(1) EP 104690A, EP 62238A and U.S. Patent 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) 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 disclosure at all with respect to the group of compounds of the present invention.

(3) JP-A-60-11401 and JP-A-60-11452, respectively, disclose a-cyanoketone derivatives which literally cover a part of the compounds of the present invention, but in these publications, there is no specific disclosure at all with respect to the group of compounds of the present invention.

(4) U.S. Patent 3,337,565 discloses acrylonitrile derivatives which literally cover a part of the compounds of the present invention, but in this publication, there is no specific disclosure at all 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) W097/40009 discloses ethylene derivatives similar to the compounds of the present invention, but the derivatives and the compounds of the present invention are different in their chemical structures.

(7) Bulletin de la Societe 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) Journal of Chemical Research (Synopses), 1987, p.

78-79, discloses 2-(3,5-dimethoxyphenyl)-3-(2-methoxy-4- methylphenyl)-3-acetoxyacrylonitrile and 2-(3, 5- dimethOxyphenyl)-3-(2,6-dimethoxy-4-methylphenyl)-3- acetoxyacrylonitrile, but these compounds and the compounds of the present invention are different in their chemical structures.

The present inventors have conducted various studies

to find out an excellent pesticide, paying an attention to acrylonitrile compounds and, as a result, have accomplished the present invention.

Namely, the present invention provides an acrylonitrile compound of the following formula (I) or its salt: wherein Q is Y is =C(R4)- or =N-, R1 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 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, 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 may be substituted, nitro, cyano, phenyl which may be substituted, phenoxy which may be substituted, phenylthio which may be substituted, phenylsulfinyl which may be substituted, phenylsulfonyl which may be substituted, benzyl which may be substituted, benzyloxy which may be substituted, benzylthio which may be substituted, or benzoyl which may be substituted, R4 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, alkynylthio which may be substituted, cycloalkyl, cycloalkyloxy, cycloalkylthio, -N(R7)R8, phenyl which may be substituted, phenoxy which may be substituted, phenylthio which may be substituted, benzyl which may be substituted, benzyloxy which may be substituted, benzylthio which may be substituted, -J, -O-J or -S-J, each of R7 and R8 is hydrogen, alkyl or alkoxy, Rg is cyano, phenyl which may be substituted, phenoxy which may be substituted, phenylthio which may be substituted, phenylsulfinyl which may be substituted, phenylsulfonyl which may be substituted, benzyl which may be substituted, benzyloxy which may be substituted,

benzylthio which may be substituted, benzoyl which may be substituted, -J, -C(=O)R10, -C(=S)R10, S(O)wRio or trimethylsilyl, Rlo is alkyl or alkoxy, J is a 5- or 6-membered heterocyclic group containing from 1 to 4 hetero atoms of at least one type selected from the group consisting of O, S and N (the heterocyclic group may be substituted), 1 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 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, provided that the following compounds are excluded (1) a compound wherein Q is Qb, Y is =C(R4)-, and R1 is alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, -S(O),RS or -CH2R9, (2) a compound wherein Q is Qb, Y is =C(R4)-, R1 is -C(=O)R5, and 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, cycloalkyl, cycloalkyloxy, -N(R7)R8, phenyl which may be substituted, phenoxy which may be substituted, phenylthio which may be substituted, benzyl which may be substituted, benzyloxy which may be substituted, benzylthio which may be substituted, -J, -O-J or -S-J, (3) a compound wherein Q is Qb, Y is =C(R4)-, R1 is -C(=S)R5, and R5 is -N(R7)R8, (4) a

compound wherein Q is Qb or Qc, Y is =N-, R1 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- acetoxyacrylonitrile, and (7) 2-(3,5-dimethoxyphenyl)-3- (2, 6-dimethoxy-4-methylphenyl ) -3-acetoxyacrylonitrile; 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 which may be substituted, the alkenyl which may be substituted, the alkynyl which may be substituted, the alkoxy which may be substituted, the alkenyloxy which may be substituted, the alkynyloxy which may be 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 alkenylsulfonyl which may be substituted, the alkynylthio which may be substituted, the alkynylsulfinyl which may be substituted and the alkynylsulfonyl which may be substituted, for each of R2 and R3, or the substituent for the alkyl which may be substituted, the alkenyl which may be substituted, the alkynyl which may be substituted, the alkoxy which may be substituted, the alkenyloxy which may be substituted, the alkynyloxy which may be substituted, the alkylthio which may be substituted, the

alkenylthio which may be substituted and the alkynylthio which may be substituted, for R57 may, for example, be 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 then one, a plurality of substituents may be the same or different.

Further, the substituent for the phenyl which may be substituted, the phenoxy which may be substituted, the phenylthio which may be substituted, the phenylsulfinyl which may be substituted, the phenylsulfonyl which may be substituted, the benzyl which may be substituted, the benzyloxy which may be substituted, the benzylthio which may be substituted or the benzoyl which may be substituted, for each of R2 and R3, the substituent for the phenyl which may be substituted, the phenoxy which may be substituted, the phenylthio which may be substituted, the benzyl which may be substituted, the benzyloxy which may be substituted or the benzylthio which may be substituted, for R5, the substituent for the phenyl which may be substituted, the phenoxy which may be substituted, the phenylthio which may be substituted, the phenylsulfinyl which may be substituted, the phenylsulfonyl which may be substituted, the benzyl which may be substituted, the benzyloxy which may be

substituted, the benzylthio which may be substituted or the benzoyl which may be substituted, for Rg, or the substituent for the heterocyclic ring for J, may, for example, be halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro, cyano, -S(O)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, R6 is alkyl or haloalkyl, and w is from 0 to 2.

The heterocyclic group for J may, for example, be furyl, thienyl, pyrrolyl, pyrazolyl, imdazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, l-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 M1, or phenoxy which may be substituted by M1, R5 is alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, aminoalkyl, monoalkylaminoalkyl, dialkylaminoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxycarbonylalkylthio, alkenylthio, haloalkenylthio, alkynylthio, haloalkynylthio, cycloalkyl, cycloalkylthio,

-N(R7)R8, phenyl which may be substituted by M1, phenoxy which may be substituted by M1, phenylthio which may be substituted by M1, benzyl which may be substituted by M1, benzylthio which may be substituted by M1, pyridyl which may be substituted by M1, l-pyrrolidinyl, l-piperidinyl, 4-morpholino, pyridyloxy which may be substituted by M1, or pyridylthio which may be substituted by M1, Rg is cyano, phenyl which may be substituted by M1, benzyloxy which may be substituted by M1, benzoyl which may be substituted by M1, pyridyl which may be substituted by M1, -C(=O)Rlo, -S(O) wRi0 or trimethylsilyl, M1 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 M1 may be one or more, and if it is more than one, a plurality of M1 may be the same or different.

(b) The acrylonitrile compound or its salt, wherein Q is Qa, Qb or Qc, 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, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxycarbonylalkylthio, alkenylthio, haloalkenylthio, alkynylthio, haloalkynylthio, cycloalkyl, cycloalkylthio, -N(R7)R8, phenyl which may be substituted by M2, phenoxy which may

be substituted by M2, phenylthio which may be substituted by M2, benzyl which may be substituted by M2, benzylthio which may be substituted by M2, pyridyl which may be substituted by M2, l-pyrrolidinyl, l-piperidinyl or 4- morpholino, each of R7 and R8 is hydrogen or alkyl, Rg is cyano, phenyl which may be substituted by M2, benzyloxy which may be substituted by M2, benzoyl which may be substituted by M2, pyridyl which may be substituted by M2, -C(=O)Rlo, -S(O)WRlo or trimethylsilyl, M2 is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro, cyano or -S(O)WR6, and R6 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 the above (b), wherein Q is Qa or Qb.

(d) The acrylonitrile compound or its salt according to the above (c), 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 the above (e), wherein Q is Qa.

(g) The acrylonitrile compound or its salt according to the above (e) or (f), wherein R2 is halogen, alkyl or haloalkyl, and 1 is from 1 to 3.

(h) The acrylonitrile compound or its salt according to the above (e) or (f), wherein R1 is alkoxyalkyl,

-C(=O)R5, -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 may be substituted by M3, phenoxy which may be substituted by M3, phenylthio which may be substituted by M3, benzyl which may be substituted by M3, pyridyl which may be substituted by M3, l-pyrrolidinyl or 4-morpholino, each of R7 and R8 is hydrogen or alkyl, Rg is phenyl, M3 is halogen, alkyl or alkoxy, 1 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 may be one or more, and when it is more than one, a plurality of M3 may be the same or different.

(i) The acrylonitrile compound of the formula (I) or its salt, wherein the formula (I) is the formula (1-1): wherein Q is Qa or Qb, R2a is haloalkyl, 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 may be the same or different.

(j) The acrylonitrile compound or its salt according to the above (i), wherein Q is Qa.

(k) The acrylonitrile compound or its salt according

to the above (i), wherein d is 0.

(1) The acrylonitrile compound or its salt according to the above (j), wherein d is 0.

(m) The acrylonitrile compound or its salt according to the above (i), (j), (k) or (1), wherein R1 is alkoxyalkyl, -C(=O)R5, -C(=S)R5, -S (O)WR5 or -CH2R9, 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 may be substituted by M3, phenoxy which may be substituted by M3, phenylthio which may be substituted by M3, benzyl which may be substituted by M3, pyridyl which may be substituted by M3, l-pyrrolidinyl or 4-morpholino, each of R7 and R8 is hydrogen or alkyl, Rg is phenyl, M3 is halogen, alkyl or alkoxy, 1 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 or alkyl moiety contained in R1, R2, R2a, R2b, R3, R4, R5, R6, R7, Ra, R10, M1, M2 or M3, may, for example, be straight chain or branched one having from 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl or hexyl. The alkenyl, alkynyl, alkenyl moiety or alkynyl moiety contained in R1, R2, R3 or R5, may, for example, be straight chain or branched one having from 2 to 6 carbon atoms, such as vinyl, allyl, butadienyl, isopropenyl,

ethynyl, propinyl or 2-penten-4-enyl. The cycloalkyl or cycloalkyl moiety contained in R5, may, for example, be 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 R1, R2, R2ar R2b, R3, R4, R6rM M2 or M3, or the halogen as a substituent, may be fluorine, chlorine, bromine or iodine. The number of halogens as substituents may be one or more, and when it is 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 a salt may be any salt so long as it is acceptable for agriculture. For example, it may 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) may have geometrical isomers (E-isomer and Z-isomer). The present invention includes such isomers and their mixtures.

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 reactions (A) to (C) and by a usual process for producing a salt.

Now, the reaction (A) will be described.

In the reaction (A), Q, Y, R1, R2, 1 and the formula (I) are as defined above, and X is halogen.

The reaction (A) is carried out usually in the presence of a base. As such a base, one or more may suitably be selected for use from e.g. alkali metals such as sodium and potassium; alkali metal alcoholates such as potassium tertiary 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; and tertiary amines such a trimethylamine, triethylamine, pyridine and 4- dimethylaminopyridine.

The reaction (A) may be carried out, if necessary, in the presence of a solvent. Such a solvent may be any solvent so long as it is inert to the reaction. For example, one or more may be suitably selected for use from e.g. 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 trimethylamine and triethylamine; and water.

For the reaction (A), a catalyst such as 4- dimethylaminopyridine may be used, as the case requires.

The reaction temperature for the reaction (A) is usually from -80 to +1500C, preferably from -50 to +1200C, and the reaction time is usually from 0.1 to 48 hours, preferably from 0.5 to 24 hours.

In a case where in the formula (I), R1 is methyl: ('3) C H (II) + Diazomethane > Q - C C CN ½½(R2)1 (I The reaction (B) will be described in detail. In the reaction (B), Q, Y, R2, 1 and the formula (II) are as defined above.

The reaction (B) is carried out usually in the

presence of a solvent. As such a solvent, one or more may suitably be selected for use from e.g. 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 reaction (B) is usually from 0 to 1000C, preferably from 0 to 500C, and the reaction time is usually from 0.1 to 24 hours, preferably from 0.1 to 12 hours.

In a case where in the formula (I), R1 is -C(=O)R5, -C(=S)R5 or -S(O)WR5: (C) ,0 - T - C 1 First step 4 (II) + C IT-C 1 Q-C Q - C (IV) I Mm CN CV) ORla yO K1 a CV) + C-K5 Second-step Q-C C (VI) C N Mm) R 2) I cN K (I -3)

The reaction (C) will be described. In the reaction (C), Q, Y, R2, R5, 1 and the formula (II) are as defined above, T is -C(=O)-, -C(=S)- or -S(O)w-, G is hydrogen, Li, MgBr, MgCl or MgI, and Ria is -C(=O)R5, -C(=S)R5 or -S(O)WR5 (wherein R5 and w are as defined above).

The first step in the reaction (C) is carried out, if necessary, in the presence of a base. As such a base, one or more may suitably be selected for use from e.g.

tertiary amines such as trimethylamine, triethylamine, pyridine and 4-dimethylaminopyridine.

The first step of the reaction (C) is carried out usually in the presence of a solvent. Such a solvent may be any solvent so long as it is inert to the reaction.

For example, one or more may suitably selected for use from e.g. 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 +l500C, preferably from -50 to +800C, 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 such a base, one or more may suitably be selected for use from e.g.

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 carried out usually in the presence of a solvent. Such a solvent may be any solvent so long as it is inert to the reaction.

For example, one or more may suitably be selected for use from e.g. 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 +1500C, preferably from -80 to +800C, and the reaction time is usually from 0.1 to 48 hours, preferably from 0.5 to 24 hours.

The compounds of the formula (II) in the above reactions (A) to (C) are intermediate compounds useful for producing the compounds of the present invention, and

novel compounds are included therein.

The compound of the formula (II) may form a salt.

Such a salt may be any salt so long as it is agriculturally acceptable. For example, it may be an inorganic salt such as a hydrochloride, a sulfate or a nitrate; an organic salt such as an acetate or a methane sulfonate, 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 geometrical isomers (E-isomer and Z-isomer). The present invention includes such isomers and mixtures thereof. The compound of the formula (II) may also be present in the form of tautomers represented by the following formula: The present invention includes such tautomers and mixtures thereof.

Further, the compounds of the formula (II) include those which exhibit pesticidal activities.

The compound of the formula (II) or its salt may be prepared e.g. by reactions (D) to (F), or by a conventional method for producing a salt.

The reaction (D) will be described. In the reaction (D), Q, Y, R2, 1 and the formula (II) are as defined above, and Z1 is alkoxy.

The reaction (D) is carried out usually in the presence of a base and a solvent. As such a base, one or more may suitably be selected for use from e.g. alkali metals such as sodium and potassium; alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tertiary butoxide; metal hydrides such as potassium hydride and sodium hydride; and organic lithium such as methyllithium, butyllithium, tert-butyllithium and phenyllithium. As the solvent, one or more may suitably selected for use from e.g. aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenene; ethers such as dioxane, tetrahydrofuran and diethyl ether; and alcohols such as methanol, ethanol, propanol and tert- butanol.

The reaction temperature for the reaction (D) is usually from -80 to +1500C, preferably from -50 to +l200C, and the reaction time is usually from 0.1 to 48 hours, preferably from 0.5 to 24 hours.

In a case where in the formula (II), Q is Qa:

[E) (K 2) I < First step Qa -CH2 CN + COJ C O Z2 First step y (VII - 1) (IX) 0 II (K 2)I O-e 0 Qa -C C A Y Second step Hydrolysis C N (R %CK2) CX) The reaction (E) will be described as follows. In the reaction (E), Qa, Y, R2 and 1 are as defined above, and Z2 is halogen.

