MXPA99007602A - Acrylonitrile compounds, process for their production and pesticides containing them - Google Patents

Abstract

Novel compounds useful as active ingredients of pesticides are disclosed. Acrylonitrile compounds of formula (I) or their salts, wherein Q is Qa, Qb, Qc or Qd, Y is=C(R4)- or=N-, R1 is alkyl, haloalkyl, etc., each of R2 and R3 is halogen, alkyl which may be substituted, alkenyl which may be substituted, etc., R4 is hydrogen, halogen, alkyl or haloalkyl, l is from 1 to 4, m is from 0 to 5, n is from 0 to 3, q is from 0 to 4, when 1 is 2 or more, a plurality of R2 may be the same or different, when each of m, n and q is 2 or more, a plurality of R3 may be the same or different.

Description

ACRILONITRIL COMPOUNDS, PROCEDURE FOR THEIR PRODUCTION AND PESTICIDES THAT CONTAIN THEM DESCRIPTIVE MEMORY The present invention relates to novel cryonitrile compounds, useful as active ingredients for pesticides. (1) The patents EP 104609A, EP 62238A and the patent of E.U.A. 4,469,688, respectively, disclose compounds similar to the compounds of the present invention, but such compounds and the compounds of the present invention are different in their chemical structures. (2) Patent EP 776879A discloses a process for producing an enol ether which literally covers a part of the compounds of the present invention, but in this publication, there is no specific exposure at all with respect to the groups of compounds of the invention. present invention. (3) Patents JP-A-60-11401 and JP-A-60-1 1452, respectively, set forth a-cyanoketone derivatives which literally cover a part of the compounds of the present invention, but in those publications, there is no no specific exposure at all with respect to the group of compounds of the present invention. (4) The patent of E.U.A. 3,337,565 discloses acrylonitrile derivatives which literally cover a portion of the compounds of the present invention, but in this publication, there is no specific exposure whatsoever with respect to the group of compounds of the present invention. (5) U.S. Patent 3,337,566 discloses acrylonitrile derivatives similar to the compounds of the present invention, but such derivatives and the compounds of the present invention are different in their chemical structures. (6) Patent WO97 / 40009 discloses similar ethylene derivatives to the compounds of the present invention, but the derivatives and compounds of the present invention are different in their chemical structures. (7) The Bulletin of the Societé Chimique de France, 1980, No. 3-4, p. 163-166, discloses 3- (4-chlorophenyl) -2-phenyl-3-ethoxyacrylonitrile, but this compound and the compounds of the present invention are different in their chemical structures. (8) The Journal of Chemical Research (Sypnoses), 1987, p. 78-79, exposes 2- (3,5-dimethoxyphenyl) -3- (2-methoxy-4-methylphenyl) -3-acetoxy-acrylonitrile and 2- (3,5-dimethoxyphenyl-3- (2,6-dimethoxy 4-methylphenyl) -3-acetoxy-acrylonitrile, but these compounds and the compounds of the present invention are different in their chemical structures The present inventors have conducted several studies to discover an excellent pesticide, paying attention to the acrylonitrile compounds and as a result have performed the present invention.

Specifically, the present invention provides an acrylonitrile compound of the following formula (I) or its salt: where Q is: Qa Qb Qc Qd Y is = C (R4) - or = N-, Rt is alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, alkynyl, haloalkyl, -C (= O) R5, -C (= S) R5, -S ( O) wR5 or -CH2R9, each of R2 and R3 is halogen, alkyl that can be substituted, alkenyl that can be substituted, alkynyl that can be substituted, alkoxy that can be substituted, alkenyloxy that can be substituted, alkynyloxy that can be substituted, substituted, alkylthio which may be substituted, alkylsulfinyl, which may be substituted, alkylsulfonyl which may be substituted, alkenylthio which may be substituted alkenylsulfinyl which may be substituted, alkenylsulfonyl which may be substituted, alkynylthio which may be substituted alkynylsulfinyl which may be substituted, alkynylsulfonyl which can be substituted, nitro, cyano, phenyl which can be substituted, phenoxy which can be substituted, phenylthio which can be substituted, phenylsulfinyl which can be substituted, phenylsulfonyl which can be substituted, benzyl which can be substituted, benzyloxy which can be substituted benzylthio which can be substituted, benzoyl which can be substituted, R 4 is hydrogen, halogen, alkyl or haloalkyl, R5, is alkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, alkoxy which may be substituted, alkenyloxy which may be substituted alkynyloxy which may be substituted, alkylthio which may be substituted alkenylthio which may be substituted, alkenylthio which can be substituted, cycloalkyl, cycloalkyloxy, cycloalkylthio which can be substituted, -N (R) R8, phenyl which can be substituted, phenoxy which can be substituted, phenylthio which can be substituted, benzyl which can be substituted, benzyloxy which can be substituted to be substituted, benzylthio which can be substituted, -J, -OJ or -SJ, each of R7 and R8 is hydrogen, alkyl or alkoxy, Rg is cyano, phenyl which can be substituted, phenoxy which can be substituted, phenylthio which can be substituted to be substituted, phenylsulfinyl which can be substituted, phenylsulfonyl which can be substituted, benzyl which can be substituted, benzyloxy which can be substituted, benzylthio which can be substituted, benzo which can be substituted, -J, -C (= O) R? 0, -C (= S) R10, -S (O) wR? o or trimethylsilyl, R10 is alkyl or alkoxy, J is a heterocyclic group of or 6 members containing from 1 to 4 heteroatoms and at least one type selected from the group consisting of O, S and N (the heterocyclic group can be substituted), I is from 1 to 4, m is from 0 to 5, n is from 0 to 3, q is from 0 to 4, w is from O to 2; when I is 2 or more, a plurality of R2 may be the same or different; when each m, n and q is 2 or more, a plurality of R3 can be the same or different, provided that the following compounds are excluded: (1) a compound in which Q is Qb, Y is = C (R4), -, and Ri is alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, -S (O) wRs or -CH2Rg. (2) a compound in which Q is Qb, Y is = C (R4) -, Rt is -C (= O) R5, and R5 is alkyl that can be substituted, alkenyl that can be substituted, alkynyl which can be substituted, alkoxy which may be substituted alkenyloxy which may be substituted, alkynyloxy which may be substituted, cycloalkyl, cycloalkyloxy, -N (R) Rβ, phenyl which may be substituted, phenoxy which may be substituted, phenylthio which may be substituted, benzyl which it can be substituted, benzyloxy which can be substituted benzylthio which can be substituted, -J, -OJ or -SJ, (3) a compound in which Q is Qb, Y is = C (R4) -, Ri is -C ( = S) R5, and R5 is -N (R) R8, (4) a compound in which Q is Qb or Qc, Y is = N-, Ri is alkyl or -C (= O) R5 and R5 is alkyl , (5) 3- (4-chlorophenyl) -2-phenyl-3-ethoxyacrylonitrile, (6) 2- (3,5-dimethoxyphenyl) -3- (2-methoxy-4-methylphenyl) -3-acetoxy-acrylonitrile, and (7) 2- (3,5-dimethoxyphenyl) -3- (2,6-dimethoxy-4-methylphenyl) -3-acetoxy-acrylonitrile; and a process for its production, a pesticide containing it and a novel intermediate compound useful for its production. In the formula (I), the substituent for the alkyl that can be substituted, the alkenyl that can be substituted, the alkynyl that can be substituted, the alkoxy that can be substituted, the alkenyloxy that can be substituted, the alkynyloxy that can be substituted substituted, the alkylthio which may be substituted, the alkylsulfinyl which may be substituted, the alkylsulfonyl which may be substituted, the alkenylthio which may be substituted, the alkenylsulfinyl which may be substituted, the alkennisulfonyl which may be substituted, the alkynylthio which may be substituted , the alkynylsulfinyl that can be substituted, and the alkynylsulfonyl that can be substituted, for each of R2 and R3 or the substituent for the alkyl that can be substituted, the alkoxy that can be substituted, the alkenyloxy that can be substituted, the alkynyloxy which can be substituted, the alkylthio which can be substituted, the alkenylthio which can be substituted and the alkynylthio which can be substituted, for R5, it can be, for example, halogen, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, amino, monoalkylamino, dialkylamino, nitro or cyano. The number of substituents may be one or more, and when it is more than one, and when it is more than one, a naturality of substituents may be the same or different. In addition, the substituent for the phenyl which can be substituted, the phenoxy which can be substituted, the phenylthio which can be substituted, the phenylsulfinyl which can be substituted, the phenylsulfonyl which can be substituted, the benzyl which can be substituted, the benzyloxy which can be substituted, it can be substituted, the benzylthio which can be substituted or the benzoyl which can be substituted, for each of R2 and R3, the substituent for the phenyl which can be substituted, the phenoxy which can be substituted, the phenylthio which can be substituted, the benzyl that can be substituted, the benzyloxy that can be substituted or the benzylthio that can be substituted, for R5, the substituent for the phenyl that can be substituted, the phenoxy that can be substituted, the phenylthio that can be substituted, the phenylsulfinyl which can be substituted, the phenylsulfonyl which can be substituted, the benzyl which can be substituted, the benzyloxy which can be substituted, the benzylthio which can be substituted or the benzoyl which can be substituted, for Rg, or the substituent for the heterocyclic ring for J, can be, for example, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro, cyano, -S (0) wR6, amino, monoalkylamino or dialkylamino. The number of substituents may be one or more and when it is more than one, a plurality of substituents may be the same or different. Here, Re is alkyl or haloalkyl, and w is 0 to 2. The heterocyclic group J can be, for example, furyl, thienyl, pyrrolyl, pyrazolyl, midazolilo, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, 1-pyrrolidinyl, 1-piperidinyl or 4-morpholino. Preferred compounds among the acrylonitrile compounds of the formula (I) or their salts are as follows. (A) The acrylonitrile compound or its salt, wherein Q is Qa, Qb or Qc, and each of R2 and R3 is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, cyano, phenyl which may be substituted by me, or phenoxy which may be substituted by me, R5 is alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, aminoalkyl, monoalkylaminoalkyl, dialkylaminoalkyl, alkenyl, haloalkenyl, alkynyl, halogenoalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alcoxicarbonilalquiltio alkenylthio, halogenoalqueniltio alkynylthio, halogenoalquiniltio, cycloalkyl, cycloalkylthio, -N (R7) R8, phenyl which may be substituted by Me, phenoxy which may be substituted by Me, phenylthio which may be substituted by Me, benzyl which may be substituted by Mi, benzylthio which can be substituted by Mi, pyridyl which can be substituted by Mi, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholino, pyridyloxy which can be its substituted by Mi or pyridylthio which can be substituted by Mi, Rg is cyano, phenyl which can be substituted by Mi, benzyloxy which can be substituted by M-, benzoyl which can be substituted by Mi, pyridyl which can be substituted by Mi, -C (= O) R- or -S (O) wR? Oo trimethylsilyl, Mi is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro, cyano, -S (O) wR6, amino, monoalkylamino or dialkylamino, and R6 is alkyl or haloalkyl. The number of substituents Mi can be one or more, if it is more than one, a plurality of M-i can be the same or different. (B) The acrylonitrile compound or its salt, wherein Q is Qa, Qb or Qc, and each of R2 and R3 is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, cyano , phenyl which may be substituted by M2, or phenoxy which may be substituted by M2, R5 is alkyl, haloalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, halogenoalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alcoxicarbonilalquiltio, alkenylthio, halogenoalqueniltio alkynylthio, halogenoalkynylthio, cycloalkyl, cycloalkylthio, -N (R7) R8, phenyl which can be substituted by M2, phenoxy which can be substituted by M2, phenylthio which can be substituted by M2, benzyl which can be substituted by M2, benzylthio which can be substituted per M 2, pyridyl which can be substituted by M 2, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholino, each of R 7 and R 8 is hydrogen or alkyl, R g is cyano, phenyl which can be substituted by M 2, benzyloxy q which can be substituted by M2, benzoyl which can be substituted by M2, pyridyl which can be substituted by M2, -C (= O) R- | 0 -S (O) wR? 0 or trimethylsilyl, M2 is halogen, alkyl, halogenoalkyl, alkoxy, haloalkoxy, nitro, cyano or S (O) wR6 »and Re, is alkyl. The number of substituents M2 may be one or more, and when it is more than one, a plurality of M2 may be the same or different. (c) The acrylonitrile compound or its salt, according to item (b) above, wherein Q is Qa or Qb. (d) The acrylonitrile compound or its salt, according to item (c) above, wherein Q is Qa. (e) The acrylonitrile compound of the above formula (I) or its salt, wherein Q is Qa or Qb, Y is = C (R4) -, and R4 is hydrogen. (f) The acrylonitrile compound or its salt, according to subsection (e) above, where Q is Qa. (g) The acrylonitrile compound or its salt, according to subsection (e) or (f) above, wherein R2 is halogen, alkyl or haloalkyl, and I is 1 to 3. (h) The acrylonitrile compound or its salt, according to subsection (e) or (f) above, wherein Ri is alkoxyalkyl, -C (= O) R5, -C (= S) Rs, -S ( O) wR5 or -CH2Rg, R2 is halogen, alkyl or haloalkyl, R3 is halogen or alkyl, R5 is alkyl, haloalkyl, alkoxyalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxycarbonylalkyl, alkenylthio, -N (R7) R8, phenyl it can be substituted by M3, phenoxy which can be substituted by M3, phenylthio which can be substituted by M3, benzyl which can be substituted by M3, pyridyl which can be substituted by M3, 1-pyrrolidinyl or 4-morpholino, each of R7 and R8 is hydrogen or alkyl, Rg is phenyl, M3 is halogen, alkyl or alkoxy, I is from 1 to 3, m is from 0 to 3, n is from 0 to 1, and w is from 1 to 2. The number of substituents M3 can be one or more, and when it is more than one, a plurality of M3 can be the same or different. (i) The acrylonitrile compound of the formula (I) or its salt, in which the formula (I) is the formula (1-1): wherein Q is Qa or Qb, R2 is halogenoalkyl, R2b is halogen, alkyl or haloalkyl, d is from 0 to 2, m is from 0 to 3, and n is from 0 to 1. When d is 2, two R2b can be same or different. (j) The acrylonitrile compound or its salt, according to item (i) above, wherein Q is Qa. (k) The acrylonitrile compound or its salt, according to subsection (i) above, where d is 0. (I) The acrylonitrile compound or its salt, in accordance with subsection (j) above, wherein d is 0. (m) The acrylonitrile compound or its salt, according to subsection (i), (j), (k) or (I) above, wherein Ri is alkoxyalkyl, -C (= O) Rs -C (= S) R5, -S (O) wR5 or -CH2Rg, R2 is halogen, alkyl or haloalkyl, R3 is halogen or alkyl, R5 is alkyl, haloalkyl, alkoxyalkyl, alkoxy, haloalkoxy , alkylthio, haloalkylthio, alkoxycarbonylalkylthio, alkenylthio, -N (R7) R8, phenyl which can be substituted by M3, phenoxy which can be substituted by M3, phenylthio which can be substituted by M3, benzyl which can be substituted by M3, pyridyl which it can be substituted by M3, 1-pyrrolidinyl or 4-morpholino, each R7 and R8 is hydrogen or alkyl, Rg is phenyl, M3 is halogen, alkyl or alkoxy, I is from 1 to 3, m is from 0 to 3, n is from 0 to 1, and w is from 1 to 2. In the compounds of the formula (I) or (a) to (m), the alkyl to the alkyl portion contained in Ri, R2, R2a, R2b, R3, 4 , Rs »Re, R7, Rs, R10, Mi, M2 or M3, can be, for example, an ac straight or branched DNA having 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, or hexyl. The alkenyl, the alkynyl, the alkenyl portion or the alkynyl portion contained in Ri, R2, R3 or R5, can be, for example, straight or branched chain having from 2 to 6 carbon atoms, such as vinyl, allyl , butadiene, isopropenyl, ethynyl, propynyl or 2-penten-4-enyl. The cycloalkyl or cycloalkyl portion contained in R5 may be, for example, one having from 3 to 6 carbon atoms, such as cyclopropyl, cyclopentyl or cyclohexyl. In the compounds of the formula (I) or (a) to (m), the halogen contained in Ri, R2, R2a, R2b, 3, R4 »Rd, M-i; M2, or M3, or the halogen as a substituent, can be fluorine, chlorine, bromine or iodine. The number of halogens as substituents may be one or more, and when more than one, a plurality of halogens may be the same or different. The acrylonitrile compound of the formula (I) is capable of forming a salt. Such salt can be any salt, as long as it is acceptable for agriculture. For example, it can be an inorganic salt such as a hydrochloride, a sulfate or a nitrate, or an organic salt such as an acetate or a methanesulfonate. The acrylonitrile compound of the formula (I) can have geometric isomers (E isomer and Z isomer). The present invention includes such isomers and mixtures thereof. The acrylonitrile compound of the formula (I) or its salt (hereinafter referred to simply as the compound of the present invention) can be produced, for example, by the sub-reactions (A) to ( C) and by a usual procedure to produce a salt.

