Chemistry: fertilizers – Processes and products – Forms or conditioning
Patent
1988-09-06
1990-04-24
Rotman, Alan L.
Chemistry: fertilizers
Processes and products
Forms or conditioning
544 49, 71 88, A01N 4272, C07D27902
Patent
active
049197053
DESCRIPTION:
BRIEF SUMMARY
FIELD OF TECHNOLOGY
The present invention related to a novel trifluoromethanesulfonamide derivative, a method for the preparation thereof and a herbicide containing the same.
BACKGROUND TECHNOLOGY
It is known that benzylamine-type trifluoromethanesulfonamide derivatives such as N-benzyltrifluoromethanesulfonamide and the like and trifluoromethanesulfonamide derivatives having a condensed heterocyclic ring structure have herbicidal activity so that they are used as a herbicide.
These compounds, however, have no sufficiently high herbicidal activity against troublesome weeds and common weeds in upland field and, in addition, have a problem in respect of the phytotoxicity to crops.
A first object of the present invention is to provide a herbicide containing a novel trifluoromethanesulfonamide derivative as the active ingredient having, by solving the problem of the phytotoxicity to crops, sufficiently high herbicidal activity against weeds including purple nutsedge, i.e. Cyperus rotundus, and safety for crops in upland filed such as soybean, cotton, maize and the like.
A second object of the present invention is to provide the novel trifluoromethanesulfonamide derivative used as the active ingredient of the above mentioned herbicide and an efficient method for the preparation thereof.
DISCLOSURE OF THE INVENTION
The present invention provides:
(1) a trifluoromethanesulfonamide derivative represented by the general formula ##STR2## in which X is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a haloalkyl group having 1 to 4 carbon atoms, n is 1, 2 or 3, A is --O--CR.sup.3 R.sup.4 --, --S--CR.sup.3 R.sup.4 --, --SO--CR.sup.3 R.sup.4 --, --SO.sub.2 --CR.sup.3 R.sup.4 -- or --SO.sub.2 --NR.sup.3 --, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
(2) a method for the preparation of a trifluoromethanesulfonamide derivative represented by the general formula ##STR3## in which X, n, R.sup.1, R.sup.2 and A.sup.1 each have the same meaning as defined below, characterized by reacting an amine derivative represented by the general formula ##STR4## in which X is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a haloalkyl group having 1 to 4 carbon atoms, n is 1, 2 or 3, A.sup.1 is --O--CR.sup.3 R.sup.4 --, --S--CR.sup.3 R.sup.4 -- or --SO.sub.2 --NR.sup.3 -- and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a trifluoromethanesulfonyl halide or trifluoromethanesulfonic anhydride;
(3) a method for the preparation of a trifluoromethanesulfonamide derivative represented by the general formula ##STR5## in which X is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a haloalkyl group having 1 to 4 carbon atoms, n is 1, 2 or 3, A.sup.2 is --SO--CR.sup.3 R.sup.4 -- or --SO.sub.2 --CR.sup.3 R.sup.4 --, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, characterized by oxidizing a trifluoromethanesulfonamide derivative having a thiochroman ring represented by the general formula ##STR6## in which X is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a haloalkyl group having 1 to 4 carbon atoms, n is 1, 2 or 3 and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; and
(4) a herbicide containing a trifluoromethanesulfonamide derivative represented by the general formula ##STR7## in which X is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a haloalkyl group having 1 to 4 carbon atoms, n is 1, 2 or 3, A is --O--CR.sup.3 R.sup.4 --, --S--CR.sup.3 R.sup.4 --, -- SO--CR.sup.3 R.sup.4 --, --SO.sub.2 --CR.sup.3 R.sup.4 --or --SO.sub.2 --NR.sup.3 --, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
The trifluoromethanesulfonamide derivatives of the present invention are each a
REFERENCES:
patent: 3629332 (1971-12-01), Harrington et al.
patent: 4244960 (1981-01-01), Schroder et al.
Adachi Ryoichi
Hiramatsu Yoshiyuki
Mitsutake Kenichiro
Shibata Mitsuru
Howard Mary Sue
Idemitsu Kosan Company Limited
Rotman Alan L.
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