The first step of the reaction (E) is carried out usually in the presence of a base. As such a base, one or more may suitably be selected for use from e.g. alkali metals such as sodium and potassium; alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tertiary 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. Such a solvent may be any solvent so long as it is inert to the reaction. For example, one or more may suitably be selected for use from e.g. aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenene; 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; 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 may be used, as the case requires.

The reaction temperature for the first step of the reaction (E) is usually from -80 to +1500C, preferably from -50 to +1200C, 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 of the present invention.

Accordingly, the compound of the present invention can be prepared also by the first step of the reaction (E).

The second step of the reaction (E) is a hydrolysis reaction which is carried out usually in the presence of a base or an acid. As the base, one or more may suitably be selected for use from e.g. 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 may suitably be selected for use from e.g. 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. Such a solvent may be any solvent so long as it is inert to the reaction. For example, one or more may suitably be selected for use from e.g. nitriles such as acetonitrile, propionitrile and acrylonitrile; alcohols such a 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 from 0 to 1000C, preferably from

0 to 500C, and the reaction time is usually from 0.1 to 48 hours, preferably from 0.5 to 24 hours.

In a case where in the formula (II), Q is Qc: (F) The reaction (F) will be described as follows. In the reaction (F), Qc, Y, R2, 1 and the formula (IX) are as defined above.

The reaction (F) is carried out in accordance with the first step of the reaction (E).

Among compounds of the formula (II) thus prepared, the following compounds are particularly useful and novel.

Compounds of the formula (II-1) or their salts: wherein Q, R2ar R2b 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 among the compounds of the formula (II-1) are as follows.

(n) A compound of the above formula (II-1) wherein Q is Qa or Qb, or its salts.

(o) A compound of the above formula (II-1) wherein Q is Qa, or its salt.

(p) A compound of the above formula (II-1), (n) or (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, a miticide, a nematicide, a soil pesticide, a fungicide and a marine antifouling agent.

Preferred embodiments of pesticides containing the compounds of the present invention will now be described.

Firstly, pesticides such as an insecticide, a miticide, a nematicide, a soil pesticide and a fungicide, will be described.

The pesticides containing the compounds of the present invention are useful as an insecticide, a miticide, a nematicide and a soil pesticide (hereinafter referred to as insect pest control agents), and they are effective for controlling plant parasitic mites such as two-spotted spider mite (Tetranychus urticae), carmine spider mite (Tetranychus cinnabarinus), kanzawa spider mite (Tetranychus kanzawai), citrus red mite (Panonychus citri), European red mite (Panonychus ulmi), broad mite (Polyphaqotarsonemus latus), pink citrus rust mite (Aculops pelekassi) and bulb mite (Rhizoqlyphus

echinopus); animal parasitic mites such as Ixodes; aphids such as green peach aphid (Myzus persicae) and cotton aphid (Aphis gossypii); agricultural insect pests such as diamondback moth (Plutella xylostella), cabbage armyworm (Mamestra brassicae), common cutworm (Spodoptera litura), codling moth (Laspeyresia pomonella), bollworm (Heliothis zea), tobacco budworm (Heliothis virescens), gypsy moth (Lymantria dispar), rice leafroller (Cnaphalocrocis medinalis), Adoxophyes sp., colorado potato beetle (Leptinotarsa decemlineata), cucurbit leaf beetle (Aulacophora femoralis), boll weevil (Anthonomus grandis), planthoppers, leafhoppers (Circulifer sp.), scales, bugs, whiteflies, thrips, grasshoppers, anthomyiid flies, scarabs, black cutworm (Aqrotis ipsilon), cutworm (Aqrotis segetum) and ants; plant parasitic nematodes such as root-knot nematodes, cyst nematodes, root-lesion nematodes, rice white-tip nematode (Aphelenchoides besseyi), strawberry bud nematode (Nothotylenchus acris), pine wood nematode (Bursaphelenchus liqnicolus); gastropods such as slugs and snails; soil pests such as isopods such as pillbugs (Armadilidium vulgare) and pillbugs (Porcellio scaber); hygienic insect pests such as tropical rat mite (Ornithonyssus bacoti), cockroachs, housefly (Musca domestica) and house mosquto (Culex pipiens); stored grain insect pests such as angoumois grai moth (Sitotroga cerealella), adzuki bean weevil (Callosobruchus

chinensis), red flour beetle (Tribolium castaneum) and mealworms; household goods insect pests such as casemaking clothes moth (Tinea pellionella), black carpet beetle (Anthrenus scrophularidae) and subterranean termites; domestic mites such as mold mite (Tyrophagus putrescentiae), Dermatophaqoides farinae and Chelacaropsis moorei; and others such as fleas, lice and flies, which are parasitic to e.g. domestic animals.

Among them, the insect pest control agents containing the compounds of the present invention are particularly effective for controlling plant parasitic mites, animal parasitic mites, agricultural insect pests, hygienic insect pests, household goods insect pests, domestic mites or the like. Further, they are effective against insect pests having acquired resistance to organophosphorus, carbamate and/or synthetic pyrethroid insecticides. Moreover, the compounds of the present invention have excellent systemic properties, and by the application of the compounds of the present invention to solid treatment, not only noxious insects, noxious mites, noxious nematodes, noxious gastropods and noxious isopods in soil but also foliage pests can be controlled.

Further, the pesticides containing compounds of the present invention are useful as fungicides. For example, they are effective for controlling diseases, such as blast (Pyricularia oryzae), sheath blight (Rhizoctonia solani) and brown spot (Cochliobolus miyabeanus) against

rice; powdery mildew (Erysiphe graminis), scab (Gibberella zeae), rust (Puccinia striiformis, P.

coronata, . graminis, P. recondita, P. hordei), snow blight (Typhula sp., Micronectriella nivalis), loose smut (Ustilaqo tritici, U. nuda), eye spot (Pseudocercosporella herpotrichoides), leaf blotch (Septoria tritici) and glume blotch (Leptosphaeria nodorum) against cereals; melanose (Diaporthe citri) and scab (Elsinoe fawcetti) against citrus; blossom blight (Sclerotinia mali), powdery mildew (Podosphaera leucotricha), alternaria blotch (Alternaria mali) and scab (Venturia inaequalis) against apples; scab (Venturia nashicola) and black spot (Alternaria kikuchiana) against pears; brown rot (Monilinia fructicola), scab (Cladosporium carpophilum) and phomopsis rot (Phomopsis sp.) against peaches; anthracnose (Elsinoe ampelina) ripe rot (Glomerella cinqulata), powdery mildew (Uncinula necator) and downy mildew (Plasmopara viticola) against grapes; anthracnose (Gloeosporium kaki) and angular leaf spot (Cercospora kaki) against Japanese persimon; anthracnose (Colletotrichum laqenarium), powdery mildew (Sphaerotheca fuliqinia), gummy stem blight (Mycosphacrella melonis) and downy mildew (Pseudopernospora cubensis) against cucurbits; early blight (Alternaria solani), leaf mold (Cladosporium fulvum) and late blight (Phytophthora infestans) against tomatoes; alternaria leaf spot (Alternaria brassicae)

against crucifer; early blight (Alternaria solani) and late blight (Phytophthora infestans) against potatoes; powdery mildew (Sphaerotheca humuli) against strawberry; gray mold (Botrytis cinerea) and sclerotinial rot (Sclerotinia sclerotiorum) against various crop plants.

Further, they are effective also for controlling soil diseases brought about by plant pathogenic fungi such as Fusarium sp., Pythium sp., Rhizoctonia sp., Verticillium sp., and Plasmodiophora sp.

Another preferred embodiments of the pesticides containing compounds of the present invention may be agricultural and horticultural pesticides which collectively control the above-mentioned plant parasitic mites, agricultural insect pests, plant parasitic nematodes, gastropods, soil pests, various diseases and various soil diseases.

The pesticide such as the insect pests control agent or the fungicide containing the compound of the present invention, is usually formulated by mixing the compound with various agricultural adjuvants and used in the form of a formulation such as a dust, granules, water- dispersible granules, a wettable powder, a water-based suspension concentrate, an oil-based suspension concentrate, water soluble granules, an emulsifiable concentrate, a paste, an aerosol or an ultra low-volume formulation. However, so long as it is suitable for the purpose of the present invention, it may be formulated

into any type of formulation which is commonly used in this field. Such agricultural adjuvants include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaoline, bentonite, a mixture of kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite and starch; solvents such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethylsulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2- pyrrolidone, and alcohol; anionic surfactants and spreaders such as a salt of fatty acid, a benzoate, an alkylsulfosuccinate, a dialkylsulfosuccinate, a polycarboxylate, a salt of alkylsulfuric acid ester, an alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyl sulfonate, an alkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, an alkyldiphenyl ether disulfonate, a polystyrene sulfonate, a salt of alkylphosphoric acid ester, an alkylaryl phosphate, a styrylaryl phosphate, a salt of polyoxyethylene alkyl ether sulfuric acid ester, a polyoxyethylene alkylaryl ether sulfate, a salt of polyoxyethylene alkylaryl ether sulfuric acid ester, a polyoxyethylene alkyl ether phosphate, a salt of polyoxyethylene alkylaryl phosphoric acid ester, and a salt of a condensate of naphthalene sulfonate with formalin; nonionic surfactants and

spreaders such as a sorbitan fatty acid ester, a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, an oxyalkylene block polymer, a polyoxyethylene alkyl ether, a polyoxyethylene alkylaryl ether, a polyoxyethylene styrylaryl ether, a polyoxyethylene glycol alkyl ether, a polyoxyethylene fatty acid ester, a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene glycerin fatty acid ester, a polyoxyethylene hydrogenated 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, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, and liquid paraffins. Such adjuvants may be selected for use among those known in this field, so long as the purpose of the present invention can thereby be accomplished. Further, various additives which are commonly used, such as a filler, a thickener, an anti-settling agent, an anti- freezing agent, a dispersion stabilizer, a phytotoxicity reducing agent, and an anti-mold agent, may also be employed.

The weight ratio of the compound of the present invention to the various 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 such a formulation, it may be used as it is, or may be diluted to a predetermined concentration with a diluent such as water, and various extenders may be added thereto, as the case requires.

The application of the pesticide such as the insect pest control agent or the fungicide containing the compound of the present invention can not generally be defined, as it varies depending upon the weather conditions, the type of the formulation, the application season, the application site or the types or degree of outbreak of the pest insects. However, it is usually applied in a 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 insect pest control agent as a preferred embodiment of the pesticide containing the compound of the present invention, can not generally be defined, as it varies depending upon various conditions as mentioned above, but is usually carried out in 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 from 0.1 to 10,000 g, preferably from 10 to 1,000 g, per hectare. The application of the

fungicide can not generally be defined, as it varies depending upon various conditions as described above, but is usually carried out in 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 from 0.1 to 10,000 g, preferably from 10 to 1,000 g, per hectare.

Further, agricultural and horticultural pesticides as another preferred embodiment of pesticides containing the compounds of the present invention may be applied in accordance with the above-described application of insect pest control agents and fungicides. The present invention includes such a method for controlling insect pests by such applications.

Various formulations of pesticides such as insect pest control agents or fungicides containing the compounds of the present invention or their diluted compositions may be applied by conventional methods for application which are commonly employed, such as spraying (e.g. spraying, jetting, misting, atomizing, powder or grain scattering or dispersing in water), soil application (e.g. mixing or drenching), surface application (e.g. coating, powdering or covering) or impregnation to obtain poisonous feed. Further, it is possible to feed domestic animals with a food containing the above active ingredient and to control the outbreak or growth of pests, particularly insect pests, with their

excrements. Furthermore, the active ingredient may also be applied by a so-called ultra low-volume application method. In this method, the composition may be composed of 100% of the active ingredient.

Further, the pesticides such as insect pest control agents or fungicides containing compounds of the present invention may be mixed with or may be used in combination with other agricultural chemicals, fertilizers or phytotoxicity-reducing agents, whereby synergistic effects or activities may sometimes be obtained. Such other agricultural chemicals include, for example, a herbicide, an insecticide, a miticide, a nematicide, a soil pesticide, a fungicide, an antivirus agent, an attractant, an antibiotic, a plant hormone and a plant growth regulating agent. 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 application range, the application time, the pesticidal activities, etc. may be improved to preferred directions.

The compound of the present invention and the active compounds of other agricultural chemicals may separately be formulated so that they may be mixed for use at the time of application, or they may be formulated together.

The present invention includes such a mixed pesticidal composition.

The mixing ratio of the compound of the present

invention to the active compounds of other agricultural chemicals can not generally be defined, since it varies depending upon the weather conditions, the types of formulations, the application time, the application site, the types or degree of outbreak of insect pests, etc.

but it is usually within a range of from 1:300 to 300:1, preferably from 1:100 to 100:1, by weight. Further, 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 such a mixed pesticide composition.

The active compounds of insect pest control agents such as insecticides, miticides, nematicides or soil pesticides in the above-mentioned other agricultural chemicals, include, for example, (by common names, some of them are still in an application stage) organic phosphate compounds such as Profenofos, Dichlorvos, Fenamiphos, Fenitrothion, EPN, Diazinon, Chlorpyrifos- methyl, Acephate, Prothiofos, Fosthiazate and Phosphocarb; carbamate compounds such as Carbaryl, Propoxur, Aldicarb, Carbofuran, Thiodicarb, Methomyl, Oxamyl, Ethiofencarb, Pirimicarb, and Fenobucarb; nereistoxin derivatives such as Cartap, and Thiocyclam; organic chlorine compounds such as Dicofol, and Tetradifon; organometallic compounds such as Fenbutatin Oxide; pyrethroid compounds such as Fenvalerate,

Permethrin, Cypermethrin, Deltamethrin, Cyhalothrin, Tefluthrin, and Ethofenprox; benzoylurea compounds such as Diflubenzuron, Chlorfluazuron, Teflubenzuron, and Novaluron; juvenile hormone-like compounds such as Methoprene; pyridazinone compounds such as Pyridaben; pyrazole compounds such as Fenpyroximate, Fipronil, and Tebufenpyrad; 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, Hexythiazox, Amitraz, Chlordimeform, Silafluofen, Triazamate, Pymetrozine, Pyrimidifen, Chlorfenapyr, Indoxacarb, Acequinocyl, Etoxazole, and Cyromazin. Further, BT agents, microbial agricultural chemicals such as insect viruses, or antibiotics such as Avermectin, Milbemycin and Spinosad, may be used in admixture or in combination.

The active compounds of fungicides among the above- mentioned other agricultural chemicals include, for example, (by common names, some of which are still in an application stage) pyrimidinamine compounds such as Mepanipyrim, Pyrimethanil, and Cyprodinil; azole compounds such as Triadimefon, Bitertanol, Triflumizole, Etaconazole, Propiconazole, Penconazole, Flusilazole, Myclobutanil, Cyproconazole, Terbuconazole, Hexaconazole,

Furconazole-cis, Prochloraz, Metconazole, Epoxiconazole, and Tetraconazole; quinoxaline compounds such as Quinomethionate; dithiocarbamate compounds such as Maneb, Zineb, Mancozeb, Polycarbamate, Propineb; organic chlorine compounds such as Fthalide, Chlorothalonil, and Quintozene; imidazole compounds such as Benomyl, Thiophanate-Methyl, Carbendazim, and 4-chloro-2-cyano-l- dimethylsulfamoyl-5- ( 4-methylphenyl) imidazole; pyridinamine compounds such as Fluazinam; cyanoacetamide compounds such as Cymoxanil; phenylamide compounds such as Metalaxyl, Oxadixyl, Ofurace, Benalaxyl, Furalaxyl, and Cyprofuram; sulfenic acid compounds such as Dichlofluanid; copper compounds such as cupric hydroxide, and Oxine Copper; isoxazole compounds such as Hydroxyisoxazole; organophosphorus compounds such as Fosetyl-Al, Tolcofos-Methyl, S-benzyl 0,0- 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 Vinclozolin; benzanilide compounds such as Flutolanil, and Mepronil; piperazine compounds such as Triforine; pyrizine compounds such as Pyrifenox; carbinol compounds such as Fenarimol; and Flutriafol; piperidine compounds such as Fenpropidine; morpholine compounds such as Fenpropimorph; organotin compounds such as Fentin Hydroxide, and Fentin

Acetate; urea compounds such as Pencycuron; cinnamic acid compounds such as Dimethomorph; phenylcarbamate compounds such as Diethofencarb; cyanopyrrole compounds such as Fludioxonil, and Fenpiclonil; -methoxyacrylate compounds such a Azoxystrobin, Kresoxim-Methyl, and Metominofen; oxazolidinedione compounds such as Famoxadone; anthraquinone compounds; crotonic acid compounds; antibiotics; and other compounds, such as Isoprothiolane, Tricyclazole, Pyroquilon, Diclomezine, Pro. benazole, Quinoxyfen, Propamocarb Hydrochloride and Spiroxamine.

