Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Reexamination Certificate
1999-08-16
2001-02-13
Higel, Floyd D. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
C514S237500, C514S237800, C514S241000, C514S255010, C514S267000, C514S327000, C514S330000, C514S347000, C514S354000, C514S369000, C514S372000, C514S374000, C514S398000, C514S407000, C514S424000, C514S445000, C514S473000, C514S550000, C544S163000, C544S224000, C544S316000, C544S384000, C544S219000, C546S330000, C546S226000, C548S538000, C548S542000, C548S221000, C548S230000, C548S214000, C548S243000, C548S375100, C558S398000, C558S402000, C558S048000, C549S065000, C549S495000
Reexamination Certificate
active
06187944
ABSTRACT:
DESCRIPTION
The present invention relates to novel acrylonitrile compounds useful as active ingredients for pesticides.
(1) EP 104690A, EP 62238A and U.S. Pat. No. 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 &agr;-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. Pat. No. 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. Pat. No. 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) WO97/40009 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(R
4
)— or ═N—, R
1
is alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, —C(═O)R
5
, —C(═S)R
5
, —S(O)
w
R
5
or —CH
2
R
9
, each of R
2
and R
3
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, R
4
is hydrogen, halogen, alkyl or haloalkyl, R
5
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(R
7
)R
8
, 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 R
7
and R
8
is hydrogen, alkyl or alkoxy, R
9
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)R
10
, —C(═S)R
10
, —S(O)
w
R
10
or trimethylsilyl, R
10
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 R
2
may be the same or different, when each of m, n and q is 2 or more, a plurality of R
3
may be the same or different, provided that the following compounds are excluded (1) a compound wherein Q is Qb, Y is ═C(R
4
)—, and R
1
is alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, —S(O)
w
R
5
or —CH
2
R
9
, (2) a compound wherein Q is Qb, Y is ═C(R
4
)—, R
1
is —C(═O)R
5
, and R
5
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(R
7
)R
8
, 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(R
4
)—, R
1
is —C(═S)R
5
, and R
5
is —N(R
7
)R
8
, (4) a compound wherein Q is Qb or Qc, Y is ═N—, R
1
is alkyl or —C(═O)R
5
, and R
5
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 R
2
and R
3
, 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 R
5
, 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 su
Ikeda Tsuyoshi
Koyanagi Toru
Morita Masayuki
Nakamura Yuji
Ogawa Munekazu
Higel Floyd D.
Ishihara Sangyo Kaisha Ltd.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
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