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US4515626A Expired / Lapsed US ⏱️ 0.0 years remaining

N-(Cyclopropyl-triazinyl-n'-(arylsulfonyl) ureas having herbicidal activity

Assignee: Novartis Corp
•
Filing: 1983-09-26
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Granted: 1985-05-07
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Expires: 2003-09-26
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Abstract

Abstract N-(Cyclopropyl-triazinyl- and -pyrimidinyl)-N'-arylsulfonyl ureas of the formula ##STR1## wherein Ar is a phenyl group ##STR2## or a naphthyl group ##STR3## and Q is a group X-A or R 3 , A is a C 3 -C 6 -alkynyl group, a C 1 -C 6 -alkyl group which is unsubstituted or substituted by halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl or C 1 -C 4 -haloalkylsulfonyl, or a C 2 -C 6 -alkenyl group which is unsubstituted or substituted by the groups given in the foregoing for C 1 -C 6 -alkyl, or A is a phenyl or benzyl group, E is the methine group or nitrogen, X is oxygen, sulfur, or a sulfinyl or sulfonyl bridge, Z is oxygen or sulfur, R 1 is hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, R 2 is halogen, C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, amino, C 1 -C 3 -alkylamino, di-(C 1 -C 3 -alkyl)amino, C 3 -C 6 -cycloalkyl or C 2 -C 6 -alkoxyalkyl, R 3 is hydrogen, halogen, C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl, C 1 -C 4 -haloalkyl, or a group --X-R 6 , --COZR 11 , --NO 2 or --CO-NR 8 R 9 , --CN, --COR 10 , --NR 1 R 7 or --NR 1 -COR 12 , R 4 is 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, halogen, or alkoxyalkyl having at most 4 carbon atoms, R 5 is the same as R 3 but independent thereof, R 6 and R 7 are each C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl or C 2 -C 6 -alkynyl, R 8 and R 9 independently of one another are each hydrogen, C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl or C 2 -C 6 -alkynyl, R 10 is hydrogen, C 1 -C 4 -alkyl or C 1 -C 3 -haloalkyl, R 11 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 3 -C 5 -alkenyl, C 3 -C 5 -alkynyl, phenyl or benzyl, and R 12 is the same as R 1 but independent thereof, and the salts of these compounds with amines, alkali metal bases or alkaline-earth metal bases or with quaternary ammonium bases, have good pre- and post-emergence-selective herbicidal and plant-growth-regulating properties.

Inventors

  • 👤 Henry Szczepanski

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 21:05
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/32; C07D239/42; A; A01; A01N; A01N47/00; A01N47/08; A01N47/28; A01N47/36; C07C; C07C45/00; C07C45/45; C07C45/455; C07D251/00; C07D251/02; C07D251/12; C07D251/14; C07D251/16; C07D251/18; C07D251/20; C07D251/22; C07D251/24; C07D521/00

