Fungicidal cyclic amides

Details Fungicidal cyclic amides Fungicidal cyclic amides

1997-08-21

1999-10-05

Richter, Johann

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Silicon containing doai

514384, 514385, 514184, 5482636, 5482638, 5482642, 5482646, 5482656, 5482664, 5482632, 5482648, A01N 5510, A01N 5502, A01N 43653, C07D24912

Patent

active

059624361

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

This invention relates to certain cyclic amides, their N-oxides, agriculturally-suitable salts and compositions, and methods of their use as fungicides.
The control of plant diseases caused by fungal plant pathogens is extremely important in achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
EP 260,794, EP 363,818, EP 398,692, WO 93/07116, WO 93/15046, EP 463,488, and EP 585,751 disclose certain non-cyclic fungicidal amides. The cyclic amides of this invention are not disclosed therein.
EP 508,126, WO 95/01971, U.S. Pat. No. 4,098,896, and WO 92/16510 disclose certain cyclic amides as fungicides, herbicides or insecticides. The cyclic amides of this invention are not disclosed therein.
J. Heterocyclic Chem., (1987), 24, 465, J. Heterocyclic Chem., (1988), 25, 1307, and Australian J. Chem., (1977), 30 (8), 1815 disclose 4-nitrophenyl isoxazoles (i), phenyl pyrazolones (ii), and aryl isothiazolinones (iii) respectively. ##STR1##
However, no utility as fungicides is alleged and no ortho-substituted compounds of the present invention are disclosed.


SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally-suitable salts thereof, agricultural compositions containing them and their use as fungicides: ##STR2## wherein: A is O; S; N; NR.sup.5 ; or CR.sup.14 ; floating double bond is attached to G; and when G is N, A is N or CR.sup.14 and the floating double bond is attached to A; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; or C.sub.2 -C.sub.4 alkoxycarbonyl; -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; C.sub.2 -C.sub.4 alkoxycarbonyl; hydroxy; C.sub.1 -C.sub.2 alkoxy; or acetyloxy; hydroxy; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.2 -C.sub.6 alkenyloxy; C.sub.2 -C.sub.6 alkynyloxy; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; formyl; C.sub.2 -C.sub.6 alkylcarbonyl; C.sub.2 -C.sub.6 alkoxycarbonyl; NH.sub.2 C(O); (C.sub.1 -C.sub.4 alkyl)NHC(O); (C.sub.1 -C.sub.4 alkyl).sub.2 NC(O); Si(R.sup.25).sub.3 ; Ge(R.sup.25).sub.3 ; (R.sup.25).sub.3 Si--C.tbd.C--; or phenyl, phenylethynyl, benzoyl, or phenylsulfonyl each substituted with R.sup.8 and optionally substituted with one or more R.sup.10 ; --CH(OR.sup.6)--; --CHR.sup.6 --; --CHR.sup.6 CHR.sup.6 --; --CR.sup.6 .dbd.CR.sup.6 --; --C.tbd.C--; --CHR.sup.6 O--; --OCHR.sup.6 --; --CHR.sup.6 S(O).sub.n --; --S(O).sub.n CHR.sup.6 --; --CHR.sup.6 O--N.dbd.C(R.sup.7)--; --(R.sup.7)C.dbd.N--OCH(R.sup.6)--; --C(R.sup.7).dbd.N--O--; --O--N.dbd.C(R.sup.7)--; --CHR.sup.6 OC(.dbd.O)N(R.sup.15)--; or a direct bond; and the directionality of the Y linkage is defined such that the moiety depicted on the left side of the linkage is bonded to the phenyl ring and the moiety on the right side of the linkage is bonded to Z; -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; C.sub.1 -C.sub.6 haloalkylthio; C.sub.1 -C.sub.6 haloalkylsulfinyl; C.sub.1 -C.sub.6 haloalkylsulfonyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub

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