Patent US4349378A successfully refreshed from Google Patents.
US4349378A
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US
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Compounds useful as pesticides
Assignee: Bayer CropScience Ltd
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Filing: 1978-12-14
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Granted: 1982-09-14
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Expires: 1998-12-14
Abstract
Abstract Sulphonanilides of formula <IMAGE> I and salts thereof, wherein R1 represents alkyl or certain other groups; R represents alkylene or alkenylene; A represents -COR12 or a carbonyl derivative or addition compound thereof, where R12 represents hydrogen, alkyl or certain other groups; and R2-R6 represent hydrogen, alkyl, halogen or certain other groups; are pesticides and plant growth regulants, especially herbicides and fungicides.
Inventors
- 👤 Geoffrey R. Cliff
- 👤 Russell G. Hunt
- 👤 Albert Percival
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:54
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/16; C07D295/18; C07D295/182; C07D295/185; A; A01; A01N; A01N41/00; A01N41/02; A01N41/04; A01N41/06; A01N41/08; A01N43/00; A01N43/02; A01N43/04; A01N43/06; A01N43/08; A01N43/10; A01N43/24; A01N43/26; A01N43/28; A01N43/48; A01N43/56; A01N47/00; A01N47/08; A01N47/10; A01N47/24; A01N47/40; A01N47/48; C07D295/04; C07D295/10; C07D295/104; C07D295/108; C07D295/22; C07D295/26; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/40; C07D307/42; C07D317/00; C07D317/08; C07D317/10; C07D317/32; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/30; C07D333/34; C07D339/00; C07D339/02; C07D339/06
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
253 words
A compound which is a sulphonanilide of formula ##STR93## or salt thereof, wherein R 1 represents alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen, alkoxy of 1-6 carbon atoms, hydroxy, amino and amino mono- or di-substituted by roups selected from alkyl of 1-15 carbon atoms; cycloalkyl of 3-7 carbon atoms; phenyl; phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms and nitro; or a group of formula ##STR94## where R 7 and R 8 are the same or different and each represents a hydrogen atom, alkyl of 1-15 carbon atoms, phenyl, or phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms, nitro and trifluoromethyl; R represents alkylene of 1-6 carbon atoms; A represents --COR 12 where R 12 represents lower alkyl or lower alkyl substituted by one or more of halogen, hydroxy alkoxy of 1-6 carbon atoms; and R 2 , R 3 , R 4 , R 5 and R 6 are the same or different and each represents a hydrogen atom; alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen and alkoxy of 1-6 carbon atoms; hydroxy; alkoxy of 1-6 carbon atoms; nitro; a halogen atom; amino; a group of formula --SR 16 or --SO 2 R 16 where R 16 represents alkyl of 1-6 carbon atoms or phenyl; or --SO 2 NR 7 R 8 where R 7 and R 8 are as defined above.
Claim 2
Dependent Claim
253 words
A compound which is a sulphonanilide of formula ##STR93## or salt thereof, wherein R 1 represents alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen, alkoxy of 1-6 carbon atoms, hydroxy, amino and amino mono- or di-substituted by roups selected from alkyl of 1-15 carbon atoms; cycloalkyl of 3-7 carbon atoms; phenyl; phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms and nitro; or a group of formula ##STR94## where R 7 and R 8 are the same or different and each represents a hydrogen atom, alkyl of 1-15 carbon atoms, phenyl, or phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms, nitro and trifluoromethyl; R represents alkylene of 1-6 carbon atoms; A represents --COR 12 where R 12 represents lower alkyl or lower alkyl substituted by one or more of halogen, hydroxy alkoxy of 1-6 carbon atoms; and R 2 , R 3 , R 4 , R 5 and R 6 are the same or different and each represents a hydrogen atom; alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen and alkoxy of 1-6 carbon atoms; hydroxy; alkoxy of 1-6 carbon atoms; nitro; a halogen atom; amino; a group of formula --SR 16 or --SO 2 R 16 where R 16 represents alkyl of 1-6 carbon atoms or phenyl; or --SO 2 NR 7 R 8 where R 7 and R 8 are as defined above.
Claim 3
Dependent Claim
100 words
A compound as defined in claim 1 wherein R 1 represents alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen, alkoxy of 1-6 carbon atoms, hydroxy, amino and amino mono- or di-substituted by groups selected from alkyl of 1-15 carbon atoms; cycloalkyl of 3-7 carbon atoms; or a group of formula ##STR95## where R 7 and R 8 are the same or different and each represents a hydrogen atom, alkyl of 1-15 carbon atoms, phenyl, or phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms, nitro and trifluoromethyl.
