Patent US4421550A successfully refreshed from Google Patents.
US4421550A
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Herbicidal triazole ureas
Assignee: EIDP Inc
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Filing: 1982-05-28
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Granted: 1983-12-20
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Expires: 2002-05-28
Abstract
Abstract Triazole ureas demonstrate utility as agricultural chemicals and in particular as herbicides.
Inventors
- 👤 Thomas P. Selby
- 👤 Anthony D. Wolf
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 22:56
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/88; A; A01; A01N; A01N47/00; A01N47/08; A01N47/28; A01N47/36; C07D249/00; C07D249/02; C07D249/08; C07D249/10; C07D249/14
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
913 words
A compound of the formula: ##STR145## wherein R 1 is H, C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, SR 4 , OR 5 , CH 2 OR 6 , CH 2 CH 2 OR 6 , CF 3 , CF 2 CF 3 , Cl, NHCH 3 , N(CH 3 ) 2 , CH(OCH 3 ) 2 or ##STR146## R 2 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, CH 2 OCH 3 , CH 2 CH 2 OCH 3 , CH 2 SCH 3 , CH 2 CH 2 SCH 3 or C 1 -C 4 alkyl substituted with 1-3 F atoms; R 3 is H or CH 3 ; R 4 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, CH 2 CO 2 R 6 or CH(CH 3 )CO 2 R 6 ; R 5 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, CH 2 CO 2 R 6 , CH(CH 3 )CO 2 R 6 or CH 2 CF 3 ; R 6 is C 1 -C 4 alkyl; W is O or S; Z is ##STR147## R 7 is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, F, C(O)NR 21 R 22 , Cl, Br, NO 2 , CF 3 , CO 2 R 9 , SO 2 NR 10 R 11 , C(O)SR 10 , SO 2 N(OCH 3 )CH 3 , QSO 2 R 12 , S(O) n R 13 , CH 2 CO 2 R 20 , CH(CH 3 )CO 2 R 20 , CH 2 S(O) n R 13 , CH(CH 3 )S(O) n R 13 , C 13 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 1 -C 2 alkyl substituted with either OCH 3 or OC 2 H 5 , or C 1 -C 3 alkoxy substituted with either (a) 1-5 atoms of Cl, Br or F or (b) OCH 3 or OC 2 H 5 ; R 8 is H, F, Cl, Br, CF 3 , NO 2 , C 1 -C 3 alkyl or C 1 -C 3 alkoxy; R 9 is C 1 -C 6 alkyl, CH 2 CH 2 OCH 3 , CH 2 CH 2 OCH 2 CH 3 , CH 2 CH 2 CH 2 OCH 2 CH 3 , C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or C 1 -C 3 alkyl substituted with 1-3 atoms of Cl or F; R 10 and R 11 are independently C 1 -C 3 alkyl; R 12 is C 1 -C 4 alkyl, CH 2 CH 2 OCH 3 , CH 2 CH 2 CH 2 OCH 3 or C 1 -C 4 alkyl substituted with 1-3 atoms of F, Cl or Br; R 13 is C 1 -C 4 alkyl, allyl, C 1 -C 3 alkyl substituted with 1-5 atoms of F, Cl or Br; n is 0, 1 or 2; Q is O or NCH 3 ; R 14 is H, CH 3 , OCH 3 , F, Cl, Br, NO 2 , SO 2 NR 10 R 11 , SO 2 N(OCH 3 )CH 3 , OSO 2 R 12 or S(O) n R 13 ; R 15 is H, Cl, Br, CH 3 , OCH 3 or NO 2 ; R 16 is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, F, Cl, Br, CF 3 , CO 2 R 20 , SO 2 NR 10 R 11 , SO 2 N(OCH 3 )CH 3 or S(O) n R 13 ; R 17 is H, F, Cl, Br, CH 3 or OCH 3 ; W' is O or S; R 18 is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, F, Cl, Br, NO 2 , CO 2 R 20 , SO 2 NR 10 R 11 , SO 2 N(OCH 3 )CH 3 or S(O) n R 13 ; R 19 is Cl, NO 2 , CF 3 , CO 2 R 9 , SO 2 N(OCH 3 )CH 3 , SO 2 NR 10 R 11 , QSO 2 R 12 , S(O) n R 13 or C 1 -C 3 alkoxy substituted with 1-5 atoms of Cl or F; R 20 is C 1 -C 4 alkyl, CH 2 CH 2 OCH 3 , CH 2 CH 2 Cl or CH 2 CH═CH 2 ; R 21 is C 1 -C 3 alkyl or C 6 H 5 ; R 22 is C 1 -C 3 alkyl; and R 21 and R 22 may be taken together to be ##STR148## provided that (1) the total number of carbon atoms of R 10 and R 11 is less than or equal to 4; (2) the total number of carbon atoms of R 1 and R 2 is less than or equal to 6; (3) when W' is O, then R 18 is H, Cl, Br, CH 3 or CO 2 R 20 ; (4) when W' is O and R 18 is H, Cl, Br or CH 3 , then Z is ##STR149## (5) when W is S, then R 3 is H; (6) when R 7 is H, then R 8 is H; and (7) R 14 and R 15 may not both be NO 2 .