Now, pesticides like marine antifouling agents will be described.

The marine antifouling agents containing the compounds of the present invention are effective for controlling noxious marine organisms against ships or underwater structures (such as harbour structures, buoys, pipelines, bridges, submarine bases, seabed oilfield drilling installations, water conduits for power plants, fixed shore nets and culturing nets). Specifically, they are effective for preventing the attachment and propagation of plants such as green algae and brown algae, animals such as a barnacle, a serpla, an ascidian, a sea mussel and an oyster, various bacteria called slime, and aquatics such as mold and a diatom, at the bottoms of ships or on underwater structures.

The marine anti fouling agents containing the compounds of the present invention provide antifouling

and antislime properties over a long period of time and exhibit excellent effects for preventing the attachment and propagation of noxious marine organisms against ships or underwater structures.

The marine antifouling agents containing the compounds of the present invention are usually formulated and used in the form of paint compositions. However, they may be formulated and used in other forms (such as solutions, emulsifiable concentrates, or pellets) as the case requires. Paint vehicles to be used for formulating the compounds of the present invention into coating compositions, may be resin vehicles which 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 phenol resin, a synthetic rubber, a silicone rubber, a silicone resin, a petroleum resin, a oil and fat resin, a rosin ester resin, a rosin soap or rosin, may be mentioned. Further, as a vehicle having antifouling properties, an acrylic copolymer resin composition containing, as constituting units, an organotin compound salt of an unsaturated mono- or di-carboxylic acid, obtainable by a condensation reaction of (meth)acrylic acid with an organotin compound such as

bis(tributyltin)oxide or triphenyltin hydroxide, or a resin containing a metal element such as copper, zinc or tellurium in its side chains, may, for example, be used.

When the compound of the present invention is formulated as a coating composition, the blend proportion is adjusted so that the compound of the present invention will be contained in an amount of from 0.1 to 60 wt%, preferably from 1 to 40 wtt, based on the entire coating composition.

The coating composition containing the compound of the present invention can be prepared by using e.g. a ball mill, a pebble mill, a roll mill or a sand grinder in accordance with a method which is well known in the field of preparing coating materials. Further, the above 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 further contain any other known inorganic or organic antifouling agent, as the case requires. Such an antifouling agent includes, for example, cuprous oxide, copper rhodanide, copper hydroxide, copper naphthenate, metallic copper and various tin compounds and dithiocarbamic acid derivatives, such as tetramethylthiuram monosulfide, tetramethylthiuram disulfide, zinc bis- (dimethyldithiocarbamate), zinc ethylene-

bis(dithiocarbamate), manganese ethylene- bis(dithiocarbamate), and copper bis(dimethyldithiocarbamate).

As described in the foregoing, the compound of the present invention or the compound of the formula (II) as its intermediate, is effective as an active ingredient of a pesticide. Various embodiments thereof will be summarized as follows.

(1) A pesticide containing a compound of the above formula (I) or (II), or its salt, as an active ingredient, or a method for controlling pests by employing such a 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 by employing such a compound.

(3) An insect pest control agent containing a compound of the above formula (I) or (II), or its salt, as an active ingredient, or a method for controlling pests by employing such a 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 by employing such a compound.

(5) A miticide containing a compound of the above formula (I) or (II), or its salt, as an active

ingredients, or a method for controlling mites by employing such a compound.

(6) A nematicide containing a compound of the above formula (I) or (II), or its salt, as an active ingredient, or a method for controlling nematodes by employing such a 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 for controlling soil pests by employing such a compound.

(8) A fungicide containing a compound of the above formula (I) or (II), or its salt, as an active ingredient, or a method for controlling fungi by employing such a compound.

(9) A marine antifouling agent containing a compound of the above formula (I) of (II), or its salt, as an active ingredient, or a method for controlling marine fouling organisms by employing such a compound.

Now, the present invention will be described in further detail with reference to Examples. However, it should be understood that the present invention is by no means restricted to such specific Examples. Firstly, Examples for preparing compounds of the present invention will be described.

PREPARATION EXAMPLE 1 Preparation of -(2-chlorophenyl)- -isopropylcarbonyloxy- a-(2-thienyl)acrylonitrile (after-mentioned Compound No.

b-35) 1) 1.12 g of sodium was added to 25 ml of dry ethanol, followed by heating to a reflux temperature. Then, a mixture comprising 5.0 g of 2-thiopheneacetonitrile, 7.49 g of ethyl 2-chlorobenzoate and 25 ml of dry ethanol, was dropwise added. After 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 put into water, and the aqueous layer washed with methylene chloride was weakly acidified 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 -(2-chlorophenyl)- -hydroxy- a-(2-thienyl)acrylonitrile having a melting point of from 164 to 1670C. The NMR spectrum data of this compound were as follows.

1H-NMR &ppm (Solvent: CDC13/400 MHz) 6.54(s,lH), 7.18(dd,lH), 7.38-7.60(m,5H), 7.57(dd,lH) 2) 46 mg of triethylamine was added to a mixture comprising 0.12 g of -(2-chlorophenyl)- -hydroxy-a-(2- thienyl)acrylonitrile and 5 ml of dichloroethane, followed by cooling with ice. Then, a mixture comprising 54 mg of isobutylyl chloride and 2 ml of dichloroethane, was dropwise added. 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 put 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 from 84 to 860C. The NMR spectrum data of this product were as follows.

1H-NMR Sppm (Solvent: CDCl3/400 MHz) 1.27(d,6H), 2.90(m,lH), 7.11(dd,1H), 7.33-7.40(m,2H), 7.45(d,2H), 7.52(d,lH), 7.65(dd,1H) PREPARATION EXAMPLE 2 Preparation of -(2,4-dichlorophenyl)- -ethylsulfonyloxy- -(2-trifluoromethylphenyl)acrylonitrile (after-mentioned Compound No. a-63) 1) A mixture comprising 3.7 g of 2- trifluoromethylbenzoyl chloride and 15 ml of toluene, were dropwise added with stirring at room temperature to a mixture comprising 3.0 g of 2,4- dichlorophenylacetonitrile, 45 ml of toluene, 1.63 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, put into 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-dichloropheny1)-P-(2- trifluoromethylphenyl ) -p- (2- trifluoromethylbenzoyloxy)acrylonitrile. The NMR spectrum data of this compound were as follows.

1H-NMR &ppm (Solvent: CDCl3/400 MHz) 7.21-7.45(m,3E), 7.49-7.88(m,8H) 2) 6.13 g of a-(2,4-dichloropheny1)-P-(2- trifluoromethylphenyl ) -p- (2- trifluoromethylbenzoyloxy)acrylonitrile obtained in the above step, was, 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 put into water, and the aqueous layer washed with methylene chloride was weakly acidified 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)- -hydroxy- -(2- trifluoromethylphenyl)acrylonitrile (after-mentioned Intermediate No. II-4) having a melting point of from 182

to 1830C. The NMR spectrum data of this compound were as follows.

1H-NMR Sppm (Solvent: CDC13/400 MHz) 5.81(s,lH), 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 was added under cooling with ice to a mixture comprising 0.30 g of a- (2,4-dichlorophenyl)- -hydroxy- -(2- trifluoromethylphenyl)acrylonitrile, 7 ml of dichloroethane and 93 mg of triethylamine. Then, the mixture was 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 from 114 to 1160C. The NMR spectrum data of this product were as follows.

1H-NMR dppm (Solvent: CDC13/400 MHz) 1.14(t,3H), 2.75-2.94(m,2H), 7.40(dd,lH), 7.47(d,lH), 7.57(d,1H), 7.71-7.78(m,2H), 7.85-7.89(m,2H) PREPARATION EXAMPLE 3 Preparation of a-(2,4-dichlorophenyl)-P- methylsulfonyloxy- -(2-trifluoromethylphenyl)- acrylonitrile (after-mentioned Compound No. a-55)

93 mg of triethylamine was added to a mixture comprising 0.30 g of a-(2,4-dichlorophenyl)-P-hydroxy-P- (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 (developing 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.

1H-NMR dppm (Solvent: CDC13/400 MHz) 2.68(s,3H), 7.38(d,lH), 7.46(d,lH), 7.54(s,lH), 7.70- 7.77(m,2H), 7.84-7.89(m,2H) PREPARATION EXAMPLE 4 Preparation of a-(2,4-dichlorophenyl)-p-(n- propylsulfonyloxy)- -(2-trifluoromethylphenyl)- acrylonitrile (after-mentioned Compound No. a-67) (Process 1) 93 mg of triethylamine was added to a mixture comprising 0.30 g of a-(2,4-dichlorophenyl)-P-hydroxy-P- (2-trifluoromethylphenyl)acrylonitrile and 7 ml of dichloroethane. Then, 0.13 g of n-propanesulfonyl chloride was 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 (developing 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.

1H-NMR Sppm (Solvent: CDC13/400 MHz) 0.87(t,3H), 1.52-1.64(m,2H), 2.65-2.73(m,1H), 2.79- 2.86(m,lH), 7.40(dd,lH), 7.47(d,1H), 7.57(d,lH), 7.71-7.78(m,2H), 7.85-7.89(m,2H) PREPARATION EXAMPLE 5 Preparation of a-(2,4-dichlorophenyl)-P-(n- propylsulfonyloxy)- -(2-trifluoromethylphenyl)- acrylonitrile (after-mentioned Compound No. a-67) (Process 2) 2.22 g of triethylamine was added to a mixture comprising 5.60 g of a-(2,4-dichlorophenyl)-P-hydroxy-P- (2-trifluoromethylphenyl)acrylonitrile and 50 ml of dichloroethane. Then, a mixture comprising 2.90 g of n- propanesulfonyl chloride and 10 ml of dichloroethane, was dropwise added thereto. After completion of the dropwise 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 (developing solvent: ethyl acetate/n-hexane = 1/6) to obtain 2.8 g of the desired product having a melting point of from 95 to 960C.

PREPARATION EXAMPLE 6 Preparation of a- ( 4-chlorophenyl)- -(n-butylsulfonyloxy)- -(2-trifluoromethylphenyl)acrylonitrile (after-mentioned Compound No. a-156) 1) A mixture comprising 6.19 g of 2- trifluoromethylbenzoyl chloride and 15 ml of toluene, was dropwise added with stirring at room temperature to a mixture comprising 3.0 g of 4-chlorophenylacetonitrile, 30 ml of toluene, 3.0 g of triethylamine and 0.1 g of 4- dimethylaminopyridine. After completion of the dropwise addition, the mixture was reacted for 8 hours under reflux.

After completion of the reaction, the reaction mixture was cooled, put into 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)- -(2-trifluoromethylphenyl)- -(2-trifluoromethylbenzoyloxy)acrylonitrile.

2) 3.08 g of a-(4-chlorophenyl)-P-(2- trifluoromethylphenyl)- -(2-

trifluoromethylbenzoyloxy)acrylonitrile obtained in the above step was, without purification, dissolved in 40 ml of ethanol. A mixture comprising 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 put into water, and the aqueous layer washed with methylene chloride was weakly acidified 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 1.68 g of a-(4-chlorophenyl)- -hydroxy- -(2-trifluoromethylphenyl)acrylonitrile (after-mentioned Intermediate No. II-2) having a melting point of from 146 to 1480C. The NMR spectrum data of this product were as follows.

1H-NMR dppm (Solvent: CDC13/400 MHz) 7.41(d,2H), 7.58-7.68(m,5H), 7.75(m,lH) 3) 86 mg of triethylamine was added to a mixture comprising 0.25 g of a-(4-chlorophenyl)-P-hydroxy-P-(2- trifluoromethylphenyl)acrylonitrile and 8 ml of dichloroethane. Then, a mixture comprising 0.133 g of n- butanesulfonyl chloride and 2 ml of dichloroethane, was dropwise added thereto. After completion of 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 having a melting point of from 63 to 640C. The NMR spectrum data of this product were as follows.

1H-NMR Sppm (Solvent: CDC13/400 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) PREPARATION EXAMPLE 7 Preparation of a- ( 4-bromophenyl)- -(ethylsulfonyloxy)- - (2-trifluoromethylphenyl)acrylonitrile (after-mentioned Compound No. a-21) 1) A mixture comprising 17.55 g of 2- trifluoromethylbenzoyl chloride and 30 ml of toluene, was dropwise added with stirring at room temperature to a mixture comprising 15.0 g of 4-bromophenylacetonitrile, 120 ml of toluene, 8.52 g of triethylamine and 0.5 g of 4-dimethylaminopyridine. After completion of the dropwise addition, the mixture was reacted for 4 hours under reflux.

After completion of the reaction, the reaction mixture was cooled, put into 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 21.25 g of a-(4-bromophenyl)- -(2 trifluoromethylphenyl)- -(2- trifluoromethylbenzoyloxy)acrylonitrile.

2) 21.25 g of a-(4-bromophenyl)- -(2- trifluoromethylphenyl)- -(2- trifluoromethylbenzoyloxy)acrylonitrile obtained in the above step was, without purification, dissolved in 60 ml of ethanol. Then, a mixture comprising 2.36 g of sodium hydroxide and 15 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 put into water, and the aqueous layer washed with methylene chloride was weakly acidified 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 9.52 g of a-(4-bromophenyl)-P- hydroxy- -(2-trifluoromethylphenyl)acrylonitrile (after- mentioned Intermediate No. II-3) having a melting point of from 168 to 1730C.

3) 91 mg of triethylamine was added to a mixture comprising 0.30 g of a-(4-bromophenyl)-P-hydroxy-P-(2- trifluoromethylphenyl)acrylonitrile and 8 ml of dichloroethane. Then, a mixture comprising 0.11 g of ethanesulfonyl chloride and 2 ml of dichloroethane, was dropwise added thereto. After completion of 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 = 1/4) to obtain 0.14 g of the desired product having a melting point of from 131 to 1320C. The NMR spectrum data of this product were as follows.

1H-NMR &ppm (Solvent: CDC13/400 MHz) 1.23(t,3H), 2.85(m,2H), 7.56-7.62(m,4H), 7.71(m,2H), 7.83(m,2H) PREPARATION EXAMPLE 8 Preparation of a- ( 4-bromophenyl)- -(n-propylsulfonyloxy)- -(2-trifluoromethylphenyl)acrylonitrile (after-mentioned Compound No. a-22) 60 mg of triethylamine was added to a mixture comprising 0.20 g of a-(4-bromophenyl)-P-hydroxy-P-(2- trifluoromethylphenyl)acrylonitrile and 6 ml of dichloroethane. Then, a mixture comprising 77 mg of n- propanesulfonyl chloride and 2 ml of dichloroethane, was dropwise added thereto. After completion of 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 = 1/9) to obtain 0.10 g of the desired oily product. The NMR spectrum data of this product were as follows.

