Heterocyclyl-1,3,4-thiadiazolyloxyacetamides and their use as he

Details Heterocyclyl-1,3,4-thiadiazolyloxyacetamides and their use as he Heterocyclyl-1,3,4-thiadiazolyloxyacetamides and their use as he

1996-10-04

1998-07-14

Gerstl, Robert

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

540603, 544134, 546165, 546269, 546277, 548136, C07D41704, A01L 43824

Patent

active

057803927

DESCRIPTION:

BRIEF SUMMARY
The invention relates to novel heterocyclyl- 1,3,4-thiadiazolyloxyacetamides, to a process and novel intermediates for their preparation and to their use as herbicides,
It is already known that certain thienyl-1,3,4-thiadiazolyloxyacetamides have herbicidal properties (cf. JP-A 05286969, cited in Chem. Abstracts 120: 245115). However, the efficacy of these known compounds is not completely satisfactory in all fields of application, in particular at low application rates and concentrations.
The novel heterocyclyl-1,3,4-thiadiazolyloxyacetamides of the general formula (I) have now been found, ##STR2## in which R.sup.1 represents hydrogen or in each case unsubstituted or substituted alkyl, alkenyl, alkinyl or aralkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkenyloxy or alkinyloxy, or form an unsubstituted or substituted, saturated or unsaturated nitrogen heterocycle which can contain other heteroatoms and to which a benzo grouping can be fused, and of thienyl.
It has further been found that the novel heterocyclyl-1,3,4-thiadiazolyloxyacetamides of the general formula (I) are obtained if alkylsulphonyl-1,3,4-thiadiazoles of the general formula (II) ##STR3## in which Het has the meaning given above and ##STR4## in which R.sup.1 and R.sup.2 have the meaning given above, acid acceptor and in the presence or absence of a catalyst.
Finally, it has been found that the novel heterocyclyl-1,3,4-thiadiazolyloxyacetamides of the general formula (I) have herbicidal properties of interest.
The invention preferably relates to compounds of the formula (I) in which substituted by fluorine, chlorine, cyano or C.sub.1 -C.sub.4 -alkoxy), C.sub.2 -C.sub.8 -alkenyl (which is optionally substituted by fluorine and/or chlorine), C.sub.2 -C.sub.8 -alkinyl or benzyl (which is optionally substituted by fluorine, chlorine, C.sub.1 -C.sub.4 -alkyl and/or C.sub.1 -C.sub.4 -alkoxy), by fluorine, chlorine, cyano or C.sub.1 -C.sub.4 -alkoxy), C.sub.2 -C.sub.8 -alkenyl (which is optionally substituted by fluorine and/or chlorine), C.sub.2 -C.sub.8 -alkinyl, C.sub.3 -C.sub.6 -cycloalkyl (which is optionally substituted by chlorine and/or C.sub.1 -C.sub.3 -alkyl), C.sub.5 - or C.sub.6 -cycloalkenyl, benzyl (which is optionally substituted by fluorine, chlorine, C.sub.1 -C.sub.4 -alkyl and/or C.sub.1 -C.sub.4 -alkoxy), phenyl (which is optionally substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl, C.sub.1 -C.sub.4 -alkoxy and/or C.sub.1 -C.sub.4 -alkylthio), C.sub.1 -Cg-alkoxy (which is optionally substituted by C.sub.1 -C.sub.4 -alkoxy), or C.sub.3 -C.sub.4 -alkenyloxy, or form a saturated or unsaturated five- to seven-membered nitrogen heterocycle which is optionally monosubstituted to trisubstituted by C.sub.1 -C.sub.3 -alkyl and can additionally contain oxygen and is optionally benzo-fused, and heterocyclyl having 2 to 8 carbon atoms and 1 to 4 heteroatoms - in particular nitrogen, oxygen and/or sulphur atoms, thienyl being excepted and the possible substituents preferably being selected from the following listing: halogen-substituted) C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl, C.sub.1 C.sub.4 -alkylsulphonyl, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxy-carbonyl.
The invention relates in particular to compounds of the formula (I) in which or s-pentyl (each of which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy), propenyl, butenyl, propinyl or butinyl, or s-pentyl, n-, i- or s-hexyl (each of which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy); propenyl, butenyl, pentenyl, propinyl, butinyl or pentinyl; cyclopentyl or cyclohexyl (each of which is optionally substituted by methyl and/or ethyl); cyclohexenyl; benzyl (which is optionally substituted by fluorine, chlorine and/or methyl); or phenyl (which is optionally substituted in each case by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, meth

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