Claims
- 1. A 4,5-dichloroimidazole-2-carboxylic acid derivative selected from the group consisting of ##STR321## in which W is O,S or .dbd.N-R.sup.3
- in which
- R.sup.3 denotes hydrogen; OH; C.sub.1-12 -alkyl optionally substituted by halogen, OH, C.sub.1-4 -alkoxy, phenoxy (which is optionally substituted by C.sub.1-4 -alkyl or halogen), C.sub.1-4 -alkylmercapto, benzylmercapto, COOH, CONH.sub.2, CONH-alkyl, CON(alkyl).sub.2 or CONH-aryl (in which the aryl group is phenyl or naphthyl and is optionally substituted by halogen, C.sub.1-4 -alkyl, CF.sub.3, C.sub.1-4 -alkoxy or NO.sub.2), or by cycloalkyl with 5 or 6 ring carbon atoms (optionally substituted by C.sub.1-4 -alkyl; C.sub.3-8 alkenyl (optionally substituted by halogen or C.sub.1-4 -alkoxy), C.sub.3-12 -alkynyl (optionally substituted by phenyl that is optionally substituted by halogen, C.sub.1-4 -alkyl, CF.sub.3, C.sub.1-4 -alkoxy or nitro, or by cycloalkyl with 5 or 6 ring carbon atoms), cycloalkyl with 4-8 ring carbon atoms (optionally substituted by C.sub.1-4 -alkyl or CF.sub.3 or optionally containing a fused benzene ring), or aryl, or
- R.sup.3 represents a group --OR.sup.4 wherein
- R.sup.4 represents C.sub.1-4 -alkyl, benzyl or a group ##STR322## wherein R.sup.7 has the below mentioned meanings,
- R.sup.3 furthermore represents a group ##STR323## in which R.sup.11 and R.sup.12, which may be identical or different, each denotes hydrogen, C.sub.1-12 -alkyl or C.sub.3-8 -alkenyl (which may be optionally substituted by chlorine, fluorine, bromine, OH, C.sub.1-4 -alkoxy, phenoxy which may be optionally substituted by C.sub.1-4 -alkyl, halogen or C.sub.1-4 -alkoxy), the acyloxy radical ##STR324## C.sub.1-4 -alkylmercapto (optionally substituted by phenyl), phenylmercapto (optionally substituted by halogen or C.sub.1-4 -alkyl), --CN, --COOH, --CONH(C.sub.1-4 -alkyl).sub.2, --CONH--aryl or aryl (the aryl group being phenyl or naphthyl, which is optionally substituted by halogen, C.sub.1-4 -alkyl, CF.sub.3, C.sub.1-4 -alkoxy or NO.sub.2), cyclopentyl, cyclohexyl, or a group ##STR325## wherein R.sup.11 has one of the preceding meanings, C.sub.3-12 -alkynyl (optionally substituted by phenyl, cyclohexyl or cyclopentyl), C.sub.4-8 -cycloalkyl (optionally substituted by C.sub.1-4 -alkyl or CF.sub.3) or aryl, preferably phenyl or naphthyl, which may be substituted by C.sub.1-4 -alkyl, C.sub.1-4 -halogenoalkyl, halogen, C.sub.1-4 -alkoxy, acetyl, aryloxy or arylmercapto (which may be substituted by halogen, C.sub.1-4 -alkyl, CF.sub.3, C.sub.1-4 -alkoxy or C.sub.1-4 -alkylmercapto), C.sub.1-4 -alkylmercapto, C.sub.1-4 -alkylsulphonyl, alkoxycarbonyl, aminocarbonyl, CN, NO.sub.2, mono-C.sub.1-4 -alkylamino, di(C.sub.1-4 -alkyl)amino, C.sub.1-4 -halogenoalkoxy or C.sub.1-4 -halogenoalkylmercapto, or
- R.sup.12 can denote OH, C.sub.1-4 -alkoxy (optionally substituted by phenyl), or an acyl group of the formula ##STR326## in which R.sup.13 denotes hydrogen, C.sub.1-12 -alkyl or C.sub.2-8 -alkenyl, C.sub.2-8 -alkynyl, cycloalkyl with 3-8 ring carbon atoms, phenyl or naphthyl (either of which can optionally be substituted by halogen, C.sub.1-4 -alkoxy, C.sub.1-4 -alkyl, CF.sub.3 or NO.sub.2) or
- R.sup.12 can denote a group of the formula ##STR327## in which R.sup.14 denotes C.sub.1-12 -alkyl, C.sub.3-12 -alkenyl or C.sub.3-12 -alkynyl each of which can optionally be substituted by halogen, C.sub.1-4 -alkoxy, phenyl (itself optionally substituted by halogen or C.sub.1-4 -alkyl), cycloalkyl with 5 or 6 ring carbon atoms; cycloalkyl with 5 or 6 ring carbon atoms (optionally substituted by C.sub.1-4 -alkyl), or phenyl or naphthyl (either of which is optionally substituted by halogen, C.sub.1-4 -alkyl, CF.sub.3, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylmercapto, NO.sub.2 or CN), or