1H-NMR Appm (Solvent: CDC13/400 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) PREPARATION EXAMPLE 9 Preparation of a-(4-bromophenyl)-(?-(n-butylsulfonyloxy)- -(2-trifluoromethylphenyl)acrylonitrile (after-mentioned Compound No. a-23) 60 mg of triethylamine was added to a mixture comprising 0.20 g of a-(4-bromophenyl)- -hydroxy- -(2- trifluoromethylphenyl)acrylonitrile and 6 ml of dichloroethane. Then, a mixture comprising 85 mg of n- butanesulfonyl chloride and 2 ml of dichloroethane, was dropwise added thereto. After completion of 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 = 1/9) to obtain 70 mg of the desired oily product. The NMR spectrum data of this product were as follows.

1H-NMR &ppm (Solvent: CDC13/400 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) PREPARATION EXAMPLE 10 Preparation of a- ( 4-chlorophenyl ) -P- (dimethylthiocarbamoyloxy)- -(2-trifluoromethylphenyl)- acrylonitrile (after-mentioned Compound No. a-316) A mixed solution comprising 0.42 g of dimethylthiocarbamoyl chloride and 5 ml of acetonitrile, was dropwise added at room temperature to a mixed solution comprising 1.0 g of a-(4-chlorophenyl)-P- hydroxy- -(2-trifluoromethylphenyl)acrylonitrile, 0.47 g of triethylamine, a catalytic amount of 4- dimethylaminopyridine and 20 ml of acetonitrile. After completion of the dropwise addition, the mixture was reacted for 2 hours at 500C.

After completion of the reaction, acetonitrile was distilled off under reduced pressure. Ethyl acetate and water were added to the residue to carry out extraction.

The organic layer was washed with water and a saturated sodium chloride aqueous 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 = 1/4) to obtain 0.82 g of the desired product having a melting point of 137.90C. The NMR spectrum data of this product were as follows.

1H-NMR &ppm (Solvent: CDC13/400 MHz) 3.10(s,3H), 3.22(s,3H), 7.35-8.15(m,8H) PREPARATION EXAMPLE 11 Preparation of a-(4-chlorophenyl)-P-(S- ethyldithiocarbonyloxy) -P- ( 2-trifluoromethylphenyl ) - acrylonitrile (after-mentioned Compound No. a-306) A mixed solution comprising 500 mg of a-(4- chlorophenyl)- -hydroxy- -(2- trifluoromethylphenyl)acrylonitrile and 2 ml of N,N- dimethylformamide were dropwise added under cooling with ice to a mixture comprising 68 mg of 60% sodium hydride and 10 ml of N,N-dimethylformamide. After completion of the dropwise addition, the mixture was gradually returned to room temperature, and stirring was continued until generation of hydrogen gas completed. Then, the mixture was again cooled with ice, and a mixed solution comprising 240 mg of ethyl chlorodithiocarbonate and 2 ml of N,N-dimethylformamide, was dropwise added. After completion of the dropwise addition, the mixture was reacted for 2 hours at room temperature.

After completion of 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 a saturated sodium chloride

aqueous 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 380 mg of the desired product having a refractive index nod27 .2 of 1.5612. The NMR spectrum data of this product were as follows.

1H-NMR dppm (Solvent: CDC13/400 MHz) 1.29(t,3H,J=7.80 Hz), 3.08(q,2H,J=7.80 Hz), 7.01- 7.93(m,8H) PREPARATION EXAMPLE 12 Preparation of a-(4-chlorophenyl)-P- (diethylaminosulfonyloxy)- -(2-trifluoromethylphenyl)- acrylonitrile (after-mentioned Compound No. a-286) 0.18 g of triethylamine was added to a mixture comprising 0.3 g of a-(4-chlorophenyl)-P-hydroxy-P-(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 put into 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 silica gel column chromatography (developing solvent: ethyl acetate/n-hexane = 15/85) to

obtain 78 mg of the desired oily product. The NMR spectrum data of this product were as follows.

1H-NMR &ppm (Solvent: CDC13/400 MHz) 1.05(t,6H), 3.06(m,4H), 7.42(d,2H), 7.57(d,2H), 7.63- 7.80(m,4H) PREPARATION EXAMPLE 13 Preparation of a-(4-chlorophenyl)-P-(S- methyldithiocarbonyloxy)-p-( 2-trifluoromethylphenyl)- acrylonitrile (after-mentioned Compound No. a-305) A mixed solution comprising 800 mg of a-(4- chlorophenyl)- -hydroxy- -(2- trifluoromethylphenyl)acrylonitrile and 2 ml of N,N- dimethylformamide were dropwise added under cooling with ice to a mixture comprising 110 mg of 60% sodium hydride and 10 ml of N,N-dimethylformamide. After completion of the dropwise addition, the mixture was gradually returned to room temperature, and the stirring was continued until generation of hydrogen gas completed. Then, the mixture was cooled again with ice, and a mixed solution comprising 340 mg of methyl chlorodithiocarbonate and 2 ml of N,N-dimethylformamide, was dropwise added thereto.

After completion of the dropwise addition, the mixture was reacted for 2 hours at room temperature.

After completion of 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

sodium chloride aqueous 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 having a refractive index no39.4 4 of 1.5930. The NMR spectrum data of this product were as follows.

1H-NMR dppm (Solvent: CDC13/400 MHz) 2.47(s,3H), 2.53(s,3H), 7.07-7.99(m,8H) PREPARATION EXAMPLE 14 Preparation of a-(4-chlorophenyl)-P- <BR> <BR> <BR> <BR> <BR> <BR> (dimethylaminosulfonyloxy)- -(2-trifluoromethylphenyl)- acrylonitrile (after-mentioned Compound No. a-218) 1.25 g of triethylamine was added to a mixture comprising 2.0 g of a-(4-chlorophenyl)-P-hydroxy-P-(2- trifluoromethylphenyl)acrylonitrile 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 obtained residue 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 from 110 to 1120C. The NMR spectrum data of this product were as follows.

1H-NMR dppm (Solvent: CDC13/400 MHz) 2.66(s,6H), 7.43(d,2H), 7.60(d,2H), 7.67-7.82(m,4H) PREPARATION EXAMPLE 15 Preparation of a-(4-chlorophenyl)-P-(ethyldithiooxy)-P- (2-trifluoromethylphenyl)acrylonitrile (after-mentioned Compound No. a-488) 1) 0.109 g of sulfur dichloride was added to a mixture comprising 0.25 g of a-(4-chlorophenyl)-P-hydroxy-P-(2- trifluoromethylphenyl)acrylonitrile and 10 ml of ethyl ether. Then, a mixture comprising 67 mg of pyridine and 10 ml of ethyl ether, was dropwise added thereto at -100C, and the mixture was returned to room temperature and reacted for 3 hours.

After completion of the reaction, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 0.30 g of a-(4- <BR> <BR> <BR> <BR> <BR> chlorophenyl)- -chlorosulfenyloxy- -(2- <BR> <BR> <BR> <BR> <BR> <BR> trifluoromethylphenyl ) acrylonitrile.

2) 0.30 g of a- ( 4-chlorophenyl)- -chlorosulfenyloxy- - (2-trifluoromethylphenyl)acrylonitrile obtained in the above step was, without purification, dissolved in 10 ml of dichloroethane. Then, 58 mg of ethanethiol was added thereto, and then 94 mg of triethylamine was added thereto under cooling with ice. The mixture was returned to room temperature and reacted for 1 hour.

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, 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 = 15/85) to obtain 0.20 g of the desired oily product. The NMR spectrum data of this product were as follows.

1H-NMR dppm (Solvent: CDC13/400 MHz) 1.24(t,3H), 2.62-2.79(m,2H), 7.12(d,lH), 7.43(d,2H), 7.49(t,lH), 7.60(d,2H), 7.74(d,lH) Now, typical examples of the compound of the present invention of the above formula (I) will be shown in Tables l-a, l-b, l-c and l-d, and typical examples of the intermediate compound of the formula (II) will be shown in Table 2. These compounds can be synthesized in accordance with the above-described Preparation Examples or the above-described various methods for producing the compound of the present invention or its intermediate compound.

