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US4225334A
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Phenylglyoxylonitrile-2-oxime-cyanomethyl ether as a crop safener
Assignee: Novartis Corp
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Filing: 1979-03-26
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Granted: 1980-09-30
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Expires: 1999-03-26
Abstract
Abstract The new compound phenylglyoxylonitrile-2-oxime-cyanomethylether of the formula ##STR1## and compositions containing it, are used as a safener (antidote) for selectively combatting weeds in culture crops, especially sorghum and rice, in order to protect these cultivated plants from being injured by strong herbicides such as chloroacetanilides and thiolcarbamates. The safener is preferably applied to the crop seeds prior to planting.
Inventors
- 👤 Henry Martin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 20:18
CPC Classifications
C; C03; C03C; C03C27/00; A; A01; A01N; A01N37/00; A01N37/44; A01N37/50; C03C8/00; C03C8/24; C07; C07C; C07C255/00; C07C255/63; C07C255/64
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
79 words
A herbicidal composition comprising (1) a herbicidally effective amount of a chloroacetanilide compound of the formula ##STR8## wherein R 1 is lower alkyl, lower alkoxy, lower alkoxyalkyl, fluorine or chlorine and R 2 , R 4 and R 5 independently of one another are hydrogen, lower alkyl, lower alkoxy, lower alkoxyalkyl or chlorine and R is 1,3-dioxolan-2-yl-alkyl, 1,3-dioxolan-5-yl-alkyl, 1,3-dioxan-2-yl-alkyl, furanylmethyl or tetrahydrofuranylmethyl and (2) phenylglyoxylonitrile-2-oxime-cyanomethyl ether in sufficient amount to prevent injury to crops treated with said herbicide composition.
Claim 2
Dependent Claim
79 words
A herbicidal composition comprising (1) a herbicidally effective amount of a chloroacetanilide compound of the formula ##STR8## wherein R 1 is lower alkyl, lower alkoxy, lower alkoxyalkyl, fluorine or chlorine and R 2 , R 4 and R 5 independently of one another are hydrogen, lower alkyl, lower alkoxy, lower alkoxyalkyl or chlorine and R is 1,3-dioxolan-2-yl-alkyl, 1,3-dioxolan-5-yl-alkyl, 1,3-dioxan-2-yl-alkyl, furanylmethyl or tetrahydrofuranylmethyl and (2) phenylglyoxylonitrile-2-oxime-cyanomethyl ether in sufficient amount to prevent injury to crops treated with said herbicide composition.
Claim 3
Dependent Claim
47 words
In the method of controlling weeds in sorghum cultures wherein a herbicidally effective amount of a chloroacetanilide compound of claim 1 is applied to the habitat of said weeds, the improvement comprising applying to said habitat, in sufficient amount to prevent injury to the sorghum phenylglyoxylonitrile-2-oxime-cyanomethyl ether.
Claim 4
Independent Claim
94 words
A method for protecting sorghum and rice crops from injury arising from the action of a herbicidal chloroacetanilide of the formula ##STR9## wherein R 1 is lower alkyl, lower alkoxy, lower alkoxyalkyl, fluorine or chlorine and R 2 , R 4 and R 5 independently of one another are hydrogen, lower alkyl, lower alkoxy, lower alkoxyalkyl or chlorine, and R is 1,3-dioxolan-2-yl-alkyl, 1,3-dioxolan-5-yl-alkyl, 1,3-dioxan-2-yl-alkyl, furanylmethyl or tetrahydrofuranylmethyl, said method comprising applying to the soil in the rows of sorghum or rice seed, prior to treatment with the herbicide, a crop-protecting amount of phenylglyoxylonitrile-2-oxime-cyanomethyl ether.
Claim 5
Independent Claim
94 words
A method for protecting sorghum and rice crops from injury arising from the action of a herbicidal chloroacetanilide of the formula ##STR9## wherein R 1 is lower alkyl, lower alkoxy, lower alkoxyalkyl, fluorine or chlorine and R 2 , R 4 and R 5 independently of one another are hydrogen, lower alkyl, lower alkoxy, lower alkoxyalkyl or chlorine, and R is 1,3-dioxolan-2-yl-alkyl, 1,3-dioxolan-5-yl-alkyl, 1,3-dioxan-2-yl-alkyl, furanylmethyl or tetrahydrofuranylmethyl, said method comprising applying to the soil in the rows of sorghum or rice seed, prior to treatment with the herbicide, a crop-protecting amount of phenylglyoxylonitrile-2-oxime-cyanomethyl ether.
Claim 6
Dependent Claim
12 words
A method according to claim 3 in which the crop is sorghum.
