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US4690707A Expired / Lapsed US ⏱️ 0.0 years remaining

Sulfonylureas

Assignee: Novartis Corp
•
Filing: 1985-10-04
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Granted: 1987-09-01
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Expires: 2005-10-04
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Abstract

Abstract The invention relates to N-pyridylsulfonyl-N'-pyrimidinyl- and -N'-triazinylureas of the formula I ##STR1## wherein A is a C 3 -C 6 alkynyl radical, a C 1 -C 6 alkyl radical which is 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 is a C 2 -C 4 alkenyl radical which is unsubstituted or substituted as for C 1 -C 6 alkyl, or is a phenyl radical which is unsubstituted or substituted by halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, an --X--C 1 --C 4 --alkyl, C 1 -C 4 alkoxycarbonyl, amino, mono- or di-(C 1 -C 4 alkyl)amino, carbamoyl, mono- or di-(C 1 -C 4 alkyl)carbamoyl, sulfamoyl, mono- or di-(C 1 -C 4 alkyl)sulfamoyl radical or A--X-- forms an amino radical --NR 6 R 7 , E is the methine group or nitrogen, R 1 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 2 -C 5 alkoxyalkoxy, C 1 -C 5 alkylthio, C 1 -C 5 alkylsulfinyl or C 1 -C 5 alkylsulfonyl, R 2 is C 1 -C 3 alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms, or is C 1 -C 2 alkoxy, R 3 is hydrogen, halogen, an amino group --NR 4 R 5 , or C 1 -C 3 alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms, or is C 1 -C 4 alkoxy which is unsubstituted or substituted by methoxy, ethoxy or 1 to 3 halogen atoms, R 4 is hydrogen or methyl, R 5 is hydrogen, C 1 -C 2 alkyl or methoxy, R 6 and R 7 are each independently hydrogen, C 1 -C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 alkoxyalkyl, C 1 -C 4 cyanoalkyl, or both together with the nitrogen atom to which they are attached also form a saturated 5- or 6-membered heterocyclic ring system which may also contain oxygen, sulfur or an --NR 8 radical, R 8 is hydrogen, C 1 -C 4 alkyl or benzyl, and X is oxygen, sulfur, or a sulfinyl or sulfonyl bridge and to the salts thereof with amines, alkali metal bases or alkaline earth metal bases. These compounds have good pre- and postemergence selective herbicidal and growth regulating properties.

Inventors

  • 👤 Werner Fory
  • 👤 Karl Gass
  • 👤 Willy Meyer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 19:47
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/12; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/73; A; A01; A01N; A01N47/00; A01N47/08; A01N47/28; A01N47/36; C07D213/62; C07D213/70; C07D213/71; C07D213/74; C07D521/00

