Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1997-09-05
1999-01-12
Richter, Johann
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504167, 504170, 504262, 504287, 504290, 548134, 548136, A01N 4382, C07D28513
Patent
active
058589228
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP96/00836 filed on Mar. 1, 1996.
The invention relates to novel fluorothiadiazolyloxyacetamides, to a process and novel intermediates for their preparation and to their use as herbicides.
It is already known that certain chlorothiadiazolyloxyacetamides such as, for example, the compound N-methyl-N-phenyl-2-(3-chloro-1,2,4-thiadiazol-5-yl-oxy)-acetamide have herbicidal properties (cf. EP-A 300344). However, the activity of these prior-art compounds is not entirely satisfactory in all areas of application, in particular at low application rates and concentrations.
This invention, accordingly, provides the novel fluorothiadiazolyloxyacetamides of the general formula (I) ##STR2## in which R.sup.1 represents hydrogen or respectively optionally substituted alkyl, alkenyl, alkynyl or arylalkyl, alkenyl, alkenyloxy, alkynyl, cycloalkyl, cycloalkenyl, aryl, arylalkyl or arylalkyloxy, or to form an optionally substituted saturated or unsaturated nitrogen heterocycle which may contain further hetero atoms and to which a benzo grouping may be fused, and
Additionally, it has been found that the novel fluorothiadiazolyloxyacetamides of the general formula (I) are obtained when ##STR3## in which R.sup.3 is as defined above and ##STR4## in which R.sup.1 and R.sup.2 are each as defined above, of an acid binder and if appropriate in the presence of a catalyst.
Finally, it has been found that the novel fluorothiadiazolyloxyacetamides of the general formula (I) have interesting herbicidal properties.
Surprisingly, the fluorothiadiazolyloxyacetamides of the general formula (I) according to the invention combine partly good crop plant compatibility with a significantly stronger herbicidal activity than the compound N-methyl-N-phenyl-2-(3-chloro-1,2,4-thiadiazol-5-yl-oxy)-acetamide known from the prior art.
The present invention preferably provides compounds of the formula (I) in which substituted by fluorine, chlorine, cyano or C.sub.1 -C.sub.4 -alkoxy), or C.sub.2 -C.sub.8 -alkenyl (which is optionally substituted by fluorine and/or chlorine), or C.sub.2 -C.sub.8 -alkynyl 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), or C.sub.2 -C.sub.8 -alkynyl, or C.sub.3 -C.sub.6 -cycloalkyl (which is optionally substituted by chlorine and/or C.sub.1 -C.sub.3 -alkyl), or C5- or C.sub.6 -cycloalkenyl, or benzyl (which is optionally substituted by fluorine, chlorine, C.sub.1 -C.sub.4 -alkyl and/or C.sub.1 -C.sub.4.sub.4 -alkoxy), or 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), or C.sub.1 -C.sub.8 -alkoxy (which is optionally substituted by C.sub.1 -C.sub.4 -alkoxy), or C.sub.3 -C.sub.4 -alkenyloxy or benzyloxy, or to form a saturated or unsaturated five- to seven-membered nitrogen heterocycle which is optionally mono- to trisubstituted by C.sub.1 -C.sub.3 -alkyl and which is optionally benzo-fused, and 2-fluoro-1,3,4-thiadiazol-5-yl.
The invention in particular provides compounds of the formula (I) in which or s-pentyl (each of which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy), or propenyl, butenyl, propynyl or butynyl, or s-pentyl, n-, i- or s-hexyl (each of which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy), or propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl, or cyclopentyl or cyclohexyl (each of which is optionally substituted by methyl and/or ethyl), or cyclohexenyl, or benzyl (which is optionally substituted by fluorine, chlorine and/or methyl) or phenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy or ethoxy), or methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, n-, i- or s-pentyloxy (
REFERENCES:
patent: 5096483 (1992-03-01), Forster et al.
C.A. 111:39374k, vol. 111 (1989) p. 603 (Abstract).
Bertsch Achim
Bohm Stefan
Diehr Hans-Joachim
Dollinger Markus
Forster Heinz
Bayer Aktiengesellschaft
Richter Johann
Sackey Ebenezier
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