Claim 4
Dependent Claim
92 words
A compound as defined in claim 1 wherein R 1 represents alkyl of 1-4 carbon atoms, nitrophenyl, or dialkylamino of 2-8 carbon atoms; R represents alkylene of 1-3 carbon atoms; A represents --COCH 3 ; --COCH 2 OH; --COC(CH.sub.3).sub.3 ; and 3 or 4 of R 2 , R 3 , R 4 , R 5 and R 6 each represent a hydrogen atom and the remainder are the same or different and each represents alkyl of 1-3 carbon atoms, halogen, hydroxy, phenylmercapto, nitro, alkoxy of 1-6 carbon atoms, trifluoromethyl or phenylsulphonyl.
Claim 5
Dependent Claim
225 words
A compound as defined in claim 1 wherein R 1 represents alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen, alkoxy of 1-6 carbon atoms, amino and amino mono- or di-substituted by groups selected from alkyl of 1-15 carbon atoms; cycloalkyl of 3-7 carbon atoms; phenyl; phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms and nitro; or a group of formula ##STR96## where R 7 and R 8 are the same or different and each represents a hydrogen atom; alkyl of 1-15 carbon atoms; phenyl; or phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms, nitro and trifluoromethyl; R 12 represents lower alkyl; or lower alkyl substituted by one or more of halogen, alkoxy of 1-6 carbon atoms; and R 2 , R 3 , R 4 , R 5 and R 6 are the same or different and each represents a hydrogen atom; alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen and alkoxy of 1-6 carbon atoms; alkoxy of 1-6 carbon atoms; nitro; a halogen atom; amino; or a group of formula --SR 16 or --SO 2 R 16 where R 16 represents alkyl of 1-6 carbon atoms or phenyl and wherein R 6 represents other than hydrogen.
Claim 6
Dependent Claim
1 words
N-2-oxo-propyl-2',6'-dimethyl-methanesulphonaniline.
Claim 7
Dependent Claim
1 words
N-2-oxo-propyl-2',6'-dimethyl-methanesulphonaniline.
Claim 8
Dependent Claim
278 words
A pesticidal or plant growth regulant composition comprising an effective amount of a compound which is a sulphonanilide of formula ##STR97## or salt thereof, wherein R 1 represents alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen, alkoxy of 1-6 carbon atoms, hydroxy, amino and amino mono- or di-substituted by groups selected from alkyl of 1-15 carbon atoms; cycloalkyl of 3-7 carbon atoms; phenyl; phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms and nitro; or a group of formula ##STR98## where R 7 and R 8 are the same or different and each represents a hydrogen atom, alkyl of 1-15 carbon atoms, phenyl, or phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms, nitro and trifluoromethyl; R represents alkylene of 1-6 carbon atoms; A represents --COR 12 wherein R 12 represents lower alkyl or lower alkyl substituted by one or more of halogen, hydroxy alkoxy of 1-6 carbon atoms; and R 2 , R 3 , R 4 , R 5 and R 6 are the same or different and each represents a hydrogen atom; alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen and alkoxy of 1-6 carbon atoms; hydroxy; alkoxy of 1-6 carbon atoms; nitro; a halogen atom; amino; a group of formula --SR 16 or --SO 2 R 16 where R 16 represents alkyl of 1-6 carbon atoms or phenyl; or --SO 2 NR 7 R 8 where R 7 and R 8 are as defined above together with at least one material selected from carriers and surface active agents.
Claim 9
Dependent Claim
278 words
A pesticidal or plant growth regulant composition comprising an effective amount of a compound which is a sulphonanilide of formula ##STR97## or salt thereof, wherein R 1 represents alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen, alkoxy of 1-6 carbon atoms, hydroxy, amino and amino mono- or di-substituted by groups selected from alkyl of 1-15 carbon atoms; cycloalkyl of 3-7 carbon atoms; phenyl; phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms and nitro; or a group of formula ##STR98## where R 7 and R 8 are the same or different and each represents a hydrogen atom, alkyl of 1-15 carbon atoms, phenyl, or phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms, nitro and trifluoromethyl; R represents alkylene of 1-6 carbon atoms; A represents --COR 12 wherein R 12 represents lower alkyl or lower alkyl substituted by one or more of halogen, hydroxy alkoxy of 1-6 carbon atoms; and R 2 , R 3 , R 4 , R 5 and R 6 are the same or different and each represents a hydrogen atom; alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen and alkoxy of 1-6 carbon atoms; hydroxy; alkoxy of 1-6 carbon atoms; nitro; a halogen atom; amino; a group of formula --SR 16 or --SO 2 R 16 where R 16 represents alkyl of 1-6 carbon atoms or phenyl; or --SO 2 NR 7 R 8 where R 7 and R 8 are as defined above together with at least one material selected from carriers and surface active agents.
