US4183742A
Expired / Lapsed
US
⏱️ 0.0 years remaining
4,5-Dichloro-imidazole-1-carboxylic acid aryl esters and their use as plant protection agents
Assignee: Bayer AG
•
Filing: 1977-09-21
•
Granted: 1980-01-15
•
Expires: 1997-09-21
Abstract
Abstract A 4,5-dichloro-imidazole-1-carboxylic acid aryl ester of the formula ##STR1## in which X represents trifluoromethyl, cyano or a group ##STR2## in which R 1 represents an optionally substituted saturated or unsaturated aliphatic radical, R 2 represents hydrogen, alkyl with 1 to 8 carbon atoms, alkenyl with up to 8 carbon atoms or the formyl group, R 3 represents alkyl with 1 to 8 carbon atoms or alkenyl or alkynyl each with up to 8 carbon atoms, it being possible for each of these alkyl, alkenyl and alkynyl radicals to carry one or more substituents, or represents cycloalkyl with 5 to 7 carbon atoms in the ring which is optionally substituted by alkyl with 1 to 6 carbon atoms, or represents phenyl which may optionally carry one or more substituents, or R 2 and R 3 conjointly with the adjoining nitrogen atom form an optionally substituted 5- to 7-membered heterocyclic radical in which 1 to 3 ring members may be selected from oxygen, sulfur and nitrogen, Y represents halogen, alkyl with 1 to 6 carbon atoms, trifluoromethyl, alkoxy with 1 to 6 carbon atoms, nitro, cyano or a ##STR3## group, in which R 4 represents alkyl with 1 to 6 carbon atoms and n represents 0, 1, 2, 3, 4, or 5, which possesses plant protection properties especially herbicidal and plant growth regulant properties.
Inventors
- 👤 Klaus Sasse
- 👤 Gunther Beck
- 👤 Ludwig Eue
- 👤 Robert R. Schmidt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 04:53
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/12; C07D487/14; A; A01; A01N; A01N47/00; A01N47/08; A01N47/10; A01N47/22; C07D233/00; C07D233/54; C07D233/66; C07D233/68; C07D233/90
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
229 words
A 4,5-dichloro-imidazole-1-carboxylic acid aryl ester of the formula ##STR70## in which X represents a group ##STR71## in which R 1 represents a straight or branched alkyl radical with 1 to 6 carbon atoms or straight or branched alkenyl or alkynyl, each with up to 6 carbon atoms, which radicals can be carrying one or more substituents selected from fluorine, chlorine, bromine, alkoxy with 1 to 6 carbon atoms and alkylmercapto with 1 to 6 carbon atoms, R 2 represents hydrogen, alkyl with 1 to 8 carbon atoms, alkenyl with up to 8 carbon atoms in the formyl group, R 3 represents alkyl with 1 to 8 carbon atoms or alkenyl or alkynyl, each with up to 8 carbon atoms, it being possible for each of these alkyl, alkenyl and alkynyl radicals to carry one or more substituents selected from alkoxy with 1 to 4 carbon atoms and alkylmercapto with 1 to 4 carbon atoms, or R 2 and R 3 conjointly with the adjoining nitrogen atom form a heterocyclic radical selected from pyrrolidinyl, piperidinyl and hexamethyleneimidinyl Y represents halogen, alkyl with 1 to 6 carbon atoms, trifluoromethyl, alkoxy with 1 to 6 carbon atoms, alkylmercapto with 1 to 6 carbon atoms, nitro, cyano or a ##STR72## group, in which R 4 represents alkyl with 1 to 6 carbon atoms and n represents 0, 1, 2, 3, 4, or 5.
Claim 2
Dependent Claim
229 words
A 4,5-dichloro-imidazole-1-carboxylic acid aryl ester of the formula ##STR70## in which X represents a group ##STR71## in which R 1 represents a straight or branched alkyl radical with 1 to 6 carbon atoms or straight or branched alkenyl or alkynyl, each with up to 6 carbon atoms, which radicals can be carrying one or more substituents selected from fluorine, chlorine, bromine, alkoxy with 1 to 6 carbon atoms and alkylmercapto with 1 to 6 carbon atoms, R 2 represents hydrogen, alkyl with 1 to 8 carbon atoms, alkenyl with up to 8 carbon atoms in the formyl group, R 3 represents alkyl with 1 to 8 carbon atoms or alkenyl or alkynyl, each with up to 8 carbon atoms, it being possible for each of these alkyl, alkenyl and alkynyl radicals to carry one or more substituents selected from alkoxy with 1 to 4 carbon atoms and alkylmercapto with 1 to 4 carbon atoms, or R 2 and R 3 conjointly with the adjoining nitrogen atom form a heterocyclic radical selected from pyrrolidinyl, piperidinyl and hexamethyleneimidinyl Y represents halogen, alkyl with 1 to 6 carbon atoms, trifluoromethyl, alkoxy with 1 to 6 carbon atoms, alkylmercapto with 1 to 6 carbon atoms, nitro, cyano or a ##STR72## group, in which R 4 represents alkyl with 1 to 6 carbon atoms and n represents 0, 1, 2, 3, 4, or 5.