Claim 2
Dependent Claim
913 words
A compound of the formula: ##STR145## wherein R 1 is H, C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, SR 4 , OR 5 , CH 2 OR 6 , CH 2 CH 2 OR 6 , CF 3 , CF 2 CF 3 , Cl, NHCH 3 , N(CH 3 ) 2 , CH(OCH 3 ) 2 or ##STR146## R 2 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, CH 2 OCH 3 , CH 2 CH 2 OCH 3 , CH 2 SCH 3 , CH 2 CH 2 SCH 3 or C 1 -C 4 alkyl substituted with 1-3 F atoms; R 3 is H or CH 3 ; R 4 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, CH 2 CO 2 R 6 or CH(CH 3 )CO 2 R 6 ; R 5 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, CH 2 CO 2 R 6 , CH(CH 3 )CO 2 R 6 or CH 2 CF 3 ; R 6 is C 1 -C 4 alkyl; W is O or S; Z is ##STR147## R 7 is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, F, C(O)NR 21 R 22 , Cl, Br, NO 2 , CF 3 , CO 2 R 9 , SO 2 NR 10 R 11 , C(O)SR 10 , SO 2 N(OCH 3 )CH 3 , QSO 2 R 12 , S(O) n R 13 , CH 2 CO 2 R 20 , CH(CH 3 )CO 2 R 20 , CH 2 S(O) n R 13 , CH(CH 3 )S(O) n R 13 , C 13 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 1 -C 2 alkyl substituted with either OCH 3 or OC 2 H 5 , or C 1 -C 3 alkoxy substituted with either (a) 1-5 atoms of Cl, Br or F or (b) OCH 3 or OC 2 H 5 ; R 8 is H, F, Cl, Br, CF 3 , NO 2 , C 1 -C 3 alkyl or C 1 -C 3 alkoxy; R 9 is C 1 -C 6 alkyl, CH 2 CH 2 OCH 3 , CH 2 CH 2 OCH 2 CH 3 , CH 2 CH 2 CH 2 OCH 2 CH 3 , C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or C 1 -C 3 alkyl substituted with 1-3 atoms of Cl or F; R 10 and R 11 are independently C 1 -C 3 alkyl; R 12 is C 1 -C 4 alkyl, CH 2 CH 2 OCH 3 , CH 2 CH 2 CH 2 OCH 3 or C 1 -C 4 alkyl substituted with 1-3 atoms of F, Cl or Br; R 13 is C 1 -C 4 alkyl, allyl, C 1 -C 3 alkyl substituted with 1-5 atoms of F, Cl or Br; n is 0, 1 or 2; Q is O or NCH 3 ; R 14 is H, CH 3 , OCH 3 , F, Cl, Br, NO 2 , SO 2 NR 10 R 11 , SO 2 N(OCH 3 )CH 3 , OSO 2 R 12 or S(O) n R 13 ; R 15 is H, Cl, Br, CH 3 , OCH 3 or NO 2 ; R 16 is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, F, Cl, Br, CF 3 , CO 2 R 20 , SO 2 NR 10 R 11 , SO 2 N(OCH 3 )CH 3 or S(O) n R 13 ; R 17 is H, F, Cl, Br, CH 3 or OCH 3 ; W' is O or S; R 18 is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, F, Cl, Br, NO 2 , CO 2 R 20 , SO 2 NR 10 R 11 , SO 2 N(OCH 3 )CH 3 or S(O) n R 13 ; R 19 is Cl, NO 2 , CF 3 , CO 2 R 9 , SO 2 N(OCH 3 )CH 3 , SO 2 NR 10 R 11 , QSO 2 R 12 , S(O) n R 13 or C 1 -C 3 alkoxy substituted with 1-5 atoms of Cl or F; R 20 is C 1 -C 4 alkyl, CH 2 CH 2 OCH 3 , CH 2 CH 2 Cl or CH 2 CH═CH 2 ; R 21 is C 1 -C 3 alkyl or C 6 H 5 ; R 22 is C 1 -C 3 alkyl; and R 21 and R 22 may be taken together to be ##STR148## provided that (1) the total number of carbon atoms of R 10 and R 11 is less than or equal to 4; (2) the total number of carbon atoms of R 1 and R 2 is less than or equal to 6; (3) when W' is O, then R 18 is H, Cl, Br, CH 3 or CO 2 R 20 ; (4) when W' is O and R 18 is H, Cl, Br or CH 3 , then Z is ##STR149## (5) when W is S, then R 3 is H; (6) when R 7 is H, then R 8 is H; and (7) R 14 and R 15 may not both be NO 2 .
