Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-11-13
2000-05-02
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514386, 5482634, 5482646, 5483167, 5483251, 5483255, 5482638, C07D24912, C07D23330, A01N 4374, A01N 4356
Patent
active
06057352&
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.
WO 94/11334 discloses certain amides and esters of Formula i as fungicides ##STR2## wherein n is 0-4; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.4 alkoxy; C.sub.1 -C.sub.4 haloalkoxy; or C.sub.1 -C.sub.4 alkylthio; C.sub.1 -C.sub.4 alkylcarbonylanrino, or C.sub.1 -C.sub.4 alkoxycarbonylamino; --C(.dbd.Z.sup.2)--;
EP-A-617,014 discloses certain amides and esters of Formula ii as fungicides ##STR3## wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl; alkoxycarbonyl, halogen, cyano, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 haloalkyl;
EP-A-656,351, WO 95/18789 and WO 95/21153 also disclose amides and esters similar to those in the above two publications as fungicides.
The cyclic amides of the present invention are not disclosed in any of the above publications.
J. Heterocyclic Chem., (1987), 24, 465, J. Heterocyclic Chem., (1988), 25, 1307, and Australian J. Chem., (1977), 30 (8), 1815 disclose 4-nitrophenyl isoxazoles (iii), phenyl pyrazolones (iv), and aryl isothiazolinones (v) respectively. ##STR4##
However, no utility as fungicides is alleged and the cyclic amides of the present invention are not disclosed therein.
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: ##STR5## wherein E is 1,2-phenylene optionally substituted with one of R.sup.3, R.sup.4, or both R.sup.3 and R.sup.4 ; floating double bond is attached to G; and when G is N, then A is N or CR.sup.14 and the floating double bond is attached to A; 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.4 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; 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 ; or R.sup.4 can be taken together as C.sub.3 -C.sub.5 alkylene, C.sub.3 -C.sub.5 haloalkylene, C.sub.3 -C.sub.5 alkenylene or C.sub.3 -C.sub.5 haloalkenylene each optionally substituted with 1-2 C.sub.1 -C.sub.3 alkyl; -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; --CHR.sup.15 OC(.dbd.O)O--; --CHR.sup.15 OC(.dbd.S)O--; --CHR.sup.15 OC(.dbd.O)S--; --CHR.sup.15 OC(.dbd.S)S--; --CHR.sup.15
REFERENCES:
patent: 4098896 (1978-07-01), Edwards
patent: 5108486 (1992-04-01), Kondo et al.
patent: 5416110 (1995-05-01), Wingert et al.
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patent: 5747516 (1998-05-01), Brown et al.
Zvilichovsky, G., J. Heterocyclic Chem., 24, 465-470, 1987.
Zvilichovsky, G. et al., J. Heterocyclic Chem., 25, 1307-1310, 1988.
Davis, M. et al., Australian J. Chem., 30(8), 1815-1818, 1977.
Brown Richard James
Frasier Deborah Ann
Howard, Jr. Michael Henry
Koether Gerard Michael
E. I. Du Pont de Nemours and Company
Rao Deepak R.
Shah Mukund J.
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