2-(substituted phenyl)-2-alkoxyimino-N-alkylacetamide compounds

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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514351, 546291, 546296, 546297, 546176, 564164, 564165, A01N 4340, C07D21364, C07D21369, C07C25140

Patent

active

057706140

DESCRIPTION:

BRIEF SUMMARY
CROSS-REFERENCE

This application is a 371 of PCT/JP95/00902 filed May 11, 1995.


TECHNICAL FIELD

The present invention relates to 2-(substituted phenyl)-2-alkoxyimino-N-alkylacetamide compounds and fungicides containing them, in particular, a composition for controlling Pseudocercosporella herpotrichoides.


BACKGROUND OF THE INVENTION

Certain alkoxyiminoacetamide derivatives are known to have fungicidal activity against certain pathogens (JP-A 3-246268, JP-A 4-182461). However, their fungicidal activity against wheat eyespot (Pseudocercosporella herpotrichoides), which is a serious pathogen of wheat, has not been known.
The present invention is to provide a novel compound which has a broad fungicidal spectrum and potent controlling activity particularly against Pseudocercosporella herpotrichoides, and a novel composition to control Pseudocercosporella herpotrichoides.


DISCLOSURE OF THE INVENTION

The present inventors have intensively studied to achieve the above object. As a result, it has been found that 2-(substituted phenyl)-2-alkoxyimino-N-alkylacetamide compounds have potent fungicidal activity against Pseudocercosporella herpotrichoides and that a novel 2-(substituted phenyl)-2-methoxyimino-N-methylacetamide compound included in the above compounds has not only potent fungicidal activity against Pseudocercosporella herpotrichoides but also a broad fungicidal spectrum. Thus, the present invention has been completed.
The present invention provides:
(1) A compound of the formula (I-A): ##STR1## wherein A.sup.1 is 3,4-dimethylphenyl or 3,5-dimethylphenyl, and .about. indicates a configuration of an E- or Z-isomer or a mixture thereof;
(2) A compound of the formula (I-B): ##STR2## wherein A.sup.2 is 3-chloro-2-pyridyl, 5-chloro-2-pyridyl, 3-trifluoromethyl-2-pyridyl, 4-trifluoromethyl-2-pyridyl, 6-trifluoromethyl-2-pyridyl, 6-methoxy-2-pyridyl, 6-isopropoxy-2-pyridyl, 6-methylthio-2-pyridyl, 5-chloro-3-trifluoromethyl-2-pyridyl, 6-methoxy-3-trifluoromethyl-2-pyridyl, 6-isopropoxy-3-trifluoromethyl-2-pyridyl,6-chloro-4-trifluoromethyl-2-pyri dyl, 3,5,6-trichloro-4-trifluoromethyl-2-pyridyl, 6-chloro-3,5-di(trifluoromethyl)-2-pyridyl, 6-methoxy-5-trifluoromethyl-2-pyridyl, 6-isopropoxy-5-trifluoromethyl-2-pyridyl, 6-methylamino-5-trifluoromethyl-2-pyridyl, 3,6-dichloro-5-trifluoromethyl-2-pyridyl or 2-quinolyl, and .about. indicates a configuration of an E- or Z-isomer or a mixture thereof, or a salt thereof;
(3) A compound according to the above item (2), wherein A.sup.2 is 3-trifluoromethyl-2-pyridyl or 5-chloro-3-trifluoromethyl-2-pyridyl, or a salt thereof;
(4) A fungicidal composition which comprises as an active ingredient a compound of the formula (I-A) or (I-B) or a salt thereof;
(5) A composition for controlling Pseudocercosporella herpotrichoides, which comprises as an active ingredient a compound of the formula (I-A) or (I-B) or a salt thereof;
(6) A composition for controlling Pseudocercosporella herpotrichoides, which comprises as an active ingredient a compound of the formula (I): ##STR3## wherein A.sup.3 is optionally substituted phenyl, optionally substituted pyridyl or optionally substituted quinolyl, R.sup.1 and R.sup.2 are the same or different and are alkyl, n is 0 or 1, and .about. indicates a configuration of an E- or Z-isomer or a mixture thereof, or a salt thereof; and
(7) A composition according to the above item (6), wherein R.sup.1 and R.sup.2 are methyl.
The term "lower" used herein means having 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, unless otherwise indicated.
A.sup.2 in the formula (I-B) is preferably 3-trifluoromethyl-2-pyridyl or 5-chloro-3-trifluoromethyl-2-pyridyl.
The optionally substituted pyridyl and optionally substituted quinolyl represented by A.sup.3 in the formula (I) may have a bond to the oxygen atom at any possible position, but preferably they have the bond at the 2-position.
Each of the optionally substituted phenyl, optionally substituted pyridyl and optionally substituted quinolyl represented by A.sup

REFERENCES:
patent: 5183921 (1993-02-01), Takase et al.
Koehle et al., "Biokinetic properties of BAS 490 F and some related compounds", Biochem. Soc. Trans., vol. 22, No. 1, pp. 65S, 1993.
Urashima et al., "Varietal resistance and chemical control of wheat blast fungus", Summa Phytopathol., vol. 20, No. 2, pp. 107-112, 1994.

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