ingredient to obtain a reagent.

[0094] Cabbage leaves were punched with a cork borer to make leaf disks 3 cm in diameter. The disc was placed on a wet filter paper and spread on the bottom of a petri dish having a diameter of 3 cm, and five female peach aphids, which were less sensitive to drugs such as organophosphates, were inoculated thereon. After that, 2.5 ml of each chemical solution per leaf disk was sprayed on the peach aphid by a rotary spray tower (manufactured by Mizuho Rika Co., Ltd.).
And sprayed. The treated peach aphids were kept in a constant temperature room at 25 degrees Celsius, and their viability was determined after 48 hours. The filter paper was kept moist throughout the test to prevent the cabbage leaf disks from drying out.
The test was performed in four replicates. Based on the obtained data, the LC ₅₀ value was calculated in the same manner as in Test Example 1, and the synergy coefficient was calculated based on the LC ₅₀ value. The results are shown in Table 8.

Table 8 Momoka aphid (Shiraoka strain)
Insecticidal test for female adults

[0096]

[Table 25] 薬 剤 Drug LC ₅₀ (ppm) synergistic coefficient ─化合物 Compound I-53 28.3-Compound I-23 149.2 -Compound II-26 53.3-Compound III-17 36.7-Bamidione 342.3-Thiometon 251.1-Ethiophenecarb 173.3-Pyrazophos 151.3-Compound I-53 + bamidione 26.2 199.5 Compound I -23 + Thiometon 142.1 131.7 Compound II-26 + Ethiophenecarb 46.3 176.1 Compound III-17 + Pyrazophos 33.1 178.5} ─────────────────

[0097]

EFFECT OF THE INVENTION The composition of the present invention has excellent insecticidal and acaricidal activity against many pests and spider mites, and is effective for mammals,
Has little adverse effect on fish and beneficial insects.
Therefore, the composition of the present invention can provide a useful pest control agent.

Continued on the front page (51) Int.Cl. ⁶ Identification code FI A01N 43/78 A01N 43/78 Z 47/06 47/06 D

Claims (5)