Table I-a Comp. (R3)m C7 L Physical R R1 zit (K2) Property Y point) 74 a-l -SO2CH2CH3 F3C < 00- 3c 102 a-2 0 -S0211(CH3)2 0 104C 98 ~ 100"C C1/ a-5 t Cl -CO(CH2)2CH3 Oily Cl a-6 t Cl -CO(CH2)2CH3. Cl Oily ci CI CI a-7 HzCl -COCH(CH3)2 Oily CI 83 a-8 OCI -COC(CH3)3 Cl Hz 83~ 84°C Cl a-9 t Cl -COC(CH3)3 Cl Hz 0 CI Oily ci CI CI a-10 CI -C0(CIi2)2CH3 Oily F3C Table I-a (Continued) Comp. (R3)"7 Physical No. CO R, (R2)1 Property (Ielting Doint) 86- a-14 ClO -S02(CH2)2CH3 0 89C FBC' a-15 Br- -COCH3 a-17 Br- -CO(CH2)2CH3 a-17 Br C0(C112)2CH3 F3C a-18 Br + -COCH(CH3)2 ¼ F3C a-19 Br + -COC(C113)3 ¼ F3C 105 a-2O 2 -SO2CH3 F3C > 112C F3 a-21 Br + -S02CH2CH3 F3C 131 32 a-22 Br + -S02(CH2)2CH3 FBCHz¼ j Oily F3C Table I-a (Continued) Physical Property No. (R3) 0 K1 %½(K2)1 (Melting point) S02(CH2)3CH3 a-24 CIci Cl -COSCH3 F3C Hz Oily a-25 C1- C1 -COSCH2CH3 F3C Hz Oily a-26 < Cl -CH3 v a-27 C1- Cl -CH2CH3 F3C 133C a-28 CI1 Hz -CH2CF3 ¼ 123C E-isomer a-29 CIOc1 -CH2OCIi3 0 99 Cl F3C 103C a-30 CI1 Cl -COCH3 ½K Hz 140°C CI C1Th1 -COCH3 ¼ - C1 F3 CI a-32 CITh1 -COCH3 Cl X CI a-33 C1Th1 -COCH3 ¼ I:3c a-34 Cl Mi -C0CH2CU3 ciM 9394C Table I-a (Continued) Comp. ( R 3) L Physical K1 CR2) Property No. y (Melting point) a-35 Cl C1M1 -c0CH2cH3 ¼ F3C a-36 < Cl -COCH2CH3 Cl X a-37 CIM1 -COCH2CH3 F3C -, X F3C a-38 C1 -CO(CH2)2CH3 CIM 596OC a-39 cim%1 -Co(cH2) 2cn3 ¼ Oily PlC a-40 C1- C1 N -CO(CH2)2CH3 a-42 < -COCH(CH3)2 92 a-42 -COCii(CH3) 2 0 94C CI CI a-43 C1- -C0cH(CH3) 2 ¼ Oily F3C a-44 c1Th1 -COCH(CH3)2 Cl CI a-45 Cl < -COCH(CH3)2 F3C X Plc a-46 CI- C1 -CO(CH2)3CH3 Cl Hz Oily Table I-a (Continued) ComP. ( R 3)m . Physical No. (R1)m K ½y(K2)1 Property Y (Melting point) a-41 C1- -coc(cH,>, Oily a-49 Cl C1 -COC (CH3)3 X ci a-50 C1 C1 -COC(CH3)3 F3C X PlC a-51 < Mi -CO(CH2)2CI Cl C1- ci a-52 CIM1 Ci -CO(CH2)2CI p3c¼ Z -isomer a-53 C1 -S02C111 Q < 02CH3 121 ci Cl 123C E -isomer -SO1CHJ CI Hz Cl - SU2CH3 C1 117C a-55 CI Mi -S02CH3 ¼ Oily -CI F3 CI a-56 Cl -S02CH3 F3CO a-57 CI < -SO2CH3 ¼ Amorphous 02N a-58 C1 Cl -SO2CH3 NC¼ Table I-a (Continued) Comp. ( R 3)m 7 C Physical Property (Melting point) a-59 3-59 )- Cl -SO2CH3 H3CO2S a-60 Cl JO1 -SO2CH3 C1 X a-61 < -S02C111 ¼ F1C a-62 t Cl -S02CH2CH3 Ci E-isomer a-63 114- -302C112C111 0 114 116"C a-64 Hz Cl -S02CH2CH3 ¼ ci a-65 CIM1 S02 CIi2CH1 ¼ plc a-66 cIM1 302 (c112)2c113 Cl C1 E-isomer a-67 CIOc1 -SO2(CH2)2CH3 < 95 PlC 96C a-68 CI- --JN, C C1 F3 CI 109 a-70 Ci Hz -SO2CH(CH3)2 F3C Hz109 112°C Table I-a (Continued) Physical Comp. ( R 3) m (K2) Physical No. < RI (R2)1 HzY R 2 ) I (Melting point) -S02(CH2)3CH3 3 a-71 C1 a-73 Ci M1 -S02(CH2)3CH3 Cl X C1' a-74 C1 -SO, (CI,) 3CH3 J cl FBC' a-77 Ci M1 -SO2 CF1 ¼ Hz Oily ci a-78 t Cl -S02CF3 ¼ > nDl'5430 Plc - a-79 < Cl -S02CH2CF3 ¼ a-80 HzC1 -SO2CH= CH2 F3C < 120°C a-81 C1 Cl -S02CH2CH= CH2 ¼ Plc a-82 CI-so, -SO2-CH1 F3C 167"C PlC Table I-a (Continued) Comp. (R3)m C Physical No. F < K1 y½(K2)1 Property C1 F 3 CI F - F a-85 F - pP -S02CH1 p1c¼ F3C/ a-86 F,C-COCH, a-88 F3C + -COCH2CH3 Cl ci a-89 F3C 4 -COCH2CH3 F3C p1c¼ a-90 F3C Hz -CO(CH2)2CH3 ¼ Ci a-91 F3C + -CO(CH2)2CH3 ¼ plc a-92 F3C + -COCH(CH3) 2 C C1' a-94 F3C + -COC(CH3)3 Cl < Table I-a (Continued) Physical Comp. (R3)m m y½CK2)1 Property Property 1 7r No. 1 7 (Melting a-97 F3C < -S02C113 ¼ "5½25C a-98 FBC+ -SO2CH2CH3 CI ¼ a-99 F3C Hz -S02CH2CH3 F3C 68 ¼ a-lO() F3C 4 -SO2(CH2)2CH3 Cl a-101 F3C Hz -S02(CH2)2CH3 F3C¼ ¼ a-102 F2C -S02(CH2)1CH2 CI a-103 F3C Hz -SO2(CH2)3CH3 F3C¼ a-104 F3CM -COCH3 0 CI Cl a-105 F3C Hz -COCH3 ¼ -ci F3C a-106 F3C Hz -COCH2CH3 ¼ Cl CI Table I-a (Continued) Physical c,,, (R3)m L Physical a-107 F3C K -COCH2CH3 (Melting point) F3CMi -C0CCH3) 2CH3 ¼ a-109 P3C- a-llO F3C Hz -C0Ct}(CH3) 2 CI ¼ CI a-lll F3CM Hz -COCH(CH3)2 ¼ CI F3C a-112 F3C < -C0C(CH1)3 ¼ CI Cl a-113 F3CM Hz -COC(C113) ¼ CI 113 F3C an114 F3C Hz -802CH3 CI ¼ CI a-115 F3CM1 -SO2CH3 F3C a-116 F3C < -SO2CH2CH3 Cl ¼ CI a-i 17 F3C -SO2CH2CH3 F3C¼ CI ailS F3C -S02(CH2)2CH3 -ci FBC a Cl Table I-a (Continued) Physical No. ( R 3) me RI(R2)1 Property (ILlelting point) a-119 F3C--7 a-12l P1C -802 (C112)1C111 ¼ ci F3C-C1 plc a-122 F3C- 7 a-124 02N Hz -COCH2CH3 p1c¼ -CO(CH2)2CH3 a-125 OrN--(O FJI a-126 OnN 125 ~ a-128 02N0 -SO2CH3 F3C Hz 128°C PlC a-129 02N + -SO2CH2CH3 F3C X a-130 02N + -S02(CH2)2CH3 p1c¼ Table I-a (Continued) Comp. (R3)m Physical No. L1 ~(R2)1 Property VJ (Melting a-132 | Cl ci¼% -COCH3 p1c¼ NO Ft ' a-133 C1--7 COCH2CH3 iCN02 FI( a-134 C1 a-135 C1 Hz -COCH(CH1) 2 ¼ NO2 plc a-136 C1 ¼ NO2 CI -COC(CH1)1 plc 130 a-137 ClO -SO2cI}1 0 133C NO2 F1C a-138 HzCI -SO2CH2CH3 ¼ NO2 plc a-139 CI 802 (CH2)2CH1 ¼ NO2 ; C1 plc a-140 C1 -S02(CH2)3CH3 a-142 02N < -COCH2 CH1 ¼ CI PlC Table I-a (Continued) Physical Property No. (R1) K1 y½(R2)1 (Melting point) a-143 02N Hz -CO(CH2)2CH3 ¼ ci plc a-144 02N Hz -COCH(CH3) 2 F3C CI plc F3C\/ a-147 02N -S02CH2CH3 ¼ a-148 plc F,C'I a-150 H3CS < Cl -COC(CH3)3 F3C > 11. 8 a-151 -coc(cH,>, 1.5432 F v H3C02S 141.3 ":: a-153 Ci -cOcll1 ¼ Oily PlC a-154 | CI + -SO2N(CH3)2 F C X Table I-a (Continued) Comp. (R 3)m 7 L Phvsical ~(R2)1 Property I \ 63- a-156 clO -802(CH2)1CH1 0 640C plc a-157 Cl + -CS2C=-CH p1c¼ a-158 t Cl -SO2CH3 F3C < 90 - a-159 Cl > -SO2CH1 FBCp1c¼ Oily C1- FO 77- a-160 CI- -COCHB 80"C 83- a-162 ClO -COCH(CH3)2 840C plc a-163 C1 -S02(C112)4CH1 F3C Oily a-164 C1 < -SO2CH=CH2 FBCp1c¼ 76°C ¼ a-165 C1 + SO2 CF1 ) Oily a-166 CI -SO2CH1CF1 X01 102 105"C Table I-a (Continued) Physical Comp . | ( R 3) m Property No. t r ( R K1 ¼;½(K2) (Melting point) a-167 CI -S02(CH2)3CI p1c¼ Oily a-168 Cl m -SO2CH3 H CX 95 100°C p 121 a-169 CIG Hz -SO2CH3 p0 123C a-170 C1- -S02CH3 Oily 0 a-172 Cl + -SO2CH3 p1c½)N 101.9 V 77 a-173 F --(O -S02N(CH3)CH2CH3 p1c¼ 79C a-174 F + -COCH3 F3CX FB( a-175 F -SO2CH1 ¼ plc a-176 F X Hz -SO2CH2CH3 p1c¼ lOZ C a-177 F -S02(CH2)2CH3 3 102"C 83 all78 F X -SO2 (CH2)3CH3 F3CX 85C Table I-a (Continued) Comp. (R3)m L Physical No. No. (R1)m K1 y½(K2)1 (Melting ooint) a-179 Br -COSCHJ0 F3C Hz Oily plc a-180 Ur -S02(CH2)4CH1 ¼ Oily plc plc 112 a-183 10 -SO2CH1 0 113C 126~ plc 126- a-184 I- 128"C a-186 I Hz -S02(CH2)3CH3 F3C 73 75C FJC' a-187 ciM1 802 (CH2)3CI p1c¼ Oily Z-isomer a-188 CI SO2 (CH2)2CH1 0 75 Cl PlC 77"C Z-i somer a-189 < Cl -SO2CH2CH3 F3C Hz Oily Ci plc 96 a-l90 CCI 9 -SO2CH3 p1c¼ 98 Table I-a (Continued) Physical Comp. RI L -(R2)1 Property No. Ce K y½½(K2)1 (Melting Y point) a-191 F -S02CH2CH3 F3C Hz 84.2 etc plc a-192 CM -SO2N(CH3)CH2CH3 F3C p1c¼ a-193 e F -COCH3 p1c¼ F FIC'91 81- a-194 ClO -802C111 0 84"C F PlC 122 a-195 CiOp -SO2CH2CH3 0 125C PlC 65 a-196 e SO2 (CH2) 2CH1 0 66"C p plC a-197 e -S02(CH2)3CH3 Oily Oily -F F3 a-198 Ci --(O) + C111 p CH3 plc a-199 + Cl -COCH1 p1c¼ 103 a-200 e M1 -SO2CH2CH3 F3C < 105C 80- a-201 HzCl 802 (C112) 2CH1 3 Hz 82C a-202 HzCl -S02(CH2)3CH3 F3C 5052C Table I-a (Continued) (R1)m Physical Comp. ( K X <( R 2)l [ nv 1 t llq (K) Property No. I Y2 (Melting point) 133 a-203 H3C + -SO2CH3 F3C Hz 136C PlC a-204 (H3C)2CH + -SO2CH3 FBCp1c¼ 91°C a-205 (H3C)3C Hz -S II, 101 a-206 (H3C)3C 4 -SO2CH3 F3C Hz 103C F1c 68 a-207 (H3C)3C Hz -S02(CH2)2CH3 FBC> 70"C F3C' 127- /7 -CH2CH2CI 73"C a-210 ClO -CH2CH2Ci 0 73C PlC 68 a-211 C1 < -CH2OCH1 F3C Hz 72C a-212 Cl 4 -CH20CH2CH3 FBC Hz¼ Oily a-213 Cl + -CH2CH20CH3 P1C¼ 82 a-214 ClO -SO2CH(CH1)2 0 84C PlC Table I-a (Continued) Physical Property Comp. (K1)m No. 5 ( R K1 5 R , yK2I (Melting point) a-215 Cl -SO2CH2CH(CH1)2 p1c¼ 8083C F3 CI a-216 Cl CI--Lt + CH3 PlC a-217 C l + -S°2 C (CH3)3 F3C < a-21 C1 -so,c(cH,>, F3 C/ 110- I 112"C a-219 F + -S02N(CH3)2 F3C 8486C F3C' 120- a-220 Br--(O) -S02N(CH3)2 191 121"C a-222 Cl M1 -CH2CH2CI F3C -CH2 88 2 90°C E-isomer a-223 C1 Hz -CH20CH2CH3 ¼ 86- Cl PlC 88"C Z-isomer a-224 CI -CH2OCH2CH1 0 77 PlC SOC 111 a-225 ClOci -CH2CH20CH3 F3C Hz 113°C C1 F3C a 226 C1 M1 | FBC92DC E8i;1%o;;; Table I-a (Continued) Physical Comp. (R3)m e <( R 2)l Jr Property No. I Y21 (Melting point) a-227 CiM1 Cl -SO2CH2CH(CIi1) 2 ¼ Oily PlC a-228 -SO2CH-CH2CH1 ¼ a-228 Cl < CH3 F3C > a-229 < Cl -SO2C(C111) 1 ¼ - ci F 3 CI 137- a-232 -SOPCHB 95.3 "C a-232 -302CH1 pICO 95.3 C a-233 -S02CH2CH3 cO Oily a-235 Cl < \ -(CH2)2CH3 F3CX t Oily a-236 Ci -CH(C113) 2 ¼ 81 82C plc a-237 Cl + -(CH2)3CH3 ¼ Oily plc a-238 C1 + -CH2CH2F Oily plc Oily Table I-a (Continued) Physical No. Co)f(R2)1 Property No. (K1) K ½y(K2)l (Melting point) a-239 Cl + -CH2CF3 ¼ Oily PlC a-240 CI- -CH2CH=CH2 F3C Hz Oily a-241 C -CH2C(CI)=CH2 ¼ plc a-242 CI + -CH2C(CI)=CHCI FBCp1c¼ a-243 Cl + -CH2CCH F3C F3CI a 244 C1-COCHIOCH, F3C Oily Oily a-246 Ci + -COCH2CH=CH2 p1c¼ a-247 Ci Hz -COCH2C(CI)=CH2 ¼ F1C a-248 Cl Hz -COCH2 C--CH ¼ PlC a-249 C1 + -COCH2CCC I p1c¼ a-250 Cl + -CO2CH3 F3C < 63°C F1C Table I-a (Continued) c,,, . (R3>m " $EHBfR point) No. Co > I -C02CH2CH3 Oily a-251 C1--(0)- a-255 Cl 4 - CO p1c¼ F3C > 135 138°C a-256 Cl c0C{y F3C Hz 109 111"C plc a-257 C1 + \ -CO ¼ Oily PlC a-258 Cl -cOci F3C Hz 106 109°C109"C a-259 C1 -- CO 121c¼ a-260 C1 Hc0lC p1c¼ F3C < 123 124°C124"C . . a-261 C1 COcIIl CH3 F3C < 127"C PlC 110 a-262 Cl OCH3 p1c¼ 113C Table I-a (Continued) - c,,,. (R3>m C Physical No. (R1)m K1 y½(K2)1 (Melting point) a-263 Cl + - CO2 p1c¼ FBC Hz Oily a-264 CI -CO2--NO2 p1c¼ FJC' -COr a-265 C1- a-267 Ci + - COUCH2 4 F3C Hz 85 ~ 87°C plc a-268 CI + -COCH2 + Cl ¼ PlC ¼ a-269 CI -COCll2CiIl PlC a-270 CI + - COSCH2 p1c¼ a-271 C1-t -co a-273 CI -CONt ¼ a-273 C1-nu)~ I a-274 Cl + -SCH3 FBCp1c¼ Oily Table I-a (Continued) Comp . (R3)m C7 C "I Physical Property (Melting point) -SOCHJ a-277 Ci Hz -S02CH, H3CO/W 153.9 °C a-278 CI -802C111 p1co¼ Oily a-279 Cl + -SO2CH20CH3 p1c¼ a-280 Cl + -SO2CH2C(CI)=CH2 p1c¼ P1C' a-282 Cl + -SO20CI12CH3 F3C > 101°C a-283 Cl + -SO2SCH2CH3 ¼ a-284 Ci Hz -SO2NH(CH2)2CH3 P1C¼ a-285 CI + -SO2NHC(CH3)3 p1c¼ a-286 C1 Hz -SO2N(CH2CH3)2 FBCp1c¼ Oily Table I-a (Continued) Physical Comp. ( R 3 ) K -(K) Property No. I L-i71/R 2)1 (Melting Y point ) I S02N(CH2CH3)2 a-287 C1 \v~/ -SO2N-(CH2)3CH3 a (CH2)3CH3 F3C' /7 151- a-290 Cl + - --SO2-0 155"C a-291 Cl 4 -SO2 - 4 -CH3 F3C > 152 156°C a-292 CI 4 - SO 4 F3C p1c¼ a-293 Cl 4 -SO2O--CH1 ¼ PlC a-294 C1 + - SO2S 4 F3C p1c¼ a-295 C1 -SO2CH2 p1c¼ a-296 Cl --S02CH z- p1c¼ a-297 Cl + -SO2CH2 W p1c¼ 164- 164 a-298 CiG 802 -SO2N N F3C Hz 164 167"C PlC Table I-a (Continued) Physical Comp. ( R 3) m <\ < ( R 2)1 Property No. R I k8) (Melting 1 point] I -SOn":> rc' Oily a-301 Cl + -CSCH1 ¼ PlC a-302 Cl Cloth -CSCH2CH3 PlC a-303 Cl + -CSOCH3 PlC X Oily a-304 Ci + -CSOCH2CH3 ¼ Hz Oily plc a-305 C1- -CS2CH3 ,D39. 4 FJL 1. 5930 a-307 Cl + -CS2CH(CH3)2 F3C < nDl 3 5824 a-308 C1 m -C82(C112)1CH1 ¼ 80.3 C F1C a-309 CI -CS2CH2CF1 p1c¼ a-310 CI -CS2CH2CH=CH2 ¼ rID 2 6. plc 1. 