Claim 10
Dependent Claim
104 words
A composition according to claim 6 wherein the compound is one wherein R 1 represents alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen, alkoxy of 1-6 carbon atoms, hydroxy, amino and amino mono- or di-substituted by groups selected from alkyl of 1-15 carbon atoms; cycloalkyl of 3-7 carbon atoms; or a group of formula ##STR99## where R 7 and R 8 are the same or different and each represents a hydrogen atom, alkyl of 1-15 carbon atoms, phenyl, or phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms, nitro and trifluoromethyl.
Claim 11
Dependent Claim
95 words
A composition according to claim 6 wherein the compound is one wherein R 1 represents alkyl of 1-4 carbon atoms, nitrophenyl, or dialkylamino of 2-8 carbon atoms; R represents alkylene of 1-3 carbon atoms; A represents --COCH 3 ; --COCH 2 OH; --COC(CH.sub.3).sub.3 ; 3 or 4 of R 2 , R 3 , R 4 , R 5 and R 6 each represent a hydrogen atom and the remainder are the same or different and each represents alkyl of 1-3 carbon atoms, halogen, hydroxy, phenylmercapto, nitro, alkoxy of 1-6 carbon atoms, trifluoromethyl or phenylsulphonyl.
Claim 12
Dependent Claim
229 words
A composition according to claim 6 wherein the compound is one wherein R 1 represents alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen, alkoxy of 1-6 carbon atoms, amino and amino mono- or di-substituted by groups selected from alkyl of 1-15 carbon atoms; cycloalkyl of 3-7 carbon atoms; phenyl; phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms and nitro; or a group of formula ##STR100## where R 7 and R 8 are the same or different and each represents a hydrogen atom; alkyl of 1-15 carbon atoms; phenyl; or phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms, nitro and trifluoromethyl; R 12 represents lower alkyl; or lower alkyl substituted by one or more of halogen, alkoxy of 1-6 carbon atoms; and R 2 , R 3 , R 4 , R 5 and R 6 are the same or different and each represents a hydrogen atom; alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen and alkoxy of 1-6 carbon atoms; alkoxy of 1-6 carbon atoms; nitro; a halogen atom; amino; or a group of formula --SR 16 or --SO 2 R 16 where R 16 represents alkyl of 1-6 carbon atoms or phenyl and wherein R 6 represents other than hydrogen.
Claim 13
Dependent Claim
11 words
A composition according to claim 6 wherein the compound is N-2-oxopropyl-2',6'-dimethyl-methanesulphonanilide.
Claim 14
Dependent Claim
13 words
A composition as claimed in claim 6 which contains a surface active agent.
Claim 15
Independent Claim
308 words
A method of combatting pests at a locus infested or liable to be infested with them or of regulating the growth of a plant at a locus at which the plant is growing or is to grow, which method comprises the step of applying to the locus a pest-combatting or plant growth regulant amount of a compound which is a sulphonanilide of formula: ##STR101## or salt thereof, wherein R 1 represents alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen, alkoxy of 1-6 carbon atoms, hydroxy, amino and amino mono- or di-substituted by groups selected from alkyl of 1-15 carbon atoms; cycloalkyl of 3-7 carbon atoms; phenyl; phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms and nitro; or a group of formula ##STR102## wherein R 7 and R 8 are the same or different and each represents a hydrogen atom, alkyl of 1-15 carbon atoms, phenyl, or phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms, nitro and trifluoromethyl; R represents alkylene of 1-6 carbon atoms; A represents --COR 12 where R 12 represents lower alkyl or lower alkyl substituted by one or more of halogen, hydroxy alkoxy of 1-6 carbon atoms; and R 2 , R 3 , R 4 , R 5 and R 6 are the same or different and each represents a hydrogen atom; alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen and alkoxy of 1-6 carbon atoms; hydroxy; alkoxy of 1-6 carbon atoms; nitro; a halogen atom; amino; a group of formula --SR 16 or --SO 2 R 16 where R 16 represents alkyl of 1-6 carbon atoms or phenyl; or --SO 2 NR 7 R 8 where R 7 and R 8 are as defined above.
