US3993469A
Expired / Lapsed
US
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Azolylamidine compounds and herbicidal compositions
Assignee: Bayer AG
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Filing: 1974-04-08
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Granted: 1976-11-23
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Expires: 1994-04-08
Abstract
Abstract New azolylamidines of the formula ##SPC1## Wherein n is an integer from 0 to 5, R 1 is halogen, alkyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, halophenoxy or haloalkyl; R 2 and R 3 , independently of one another, are each hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkoxy or alkoxycarbonylalkyl, of, preferably not more than 7 carbon atoms; or taken together, represent a lower alkylene bridge which can be interrupted by one or more hetero-atoms; and Az represents an azolyl radical selected from imidazol-1-yl, pyrrol-1-yl, pyrazol-1-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-4-yl or 1,2,3-triazol-1-yl, And their salts are outstandingly effective herbicides showing particularly selective action.
Inventors
- 👤 Erik Regel
- 👤 Ludwig Eue
- 👤 Robert R. Schmidt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 06:08
CPC Classifications
C; C07; C07D; C07D249/00; C07D249/02; C07D249/08; C07C; C07C275/00; C07C275/70; C07D207/00; C07D207/02; C07D207/30; C07D207/34; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D231/54; C07D231/56; C07D233/00; C07D233/54; C07D233/56; C07D233/66; C07D233/68; C07D233/91; C07D233/92; C07D235/00; C07D235/02; C07D235/04; C07D235/06; C07D249/04
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
135 words
Azolylamidine compound of the formula ##SPC19## wherein n is an integer from 0 to 2, inclusive, R 1 is individually selected from halogen, alkyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, halophenoxy and haloalkyl and contains not more than 6 carbon atoms; R 2 is selected from hydrogen, alkyl, or cycloalkyl and contains not more than 7 carbon atoms; R 3 is selected from hydrogen, alkyl, and cycloalkyl and contains not more than 7 carbon atoms; R 2 and R 3 , taken together represent a lower alkylene bridge of up to 5 carbon atoms; Az is an imidazolyl radical selected from imidazol-1-yl and imidazol-1-yl substituted with at least one of alkyl of up to 6 carbon atoms, halogen and nitro provided that there is not more than one nitro substituent and salts thereof with physiologically tolerated acids.
Claim 2
Dependent Claim
135 words
Azolylamidine compound of the formula ##SPC19## wherein n is an integer from 0 to 2, inclusive, R 1 is individually selected from halogen, alkyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, halophenoxy and haloalkyl and contains not more than 6 carbon atoms; R 2 is selected from hydrogen, alkyl, or cycloalkyl and contains not more than 7 carbon atoms; R 3 is selected from hydrogen, alkyl, and cycloalkyl and contains not more than 7 carbon atoms; R 2 and R 3 , taken together represent a lower alkylene bridge of up to 5 carbon atoms; Az is an imidazolyl radical selected from imidazol-1-yl and imidazol-1-yl substituted with at least one of alkyl of up to 6 carbon atoms, halogen and nitro provided that there is not more than one nitro substituent and salts thereof with physiologically tolerated acids.
Claim 3
Dependent Claim
11 words
Azolylamidine compound as claimed in claim 1 wherein n is 0.
Claim 4
Dependent Claim
11 words
Azolylamidine compound as claimed in claim 1 wherein n is 1.
Claim 5
Dependent Claim
11 words
Azolylamidine compound as claimed in claim 1 wherein n is 2.
Claim 6
Dependent Claim
12 words
Azolylamidine compound as claimed in claim 1 wherein R 1 is halogen.
Claim 7
Dependent Claim
12 words
Azolylamidine compound as claimed in claim 1 wherein R 1 is chloro.
Claim 8
Dependent Claim
12 words
Azolylamidine compound as claimed in claim 1 wherein R 1 is alkyl.
Claim 9
Dependent Claim
16 words
Azolylamide compound as claimed in claim 1 wherein R 1 is alkoxy, alkylthio, haloalkoxy or haloalkylthio.
Claim 10
Dependent Claim
12 words
Azolylamidine compound as claimed in claim 1 wherein R 1 is halophenoxy.
Claim 11
Dependent Claim
12 words
Azolylamidine compound as claimed in claim 1 wherein R 1 is haloalkyl.
Claim 12
Dependent Claim
17 words
Azolylamidine compound as claimed in claim 1 wherein one of R 2 and R 3 is hydrogen.
Claim 13
Dependent Claim
17 words
Azolylamidine compound as claimed in claim 1 wherein one of R 2 and R 3 is alkyl.
Claim 14
Dependent Claim
11 words
Azolylamidine compound as claimed in claim 1 wherein R 3 cycloalkyl.
Claim 15
Dependent Claim
117 words
Azolylamidine compound of the formula ##SPC20## wherein n is an integer of from 0 to 5, inclusive, R 1 is halogen; R 2 is selected from hydrogen, alkyl, or cycloalkyl and contains not more than 7 carbon atoms; R 3 is selected from hydrogen, alkyl, and cycloalkyl and contains not more than 7 carbon atoms; R 2 and R 3 , taken together represent a lower alkylene bridge of up to 5 carbon atoms; Az is an imidazolyl radical selected from imidazol-1-yl and imidazol-1-yl substituted with at least one of alkyl of up to 6 carbon atoms, halogen and nitro provided that there is not more than one nitro substituent and salts thereof with physiologically tolerated acids.
