Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-01-24
2003-09-23
McKane, Joseph K. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S357000, C514S438000, C514S520000, C546S281400, C546S330000, C549S076000, C558S303000
Reexamination Certificate
active
06624179
ABSTRACT:
TECHNICAL FIELD
The present invention relates to geometrical isomers of acrylonitrile compounds useful as active ingredients for pesticides, a mixture thereof and a process for their production.
BACKGROUND ART
WO98/35935 discloses acrylonitrile compounds or their salts, and it is disclosed that such compounds have geometrical isomers. However, no specific method is disclosed, whereby one geometric isomer compound of an acrylonitrile compound represented by the following formula (I) or of its salt, is produced in a larger proportion than the other geometrical isomer compound.
DISCLOSURE OF THE INVENTION
The present inventors have conducted various studies on a method whereby one geometrical isomer compound is produced in a larger proportion than the other geometrical isomer compound, and as a result, the present invention has been accomplished. Namely, the present invention provides a geometrical isomer of an acrylonitrile compound represented by the formula (I) or of its salt, or a mixture thereof:
[wherein T is phenyl which is substituted by R
2
, or pyridyl which is substituted by R
2
, Q is phenyl which may be substituted by R
3
, thienyl which may be substituted by R
3
, pyridyl which may be substituted by R
3
, or benzyl which may be substituted by R
3
, R
1
is —C(═O)R
4
or —C(═S)R
4
, 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 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
5
)R
6
, 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
5
and R
6
is hydrogen, alkyl or alkoxy, J is a 5- or 6-membered heterocyclic group (the heterocyclic group may be substituted) having from 1 to 4 hetero atoms of at least one type selected from the group consisting of O, S and N, provided that the following compounds are excluded: (1) a compound wherein T is phenyl which is substituted by R
2
, Q is thienyl which may be substituted by R
3
, R
1
is —C(═O)R
4
, and R
4
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
5
)R
6
, 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, (2) a compound wherein T is phenyl which is substituted by R
2
, Q is thienyl which may be substituted by R
3
, R
1
is —C(═S)R
4
, and R
4
is —N(R
5
)R
6
, (3) a compound wherein T is pyridyl which is substituted by R
2
, Q is thienyl which may be substituted by R
3
, or pyridyl which may be substituted by R
3
, R
1
is —C(═O)R
4
, and R
4
is alkyl, (4) &agr;-(3,5-dimethoxyphenyl)-&bgr;-(2-methoxy-4-methylphenyl)-&bgr;-acetoxyacrylonitrile, and (5) &agr;-(3,5-dimethoxyphenyl)-&bgr;-(2,6-dimethoxy-4-methylphenyl)-&bgr;-acetoxyacrylonitrile], wherein the geometrical isomer has a longer retention time when analyzed by reversed-phase liquid chromatography in which a packing comprising silica having chemically bonded thereto an alkyl group selected from trimethyl, octyl and octadecyl, is used as the stationary phase, and a polar solvent selected from water, methanol and acetonitrile, is used as the mobile phase, and the geometrical isomer mixture contains such geometrical isomer in a larger proportion; and a process for their production.
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 R
2
or R
3
, and 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
4
, 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 two or more, they may be the same or different.
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 and the benzoyl which may be substituted, for R
2
or R
3
, 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 and the benzylthio which may be substituted, for R
4
, and for the heterocyclic group for J, may, for example, be halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro, cyano, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, amino, monoalkylamino or dialkylamino. The number of substituents may be one or more, and when it is two or more, they may be the same or different.
The heterocyclic group for J may, for example, be furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazoly, pyridyl, pyrimidinyl, 1-pyrrolidinyl, 1-piperidinyl or 4-morpholino.
The alkyl or alkyl moiety contained in R
2
, R
3
, R
4
, R
5
or R
6
, 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 R
2
, R
3
or R
4
, may, for example, be straight chain or branched one having from 2 to 6 carbon atoms, such as vinyl, allyl, butadienyl, isopropenyl, ethynyl, propynyl or 2-penten-4-ynyl. The cycloalkyl or cycloalkyl moiety contained in R
4
, may, for example, be one having from 3 to 6 carbon atoms, such as cyclopropyl, cyclopentyl
Hisamatsu Akihiro
Kanamori Mayumi
Koyanagi Toru
Morita Masayuki
Nakamura Yuji
Ishihara Sangyo Kaisha Ltd.
McKane Joseph K.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Shiao Robert
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