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US4579583A Expired / Lapsed US ⏱️ 0.0 years remaining

Novel sulfonylureas

Assignee: Novartis Corp
•
Filing: 1983-08-29
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Granted: 1986-04-01
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Expires: 2003-08-29
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Abstract

Abstract The invention relates to N-pyridylsulfonyl-N'-pyrimidinyl- and -N'-triazinylureas of the formula I <IMAGE> (I) wherein A is a C3-C6alkynyl radical, a C1-C6alkyl radical which is substituted by halogen, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4haloalkoxy, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl or C1-C4haloalkylsulfonyl, or is a C2-C4alkenyl radical which is unsubstituted or substituted as for C1-C6alkyl, or is a phenyl radical which is unsubstituted or substituted by halogen, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, an -X-C1-C4-alkyl, C1-C4alkoxycarbonyl, amino, mono- or di-(C1-C4alkyl)amino, carbamoyl, mono- or di-(C1-C4alkyl)carbamoyl, sulfamoyl, mono- or di-(C1-C4alkyl)sulfamoyl radical or A-X- forms an amino radical -NR6R7, E is the methine group or nitrogen, R1 is hydrogen, halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, C2-C5alkoxyalkoxy, C1-C5alkylthio, C1-C5alkylsulfinyl or C1-C5alkylsulfonyl, R2 is C1-C3alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms, or is C1-C3alkoxy, R3 is hydrogen, halogen, an amino group -NR4R5, or C1-C3alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms, or is C1-C4alkoxy which is unsubstituted or substituted by methoxy, ethoxy or 1 to 3 halogen atoms, R4 is hydrogen or methyl, R5 is hydrogen, C1-C2alkyl or methoxy, R6 and R7 are each independently hydrogen, C1-C4alkyl, C3-C6alkenyl, C3-C6alkynyl, C3-C6alkoxyalkyl, C1-C4cyanoalkyl, 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 -NR8 radical, R8 is hydrogen, C1-C4alkyl 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 2026-10-29 11:58
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: 18
Claim 1
Independent Claim 283 words
An N-pyridylsulfonyl-N'-pyrimidinylurea of the formula ##STR21## wherein A is a C 3 -C 6 alkynyl radical, or a C 1 -C 6 alkyl radical which is substituted by halogen or C 1 -C 4 alkoxy, or A is a C 2 -C 4 alkenyl radical which is unsubstituted or substituted by halogen or C 1 -C 4 alkoxy, or A is a phenyl radical 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, or A--X-- forms an amino radical --NR 6 R 7 , 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, C 1 -C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, 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 or sulfur, or a salt thereof.
Claim 2
Dependent Claim 283 words
An N-pyridylsulfonyl-N'-pyrimidinylurea of the formula ##STR21## wherein A is a C 3 -C 6 alkynyl radical, or a C 1 -C 6 alkyl radical which is substituted by halogen or C 1 -C 4 alkoxy, or A is a C 2 -C 4 alkenyl radical which is unsubstituted or substituted by halogen or C 1 -C 4 alkoxy, or A is a phenyl radical 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, or A--X-- forms an amino radical --NR 6 R 7 , 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, C 1 -C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, 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 or sulfur, or a salt thereof.
Claim 3
Dependent Claim 11 words
An N-pyridylsulfonyl-N'-pyrimidinylurea according to claim 1, wherein R 1 is hydrogen.
Claim 4
Dependent Claim 29 words
An N-pyridylsulfonyl-N'-pyrimidinylurea according to claim 1, wherein R 1 is hydrogen, --X--A is in the 2-position and the --SO 2 -- group in the 3-position of the pyridyl ring.
Claim 5
Dependent Claim 25 words
An N-pyridylsulfonyl-N'-pyrimidinylurea according to claim 1, wherein A is C 3 -C 4 alkenyl or C 3 -C 4 alkynyl and R 1 is hydrogen.
Claim 6
Dependent Claim 28 words
A herbicidal and plant growth regulating composition which contains an effective amount of an N-pyridylsulfonyl-N'-pyrimidinylurea according to claim 1, together with an inert carrier and/or other inert adjuvants.
Claim 7
Dependent Claim 36 words
A method of controlling undesired plant growth, which comprises applying to the plants or area of undesired plant growth an effective amount of an N-pyridylsulfonyl-N'-pyrimidinylurea according to claim 1, or of a composition containing said compound.
Claim 8
Dependent Claim 29 words
A method of inhibiting plant growth, which comprises applying to the plants an effective amount of an N-pyridylsulfonyl-N'-pyrimidinylurea according to claim 1, or of a composition containing said compound.
Claim 9
Dependent Claim 45 words
A method according to claim 6 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'-pyrimidinylurea according to claim 1, or of a composition containing said compound.
Claim 10
Dependent Claim 39 words
A method according to claim 7 of inhibiting plant growth beyond the 2-leaf stage preemergence, which method comprises applying to the emerging plants an effective amount of an N-pyridylsulfonyl-N'-pyrimidinylurea according to claim 1, or a composition containing said compound.
Claim 11
Dependent Claim 18 words
A method according to claim 8, wherein said crops are sugar cane, cereals, maize, rice, soybeans or cotton.
Claim 12
Dependent Claim 38 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'-pyrimidinylurea according to claim 1, or of a composition containing said compound.
Claim 13
Dependent Claim 12 words
A method according to claim 11, wherein said cultivated plants are soybeans.
Claim 14
Dependent Claim 13 words
A method according to claim 7, wherein said plants are cover crop leguminosae.
Claim 15
Dependent Claim 5 words
N-[2-(2-methylallyloxy)-pyridin-3-ylsulfonyl]-N'-(4-methoxy-6-methylpyrimidin-2-yl)urea according to claim 6.
Claim 16
Dependent Claim 5 words
N-[2-(2-methylallyloxy)-pyridin-3-ylsulfonyl]-N'-(4-difluoromethoxy-6-methylpyrimidin-2-yl)urea according to claim 6.
Claim 17
Dependent Claim 5 words
N-[2-(2-butenyloxy)-pyridin-3-ylsulfonyl]-N'-(4,6-dimethylyrimidin-2-yl)urea according to claim 6.
Claim 18
Dependent Claim 10 words
An N-pyridylsulfonyl-N'-pyrimidinylurea according to claim 1 of the formula ##STR22##

References Cited (Backward Citations)

US4456469A Cited
US4419121A Cited
US4425154A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-03-31 1989-09-30 1990-04-01 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-03-31 1993-09-30 1994-04-01 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-03-31 1997-09-30 1998-04-01 $7700.00 Window Closed / Lapsed

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