6040 Table I-a (Continued) c,,,. (R3)m Physical No. KI LRI)I Property a-312 C1- -CS2CH2C=-CH ¼ a-313 Cl < -CS2CH2C -- Cl F3C < a-313 C1 -CS2CH2CCI a-315 C1 -CSNHC(CH3)3 a-315 Cl -CSNHC(CH1)1 PlC a-316 Cl W - -CSN(CH3)2 F3C Hz 137.9 °C 121 a-317 Cl O -CSN(CH2CH1) 2 0 123C PlC a-318 Cl < -C8 p1c¼ FBCHz Oily a-319 Cl < - CS0 p1c¼ FBCHz Oily a-320 J Cl --CSOO--ce, F3C a-321 Cl -CSO--OCH1 F1C¼ a-322 C1 -CS2- F1C¼ < F3C Hz 113.8 °C Table I-a (Continued) . Comp. (R3>m L Property No.~(R2)1 (Melting 1 point) --CS2--C1 nD3(). a-325 Cl + -CS2CH2 Hz F3C Hz 71.9 °C plc a-326 C1 + \ -CS2CH2 p1c¼ F a-327 Cl + -CS2CH2 W )¼cii1 PlC a-328 Cl I -CSN p1c¼ 129.6 .C an329 Cl -CSNO p1c¼ 125.8 C a-330 Cl + -CH2CN p1c¼ Oily F3C' a-331 C1 --CHa-o 116"C Ci -CH2 PlC a-332 Cl + - CH2 < FBCHz 74 ¼ 75,C PlC a-333 Cl + < F3C Oily a-334 Cl --CH22- 4 Hz 127"C PlC Table I-a (Continued) Comp. (R,) m e R , | (R3)m Physical Property No. K1 (K2 (Melting point) a-335 Cl cii2{½ F3C Hz 93 ~ 94°C a 336 Cl + - CH2 + F p1c¼ 10911C a-337 Cl < - CH2 4 CH2- F3C Hz 90 plc ¼ 140 a-338 Cl -CH2Br PlC l41C a-339 CI -CH2CH1 F3C '3fir37C F3C' a-340 C1 --CH2- CF3 98ooe a-341 C1 + - CH2 + NO2 FBCHz 125 130°C PlC C1 -CH2OCH2 < F3C Hz Oily plc a-343 CI -CH2OCH2 p1c¼ yhcH1 a-344 C1 --CH2CO- llO"C F3C' a-345 Cl + -CH2CO - + -Cl F3C a-346 Ci -CH2 CO- -CH3 Table I-a (Continued) Comp. (R3)m RI C93(Rz>l Physical No. Co Property (Melting point) a-348 CI CH2ffi%NO > Oily F3C/ a-349 Cl + - CH2 FJ a-350 Cl -cii2¼;½c1 F3C a-350 C1 F3 a-351 Cl + -CH2COCH3 ¼ Ci Cl + -CH2SOCH3 ¼ FsC a-353 C1 I \ Oily (0 > -CH2Si (CH3)3 a-355 F -COs p1c¼ a-356 F -SOCH1 ¼ PlC a-357 F -SO2CH2C--CIi p1c¼ FJL a 358 F + -SO2N(CH3)2 111CS¼ Table I-a (Continued) - p. K (K2) R, Property No. (Melting point) a-359 F + -SO2N(CH2CH3)2 FBCHz 45°C F3C' 45"C a-360 F- 59"C 58 (CH2)2CH3 F3C/ a-361 F --SO, /7 -OCFJ F3C' a-362 F -CS2CH2CH3 FJC nD31. o a-364 P -CSN(CH3)CH2CH3 p3c¼ a-365 F + - p1c¼ FBC Hz 127.9 °C a-366 F -CH2 p1c¼ 10104aC a-368 Br Hz -CH2CH3 FBCHz¼ Oily PlC a-369 Br < - CO+NO2 p1c¼ a-370 Br -SO2#$\ p1c¼ Table I-a (Continued) (K1) Physical Comp. m K1 (K) Property No. Y2l (Melting kr/S a-371 Br + -S02N(CH2CH3)2 F3C 7173C F3C' a-372 Br + l < 66°C -SO,N (CH2)2CH3 65- I 66"C a-374 Br + -CSCH20CH2CH3 ¼ a-374 Br--3 F3C' 1 a-375 Br -CS2CH2CH3 102 4 "C a-377 Br < -CSN(CH3)2 y½¼CH1 a-378 Br- -CSCH2- a 379 Br- -CS2CH2-> a-380 Br Hz -CS2CH2 CN F3C PlC a-381 Br -CSN p1c¼ 136.2 C a-382 Br ~ -CH2 Q p1c¼ FBCHz Oily Table I-a (Continued) Comp. ( R 3)m - L Physical Property No. (R1)m 0 K1 ¼%(K2)1 (Melting point) a-383 1 -COSCIl2 CP1 ¼ FlC¼ a-384 I + -SO2N(CH2CH1)2 PlC Oily a-385 -SO2SCH2 F1C¼ 154 a-386 1 + -SO2N 3 FBC> 154 155"C a-387 I + -CS2CH3 FBC> 130.2 °C Fgi 141- Z -isomer a-39O CIG -CH2OCU1 0 68 CI C1--(0) -CHOCHB plc 70C --CI a-391 | ClO Hz -CH2SCH3 Z 113 CI FsC 118C a-392 C1 -COC20CH3 FBCp1c¼ Oily a-393 CI -COSCH2CH=CH2 p1c¼ a-394 C1- -CO2CH1 F Oily PlC Table I-a (Continued) Physical Comp. R 3)m 7 L Physical No. (K1) K1 y½(K2)1 (Melting point) a-395 C1 Cl -CO2CH2CH3 p1c¼ Oily a-396 < C1 - cho < CN F3C CIM1 -CO ¼ a-397 C1--(0) plc -SDzCH3 I;3C/ a-398 CIM1 -CO2 p1c¼ FBCX Oily a-399 Cl < -SO2(CH2)3CH3 PlC Oily Ci CI ¼ < -SO2SCH2CH=CH2 -C1 F3C/ a-401 Cl Hz -SO2NH(CH2)2CH3 < a 401 C1 -(O) a-402 < Cl -SO2NHC(CH3)3 p1c¼ 124 a-403 Cl Hz -SO1N(CH2CH1) 2 > 124 125C Ci -SO2N-(CH2)2CH3 105 a-404 Ci 0 107"C CI (CH2)2CH3 F3C' -SO2N-(CI12)3CH3 a-405 C1 CI (CH2)3CH3 PlC a-406 CIM1 SO2 - t -CF3 p1c¼ Table I-a (Continued) Comp. (K1) Physical comp. (R 3)m C Physical No. e K1 (Melt na point) 120 a-407 ClO -SO2N 3 FBC l21C ci F1C a-408 C1- -SO2N p1c¼ a-409 t C1 -S02N U 0 CI m/ p PlC a-410 C1- C1 CSCHB a-412 C1-Qcl -CSOCHB a-413 Cl CIM1 -CSOCH2CH3 ¼ Oily plc a-414 Cl < -CS2CH3 ¼ flD1 plc 1. 5998 CH1 a-415 ClOci -CS2CH2CH3 0o0 a-416 C1 Cl -CSCH2C(CI)=CHCl F3C a-417 < ¼ -CSN(CH3)2 FBC 97 a-4l7 CIM -CSN(CH1) 2 1 98C a-418 CIM -CSN (CH2CH3) 2 ¼ Oily Ci PlC Table I-a (Continued) (K1)m Physical Comp. ( m m Rl XrÇ R 2) Physical No. COZY "' (R2)1 (Melting point) a-419 C1- F3C C --CHP F3 a-422 Cl C1M1 -CH2CO2CH1 p1c¼ 7780C -- cl F3 CI Z-isomer a-423 C1 -CH2S02CH3 161- -C1 F,C 163"C a-425 F < -CS2CH3 < nD2 G. 8 F F3C 1. 5680 a-426 F- -CSN(CH3)2 109.2 "C -F F3C' a-427 F- -CSNC 139.1 "C a-428 t F -SO2CH2CH(CH3)2 ¼ Hz Oily p plc 64 a-429 ClM -SO2N(CH3)2 F3C < ) 68C -F F3C a-430 Cl Hz -SO2N(CH2CH1) 2 ¼ 98C plc Table I-a (Continued) (K1)m (R3>m7 L Physical Comp. K R 3 ) m Hz r R 2), Property No. 0 1 Y2I (Melting point) a-431 C1- -CSN(CH,) 90"C a-432 (H3C)3C + -COSCH2CH=CC12 PlC F,C a-433 (H3C)3C > -S02SCH2CH=CC12 (H1C)1C -CSN(CH3)2 F3C a-436 -COSCH2C--CH F3C PlC a-437 F3C + -COSCH2C=CI p1c¼ a-438 P1CO Hz -COCH3 ¼ plc a-439 H3COS > -SO2CH2CH3 F3C > F3C\/ a-440 7¼ -SO2CH2CH3 F3C > Oily a-44l CI -CS2CH2CH1 p1c¼ ¼ a-442 HCv < -CSN(CH3)2 PlC Table I-a (Continued) Physical Comp. (R3)m e Property No. 1 21 (Melting point) a-443 CI¼ -COSCH1 ¼ Oily PlC a-444 CI coyw p1c¼ a-445 ciTh -CO-.1 Oily a-446 CITh CO N p1c¼ a-447 CITh + - CO p1c¼ a-448 Cl CITh 502 plc a-449 Cl ciTh SO2$ p1c¼ a-450 CITh -SO2N p1c¼ a-451 Cloth -CS2(CI12)2CH3 FBCp1c¼ 71.9 °C a-452 Cl + -CS2CH2CO2CH3 p1c¼ X 21.658625 a-453 Cl CITh -CS2CH2CO2CH2CH3 p1c¼ a-454 Th -CS2 CU2 p1c¼ Table I-a (Continued) Comp. (R3)m7 L1L(Rz)l Physical No. Co \- R I Property \ (Melting F3C' a-458 Br- -CS2CH2CO2CH3 ¼ a-459 f F Hz -SO2N(CH3)2 FBC> 118T a-460 j F Hz -SO2N(CH2CH3)2 FBCp1c¼ Oily a-461 | CIM -CS2CH3 > nD2s.2 p F PlC 1.5364 a-462 CITh | Cl e - cho FBC p1c¼ Oily a-463 CI- COcii1 F3C Hz 72~ 74°C -CO Cl W 3 FBCHz 155C a-464 CITh H:Cc0 p1c¼ 152 H1C 110 a-465 Cl -COCH1 p1c¼ Hz 113C a-466 C1- -CO + CH2CH3 F3C '04¼O6C PlC Table I-a (Continued) Physical No. RI No. (Kl)mM½ K1 ½y(K2)1 (Melting point) a-467 Cl e -C0 p1c¼ F3C a-468 C1- COS(CH2)2CH3 a-469 Cl + -CONHCH3 F3C < Oily a-469 C1 -CONHCH3 oily FBC' CU1 Cl + CH3 a-472 C1 - S F1c¼ FBCHz Oily 188 a-473 C1 -SO- -SO < FBCHz 191"C a-474 C1 I , FSC' a-476 C1 -SN(CH2CH3)2 F3C X P1C a-477 Hz Cl < -SN 3 FBCC1-sr a-478 CITh -SCH2CH3 ¼ F1C Table I-a (Continued) Comp. Physical comp. ( R 3) I Property No. el - (R2)1 (Melting oint) a-479 Cl + -S(CH2)2CH3 ¼ plc a-480 Cl Hz -SCH(CH3)2 ¼ a-481 Cl w -SC(CH3)3 ¼ PlC a-482 C1 -SCH2C1 ¼ plc a-483 C1 -SCHCI2 F3C a-484 C1 + -SCH20CH3 p1c¼ a-485 CiTh -SCH2SCH1 P1C¼ a-486 Cl + -SCH2N(CH3)2 p1c¼ a-487 CI- -S2CU1 ¼ a-488 C1- -S2CH2CH3 F3C Hz Oily plc a-489 Cl < -S2CH(CH3)2 p1c¼ a-490 ciTh -52C(CH1)1 ¼ plc Table I-a (Continued) Physical No. ( R 3)m < (¼¼(K2) Property point) point) a-491 CITh -SN(CH3)0CH3 ¼ Plc a-492 CI- -SN(CH2CH3)0CH3 CITh -SN(CH2CH1)OCH1 plc a-493 C1 -S2- F3C a-494 CITh - S2 4 Cl F3C a-495 C1 -S2- CH3 CH3 PlC a-496 C1 -S2Cpl ¼ plc a-497 Cl + -52 OCH1 OCH3 a-498 Cl < -SO2N(CH3)0CH3 ¼ PlC -SO2N- OCH1 a-499 CITh CiI2CU1 p1c¼ CH2CH3 F3C' a-500 CITh -SO2CH2N(CH3) 2 F3C . -S02(CH2)2N-CH3 a-501 Cl + CH3 F3C < CU1 a-502 Cl + -S°2 (CH2)20CH3 p1C¼ Table I-a (Continued) Physical Comp. (R3)m-7 J Property No. )2I ~(R2)1 (Melting Y oint) a-503 a-505 CITh j -SOn-C a-506 ClTh -SO ZN\ p1c¼ a 507 C1 -(O ) 7 0 a-509 Cl ciTh -S02-"NJ p1c¼ F3C/ a-510 C1 a-512 Cl + -SO2 < F3C 0 an513 Cl -502%)'N p1c¼ S a-514 Cl ciTh --SOn- p1c¼ Table I-a (Continued) ,,,, Comp. ( R 3) m v Xr R 2), sroperty ,y/ (Melting point) a-515 City --S02-j07 p1c¼ a-516 ciTh So240 F3CX a-517 ciTh + - SO 2 4 PlC a-518 C1- -SON(CU1)2 ¼ a-519 Cl < -SON(CH2CH3)2 ¼ PlC a-520 C1- -SON(CH3)OCH3 F3C plc a-521 Cl < -SON(CH2CH3)0CH3 ¼ plc a-522 CI -S(=O) OCH3 F3C a-523 C1 < -S(=O)OCU2CU1 ¼ ciTh -SC--O)SCU1 ¼ a-525 Cl < -S(--O)SCH2CH1 p1c¼ a-526 City -CO F3C Hz 118 120"C ¼¼c(c111)1 plc Table I-a (Continued) Physical No. CORI Itl^i Property No. (K1) 0 K1 w;¼M(K2) (Melting y/ Doint) a-527 C1--l \ --CO a-528 C1- -COCH2SOCH3 F,C Ft( a-529 C1 W,i/ -COCH2S02CH3 a 530 C1 -CO(CH2)2NH2 a-530 CITh -CO(CU2)2NH2 PlC a-531 Cl < -COCH2NHCH3 p1c¼ a-532 Cl CITh -COCH2N(CH3)2 p1c¼ a-533 ciTh -CO2CU2 p1c¼ ciTh -CO2 CU2 ¼ yKoso2cp1 plC ¼ 123 a-535 Cl < F3 -cO plc Hz 123 -CO 125 a-536 Cl + XX CH(CH3)2 F3C < 125 128°C -CO 2S a-537 Cl ½LOCH(CH1)2 28 30°c OCH(CH3)2 F3C a-538 Cl CITh - cho < SCH3 F3CSCHB p1c¼ Table I-a (Continued) Comp. (R3)m L Physical Property NO. R 1$ R, my r ( 2 (lelting a-539 C1 -CO < SO 2CH3 -CO 170 a-540 Cl + -CO X < 170 17DOC (CH3)2N a-541 C1- -CO- ,o) FIC F3C' a-543 ciTh -CSOC(CH1)1 ¼ PlC a-544 Cl city -CSOCH2CF3 ¼ plc a-545 CITh -CSOCH2 CH=C112 ¼ PlC a-546 ciTh -CSOCH2CECH ¼ plc a-547 C1- -CSOCH2CH=CCI2 ¼ plc a-548 Cl + - -CSOCH2C=-CI ¼ FJC' a-549 ciTh -csO ¼ plc a-550 Cl + -CSOCH2 P1C¼ Table I-a (Continued) Comp. ( ( R 3 ) m e R I i 3)m ( R 2)l Physical \ . POint) point) CSOCH CN02 F3C a-551 C1- r a-553 CITh -CSOCH W F3C p1c¼ a-553 C1 v a-556 -csO W ½LC(CH1)1 plc a-557 City CSHOlCCHl p1c¼ an558 -CH2S ¼ plc a-559 C1 cH2SO p1c¼ a-560 Cl CITh -CH2SO2 p1c¼ a-561 City (cH2)2 p1c¼ a-562 C1 -CH20 < Table I-a (Continued) Physical Comp. CK1)m MM p ( R 2), Property No. 0 K1 y)CK 2) -7'iL(R2>1 (Melting point) a-563 Cl e -Cll2SCH2 p1c¼ ciTh -CH2CSCH1 ¼ a-565 Cl < -CH2CSOCH3 | ¼ a-566 Cl -CH2tcl p1c¼ a-567 Cl + -(CU2)2 2< ¼Lcp1 a-568 Cl CITh co2yi3 p1c¼ a-569 ciTh co2¼;;j8 Cn a-570 CITh Co2%)0 F3 CX a-571 C1 F3 -CO2SIl = a-572 Cl city -CO2 < E -isomer an573 Cl -CS2 < F3C X 116.1 C a-574 Cl 4 -CS2 Hz FBC X i Z -isomer a-574 CIG -CS2 0 0 flD1 9. 