4(3H)-Oxobenzo-2,1,3-thiadiazine-2,2-dioxides
AssigneeThe Dow Chemical Company
InventorsLennon H. McKendry, Walter P. Bland
Life of this patent
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Abstract
Disclosed are certain novel substituted 4(3H)-oxobenzo-2,1,3-thiadiazine-2,2-dioxide compounds and derivatives thereof and compositions and methods employing the same in the control of undesired vegetation.
Claims33
A compound of the formula:
- ##STR32## wherein:
- each X independently represents halo, YR.sup.2 , Y'CF.sub.2 C(Z).sub.3, CF.sub.3, nitro, or loweralkyl, with the proviso that at least one X is always halo or nitro;
- n represents an integer of from 1 to 4, inclusive;
- R represents straight or branched alkyl and haloalkyl, each of 1 to 6 carbon atoms;
- alkenyl, haloalkenyl, alkynyl and haloalkynyl, each of 3 to 6 carbon atoms, cyanoalkyl, alkylthioalkyl or alkoxyalkyl, each of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, benzyl, phenyl, loweralkylphenyl and halophenyl;
- R.sup.1 represents ##STR33## R.sup.2 represents haloalkyl of 1 to 4 carbon atoms;
- alkenyl of 3 to 6 carbon atoms;
- cycloalkyl or 3 to 6 carbon atoms;
- phenyl, loweralkylphenyl and halophenyl;
- R.sup.3 represents alkyl of 1 to 4 carbon atoms, and cycloalkyl of 3 to 6 carbon atoms;
- R.sup.4 represents any of R.sub.3 and alkoxy containing 1 to 4 carbon atoms, and R.sup.3 and R.sup.4 when taken together constitutes a 4 to 6 carbon heterocyclic radical together with the nitrogen from which each depends;
- and
- R.sup.5 represents alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 5 carbons, alkenyl, haloalkenyl, alkoxyalkyl or alkylthioalkyl, each of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbons, alkoxycarbonylalkyl of 4 to 8 carbon atoms, phenyl, loweralkylphenyl and halophenyl;
- R.sup.6 represents straight or branched alkyl or haloalkyl of 1 to 7 carbon atoms;
- alkenyl and haloalkenyl of 3 to 6 carbon atoms;
- cycloalkyl of 3 to 6 carbon atoms;
- phenyl, loweralkylphenyl and halophenyl;
- Y and Y' independently represent a chalcogen group having an atomic number of from 8 to 16, inclusive;
- and
- each Z independently represents bromo, chloro, fluoro, or hydrogen.
A method for controlling undesired plants which comprises applying to said plants and/or their habitats a herbicidally effective amount of a compound corresponding to the formula:
- ##STR35## wherein:
- each X independently represents halo, YR.sup.2, Y'CF.sub.2 C(Z).sub.3, CF.sub.3, nitro, or loweralkyl with the proviso that at least one X is always halo or nitro;
- n represents an integer of from 1 to 4, inclusive;
- R represents straight or branched alkyl and haloalkyl, each of 1 to 6 carbon atoms;
- alkenyl, haloalkenyl, alkynyl and haloalkynyl, each of 3 to 6 carbon atoms, cyanoalkyl, alkylthioalkyl or alkoxyalkyl, each of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, benzyl, phenyl, loweralkylphenyl and halophenyl;
- R.sup.1 represents ##STR36## R.sup.2 represents haloalkyl of 1 to 4 carbon atoms;
- alkenyl of 3 to 6 carbon atoms;
- cycloalkyl or 3 to 6 carbon atoms;
- phenyl, loweralkylphenyl and halophenyl;
- R.sup.3 represents alkyl or 1 to 4 carbon atoms, and cycloalkyl of 3 to 6 carbon atoms;
- R.sup.4 represents any of R.sup.3 and alkoxy containing 1 to 4 carbon atoms, and R.sup.3 and R.sup.4 when taken together constitutes a 4 to 6 carbon heterocyclic radical together with the nitrogen from which each depends;
- and
- R.sup.5 represents alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 5 carbons, alkenyl, haloalkenyl, alkoxyalkyl or alkylthioalkyl, each of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbons, alkoxycarbonylalkyl of 4 to 8 carbon atoms, phenyl, loweralkylphenyl and halophenyl;
- R.sup.6 represents straight or branched alkyl or haloalkyl of 1 to 7 carbon atoms;
- alkenyl and haloalkenyl of 3 to 6 carbon atoms;
- cycloalkyl of 3 to 6 carbon atoms;
- phenyl, loweralkylphenyl and halophenyl;
- Y and Y' independently represent a chalcogen group having an atomic number of from 8 to 16, inclusive;
- and
- each Z independently represents bromo, chloro, fluoro, or hydrogen.
