Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-06-14
2001-12-11
Powers, Fiona T. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S340000, C514S341000, C544S137000, C544S139000, C546S271400, C546S272100, C546S272700, C548S235000, C548S247000, C548S341100
Reexamination Certificate
active
06329371
ABSTRACT:
TECHNICAL FIELD
This invention relates to a novel &agr;-substituted benzyl heterocyclic derivative, an intermediate for producing the same, and an agrochemical composition containing the same as an active ingredient.
1. Background Art
Some &agr;-substituted benzyl heterocyclic derivatives are known to have biological activity such as herbicidal activity, fungicidal activity etc. and pharmacological activity such as anti-arrhythmic activity, sedative activity etc.
For example, JP-A 6-49039, JP-A 7-48359, and WO 94/08975 disclose &agr;-substituted benzyl heterocyclic derivatives showing herbicidal and fungicidal activity. However, heterocyclic rings of those are limited to pyrimidine and its fused rings. Further, any specific compounds having substituents similar to those of this invention at the ortho position of benzyl are not disclosed therein.
The object of this invention is to provide compounds having more potent fungicidal and insecticidal activity.
2. Disclosure of Invention
The present inventors have intensively researched to achieve the above object. As a result, it has been found that &agr;-substituted benzyl heterocyclic derivatives described below show potent fungicidal and insecticidal activity. Thus, the present invention has been accomplished.
This invention relates to a compound represented by the formula (I):
wherein R
1
is an optionally substituted heterocyclic group except pyrimidinyl; R
2
is optionally substituted aryl, or an optionally substituted heterocyclic group; R
3
is hydrogen alkyl, alkenyl, or alkynyl; R
4
is hydrogen, alkyl, alkoxy, halogen, nitro, cyano, or halogenated alkyl; M is (1) oxygen, (2) S(O)
i
wherein i is 0, 1, or 2, (3) NR
5
wherein R
5
is hydrogen, alkyl, or acyl, (4) —Q—N═C(R
6
)— wherein Q is oxygen or NR
7
wherein R
7
is hydrogen, alkyl, or acyl; R
6
is hydrogen, alkyl, acyl, alkylthio, alkylsulfinyl, alkylsulfonyl, halogenated alkyl, cyano, alkoxycarbonyl, alkoxyalkyl, optionally substituted amino, or cycloalkyl, or R
2
and R
6
taken together form a monocyclic group or a fused polycyclic group optionally having a hetero atom, (5) —B—C(R
8
)═N— wherein B is oxygen or sulfur and R
5
is hydrogen, alkyl, acyl, alkylthio, alkylsulfinyl, alkylsulfonyl, halogenated alkyl, cyano, alkoxycarbonyl, alkoxyalkyl, optionally substituted amino, or cycloalkyl, (6) —CH═N—N═C(R
9
)— wherein R
9
is hydrogen, alkyl, cyano, cycloalkyl, or halogenated alkyl, or (7) —CH═N—A—(CR
10
R
11
)m— wherein R
10
and R
11
are independently hydrogen, alkyl, cyano, or halogenated alkyl, A is oxygen or NR
12
wherein R
12
is hydrogen, alkyl, or acyl, and m is 0 or 1; and n is 0, 1, or 2.
In this specification the term “lower” means to have 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 4 carbon atoms, unless otherwise defined.
The optionally substituted heterocyclic group represented by R
1
includes an unsubstituted heterocyclic group and a substituted heterocyclic group. Examples of these heterocyclic groups are 5 to 7 membered heterocyclic groups having 1 to 4 hetero atoms selected from nitrogen, sulfur, and oxygen in the ring, specifically, pyridyl such as pyridin-2-yl and pyridin-3-yl, isoxazolyl such as isoxazol-3-yl, isoxazol-4-yl, and isoxazol-5-yl, isoxazolinyl such as 2-isoxazolin-3-yl and 2-isoxazolin-5-yl, isothiazolyl such as isothiazol-5-yl, thiadiazolyl such as 1,3,4-thiadiazolyl (ex. 1,3,4-thiadiazol-2-yl) and 1,2,3-thiadiazolyl, pyridazinyl such as pyridazin-2-yl, pyrazolyl such as pyrazol-1-yl and pyrazol-5-yl, furyl such as furan-2-yl, thienyl such as thiophen-2-yl, imidazolyl such as imidazol-2-yl, oxazolyl such as oxazol-2-yl and oxazol-5-yl, thiazolyl such as thiazol-2-yl, thiazolidinyl such as thiazolidin-2-yl, oxadiazolyl such as 1,3,4-oxadiazolyl (ex. 1,3,4-oxadiazol-2-yl) and 1,2,4-oxadiazolyl, triazolyl such as 1,2,4-triazolyl (ex. 1H-1,2,4-triazol-1-yl, 4H-1,2,4-triazol-4-yl, and 1H-1,2,4-triazol-5-yl), pyrazinyl and the like.
Any of these heterocyclic groups may form a fused ring with a carbocyclic ring or another heterocyclic ring. Examples of the fused ring are benzoxazolyl such as benzoxazol-2-yl, benzothiazolyl such as benzothiazol-2-yl, benzoisoxazolyl such as benzoisoxazol-3-yl, tetramethyleneisoxazolyl such as 3,4-tetramethyleneisoxazol-5-yl and 4,5-tetramethyleneisoxazol-3-yl and the like.