2 N P1C 15716 Table I-a (Continued) - - Comp. ( R 3)m v Hz ( Physical No. 0 K! (K2)1 qT>L<R,,, Property (Melting Y point) a-575 City cs%½ FBCuai a-576 Cl city -CS -CS-07 F3C a-577 Cl CITh -CS cs½\ p1c¼ L a-578 C1 cs Q plc a-579 Cl + X N F3 CI a-580 CITh + H3 t N F3C P1C¼ 'N-CHJ F3C/ a-581 Cl S ciTh < FBCP1C¼ a-582 Cl S -CH2 < Cl F3C a-583 Cl -C112${5 p1c¼ a-584 C1 -CH2- F3C a-585 CU2YN5j X plc a-586 Cl C\\;%Nj plC¼ Table I-a (Continued) Comp. (R3)m G2 Physical Property (Melting Y point) a-587 CITh -CS2(CU2)2NCU1 p1c¼ CH3 F3C a-588 C1 -CS2(CH2)2SCH3 F3C > F1 a-589 Cl + CH2CH3 F3C < I P1C a-590 C1 -CS2(CH2)2CN P1C¼ a-591 C1 -CS2(CH2)2N02 FBCYol a-592 C1 -CS2(CH2)20CHF2 ¼ PlC a-593 ciTh CSlCCi 1 ¼ plc a-594 City -CS2 HzF3C p1c¼ a-595 Cl + ciTh tNS -CS2- p1c¼ a-596 C1 -CS2- ¼ P1C a-597 ciTh s2N3i ¼ PlC a-598 Cl 4 t N-CH3 F3C -cs,-e Table I-a (Continued) Physical Comp. (R3)m Property No. X (R2)1 Hz ( R 2), P( (Melting point) a-599 Cl + -COCH1 ¼ P2UC a-600 CITh -COCH2CH3 > F2HC/ a-601 C1 -COCH(CH3)2 ¼ P1UC a-602 C1- -COC(CH1)1 ¼ P2HC a-603 ciTh -SO2CU1 ¼ a-604 ciTh -SO2CH2CH3 ¼ P2HC a-605 City -SO2N(CH3)2 P2Hc¼ a-606 Cl + -SO2N(CH2CH3)2 F2HC X P2HC -SO2NCH2CH3 a-60'i CI I CH3 FnHcl a-608 ciTh -CO2 CU1 ¼ P2UC a-609 Cl CI- -CO2CIl1CH3 ¼ P2lIC a-610 ciTh -co ¼ P2UC Table I-a (Continued) Physical Comp. ( R 3) m v R , X R2), L Property No. I CO ~RI(,2>1 (Melting oint) a-611 C1 -CSOCH3 F2HC X P2UC a-612 cITh -CSOCH2CU1 p2Hc¼ F2HC a-613 CI I \ CSO- HC/ a-617 City -CS2CH2CH=CH2 ¼ P2HC a-618 Cl + -CSN(CH3)2 ¼ PU2C a-619 Cl CITh -CS2CH3 ¼ a-620 Cl < -CS2CH2CH1 3 PH2C a-621 Cl Th -CS1CII?CII=CH? FH2C a-622 Cl + ciTh -SO2N(CH3)2 ¼ Pll2C Table I-a (Continued) Physical Property COmP- (K1)m 0 K1 ¼)i(K2)1 (Melting point) a-623 CI- -S02N(CH2CH3)2 C 7 -S02NCH2CH3 a-625 -COCH1 -COCH3 OCH3 a-626 ClO -COCH(CH3)2 F3C X L I a-629 City -SO2CH2CH3 cPl p1c¼ a-630 C1< -SO2N(CH3)2 F3C X a-631 C1 -SO2N(CH2CH3)2 F3C X -SO2NCH2CH3 F a-632 Cl + CH3 CU1 Plc0 a-633 Cl e -SO2N(CH3) 2 p1c¼yp a-634 Cl -S02N(CH3)2 p1c¼ycp1 Table I-a (Continued) Physical Property Comp. (K1) No. Di K! y(K2)! Hz(R2) Property point) a-635 Cl CITh -S0 2 N(CH3)2 F3C X1 CH3 a-636 C1 -SO2N(CH3)2 F3C X a-637 F + -COSCH3 ¼ Oily F3 CI a-638 F + -COSCH2CH3 F3C > Oily 107- a-639 F- -SO2N 3 F3C > 107 110°C a-640 F- -SO,N3 F3C 84C I a-641 Both CH3 F3C > 111"C a-642 The -COCH3 %½CU=CCI2 a-643 Cl + -COCH2CH3 yLscp1 a-644 Both -COCH(CH,),SOCF3 a-645 iTh -COC(CH3)3 S02CF3 a-646 F PMp ) -S02CH3C-CI Table I-a (Continued) Physical Property No. (K1)m v ½y(K2)1 (Melting point) 1 -S02CH2CH3 I a-649 (H3C)3C < -SO2N(CH2CU3) 2 S02 cI -S02NCH2C3OCH2CrCI a-650 F < CH3 W OCH2CECI CU2 a-651 ciTh -SO2N OCU2CU-CCl2 a-652 HrTh -CO2CH3 ScU2cU=ccl2 a-653 iTh -CO2cU2cU2 ¼ySCU2C-Ci a-654 PG F co ¼ P SIOCU2C{I--CCI 2 a-655 Cl < M cho -CO- CH3 < F 2 a-656 t CI CSOCH3SOCH2C-CI a-657 (H3C)3C + -cSOCiI2CU3 ¼yY802cU2c=-cI a-655 F 4 -CS0 ¼¼OCh2Cl Table I-a (Continued) Comp. (R3)m-7 C2F\ -(R2: I Physical Comp. (0R, No. 0 K! (K2)! Property (Melting Y point) a-659 C1 -CSN(CH3)2 a-661 ITh -CS2CH2CH1 w CH2 ICH2- -CS2CH2CH3 -S02N(CH2)2CH3 57- I F CH, P3r0 58"C a-663 F- -SOzc "8;2or -SO2NCH2CH3 130- a-664 Cl < I X 132"C a-664 C1-0 I a- 665 O Hz -CS2CH3 ¼ flD1 9. 2 PlC 1.5922 SCHF2 E~iSOmer a-666 A -CS2CH3 F3C Hz 79.2°C SCHF2 Z-isomer a-667 A -CS2CH3 0 flD! G plc 1. 6004 OCHP2 a-668 OCH -CS2CH3 flD 19. 9 P1C 1.5062 a-669 Cl MU1 -SO2CH3 X FJ( a-670 CI < -SO2CH2CH3 p1c¼ I CH3 F3C Table I-a (Continued) Comp. ( R J)m Hz R, X R2), C Physical No. (Melting point) a-671 C1- -S02N(CH3)2o CHJ F3C' a-672 C1- -S02N(CH2CH3)2 a-674 HzCH, -SCH3 ¼ a-675 HzCH3 -SCH2CH p1c¼ a-676 < CH3 -SCCIl ¼ PlC a-677 Ci CH3 -S < a-678 CI CH3 -SN(CH1) 2 ¼ PlC a-679 Ci CH3 -SN(CH2CH3)2 X PlC a-680 (H3C)3C -CSOCH, F3C X Oily a-681 3C)3C + -CSOCH2CII3 P1C¼ Oily a-682 (H3C)3C + -CSO p1c¼ Oily Table I-a (Continued) Coms. (R 3)m Physical Property No. (K1)rn v R, ¼)i-(K2)! (Melting point) a-683 (H3C)3C 4 -COSCH3 FBCp1C¼ Oily 116 a-684 (H3C) -COSCH2CH3 0 117C F3C a-685 (H3C)3C + -CS < F3C > a-686 (H3C)3C + -CS2CH3 F3C ¼ < Plc 1.5746 a-687 (H3C)3C -SCH3 F3C a-688 (H3C)3C + -SCH2CH3 p1c¼ a-689 (H3C)3C 9 -SCCIl p1c¼ ¼ a-690 (H3C)3C -SN (CU1)2 plc a-691 (H3C)3C Hz -SN(CH2CI13)2 p1c¼ FS( a-692 -CS2CU1 CH3 F3C X 103.6or a-693 C¼U;P2 -CS2CH3 p1c¼ SCAB a-694 a plc Table I-a (Continued) (K1)rn Hz( R 3)m \CC\ I Physical Comp. K! -(K) Property No. W/ X7( I(R2)1 Property Point SOCF, 13 F3 CI a-697 t -CS2CH3 F3C X a-698 Cl X -CS2CU2 ¼ plc a-699 Cl v Hz -CS2CH3 F3C X SO2 ¼ an700 X SO? -CS2CH2 F3C OCH2CH=CC12 a-701 -CS2CH, F3C FBC OCH2C=-CI a-702 -CS2CU2 1 0 SCHz CH=CCI ¼ PlC SCH2CECI a-704 Hz -CS2CH3 F3C X F3C SOCH2CH=CC12 a-705 a -CS2CH3 F 3 SO2CH2CH=CCI2 a-706 A -CS2CH3 1 0 Table I-a (Continued) (K) Physical Comp. lut 3) (R3)m C Property No. Y (Melting point) SOCH2C-CI a-707 A -CS2CH3 F3C X SO2CH2CECI a-708 t -CS2CH3 F3C X ¼ a-709 n -CS2CH3 C 1' C1' F3C' CU ¼ a-712 '½ 2 -CS2CU1 plc a-713 Br Hz -CS2CH3 ¼ 88. O P1C Table I-b Comp. ( R 3) L Physical S(R2)1 property No. point, Y point) b-l KY -CSOCH3 X b-2 \ W -CSOCH2CH3 Cl X b-3 X> -CSO CI b-4 KY -CSCH3 p1C¼ F3C/ b-5 KY -CSCH2CH3 p1c¼ b-6 KY -CSCH2CH=CH2 F3C X b-7 P W -CSCH2CECI ¼ b-S KY -CSOCH3 p1c¼ b-9 KY -CSOCH2CH3 ¼ PlC b-lO KY -CSOCli2CH=CU2 ¼ plc Table I-b (Continued) COmPS ( R 3) n PhYSiCa1 Property No. v R , y½(K2)1 (Melting point) b-ll KY -CSOCH2CECI X PlC b KY -CS2CH1 nD30.2 plc 1.5888 b-13Y- -CS2CH2CH3 106. 2"C -CS2CH2CH=CH2 b-14 KY -CS2CH2CH=C112 plc b-15 KY -CS2CH2CECI ¼ plc b-16 /\ > -CS O F3C ¼ 17 ¼ KY b-18B -CS2 b-19 -CS- KY csM plc b-20 KY -CS W Cl F3C b-21 KY Hz -cso p1c¼ Oily FJL b-22 KY -cs2 plc Table I-b (Continued) (K) Physical Comp. ( R3) n Property No. 5A' yTh2! (Melting point) b-23 KY -CSCH2 < b-24 \W -CSOCH2 p1c¼ b-25 \ W -CS2CH2 ¼ b-26 S' Hz -CS2- 3 plc b-27 KY -CS2%J ¼ plc b-28 KY -cs2%%0 p1c¼ b-29 KY cs2¼;;j8 F3C X 2 b-30 KY -CS2 W N F3C X b-31 KY -CS2 C N p1c¼ b-32 KY W -CS2 qX F3C X .~~ ~.... b-33 KY -cs1M) ¼ Plc b-34 KY -CS2 N X F3C Table I-b (Continued) Comp. (K1)n R, SZ>( R 2)1 Physical No. ti K! (K2)! Property point) plc b-37 KY -COSCH2CH3 F3C X KY -COSCU2CH=CH2 ¼ ¼ b-39 KY -COSCU2 C-Cl b-40 KY -COS p1c¼ ciTh -CSOCH1 ¼ plc b-42 rTh -CSOCH2CH1 p1c¼ b-43 -CS2 CU1 ¼ H3 CS F3 CI b-44 P2UC W -CS2CH2CH3 F3C X b-45 "s Dy -CS2CH2CH=CH2 ¼ U1CO S P1C b-46 02N'- D -cso p1c¼ Table I-b (Continued) CNOolfl.P (K1) Th Physical ¼ K1 ½4)(Kl)! (Melting (ILlelting b-49 b S k -COSCH2CH=CH2 ¼ F 3 CI b-51 H3C e S k -COS < F3C X Table I-c Comp. Physical property No. ( R 3)q K1 "-a y(K2)! property c-l -COCH3 C1 120- 123"C c-2 -COCHB F3 c-3 -COCH2CH3 F3 c-5 Fl -COCH(CH1) 2 ¼ PlC c-6 W -COC(CH1) 1 0 93 9S CI c-7 t -COC(CU1) 1 F3C PlC c-8 4¼ -CON(CH3)2 Oily N CI c-9 p p -SO2CH3 ¼ PlC c-10 t -SO2CU2CU1 p1C¼ Table I-c (Continued) Physical Comp. (Kl)Q#¼) ( Physical Property No. (Rz v, (Melting F3C' c-13 Cl 4 -COCH3 Cl X 102"C c-i4 cI -COCH1 ¼ plc c-15 Cl -COCH2CH3 X plc c-16 o (CH2)2CH3 C1' FJC c-i8 clYt -COC(CU1) 1 ¼ 140"C c-i9 ci -COC(CU2)1 ¼ C1' F,C C-20 olQ -SO2CH3 ¼ PlC c-21 Cl 4 -SO2CH2CH3 F3C > c-22 Cl 4 Cll2)2CH3 plc ~ ¼ Table I-c (Continued) Comp. Physical (R3)q RI Property IY (Melting point) c-25 Cl X -COCH2CH3 ¼ PlC c-26 Cl X -CO(CH2)2CH3 F3C X c-27 Cl Hz -COCH(CH1) 2 p1c¼ c-28 Cl < -COC(CH1) 1 ¼ PlC c-29 CI Hz -SO2CH3 F3C X PlC c-30 Cl -SO2CH2CH3 ¼ PlC c-31 Cl < -SO2(CH2)2CH3 ¼ PlC c-32 < -SO2CH2CH3 P1C¼ C-33 < -SO2N(CH3)2 F3C X 72 c-34 p1cY -COCH1 0 73 plc Table I-c (Continued) Comp. L Physical Comp. ¼ K! y(K2)! RI No. (K1)q (Melting point) c-35 F3C X -COCH2CH3 F3C X PlC c-36 F,C X -CO(CH2)2CH3 X p1c¼ c-37 FJC' -COCH(CH3)2 X PlC c-38 1 cM -COC(CH1) 1 ¼ F3 C. F c-39 SOCHJ c-41 < -SO2(CH2)2CH3 > FBC F3 C-42 F3C 4 -SO2N(CH3)2 123"C c-42 cY -SO2N(CU1)2 PlC i23 plc FIC -S02N(CH3)2 205 c-43 0 -SO2N(CU1)2 ¼ 207C N plc C-44 F3C V -COcH1 ¼ '95%OOC I ; X -COCH2CH3 X C-46 X -CO(CH2)2CH3 ¼ plc Table I-c (Continued) Physical Comp. yCK2)1 Property No. (R3)4 ( K1 (Melting point) c-48 F3C F3C c-49 Plc -502 CU3 ¼ Plc C-50 F3C -SO2CH2CH3 F3C X c-50 c-52 7 COCH3 C c-53 S -COCH3 F3C X c-54 ,s -COCH2CH3 F3C X c-SS ¼ -cO(c112) 2C111 p3c¼ c-56 S zit -COCH(CH3)2 F3C F3 c-S7 ¼ -cOcCcU3)1 P2C¼ C 58 C -SO2CH3 P3C X Table I-c (Continued) Comp. Ct I Physical N, (Kl)40N . y½(K2)1 Physical (Melting point) S02CH2CH3 F3 .. . F Z-isomer c-61 lO f )7ii()%orner F- 120"C C1 c-62 JY -- CO- Oily C1' C1 176"C c-64 Cl < - CO > > 11K- c-65 Cl < -SO2N(CH2CH3)2 FBCp1c¼ Table I-d COmP. (R3) m t PhYSiCa1 property NO. kIrn > ( R 2)l (Melting point) d-l 7 -CH2- -COCH3 F3C' d-3 CH2- -CS2CH3 E-isomer d-3 OCH2- -cS2cU1 0 flD 19. 2 F3C 1.5352 d-4 CH2- -CS2CH3 F3C Z-isomer plc 1.5651 d-5 HzCH2- -CS2CH2CH3 ¼ F3C\/ d-6 CH2- -S02N(CH3)2 F3C d-7 CH2- -S02N(CH2CH3)2 F3C\/ d-8 Cl + CH2- -COCH3 F3C X d-9 | CI + CH2- -CO2CH3 F3C X d-iO CiThCU2- -CS2CH3 13C X PlC Table I-d (Continued) Physical Property No. (k1)rn 0CH2- R 2)l (Melting I VI c1ThcU2- -C52C111CIi1 p1c¼ F3CI d-12 C1 c,- -SO2N(CH3)2 ¼ L F31 d-14 UrThCU2- -COCHB plc d-15 BrThCH2- -CO2CH3 p1c¼ d-i6 BrThCU2- -cS2cU1 p1c¼ d-17 Br CH2-- -CS2CH2CH3 F3C X d-l8 BrThCH2- -SO2N(CH3)2 FBCBr- d-i9 BrThCU1- -SO2N(CH2CH3)2 F3C X d-20 PThcU2- -COCH3 p1c¼ d 21 \ CH2- -CO2CH1 F3C > d-22 PThcU2- -CS2CH3 F3C Table I-d (Continued) ,,,, (RB)m Physical Property No. e CH2- R, XT R 2), (Melting point) d-23 F- CH2- -CS2CH2CH3 p1c¼ F3C d-24 F- CH2- -SO2N(CH3)2 F plc d-25 F- CH2- -SO2N(CH2CH3)2 F3C X F3( d-26 CI- CH1- -COCH3 F3C X d-27 HzCl Mc1H2 -CO2CH3 F3C X C1 F3C d-29 C1- CH2- -CS2CH2CH3 d-30 C1- CH2- -SO2N(CH3)2 ¼ plc d-3i cIMc1iI2- -SO2N(CH2CH3)2 F3C X c(cU1)1 d-32 C W -COCH3 F3C X d-33 C(CH,), -CO2CH1 ¼ McU2- plc C(CH3)3 d-34 yLcH2- -CS2 CU1 1 0 Table I-d (Continued) Physical No. | K Tri Poperty Y(lelting point) C(CHB)B d-35 )yOcU2 2 -CS2CH2CH3 F C C(CU1)1 d-36 cU2 t -SO2N(CH3)2 > c(cH1)1 d-37 McH2 CH2 -SO2N(CH2CH3)2 X Table 2 Inter- C property ediatE Q y½(K2)! (Melting point) 154 II-1 FBC r 146 11-2 Cl + clO X 146 148°C Plc 168 11-3 BrO 0 i730C Plc 182 ll 4 < Cl F3C X | 183°C ll-5 F ¼ Plc 120 11-6 P 0C1 Plc? i30C ll-7 >F F3C X 164 ll-8 F3C Plc0 167C 11-9 F3C F,C- 11-10 F3C p1c¼ Table 2 (Continued) Inter- L Physical mediat Q y(Kl)! C ( R2), (Melting No. point) I 11-11 02N p1c¼ OzN--(O) 11-12 c1M2 p1M FBCX 175 1770C 11-13 O2N < 11-14 4 H3CS < Cl F3C X Ci ll-15 H3CO2S Hz¼ F3C X 0 Ci ¼ II-i6YM plc 187 ll-17 t Cl F3C X 189C 118 ll-18 Cl X FBC> 12lox 139 11-19 F plc0 F3C X 144°C 11-20 I + F3C p1c¼ 170 180°C 188 1if21 CCI- e FBCX 189"C 176 11-22 clO p1c¼ FBCX 180°C Table 2 (Continued) Inter- L Physical Inter- , Q Hz ( R 2)l property mediat Q y(K2)! property No. point) 87 87 11-23 H3C Hz FBC> 90"C 11-24 (H3C)2CH p1c¼ 156 11-25 (111C)1C0 Plc0 iS8C 90 11-26 U1cOO 0 92C plc 11-27 no NC- p1c¼ 11-28 F3CO + F3C FJC 11-29 H3COS-- 0 11-31 c1MM plc ll-32 H3C O½½ p1c¼ 11-33 Cl > F2HC 11-34 Cl ciTh ¼ FH2c Table 2 (Continued) Physical Inter- f Hz property mediat , Q y#(K2) (Melting No. Y point) 11-35 ciTh F3C) 11-36 C I PlC¼;Ul p1c¼' SCH1 11-37 C p1cyi½i F3 11-38 C1- p1c CF3 11-39 Cle cpl p1cY 11-40 ciTh p Plc¼½ 11-41 C1- F3CXF 11-42 ciTh p1c%½cp1 CH3 11-43 C1-Q FJC 11-44 Ov p1M SCUP2 11-45 SCHF2 OCUP2 11-46 plc0 Table 2 (Continued) -Physical Inter- L (R2)1 property II-47 C1 CH3 F3C CH=CC12 ll-48 CH CC 2 FBCplc0 CH=CF 11-49 CH CF2 p1c¼ 11-50 5)) p1M . . lI-Si ½ Plc F,C ¼ ll-52 plc ¼ 11-53 plc ~54 C1 9 > FBCp1c¼ 11-55 c1SO\½ p1c¼ 11-56 ciM SO¼¼ p1M OCU2CU=CCI 2 ¼ 11-57 ¼ plc F 3 CI 11-58 plc0 Table 2 (Continued) Inter- Q Hz ( R 2)l Physical mediat Q (Melting No. y)(K2)! property point) SCU2CU=CCi 2 II-59 SCH2CrCI 1I-60 3OCU2CU=CCI 2 11-61 Plc0 SO2CH2CH=CCI2 ½ SOCH2CrCI ll-63 m plc0 SO2CH2CECI ll-64 a FBCplc0 ll-65 v CH2° W F3C X ll-66 v CH2S a F3C X II-67 CO 11-68 (%cU)y0 p2M CH, 105- 11-69 Plc i08C 11-70 CI p2c¼ Table 2 (Continued) Physical Inter- L Physical mediate Q X ~( R2), property No. (Melting point) II-71 11-73 P2UC p1c¼ ll-74 H3CO'~ W F3C X II-75 O2NTh W plc ll-76 XW Q, P1M ll-77 3 My p1c¼ 11-78 H3C W S k Plc 11-79 CI ¼ plc ll-80 F3(30 C1' ll-81 X X Cl N F3C 11-82 < X 115 119"C F3C N F3C Table 2 (Continued) Physical Inter- 1 < property mediat Q I\yl -(K2)1 No. Q Ç)J (Melting point) p 1c 206 ll-83 F3C Hz F3C Hz | 206 213"C II-84 cI Y p1c¼ ll-86 < CH2- p1c¼ 11 87 CH2- F3C 11-88 Br- CH2- ll-89 F 4 CH2- F3C 11-90 cIMciUl ¼ -C1 FJ C(CU1)1 ll-91 C(CII3)3 F3C <