[TO] (ll) Now, the reaction (A) will be described. In reaction (A), Q, Y, R-i, R, 1 and formula (I) are as defined above, and X is halogen. Reaction (A) is carried out usually in the presence of a base. As such base, one or more may suitably be selected for use, for example between alkali metals such as sodium and potassium; alkali metal alcoholates such as tertiary potassium butoxide; carbonates such as potassium carbonate and sodium carbonate; bicarbonates such as potassium bicarbonate and sodium bicarbonate; metal hydroxide such as potassium hydroxide and sodium hydroxide; metal hydrides such as potassium hydride and sodium hydride; and tertiary amines such as trimethylamine, triethylamine, pyridine and 4-dimethylaminopyridine. Reaction (A) can be carried out, if necessary, in the presence of a solvent. Such a solvent can be any solvent, provided that it is inert to the reaction. For example, one or more may suitably be selected for use, for example between aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; cyclic or non-cyclic aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran and diethyl ether; esters such as methyl acetate and ethyl acetate; dipolar aprotic solvents such as dimethylsulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone and pyridine; nitriles such as acetonitrile, propionitrile and acrylonitrile; ketones such as acetone and methyl ethyl ketone; tertiary amines such as dimethylamine and triethylamine; and water. For reaction (A), a catalyst such as 4-dimethylaminopyridine may be used as the case requires. The reaction temperature for reaction (A) is usually from -80 to + 150 ° C, preferably from -50 to + 120 ° C, and the reaction time is usually from 0.1 to 48 hours, preferably from 0.5 to 24 hours . In a case in which, in formula (I), R-i is methyl: [B] (II) + Diazomethane Reaction (B) will be described in detail. In reaction (B), Q, Y, R2, 1 and formula (II) are as defined above. The reaction (B) is carried out in the presence of a solvent. As such solvent, one may suitably be selected for use, for example aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; cyclic or non-cyclic aliphatic hydrocarbons such as carbon tetrachloride, menthyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran and diethyl ether; esters such as methyl acetate and ethyl acetate; nitriles such as acetonitrile, propinitrile and acrylonitrile; and acetones such as acetone and methylethylacetone. The reaction temperature for reaction (B) is usually 0 to 100 ° C, preferably 0 to 50 ° C, and the reaction time is usually 0.1 to 24 hours, preferably 0.1 to 12 hours. In the case in which, in formula (I), Ri is -C (= O) R5, -C (= S) Rs or -S (O) wR5: [C] The reaction (C) will be described. In reaction (C), Q, Y, R2, R5, 1 and formula (II) are as defined above, T is -C (= O) -, -C (= S) - or -S (O ) w-, G is hydrogen, Li, MgBr, MgCl or Mgl, and R, a is -C (= O) R5, -C (= S) R5 or -S (O) wR5 (where R5 and w are like they were previously defined). The first step in the reaction (C) is carried out, if necessary, in the presence of a base. As said base, one or more can be suitably selected for use of, for example, tertiary amines such as trimethylamine, triethylamine, pyridine and 4-dimethylaminopyridine. The first step of the reaction (C) is usually carried out in the presence of a solvent. Said solvent can be any solvent as long as it is inert to the reaction. For example, one or more may be suitably selected for use of, for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; cyclic or non-cyclic aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran and diethyl ether; and esters such as methyl acetate and ethyl acetate. The reaction temperature for the first step of the reaction (C) is usually from -80 to + 150 ° C, preferably from -50 to +80 ° C, and the reaction time is usually from 0.1 to 48 hours, preferably from 0.5 to 24 hours. The compound of the formula (V) prepared by the first step of the reaction (C) is a novel intermediate compound useful in the present invention. The second step of the reaction (C) is carried out, if necessary, in the presence of a base. As said base, one or more may suitably be selected for use of, for example, carbonates such as potassium carbonate and sodium carbonate; and tertiary amines such as trimethylamine, triethylamine, pyridine and 4-dimethylaminopyridine. The second step of the reaction (C) is usually carried out in the presence of a solvent. Said solvent can be any solvent as long as it is inert to the reaction. For example, one or more may be suitably selected for use of, for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; cyclic or non-cyclic aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran and diethyl ether; esters such as methyl acetate and ethyl acetate; nitriles such as acetonitrile, propionitrile and acrylonitrile; and ketones such as acetone and methyl ethyl ketone. The reaction temperature for the second step of the reaction (C) is usually from -80 to + 150 ° C, preferably from -80 to + 80 ° C, and the reaction time is usually from 0.1 to 48 hours, preferably from 0.5 to 24 hours. The compounds of the formula (11) in the reactions (A) to (C) above are useful intermediates for producing the compounds of the present invention, and novel compounds are included herein. The compound of the formula (II) can form a salt. Said salt can be any salt as soon as it is acceptable from the agricultural point of view. For example, it can be an inorganic salt such as a hydrochloride, a sulfate or a nitrate; an organic salt such as an acetate or a methanesulfonate; an alkali metal salt such as a sodium salt or a potassium salt; an alkaline earth metal salt such as a magnesium salt or a calcium salt; or a quaternary ammonium salt such as dimethylammonium or triethylammonium. The compound of the formula (II) has geometric isomers (isomer E and isomer 72). The present invention includes said isomers and mixtures thereof. The compound of the formula (II) can also be present in the form of tautomers represented by the following formula: The present invention includes said tautomers and mixtures thereof. In addition, the compounds of the formula (II) include those that exhibit pesticidal activities. The compound of the formula (II) or its salt can be prepared, for example, by the reactions (D) to (F), or by a conventional method to produce a salt.

[D] Q- CH2CN + r ^ R2) 1 (ll) (VII) [? C0Zl (HIV) The reaction (D) will be described. In reaction (D), Q, Y, R2, 1 and formula (II) are as defined above, and Z-i is alkoxy. The reaction (D) is usually carried out in the presence of a base and a solvent. As said base, one or more may suitably be selected for use of, for example, alkali metals such as sodium and potassium; alkali metal alcoholates such as sodium methylate, sodium ethylate and tertiary potassium butoxide; metal hydrides such as potassium hydride and sodium hydride; and organic lithium such as methyl lithium, butyllithium, tert-butyl lithium and phenyllithium. As the solvent, one or more may suitably be selected for use of, for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; ethers such as dioxane, tetrahydrofuran and diethyl ether; and alcohols such as methanol, ethanol, propanol and tert-butanol. The reaction temperature for reaction (D) is usually from -80 to + 150 ° C, preferably from -50 to + 120 ° C, and the reaction time is usually from 0.1 to 48 hours, preferably from 0.5 to 24 hours . In a case where in formula (II), Q is Qa: [E] First Step Second Step Hydrolysis The reaction (E) will be described in the following manner. In reaction (E), Qa, Y, R2 and I are as defined above, and Z2 is halogen. The first step of the reaction (E) is usually carried out in presence of a base. As said base, one or more may suitably be selected for use of, for example, alkali metals such as sodium and potassium; alkali metal alcoholates such as sodium methylate, sodium ethylate and tertiary potassium butoxide; carbonates such as potassium carbonate and sodium carbonate, bicarbonates such as potassium bicarbonate and sodium bicarbonate; metal hydroxides such as potassium hydroxide and sodium hydroxide; metal hydrides such as potassium hydride and sodium hydride; amines such as monomethylamine, dimethylamine and trimethylamine; and pyridines such as pyridine and 4-dimethylaminopyridine. The first step of the reaction (E) is carried out, if necessary, in the presence of a solvent. Said solvent can be any solvent as long as it is inert to the reaction. For example, one or more may be suitably selected for use of, for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; cyclic and non-cyclic aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran and diethyl ether; esters such as methyl acetate and ethyl acetate; dipolar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone and pyridine; ketones such as acetone and methyl ethyl ketone; amines such as monomethylamine, dimethylamine and triethylamine; and water. For the first step of the reaction (E), a catalyst such as 4-dimethylaminopyridine can be used, as the case requires. The reaction temperature for the first step of the reaction (E) is usually from -80 to + 150 ° C, preferably from -50 to + 120 ° C, and the reaction time is usually from 0.1 to 48 hours, preferably from 0.5 to 24 hours.

The compound of the formula (X) prepared by the first step of the reaction (E) is a novel intermediate compound useful in the present invention, and at the same time includes a compound thereof. Accordingly, the compound of the present invention can also be prepared by the first step of the reaction (E). The second step of the reaction (E) is a hydrolysis reaction, which is usually carried out in the presence of a base or an acid. As the base, one or more can be suitably selected for use of, for example, carbonates such as potassium carbonate and sodium carbonate.; metal hydroxides such as potassium hydroxide and sodium hydroxide; and amines such as monomethylamine, dimethylamine and triethylamine. As the acid, one or more can be suitably selected for use of, for example, inorganic acids such as hydrochloric acid and sulfuric acid; and organic acids such as acetic acid. The second step of the reaction (E) is carried out, if necessary, in the presence of a solvent. Said solvent can be any solvent as long as it is inert to the reaction. For example, one or more may be suitably selected for use of, for example, nitriles such as acetonitrile, propionitrile and acrylonitrile; alcohols such as methanol, ethanol, propanol and tert-butanol; organic acids such as acetic acid and propionic acid; aqueous ammonia; and water.