Claim 3
Dependent Claim
245 words
A compound according to claim 1 wherein X represents a group --CO--OR 1 or --CO--NR 2 R 3 in which R 1 represents a straight or branched alkyl radical with 1 to 6 carbon atoms, which alkyl radical can carry one or more substituents selected from fluorine, chlorine, bromine, alkoxy with 1 to 4 carbon atoms and alkylmercapto with 1 to 4 carbon atoms or R 1 represents a straight chain or branched alkenyl or alkynyl radical, each with up to 6 carbon atoms; R 2 represents hydrogen, straight or branch chained alkyl with 1 to 6 carbon atoms, straight or branched alkenyl with up to 6 carbon atoms or the formyl group; R 3 represents straight or branched alkyl with 1 to 6 carbon atoms or straight or branched alkenyl or alkynyl each with up to 6 carbon atoms, optionally substituted by one or more substituents selected from the group consisting of alkoxy with 1 to 3 carbon atoms and alkylmercapto with 1 to 3 carbon atoms; or R 2 and R 3 conjointly with the adjoining nitrogen atom form a heterocyclic ring selected from pyrrolidinyl, piperidinyl and hexamethyleneimidinyl; and Y represents fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylmercapto with 1 to 4 carbon atoms, trifluoromethyl, nitro, cyano or a --CO--OR 4 group, in which R 4 represents alkyl with 1 to 4 carbon atoms; and n represents 0, 1, 2, or 3.
Claim 4
Dependent Claim
11 words
A compound according to claim 1 having the following formula ##STR73##
Claim 5
Dependent Claim
11 words
A compound according to claim 1 having the following formula ##STR74##
Claim 6
Dependent Claim
11 words
A compound according to claim 1 having the following formula ##STR75##
Claim 7
Dependent Claim
11 words
A compound according to claim 1 having the following formula ##STR76##
Claim 8
Dependent Claim
11 words
A compound according to claim 1 having the following formula ##STR77##
Claim 9
Dependent Claim
11 words
A compound according to claim 1 having the following formula ##STR78##
Claim 10
Dependent Claim
11 words
A compound according to claim 1 having the following formula ##STR79##
Claim 11
Dependent Claim
11 words
A compound according to claim 1 having the following formula ##STR80##
Claim 12
Dependent Claim
11 words
A compound according to claim 1 having the following formula ##STR81##
Claim 13
Dependent Claim
11 words
A compound according to claim 1 having the following formula ##STR82##
Claim 14
Dependent Claim
11 words
A compound according to claim 1 having the following formula ##STR83##
Claim 15
Dependent Claim
23 words
A herbicide containing as an active ingredient a herbicidally effective amount of a compound according to claim 1 in admixture with a diluent.
Claim 16
Dependent Claim
26 words
A method of protecting a plant which comprises applying to the plant or its habitat a herbicidally effective amount of a compound according to claim 1.
Claim 17
Dependent Claim
37 words
A method according to claim 15 wherein said compound is 4,5-dichloro-2-trifluoromethyl-imidazole-1-carboxylic acid phenyl ester, 4,5-dichloro-2-cyano-imidazole-1-carboxylic acid phenyl ester, a compound of the formula ##STR84## a compound of the formula ##STR85## or a compound of the formula ##STR86##
Claim 18
Dependent Claim
26 words
A method according to claim 15 wherein said 4,5-dichloro-imidazole-1-carboxylic acid aryl ester is applied to a plant or its habitat prior to emergence of any weeds.
Claim 19
Dependent Claim
30 words
A method according to claim 15 wherein said 4,5-dichloro-imidazole-1-carboxylic acid aryl ester is applied to a plant which is selected from the group consisting of oats, cotton, wheat and maize.
Claim 20
Dependent Claim
11 words
A compound according to claim 1 having the following formula ##STR87##
Claim 21
Dependent Claim
11 words
A compound according to claim 1 having the following formula ##STR88##
Claim 22
Dependent Claim
23 words
An insecticide containing as an active ingredient an insecticidally effective amount of a compound according to claim 1 in admixture with a diluent.
Claim 23
Dependent Claim
23 words
An acaricide containing as an active ingredient an acaricidally effective amount of a compound according to claim 1 in admixture with a diluent.
Claim 24
Dependent Claim
27 words
A plant growth regulant containing as an active ingredient a plant growth regulatingly effective amount of a compound according to claim 1 in admixture with a diluent.
Claim 25
Dependent Claim
26 words
A method of protecting a plant which comprises applying to the plant or its habitat an insecticidally effective amount of a compound according to claim 1.
Claim 26
Dependent Claim
26 words
A method of protecting a plant which comprises applying to the plant or its habitat an acaricidally effective amount of a compound according to claim 1.
Claim 27
Dependent Claim
31 words
A method of regulating the growth of a plant which comprises applying to the plant or its habitat a plant growth regulatingly effective amount of a compound according to claim 1.
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) | 1983-01-14 | 1983-07-16 | 1984-01-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-01-14 | 1987-07-16 | 1988-01-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-01-14 | 1991-07-16 | 1992-01-15 | $7700.00 | Window Closed / Lapsed |