Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-12-04
2002-03-26
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S231500, C514S252130, C514S256000, C514S259500, C514S311000, C514S317000, C514S365000, C514S374000, C544S111000, C544S283000, C544S333000, C544S359000, C546S164000, C546S207000, C546S208000, C548S146000, C548S215000, C548S311100
Reexamination Certificate
active
06362212
ABSTRACT:
TECHNICAL FIELD
The present invention relates to an oxime derivative, particularly a heterocyclic compound substituted with &agr;-(o-substituted oxyimino)-2-substituted benzyl, a process for producing it, intermediates therefor, and a bactericide (fungicide) containing it as an active ingredient.
BACKGROUND ART
Compounds containing &agr;-(o-substituted oxyimino)-benzyl known so far include benzohydroxymoylazole derivatives having insecticidal activity (JP-A 1-308260, JP-A 5-1046, WO92/09581, JP-A 5-331011, JP-A 5-331012, JP-A 6-41086), oxime derivatives having insecticidal activity (JP-A 3-68559), 1-azolyl-substituted oxime ethers having fungicidal activity (JP-A 60-87269), etc.
The present invention is to provide a compound having more potent fungicidal activity, higher utility, etc., than the known compounds as well as low toxicity.
DISCLOSURE OF INVENTION
The present inventors have intensively studied to achieve the above object. As a result, it has been found that a heterocyclic compound substituted with &agr;-(-o-substituted oxyimino)-2-substituted benzyl has potent fungicidal activity. After further studies, the present invention has been completed.
The present invention provides:
1. A compound of the formula (I):
wherein R
1
is optionally substituted aryl, an optionally substituted heterocyclic group, mono or disubstituted methyleneamino, optionally substituted (substituted imino)methyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, substituted carbonyl or substituted sulfonyl; R
2
is alkyl, alkenyl, alkynyl or cycloalkyl; R
3
is an optionally substituted heterocyclic group; R
4
is hydrogen, alkyl, alkoxy, halogen, nitro, cyano or halogenated alkyl; M is an oxygen atom, S(O)
i
(in which i is 0, 1 or 2), NR
16
(in which R
16
is hydrogen, alkyl or acyl) or a single bond; n is 0 or 1, provided that, when R
3
is imidazol-1-yl or 1H-1,2,4-triazol-1-yl, n is 1; and~indicates an E- or Z-isomer or a mixture thereof; or a salt thereof;
2. A compound according to the above item 1, wherein the optionally substituted heterocyclic group represented by R
1
is pyridyl, pyrimidinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, isoxazolyl, isothiazolyl, thiadiazolyl, pyridazinyl, pyrrolyl, pyrazolyl, furyl, thienyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, triazolyl, quinolyl, indolyl, benzisothiazolyl, benzisoxazolyl or pyrazinyl, each of which is unsubstituted or substituted, or a salt thereof;
3. A compound according to the above item 1, wherein R
1
is phenyl or a heterocyclic group, each of which is unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of halogen, lower alkyl, halogenated lower alkyl, lower alkoxy, lower alkylthio, phenyl, phenoxy and nitro, or a salt thereof;
4. A compound according to the above item 1, wherein R
1
is phenyl; phenyl substituted with halogen and/or lower alkyl; or pyridyl substituted with halogen and/or halogenated lower alkyl; or a salt thereof:
5. A compound according to the above item 1, wherein R
1
is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 4-chloro-2-methylphenyl, 2-chloropyridin-3-yl, 3,5-dichloro-pyridin-2-yl, 5-trifluoromethylpyridin-2-yl, 5-trifluoromethyl-3-chloropyridin-2-yl or 3-trifluoromethyl-5-chloropyridin-2-yl, or a salt thereof;
6. A compound according to the above item 1, wherein R
1
is a group of the formula (a):
wherein R
9
and R
10
are the same or different and are hydrogen, optionally substituted alkyl, acyl, alkylthio, alkylsulfinyl alkylsulfonyl, optionally substituted amino, cycloalkyl, optionally substituted aryl or an optionally substituted heterocyclic group, or R
9
and R
10
are linked together to form a monocyclic or polycyclic ring which may contain a heteroatom, or a salt thereof;
7. A compound according to the above item 1, wherein R
9
and R
10