The reaction temperature for the second step of the reaction (E) is usually 0 to 100 ° C, preferably 0 to 50 ° C, and the reaction time is usually 0.1 to 48 hours, preferably 0.5 to 24 hours . In a case where in formula (II), Q is Qc: The reaction (F) will be described in the following manner. In reaction (F), Qc, Y, R2, 1 and formula (IX) are as defined above. The reaction (F) is carried out according to the first step of the reaction (E). Among the compounds of the formula (II) thus prepared, the following compounds are particularly useful and novel. The compounds of the formula (I l-1) or their salts: wherein Q, R2a, 2b and d are as defined above, provided that when Q is Qc, (1) q is not 0, or (2) R3 is not alkyl. Particularly preferred compounds between the compounds of the formula (1-1) are the following. (n) A compound of formula (ll-l) above, wherein Q is Qa or Qb, or salts thereof. (o) A compound of the formula (ll-l) above, wherein Q is Qa, or its salt. (p) A compound of the formula (ll-l) above, (n) u (o), wherein d is 0, or its salt. The compounds of the present invention are useful as active ingredients for pesticides. They are particularly useful as active ingredients of pesticides such as an insecticide, an acaricide, a nematicide, a soil pesticide, a fungicide and a marine anti-fouling agent. Preferred embodiments of pesticides containing the compounds of the present invention will now be described. First, pesticides such as an insecticide, an acaricide, a nematicide, a soil pesticide and a fungicide will be described. Pesticides containing the compounds of the present invention are useful as an insecticide, an acaricide, a nematicide and a soil pesticide (hereinafter referred to as agents for the control of insect pests), and are effective for the control of mites. phytoparasites such as: red spotted mite (Tetranychus urticae), red carmine mite (Tetranychus cinnabarinus), red kanzawa mite (Tetranychus kanzawai), red citrus mite (Panonychus citri), European red mite (Panonychus ulmi), broad mite Polyphagotarsonemus latus), pink mite of citrus rust (Aculops pelekassi) and mite of bulbs (Rhizoqlyphus echinopus); zooparasite mites such as Ixodes; aphids such as green peach aphid (Myzus persicae) and cotton aphid (Aphis gossypii); pests of agricultural insects such as diamond back moth (Plutella xylostella), cabbage soldier worm (Mamestra brassicae), common nocturnal caterpillar (Spodoptera litura), apple worm (Laspeyresia pomonella), corn and cotton worm (Heliothis zea), tobacco budworm (Heliothis virescens), lagarta (Lymantria dispar), rice leafroller (Cnaphalocrocis medinalis), Adoxophyes sp., Colorado potato beetle (Leptinotarsa decemlineata), leaf beetle of cucurbits ( Aulacophora femoralis), cotton boll weevil (Anthonomus grandis), brown grasshopper, leafhopper (Circulifer sp.), Coconuts, chinches, whiteflies, thrips, grasshoppers, antomid flies, beetles, black night caterpillar (Agrotis ipsilon), nocturnal caterpillar (Agrotis segetum) and ants; phytoparasitic nematodes such as root knot nematodes, cystic nematodes, root lesion nematodes, white tip of rice nematode (Aphelenchoides besseyi), strawberry stem nematode (Nothotylenchus acris), pine wood nematode (Bursaphelenchus lignicolus); gastropods such as slugs and snails; soil pests 6 such as isopods such as cochineals (Armadilidium vulgare, Porcellio scaber); hygienic insect pests such as tropical rat mite (Ornithonyssus bacoti), cockroaches, housefly (Musca domestica), and domestic mosquito (Culex pipiens); insect pests of stored grains such as moth angoumois of the grains (Sitotroga cerealella), adzuki bean weevil (Callosobruchus chinensis), red flour beetle (Tribolium castaneum) and mealworms; harmless domestic insect pests, such as cover-forming clothing moth (Tinea pellionella), black carpet beetle (Anthrenus scrophularidae) and subterranean termites; house mites such as mold mite (Tyrophaqus putrescentiae), Dermatophagoides farinae and Chelacaropsis moorei; and others such as fleas, lice and flies, which are parasites of, for example, domestic animals. Among them, agents for controlling insect pests containing the compounds of the present invention are particularly effective for the control of phytoparasitic mites, zooparasitic mites, agricultural insect pests, hygienic insect pests, harmless domestic insect pests, mites. , or similar. They are also effective against insect pests that show acquired resistance to organophosphorus, carbamate and / or synthetic pyrethroid insecticides. In addition, the compounds of the present invention have excellent systemic properties, and by their application for solid treatment, not only the control of harmful insects, noxious mites, noxious nematodes, noxious gastropods and noxious soil isopods, but also of pests of the foliage. In addition, the pesticides containing the compounds of the present invention are useful as fungicides. For example, they are effective for the control of diseases such as: ammunition shot (Pyricularia oryzae), pod blight (Rhizoctonia solani) and brown spot (Cochliobolus miyabeanus) against rice; ashtray (Erysiphe graminis), scab (Gibberella zeae), rust (Puccinia striiformis, P. coronata, P. graminis, P. recondite, P. hordei), snowy blight (Typhula sp., Micronectriella nivalis), flying coal (Ustilago tritici) , U. nuda), ocular spot (Pseudocercosporella herpotríchoides), foliar pustule (Septoria tritici) and pustule of the glumes (Leptosphaeria nodorum) against cereals; melanosis Diaporthe citri) and mange (Elsinoe fawcetti) against citrus fruits; blight of inflorescences (Sclerotinia mali), ashtray (Podosphaera leucotricha), pustule for Alternaria (Alternaria mali) and scabies (Venturia inaequalis) against apple trees; scabies (Venturia nashicola) and black spot (Alternaría kikuchiana) against pear trees; brown rot (Monilinia fructicola), scab (Cladosporium carpophilum) and rot by Phomopsis (Phomopsis sp.) against peaches; anthracnose (Elsinoe ampelina), mature rot (Glomerella cingulata), ash (Uncinula necator) and powdery mildew (Plasmopara viticola) against vines; anthracnose (Gloeosporium kaki) and angular leaf spot (Cercospora kaki) against Japanese persimmon; anthracnose (Colletotrichum lagenarum), ashtray (Sphaerotheca fuliginia), gummy stem blight (Mycosphaerella melonis) and downy mildew (Pseudoperonospora cubensis) against cucurbits; early blight (Alternaria solani), leaf mold (Cladosporium fulvum) and late blight (Phytophthora infestans) against tomatoes; leaf spot by Alternaria (Alternaria brassicae) against cruciferae; early blight (Alternaria solani) and late blight (Phytophthora infestans) against potatoes; ash (Sphaerotheca humuli) against strawberry; gray mold (Botrytis cinerea) and sclerotinial rot (Sclerotinia sclerotiorum) against several crop plants. In addition, they are also effective in controlling soil diseases caused by phytopathogenic fungi, such as Fusarium sp., Pythium sp., Rhizoctonia sp., Verticillium sp. and Plasmodiophora sp. Other preferred embodiments of the pesticides containing compounds of the present invention may be agricultural and horticultural pesticides, which collectively control the aforementioned phytoparasite mites, agricultural insect pests, phytoparasitic nematodes, gastropods, soil pests, various diseases and various diseases of the plant. floor. The pesticide, such as the insect pest control agent or the fungicide containing the compound of the present invention, is usually formulated by mixing the compound with various agricultural adjuvants., and is used in the form of a formulation such as a powder, granules, water-dispersible granules, a wettable powder, a suspension concentrate based on water, an oil-based suspension concentrate, water-soluble granules, an emulsifiable concentrate, a paste, an aerosol or an ultralow volume formulation. However, as long as it is suitable for the purpose of the present invention, it can be formulated in any type of formulation commonly used in this field. Said agricultural adjuvants include solid carriers such as diatomaceous earth, dead lime, calcium carbonate, talc, white carbon, kaolin, bentonite, a mixture of kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite and starch.; solventas such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, ciciohexano, dimethylsulfoxide, dimethylformamide, dimethylacetamide, n-methyl-2-pyrrolidone and alcohol; anionic and spreaders surfactants such as a fatty acid salt, a benzoate, one alkylsulfosuccinate a dialkylsulfosuccinate, a polycarboxylate, a salt of alkylsulfuric acid ester, an alkyl, one alquilarilsulfato, an ether sulfate alquildiglicol, a salt of ester alcoholsulfuric acid, an alkylsulfonate, an alkylarylsulfonate, an arylsulfonate, a ligninosulfonate, an alkyldiphenylether-disulfonate, a polystyrenesulfonate, an alkylphosphoric acid ester salt, an alkylarylphosphate, a styrylarphosphate, a polyoxyethylenealkylene ether sulfuric acid ester salt, a polyoxyethylene alkylarylesulfate, a ester salt polyoxyethylene alquilariletersulfúrico acid, polioxietilenalquileterfosfato, ester salt of polioxietilenalquilarilfosfórico acid and a salt of a condensate of naphthalene sulfonate formalin; nonionic and spreaders surfactants such as a fatty acid ester of sorbitan, an ester of fatty acid glycerin, a fatty acid polyglyceride a polyglycol ether fatty acid alcohol, acetylene glycol, acetilenalcohol, a block polymer oxyalkylene, an alkyl polyoxyethylene ether, an alkylaryl ether of polyoxyethylene, estirilarílico polyoxyethylene ether, an alkyl polyoxyethylene glycol ether, an ester of polyoxyethylene fatty acid ester, a polyoxyethylene sorbitan fatty acid ester, a fatty acid polyoxyethylene glycerin, hydrogenated polyoxyethylene castor oil and a polyoxypropylene fatty acid ester; and vegetable and mineral oils such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, oil of cottonseed, soybean oil, rapeseed oil, linseed oil, stick oil, and liquid paraffins. Said adjuvants may be selected for use among those known in the art, so long as the purpose of the present invention can be achieved in this manner. In addition, various additives that are commonly used can also be used, such as a filler, a thickener, an anti-settling agent, an antifreeze agent, a dispersion stabilizer, a phytotoxicity reducing agent and an antifungal agent. The weight ratio of the compound of the present invention to the different agricultural adjuvants is usually from 0.001: 99.999 to 95: 5, preferably from 0.005: 99.995 to 90:10. In the actual application of said formulation, it can be used as it is, or it can be diluted to a predetermined concentration with a diluent such as water, and various extenders can be added thereto, as the case requires. The application of the pesticide such as the agent for the control of insect pests or the fungicide containing the compound of the present invention can not be generally defined, since it varies depending on the climatic conditions, the type of formulation, the season of application , the application site or the types or degree of outbreaks of insect pests. However, it is usually applied with the concentration of the active ingredient being from 0.05 to 800,000 ppm, preferably from 0.5 to 500,000 ppm, and the dose per unit area is such that the compound of the present invention is from 0.05 to 10,000 g, preferably from 1. to 5,000 g, per hectare. The application of the agent for the control of insect pests as a preferred embodiment of the pesticide containing the compound of the present invention can not be generally defined, since it varies depending on various conditions as mentioned above, but is usually carried out being the concentration of the active ingredient from 0.1 to 500, 000 ppm, preferably from 1 to 100,000 ppm, and the dose per unit area is such that the compound of the present invention is from 0.1 to 10,000 g, preferably from 10 to 1, 000 g, per hectare. The application of the fungicide can not be generally defined, since it varies depending on various conditions as described above, but is normally carried out at a concentration of the active ingredient being from 0.1 to 500,000 ppm, preferably from 1 to 100,000 ppm, and the dose per unit area is such that the compound of the present invention is 0.1 to 10,000 g, preferably 10 to 1, 000 g, per hectare. Additionally, agricultural and horticultural pesticides as another preferred embodiment of pesticides containing the compounds of the present invention can be applied in accordance with the above-described application of insect and fungicide pest control agents. The present invention includes a method for controlling insect pests by such applications. Various pesticide formulations as insect or fungicide control agents containing the compounds of the present invention or their diluted compositions may be applied by conventional methods for application which are commonly used, such as aspersion (eg, spray, blast, spray). , atomization, dispersion or dispersion of dust or grain in water), ground application (eg, mixing or soaking), surface application (eg, coating, powder coating or coating) or impregnation to obtain poisonous food. In addition, it is possible to feed domestic animals with a food containing the above active ingredient and control the outbreak or growth of pests, particularly insect pests, with their droppings. Additionally, the active ingredient can also be applied by an application method called ultra low volume. In this method, the composition can be composed of 100% of the active ingredient.