Claims Analysis

Total Claims: 22
Claim 1
Independent Claim 206 words
An N-pyridylsulfonyl-N'-triazinylurea of the formula ##STR21## wherein A is C 3 -C 6 alkynyl, C 1 -C 6 alkyl which is substituted by halogen or C 1 -C 4 alkoxy, C 2 -C 4 alkenyl which is unsubstituted or substituted by halogen or C 1 -C 4 alkoxy, or phenyl which is unsubstituted or substituted by halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or --X--C 1 -C 4 alkyl, R 1 is hydrogen, halogen or C 1 -C 4 alkyl, R 2 is C 1 -C 3 alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms, or is C 1 -C 3 alkoxy, R 3 is hydrogen, halogen, an amino group --NR 4 R 5 , or C 1 -C 3 alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms, or is C 1 -C 4 alkoxy which is unsubstituted or substituted by methoxy, ethoxy or 1 to 3 halogen atoms, R 4 is hydrogen or methyl, R 5 is hydrogen, C 1 -C 2 alkyl or methoxy, R 6 and R 7 are each independently hydrogen or C 3 -C 6 alkenyl, and X is oxygen, or a salt of such a compound.
Claim 2
Dependent Claim 206 words
An N-pyridylsulfonyl-N'-triazinylurea of the formula ##STR21## wherein A is C 3 -C 6 alkynyl, C 1 -C 6 alkyl which is substituted by halogen or C 1 -C 4 alkoxy, C 2 -C 4 alkenyl which is unsubstituted or substituted by halogen or C 1 -C 4 alkoxy, or phenyl which is unsubstituted or substituted by halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or --X--C 1 -C 4 alkyl, R 1 is hydrogen, halogen or C 1 -C 4 alkyl, R 2 is C 1 -C 3 alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms, or is C 1 -C 3 alkoxy, R 3 is hydrogen, halogen, an amino group --NR 4 R 5 , or C 1 -C 3 alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms, or is C 1 -C 4 alkoxy which is unsubstituted or substituted by methoxy, ethoxy or 1 to 3 halogen atoms, R 4 is hydrogen or methyl, R 5 is hydrogen, C 1 -C 2 alkyl or methoxy, R 6 and R 7 are each independently hydrogen or C 3 -C 6 alkenyl, and X is oxygen, or a salt of such a compound.
Claim 3
Dependent Claim 11 words
An N-pyridinylsulfonyl-N'-triazinylurea according to claim 1, wherein R 1 is hydrogen.
Claim 4
Dependent Claim 108 words
An N-pyridinylsulfonyl-N'-triazinylurea according to claim 1 wherein A is C 3 -C 4 alkoxyalkyl, C 3 -C 4 alkenyl or C 3 -C 4 alkynyl, R 1 is hydrogen, R 2 is C 2 -C 3 alkyl, which is unsubstituted or substituted by 1 to 3 halogen atoms or is C 1 -C 3 alkoxy and R 3 is hydrogen, halogen or an amino group --NR 4 R 5 , or C 1 -C 3 alkyl, which is unsubstituted or substituted by 1 to 3 halogen atoms, or is C 2 -C 4 alkoxy which is unsubstituted or substituted by methoxy, ethoxy or 1 to 3 halogen atoms.
Claim 5
Dependent Claim 24 words
An N-pyridylsulfonyl-N'-4-methoxy-6-methyltriazin-2-ylurea according to claim 3, of the formula ##STR22## wherein A" is C 3 -C 4 alkenyl or C 3 -C 4 alkoxyalkyl.
Claim 6
Dependent Claim 5 words
N-[2-(2-methoxyethoxy)-3-pyridylsulfonyl]-N'-[4-methoxy-6-methyl-1,3,5-triazinyl-2-yl]urea, according to claim 1.
Claim 7
Dependent Claim 5 words
N-[2-(2-methoxyethoxy)-3-pyridylsulfonyl]-N'-[4,6-dimethoxy)-1,3,5-triazinyl-2-yl]urea according to claim 1.
Claim 8
Dependent Claim 5 words
N-[2-(2-allyloxy-3-pyridylsulfonyl]-N'-[4-methoxy-6-methyl-1,3,5-triazin-2-yl]-urea according to claim 1.
Claim 9
Dependent Claim 5 words
N-[2-(2-propinyloxy-3-pyridylsulfonyl]-N'-[4-methoxy-6-methyl)-1,3,5-triazin-2-yl]-urea according to claim 1.
Claim 10
Dependent Claim 5 words
N-[2-(2-methallyloxy-3-pyridylsulfonyl]-N'-[4-methoxy-6-methyl-1,3,5-triazin-2-yl]urea according to claim 1.
Claim 11
Dependent Claim 5 words
N-[2-(2-but-2'-enyloxy-3-pyridylsulfonyl]-N'-[4-methoxy-6-methyl]-1,3,5-triazin-2-yl]urea according to claim 1.
Claim 12
Dependent Claim 5 words
N'-[2-(2-chloromethoxy-3-pyridylsulfonyl]-N'-[4-methoxy-6-methyl-1,3,5-triazin-2-yl]urea according to claim 1.
Claim 13
Dependent Claim 5 words
N'-[2-(2-amino-3-pyridylsulfonyl]-N'-[4-methoxy-6-methyl-1,3,5-triazin-2-yl]urea according to claim 1.
Claim 14
Dependent Claim 5 words
N-[2-(2-methylamino-3-pyridylsulfonyl]-N'-[4-methoxy-6-methyl-1,3,5-triazin-2-yl]urea according to claim 1.
Claim 15
Dependent Claim 5 words
N-[2-(2-dimethylamino-3-pyridylsulfonyl]-N'-[4-methoxy-6-methyl-1,3,5-triazin-2-yl]urea according to claim 1.
Claim 16
Dependent Claim 28 words
A herbicidal and plant growth regulating composition which contains an effective amount of an N-pyridylsulfonyl-N'-triazinylurea according to claim 1, together with an inert carrier and/or other inert adjuvants.
Claim 17
Dependent Claim 30 words
A method of inhibiting plant growth, which comprises applying to the plants an effective amount of an N-pyridylsulfonyl-N'-triazinylurea according to claim 1, or of a composition containing such a compound.
Claim 18
Dependent Claim 42 words
A method of selectively controlling weeds pre- or postemergence in crops of useful plants, which method comprises applying to the crops or crop area an effective amount of an N-pyridylsulfonyl-N'-triazinylurea according to claim 20, or of a composition containing such a compound.
Claim 19
Dependent Claim 18 words
A method according to claim 17, wherein said crops are sugar cane, cereals, maize, rice, soybeans or cotton.
Claim 20
Dependent Claim 39 words
A method of inhibiting the growth of cultivated plants to obtain an increase in yield, which comprises applying to the plants an effective amount of an N-pyridylsulfonyl-N'-triazinylurea according to claim 1, or of a composition containing such a compound.
Claim 21
Dependent Claim 12 words
A method according to claim 19, wherein said cultivated plants are soybeans.
Claim 22
Dependent Claim 13 words
A method according to claim 16, wherein said plants are cover crop leguminosae.

References Cited (Backward Citations)

US4435206A Cited
US4544401A Cited
EP0035893A2 Cited
US4456469A Cited
EP0044807A2 Cited
US4419121A Cited
US4425154A Cited
EP0056969A2 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-08-31 1991-03-02 1991-09-01 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-08-31 1995-03-02 1995-09-01 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-08-31 1999-03-02 1999-09-01 $7700.00 Window Closed / Lapsed

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