Sulfonated heterocyclic carboxamides and their use as herbicides

Details Sulfonated heterocyclic carboxamides and their use as herbicides Sulfonated heterocyclic carboxamides and their use as herbicides

1992-04-21

1994-06-28

Ford, John M.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504242, 504243, 544122, 544123, 544 82, 544 69, 544229, 544310, 544311, 544316, 544317, 544319, 544320, 544321, 544323, 544324, 544327, 544331, 544332, 544333, 544334, 544335, A01N 4354, C07D23926, C07D40112, C07D40114

Patent

active

053247108

DESCRIPTION:

BRIEF SUMMARY
It is already known that certain sulfonylated bi- or tricyclic heteroaromatic carboxamides have herbicidal and growth-regulatory properties (EP-A-244,166). Sulfonylated monocyclic pyridinecarboxamides have been described as fungicides and microbiocides [sic] in agriculture (Chem. Abstr. 108 (19): 167298p; Chem. Abstr. 108 (15): 131590p). A herbicidal action of these compounds has not been disclosed.
It has already been proposed to employ sulfonated 2-pyrimidinylcarboxamides [sic] and 2-triazinylcarboxamides as herbicides and growth regulators (see German Patent Application P 38 26 230.4 or EP-A-353,640).
It has now been fond that sulfonated 4-pyrimidinylcarboxamides have advantageous herbicidal, growth-regulatory and fungicidal properties.
The present invention relates to compounds of the formula I or their salts ##STR2## in which R.sup.1 is hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.2 -C.sub.6)alkenyl or (C.sub.2 -C.sub.6)-alkynyl -C.sub.3)-alkyl or phenyl; halogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy or (C.sub.1 -C.sub.6)alkylthio, where the three abovementioned radicals can be monosubstituted or polysubstituted by halogen or monosubstituted or disubstituted by (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio; --NR.sup.8 R.sup.9, (C.sub.3 -C.sub.6)-cycloalkyl, --OCHR.sup.8 CO.sub.2 R.sup.10, (C.sub.2 -C.sub.5)alkenyl, (C.sub.2 -C.sub.4)-alkynyl, (C.sub.3 -C.sub.5)alkenyloxy or (C.sub.3 -C.sub.5)alkynyloxy;
R.sup.6 is hydrogen, halogen, (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)alkoxy, --CN, --NO.sub.2, --CO--R.sup.11, --CO.sub.2 R.sup.12, (C.sub.1 -C.sub.3)alkylthio, --SO--R.sup.12, --SO.sub.2 --R.sup.12 or --CO--NR.sup.8 R.sup.9 ; or phenyl; together are --(CH.sub.2).sub.2 (CH.sub.2).sub.c (CH.sub.2).sub.2 -- or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --; (C.sub.2 -C.sub.4)alkenyl or R.sup.8 and R.sup.9 together are --(CH.sub.2).sub.2 (CH.sub.2).sub.c (CH.sub.2).sub.2 or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --; monosubstituted or polysubstituted by halogen or monosubstituted or disubstituted by CN, CO.sub.2 --R.sup.12, --NR.sup.8 R.sup.9, OR.sup.12 or Si(CH.sub.3).sub.3 ; (C.sub.3 -C.sub.4)alkynyl or (C.sub.3 -C.sub.4)--alkenyl, where the two abovementioned radicals are unsubstituted or substituted by CH.sub.3 or --Si(CH.sub.3).sub.3 ; (C.sub.3 -C.sub.6)cycloalkyl which is unsubstituted or substituted by (C.sub.1 -C.sub.4)alkyl or (C.sub.1 -C.sub.4)alkoxy; or Si(CH.sub.3).sub.3 ; which is monosubstituted or polysubstituted by halogen or (C.sub.1 -C.sub.3)alkoxy; (C.sub.3 -C.sub.6)cycloalkyl which is unsubstituted, or monosubstituted or polysubstituted by halogen, such as, for example, F, Cl and Br, or CH.sub.3, (C.sub.2 -C.sub.4)alkenyl or (C.sub.2 -C.sub.4)alkynyl; which can be condensed with an aromatic or non-aromatic 5- or 6-ring, the radical being unsubstituted or substituted, and
Of particular interest are compounds according to the invention of the formula (I) or their salts in which ##STR3## R.sup.13 is hydrogen, halogen, NO.sub.2, CN, (C.sub.1 -C.sub.4)alkyl which is unsubstituted, or monosubstituted or polysubstituted by halogen, such as, for example, F, Cl and Br, or monosubstituted by CN, OCH.sub.3 or SCH.sub.3 ; (C.sub.2 -C.sub.4)alkenyl which is unsubstituted, or monosubstituted or polysubstituted by halogen, such as, for example, F, Cl and Br, or monosubstituted by OCH.sub.3 ; (C.sub.2 -C.sub.4)alkynyl which is unsubstituted, or monosubstituted or polysubstituted by halogen, such as, for example, F, Cl and Br, or monosubstituted by OCH.sub.3 or Si(CH.sub.3).sub.3 ; (C.sub.3 -C.sub.6)cycloalkyl which is unsubstituted, or monosubstituted or polysubstituted by halogen, such as, for example, F and Cl, or CH.sub.3 ; --CO--R.sup.11, --OCH.sub.2 CH.sub.2 OR.sup.11, --OH, --C(R.sup.11)(OR.sup.17)(OR.sup.18); --CO.sub.2 R.sup.10, --CO--NR.sup.8 R.sup.9, --N.sub.3, --SO.sub.2 NR.sup.8 R.sup.9, --SO.sub.3 R.sup.19, --OSO.sub.2 R.sup.20 ; phenyl which is unsubstituted or monosubstituted or polysubstituted by halogen, such as, for example F, Cl and Br, CH.sub.3 or OCH.sub.3 ; --E--R.

REFERENCES:
patent: 2876224 (1959-03-01), Grant et al.

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