are the same or different and are hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, optionally substituted phenyl, optionally substituted naphthyl or an optionally substituted heterocyclic group, or R
9
and R
10
are linked together to form a cyclopentane or cyclohexane ring which may form a condensed ring with another ring, or a salt thereof;
8. A compound according to the above item 1, wherein R
9
is phenyl which is unsubstituted or substituted with 1 to 3 substituents selected from the group consisting of halogen, optionally substituted alkyl, optionally substituted hydroxyl, alkylthio, optionally substituted amino, nitro, phenyl and cyano, or a salt thereof;
9. A compound according to the above item 1, wherein R
9
is phenyl which is unsubstituted or substituted with 1 to 3 substituents selected from the group consisting of chlorine, methyl, trifluoromethyl and methoxy, or a salt thereof;
10. A compound according to the above item 1, wherein R
9
is morpholino, pyridyl, pyridazinyl, pyrazolyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, benzothiazolyl, quinolyl, quinazolinyl or pyrazinyl, each of which is unsubstituted or substituted, or a salt thereof;
11. A compound according to the above item 1, wherein R
10
is hydrogen or alkyl, or a salt thereof;
12. A compound according to the above item 1, wherein R
10
is hydrogen, methyl or ethyl, or a salt thereof;
13. A compound according to the above item 1, wherein R
2
is alkyl or alkenyl, or a salt thereof;
14. A compound according to the above item 1, wherein R
2
is methyl, ethyl or allyl, or a salt thereof;
15. A compound according to the above item 1, wherein R
3
is isoxazolyl, oxazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrrolyl, pyrazolyl, furyl, thienyl, imidazolyl, triazolyl, tetrazolyl, oxadiazolyl, thiazolinyl, isoxazolinyl, imidazolinyl, oxazolinyl or thiazolidinyl, each of which is unsubstituted or substituted, or a salt thereof;
16. A compound according to the above item 1, wherein R
3
is imidazolyl; imidazolyl substituted with lower alkyl; imidazolinyl; triazolyl; imidazolinyl substituted with lower alkyl; isoxazolyl; isoxazolyl substituted with lower alkyl; oxadiazolyl; oxadiazolyl substituted with lower alkyl; isoxazolinyl; isoxazolinyl substituted with lower alkyl; oxazolinyl; pyrazolyl; pyrazolyl substituted with lower alkyl; thiazolinyl; furyl; tetrazolyl substituted with lower alkyl; oxazolyl; isothiazolyl substituted with lower alkyl; thiazolidinyl; or thiazolidinyl substituted with lower alkyl; or a salt thereof;
17. A compound according to the above item 1, wherein R
3
is imidazol-1-yl, imidazol-2-yl, 1-methylimidazol-2-yl, 2-methylimidazol-1-yl, 4-methylimidazol-1-yl, 5-methylimidazol-1-yl, 2-imidazolin-2-yl, 1H-1,2,4-triazol-1-yl, 1-methyl-2-imidazolin-2-yl, isoxazol-3-yl, 3-methylisoxazol-5-yl, 5-methylisoxazol-3-yl, 5-methyl-1,2,4-oxadiazol-3-yl, 3-ethyl-1,2,4-oxadiazol-5-yl, 2-isoxazolin-3-yl, 2-oxazolin-2-yl, 3-methyl-2-isoxazolin-5-yl, pyrazol-1-yl, 1-methylpyrazol-5-yl, 2-thiazolin-2-yl, 2-furyl, 3-methylisothiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 5-methyl-1,3,4-oxadiazol-2-yl, 2-methyltetrazol-5-yl, oxazol-5-yl, isoxazol-5-yl, thiazolidin-2-yl or 3-methylthiazolidin-2-yl, or a salt thereof;
18. A compound according to the above item 1, wherein R
4
is hydrogen, or a salt thereof;
19. A compound according to the above item 1, wherein M is an oxygen atom, or a salt thereof;
20. A fungicidal composition comprising a compound according to any one of the above items 1 to 19 or a salt thereof as an active ingredient;
21. A process for producing a compound of the formula (I):
wherein each symbol is as defined in the above item 1, which comprises reacting the compound of the formula (V):
wherein A is halogen and the other symbols are as defined in the above item 1, with a compound of the formula (X):
R
3
—H (X)
wherein R
3
is an optionally substituted heterocyclic group;
22. A process according to the above item 21, wherein R
3
is pyrrolyl, imidazolyl, pyrazolyl or tria
Iwakawa Tsuneo
Kai Hiroyuki
Masuko Michio
Nishida Kuniyoshi
Takase Akira
Foley & Lardner
Raymond Richard L.
Shionogi & Company, Ltd.
Truong Tamthom N.
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