Claim 7
Independent Claim
78 words
A method for protecting crops from injury caused by application of a herbicidal chloroacetanilide compound of the formula ##STR10## wherein R 1 is lower alkyl, lower alkoxy, lower alkoxyalkyl, fluorine or chlorine and R 2 , R 4 and R 5 independently of one another are hydrogen, lower alkyl, lower alkoxy, lower alkoxyalkyl or chlorine, and R is 1,3-dioxolan-2-yl-alkyl, 1,3-dioxolan-5-yl-alkyl, 1,3-dioxan-2-yl-alkyl, furanylmethyl, or tetrahydrofuranylmethyl, said method comprising applying to the crop seeds, a crop-protecting amount of phenylglyoxylonitrile-2-oxime-cyanomethyl ether.
Claim 8
Independent Claim
78 words
A method for protecting crops from injury caused by application of a herbicidal chloroacetanilide compound of the formula ##STR10## wherein R 1 is lower alkyl, lower alkoxy, lower alkoxyalkyl, fluorine or chlorine and R 2 , R 4 and R 5 independently of one another are hydrogen, lower alkyl, lower alkoxy, lower alkoxyalkyl or chlorine, and R is 1,3-dioxolan-2-yl-alkyl, 1,3-dioxolan-5-yl-alkyl, 1,3-dioxan-2-yl-alkyl, furanylmethyl, or tetrahydrofuranylmethyl, said method comprising applying to the crop seeds, a crop-protecting amount of phenylglyoxylonitrile-2-oxime-cyanomethyl ether.
Claim 9
Dependent Claim
12 words
A method according to claim 5 in which the crop is sorghum.
Claim 10
Independent Claim
85 words
A method for selectively controlling weeds in sorghum cultures which comprises applying to a culture of sorghum grown from seeds treated with a safening amount of phenylglyoxylonitrile-2-oxime-cyanomethyl ether, a herbicidally effective amount of a chloroacetanilide compound of the formula ##STR11## wherein R 1 is lower alkyl, lower alkoxy, lower alkoxyalkyl, fluorine or chlorine, and R 2 , R 4 and R 5 independently of one another are hydrogen, lower alkyl, lower alkoxy, lower alkoxyalkyl, or chlorine, and R is 1,3-dioxolan-2-yl-alkyl, 1,3-dioxolan-5-yl-alkyl, 1,3-dioxan-2-yl-alkyl, furanylmethyl, or tetrahydrofuranylmethyl.
Claim 11
Independent Claim
85 words
A method for selectively controlling weeds in sorghum cultures which comprises applying to a culture of sorghum grown from seeds treated with a safening amount of phenylglyoxylonitrile-2-oxime-cyanomethyl ether, a herbicidally effective amount of a chloroacetanilide compound of the formula ##STR11## wherein R 1 is lower alkyl, lower alkoxy, lower alkoxyalkyl, fluorine or chlorine, and R 2 , R 4 and R 5 independently of one another are hydrogen, lower alkyl, lower alkoxy, lower alkoxyalkyl, or chlorine, and R is 1,3-dioxolan-2-yl-alkyl, 1,3-dioxolan-5-yl-alkyl, 1,3-dioxan-2-yl-alkyl, furanylmethyl, or tetrahydrofuranylmethyl.
Claim 12
Dependent Claim
92 words
Rice or sorghum seed, the plants grown from which are resistant to injury be pre-emergence application of a herbicidal compound of the formula ##STR12## wherein R 1 is lower alkyl, lower alkoxy, lower alkoxyalkyl, fluorine or chlorine, and R 2 , R 4 and R 5 independently of one another are hydrogen, lower alkyl, lower alkoxy, lower alkoxyalkyl, or chlorine, and R is 1,3-dioxolan-2-yl-alkyl, 1,3-dioxolan-5-yl-alkyl, 1,3-dioxan-2-yl-alkyl, furanylmethyl, or tetrahydrofuranylmethyl, said seed being coated with phenylglyoxylonitrile-2-oxime-cyanomethyl ether in an amount ranging from about 5 to about 500 grams per 100 kilograms of seed.
Claim 13
Dependent Claim
92 words
Rice or sorghum seed, the plants grown from which are resistant to injury be pre-emergence application of a herbicidal compound of the formula ##STR12## wherein R 1 is lower alkyl, lower alkoxy, lower alkoxyalkyl, fluorine or chlorine, and R 2 , R 4 and R 5 independently of one another are hydrogen, lower alkyl, lower alkoxy, lower alkoxyalkyl, or chlorine, and R is 1,3-dioxolan-2-yl-alkyl, 1,3-dioxolan-5-yl-alkyl, 1,3-dioxan-2-yl-alkyl, furanylmethyl, or tetrahydrofuranylmethyl, said seed being coated with phenylglyoxylonitrile-2-oxime-cyanomethyl ether in an amount ranging from about 5 to about 500 grams per 100 kilograms of seed.
Claim 14
Dependent Claim
25 words
Seed according to claim 8 which is coated with phenylglyoxylonitrile-2-oxime-cyanomethyl ether in an amount ranging from 50 to 400 grams per 100 kilograms of seed.
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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) | 1983-09-30 | 1984-03-31 | 1984-09-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-30 | 1988-03-31 | 1988-09-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-30 | 1992-03-31 | 1992-09-30 | $7700.00 | Window Closed / Lapsed |