Alkyl sulphinyl and alkyl sulphonyl-1,2,4-thiadiazolyloxy acetam

Details Alkyl sulphinyl and alkyl sulphonyl-1,2,4-thiadiazolyloxy acetam Alkyl sulphinyl and alkyl sulphonyl-1,2,4-thiadiazolyloxy acetam

1996-10-25

1998-10-27

Gerstl, Robert

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

548129, 548130, C07D28508, A01N 43836

Patent

active

058278001

DESCRIPTION:

BRIEF SUMMARY
The invention relates to novel alkylsulphinyl- and alkylsulphonyl-1,2,4-thiadiazolyloxyacetamides, to processes and novel intermediates for their preparation and to their use as herbicides.
It has already been disclosed that certain alkylsulphinyl- and alkylsulphonyl-1,2,4-thiadiazolyloxyacetamides, for example N-isopropyl-.alpha.-(3-methylsulphinyl-1,2,4-thiadiazol-5-yl-oxy)-acetanil ide, exhibit herbicidal properties (cf., for example, EP-A 348 737 and the preceding, but not prepublished, Patent Application German Patent Specification 4 317 323 of 25.5.1993). However, the activity of these previously disclosed compounds is not completely satisfactory in all areas of application, particularly at low application rates and concentrations.
The novel alkylsulphinyl- and alkylsulphonyl-1,2,4-thiaazolyloxyacetamides of the general formula (I) have now been found, ##STR2## in which n represents the numbers 1 or 2, aralkyl which are in each case optionally substituted, aralkyl, aryl, alkoxy, alkenyloxy or alkinyloxy which are in each case optionally substituted, or bonded, form an optionally substituted, saturated or unsaturated nitrogen heterocycle which can contain additional heteroatoms and to which a benzo grouping can be fused, and optionally substituted, N-isopropyl-.alpha.-(3-methylsulphinyl-1,2,4-thiadiazol-5-yl-oxy)-acetanil ide, N-isopropyl-.alpha.-(3-methylsulphonyl-1,2,4-thiadiazol-5-yl-oxy)-acetanil ide, N-isopropyl-.alpha.-(3-ethylsulphinyl-1,2,4-thiadiazol-5-yl-oxy)-acetanili de, N-iso-propyl-.alpha.-(3 -ethylsulphonyl-1,2,4-thiadiazol-5-yl-oxy)-acetanilide, N-isopropyl-.alpha.-(3-propylsulphinyl-1,2,4-thiadiazol-5-yl-oxy)-acetanil ide, N-isopropyl-.alpha.-(3-propylsulphonyl-1,2,4-thiadiazol-5-yl-oxy)-acetanil ide--cf. EP-A 348 737--and also the compounds N-methyl-N-(4-fluoro-phenyl)-.alpha.-(3-methylsulphinyl-1,2,4-thiadiazol-5 -yl-oxy)-acetamide,N-methyl-N-(4-fluoro-phenyl)-.alpha.-(3-methylsulphonyl- 1,2,4-thiadiazol-5-yl-oxy)-acetamide,N-methyl-N-(4-fluoro-phenyl)-.alpha.-( 3-ethylsulphonyl-1,2,4-thiadiazol-5-yl-oxy)-acetamide,N-ethyl-N-(4-fluoro-p henyl)-.alpha.-(3-methylsulphinyl-1,2,4-thiadiazol-5-yl-oxy)-acetamide,N-et hyl-N-(4-fluoro-phenyl)-.alpha.-(3-methylsulphonyl-1,2,4-thiadiazol-5-yl-ox y)-acetamide and N-ethyl-N-(4-fluoro-phenyl)-.alpha.-(3-ethylsulphonyl-1,2,4-thiadiazol-5-y l-oxy)-acetamide--cf. German Patent Specification 4 317 323 of 25.5.1993--are excepted by disclaimer.
In addition, it has been found that the novel alkylsulphinyl- and alkylsulphonyl-1,2,4-thiadiazolyloxyacetamides of the general formula (I) are obtained if ##STR3## in which x represents halogen or the grouping --S(O).sub.n --R.sup.3, and ##STR4## in which R.sup.1 and R.sup.2 have the abovementioned meaning, presence of an acid-binding agent and where appropriate in the presence of a catalyst, or if general formula (IV) ##STR5## in which R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meaning, catalyst and where appropriate in the presence of a diluent.
Finally, it has been found that the novel alkylsulphinyl- and alkylsulphonyl-1,2,4-thiadiazolyloxyacetamides of the general formula (I) possess interesting herbicidal properties.
While in some cases exhibiting very good tolerability with regard to cultivated plants, for example cotton, the novel compounds of the formula (I) surprisngly exhibit a substantially more powerful effect against weeds which are difficult to control than does the chemically similar, known compound N-isopropyl-.alpha.-(3-methylsulphinyl-1,2,4-thiadiazol-5-yl-oxy)-acetanil ide.
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), represents C.sub.2 -C.sub.8 -alkenyl (which is optionally substituted by fluorine and/or chlorine), represents C.sub.2 -C.sub.8 -alkinyl or represents benzyl, 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), represents C.sub.2 -C.sub.8 -alkinyl, represents C.sub.3 -C.s

REFERENCES:
patent: 4645525 (1987-02-01), Forster
patent: 5090991 (1992-02-01), Forster

Affiliated with

Also associated with

Rating

Alkyl sulphinyl and alkyl sulphonyl-1,2,4-thiadiazolyloxy acetam does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Alkyl sulphinyl and alkyl sulphonyl-1,2,4-thiadiazolyloxy acetam, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Alkyl sulphinyl and alkyl sulphonyl-1,2,4-thiadiazolyloxy acetam will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1613749