US4548639A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-Acyl-piperidone ketal compounds and their use as antidotes for protecting crop plants from herbicidal damage
Assignee: Bayer AG
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Filing: 1982-09-28
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Granted: 1985-10-22
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Expires: 2002-09-28
Abstract
Abstract N-Acyl-piperidone ketal compounds of the formula ##STR1## in which R 1 represents alkyl or halogen, R 2 represents halogen, R 3 represents alkyl and R 4 represents alkyl, or R 3 and R 4 together represent an optionally branched alkylene chain, and R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen or alkyl, and their use as antidotes for protecting crop plants from herbicidal damage.
Inventors
- 👤 Hans-Jochem Riebel
- 👤 Ludwig Eue
- 👤 Wilfried Faust
- 👤 Uwe Priesnitz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 20:46
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/32; C07D207/325; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D231/14; C07D231/16; C07D233/00; C07D233/54; C07D233/56; C07D233/66; C07D233/68; C07D249/00; C07D249/02; C07D249/08; C07D249/10; C07D249/12; C07D257/00; C07D257/02; C07D257/04; C07D271/00; C07D271/02; C07D271/10; C07D491/00; C07D491/02; C07D491/10
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
129 words
Method for the protection of crop plants from damage by herbicidally active acetanilides of the formula ##STR101## in which R is pyrazol-1-yl, X and Y are identical or different and represent alkyl with 1 to 4 carbon atoms, Z is chlorine and n represents 0 or 1, and herbicidally active acid-addition salts and metal salt complexes thereof, which method comprises applying to the plants or their habitat an antidotally effective amount of an N-acyl-piperidone ketal compound of the formula ##STR102## wherein R 1 is a alkyl with from 1 to 4 carbon atoms or chlorine; R 2 is chlorine; R 3 and R 4 together represent an alkylene chain of 2 to 3 carbon atoms; and R 5 , R 6 , R 7 and R 8 are hydrogen.
Claim 2
Dependent Claim
129 words
Method for the protection of crop plants from damage by herbicidally active acetanilides of the formula ##STR101## in which R is pyrazol-1-yl, X and Y are identical or different and represent alkyl with 1 to 4 carbon atoms, Z is chlorine and n represents 0 or 1, and herbicidally active acid-addition salts and metal salt complexes thereof, which method comprises applying to the plants or their habitat an antidotally effective amount of an N-acyl-piperidone ketal compound of the formula ##STR102## wherein R 1 is a alkyl with from 1 to 4 carbon atoms or chlorine; R 2 is chlorine; R 3 and R 4 together represent an alkylene chain of 2 to 3 carbon atoms; and R 5 , R 6 , R 7 and R 8 are hydrogen.
Claim 3
Dependent Claim
27 words
Method as claimed in claim 1 wherein said compound is applied to an area of agriculture in an amount of from 0.1 to 5 kg per hectare.
Claim 4
Dependent Claim
25 words
Method as claimed in claim 1 wherein said compound is applied to seed in an amount of 10 to 300 grams per kg of seed.
Claim 5
Dependent Claim
114 words
Herbicidal composition comprising a herbicidally active acetanilide of the formula ##STR103## in which R is pyrazol-1-yl, X and Y are identical or different and represent alkyl with 1 to 4 carbon atoms, Z is chlorine and n represents 0 or 1, and herbicidally active acid-addition salts and metal salt complexes thereof, and an antidotally effective amount of an N-acyl-piperidone ketal compound of the formula ##STR104## wherein R 1 is a alkyl with from 1 to 4 carbon atoms or chlorine; R 2 is chlorine; R 3 and R 4 together represent an alkylene chain of 2 to 3 carbon atoms; and R 5 , R 6 , R 7 and R 8 are hydrogen.
Claim 6
Dependent Claim
114 words
Herbicidal composition comprising a herbicidally active acetanilide of the formula ##STR103## in which R is pyrazol-1-yl, X and Y are identical or different and represent alkyl with 1 to 4 carbon atoms, Z is chlorine and n represents 0 or 1, and herbicidally active acid-addition salts and metal salt complexes thereof, and an antidotally effective amount of an N-acyl-piperidone ketal compound of the formula ##STR104## wherein R 1 is a alkyl with from 1 to 4 carbon atoms or chlorine; R 2 is chlorine; R 3 and R 4 together represent an alkylene chain of 2 to 3 carbon atoms; and R 5 , R 6 , R 7 and R 8 are hydrogen.
Claim 7
Dependent Claim
26 words
Herbicidal composition as claimed in claim 4 containing from 0.1 to 95% of a mixture consisting of the N-acyl-piperidone ketal compound and the herbicidally active acetanilide.
Claim 8
Dependent Claim
28 words
Herbicidal composition as claimed in claim 4 containing from 0.04 to 1 part by weight of said antidote compound per part by weight of said herbicidally active acetanilide.
Claim 9
Dependent Claim
28 words
Herbicidal composition as claimed in claim 4 containing from 0.1 to 0.5 part by weight of said antidote compound per part by weight of said herbicidally active acetanilide.
