US4594097A
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N-phenylsulfonyl-N'-triazinylureas
Assignee: Novartis Corp
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Filing: 1985-06-17
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Granted: 1986-06-10
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Expires: 2005-06-17
Abstract
Abstract N-Phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N'-triazinylureas of the general formula I ##STR1## wherein A is a radical of the formula --C.tbd.C--R, m is 1 or 2, Z is oxygen or sulfur, R is hydrogen; unsubstituted or substituted, branched or unbranched C 1 -C 9 alkyl; unsubstituted or substituted C 3 -C 9 cycloalkyl; unsubstituted or substituted phenyl; or an unsubstituted or substituted 5- or 6-membered aromatic heterocyclic ring, R 1 is hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl or a radical --Y--R 5 , R 2 is hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 1 -C 4 haloalkyl, or a radical --Y--R 5 , --COOR 6 , --NO 2 or --CO--NR 7 --R 8 , R 3 and R 4 , each independently of the other, are hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, halogen, C 2 -C 5 alkoxyalkyl, --NR 9 R 10 or --O--CH 2 --CH 2 --NR 9 R 10 , R 5 and R 6 , each independently of the other, are C 1 -C 5 alkyl, C 2 -C 5 alkenyl or C 2 -C 6 alkynyl, C 1 -C 5 haloalkyl, C 2 -C 5 haloalkenyl or C 2 -C 6 alkoxyalkyl, R 7 and R 8 , each independently of the other, are hydrogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl or C 2 -C 6 alkynyl, R 9 is hydrogen, methyl or ethyl, R 10 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, methoxymethyl, cyanomethyl, cyanoethyl, C 3 -C 5 alkenyl or C 3 -C 6 alkynyl, and Y is oxygen, sulfur, a sulfinyl or sulfonyl bridge and the salts of these compounds with amines, alkali metal bases or alkaline earth metal bases or with quaternary ammonium bases, have good preemergence and postemergence selective herbicidal and growth regulating properties.
Inventors
- 👤 Rolf Schurter
- 👤 Werner Fory
- 👤 Willy Meyer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 09:08
CPC Classifications
C; C07; C07D; C07D521/00; A; A01; A01N; A01N47/00; A01N47/08; A01N47/28; A01N47/36
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
471 words
N-phenylsulfonyl-N'-triazinylurea of the formula ##STR23## wherein A is a radical of the formula --C.tbd.C--R, m is 1 or 2, Z is oxygen or sulfur, R is hydrogen; branched or unbranched C 1 -C 9 alkyl which is unsubstituted or substituted by halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkoxy, C 3 -C 9 cycloalkyl, cyano, --COOR 6 , --CONR 7 R 8 or by phenyl which is in turn unsubstituted or substituted by halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, cyano or trifluoromethyl; or is C 3 -C 9 cycloalkyl which is unsubstituted or substituted by halogen, hydroxyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, cyano, --COOR 6 , --CONR 7 R 8 ; or is phenyl or phenyl substituted by halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, trifluoromethyl, --COOR 6 or --CONR 7 R 8 ; or is a 5- or 6-membered heterocyclic ring selected from the group consisting of furan, thiophene, pyrrole, pyrazole, triazole, pyridine, pyrimidine, pyridazine, triazine, thiazole, oxazole, thiadiazole and oxadiazole, which is unsubstituted or substituted by halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, --COOR 6 or --CONR 7 R 8 , R 1 is hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkyl, C 2 -C 5 alkenyl or a radical --Y--R 5 , R 2 is hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 1 -C 4 haloalkyl, or a radical --Y--R 5 , --COOR 6 , --NO 2 or --CO--NR 7 --R 8 , R 3 and R 4 , each independently of the other, are hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, halogen, C 2 -C 5 alkoxyalkyl, --NR 9 R 10 or --O--CH 2 --CH 2 --NR 9 R 10 , R 5 and R 6 , each independently of the other, are C 1 -C 5 alkyl, C 2 -C 5 alkenyl or C 2 -C 6 alkynyl, C 1 -C 5 haloalkyl, C 2 -C 5 haloalkenyl or C 2 -C 6 alkoxyalkyl, R 7 and R 8 , each independently of the other, are hydrogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl or C 2 -C 6 alkynyl, R 9 is hydrogen, methyl or ethyl, R 10 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, methoxymethyl, cyanomethyl, cyanoethyl, C 3 -C 5 alkenyl or C 3 -C 6 alkynyl, and Y is oxygen, sulfur, a sulfinyl or sulfonyl bridge, or a salt thereof.
