Difluoromethanesulfonyl anilide derivatives useful as herbicides
View Patent ↗Novel difluoromethanesulfonamide derivatives of the formula (I) Difluoromethanesulfonamide derivatives represented by the formula wherein X represents halogen, Y represents CH or N, R 1 represents hydrogen, and R 2 represents hydrogen or hydroxy, or R 1 and R 2 together may form C═O with the carbon atom to which they are bonded, and their use as herbicide for paddy field weeds.
1. A compound of the formula (I)
wherein
X represents halogen,
Y represents N,
R 1 represents hydrogen, and
R 2 represents hydrogen or hydroxy, or
R 1 and R 2 together with the carbon atom to which they are attached form C═O.
2. A compound according to claim 1 , wherein
X represents fluorine or chlorine,
Y represents N,
R 1 represents hydrogen, and
R 2 represents hydrogen or hydroxy, or
R 1 and R 2 together with the carbon atom to which they are attached form C═O.
3. A process for preparing a compound of the formula (I) according to claim 1 ,
wherein
X, Y, R 1 and R 2 are defined as in claim 1 , comprising,
a) reacting a compound of the formula (II)
wherein
X, Y, R 1 and R 2 have the same definition as aforementioned,
with difluoromethanesulfonyl chloride in the presence of an inert solvent, and optionally, in the presence of an acid binding agent,
or
b) when R 1 and R 2 together form C═O with the carbon atom to which they are attached:
reacting a compound of the formula (Ib)
wherein
X and Y have the same definition as aforementioned,
with an oxidizing agent in the presence of an inert solvent, and optionally, in the presence of an acid catalyst,
or
c) when R 1 represents hydrogen, and R 2 represents hydroxy:
reacting a compound of the formula (Ic)
wherein
X and Y have the same definition as aforementioned,
with an alkali metal hydride complex compound or a borane complex in the presence of an inert solvent.
4. A herbicidal composition comprising at least one compound of the formula (I) according to claim 1 .
5. A process for combating paddy field weeds, comprising, contacting a paddy field weed or its habitat with at least one compound of the formula (I) according to claim 1 .
6. A process for the preparation of a herbicidal composition, comprising, mixing a compound of the formula (I) according to claim 1 with one or more extenders, one or more surface active agents, or a combination thereof.
7. A compound according to claim 1 , wherein
X represents fluorine,
Y represents N,
R 1 represents hydrogen, and
R 2 represents hydroxy.