1,2,3-Thiadiazole-5-carboxylic acid derivatives, herbicidal and growth regulating compositions containing the same and process for making same
First Claim
1. A comound of the formula ##STR14## wherein R1 is hydrogen, C1 -C4 alkyl, chloromethyl, or bromomethyl;
- andX has the formula ##STR15## where R3 and R4 are the same or different and are hydrogen, C1 -C18 alkyl, mono- or disubstituted C1 -C18 alkyl substituted in the 1-, 2- or 3-position by halogen, C1 -C6 alkoxy, phenoxy, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl or cyano, tetrahydrofurfuryl, C3 -C8 cycloalkylmethyl, C2 -C8 2- or 3-alkenyl or alkinyl, phenyl or diphenyl C1 -C3 alkyl, mono- or disubstituted benzyl substituted by one or more of halogen, methylenedioxy, C1 -C6 alkyl, C1 -C6 alkoxy, trifluoromethyl or nitro, α
-methyl- or α
,α
-dimethylbenzyl, pyridyl, furfuryl, C3 -C8 cycloalkyl, C1 -C6 alkyl or ethinyl substituted C3 -C8 cycloalkyl, phenyl, mono- or disubstituted phenyl substituted by one or more of halogen, methylenedioxy, C1 -C6 alkyl, C1 -C6 alkoxy, trifluoromethyl or nitro, or naphthyl, or R3 and R4 together with the adjoining nitrogen atom constitute a morpholine, piperidine or pyrrolidine group.
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Abstract
1,2,3-thiadiazole-5-carboxylic acid derivatives having herbicidal and growth regulating activity and having the formula ##STR1## in which R1 is hydrogen or is alkyl of which the chain may be interrupted in one or several places by oxygen or sulfur or which may be substituted by halogen and in which
X is
(a) --Y--R2, wherein R2 is hydrogen, alkyl which may be substituted, aryl which may also be substituted, aryl-C1 -C2 -alkyl which may also be substituted, or a univalent metal equivalent and wherein Y is oxygen or sulfur, or
(b) wherein X constitutes the residue ##STR2## wherein R3 and R4 may be the same or different and have the meaning further defined in claim 1 of the accompanying specification.
The compounds are soil- or leaf-applicable herbicides with a high activity against seed weeds and resistant weeds.
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Citations
66 Claims
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1. A comound of the formula ##STR14## wherein R1 is hydrogen, C1 -C4 alkyl, chloromethyl, or bromomethyl;
- and
X has the formula ##STR15## where R3 and R4 are the same or different and are hydrogen, C1 -C18 alkyl, mono- or disubstituted C1 -C18 alkyl substituted in the 1-, 2- or 3-position by halogen, C1 -C6 alkoxy, phenoxy, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl or cyano, tetrahydrofurfuryl, C3 -C8 cycloalkylmethyl, C2 -C8 2- or 3-alkenyl or alkinyl, phenyl or diphenyl C1 -C3 alkyl, mono- or disubstituted benzyl substituted by one or more of halogen, methylenedioxy, C1 -C6 alkyl, C1 -C6 alkoxy, trifluoromethyl or nitro, α
-methyl- or α
,α
-dimethylbenzyl, pyridyl, furfuryl, C3 -C8 cycloalkyl, C1 -C6 alkyl or ethinyl substituted C3 -C8 cycloalkyl, phenyl, mono- or disubstituted phenyl substituted by one or more of halogen, methylenedioxy, C1 -C6 alkyl, C1 -C6 alkoxy, trifluoromethyl or nitro, or naphthyl, or R3 and R4 together with the adjoining nitrogen atom constitute a morpholine, piperidine or pyrrolidine group. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66)
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Specification
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- Resources
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Current AssigneeSchering Ag (Merck & Co., Inc.)
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Original AssigneeSchering Ag (Merck & Co., Inc.)
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InventorsKruger, Hans-Rudolf, Rusch, Reinhart, Arndt, Friedrich
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Primary Examiner(s)Rotman, Alan L.
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Assistant Examiner(s)Bond, Robert T.
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Application NumberUS05/918,462Time in Patent Office529 DaysField of Search260/293.68, 260/302 D, 260/294.8 D, 544/134, 71/90US Class Current504/225CPC Class CodesA01N 43/82 five-membered rings with th...C07D 285/06 1,2,3-Thiadiazoles; Hydroge...
