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 Phenylalkenylcarboxylic acids and their esters

Details
Inventors: Plath, Peter; Eicken, Karl; Goetz, Norbert; Wild, Jochen; Meyer, Norbert; Wuerzer, Bruno;
Assignee: BASF Aktiengesellschaft (Ludwigshafen, DE)
Primary Examiner: Brown; Johnnie R.
Assistant Examiner: Tsung; Frederick F.
Attorney, Agent or Firm: Keil & Weinkauf

Phenylalkenylcarboxylic acid and esters thereof of the general formula I ##STR1## where X is hydrogen or fluorine, R.sup.1 is hydrogen, C.sub.1 C.sub.6 -alkyl, C.sub.5 - or C.sub.6 -cycloalkyl, (C.sub.1 -C.sub.4 -alkoxy)-C.sub.2 -C.sub.4 -alkyl or (C.sub.1 -C.sub.4 -alkylthio)-C.sub.2 -C.sub.4 -alkyl; W is a divalent radical --CH.dbd.CR.sup.2 --; --CH.dbd.CY--; --CH.dbd.CR.sup.2 --CH.sub.2 --; --CH.dbd.CR.sup.2 --CH.dbd.CR.sup.3 -- or ##STR2## where Y is chlorine or bromine and R.sup.2 and R.sup.3 are each hydrogen or C.sub.1 -C.sub.4 -alkyl, with the proviso that X is not F when W is --CH.dbd.CR.sup.2 --, their manufacture, and their use as herbicides.

DETAILED DESCRIPTION We claim: 1.
Phenylalkenylcarboxylic acid and esters thereof of the formula I ##STR35## where X is flourine; R.
sup.
1 is a member selected from the group consisting of methyl and ethyl; and W is --CH.
dbd.
CBr--.
2.
A herbicidal composition which comprises: an effective amount of a compound of the formula I as defined in claim 1 and a conventional formulating agent.
3.
A process for combating the growth of unwanted plants, which comprises: applying to said plants or their habitat an effective amount of a compound of the formula I as defined in claim 1.




Description:
The present invention relates to phenylalkenylcarboxylic acids which are substituted in the 5-position by tetrahydro-2H-isoindole-1,3-dione (tetrahydrophthalimide) and their esters, a process for their preparation and their use as herbicides.
It is known that certain isoindoledione-substituted cinnamates can be used as herbicides.
These compounds, which are disclosed in Japanese Preliminary Published Application 59/115 358, are of the general formula Z ##STR3## where Y is hydrogen or methyl and Q is alkyl, in particular ethyl.
Furthermore, European Laid-Open Application 68,822 discloses the structure Z.
sup.
1 : ##STR4## However, their herbicidal action and their toleration by crops are in no way satisfactory in practice.
It is an object of the present invention to provide herbicides which are better tolerated and at the same time more effective against weeds.
We have found that this object is achieved by the novel compounds of the general formula I ##STR5## where X is hydrogen or fluorine, R.
sup.
1 is hydrogen, C.
sub.
1 -C.
sub.
6 -alkyl, C.
sub.
5 - or C.
sub.
6 -cycloalkyl, (C.
sub.
1 -C.
sub.
4 -alkoxy)-C.
sub.
2 -C.
sub.
4 -alkyl or (C.
sub.
1 -C.
sub.
4 -alkylthio)-C.
sub.
2 -C.
sub.
4 -alkyl, W is a divalent radical --CH.
dbd.
CR.
sup.
2 --, --CH.
dbd.
CY--, --CH.
dbd.
CR.
sup.
2 --CH.
sub.
2 --, --CH.
dbd.
CR.
sup.
2 --CH.
dbd.
CR.
sup.
3 -- or ##STR6## where Y is chlorine or bromine and R.
sup.
2 and R.
sup.
3 are each hydrogen or C.
sub



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