Claim 16
Independent Claim
308 words
A method of combatting pests at a locus infested or liable to be infested with them or of regulating the growth of a plant at a locus at which the plant is growing or is to grow, which method comprises the step of applying to the locus a pest-combatting or plant growth regulant amount of a compound which is a sulphonanilide of formula: ##STR101## or salt thereof, wherein R 1 represents alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen, alkoxy of 1-6 carbon atoms, hydroxy, amino and amino mono- or di-substituted by groups selected from alkyl of 1-15 carbon atoms; cycloalkyl of 3-7 carbon atoms; phenyl; phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms and nitro; or a group of formula ##STR102## wherein R 7 and R 8 are the same or different and each represents a hydrogen atom, alkyl of 1-15 carbon atoms, phenyl, or phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms, nitro and trifluoromethyl; R represents alkylene of 1-6 carbon atoms; A represents --COR 12 where R 12 represents lower alkyl or lower alkyl substituted by one or more of halogen, hydroxy alkoxy of 1-6 carbon atoms; and R 2 , R 3 , R 4 , R 5 and R 6 are the same or different and each represents a hydrogen atom; alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen and alkoxy of 1-6 carbon atoms; hydroxy; alkoxy of 1-6 carbon atoms; nitro; a halogen atom; amino; a group of formula --SR 16 or --SO 2 R 16 where R 16 represents alkyl of 1-6 carbon atoms or phenyl; or --SO 2 NR 7 R 8 where R 7 and R 8 are as defined above.
Claim 17
Dependent Claim
99 words
A method according to claim 12 wherein R 1 represents alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen, alkoxy of 1-6 carbon atoms, hydroxy, amino and amino mono- or di-substituted by groups selected from alkyl of 1-15 carbon atoms; cycloalkyl of 3-7 carbon atoms; or a group of formula ##STR103## where R 7 and R 8 are the same or different and each represents a hydrogen atom, alkyl of 1-15 carbon atoms, phenyl, or phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms, nitro and trifluoromethyl.
Claim 18
Dependent Claim
216 words
A method according to claim 12 wherein R 1 represents alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen, alkoxy of 1-6 carbon atoms, amino and amino mono- or di-substituted by groups selected from alkyl of 1-15 carbon atoms; cycloalkyl of 3-7 carbon atoms; phenyl; phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms and nitro; or a group of formula ##STR104## where R 7 and R 8 are the same or different and each represents a hydrogen atom; alkyl of 1-15 carbon atoms; phenyl; or phenyl substituted by one or more of halogen, alkyl of 1-6 carbon atoms, nitro and trifluoromethyl; R 12 represents lower alkyl; or lower alkyl substituted by one or more of halogen, alkoxy of 1-6 carbon atoms; and R 2 , R 3 , R 4 , R 5 and R 6 are the same or different and each represents a hydrogen atom; alkyl of 1-15 carbon atoms; alkyl of 1-15 carbon atoms substituted by one or more of halogen and alkoxy of 1-6 carbon atoms; alkoxy of 1-6 carbon atoms; nitro; a halogen atom; amino; or a group of formula --SR 16 or --SO 2 R 16 where R 16 represents alkyl of 1-6 carbon atoms or phenyl.
Claim 19
Dependent Claim
30 words
A method according to claim 12 wherein 3 or 4 of R 2 , R 3 , R 4 , R 5 and R 6 each represent a hydrogen atom.
Claim 20
Dependent Claim
90 words
A method according to claim 12 wherein R 1 represents alkyl of 1-4 carbon atoms, nitrophenyl, or dialkylamino of 2-8 carbon atoms; R represents alkylene of 1-3 carbon atoms; A represents --COCH 3 ; --COCH 2 OH; --COC(CH.sub.3).sub.3 ; 3 or 4 of R 2 , R 3 , R 4 , R 5 and R 6 each represent a hydrogen atom and the remainder are the same or different and each represents alkyl of 1-3 carbon atoms, halogen, hydroxy, phenylmercapto, nitro, alkoxy of 1-6 carbon atoms, trifluoromethyl or phenylsulphonyl.
Claim 21
Dependent Claim
11 words
A method according to claim 12 wherein the compound is N-2-oxopropyl-2',6'-dimethyl-methanesulphonanilide.
Claim 22
Dependent Claim
24 words
A method according to claim 12 wherein the compound is applied to a locus at which a crop is growing or is to grow.
Claim 23
Dependent Claim
21 words
A method according to claim 12 wherein 0.5-10 kg of the compound are applied per hectare and weeds are selectively combated.
Claim 24
Dependent Claim
20 words
A method according to claim 12 wherein 1-6 kg of the compound are applied per hectare and fungus is combated.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-09-13 | 1986-03-15 | 1986-09-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-09-13 | 1990-03-15 | 1990-09-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-09-13 | 1994-03-15 | 1994-09-14 | $7700.00 | Window Closed / Lapsed |