Additionally, pesticides such as insect pests or fungicide control agents containing compounds of the present invention can be mixed with or used in combination with other chemicals, fertilizer or agricultural phytotoxicity reducing agents, whereby they can sometimes be obtained synergistic effects or activities. Such other agricultural chemicals include, for example, a herbicide, an insecticide, an insecticide against mites, a nematicide, an earth pesticide, a fungicide, an anti-virus agent, an attractant, an antibiotic, a phyto-hormone and a regulatory agent. plant growth. Especially, with a mixed pesticide having a compound of the present invention mixed with or used in combination with one or more active compounds of other agricultural chemicals, the scale of application, the time of application, the pesticide activities, etc. they can be improved to preferred addresses. The compound of the present invention and the active compounds of other agricultural chemicals can be formulated separately so that they can be mixed for use at the time of application, or they can be formulated together. The present invention includes a mixed pesticidal composition. The mixing ratio of the compound of the present invention to the active compounds of other agricultural chemicals generally can not be defined, because it varies depending on the weather conditions, the types of formulations, the time of application, the application site, the types or degrees of outbreaks of insect pests, etc., but is normally within a scale of 1: 300 to 300: 1, preferably 1: 100 to 100: 1, by weight. Additionally, the dose for the application is such that the total amount of the active compounds is from 0.1 to 5,000 g, preferably from 10 to 3,000 g, per hectare. The present invention includes a method for controlling insect pests by an application of a mixed pesticidal composition. The active compounds of insect pest control agents such as insecticides, insecticides against mites, nematicides, or soil pesticides in the other agricultural chemicals mentioned above, include, for example, (by common names, some of them are still in a application stage) organic phosphate compounds such as Profenofos, Dichlorvos, Fenamiphos, Fenitrothion, EPN, Diazinon, Chlorpyrifos-methyl, Acetate, Prothiophos, Fostiazato and Fosfocarb; carbamate compounds such as Carbaryl, Propoxur, Aldicarb, Carbofuran, Thiodicarb, Methomyl, Oxamyl, Etiofencarb, Pirimicarb, and Fenobucarb; nereistoxin derivatives such as Cartap, and Tiociclam; organic chlorine compounds such as Dicofol, and Tetradifon; organometallic compounds such as fenbutatin oxide; pyrethroid compounds such as Fenvalerate, Permethrin, Cypermethrin, Deltamethrin, Cihalotrin, Tefluthrin, and Etofenprox; Benzoylurea compounds such as Diflubenzuron, Clorfluazuron, Teflubenzuron, and Novaluron; juvenile hormone-like compounds such as Metoprene; pyridazinone compounds such as pyridaben; pyrazole compounds such as Fenpyroximate, Fipronil, and Tebufenpirad; neonicotinoids such as Imidacloprid, Nitenpyram, Acetamiprid, Diacloden, and Thiacloprid; hydrazine compounds such as Tebufenozide, Methoxyfenozide, and Chromafenozide; dinitro compounds; organic sulfur compounds; Urea compounds; triazine compounds; hydrazone compounds; and other compounds such as Buprofezin, Hexithiazox, Amitraz, Clordimeform, Silafluofen, Triazamate, Pymetrozine, Pirimidifen, Chlorfenapyr, Indoxacarb, Acequinocyl, Etoxazole, and Ciromacin. Additionally, BT agents, microbial agricultural chemicals such as insect viruses, or antibiotics such as Avermectin, Milbemycin and Spinosad, can be used in admixture or in combination. The active fungicide compounds among the other agricultural chemicals mentioned above include, for example, (by common names, some of which are still in the application stage) pyrimidinamine compounds such as Mepanipyrim, Pyrimethanil, and Cyprodinil; azole compounds such as Triadimefon, Bitertanol, Triflumizol, Etaconazole, Propiconazole, Penconazole, Flusilazole, Miclobutanil, Ciproconazole, Terbuconazole, Hexaconazole, cis-Furconazole, Prochloraz, Metconazole, Epoxiconazole, and Tetraconazole; quinoxaline compounds such as Quinomethionate; dithiocarbamate compounds such as Maneb, Zineb, Mancozeb, Polycarbamate, Propineb; organic chlorine compounds such as Phthaloate, Chlorothalonyl, and Quintocene; imidazole compounds such as Benomyl, Thiophanate-Methyl, Carbendazim, and 4-chloro-2-cyano-1-dimethylsulfamoyl-5- (4-methylphenyl) imidazole; pyridinamine compounds such as Fluazinam; cyanoacetamide compounds such as Cimoxanil; phenylamide compounds such as Metalaxyl, Oxadixyl, Ofurace, Benalaxyl, Furalaxyl, and Ciprofuram; sulfenic acid compounds such as Diclofluanide; copper compounds such as cuprous hydroxide, and copper oxine; ¡soxazole compounds such as hydroxyisoxazole; phosphorus organ compounds such as Fosetyl-AI, Tolcofos-Methyl, S-benzyl O, O-diisopropylphosphorothioate, O-ethyl S, S-diphenylphosphorodithioate, and aluminumethylhydrogen phosphonate; N-halogenothioalkyl compounds such as Captan, Captafol, and Folpet; dicarboximide compounds such as Procymidone, Iprodione, and Vinclozoline; benzanilide compounds such as Flutolanil, and Mepronil; piperazine compounds such as Triforin; pyrizine compounds such as Pirifenox; Carbinol compounds such as Fenarimol; and Flutriafol; piperidine compounds such as Fenpropidine; morpholine compounds such as Fenpropimorf; organotin compounds such as Fentin hydroxide, Fentin acetate; urea compounds such as Pencicuron; cinnamic acid compounds such as Dimetomorf; phenylcarbamate compounds such as Dietofencarbo; cyanopyrrole compounds such as Fludioxonil, and Fenpiclonil; β-methoxyacrylate compounds such as Azoxystrobin, Kresoxim-Methyl, and Methominofen; oxazolidinedione compounds such as Famoxadone; anthraquinone compounds; crotonic acid compounds; antibiotics; and other compounds, such as Isoprothiolane, Tricyclazole, Piroquilon, Diclomezine, Pro. benazole, Quinoxifen, Propamocarb hydrochloride and Spiroxamine. Next, pesticides as marine anti-pollution agents will be described. The marine anti-pollution agents containing the compounds of the present invention are effective in controlling harmful marine organisms against ships or subsea structures (such as bay structures, buoys, pipelines, bridges, subsea bases, oil well drilling facilities on the seabed, water pipes for power plants, fixed coast networks and farming networks). Specifically, these are effective to prevent the adhesion and spread of plants such as green algae and brown algae, animals such as persebe, cuttlefish, sea squirt, sea mussel and oyster, several bacteria called slime, and aquatic as mold and diatom. , in the lower part of the boats or on underwater structures. Marine anti-pollution agents containing the compounds of the present invention provide anti-pollution and anti-fouling properties over a prolonged period and exhibit excellent effects to prevent adhesion and propagation of harmful marine organisms to ships or underwater structures. The marine anti-pollution agents containing the compounds of the present invention are normally formulated and used in the form of paint compositions. However, they can be formulated and used in other forms (such as solutions, emulsifiable concentrates, or pellets) as the case requires. Paint vehicles to be used to formulate the compounds of the present invention in coating compositions can be resin vehicles that are commonly used. For example, a vinyl chloride resin, a vinyl chloride-vinyl acetate copolymer, a vinyl chloride-vinyl isobutyl ether copolymer, a chlorinated rubber resin, a chlorinated polyethylene resin, a chlorinated polypropylene resin, an acrylic resin, a styrene-butadiene resin, a polyester resin, an epoxy resin, a phenolic resin, a synthetic rubber, a silicone rubber, a silicone resin, a petroleum resin, an oil and fat resin, an ester rosin resin, a rosin soap or rosin can be mentioned. Additionally, as a vehicle having anti-pollution properties, an acrylic copolymer resin composition containing, as constituent units, an organotin compound salt of an unsaturated mono- or dicarboxylic acid, obtainable by an acid condensation reaction. (meta) acrylic with an organotin compound such as bis (tributyltin) oxide or triphenyltin hydroxide, or a resin that contains a metal element such as copper, zinc or tellurium in its side chains, can, for example, be used. When the compound of the present invention is formulated as a coating composition, the mixing ratio is adjusted so that the compound of the present invention will be contained in an amount of 0.1 to 60% by weight, preferably 1 to 40% by weight. weight, based on the total coating composition. The coating composition containing the compound of the present invention can be prepared using for example a ball mill, a rock mill, a roller mill or a sand wheel according to a method that is well known in the art the preparation of coating materials. Additionally, the aforementioned coating composition may contain a plasticizer, a coloring pigment, an extender pigment, an organic solvent, etc. which are commonly used in this field. The coating composition containing the compound of the present invention may additionally contain any other known organic or inorganic anti-pollution agent, as the case requires. Such an anti-pollution agent includes, for example, cuprous oxide, copper rhodanine, copper hydroxide, copper naphthenate, metallic copper and various tin compounds and dithiocarbamic acid derivatives, such as tetramethyltriurammonosulfide, tetramethyltriuramo disulfide, bis- (dimethyldithiocarbamate) ) of zinc, bis- (dithiocarbamate) of zinc ethylene, bis (dithiocarbamate) of manganese ethylene, and bis (dimethyl dithiocarbamate) of copper. As described above, the compound of the present invention or the compound of formula (II) as its intermediate, is effective as an active ingredient of a pesticide. Several modalities of it will be summarized as follows. (1) A pesticide containing a compound of the formula (I) or (II), or its salt, as an active ingredient, or a method for controlling pests using said compound. (2) An agricultural and horticultural pesticide containing a compound of the above formula (I) or (II), or its salt, as an active ingredient, or a method for controlling pests in an agricultural and horticultural field using said compound. (3) An insect pest control agent that contains a compound of the above formula (I) or (II), or its salt, as an active ingredient, or a method of controlling pests using said compound. (4) An insecticide containing a compound of the above formula (I) or (II), or its salt, as an active ingredient, or a method for controlling noxious insects using said compound. (5) An acaricide containing a compound of the above formula (I) or (II), or its salt, as active ingredients, or a method for controlling mites by using said compound. (6) A nematicide containing a compound of the above formula (I) or (II), or its salt, as an active ingredient, or a method of controlling nematodes by the use of said compound. (7) A soil pesticide containing a compound of the above formula (I) or (II), or its salt, as an active ingredient, or a method of controlling soil pests by using said compound. (8) A fungicide containing a compound of the above formula (I) or (II), or its salt, as an active ingredient, or a method of controlling fungi by using said compound. (9) A marine anti-pollution agent containing a compound of the above formula (I) or (II), or its salt, as an active ingredient, or a method for controlling marine contaminating organisms by the use of said compound. Next, the present invention will be described in further detail with reference to the examples. However, it should be understood that the present invention is not restricted in any way to such specific examples. First, examples will be described for preparing compounds of the present invention.

PREPARATION EXAMPLE 1 Preparation of β- (2-chlorophen.l) -β-isopropylcarbonyloxy-α- (2-thienyl-acrylonitrile (mentioned later as compound No. b-35) 1) 1.12 g of sodium were added to 25 ml of dry ethanol, followed by heating to a reflux temperature. Then a mixture consisting of 5.0 g of 2-thiopheneacetonitrile, 7.49 g of ethyl 2-chlorobenzoate and 25 ml of dry ethanol was added dropwise. After the completion of the dropwise addition, the mixture was reacted for 1 hour under reflux. After completion of the reaction, the reaction mixture was cooled and placed in water, and the aqueous layer washed with methylene chloride was acidified loosely with hydrochloric acid and extracted with methylene chloride. The obtained extracted layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 1.6 g of β- (2-chlorophenol) -β-hydroxy-a- (2-thienyl) acrylonitrile having a point. of fusion from 164 to 167 ° C. The NMR spectrum data of this compound were as follows. iH NMR dppm (Solvent, CDCL3 / 400 MHz) 6.54 (s, 1 H), 7.18 (dd, 1 H), 7.38-7.60 (m, 5H), 7.57 (dd, 1 H) 2) 46 mg of triethylamine were added to a mixture comprising 0.12 g of β- (2-chlorophenol) -β-hydroxy-a- (2-thienyl) acrylonitrile and 5 ml of dichloroethane, followed by cooling with ice. Then, a mixture comprising 54 mg of isobutyl chloride and 2 ml of dichloroethane was added dropwise. After completion of the dropwise addition, the mixture was returned to room temperature and reacted for 1.5 hours. After completion of the reaction, the reaction mixture was placed into water and extracted with methylene chloride. The extracted layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / N-hexane = 1/4) to obtain 0.12 g of the desired product having a melting point of 84 to 86 ° C. The NMR spectrum data of this product was as follows. iH NMR dppm (Solvent, CDCL3 / 400 MHz) 1.27 (d, 6H), 2.90 (m, 1 H), 7.11 (dd, 1 H), 7.33-7.40 (m, 2H), 7. 45 (d, 2H), 7.52 (d, 1 H), 7.65 (dd, 1 H).

