2,5-dioxo-3-pyrroline-1-acetanilide fungicidal agents, compositions and method for use thereof
AssigneeAmerican Cyanamid Company
InventorsJerome M. Lavanish, Bomi Patel
Life of this patent
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Abstract
2,5-Dioxo-3-pyrroline-1-acetanilide compounds which are effective for the control or prevention of phytopathogenic fungi are described. A method for the fungicidal use of said compounds, fungicidal compositions containing said compounds and a method for the preparation of said compounds are also presented.
Claims19
A compound having the structural formula ##STR23## wherein R is hydrogen, halogen, or C.sub. -C.sub.4 alkyl optionally substituted with halogen;
- R.sub.1 is hydrogen, C.sub.1 -C.sub.10 alkyl optionally substituted with C.sub.1 -C.sub.9 alkoxy or halogen, C.sub.3 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.10 alkylthioalkyl, C.sub.4 -C.sub.10 cycloalkylalkyl, or phenyl or C.sub.7 -C.sub.10 phenylalkyl optionally substituted with one to three halogen atoms, C.sub.1 -C.sub.4 alkoxy groups, nitro groups, cyano groups, or C.sub.1 -C.sub.4 alkyl groups optionally substituted with halogen;
- R.sub.2 is hydrogen, or C.sub.1 -C.sub.6 alkyly optionally substituted with C.sub.1 -C.sub.5 alkoxy;
- L, M, Q, W and Z are each independently hydrogen, C.sub.1 -C.sub.6 alkyl optionally substituted with C.sub.1 -C.sub.4 alkoxy or halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.2 -C.sub.6 alkynyl, halogen, nitro, cyano, CO.sub.2 R.sub.3, or phenyl or phenoxy optionally substituted with one to three C.sub.1 -C.sub.4 alkoxy groups, halogen atoms, nitro groups, cyano groups, or C.sub.1 -C.sub.4 alkyl groups optionally substituted with halogen, with the proviso that at most only one of L, M, Q, W or Z may be phenyl or phenoxy;
- R.sub.3 is C.sub.1 -C.sub.4 alkyl;
- and when R.sub.1 is a substituent other than hydrogen, the optical isomers thereof;
- and with the proviso that when R.sub.1 is sec-propyl and R is hydrogen or methyl, then at least one of L, M, Q, W, or Z must be other than hydrogen.
A method for the protection of plants from the effects of plant pathogenic fungi which comprises applying to the locus of the plant or the fungi a fungicidally effective amount of a compound having the structural formula ##STR24## wherein R is hydrogen, halogen, or C.sub.1 -C.sub.4 alkyl optionally substituted with halogen;
- R.sub.1 is hydrogen, C.sub.1 -C.sub.10 alkyl optionally substituted with C.sub.1 C.sub.9 alkoxy or halogen, C.sub.3 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.10 alkylthioalkyl, C.sub.4 -C.sub.10 cycloalkylalkyl, or phenyl or C.sub.7 .gtoreq.C.sub.10 phenylalkyl optionally substituted with one to three halogen atoms, C.sub.-C.sub.4 alkoxy groups, nitro groups, cyano groups, or C.sub.1 -C.sub.4 alkyl groups optionally substituted with halogen;
- R.sub.2 is hydrogen, or C.sub.1 -C.sub.6 alkyly optionally substituted with C.sub.1 -C.sub.5 alkoxy;
- L, M, Q, W and Z are each independently hydrogen, C.sub.1 -C.sub.6 alkyl optionally substituted with C.sub.1 -C.sub.4 alkoxy or halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.2 -C.sub.6 alkynyl, halogen, nitro, cyano, CO.sub.2 R.sub.3, or phenyl or phenoxy optionally substituted with one to three C.sub.1 -C.sub.4 alkoxy groups, halogen atoms, nitro groups, cyano groups, or C.sub.1 -C.sub.4 alkyl groups optionally substituted with halogen, with the proviso that at most only one of L, M, Q, W or Z may be phenyl or phenoxy;
- R.sub.3 is C.sub.1 -C.sub.4 alkyl;
- and when R.sub.1 is a substituent other than hydrogen, the optical isomers thereof.
A fungicidal composition comprising an inert solid or liquid diluent and a fungicidally effective amount of a compound having the structural formula ##STR25## wherein R is hydrogen, halogen, or C.sub.1 -C.sub.4 alkyl optionally substituted with halogen;
- R.sub. is hydrogen, C.sub.1 -C.sub.10 alkyl optionally substituted with C.sub.1 -C.sub.9 alkoxy or halogen, C.sub.3 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.10 alkylthioalkyl, C.sub.4 -C.sub.10 cycloalkylalkyl, or phenyl or C.sub.7 -C.sub.10 phenylalkyl optionally substituted with one to three halogen atoms, C.sub.1 C.sub.4 alkoxy groups, nitro groups, cyano groups, or C.sub.1 -C.sub.4 alkyl groups optionally substituted with halogen;
- R.sub.2 is hydrogen, or C.sub.1 -C.sub.6 alkyly optionally substituted with C.sub.1 -C.sub.5 alkoxy;
- L, M, Q, W and Z are each independently hydrogen, C.sub.1 -C.sub.6 alkyl optionally substituted with C.sub.1 -C.sub.4 alkoxy or halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.2 -C.sub.6 alkynyl, halogen, nitro, cyano, CO.sub.2 R.sub.3, or phenyl or phenoxy optionally substituted with one to three C.sub.1 -C.sub.4 alkoxy groups, halogen atoms, nitro groups, cyano groups, or C.sub.1 -C.sub.4 alkyl groups optionally substituted with halogen, with the proviso that at most only one of L, M, Q, W or Z may be phenyl or phenoxy;
- R.sub.3 is C.sub.1 -C.sub.4 alkyl;
- and when R.sub.1 is a substituent other than hydrogen, the optical isomers thereof;
- and with the proviso that when R.sub.1 is sec-propyl and R is hydrogen or methyl, then at least one of L, M, Q, W, or Z must be other than hydrogen.
Dependencies are inferred from the claim text.