Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-09-21
1995-10-31
Robinson, Allen J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549 22, 549 77, 549230, 549373, 549451, 549426, 549496, 558257, 560 11, 560 12, 560330, 564 85, 564 86, 564 88, C07C26500, C07C31116, C07D33908, C07D33310
Patent
active
054630819
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
This application is a 371 of PCT/EP92/00304 filed Feb. 12, 1992. The invention relates to the field of crop protection agents, in particular selective herbicides and growth regulators of the type of the phenylsulfonylureas which are substituted by a heterocycle.
EP-A-007,687 has already disclosed, inter alia, sulfonylureas of the formula (1) ##STR4## in which R.sup.2 is H, Cl, Br, F, (C.sub.1 -C.sub.3)alkyl, --NO.sub.2, --SO.sub.2 CH.sub.3, --OCH.sub.3, --SCH.sub.2, --CF.sub.3, --N(CH.sub.3).sub.2, --NH.sub.2 or --CN; R.sup.3 is H, Cl, Br, F or CH.sub.3 ; X is CH or N, Q is O, S or optionally substituted NH; and Y and Z are H, Cl or various organic radicals. The compounds have been described as herbicides and plant growth regulators.
EP-A-0,291,851 and DE-A-3,900,472 have disclosed herbicidal and plant growth-regulating sulfonylureas of the formula (2) ##STR5## in which Z is F, Cl or Br, R.sup.1 is H, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl, R.sup.2 is H,CH.sub.3 or C.sub.2 H.sub.5, R.sup.3 is H, F, Cl, Br, CH.sub.3 or OCH.sub.3, R.sup.4 is H, CH.sub.3, (C.sub.1 -C.sub.4)alkoxy and X is CH or N.
U.S. Pat. No. 4,566,898 furthermore describes the sulfonylurea of the formula (3) ##STR6## as a herbicide which has outstanding properties, in particular for controlling black grass in barley and wheat.
Surprisingly, it has now been found that some iodinated arylsulfonylureas have advantageous properties.
The present invention therefore relates to compounds of the formula (I) and salts thereof, ##STR7## where Q is oxygen, sulfur or --N(R.sup.4)--, preferably O or S, in particular O; simultaneously CH, preferably Y is CH or N and Z is N; (C.sub.2 -C.sub.10)alkynyl; (C.sub.1 -C.sub.6)alkyl, which is mono substituted to tetrasubstituted by radicals selected from the group comprising halogen, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)thioalkyl, --CN, (C.sub.2 -C.sub.5)alkoxycarbonyl and (C.sub.2 -C.sub.6)alkenyl; (C.sub.3 -C.sub.8)cycloalkyl which is unsubstituted or substituted by radicals selected from the group comprising (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkylthio and halogen; (C.sub.5 -C.sub.8)cycloalkenyl; phenyl (C.sub.1 -C.sub.4)alkyl which is unsubstituted or substituted in the phenyl radical; or a radical of the formulae A-1 to A-10 ##STR8## where X is O, S, S(O) or SO.sub.2 ; (C.sub.1 -C.sub.3)alkoxy, where the two last-mentioned radicals are unsubstituted or monosubstituted or polysubstituted by halogen or (C.sub.1 -C.sub.3)alkoxy; (C.sub.1 -C.sub.3)alkoxy or (C.sub.1 -C.sub.3)alkylthio, where the abovementioned alkyl-containing radicals are unsubstituted or monosubstituted or polysubstituted by halogen or monosubstituted or disubstituted by (C.sub.1 -C.sub.3)alkoxy or (C.sub.1 -C.sub.3)alkylthio; or a radical of the formula NR.sup.5 R.sup.6, (C.sub.1 -C.sub.6)-cycloalkyl, (C.sub.2 -C.sub.4)alkenyl, (C.sub.2 -C.sub.4)alkynyl, (C.sub.3 -C.sub.4)alkenyloxy or (C.sub.1 -C.sub.6)alkynyloxy; and -C.sub.4)alkyl, (C.sub.3 -C.sub.4)alkenyl, (C.sub.1 -C.sub.4)haloalkyl or (C.sub.1 -C.sub.4)alkoxy.
In formula (I) and in what follows, alkyl, alkoxy, haloalkyl, alkylamino and alkylthio radicals as well as the corresponding unsaturated and/or substituted radicals can in each case be straight-chain or branched. Alkyl radicals, also in composite meanings such as alkoxy, haloalkyl etc., are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl etc. Alkenyl and alkynyl radicals have the meanings of the unsaturated radicals which are possible and which correspond to the alkyl radicals, such as, for example, 2-propenyl, 2- or 3-butenyl, 2-propynyl and 2- or 3-butynyl. Halogen is fluorine, chlorine, bromine or iodine. Aryl is preferably a carbocyclic or heterocyclic aromatic ring which can optionally be fused with an aliphatic or aromatic ring; in particular, aryl is phenyl. Substituted phenyl is phenyl which is substituted for example by one or more, preferably one to three, radicals selected from the group comprising halogen, (C.sub.1 -C.sub.
REFERENCES:
patent: 3965173 (1976-06-01), Chubb et al.
patent: 4383113 (1983-05-01), Levitt
patent: 4480101 (1984-10-01), Meyer
patent: 4537896 (1985-08-01), Claeson et al.
patent: 4551531 (1985-11-01), Meyer et al.
patent: 5104441 (1992-04-01), Hamprecht
patent: 5143937 (1992-09-01), Lang et al.
Bauer Klaus
Bieringer Hermann
Ort Oswald
Cebulak Mary C.
Hoechst Aktiengesellschaft
Robinson Allen J.
LandOfFree
Arylsulfonylureas, processes for their preparation, and their us does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Arylsulfonylureas, processes for their preparation, and their us, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Arylsulfonylureas, processes for their preparation, and their us will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1773479