PREPARATION EXAMPLE 2 Preparation of a- (2,4-dichlorophenyl) -β-ethylsulphonyloxy-β- (2-trifluoromethylphenyl) acrylonitrile (mentioned later as compound No. a-63) 1) A mixture comprising 3.7 g of 2-trifluoromethylbenzoyl chloride and 15 ml of toluene were added dropwise with stirring at room temperature to a mixture consisting of 3.0 g of 2,4-dichlorophenylacetonitrile, 45 ml of toluene, 1.63 g. g of triethylamine and 0.1 g of 4-dimethylaminopyridine. After completion of the dropwise addition, the mixture was reacted for 2 hours under reflux. After completion of the reaction, the reaction mixture was cooled, placed in water and extracted with methylene chloride. The obtained extracted layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 6.13 g of a- (2,4-dichlorophenyl) -β- (2-trifluoromethylphenyl) -β- (2 trifluoromethylbenzoyloxy) acrylonitrile. The NMR spectrum data of this compound were as follows: iH NMR dppm (Solvent, CDCLs / 400 MHz) 7.21 -7.45 (m, 3H), 7.49-7.88 (m, 8H). 2) 6.13 g of a- (, 4-dichlorophenyl) -β- (2-trifluoromethylphenyl) -β- (2-trifluoromethylbenzoyloxy) acrylonitrile obtained in the previous step were, without purification, dissolved in 90 ml of ethanol. A mixture comprising 0.69 g of sodium hydroxide and 12 ml of water was added thereto, and the mixture was reacted at room temperature for 2.5 hours. After completion of the reaction, the reaction mixture was placed into water, and the aqueous layer washed with methylene chloride was acidified loosely with hydrochloric acid and extracted with methylene chloride. The obtained extracted layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 2.5 g of a- (2)., 4-dichlorophenyl) -β-hydroxy-β- (2-trifluoromethylene) acrylonitrile (mentioned below intermediate No. II-4) having a melting point of 182 to 183 ° C. The NMR spectrum data of this compound were as follows: iH NMR dppm (Solvent, CDCL3 / 400 MHz) 5.81 (s, 1H), 7.38-7.48 (m, 2H), 7.54-7.65 (m, 1H), 7.66- 7.82 (m, 4H). 3) 0.118 g of ethanesulfonyl chloride were added under cooling with ice to a mixture comprising 0.30 g of a- (2,4-dichlorophenol) -β-hydroxy-β- (2-trifluoromethylphenyl) acrylonitrile, 7 ml of dichloroethane and 93 mg of triethylamine. The mixture was then returned to room temperature and reacted for 15 hours. After completion of the reaction, the reaction mixture was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / N-hexane = 1/4) to obtain 0.21 g of the desired product having a melting point of 114 to 116 ° C. The NMR spectrum data of this product were as follows: iH NMR dppm (Solvent, CDCL3 / 4OO MHz) 1.14 (t, 3H), 2.75-2.94 (m, 2H), 7.40 (dd, 1 H), 7.47 (d , 1 H), 7.57 (d, 1 H), 7.71-7.78 (m, 2H), 7.85-7.89 (m, 2H).

PREPARATION EXAMPLE 3 Preparation of α- (2,4-dichlorophenyl, β-methylsulfonyloxyhydroxy-β- (2-trifluoromethylphenyl) acrylonitrile, (mentioned later as compound No. a-55) 93 mg of triethylamine were added to a mixture consisting of 0.30 g of a- (2,4-dichlorophenyl) -β-hydroxy-β- (2-trifluoromethylphenyl) acrylonitrile and 7 ml of dichloroethane. Then, 96 mg of methanesulfonyl chloride was added thereto, and the mixture was reacted for 17 hours at room temperature. After completion of the reaction, the reaction mixture was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (development solvent: ethyl acetate / N-hexane = 1/6) to obtain 0.13 g of the desired oily product. The NMR spectrum data of this product were as follows: 1 H NMR dppm (Solvent, CDCL3400 MHz) 2.68 (s, 3H), 7.38 (d, 1 H), 7.46 (d, 1 H), 7.54 (s, 1 H ), 7.70-7.77 (m, 2H), 7.84-7.89 (m, 2H).

PREPARATION EXAMPLE 4 Preparation of α- (2,4-dichlorophenyl) -β- (n-propylsulfonyloxy) - β- (2-trifluoromethylphen-D-acrylonitrile (mentioned later as compound No. a-67) (Method 1) 93 mg of triethylamine was added to a mixture consisting of 0.30 g of a- (2,4-dichlorophenol) -β-hydroxy-β- (2-trifluoromethylene) -acylonitrile and ml of dicloloethane. Then, 0.13 g of n-propanesulfonyl chloride were added thereto, and the mixture was reacted for 15 hours at room temperature. After completion of the reaction, the reaction mixture was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (development solvent: ethyl acetate / n / hexane = 1/4) to obtain 0.15 g of the desired oily product. The NMR spectrum data of this product were as follows: iH NMR dppm (Solvent, CDCL3 / 400 MHz) 0.87 (t, 3H), 1.52-1.64 (m, 2H), 2.65-2.73 (m, 1 H), 2.79 -2.86 (m, 1 H), 7.40 (dd, 1 H), 7.47 (d, 1 H), 7.57 (d, 1 H), 7.71-7.78 (m, 2H), 7.85-7.89 (m, 2H) .

PREPARATION EXAMPLE 5 Preparation of - (2,4-dichlorophenyl) -β- (n-propylsulphonyloxy) -β- (2-trifluoromethylphen-D-acrylonitrile (mentioned later as compound No. a-67) (Method 2) 2. 22 g of triethylamine were added to a mixture consisting of 5.60 g of a- (2,4-dichlorophenyl) -β-hydroxy-β- (2-trifluoromethylphenyl) -acritronitrile and 50 ml of dichloroethane. Then a mixture consisting of 2.90 g of n-propanesulfonyl chloride and 10 ml of dichloroethane was added dropwise thereto. After completing the drip addition, the mixture was reacted for 2 hours at room temperature. After completion of the reaction, the reaction mixture was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (development solvent: ethyl acetate / n-hexane = 1/6) to obtain 2.8 g of the desired product with a melting point of 95 to 96 ° C.

EXAMPLE OF PREPARATION 6 Preparation of a- (4-chlorophenyl.-β- (n-butylsulfonyl) -? -. 2-trifluoromethylphenyl-acrylonitrile (mentioned later as compound No. a-156) 1) A mixture consisting of 6.19 g of 2-trifluoromethylbenzoyl chloride and 15 ml of toluene was added dropwise with stirring at room temperature to a mixture consisting of 3.0 g of chlorophenylacetonitrile, 30 ml of toluene, 3.0 g of triethylamine and 0.1 g of 4-dimethylaminopyridine. After completing the dropwise addition, the mixture was reacted for 8 hours under reflux.

After completion of the reaction, the reaction mixture was cooled, placed in water and extracted with methylene chloride. The obtained extracted layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 3.08 g of a- (4-chlorophenyl) -β- (2-trifluoromethylphenyl) -β- (2-trifluoromet L-benzoyloxy) acrylonitrile. 2) 3.08 g of a- (4-chlorophenyl) -β- (2-trifluoromethylphenyl) -β- (2-trifluoromethylbenzoyloxy) acrylonitrile obtained in the previous step was dissolved, without further purification, in 40 ml of ethanol. A mixture consisting of 0.50 g of sodium hydroxide and 10 ml of water was added thereto, and the mixture was reacted for 2 hours at room temperature.

After completion of the reaction, the reaction mixture was placed in water, and the aqueous layer which was washed with methylene chloride was acidified slightly with hydrochloric acid and extracted with methylene chloride. The extracted layer that was obtained was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 1.68 g of a- (4-chlorophenyl) -β- (hydroxy-β- (2- trifluoromethylphenyl) acrylonitrile (subsequently mentioned intermediate No. II-2) having a melting point of 146 to 148 ° C. The NMR spectrum data of this product are indicated below. 1 H dppm NMR (Solvent: CDCI./400 MHz) 7. 41 (d, 2H), 7.58-7.68 (m, 5H), 7.75 (m, 1 H) 3) 86 mg of triethylamine was added to a mixture consisting of 0.25 g of a- (4-chlorophenyl) -β-hydroxy-β- (2-trifluoromethylphenol) acrylonitrile and 8 ml of dichloroethane. Then, a mixture consisting of 0.133 g of n-butanesulfonyl chloride and 2 ml of dichloroethane was added dropwise thereto. After completing the dropwise addition, the mixture was reacted for 15 hours at room temperature.

After completion of the reaction, the reaction mixture was washed with water, and the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/6) to obtain 0.12 g of the desired product with a melting point of 63 to 64 ° C. The NMR spectrum data of this product are indicated below. 1 H dppm NMR (Solvent: CDCI3 / 400 MHz) 0. 78 (t, 3H). 1.25 (m, 2H), 1.58 (m, 2H), 2.78 (m, 2H), 7.45 (d, 2H), 7.63 (d, 2H), 7.72 (m, 2H), 7.82 (m, 2H) EXAMPLE OF PREPARATION 7 Preparation of a- (4-bromophenyl) -β- (ethylsulfonyloxy) -β- (2-trifluoromethylphenidacrylonitrile (mentioned later as compound No. a-21) 1) A mixture consisting of 17.55 g of 2-trifluoromethylbenzoyl chloride and 30 ml of toluene at room temperature was added dropwise with stirring to a mixture consisting of 15.0 g of 4-bromophenylacetonitrile, 120 ml of toluene, 8.52 g of triethylethylamine and 0.5 g of 4-dimethylaminopyridine. After completing the dropwise addition, the mixture was reacted for 4 hours under reflux.

Upon completion of the reaction, the reaction mixture was cooled, placed in water and extracted with methylene chloride. The extracted layer which was obtained was washed with water, dried under anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 21.25 g of a- (4-bromophenyl) -β- (2-trifluoromethyl) - β- (2-trifluoromethylbenzoyloxy) acrylonitrile. 2) 21.25 g of a- (4-bro? Mofenii) -β- (2-trifluoromethyl-phenyl)) -? - (2-trifluoromethylbenzoyloxy) acrylonitrile obtained in the previous step, without further purification, were dissolved in 60 ml of ethanol. Then, a mixture consisting of sodium hydroxide and 15 ml of water was added to it, and the mixture was reacted for 2 hours at room temperature.

Upon completion of the reaction, the reaction mixture was placed in water, and the aqueous layer which was washed with methylene chloride was acidified slightly with hydrochloric acid and extracted with methylene chloride. The extracted layer which was obtained was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 9.52 g of a- (4-bromophenyl) -β-hydroxy-β- (2-trifluoromethylphenyl) acrylonitrile (intermediary mentioned later No. II-3) having a melting point of 168 to 173 ° C. 3) 91 mg of triethylamine was added to a mixture consisting of 0.30 g of a- (4-bromophenyl) -β-hydroxy-β- (2-trifluoromethylphenyl) acrylonitrile and 8 ml of dichloroethane. Then, a mixture consisting of 0.1 1 g of ethanesulfonyl chloride and 2 ml of dichloroethane was added dropwise thereto.

After the addiction was finished dropwise, the mixture was reacted for 15 hours at room temperature.

After completion of the reaction, the reaction mixture was washed with water, and the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (developing solvent: ethyl acetate / n-hexane = 1/4) to obtain 0.14 g of desired product with a melting point of 131 to 132 ° C. The NMR spectrum data of this product was given as indicated below. 1 H dppm NMR (Solvent: CDCI3 / 400 MHz) 1. 23 (t, 3H), 2.85 (m, 2H), 7.56-7.62 (m, 4H), 7.71 (m, 2H), 7. 83 (m, 2H) EXAMPLE OF PREPARATION 8 Preparation of - (4-bromophenyl) -β- (n-propylsulfonyloxy) -β- (2-trifluoromethylphenylacrylonitrile (mentioned later as compound No. a-22) 60 mg of triethylamine was added to a mixture consisting of 0.20 g of - (4-bromophenyl) -β-hydroxy-β- (2-trifluoromethylphenyl) acrylonitrile and 6 ml of dichloroethane. Then, a mixture consisting of 77 mg of n-propanesulfonyl chloride and 2 ml of dichloroethane was added dropwise thereto.

After completing the addiction drop by drop, the mixture was reacted for 15 hours at room temperature.

After completion of the reaction, the reaction mixture was washed with water, and the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (development solvent: ethyl acetate / n-hexane = 1/9) to obtain 0.10 g of the desired oil product. The NMR spectrum data of this product are indicated below. 1 H dppm NMR (Solvent: CDCI3 / 400 MHz) 0. 86 (t, 3H), 1.65 (m, 2H), 2.76 (m, 2H), 7.56-7.63 (m, 4H), 7.71 (m, 2H), 7.81 (m, 2H) EXAMPLE OF PREPARATION 9 Preparation of - (4-bromophenyl) -β- (n-butylsulfonyloxy) -β- (2-trifluoromethylpheniPacrylonitrile (mentioned later as compound No. a-23) 60 mg of triethylamine was added to a mixture consisting of 0.20 g of a- (4-bromophenyl) -β-hydroxy-β- (2-trifluoromethylphenol) acrylonitrile and 6 ml of dichloroethane. Then, a mixture consisting of 85 mg of n-butanesulfonyl chloride and 2 ml of dichloroethane was added dropwise. After completing the addiction drop by drop, the mixture was reacted for 15 hours at room temperature.

After completing the reaction, the reaction mixture was washed with water, and the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (development solvent: ethyl acetate / n-hexane = 1/9) to obtain 70 mg of the desired oily product. The NMR spectrum data of this product are indicated below. 1 H dppm NMR (Solvent: CDCI3 / 400 MHz) 0. 78 (t, 3H), 1.23 (m, 2H), 1.59 (m, 2H), 2.78 (m, 2H), 7.57-7.63 (m, 4H), 7.71 (m, 2H), 7.82 (m, 2H) EXAMPLE OF PREPARATION 10 Preparation of a- (4-chlorophenyl) -β- (dimethylthiocarbamoyloxy) -β- (2-trifluoromethylphenyl, acrylonitrile (mentioned later as compound No. a-316) A mixed solution consisting of 0.42 g of dimethylthiocarbamoyl chloride and 5 ml of acetonitrile was added dropwise at room temperature to a mixed solution consisting of 1.0 g of a- (4-chlorophenyl) -β-hydroxy-β- (2-trifluoromethylphenyl) acrylonitrile, 0.47 g triethyl amine, a catalytic amount of 4-dimethylaminopyridine and 20 ml of acetonitrile. After completing the addiction drop by drop, the mixture was reacted for 2 hours at 50 ° C.