Claim 10
Dependent Claim
19 words
Method of combating weeds comprising applying to the weeds or their habitat a composition as claimed in claim 4.
Claim 11
Dependent Claim
27 words
Method as claimed in claim 8 wherein the composition is applied at a rate corresponding to 0.5 to 5 kg per hectare of said herbicidally active acetanilide.
Claim 12
Dependent Claim
94 words
Method for the protection of crop plants from damage by herbicidally active acetanilides of the formula ##STR105## in which R is pyrazol-1-yl, X and Y are identical or different and represent alkyl with 1 to 4 carbon atoms, Z is chlorine and n represents 0 or 1 and herbicidally active acid-addition salts and metal salt complexes thereof, which method comprises applying to the plants or their habitat an antidotally effective amount of an N-acyl-piperidone ketal compound selected from the group consisting of N-dichloroacetyl-piperid-4-one ethylene ketal; N-dichloroacetyl-piperid-4-one propylene ketal; N-α-chloropropionyl-piperid-4-one ethylene ketal; N-α-chloropropionyl-piperid-4-one propylene ketal.
Claim 13
Dependent Claim
94 words
Method for the protection of crop plants from damage by herbicidally active acetanilides of the formula ##STR105## in which R is pyrazol-1-yl, X and Y are identical or different and represent alkyl with 1 to 4 carbon atoms, Z is chlorine and n represents 0 or 1 and herbicidally active acid-addition salts and metal salt complexes thereof, which method comprises applying to the plants or their habitat an antidotally effective amount of an N-acyl-piperidone ketal compound selected from the group consisting of N-dichloroacetyl-piperid-4-one ethylene ketal; N-dichloroacetyl-piperid-4-one propylene ketal; N-α-chloropropionyl-piperid-4-one ethylene ketal; N-α-chloropropionyl-piperid-4-one propylene ketal.
Claim 14
Dependent Claim
80 words
An herbicidal composition comprising an herbicidally active acetanilide of the formula ##STR106## in which R is pyrazol-1-yl, X and Y are identical or different and represent alkyl with 1 to 4 carbon atoms, Z is chlorine and n represents 0 or 1, and herbicidally active acid-addition salts and metal salt complexes thereof, and an antidotally effective amount of an N-acyl-piperidone ketal compound selected from the group consisting of N-dichloroacetyl-piperid-4-one ethylene ketal; N-dichloroacetyl-piperid-4-one propylene ketal; N-α-chloropropionyl-piperid-4-one ethylene ketal; N-α-chloropropionyl-piperid-4-one propylene ketal.
Claim 15
Dependent Claim
80 words
An herbicidal composition comprising an herbicidally active acetanilide of the formula ##STR106## in which R is pyrazol-1-yl, X and Y are identical or different and represent alkyl with 1 to 4 carbon atoms, Z is chlorine and n represents 0 or 1, and herbicidally active acid-addition salts and metal salt complexes thereof, and an antidotally effective amount of an N-acyl-piperidone ketal compound selected from the group consisting of N-dichloroacetyl-piperid-4-one ethylene ketal; N-dichloroacetyl-piperid-4-one propylene ketal; N-α-chloropropionyl-piperid-4-one ethylene ketal; N-α-chloropropionyl-piperid-4-one propylene ketal.
Claim 16
Dependent Claim
92 words
Method of combating weeds comprising applying to the weeds or their habitat an herbicidal composition comprising an herbicidally active acetanilide of the formula ##STR107## in which R is pyrazol-1-yl, X and Y are identical or different and represent alkyl with 1 to 4 carbon atoms, Z is chlorine and n represents 0 or 1, and herbicidally active acid-addition salts and metal salt complexes thereof, and, an antidotally effective amount of an N-acyl-piperidone ketal compound selected from the group consisting of N-dichloroacetyl-piperid-4-one ethylene ketal; N-dichloroacetyl-piperid-4-one propylene ketal; N-α-chloropropionyl-piperid-4-one ethylene ketal; N-α-chloropropionyl-piperid-4-one propylene ketal.
Claim 17
Dependent Claim
92 words
Method of combating weeds comprising applying to the weeds or their habitat an herbicidal composition comprising an herbicidally active acetanilide of the formula ##STR107## in which R is pyrazol-1-yl, X and Y are identical or different and represent alkyl with 1 to 4 carbon atoms, Z is chlorine and n represents 0 or 1, and herbicidally active acid-addition salts and metal salt complexes thereof, and, an antidotally effective amount of an N-acyl-piperidone ketal compound selected from the group consisting of N-dichloroacetyl-piperid-4-one ethylene ketal; N-dichloroacetyl-piperid-4-one propylene ketal; N-α-chloropropionyl-piperid-4-one ethylene ketal; N-α-chloropropionyl-piperid-4-one propylene ketal.
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) | 1988-10-21 | 1989-04-22 | 1989-10-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-10-21 | 1993-04-22 | 1993-10-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-10-21 | 1997-04-22 | 1997-10-22 | $7700.00 | Window Closed / Lapsed |