These heterocyclic groups and fused rings thereof may have a bond at any possible position on the ring.
The substituents of the substituted heterocyclic group represented by R
1
include, for example, lower alkyl such as methyl, ethyl, propyl, and butyl, lower alkenyl such as vinyl, allyl, and 2-butenyl, lower alkynyl such as ethynyl, 2-propynyl, and 3-butynyl, cycloalkyl such as cyclopropyl, cyclopentyl, and cyclohexyl, cycloalkenyl such as cyclopentenyl and cyclohexenyl, lower alkanoyl such as acetyl, propionyl, and isobutyryl, lower alkylsilyl such as methylsilyl, ethylsilyl, propylsilyl, and butylsilyl, halogenated lower alkyl such as trifluoromethyl, trichloromethyl, chloromethyl, 2-bromoethyl, and 1,2-dichloropropyl, di(lower)alkylamino such as dimethylamino and diethylamino, phenyl, phenyl(lower)alkyl such as benzyl and phenethyl, phenyl(lower)alkenyl such as styryl and cinnamyl, furyl(lower)alkyl such as 3-furylmethyl and 2-furylethyl, furyl(lower)alkenyl such as 3-furylvinyl and 2-furylallyl, halogen such as fluorine, chlorine, bromine, and iodine, nitro, cyano, lower alkylthio such as methylthio, ethylthio, and propylthio, —OR
13
wherein R
13
is hydrogen, lower alkyl such as methyl, ethyl, and propyl, lower alkenyl such as vinyl, allyl, and 2-butenyl, lower alkynyl such as ethynyl, 2-propynyl, and 3-butynyl, lower alkanoyl such as acetyl, propionyl, and butyryl, phenyl, lower alkoxyphenyl such as 3-methoxyphenyl and 4-ethoxyphenyl, nitrophenyl such as 3-nitrophenyl and 4-nitrophenyl, cyanophenyl such as 2-cyanophenyl and 3-cyanophenyl, phenyl(lower)alkyl such as benzyl, phenethyl, and phenylpropyl, cyanophenyl(lower)alkyl such as 3-cyanophenylmethyl and 4-cyanophenylethyl, benzoyl, tetrahydropyranyl, pyridyl, trifluoromethylpyridyl, pyrimidinyl, benzothiazolyl, quinolyl, benzoyl(lower)alkyl such as benzoylmethyl and benzoylethyl, benzenesulfonyl, or lower alkyl benzenesulfonyl such as toluenesulfonyl, —CH
2
—T—R
14
wherein T is oxygen, sulfur or NR
15
wherein R
15
is hydrogen or lower alkyl and R
14
is phenyl, halophenyl such as 2-chlorophenyl and 4-fluorophenyl, lower alkylphenyl such as 2-methylphenyl and 2,5-dimethylphenyl, lower alkoxyphenyl such as 2-methoxyphenyl and 4-ethoxyphenyl, pyridyl, or pyrimidinyl, and the like. Among those lower alkyl and halogenated alkyl are preferable, and methyl is especially preferable.
Preferred embodiments of R
1
include pyridin-2-yl, pyridin-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 2-isoxazolin-3-yl, 2-isoxazolin-5-yl, imidazol-2-yl, 1,3,4-oxadiazol-2-yl, 1,2,4-oxadiazol-3-yl, and 1,2,3-thiadiazol-5-yl which are substituted optionally.
Especially preferred embodiments of R
1
include isoxazol-3-yl, 5-methylisoxazol-3-yl, 3-methylisoxazol-5-yl, 2-isoxazolin-3-yl, 1-methylimidazol-2-yl, and 1,3,4-oxadiazol-2-yl.
The aryl of the optionally substituted aryl represented by R
2
includes C6-C14 aryl such as phenyl, naphthyl (ex. 1-naphthyl and 2-naphthyl), and the like.
The optionally substituted heterocyclic group represented by R
2
includes an unsubstituted heterocyclic group and a substituted heterocyclic group. Examples of these heterocyclic groups are 5 to 7 membered heterocyclic groups having 1 to 4 hetero atoms selected from nitrogen, sulfur, and oxygen in the ring, specifically, pyridyl such as pyridin-2-yl, pyridin-3-yl, and pyridin-4-yl, pyrimidinyl such as pyrimidin-2-yl, pyrimidin-4-yl, and pyrimidin-5-yl, benzoxazolyl such as benzoxazol-2-yl, benzothiazolyl such as benzothiazol-2-yl, benzoimidazolyl, isoxazolyl such as isoxazol-3-yl and isoxazol-5-yl, isothiazolyl, thiadiazolyl such as 1,3,4-thiadiazolyl and 1,2,4-thiadiazolyl, pyridazinyl, pyrrolyl, pyrazolyl, furyl such as 2-furyl and 3-furyl, th
Kai Hiroyuki
Ohtsuka Toshikazu
Takase Akira
Powers Fiona T.
Shionogi & Co. Ltd.
Wenderoth Lind & Ponack LLP
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