After completing the reaction, acetonitrile was distilled off under reduced pressure. Ethyl acetate and water were added to the residue to perform the extraction. The organic layer was washed with water and saturated with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off, and the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/4) to obtain 0.82 g of the desired product with a melting point of 137.9 ° C. The NMR spectrum data of the product are indicated below. 1 H dppm NMR (Solvent: CDCI3 / 400 MHz) 3. 10 (s, 3H), 3.22 (s, 3H), 7.35-8.15 (m, 8H) EXAMPLE OF PREPARATION 11 Preparation of a- (4-chlorophenyl) -β- (S-ethyldithiocarbonyloxy) -β- (2-trifluoromethylphenylacrylonitrile (mentioned later as compound No. a-306.

A mixed solution consisting of 500 mg of α- (4-chlorophenol) -β-hydroxy-β- (2-trifluoromethylphenyl) acrylonitrile and 2 ml of N, N-dimethylformamide was added dropwise under ice cooling to a mixture consisting of 68 mg of 60% sodium hydride and 10 ml of N, N-dimethylformamide. Upon completion of the dropwise addition, the mixture gradually returned to room temperature, and stirring was continued until the generation of hydrogen gas was completed. Then, the mixture was again cooled with ice, and a mixed solution consisting of 240 mg of ethyl chlorocarbonate and 2 ml of N, N-dimethylformamide was added dropwise. After completing the dropwise addition, the mixture was reacted for 2 hours at room temperature.

After completing the reaction, the reaction mixture was poured into 100 ml of ice water and then extracted with 150 ml of ethyl ether. The organic layer was washed with water and saturated with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. Then the solvent was distilled off, and the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/9) to obtain 380 mg of the desired product with a refractive index n_27'2 of 1.5612. The NMR spectrum data of this product are indicated below. 1 H dppm NMR (Solvent: CDCI3 / 400 MHz) 1. 29 (t, 3H, J = 7.80 Hz), 3.08 (q, 2H, J = 7.80 Hz), 7.01-7.93 (m, 8H) EXAMPLE OF PREPARATION 12 Preparation of a- (4-chlorophenyl) -β- (diethylaminosu.phoniloxy) -β- (2-trifluoromethylphenyl) -acrylonitrile (mentioned later as compound No. a-286) 0.18 g of triethylamine was added to a mixture consisting of 0.3 g of a- (4-chlorophenyl) -β-hydroxy-β- (2-trifluoromethylphenyl) acrylonitrile and 5 ml of dichloroethane. Then, 0.27 g of diethylsulfamoyl chloride was added thereto, and the mixture was reacted for 3 hours under reflux.

After completion of the reaction, water was placed in the reaction mixture and extracted with methylene chloride. The extracted organic layer was washed with water and dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the obtained residue was purified by gel column chromatography (developing solvent: ethyl, acetate / n-hexane = 15/85) to obtain 78 mg of the desired oil product. The NMR spectrum data of this product are indicated below. 1 H dppm NMR (Solvent: CDCI3 / 400 MHz) 1. 05 (t, 6H), 3.06 (m, 4H), 7.42 (d, 2H), 7.57 (d, 2H), 7.63-7.80 (m, 4H).

EXAMPLE OF PREPARATION 13 Preparation of a- (4-chlorophenyl) -β- (S-methyldithiocarbonyloxy) -β- (2-trifluoromethylphen-D-acrylonitrile (mentioned later as compound No. a-305) A mixed solution consisting of 800 mg of a- (4-chlorophenyl) -β-hydroxy-β- (2-trifluoromethylphenyl) acrylonitrile and 2 ml of N, N-dimethylformamide was added dropwise under ice-cooling to a mixture. which consists of 100 mg of 60% sodium hydride and 10 ml of N, N -dimethylformamide. After completing the dropwise addition, the mixture gradually returned to room temperature, and stirring was continued until the generation of hydrogen gas was completed, then the mixture was again cooled with ice, and a mixed solution consisting of 340 mg of methyl chlorodithiocarbonate and 2 ml of N, N-dimethylformamide was added dropwise thereto. After completing the dropwise addition, the mixture was reacted for 2 hours at room temperature.

After completing the reaction, the reaction mixture was poured into 100 ml of ice water. Then, 150 ml of ethyl ether was added thereto for extraction. The organic layer was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off, and the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/9) to obtain 610 mg of the desired product with a refractive index n ,. 39'4 from 1.5930. The NMR spectrum data of this product are indicated below. 1H dppm NMR (Solvent: CDCh / 400 MHz) 2. 47 (s, 3H), 2.53 (s, 3H), 7.70-7.99 (m, 8H) EXAMPLE OF PREPARATION 14 Preparation of - (4-chlorophenyl, -β- (2-trifluoromethyl) phenyl-acrylonitrile (mentioned later as compound No. a-218) 1.25 g of triethylamine was added to a mixture consisting of 2.0 g of a- (4-chlorophenol) -β-hydroxy-β- (2-trifluoromethylphenyl) -acritronitrile and 40 ml of dichloroethane. Then, 1.68 g of dimethylsulfamoyl chloride was added thereto, and the mixture was reacted for 2 hours under reflux.

After completion of the reaction, water was added to the reaction mixture and extracted with methylene chloride. The extracted organic layer was washed with water and dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the residue obtained was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 15/85) to obtain 2.50 g of the desired product having a melting point of 1 10 to 1 12 ° C. The NMR spectrum data of this product are indicated below. 1 H dppm NMR (Solvent: CDCI3 / 400 MHz) 2. 66 (S.6H), 7.43 (d, 2H), 7.60 (d, 2H), 7.67-7.82 (m, 4H) EXAMPLE OF PREPARATION 15 Preparation of a- (4-chlorophenyl) -β-ethyl-dithioxy-β- (2-trifluoromethyl-phenyl) -acrylonitrile (mentioned later as compound No. a-488) 1) 0.109 g of sulfur dichloride was added to a mixture consisting of 0.25 g of a- (4-chlorophenol) -β-hydroxy-β- (2-trifluoromethylphenyl) acrylonitrile and 10 ml of ethyl ether. Then, a mixture consisting of 67 mg of pyridine and 10 ml of ethyl ether was added thereto dropwise at a temperature of -10 ° C and the mixture returned to room temperature and reacted for 3 hours.

Upon completion of the reaction, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 0.30 g of - (4-chlorophenol) -β-chlorosulfenoxy-β- (2-trifluoromethylphenyl) acrylonitrile. 2) 0.30 g of a- (4-chlorophenyl) -β-chlorosulfenyloxy-β- (2-trifluoromethylphenyl) acrylonitrile obtained in the previous step, without further purification, were dissolved in 10 ml of dichloroethane. Then, 58 mg of ethanediol was added thereto, and then 94 mg of triethylamine was added thereto under cooling with ice. The mixture returned to room temperature and reacted for one hour.

Upon completion of the reaction, water was added to the reaction mixture and extracted with methylene chloride. The extracted organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (development solvent: ethyl acetate / n-hexane = 15/85 to obtain 0.20 g of the desired oily product.) The NMR spectrum data of this product are indicated to continuation. 1 H dppm NMR (Solvent: CDCI3 / 400 MHz) 1. 24 (t, 3H), 2.62-2.79 (m, 2H), 7.12 (d, 1 H), 7.43 (d, 2H), 7. 49 (t, 1 H), 7.60 (2d, 2H), 7.74 (d, 1 H) Now, typical examples of the compound of the present invention of the above formula (I) will be shown in tables 1-a, 1- b, 1-c and 1-d, and typical examples of the intermediate compound of formula (II) will be shown in table 2. These compounds can be synthesized in accordance with the preparation examples described above or the various methods described above to produce the compound of the present invention or its intermediate compound.

TABLE l-a TABLE l-a (continued) TABLE l-a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) SQUARE I- a (continued) TABLE I- a (continued) TABLE I a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I a (continued) TABLE l-a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE I- a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) 02 TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) TABLE l-a (continued) Table l-a (continued) Table l-a (continued) Table l-a (continued) Table l-a (continued) Table l-a (continued) TABLE l-b TABLE l-b (continued) TABLE l-b (Continued) TABLE l-b (Continued) TABLE l-b (Continued) TABLE l-c TABLE l-c (continued) TABLE l-c (continued) TABLE l-c (continued) TABLE l-c (continued) TABLE l-c (continued) TABLE l-d TABLE l-d (continued) TABLE l-d (continued) TABLE l-d (continued) TABLE 2 TABLE 2 (continued) TABLE 2 (Continued) TABLE 2 (Continued) TABLE 2 (continued) TABLE 2 (continued) TABLE 2 (continued) TABLE 2 (continued) Now, test examples will be described.

EXAMPLE OF TEST 1 Acaricide test against adults of two-spotted red mites (Tetranvchus urticae) An acaricidal solution was prepared to provide the concentration of a compound of the present invention at 800 ppm. A seedling of bean (Phaseolus vulgaris) with only one primary leaflet was transplanted into a cup (8 cm in diameter, 7 cm in height) and 30 adults of two spotted mites (Tetranychus urticae) were inoculated. The adult mites were immersed together with the primary bean leaflet in the above acaricide solution for approximately 10 seconds, then air dried and left in a constant temperature chamber at 26 ° C with illumination. On the second day after treatment, adult dead mites were counted, and mortality was calculated by the following equation.

Number of adult mites killed Mortality (%) x 100 Number of adults killed treated As a result, mortality was at least 90% with each of compounds No. a-6 to 7, a-10 to 14, a- 20 to 25, a-29, a-31, a-39, a-43, a-46 to 48, a-55, a-63, a-67, a-72, a-77 to 78, a- 80, a-83, a97, a-99, a-153, a-156, a-160 to 164, a-166 to 167, a-173, a-175 to 181, a-183 to 189, a- 191, a-194 a 197, a-200 a 202, a-206 a 207, a-209, a-21 1 a 212, a-214 a 215, a-218 a 221, a-223 a 224, a -227, a-230, a-240, a-244, a-245, a-250 a 251, a-254 a 258, a-260 a 263, a-267, a-274, a-286, a -288, a-290, a-298, a-300, a-303 a 308, a-310, a-316 a 319, a-322, a-323, a-325, a-328 a 329, a -331, a-335, a-342, a-359, a-360, a-362 a 363, a-365, a-367 a 368, a-371 a 373, a-375 a 376, a-381 , a-382, a-384, a-386 to 388, a-390, a-392, a-394 to 395, a-398, a-403, a-413 to 414, a-417 to 418, a -425 to 426, a-428 to 431, a-434 to 435, a-443, a-445, a-451 to 452, a-459 to 463, a-465 to 467, a-469 to 472, a -474, a-475, a-573, a-574, a-637 to 641, a-664 to 667, a-686, c-34, c-43 and c-44 and with intermediate No. II-2.

EXAMPLE OF TEST 2 Ovicide test against two-spotted red mite (Tetranychus urticae) An ovicidal solution was prepared to provide the concentration of a compound of the present invention at 800 ppm. A seedling of bean (Phaseolus vulgaris) with only one primary leaflet was transplanted into a cup (8 cm in diameter, 7 cm in height), and adult mites with two spots.

(Tetranychus urticae) were inoculated into it and allowed to oviposit for 24 hours, then adult mites were eliminated. The eggs were immersed together with the bean leaflet in the above ovicidal solution for approximately 10 seconds, then air dried and left in a constant temperature chamber at 26 ° C with illumination. On the seventh day after the treatment, the egg harvest was investigated and the ovicidal ratio was obtained by the following equation.

Number of dead eggs Ovicide ratio (%) = x 100 Number of eggs treated As a result, the ovicidal ratio was at least 90% with each of the compounds No. a-10 to 14, a-20 to 25, a-29, a-31, a-38 to 39, a-43, a-46 to 48, a-55, a-63, a-67, a-70, a-72, a-77 to 78, a-80, a-83, a-97, a-99, a- 150, a-156, a-160 to 164, a-166 to 168, a-173, a-175 to 181, a-183 to 189, a-191, a-194 to 197, a-200 to 202, a-204, a-206 a 207, a-209, a-21 1 a 212, a-214 a 215, a-218 a 221, a-223 a 224, a-227, a-230, a-233 to 234, a-240, a-244, a-245, a-250 to 251, a-254 to 258, a-260 to 262, a-267, a-274, a-282, a-286, a -288, a-298, a-300, a-303 a 308, a-310, a-316 a 319, a-322, a-323, a-325, a-328 a 329, a-331 a 333 , a-335, a-337, a-342, a-348, a-359, a-360, a-362 a 363, a-365, a-367 a 368, a-371 a 372, a-375 to 376, a-381, a-382, a-384, a-386 to 388, a-390, a-394 to 395, a-339, a-403, a-407, a-413 to 414, a -417 to 418, a-425 to 426, a-428 to 431, a-434 to 435, a-443, a-445, a-451, a-452, a-456, a-459 to 463, a -465 to 467, a-470 to 472, a-474, a-475, a-573, a-574, a-637 to 641, a-662 to 667, a-686, c-34, c-43 and c-44.