Now, Test Examples will be described.

TEST EXAMPLE 1 Miticidal test against adults of two-spotted spider mite (Tetranychus urticae) A miticidal solution was prepared to bring the concentration of a compound of the present invention to 800 ppm. Kidney bean (Phaseolus vulqaris) seedling with only one primary leaf left, was transplanted in a cup (diameter: 8 cm, height: 7 cm) and 30 adults of two- spotted spider mite (Tetranychus urticae) were inoculated thereto. The adult mites were immersed together with the kidney bean leaf in the above miticidal solution for about 10 seconds, then dried in air and left in a constant temperature chamber at 260C with lightening. On the second day after the treatment, dead adult mites were counted, and the mortality was calculated by the following equation.

Number of dead adult mites Mortality (%) = x 100 Number of treated adult mites As a result, the mortality was at least 90% with each of Compound Nos. 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, a-97, a-99, a-153, a-l56, a- 160 to 164, a-166 to 167, a-173, a-175 to 181, a-183 to 189, a-191, a-194 to 197, a-200 to 202, a-206 to 207, a- 209, a-211 to 212, a-214 to 215, a-218 to 221, a-223 to

224, a-227, a-230, a-240, a-244, a-245, a-250 to 251, a- 254 to 258, a-260 to 263, a-267, a-274, a-286, a-288, a- 290, a-298, a-300, a-303 to 308, a-310, a-316 to 319, a- 322, a-323, a-325, a-328 to 329, a-331, a-335, a-342, a- 359, a-360, a-362 to 363, a-365, a-367 to 368, a-371 to 373, a-375 to 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. 11-2.

TEST EXAMPLE 2 Ovicidal test against two-spotted spider mite (Tetranychus urticae) An ovicidal solution was prepared to bring the concentration of a compound of the present invention to 800 ppm. Kidney bean (Phaseolus vulqaris) seedling with only one primary leaf left, was transplanted in a cup (diameter: 8 cm, height: 7 cm), and adults of two-spotted spider mite (Tetranychus urticae) were inoculated thereto and permitted to lay eggs for 24 hours, whereupon the adult mites were removed. The eggs were dipped together with the kidney bean leaf in the above ovicidal solution for about 10 seconds, then dried in air and left in a constant temperature chamber at 260C with lightening. On the 7th day after the treatment, hatching of the eggs was

investigated, and the ovicidal ratio was obtained by the following equation.

Number of dead eggs Ovicidal ratio (%) = x 100 Number of treated eggs As a result, the ovicidal ratio was at least 90% with each of Compound Nos. 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 to 207, a-209, a-211 to 212, a-214 to 215, a-218 to 221, a-223 to 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 to 308, a-310, a-316 to 319, a-322, a-323, a-325, a-328 to 329, a-331 to 333, a-335, a-337, a-342, a-348, a-359, a- 360, a-362 to 363, a-365, a-367 to 368, a-371 to 372, a- 375 to 376, a-381, a-382, a-384, a-386 to 388, a-390, a- 394 to 395, a-399, 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.

TEST EXAMPLE 3 Insecticidal test against small brown planthopper (Laodelphax striatellus)

Rice seedling was dipped for about 10 seconds in an insecticidal solution prepared to bring the concentration of a compound of the present invention to 800 ppm and then dried in air. Then, the seedling with its root wrapped with a wet absorbent cotton, was put into a test tube. Then, 10 larvae of small brown planthopper (Laodelphax striatellus) were released therein, and the test tube was covered with a gauze and left in a constant chamber at 260C with lightening. On the 5th day after the release, dead larvae were counted, and the mortality was calculated by the following equation.

Number of dead insects Mortality (%) = x 100 Number of released insects As a result, the mortality was at least 90% with each of Compound Nos. a-10 to 11, a-161, a-362, a-474, a- 637, a-638 and c-34.

TEST EXAMPLE 4 Insecticidal test against green peach aphid (Myzus persicae) An insecticidal solution was prepared to bring the concentration of a compound of the present invention to 800 pm. The petiole of each of eggplants with only one foliage leaf left (planted in a pot having a diameter of 8 cm and a height of 7 cm) was coated with a sticker, and about 2-3 apterous viviparous female of green peach aphid (Myzus persicae) were infested and incubated on the

foliage leaf of the eggplant. After two days from the infestation, the adult insects were removed, and the number of larvae was counted. Then, the foliage leaf of the eggplant infested with the larvae was dipped in the above insecticidal solution for about 10 seconds, then dried in air and left in a constant temperature chamber at 260C with lightening. On the 5th day after the treatment, dead insects were counted, and the mortality was calculated by the following equation: Number of dead insects Mortality (%) = x 100 Number of treated insects The insects released from the leaf were counted as dead insects.

As a result, the mortality was at least 90% with each of Compound Nos. a-10 to 11, a-160 to 162, a-637 and a-638.

TEST EXAMPLE 5 Test on preventive effect against tomato late blight Tomato (cultivar: Ponderosa) was cultivated in a polyethylene pot having a diameter of 7.5 cm. When the tomato reached a four-leaf stage, it was sprayed with 10 ml of a solution having a predetermined concentration of a compound of the present invention through a spray gun.

After the solution was dried, the tomato plant was sprayed and inoculated with a zoosporangia suspension of fungi of late blight (Phytophthora infestans) and kept in

a constant-temperature chamber at 200C.

Third to fourth day after the inoculation, the area of lesions was examined, and the control index was determined according to the following criteria for evaluation.

Control index Deqree of disease outbreak (visual observation) 5 No lesions are recognizable at all.

4 The area, number or length of lesions is less than 10% of that in the non-treated plot.

3 The area, number or length of lesions is less than 40% of that in the non-treated plot.

2 The area, number or length of lesions is less than 70% of that in the non-treated plot.

1 The area, number or length of lesions is 70% or more of that in the non-treated plot.

As a result, Compound No. a-3 exhibited a control index of 5 at a concentration of 250 ppm.

TEST EXAMPLE 6 Test on preventive effect against wheat powdery mildew Wheat (cultivar: Norin No. 61) was cultivated in a polyethylene pot having a diameter of 7.5 cm. When the wheat reached a 1.5 leaf stage, it was sprayed with 10 ml of a solution having a predetermined concentration of a compound of the present invention through a spray gun.

After the solution was dried, the wheat was dusted and

inoculated with conidia of fungi of powdery mildew (Erysiphe qraminis) and kept in a constant-temperature chamber at 200C.

Eighth day after the inoculation, the area of lesions or the spore-formation area was examined, and the control index was determined according to the following criteria for evaluation.

Control index Degree of disease outbreak (visual observation) 5 No lesion or spore-formation is recognizable at all.

4 The area or number of lesions or the spore-formation area is less than 10% of that in the non-treated plot.

3 The area or number of lesions or the spore-formation area is less than 40% of that in the non-treated plot.

2 The area or number of lesions or the spore-formation area is less than 70% of that in the non-treated plot.

1 The area or number of lesions or the spore-formation area is 70% or more of that in the non-treated plot.

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

TEST EXAMPLE 7 Test on preventive effect against oat crown rust Oat (cultivar: Zenshin) was cultivated in a

polyethylene pot having a diameter of 7.5 cm. When the oat reached a 1.5 leaf stage, it was sprayed with 10 ml of a solution having a predetermined concentration of a compound of the present invention through a spray gun.

After the solution was dried, the oat was sprayed and inoculated with a spore suspension of fungi of crown rust (Puccinia coronata). Eighth day after the inoculation, the area of lesions or spore-formation area was examined and the control index was determined in the same manner as in Test Example 6.

As a result, compound Nos. a-78, a-123 and a-166 exhibited a control index of 5 at a concentration of 500 ppm, and Compound No. a-3 exhibited a control index of 5 at a concentration of 250 ppm.

TEST EXAMPLE 8 Control test against green algae Green algae preliminarily cultured for 7 days (O Selenastrum capricornutum or 9 Chlorella vulqaris) were inoculated to a culture medium for algae containing a solution prepared to bring the concentration of a compound of the present invention to 100 ppm, and left to stand for 8 days in a constant temperature chamber at 200C with lighting, whereupon growth degree of the green algae was investigated, and the control index was determined according to the following criteria for evaluation.

Control index Growth degree (visual observation) A No growth of green algae is observed at all B Growth of green algae is slightly observed.

C Growth of green algae is observed in the same degree as in the non-treated plot.

As a result, Compound Nos. a-3, a-6 and a-70 exhibited a control index of A against green algae Ol at a concentration of 100 ppm. Further, against green algae g, Compound Nos. a-3, a-6, a-26 and a-39 exhibited a control index of A at a concentration of 100 ppm.

Now, formulation Examples will be described.

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

FORMULATION EXAMPLE 2 (a) Compound No. b-26 5 parts by weight (b) Talc 95 parts by weight The above components are uniformly mixed to obtain a dust.

FORMULATION EXAMPLE 3 (a) Compound No. a-39 20 parts by weight (b) N,N'-dimethylacetamide 20 parts by weight

(c) Polyoxyethylenealkylphenyl ether 10 parts by weight (d) Xylene 50 parts by weight The above components are uniformly mixed and dissolved to obtain an emulsifiable concentrate.

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

FORMULATION EXAMPLE 5 (a) Compound No. b-35 50 parts by weight (b) Oxylated polyalkylphenyl phosphate-triethanolamine 2 parts by weight (c) Silicone 0.2 part 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-dispersible granules.

FORMULATION EXAMPLE 6 (a) Compound No. b-48 5 parts by weight (b) Polyoxyethyleneoctylphenyl ether 1 part by weight (c) Phosphoric acid ester of polyoxyethylene 0.1 part by weight (d) Granular calcium carbonate 93.5 parts by weight The above components (a) to (c) are preliminarily uniformly mixed and diluted with a proper amount of acetone, and then the mixture is sprayed onto the component (d), and acetone is removed to obtain granules.

FORMULATION EXAMPLE 7 (a) Compound 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 uniformly mixed and dissolved to obtain an ultra low volume formulation.

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