[Claims] (1) Formula (1): [Wherein Q is a phenyl group optionally substituted with W or a 5-membered heterocyclic group optionally substituted with R (provided that
A thiazol-2-yl group, a thiazol-4-yl group,
It is selected from thiazol-5-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl and pyrazol-5-yl groups. A represents a 5-membered or 6-membered heterocyclic group optionally substituted with Y (provided that a thiazol-2-yl group, a thiazole-
4-yl group, thiazol-5-yl group, pyrazol-1
-Yl group, pyrazol-3-yl group, pyrazol-4-
It is selected from yl, pyrazol-5-yl, pyridin-2-yl, pyridin-3-yl and pyridin-4-yl. B represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and 2 to 2 carbon atoms.
4 alkoxyalkyl group, methoxyethoxymethyl group, tetrahydropyranyl group, trimethylsilyl group, C 1-4 alkylsulfonyl group, —SO ₂ CF ₃ , mono- or di-C 1-4 alkyl-aminosulfonyl group A phenylaminosulfonyl group, a mono- or di-alkyl having 1 to 4 carbon atoms, an aminothiocarbonyl group,
-COT ¹ , NT ² T ³ T ⁴ T ⁵ which is an alkali metal, alkaline earth metal or ammonium group, provided that when Q is a thiazol-2-yl group, B represents alkyl having 1 to 4 carbon atoms; group, an alkoxyalkyl group having 2 to 4 carbon atoms, methoxyethoxymethyl group, tetrahydropyranyl group, trimethylsilyl group, an alkylsulfonyl group having 1 to 4 carbon atoms, -SO ₂ CF _3, mono or di - 1 to 4 carbon atoms alkyl - aminosulfonyl group, a phenyl aminosulfonyl group, a mono- or di - C1-C4 alkyl - amino thiocarbonyl group, -COT ^1, an alkali metal, alkaline earth metal or an ammonium group N
Represents ^{T 2 T 3 T 4 T 5} , R and Y are each independently a halogen atom, a carbon number 1 to 6
Alkyl group, alkenyl group having 2 to 6 carbon atoms, 2 carbon atoms
-6 alkynyl group, C 1-6 haloalkyl group,
A halocycloalkyl group having 3 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms which may be substituted with an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, 1 carbon atom
To 4 haloalkoxy groups, an alkylsulfenyl group having 1 to 4 carbon atoms, an alkylsulfinyl group having 1 to 4 carbon atoms,
An alkylsulfonyl group having 1 to 4 carbon atoms, a nitro group, a cyano group, an amino group, a monoalkylamino group having 1 to 6 carbon atoms, a dialkylamino group having the same or different 1 to 6 carbon atoms, a benzyl group, a phenoxy group, A hydroxy group, a naphthyl group, an alkoxy-carbonyl group having 1 to 4 carbon atoms,
A phenyl group optionally substituted by X, a pyridyl group optionally substituted by X, a thienyl group optionally substituted by X, an alkoxyalkyl group having 2 to 4 carbon atoms and an alkyl having 2 to 4 carbon atoms Represents one or more substituents arbitrarily selected from carbonyl groups (however, when two or more substituents may be the same or different from each other), or represents two adjacent substituents 5-, 6 formed by
-Represents a 7- or 8-membered ring, W is a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, Haloalkoxy group, alkylsulfenyl group having 1 to 4 carbon atoms, alkylsulfinyl group having 1 to 4 carbon atoms, alkylsulfonyl group having 1 to 4 carbon atoms, haloalkylsulfenyl group having 1 to 4 carbon atoms, 1 to 1 carbon atoms
4, a haloalkylsulfinyl group having 1 to 4 carbon atoms, a haloalkylsulfonyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms,
C2-4 haloalkenyl group, C2-4 alkenyloxy group, C2-4 haloalkenyloxy group, C2-4 alkenylsulfenyl group, C2-4 alkenylsulfinyl Group, C2-4 alkenylsulfonyl group, C2-4 haloalkenylsulfenyl group, C2-4 haloalkenylsulfinyl group, C2-4 haloalkenylsulfonyl group, C2-2 4 alkynyl group, C2-4 haloalkynyl group, C2-4 alkynyloxy group, C2-4 haloalkynyloxy group, C2-4 alkynylsulfenyl group, C2 carbon atom Alkynylsulfinyl group having 2 to 4 carbon atoms, alkynylsulfonyl group having 2 to 4 carbon atoms, haloalkynylsulfenyl group having 2 to 4 carbon atoms, haloa having 2 to 4 carbon atoms · The Nils sulfinyl group, 2 carbon atoms
Haloalkynylsulfonyl group, NO ₂ , CN, formyl, alkoxycarbonyl group having 2 to 6 carbon atoms, alkylcarbonyl group having 2 to 6 carbon atoms, haloalkylcarbonyl group having 2 to 6 carbon atoms and 2 to 6 carbon atoms (Where the number of substituents is two or more, they may be the same or different from each other), and the number of the substituents is 1, 2 3,
T ¹ is an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, or a C 3 to 6 carbon atom which may be substituted with an alkyl group having 1 to 3 carbon atoms. Cycloalkyl group, carbon number 1
-C6 alkoxy group, C1-C6 monoalkylamino group, C1-C6 dialkyl-amino group, phenylamino group, phenyl group optionally substituted with Z, or Z-substituted T ² , T ³ , T ^4, and T ⁵ each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkyl having 1 to 3 carbon atoms. Represents a cycloalkyl group or a benzyl group having 3 to 6 carbon atoms which may be substituted with a group, or any two selected from T ² , T ³ , T ⁴ and T ⁵ together with a nitrogen atom Heterocyclic 5 optionally containing another heteroatom, oxygen, nitrogen or sulfur
-, 6-, 7- or 8-membered ring may be formed; X and Z are each independently a halogen atom,
4, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, an alkylsulfenyl group having 1 to 4 carbon atoms, an alkylsulfinyl group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms An alkylsulfonyl group having 1 to 1 carbon atoms
4, haloalkyl group, nitro group, cyano group, 1 to 1 carbon atoms