EXAMPLE OF TEST 3 Test of insecticide against small brown grasshopper (Laodelphax striatellus) The rice seedling was immersed for approximately 10 seconds in an insecticide solution prepared to bring the concentration of a compound of the present invention to 800 ppm, and then air dried. Then, the seedling with the root wrapped in a wet absorbent cotton was placed in a test tube. Then, 10 larvae of small brown grasshopper (Laodelphax striatellus) were released therein, and the test tube was covered with gauze and left in a constant chamber at 26 ° C with illumination. On the fifth day after the release, dead larvae were counted, and mortality was calculated by the following equation Number of dead insects Mortality (%) = _ x 100 Number of insects released As a result, mortality was at least 90% with each of compounds Nos. A-10 to 11, a-161, a-362, a-474, a-637, a-638 and c-34.

EXAMPLE TEST 4 Insecticidal test against the green aphid of the peach tree (Myzus persicae) An insecticidal solution was prepared to bring the concentration of a compound of the present invention to 800 ppm. The petiole of each one of the aubergines with a single leaf of the remaining foliage (planted in a container that has a diameter of 8 cm and a height of 7 cm) was covered with an adhesive, and about 2-3 females viviparous apterous Green peach aphid (Myzus persicae) were infested and incubated on the foliage leaf of the eggplant. After two days of the infestation, the adult insects were removed, and the number of larvae was counted. Afterwards, the foliage leaf of the eggplant infested with the larvae was immersed in the above insecticidal solution for approximately 10 seconds, then dried with air and left in a chamber of constant temperature at 26 ° C with illumination. On the fifth day after the treatment, dead insects were counted and mortality was calculated by the following equation: Number of dead insects Mortality (%) = x 100 Number of insects released Insects released from the leaf were counted as dead insects. As a result, the mortality was at least 90% with each of compounds Nos. A-10 to 11, a-160, a-162, a-637, and a-638.

EXAMPLE TEST 5 Test on the preventive effect against tomato late blight The tomato (variety: Ponderosa) was cultivated in a polyethylene container having a diameter of 7.5 cm. When the tomato reached the four-leaf stage, it was sprayed with 10 ml of a solution having a predetermined concentration of a compound of the present invention by means of a spray gun. After the solution was dried, the tomato plant was sprayed and inoculated with a suspension of zoesporangia of late blight fungi (Phytophtohora infestans) and kept in a constant temperature chamber at 20 ° C. From the third to the fourth day after the inoculation, the lesion area was examined, and the control index was determined in accordance with the following criteria for evaluation.

Control index Degree of disease outbreak (visual observation) 5 No lesion is recognized at all. 4 The area, number or length of injuries is less than 10% of that of the untreated site. 3 The area, number or length of the lesions is less than 40% of that of the untreated site. 2 The area, number or length of the lesions is less than 70% of that of the untreated site. 1 The area, number or length of the lesions is 70% or more of the untreated site.

As a result, compound number a-3 had a control index of 5 at a concentration of 250 ppm.

EXAMPLE PROOF 6 Proof of the preventive effect against wheatgrass The wheat (variety: Norin No. 61) was grown in a polyethylene container having a diameter of 7.5 cm. When the wheat reached a leaf stage of 1.5, it was sprayed with 10 ml of a solution having a predetermined concentration of a compound of the present invention by means of a spray gun. After the solution was dried, the wheat was sprinkled and inoculated with conidia of cenicilla fungi (Erysiphe graminis) and kept in a constant temperature chamber at 20 ° C.

On the eighth day after inoculation, the area of lesions or the area of the spore formation was examined, and the control index was determined in accordance with the following criteria for evaluation. control index Degree of disease outbreak (visual observation) 5 No injury or spore formation was recognized at all. 4 The area or number of lesions or the area of spore formation is less than 10% of that of the untreated site. 3 The area, number of lesions or spore formation area is less than 40% of that of the untreated site 2 The area, number of lesions or the area of spore formation is less than 70% of that of the site not treaty. 1 The area, number of lesions or area of spore formation is 70% or more of the untreated site.

As a result, compounds Nos. A-7, a-30, a-63, a-67, a-77 to 78, a-123 and a-234 had a control index of 5 at a concentration of 500 ppm and compounds Nos. a-3, a-38 to 39 and a-46 had a control index of 5 or 4 at a concentration of 250 ppm.

EXAMPLE TEST 7 Tests on the preventive effect against rust from the oat crown Oats (variety: Zenshin) was grown in a polyethylene container having a diameter of 7.5 cm. When the oat reached a stage of leaves of 1.5, it was sprayed with 10 ml of a solution having a predetermined concentration of a compound of the present invention by means of a spray gun. After the solution dried, oats were sprayed and inoculated with a suspension of fungal spores of crown rust (Puccinia coronata). On the eighth day after the inoculation, the lesion area or the spore formation area was examined and the control index was determined in the same manner as the test example 6. As a result, compounds Nos. A-78, a -123 and a-166 had a control index of 5 at a concentration of 500 ppm and compound No. a-3 had a control index of 5 at a concentration of 250 ppm.

EXAMPLE TEST 8 Control test against green algae The green algae cultured preliminarily for 7 days (F selenastrum capricornutum or © Chiorella vulgaris) were inoculated into an algal culture medium containing a solution prepared to bring the concentration of a compound of the present invention to 100 ppm, and allowed to stand for 8 days in a chamber of constant temperature at 20 ° C with illumination, where the degree of growth of green algae was investigated, and the control index was determined in accordance with the following criteria for evaluation.

Control index Degree of growth (visual observation) A No growth of green algae was observed at all. B There is a slight growth of green algae C The growth of green algae is observed to the same degree as the untreated site.

As a result, compounds Nos. A-3, a-6 and a-70 showed an A control index against green algae at a concentration of 100 ppm. In addition, against green algae, compounds Nos. A-3, a-6, a-26 and a-39 showed a control index of A at a concentration of 100 ppm. Next, the formulation examples will be described.

EXAMPLE OF FORMULATION 1 (a) Compound No a-31 20 parts by weight (b) Clay 72 parts by weight (c) Sodium ligninsulfonate 8 parts by weight The above components are mixed uniformly to obtain a wettable powder.

EXAMPLE OF FORMULATION 2 (a) Compound No. b-26 5 parts by weight (b) Talcum 95 parts by weight The above components mix uniformly to obtain a powder.

EXAMPLES OF FORMULATION 3 (a) Compound No a-39 20 parts by weight (b) N.N'-dimethylacetamide 20 parts by weight (c) Polyoxyethylene-alkylphenyl ether 10 parts by weight (d) Xylene 50 parts by weight 56 The above components are uniformly mixed and dissolved to obtain an emulsifiable concentrate.

EXAMPLE OF FORMULATION 4 (a) Clay 68 parts by weight (b) Sodium ligninsulfonate 2 parts by weight (c) Polyoxyethylenealkylaryl sulphate 5 parts by weight (d) Fine silica powder 25 parts by weight A mixture of the above components is mixed with the compound No. b-31 in a weight ratio of 4: 1 to obtain a wettable powder.

EXAMPLE OF FORMULATION 5 (a) Compound No. b-35 50 parts by weight (b) Polyalkylphenylphosphate-triethanolamine oxylated 2 parts by weight (c) Silicone 0.2 parts by weight (d) Water 47.8 parts by weight The above components are uniformly mixed and pulverized to obtain a base liquid, and (e) Sodium polycarboxylate 5 parts by weight (f) Anhydrous sodium sulfate 42.8 parts by weight are added, and the mixture is uniformly mixed and dried to obtain water dispersion granules.

EXAMPLE OF FORMULATION 6 (a) Compound No b-48 5 parts by weight (b) Polyoxyethylene-octylphenyl ether 1 part by weight (c) Polyoxyethylene phosphoric acid ester 0.1 part by weight (d) Calcium carbonate in granules 93.5 parts by weight The above components ( a) to (c) are uniformly mixed preliminarily and diluted with an adequate amount of acetone, and then the mixture is sprayed into component (d), and the acetone is removed to obtain granules.

EXAMPLE OF FORMULATION 7 (a) Compounds No. a-47 2.5 parts by weight (b) N-methyl-2-pyrrolidone 2.5 parts by weight (c) Soybean oil 95.0 parts by weight The above components are mixed uniformly and dissolved to obtain an ultra low volume formulation.

EXAMPLE OF FORMULATION 8 (a) Compound No. a-55 5 parts by weight (b) N.N'dimethylacetamide 15 parts by weight (c) Polyoxyethylenealkylaryl ether 10 parts by weight (d) Xylene 70 parts by weight The above components are mixed uniformly to obtain an emulsifiable concentrate

Claims (25)

NOVELTY OF THE INVENTION CLAIMS

1. - An acrylonitrile compound of the following formula (I) or its salt: where Q is: Qa Qb Qc Qd Y is = C (R4) - or = N-, Ri is alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, -C (= O) R5, -C (= S) R5, -S ( O) wR5 or -CH2R9, each of R2 and R3 is halogen, alkyl that can be substituted, alkenyl that can be substituted, alkynyl that can be substituted, alkoxy that can be substituted, alkenyloxy that can be substituted, alkynyloxy that can be substituted, substituted, alkylthio which may be substituted, alkylsulfinyl, which may be substituted, alkylsulfonyl which may be substituted, alkenylthio which may be substituted alkenylsulfinyl which may be substituted, alkenylsulfonyl which may be substituted, alkynylthio which may be substituted, alkynylsulfinyl which may be substituted, alkylsulfonyl which can be substituted, nitro, cyano, phenyl which can be substituted, phenoxy which can be substituted, phenylthio which can be substituted, phenylsulfinyl which can be substituted, phenylsulfonyl which can be substituted or, benzyl which can be substituted, benzyloxy which can be substituted benzylthio which can be substituted, benzoyl which can be substituted, R 4 is hydrogen, halogen, alkyl or haloalkyl, R 5, is alkyl which can be substituted, alkenyl which can be substituted, alkynyl which can be substituted, alkoxy which can be substituted, alkenyloxy which can be substituted alkynyloxy which can be substituted, alkylthio which can be substituted alkenylthio which can be substituted, alkynylthio which can be substituted, cycloalkyl, cycloalkyloxy, cycloalkylthio which can be substituted, -N (R7) R8, phenyl which can be substituted, phenoxy which can be substituted, phenylthio which can be substituted, benzyl which can be substituted, benzyloxy which can be substituted, benzylthio which can be substituted, -J, -OJ or - SJ, each of R and Rs is hydrogen, alkyl or alkoxy, Rg is cyano, phenyl which can be substituted, phenoxy which can be substituted, phenylthio which can be substituted or, phenylsulphinyl which can be substituted, phenylsulfonyl which can be substituted, benzyl which can be substituted, benzyloxy which can be substituted, benzylthio which can be substituted, benzoyl which can be substituted, -J, -C (= O) R? 0 , -C (= S) R? 0, -S (O) wR? Oo trimethylsilyl, R10 is alkyl or alkoxy, J is a 5- or 6-membered heterocyclic group containing from 1 to 4 heteroatoms and at least one type selected from the group consisting of O, S and N (the heterocyclic group can be substituted), I is from 1 to 4, m is from 0 to 5, n is from 0 to 3, q is from 0 to 4, w is from 0 to 2; when I is 2 or more, a plurality of R2 may be the same or different; when each m, n and q is 2 or more, a plurality of R3 can be the same or different, provided that the following compounds are excluded: (1) a compound in which Q is Qb, Y is = C (R4), -, and Ri is alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, -S (O) wRs or -CH2R9. (2) a compound in which Q is Qb, and is = C (R4) -, Ri is -C (= O) R5, and R5 is alkyl that can be substituted, alkenyl that can be substituted, alkynyl which can be substituted, alkoxy which may be substituted alkenyloxy which may be substituted, alkynyloxy which may be substituted, cycloalkyl, cycloalkyloxy, -N (R7) R8, phenyl which may be substituted, phenoxy which may be substituted, phenylthio which may be substituted, benzyl which it can be substituted, benzyloxy which can be substituted benzylthio which can be substituted, -J, -OJ or -SJ, (3) a compound in which Q is Qb, Y is = C (R4) -, R1 is -C ( = S) R5, and R5 is -N (R7) R8I (4) a compound in which Q is Qb or Qc, Y is = N-, R1 is alkyl or -C (= O) R5 and R5 is alkyl, (5) 3- (4-chlorophenyl) -2-phenyI-3-ethoxyacrylonitrile, (6) 2- (3,5-dimethoxyphenyl) -3- (2-methoxy-4-methylphenyl) -3-acetoxy-acrylon trill, and (7) 2- (3,5-dimethoxyphenyl) -3- (2,6-dimethoxy-4-methylphenyl) -3-acetoxy-acrylonitrile.