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 408 words
An N-(cyclopropyl-triazinyl-)-N'-(arylsulfonyl)urea of the formula I ##STR21## wherein Ar is a phenyl group ##STR22## or a naphthyl group ##STR23## and Q is a group X-A or R 3 , A is a C 3 -C 6 -alkynyl group, a C 1 -C 6 -alkyl group which is unsubstituted or substituted by halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl or C 1 -C 4 -haloalkylsulfonyl, or a C 2 -C 6 -alkenyl group which is unsubstituted or substituted by the groups given in the foregoing for C 1 -C 6 -alkyl, or A is a phenyl or benzyl group, X is oxygen, sulfur, or a sulfinyl or sulfonyl bridge, Z is oxygen or sulfur, R 1 is hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, R 2 is halogen, C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, amino, C 1 -C 3 -alkylamino, di-(C 1 -C 3 -alkyl)amino, C 3 -C 6 -cycloalkyl or C 2 -C 6 -alkoxyalkyl, R 3 is hydrogen, halogen, C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl, C 1 -C 4 -haloalkyl, or a group --X--R 6 , --COZR 11 , --NO 2 or --CO--NR 8 R 9 , --CN, --COR 10 , --NR 1 R 7 or --NR 1 --COR 12 , R 4 is 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, halogen, or alkoxyalkyl having at most 4 carbon atoms, R 5 is the same as R 3 but independent thereof, R 6 and R 7 are each C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl or C 2 -C 6 -alkynyl, R 8 and R 9 independently of one another are each hydrogen, C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl or C 2 -C 6 -alkynyl, R 10 is hydrogen, C 1 -C 4 -alkyl or C 1 -C 3 -haloalkyl, R 11 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 3 -C 5 -alkenyl, C 3 -C 5 -alkynyl, phenyl or benzyl, and R 12 is the same as R 1 but independent thereof.
Claim 2
Dependent Claim 408 words
An N-(cyclopropyl-triazinyl-)-N'-(arylsulfonyl)urea of the formula I ##STR21## wherein Ar is a phenyl group ##STR22## or a naphthyl group ##STR23## and Q is a group X-A or R 3 , A is a C 3 -C 6 -alkynyl group, a C 1 -C 6 -alkyl group which is unsubstituted or substituted by halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl or C 1 -C 4 -haloalkylsulfonyl, or a C 2 -C 6 -alkenyl group which is unsubstituted or substituted by the groups given in the foregoing for C 1 -C 6 -alkyl, or A is a phenyl or benzyl group, X is oxygen, sulfur, or a sulfinyl or sulfonyl bridge, Z is oxygen or sulfur, R 1 is hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, R 2 is halogen, C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, amino, C 1 -C 3 -alkylamino, di-(C 1 -C 3 -alkyl)amino, C 3 -C 6 -cycloalkyl or C 2 -C 6 -alkoxyalkyl, R 3 is hydrogen, halogen, C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl, C 1 -C 4 -haloalkyl, or a group --X--R 6 , --COZR 11 , --NO 2 or --CO--NR 8 R 9 , --CN, --COR 10 , --NR 1 R 7 or --NR 1 --COR 12 , R 4 is 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, halogen, or alkoxyalkyl having at most 4 carbon atoms, R 5 is the same as R 3 but independent thereof, R 6 and R 7 are each C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl or C 2 -C 6 -alkynyl, R 8 and R 9 independently of one another are each hydrogen, C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl or C 2 -C 6 -alkynyl, R 10 is hydrogen, C 1 -C 4 -alkyl or C 1 -C 3 -haloalkyl, R 11 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 3 -C 5 -alkenyl, C 3 -C 5 -alkynyl, phenyl or benzyl, and R 12 is the same as R 1 but independent thereof.
Claim 3
Dependent Claim 10 words
A compound according to claim 1, wherein Z is oxygen.
Claim 4
Dependent Claim 60 words
A compound of the formula I according to claim 2, wherein Ar is a phenyl group substituted in the orthoposition by Q, R 1 is hydrogen or methyl, and R 2 is a C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy or C 1 -C 3 -alkylamino group.
Claim 5
Dependent Claim 26 words
A compound of the formula I according to claim 3, wherein Ar is a phenyl group substituted in the orthoposition by C 1 -C 4 -alkoxycarbonyl.
Claim 6
Dependent Claim 26 words
A compound of the formula I according to claim 3, wherein Ar is a phenyl group substituted in the orthoposition by C 1 -C 3 -haloalkoxy.
Claim 7
Dependent Claim 24 words
A compound of the formula I according to claim 3, wherein Ar is a phenyl group substituted in the orthoposition by halogen or nitro.
Claim 8
Dependent Claim 5 words
N-(4-Cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonylbenzenesulfonyl)urea according to claim 4.
Claim 9
Dependent Claim 5 words
N-(4-Cyclopropyl-6-ethoxy-1,3,5-triazin-2-yl)-N'-(2-difluoromethoxybenzenesulfonyl)urea according to claim 5.
Claim 10
Dependent Claim 24 words
A herbicidal and plant-growth-reducing composition which contains, as active ingredient, an effective amount of an N-phenylsulfonyl-N'-triazinyl-urea according to claim 1, together with a carrier.
Claim 11
Dependent Claim 27 words
A method of controlling undesirable plant growth, which method comprises applying thereto or to the locus thereof an effective amount of an N-(cyclopropyl-triazinyl)-N'-(arylsulfonyl)-urea according to claim 1.
Claim 12
Dependent Claim 26 words
A method of reducing plant growth, which method comprises applying thereto or to the locus thereof an effective amount of an N-(cyclopropyl-triazinyl)-N'-(arylsulfonyl)-urea according to claim 1.
Claim 13
Dependent Claim 35 words
A method for the pre- or post-emergence controlling of weeds in crops of cultivated plants, which method comprises applying thereto or to the locus thereof an effective amount of an N-(cyclopropyl-triazinyl)-N'-(arylsulfonyl)-urea according to claim 1.
Claim 14
Dependent Claim 29 words
A method of suppressing plant growth beyond the two-leaf stage, which method comprises applying before emergence of the plants an effective amount of an N-(cyclopropyl-triazinyl)-N'-(arylsulfonyl)-urea according to claim 1.

References Cited (Backward Citations)

US3441560A Cited
US3507958A Cited
EP0009419A1 Cited
EP0010560A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-05-06 1988-11-05 1989-05-07 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-05-06 1992-11-05 1993-05-07 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-05-06 1996-11-05 1997-05-07 $7700.00 Window Closed / Lapsed

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