4 monoalkylamino groups, the same or different C1-4 dialkylamino groups, phenyl groups, benzyl groups, phenoxy groups, hydroxy groups and C1-4 alkoxy-carbonyl groups arbitrarily selected One or more substituents (however, when the number of the substituents is two or more, they may be the same or different from each other). And at least one of the active ingredient compounds of known insecticides, acaricides, and bactericides as active ingredients. Composition. 2. The method of claim 2, wherein the active ingredient of the known insecticide, acaricide, and fungicide is an organophosphorus compound, a pyrethroid compound, a carbamate compound, a benzoylphenylurea compound, a chlornicotyl compound, fipronil, tebufenozide, pyri. Proxifene, chlorofenapyr, triazuron, pymetrozine, diafenthiuron, dicofol, phenisobromolate, propargite, clofentezine, amitraz, fenbutane tin oxide, hexthiazox, pyridaben, ethoxyxazole, tebufenpyrad, pyrimidifen, fenpyroximate, dithiocarbamate Compounds, N-haloalkylthioamide compounds, halogenated aromatic compounds,
Quinone compounds, dicarboximide compounds, benzimidazole compounds, acylalanine compounds, strobilurin compounds, anilinopyrimidine compounds, triazole / imidazole compounds, pyrimidine compounds, morpholine compounds, organophosphate esters Compounds, antibiotics, organic copper, basic copper sulfate calcium, copper hydroxide sulfate, basic copper chloride, cupric hydroxide, fludioisinyl, quinoxaline, fluazinam, iminoctadine acetate, iminoctadine arbecil, carboxin,
Oxycarboxin, diflumetrim, spiroxamine, quinixifene, dietofencarb, tricyclazole, probenazole, pyroquilon, ferimzone,
The insecticidal, acaricidal and fungicidal composition according to claim 1, wherein the composition is at least one selected from carpropamide, flutranil, pencyclon, thifluzamide, flametopil, simoxanil, and inorganic sulfur. 3. Q is a thiazol-4-yl group which may be substituted with R or a thiazol-5-yl group which may be substituted with R, wherein R is a halogen atom, a carbon atom having 1 to 6 carbon atoms. An alkyl group, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms,
A haloalkyl group having 1 to 6 carbon atoms, a halocycloalkyl group having 3 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms which may be substituted with an alkyl group having 1 to 3 carbon atoms, An alkoxy group, a haloalkoxy group having 1 to 4 carbon atoms, an alkylsulfenyl group having 1 to 4 carbon atoms,
Alkylsulfinyl group having 1 to 4 carbon atoms, alkylsulfonyl group having 1 to 4 carbon atoms, nitro group, cyano group, amino group, monoalkylamino group having 1 to 6 carbon atoms, dialkylamino group having the same or different 1 to 6 carbon atoms , Benzyl group, phenoxy group, naphthyl group, alkoxy having 1 to 4 carbon atoms
A carbonyl group, a phenyl group optionally substituted with X,
One selected from a pyridyl group optionally substituted by X, a thienyl group optionally substituted by X, an alkoxyalkyl group having 2 to 4 carbon atoms and an alkylcarbonyl group having 2 to 4 carbon atoms Y is a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, and an alkylsulfenyl group having 1 to 4 carbon atoms. , Carbon number 1
Alkylsulfinyl group having 1 to 4 carbon atoms, alkylsulfonyl group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, nitro group, cyano group, monoalkylamino group having 1 to 4 carbon atoms, the same or different carbon atoms having 1 Dialkylamino group, phenyl group, benzyl group, phenoxy group, hydroxy group, alkoxyalkyl group having 2 to 4 carbon atoms, alkylcarbonyl group having 2 to 4 carbon atoms, and alkoxy-carbonyl group having 1 to 4 carbon atoms. The insecticidal / miticidal / fungicidal composition according to claim 2, which is one or more substituents arbitrarily selected from the group. 4. A pyrazol-1-yl group optionally substituted with R, a pyrazol-3-yl group optionally substituted with R, and a pyrazole-optional group substituted with R.
A 4-yl group or a pyrazol-5-yl group optionally substituted with R, wherein R is a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and 2 to 6 carbon atoms; An alkynyl group of
A haloalkyl group having 1 to 6 carbon atoms, a halocycloalkyl group having 3 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms which may be substituted with an alkyl group having 1 to 3 carbon atoms, An alkoxy group, a haloalkoxy group having 1 to 4 carbon atoms, an alkylsulfenyl group having 1 to 4 carbon atoms,
Alkylsulfinyl group having 1 to 4 carbon atoms, alkylsulfonyl group having 1 to 4 carbon atoms, nitro group, cyano group, amino group, monoalkylamino group having 1 to 6 carbon atoms, dialkylamino group having the same or different 1 to 6 carbon atoms , Benzyl group, phenoxy group, naphthyl group, alkoxy having 1 to 4 carbon atoms
A carbonyl group, a phenyl group optionally substituted with X,
One selected from a pyridyl group optionally substituted by X, a thienyl group optionally substituted by X, an alkoxyalkyl group having 2 to 4 carbon atoms and an alkylcarbonyl group having 2 to 4 carbon atoms Y is a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, and an alkylsulfenyl group having 1 to 4 carbon atoms. , Carbon number 1
Alkylsulfinyl group having 1 to 4 carbon atoms, alkylsulfonyl group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, nitro group, cyano group, monoalkylamino group having 1 to 4 carbon atoms, the same or different carbon atoms having 1 Dialkylamino group, phenyl group, benzyl group, phenoxy group, hydroxy group, alkoxyalkyl group having 2 to 4 carbon atoms, alkylcarbonyl group having 2 to 4 carbon atoms, and alkoxy-carbonyl group having 1 to 4 carbon atoms. The insecticidal / miticidal / fungicidal composition according to claim 2, which is one or more substituents arbitrarily selected from the group. 5. The insecticidal, acaricidal and fungicidal composition according to claim 2, wherein the acrylonitrile derivative is at least one member selected from the group consisting of the following compounds. Embedded image Embedded image