2. The acrylonitrile compound or its salt according to claim 1, characterized in that the substituent for the alkyl that can be substituted, the alkenyl that can be substituted, the alkynyl that can be substituted, the alkoxy that can be substituted, alkenyloxy which may be substituted, alkynyloxy which may be substituted, alkylthio which may be substituted, alkylsulfinyl which may be substituted, alkylsulfonyl which may be substituted, alkenylthio which may be substituted, alkenylsulfinyl which may be substituted, alkenesulfonyl which can be substituted, the alkyllithium which can be substituted, the alkylsilylfinyl which can be substituted, and the alkynylsulfonyl which can be substituted, for each of R2 and R3 or the substituent for the alkyl which can be substituted, the alkenyl which can be substituted to be substituted, the alkynyl that can be substituted, alkoxy that can be substituted, the alkenyloxy that can be substituted, the alkynyloxy which can be substituted, the alkylthio which can be substituted, the alkenylthio which can be substituted and the alkynylthio which can be substituted, for R5, is halogen, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl , amino, monoalkylamino, dialkylamino, nitro or cyano. The substituent for the phenyl which can be substituted, the phenoxy which can be substituted, the phenylthio which can be substituted, the phenylsulfinyl which can be substituted, the phenylsulfonyl which can be substituted, the benzyl which can be substituted, the benclloxy which can be substituted substituted, the benzylthio which can be substituted or the benzoyl which can be substituted, for each of R2 and R3, the substituent for the phenyl which can be substituted, the phenoxy which can be substituted, the phenylthio which can be substituted, the benzyl which can be substituted, the benzyloxy which can be substituted or the benzylthio which can be substituted, for R5, the substituent for the phenyl which can be substituted, the phenoxy which can be substituted, the phenylthio which can be substituted, the phenylsulfinyl which can be substituted to be substituted, the phenylsulfonyl that can be substituted, the benzyl that can be substituted, the benzyloxy that can be substituted, the benzylthio that can be substituted or the benzo which can be substituted, for Rg, or the substituent for the heterocyclic group for J is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro, cyano, -S (O) wR6, amino, monoalkylamino or dialkylamino, R6 is alkyl or halogenalkyl, and w is from 0 to 2.

3. The acrylonitrile compound or its salt according to claim 1, further characterized in that the heterocyclic group for J is furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl. , isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, 1-pyrrolidinyl, 1-piperidinyl or 4-morpholino.

4. The acrylonitrile compound or its salt according to claim 1, further characterized in that Q is Qa, Qb or Qc, and each of R2 and R3 is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, cyano, phenyl which can be substituted by Mi, or phenoxy which can be substituted by Mi, R5 is alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, aminoalkyl, monoalkylaminoalkyl, dialkylaminoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy , alkylthio, haloalkylthio, 64 alkoxycarbonylalkylthio, alkenylthio, haloalkenylthio, alkynylthio, haloalkynylthio, cycloalkyl, cycloalkylthio, -N (R7) R8, phenyl which can be substituted by Mi, phenoxy which can be substituted by Mi, phenylthyl which can be substituted by Mi, benzyl which can be substituted per M, benzylthio which can be substituted by Mi, pyridyl which can be substituted by Mi, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholino, pyridyloxy which can be substituted by Mi or pyridylthio which can be substituted by Mi, Rg is cyano, phenyl which can be substituted by Mi, benzyloxy which can be substituted by Mi, benzoyl which can be substituted by Mi, pyridyl which can be substituted by Mi, -C (= O) R? 0 -S (O) wR? or trimethylsilyl, Mi is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro, cyano, -S (O) wR6, amino, monoalkylamino or dialkylamino, and Re is alkyl or haloalkyl.

5. The acrylonitrile compound or its salt according to claim 1, further characterized in that Q is Qa, Qb, or Qc, each of R2 and R3 is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, cyano, phenyl which can be substituted by M2, or phenoxy which can be substituted by M2, R5 is alkyl, haloalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxycarbonylalkyl, alkenylthio , halogenoalkenylthio, alkynyl, haloalkynylthio, cycloalkyl, cycloalkylthio, -N (R7) R8, phenyl which can be substituted by M2, phenoxy which can be substituted by M2, phenylthio which can be substituted by M2, benzyl which can be substituted by M2, benzylthio which can be substituted by M2, pyridyl which can be substituted by M2, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholino, each of R and R8 is hydrogen or alkyl, Rg is c iano, phenyl which can be substituted by M2, benzyloxy which can be substituted by M2, benzoyl which can be substituted by M2, pyridyl which can be substituted by M2, -C (= O) R10, -S (O) wR-? or trimethylsilyl, M2 is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro, cyano or S (O) wR6, and Re, is alkyl.

6. The acrylonitrile compound or its salt, according to claim 5, further characterized in that Q is Qa or Qb.

7. The acrylonitrile compound or its salt, according to claim 6, further characterized in that Q is Qa.

8. The acrylonitrile compound or its salt according to claim 1, further characterized in that Q is Qa or Qb, Y is = C (R4) -, and R4 is hydrogen.

9. The acrylonitrile compound or its salt, according to claim 8, further characterized in that Q is Qa.

10. The acrylonitrile compound or its salt, according to claim 8 or 9, further characterized in that R2 is halogen, alkyl or haloalkyl, and I is 1 to 3.

1 1. The acrylonitrile compound or its sai , according to claim 8 or 9, further characterized in that R1 is alkoxyalkyl, -C (= O) R5, -C (= S) R5, -S (O) wR5 or -CH2Rg, R2 is halogen, alkyl or haloalkyl R is halogen or alkyl, R5 is alkyl, haloalkyl, alkoxyalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxycarbonylalkythio, alkenylthio, -N (R7) R8, phenyl which can be substituted by M3, phenoxy which can be substituted by M3 > phenylthio which can be substituted by M3, benzyl which can be substituted by M3, pyridyl which can be substituted by M3, 1-pyrrolidinyl or 4-morpholino, each of R and R8 is hydrogen or alkyl, Rg is phenyl, M3 is halogen , alkyl or alkoxy, I is 1 to 3, m is 0 to 3, n is 0 to 1, and w is 1 to 2.

12. The acrylonitrile compound or its salt according to claim 1, further characterized in that formula (I) is formula (I-1): wherein Q is Qa or Qb, R2 is halogenoalkyl, R2b is halogen, alkyl or haloalkyl, d is from 0 to 2, m is from 0 to 3, and n is from 0 to 1.

13.- The acrylonitrile compound or its salt, according to claim 12, further characterized in that Q is Qa.

14. The acrylonitrile compound or its salt, according to claim 12, further characterized in that d is 0.

15. The acrylonitrile compound or its salt, according to claim 13, further characterized in that it is 0. 1

16. The acrylonitrile compound or its salt according to claim 12, 13, 14 or 15, further characterized in that Ri is alkoxyalkyl, -C (= 0) R 5 -C (= S) R 5, -S (0) wRs or -CH2R9, R2 is halogen, alkyl or haloalkyl, R3 is halogen or alkyl, R5 is alkyl, haloalkyl, alkoxyalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxycarbonylalkyl, alkenylthio, -N (R7) R8, phenyl which can be substituted by M3, phenoxy which can be substituted by M3, phenylthio which can be substituted by M3, benzyl which can be substituted by M3, pyridyl which can be substituted by M3, 1-pyrrolidinyl or 4-morpholino, each R7 and R8 is hydrogen or alkyl, Rg is phenyl, M3 is halogen, alkyl or alkoxy, l is from 1 to 3, m is from 0 to 3, n is from 0 to 1, and w is from 1 to 2.

17. A process to produce a compound of acrylonitrile of the following formula (I) or its salt: where Q is: Qa Qb Qc Qd Y is = C (R4) - or = N-, Ri is alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, -C (= O) R5, -C (= S) R5 , -S (O) wR5 or -CH2Rg, each of R2 and R3 is halogen, alkyl that can be substituted, alkenyl that can be substituted, alkynyl that can be substituted, alkoxy that can be substituted, alkenyloxy that can be substituted, alkynyloxy which may be substituted, alkylthio which may be substituted, alkylsulfinyl, which may be substituted, alkylsulfonyl which may be substituted, alkenylthio which may be substituted alkenylsulfinyl which may be substituted, alkenylsulfonyl which may be substituted, alkynylthio which may be substituted, alkynylsulfinyl which it can be substituted, alkynylsulfonyl which can be substituted, nitro, cyano, phenyl which can be substituted, phenoxy which can be substituted, phenylthio which can be substituted, phenylsulfinyl which can be substituted, phenylsulfonyl which can be substituted, to be substituted, benzyl which can be substituted, benzyloxy which can be substituted benzylthio which can be substituted, benzoyl which can be substituted, R 4 is hydrogen, halogen, alkyl or haloalkyl, R 5, is alkyl which can be substituted, alkenyl which can be substituted , alkynyl which can be substituted, alkoxy that can be substituted, alkenyloxy which can be substituted alkynyloxy which can be substituted, alkylthio which can be substituted alkenylthio which can be substituted, alkynithio which can be substituted, cycloalkyl, cycloalkyloxy, cycloalkylthio which can be substituted , -N (R) R8, phenyl which can be substituted, phenoxy which can be substituted, phenylthio which can be substituted, benzyl which can be substituted, benclloxy which can be substituted, benzylthio which can be substituted, -J, -OJ or -SJ, each of R7 and R8 is hydrogen, alkyl or alkoxy, Rg is damage, phenyl can be substituted, phenoxy can be substituted, phenylthio can be substituted, e to be substituted, phenylsulfinyl which can be substituted, phenylsulfonyl which can be substituted, benzyl which can be substituted, benzyloxy which can be substituted, benzylthio which can be substituted, benzoyl which can be substituted, -J, -C (= O) R - | 0, -C (= S) R10, -S (O) wR? Oo trimethylsilyl, R-? 0 is alkyl or alkoxy, J is a 5- or 6-membered heterocyclic group containing from 1 to 4 heteroatoms and by at least one type selected from the group consisting of O, S and N (the heterocyclic group can be substituted), I is from 1 to 4, m is from 0 to 5, n is from 0 to 3, q is from 0 to 4, w is from 0 to 2; when I is 2 or more, a plurality of R2 may be the same or different; when each m, n and q is 2 or more, a plurality of R3 can be equal or different, provided that the following compounds are excluded: (1) a compound in which Q is Qb, Y is = C (R4), - , and R1 is alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, -S (0) WR5 or -CH2R9. (2) a compound in which Q is Qb, and is = C (R4) -, R-i is -C (= O) R5, and R5 is alkyl that can be substituted, alkenyl which may be substituted, alkynyl which may be substituted, alkoxy which may be substituted alkenyloxy which may be substituted, alkynyloxy which may be substituted, cycloalkyl, cycloalkyloxy, -N (R7) R8, phenyl which may be substituted, phenoxy which may be substituted to be substituted, phenylthio which can be substituted, benzyl which can be substituted, benzyloxy which can be substituted benzylthio which can be substituted, -J, -OJ or -SJ, (3) a compound in which Q is Qb, Y is = C (R4) -, Ri is -C (= S) R5, and R5 is -N (R7) R8, (4) a compound in which Q is Qb or Qc, Y is = N-, R-, is alkyl or -C (= 0) R5 and R5 is alkyl, (5) 3- (4-chlorophenyl) -2-phenyl-3-ethoxy-acrylonitrile, (6) 2- (3,5-dimethoxyphenyl) - 3- (2-methoxy-4-methylphenyl) -3-acetoxy-acrylonitrile, and (7) 2- (3,5-dimethoxyphenyl) -3- (2,6-dimethoxy-4-methylphenyl) -3-acetoxy-cyanitrile, comprising the reaction of a compound of the formula (II). wherein Q, Y, R2 and I are as defined above, with a compound of the formula (III): R? -X (lll) where R? it is as defined previously, and X is halogen.

18. A pesticide containing the acrylonitrile compound or its salt according to claim 1, as an active ingredient.

19. An insecticide, miticide or nematicide containing the acrylonitrile compound or its salt according to claim 1, as an active ingredient.

20. - A fungicide containing the acrylonitrile compound or its salt according to claim 1, as an active ingredient.

21. A marine antifoulant agent containing the acrylonitrile compound or its salt according to claim 1, as an active ingredient.

22. A compound of the formula (ll-l) or its salt: where Q is Qa Qb Qc Qd R2a is hologenoalkyl, R2b is halogen, alkyl or haloalkyl, R3 is halogen, alkyl that can be substituted, alkenyl that can be substituted, alkynyl that can be substituted, alkoxy that can be substituted, alkenyloxy that can be substituted, alkynyloxy that can be substituted, substituted, alkylthio which may be substituted, alkylsulfinyl which may be substituted, alkylsulfonyl which may be substituted, alkenylthio which may be substituted, alkenylsulfinyl which may be substituted, alkenylsulfonyl which may be substituted, alkynylthio which may be substituted, alkynylsulfinyl which may be substituted, alkylsulfonyl which can be substituted, nitro, cyano, phenyl which can be substituted, phenoxy which can be substituted, phenylthio which can be substituted, phenylsulfinyl which can be substituted, phenylsulfonyl which can be substituted, benzyl which can be substituted, benzyloxy which can be substituted, be replaced, benzylthio that can be substituted, or benzoyl that can to be substituted, of is from 0 to 2, m is from 0 to 5, n is from 0 to 3, q is from 0 to 4, when d is 2, two R2b can be the same or different, _: when each m, n and q is 2 or more, a plurality of R3 can be the same or different, when Q is Qc, (1) q is not 0, or (2) R3 is not alkyl.

23. The compound or its salt according to claim 22, further characterized in that Q is Qa or Qb.

24. The compound or its salt according to claim 22, further characterized in that Q is Qa.

25. The compound or its salt according to claim 15, 22, 23 or 24, further characterized in that d is 0. 26.- A method for controlling a pest, comprising the application of the compound according to claim 1 or 22 as an active ingredient to the pest.