A herbicidal composition comprising a herbidical amount of a compound corresponding to the formula:
- ##STR38## wherein:
- each X independently represents halo, YR.sup.2, Y'CF.sub.2 C(Z).sub.3, CF.sub.3, nitro, or loweralkyl, with the proviso that at least one X is always halo or nitro;
- n represents an integer of from 1 to 4, inclusive;
- R represents straight or branched alkyl and haloalkyl, each of 1 to 6 carbon atoms;
- alkenyl, haloalkenyl, alkynyl and haloalkynyl, each of 3 to 6 carbon atoms, cyanoalkyl, alkylthioalkyl or alkoxyalkyl, each of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, benzyl, phenyl, loweralkylphenyl and halophenyl;
- R.sup.1 represents ##STR39## R.sup.2 represents haloalkyl of 1 to 4 carbon atoms;
- alkenyl of 3 to 6 carbon atoms;
- cycloalkyl or 3 to 6 carbon atoms;
- phenyl, loweralkylphenyl and halophenyl;
- R.sup.3 represents alkyl or 1 to 4 carbon atoms;
- and cycloalkyl of 3 to 6 carbon atoms;
- R.sup.4 represents any of R.sup.3 and alkoxy containing 1 to 4 carbon atoms, and R.sup.3 and R.sup.4 when taken together constitutes a 4 to 6 carbon heterocyclic radical together with the nitrogen from which each depends;
- and
- R.sup.5 represents alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 5 carbons, alkenyl, haloalkenyl, alkoxyalkyl or alkylthioalkyl, each of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon, alkoxycarbonylalkyl of 4 to 8 carbon atoms, phenyl, loweralkylphenyl and halophenyl;
- R.sup.6 represents straight of branched alkyl or haloalkyl of 1 to 7 carbon atoms;
- alkenyl and haloalkenyl of 3 to 6 carbon atoms;
- cycloalkyl of 3 to 6 carbon atoms;
- phenyl, loweralkylphenyl and halophenyl;
- Y and Y' independently represent a chalcogen group having an atomic number of from 8 to 16, inclusive;
- and
- each Z independently represents bromo, chloro, fluoro, or hydrogen.
The method for the selective control of undesired plants in the presence of soybean plants which comprises contacting said plants with a herbicidally effective amount of a compound corresponding to the formula:
- ##STR41## wherein:
- each X independently represents halo, YR.sup.2, Y'CF.sub.2 C(Z).sub.3, CF.sub.3, nitro, or loweralkyl, with the proviso that at least one X is always halo or nitro;
- n represents an integer of from 1 to 4, inclusive;
- R represents straight or branched alkyl and haloalkyl, each of 1 to 6 carbon atoms;
- alkenyl, haloalkenyl, alkynyl and haloalkynyl, each of 3 to 6 carbon atoms, cyanoalkyl, alkylthioalkyl or alkoxyalkyl, each of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, benzyl, phenyl, loweralkylphenyl and halophenyl;
- R.sup.1 represents ##STR42## R.sup.2 represents haloalkyl of 1 to 4 carbon atoms;
- alkenyl of 3 to 6 carbon atoms;
- cycloalkyl or 3 to 6 carbon atoms;
- phenyl, loweralkylphenyl and halophenyl;
- R.sup.3 represents alkyl or 1 to 4 carbon atoms, and cycloalkyl of 3 to 6 carbon atoms;
- R.sup.4 represents any of R.sup.3 and alkoxy containing 1 to 4 carbon atoms, and R.sup.3 and R.sup.4 when taken together constitutes a 4 to 6 carbon heterocyclic radical together with the nitrogen from which each depends;
- and
- R.sub.5 represents alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 5 carbons, alkenyl, haloalkenyl, alkoxyalkyl or alkylthioalkyl, each of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbons, alkoxycarbonylalkyl of 4 to 8 carbon atoms, phenyl, loweralkylphenyl and halophenyl;
- R.sup.6 represents straight or branched alkyl or haloalkyl of 1 to 7 carbon atoms;
- alkenyl and haloalkenyl of 3 to 6 carbon atoms;
- cycloalkyl of 3 to 6 carbon atoms;
- phenyl, loweralkylphenyl and halophenyl;
- Y and Y' independently represent a chalcogen group having an atomic number of from 8 to 16, inclusive;
- and
- each Z independently represents bromo, chloro, fluoro, or hydrogen.
Dependencies are inferred from the claim text.