- R.sup.12 can denote a group of the formula ##STR328## in which the R.sup.15 moieties are identical or different and denote hydrogen, C.sub.1-2 -alkyl or C.sub.3-8 -alkenyl (either of which is optionally substituted by halogen, C.sub.1-4 -alkyl, CF.sub.3 C.sub.1-4 -alkoxy), phenyl (optionally substituted by halogen, C.sub.1-4 -alkyl, CF.sub.3, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylmercapto or NO.sub.2), cycloalkyl with 5 or 6 ring carbon atoms or a sulphonyl group --SO.sub.2 --R.sup.8 in which
- R.sup.8 denotes C.sub.1-12 -alkyl (optionally substituted by chlorine or fluorine), phenyl (optionally substituted by chlorine, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, CF.sub.3 or NO.sub.2) or a secondary amine group, or
- R.sup.12 can denote the group ##STR329## in which R.sup.5 and R.sup.6 can be identical or different and represent hydrogen, C.sub.1-4 -alkyl (which can optionally be substituted by phenyl, which can itself be optionally substituted by halogen or C.sub.1-4 -alkyl), phenyl (optionally substituted by halogen, NO.sub.2, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or CF.sub.3) or the group ##STR330## in which R.sup.7 denotes hydrogen, C.sub.1-12 -alkyl or C.sub.2-8 alkenyl either of which can be substituted by halogen, nitro, C.sub.1-4 -alkylmercapto, phenylmercapto (optionally substituted by halogen or C.sub.1-4 -alkyl), phenyl (optionally substituted by halogen or C.sub.1-4 -alkyl) or cycloalkyl with 5 or 6 ring carbon atoms; C.sub.2-8 -alkynyl, cycloalkyl with 3-6 ring carbon atoms, phenyl or naphthyl (either of which is optionally substituted by halogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, CF.sub.3 or NO.sub.2), or a group of the formula --OR.sup.26 or --SR.sup.26
- in which
- R.sup.26 denotes C.sub.1-12 -alkyl, C.sub.3-12 -alkenyl or C.sub.3-12 -alkynyl (any of which may be optionally substituted by halogen, C.sub.1-4 -alkoxy, phenyl (which may be substituted by halogen C.sub.1-4 -alkyl), cyclohexyl), C.sub.3-6 -cycloalkyl, or phenyl or naphthyl (either of which can optionally be substituted by halogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or nitro), or
- R.sup.7 denotes a group R.sup.27 -N-R.sup.27
- in which
- the R.sup.27 moieties are identical or different and denote hydrogen, C.sub.1-12 -alkyl or C.sub.3-8 -alkenyl (either of which can be optionally substituted by halogen, C.sub.1-4 -alkoxy or phenyl that is optionally substituted by C.sub.1-4 -alkyl or halogen), cycloalkyl with 5 or 6 carbon atoms or phenyl (which may be substituted by halogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylmercapto, CF.sub.3 or NO.sub.2), or R.sup.5 and R.sup.6 can conjointly denote the group ##STR331## in which the R.sup.9 moieties are identical or different and each denotes C.sub.1-12 -alkyl (which is optionally substituted by OH, C.sub.1-4 -alkoxy, COOH or COO(C.sub.1-4 -alkyl)), cycloalkyl with 5 or 6 ring carbon atoms, phenylalkyl or naphthylalkyl with 1-4 carbon atoms in the alkyl moiety (the phenyl or naphthyl moiety optionally being substituted by halogen, NO.sub.2, C.sub.1-4 -alkyl or C.sub.1-4 -alkoxy), phenyl or naphthyl (either of which is optionally substituted by OH, halogen, NO.sub.2, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylmercapto or CF.sub.3) or the R.sup.9 moieties can, conjointly with the adjacent carbon atom, form a carbocyclic ring, or one of the R.sup.9 moieties can be hydrogen, and Z denotes halogen, a group --OR.sup.10 or --SR.sup.10 in which ##STR332## R.sup.10 denotes hydrogen, a metal cation or a cation --NR.sub.4.sup.