Acrylonitrile compounds, process for their production and pesticides containing them

A process for producing an acrylonitrile compound of the following formula (I) or its salt:

• wherein Q is
• Y is ═C(R4)—, R1 is alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, —C(═O)R5, —C(═S)R5, —S(O)wR5 or —CH2R9, each of R2 and R3 is halogen, alkyl which is unsubstituted or substituted, alkenyl which is unsubstituted or substituted, alkynyl which is unsubstituted or substituted, alkoxy which is unsubstituted or substituted, alkenyloxy which is unsubstituted or substituted, alkynyloxy which is unsubstituted or substituted, alkylthio which is unsubstituted or substituted, alkylsulfinyl which is unsubstituted or substituted, alkylsulfonyl which is unsubstituted or substituted, alkenylthio which is unsubstituted or substituted, alkenylsulfinyl which is unsubstituted or substituted, alkenylsulfonyl which is unsubstituted or substituted, alkynylthio which is unsubstituted or substituted, alkynylsulfinyl which is unsubstituted or substituted, alkynylsulfonyl which is unsubstituted or substituted, nitro, cyano, phenyl which is unsubstituted or substituted, phenoxy which is unsubstituted or substituted, phenylthio which is unsubstituted or substituted, phenylsulfinyl which is unsubstituted or substituted, phenylsulfonyl which is unsubstituted or substituted, benzyl which is unsubstituted or substituted, benzyloxy which is unsubstituted or substituted, benzylthio which is unsubstituted or substituted, or benzoyl which is unsubstituted or substituted, R4 is hydrogen, halogen, alkyl or haloalkyl, R5 is alkyl which is unsubstituted or substituted, alkenyl which is unsubstituted or substituted, alkynyl which is unsubstituted or substituted, alkoxy which is unsubstituted or substituted, alkenyloxy which is unsubstituted or substituted, alkynyloxy which is unsubstituted or substituted, alkylthio which is unsubstituted or substituted, alkenylthio which is unsubstituted or substituted, alkynylthio which is unsubstituted or substituted, cycloalkyl, cycloalkyloxy, cycloalkylthio, —N(R7)R8, phenyl which is unsubstituted or substituted, phenoxy which is unsubstituted or substituted, phenylthio which is unsubstituted or substituted, benzyl which is unsubstituted or substituted, benzyloxy which is unsubstituted or substituted, benzylthio which is unsubstituted or substituted, —J, —O—J or —S—J, each of R7 and R8 is hydrogen, alkyl or alkoxy, R9 is cyano, phenyl which is unsubstituted or substituted, phenoxy which is unsubstituted or substituted, phenylthio which is unsubstituted or substituted, phenylsulfinyl which is unsubstituted or substituted, phenylsulfonyl which is unsubstituted or substituted, benzyl which is unsubstituted or substituted, benzyloxy which is unsubstituted or substituted, benzylthio which is unsubstituted or substituted, benzoyl which is unsubstituted or substituted, —J, —C(═O)R10, —C(═S)R10, —S(O)wR10 or trimethylsilyl, R10 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 is unsubstituted or substituted), 1 is from 1 to 4, m is from 0 to 5, w is from 0 to 2, when 1 is 2 or more, a plurality of R2 are the same or different, when m is 2 or more, a plurality of R3 are the same or different, provided that the following compounds are excluded 3-(4-chlorophenyl)-2-phenyl-3-ethoxyacrylonitrile, 2-(3,5-dimethoxyphenyl)-3-(2-methoxy-4-methylphenyl)-3-acetoxyacrylonitrile, and 2-(3,5-dimethoxyphenyl)-3-(2,6-dimethoxy-4-methylphenyl)-3-acetoxyacrylonitrile, which comprises reacting a compound of the formula (II):
• wherein Q, Y, R2 and 1 are as defined above, with a compound of the formula (III):
• R1—X (III)
• wherein R1 is as defined above, and X is halogen.

A compound of the formula (II-1) or its salt:

• wherein Q is
• R2a is haloalkyl, R2b is halogen, alkyl or haloalkyl, R3 is halogen, alkyl which is unsubstituted or substituted, alkenyl which is unsubstituted or substituted, alkynyl which is unsubstituted or substituted, alkoxy which is unsubstituted or substituted, alkenyloxy which is unsubstituted or substituted, alkynyloxy which is unsubstituted or substituted, alkylthio which is unsubstituted or substituted, alkylsulfinyl which is unsubstituted or substituted, alkylsulfonyl which is unsubstituted or substituted, alkenylthio which is unsubstituted or substituted, alkenylsulfinyl which is unsubstituted or substituted, alkenylsulfonyl which is unsubstituted or substituted, alkynylthio which is unsubstituted or substituted, alkynylsulfinyl which is unsubstituted or substituted, alkynylsulfonyl which is unsubstituted or substituted, nitro, cyano, phenyl which is unsubstituted or substituted, phenoxy which is unsubstituted or substituted, phenylthio which is unsubstituted or substituted, phenylsulfinyl which is unsubstituted or substituted, phenylsulfonyl which is unsubstituted or substituted, benzyl which is unsubstituted or substituted, benzyloxy which is unsubstituted or substituted, benzylthio which is unsubstituted or substituted, or benzoyl which is unsubstituted or substituted, d is from 0 to 2, m is from 0 to 5, when d is 2, two R2b are the same or different, when m is 2 or more, a plurality of R3 are the same or different.