Claim 16
Dependent Claim
117 words
Azolylamidine compound of the formula ##SPC20## wherein n is an integer of from 0 to 5, inclusive, R 1 is halogen; R 2 is selected from hydrogen, alkyl, or cycloalkyl and contains not more than 7 carbon atoms; R 3 is selected from hydrogen, alkyl, and cycloalkyl and contains not more than 7 carbon atoms; R 2 and R 3 , taken together represent a lower alkylene bridge of up to 5 carbon atoms; Az is an imidazolyl radical selected from imidazol-1-yl and imidazol-1-yl substituted with at least one of alkyl of up to 6 carbon atoms, halogen and nitro provided that there is not more than one nitro substituent and salts thereof with physiologically tolerated acids.
Claim 17
Dependent Claim
20 words
Azolylamidine compound as claimed in claim 1 wherein R 2 and R 3 taken together are ethylene, tetramethylene or pentamethylene.
Claim 18
Dependent Claim
11 words
Azolyamidine compound as claimed in claim 14 wherein n is 3.
Claim 19
Dependent Claim
16 words
Azolylamidine compound as claimed in claim 1 wherein Az is imidazolyl substituted with a nitro group.
Claim 20
Dependent Claim
20 words
Azolylamidine compound as claimed in claim 1 wherein Az is imidazolyl substituted with one nitro group and one alkyl group.
Claim 21
Dependent Claim
11 words
Azolylamidine compound as claimed in claim 1 wherein Az is imidazolyl-1-yl.
Claim 22
Dependent Claim
18 words
Azolylamidine compound as claimed in claim 1 wherein Az is imidazolyl substituted with 2 to 3 chlorine atoms.
Claim 23
Dependent Claim
16 words
Azolylamidine compound as claimed in claim 1 wherein Az is imidazolyl substituted with two alkyl groups.
Claim 24
Dependent Claim
9 words
Azolylamidine compound as claimed in claim 1 designated N(4-chlorophenyl)-N',N'-dimethyl-imidazolyl-(1)-amidine.
Claim 25
Dependent Claim
9 words
Azolylamidine compound as claimed in claim 1 designated N-(3-chlorophenyl)-N',N'-dimethyl-imidazolyl-(1)-amidine.
Claim 26
Dependent Claim
9 words
Azolylamidine compound as claimed in claim 1 designated N-(4-fluorophenyl)-N',N'-dimethyl-imidazolyl-(1)-amidine.
Claim 27
Dependent Claim
18 words
Herbicidal composition comprising herbicidally acceptable carrier and, in effective amounts, an azolylamidine compound as claimed in claim 1.
Claim 28
Dependent Claim
149 words
Method of combatting undesired vegetation, which method comprises applying to said vegetation or its habitat a herbicidally effective amount of an azolylamidine compound of the formula ##SPC21## wherein n is an integer from 0 to 2, inclusive, R 1 is individually selected from halogen, alkyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, halophenoxy and haloalkyl and contains not more than 6 carbon atoms; R 2 is selected from hydrogen, alkyl, or cycloalkyl and contains not more than 7 carbon atoms; R 3 is selected from hydrogen, alkyl, and cycloalkyl and contains not more than 7 carbon atoms; R 2 and R 3 , taken together, represent a lower alkylene bridge of up to 5 carbon atoms; Az is an azolyl radical selected from imidazol-1-yl and imidazol-1-yl substituted with at least one of alkyl of up to 6 carbon atoms, halogen and nitro provided that there is not more than one nitro substituent.
Claim 29
Dependent Claim
149 words
Method of combatting undesired vegetation, which method comprises applying to said vegetation or its habitat a herbicidally effective amount of an azolylamidine compound of the formula ##SPC21## wherein n is an integer from 0 to 2, inclusive, R 1 is individually selected from halogen, alkyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, halophenoxy and haloalkyl and contains not more than 6 carbon atoms; R 2 is selected from hydrogen, alkyl, or cycloalkyl and contains not more than 7 carbon atoms; R 3 is selected from hydrogen, alkyl, and cycloalkyl and contains not more than 7 carbon atoms; R 2 and R 3 , taken together, represent a lower alkylene bridge of up to 5 carbon atoms; Az is an azolyl radical selected from imidazol-1-yl and imidazol-1-yl substituted with at least one of alkyl of up to 6 carbon atoms, halogen and nitro provided that there is not more than one nitro substituent.
Claim 30
Dependent Claim
29 words
Method as claimed in claim 26 wherein said compound is applied to weeds growing in a crop cultivation to selectively damage the weeds without substantial injury to the crops.
Claim 31
Dependent Claim
15 words
Method as claimed in claim 26 wherein said compound is selected from N-(4-chlorophenyl)-N',N'-dimethyl-imidazolyl-(1)-amidine, N-(3-chlorophenyl)-N',N'-dimethyl-imidazolyl-(1)-amidine, N-(4-fluorophenyl)-N',N'-dimethyl-imidazolyl-(1)-amidine.
References Cited (Backward Citations)
US3174997A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-11-23 | 1980-05-24 | 1980-11-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-11-23 | 1984-05-24 | 1984-11-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-11-23 | 1988-05-24 | 1988-11-23 | $7700.00 | Window Closed / Lapsed |