+ wherein R is hydrogen or an alkyl, aryl, cycloalkyl, or aralkyl group and 2 or 3 of the R moieties can form a 5- or 6-membered ring, or R.sup.10 denotes C.sub.1-8 -alkyl or C.sub.3-12 -alkenyl either of which is optionally substituted by chlorine, fluorine, bromine, acyloxy, wherein acyl denotes the radical of an aliphatic, cycloaliphatic, or aromatic carboxylic acid or the radical ##STR333## C.sub.1-4 -alkoxy, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxy, phenoxy or naphthoxy (either of which is optionally substituted by halogen, C.sub.1-4 -alkyl, CF.sub.3 or NO.sub.2), C.sub.1-4 -alkylmercapto (optionally substituted by phenyl that is optionally substituted by halogen or C.sub.1-4 -alkyl), arylmercapto, arylsulphonyl or arylsulphonyl (any of which may be substituted by C.sub.1-4 -alkyl or halogen), C.sub.1-4 -alkylsulphonyl, acylamino or diacylamino (wherein acyl denotes the radical of an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic carboxylic acid or of a carbonic or thiocarbonic acid derivative), CN, a carboxylic acid ester radical, cycloalkyl with 5 or 6 ring carbon atoms, phenyl (optionally substituted by halogen, C.sub.1-4 -alkyl or C.sub.1-4 -alkoxy) C.sub.3-12 -alkynyl, cycloalkyl with 3-6 ring carbon atoms (optionally substituted by halogen, C.sub.1-4 -alkoxy or C.sub.1-4 -alkyl), or phenyl or naphthyl.
- 2. A compound according to claim 1, in which Z denotes ##STR334##
- 3. A compound according to claim 1, in which Z denotes a group --O--R.sup.10 or --S--R.sup.10.
- 4. A 4,5-dichloro-imidazole-2-carboxylic acid derivative according to claim 1, wherein such derivative is 4,5-dichloro-2-trifluoromethyl-imidazole of the formula ##STR335##
- 5. A 4,5-dichloro-imidazole-2-carboxylic acid derivative according to claim 1, wherein such derivative is 4,5-dichloro-2-cyan-imidazole of the formula ##STR336##
- 6. A 4,5-dichloro-imidazole-2-carboxylic acid derivative according to claim 1, wherein such derivative is a 4,5-dichloroimidazol-2-carboxylic-tert.-butylester of the formula ##STR337##
- 7. A 4,5-dichloro-imidazole-2-carboxylic acid derivative according to claim 1, wherein such derivative is 4,5-dichloro-imidazole-2-carboxylic acid-bis-[2'-chlor-4'-trifluoro-methyl]-anilide of the formula ##STR338##
- 8. A herbicidal composition containing as active ingredient a herbicidally effective amount of a compound according to claim 1 in admixture with a diluent.
- 9. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to claim 1.
- 10. The method according to claim 9, in which said compound is
- 4,5-dichloro-2-trifluoromethyl-imidazole,
- 4,5-dichloro-2-cyan-imidazole,
- and
- 4,5-dicyloro-imidazole-2-carboxylic acid-bis-[2'-chlor-4'-trifluoro-methyl]-amnilide.
Priority Claims (3)
Number |
Date |
Country |
Kind |
2610527 |
Mar 1976 |
DEX |
|
2624759 |
Jun 1976 |
DEX |
|
2634053 |
Jul 1976 |
DEX |
|
Parent Case Info
This is a division of application Ser. No. 770,260 filed Feb. 18, 1977 now pending.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
3772315 |
Regel et al. |
Nov 1973 |
|
Divisions (1)
|
Number |
Date |
Country |
Parent |
770260 |
Feb 1977 |
|