Claim 2
Dependent Claim
471 words
N-phenylsulfonyl-N'-triazinylurea of the formula ##STR23## wherein A is a radical of the formula --C.tbd.C--R, m is 1 or 2, Z is oxygen or sulfur, R is hydrogen; branched or unbranched C 1 -C 9 alkyl which is unsubstituted or substituted by halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkoxy, C 3 -C 9 cycloalkyl, cyano, --COOR 6 , --CONR 7 R 8 or by phenyl which is in turn unsubstituted or substituted by halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, cyano or trifluoromethyl; or is C 3 -C 9 cycloalkyl which is unsubstituted or substituted by halogen, hydroxyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, cyano, --COOR 6 , --CONR 7 R 8 ; or is phenyl or phenyl substituted by halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, trifluoromethyl, --COOR 6 or --CONR 7 R 8 ; or is a 5- or 6-membered heterocyclic ring selected from the group consisting of furan, thiophene, pyrrole, pyrazole, triazole, pyridine, pyrimidine, pyridazine, triazine, thiazole, oxazole, thiadiazole and oxadiazole, which is unsubstituted or substituted by halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, --COOR 6 or --CONR 7 R 8 , R 1 is hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkyl, C 2 -C 5 alkenyl or a radical --Y--R 5 , R 2 is hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 1 -C 4 haloalkyl, or a radical --Y--R 5 , --COOR 6 , --NO 2 or --CO--NR 7 --R 8 , R 3 and R 4 , each independently of the other, are hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, halogen, C 2 -C 5 alkoxyalkyl, --NR 9 R 10 or --O--CH 2 --CH 2 --NR 9 R 10 , R 5 and R 6 , each independently of the other, are C 1 -C 5 alkyl, C 2 -C 5 alkenyl or C 2 -C 6 alkynyl, C 1 -C 5 haloalkyl, C 2 -C 5 haloalkenyl or C 2 -C 6 alkoxyalkyl, R 7 and R 8 , each independently of the other, are hydrogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl or C 2 -C 6 alkynyl, R 9 is hydrogen, methyl or ethyl, R 10 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, methoxymethyl, cyanomethyl, cyanoethyl, C 3 -C 5 alkenyl or C 3 -C 6 alkynyl, and Y is oxygen, sulfur, a sulfinyl or sulfonyl bridge, or a salt thereof.
Claim 3
Dependent Claim
28 words
A compound according to claim 1, wherein Z is oxygen and m is 1, and R 3 and R 4 together contain not more than 4 carbon atoms.
Claim 4
Dependent Claim
35 words
A compound according to claim 2, wherein A is in the 2- or 3-position to the sulfonyl group, R 1 is hydrogen and R 2 is in the 5- or 6-position to the sulfonyl group.
Claim 5
Dependent Claim
109 words
A compound according to claim 3, wherein R 2 is hydrogen, chlorine, fluorine, nitro, trifluoromethyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxycarbonyl or C 1 -C 4 alkoxy, each of R 3 and R 4 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, dialkylamino, C 1 -C 3 haloalkoxy, halogen or alkoxyalkyl, R is hydrogen or branched or unbranched C 1 -C 4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, methoxy, methylthio, C 1 -C 4 haloalkoxy, cyclopropyl, cyano, methoxycarbonyl, or is phenyl, pyridyl, thienyl or furyl; and R is in the 2- or 3-position.
Claim 6
Dependent Claim
5 words
N-[2-(propyn-1-yl)-6-chlorophenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea according to claim 1.
Claim 7
Dependent Claim
5 words
N[2-(propyn-1-yl)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea according to claim 1.
Claim 8
Dependent Claim
22 words
A herbicidal and plant growth-inhibiting composition which contains at least one N-phenylsulfonyl-N'-triazinylurea according to claim 1, together with carriers and/or other adjuvants.
Claim 9
Dependent Claim
25 words
A method of controlling undesired plant growth which comprises applying to said plant growth a herbicidally effective amount of a N-phenylsulfonyl-N'-triazinylurea according to claim 1.
Claim 10
Dependent Claim
24 words
A method of inhibiting plant growth, which comprises applying to said plants a growth inhibiting effective amount of a N-phenylsulfonyl-N'-triazinylurea according to claim 1.
Claim 11
Dependent Claim
18 words
A method according to claim 8 for selectively controlling weeds pre- or postemergence in crops of useful plants.
Claim 12
Dependent Claim
15 words
A method according to claim 9 for inhibiting plant growth beyond the 2-leaf stage preemergence.
Claim 13
Dependent Claim
14 words
A method according to claim 9 for inhibiting the growth of leguminous cover crops.
Claim 14
Dependent Claim
13 words
A method according to claim 9 for inhibiting the sprouting of stored potatoes.
Claim 15
Dependent Claim
19 words
A method according to claim 10, wherein the crops of useful plants are cereals, cotton, soybeans, maize and rice.
References Cited (Backward Citations)
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