Claim 3
Dependent Claim
13 words
Compounds of claim 1 wherein W is O and R 3 is H.
Claim 4
Dependent Claim
39 words
Compounds of claim 2 where Z is ##STR150## W' is S; R 19 is CO 2 CH 3 , SO 2 N(CH 3 ) 2 or SO 2 CH 3 ; and R 15 and R 17 are H.
Claim 5
Dependent Claim
8 words
Compounds of claim 3 where Z is ##STR151##
Claim 6
Dependent Claim
67 words
Compounds of claim 4 where R 1 is C 1 -C 2 alkyl, CH 2 CF 3 , SR 4 , OR 5 , CH 2 OCH 3 , N(CH 3 ) 2 or Cl; R 2 is C 1 -C 2 alkyl, CH 2 CH═CH 2 or CH 2 C═CH; and R 4 and R 5 are independently CH 3 or C 2 H 5 .
Claim 7
Dependent Claim
31 words
Compounds of claim 5 where Z is ##STR152## R 7 is other than H; and R 8 is H, F, Cl, Br, CF 3 , CH 3 or OCH 3 .
Claim 8
Dependent Claim
83 words
Compounds of claim 6 where R 7 is Cl, NO 2 , CO 2 R 9 , SO 2 NR 10 R 11 or OSO 2 R 12 ; R 8 is H; R 9 is C 1 -C 3 alkyl, CH 2 CH═CH 2 , CH 2 CH 2 OCH 3 or CH 2 CH 2 Cl; R 10 and R 11 are independently C 1 -C 2 alkyl; and R 12 and R 13 are independently C 1 -C 3 alkyl.
Claim 9
Dependent Claim
23 words
Compounds of claim 7 where R 9 , R 10 , R 11 , R 12 and R 13 are CH 3 .
Claim 10
Dependent Claim
9 words
The compound of claim 1, 2-[[(5-methylthio-1-methyl-1H-1,2,4-triazol-3-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester.
Claim 11
Dependent Claim
9 words
The compound of claim 1, 2-[[(5-ethylthio-1-methyl-1H-1,2,4-triazol-3-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester.
Claim 12
Dependent Claim
9 words
The compound of claim 1, 2-[[(5-ethyl-1-methyl-1H-1,2,4-triazol-3-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester.
Claim 13
Dependent Claim
9 words
The compound of claim 1, 2-[[(5-methoxy-1-methyl-1H-1,2,4-triazol-3-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester.
Claim 14
Dependent Claim
6 words
The compound of claim 1, N-[(5-methoxy-1-methyl-1H-1,2,4-triazol-3-yl)aminocarbonyl]-2-chlorobenzenesulfonamide.
Claim 15
Dependent Claim
6 words
The compound of claim 1, N-[(5-methoxy-1-methyl-1H-1,2,4-triazol-3-yl)aminocarbonyl]-N',N'-dimethyl-1,2-benzenedisulfonamide.
Claim 16
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
Claim 17
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
Claim 18
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
Claim 19
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
Claim 20
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.
Claim 21
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid diluent.
Claim 22
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid or liquid diluent.
Claim 23
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 8 and at least one of the following: surfactant, solid or liquid diluent.
Claim 24
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 9 and at least one of the following: surfactant, solid or liquid diluent.
Claim 25
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 10 and at least one of the following: surfactant, solid or liquid diluent.
Claim 26
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 11 and at least one of the following: surfactant, solid or liquid diluent.
Claim 27
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 12 and at least one of the following: surfactant, solid or liquid diluent.
Claim 28
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 13 and at least one of the following: surfactant, solid or liquid diluent.
Claim 29
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 14 and at least one of the following: surfactant, solid or liquid diluent.
Claim 30
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 1.
Claim 31
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 2.
Claim 32
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 3.
Claim 33
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 4.
Claim 34
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 5.
Claim 35
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 6.
Claim 36
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 7.
Claim 37
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 8.
Claim 38
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim 9.
Claim 39
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim 10.
Claim 40
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim 11.
Claim 41
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim 12.
Claim 42
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim 13.
Claim 43
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim 14.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-12-19 | 1987-06-20 | 1987-12-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-12-19 | 1991-06-20 | 1991-12-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-12-19 | 1995-06-20 | 1995-12-20 | $7700.00 | Window Closed / Lapsed |