Pyrimidinyloxy benzene derivatives as herbicides
Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, wherein Q, Z, R 2 , R 3 and m are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.
1. A method for preparing a compound of Formula 1,
wherein
Q is
r is 1;
Z is 0;
R 1 is halogen, or C 1 -C 4 haloalkyl;
R 2 is halogen;
m is 0, 1 or 2;
each R 3 is independently halogen;
each R 3 is attached to the remainder of Formula 1 at the 3-, 4- or 6-position;
comprising heating a compound of Formula 2
wherein
Q is
r is 1;
Z is 0;
R A is H;
R 1 is halogen or C 1 -C 4 haloalkyl;
each R 3 is independently halogen;
each R 3 is attached to the remainder of Formula 2 at the 3-, 4- or 6-position;
with a compound of Formula 3
wherein
LG comprises a halogen or SO 2 CH 3 ; and
R 2 is halogen;
in the presence of a base in a suitable solvent.
2. The method of claim 1 wherein in the compound of Formula 1
R 2 is F, Cl or Br;
m is 0 or 1; and
each R 3 is attached to the remainder of Formula 1 at the 3- or 4-position;
and in the compound of Formula 2
m is 0 or 1; and
each R 3 is attached to the remainder of Formula 1 at the 3- or 4-position and in the compound of Formula 3
R 2 is F, Cl, or Br.
3. The method of claim 2 wherein in the compound of Formula 3 LG is halogen.
4. The method of claim 2 wherein in the compound of Formula 3 LG is SO 2 CH 3 .
5. The method of claim 1 wherein in the compound of Formula 3
LG is halogen.
6. The method of claim 1 wherein in the compound of Formula 3 LG is SO 2 CH 3 .
7. The method of claim 1 wherein the compound of Formula 1 is selected from the group consisting of
2-[2-(3-bromo-5-isoxazolyl)phenoxyl]-5-chloropyrimidine,
5-chloro-2-[2-]3-(difluoromethyl)-5-isoxazolyl]phenoxy]pyrimidine,
5-chloro-2-[2-[3-(trifluoromethyl)-5-isoxazolyl]phenoxy]pyrimidine,
5-chloro-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3-fluorophenoxy]pyrimidine,
5-bromo-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3-fluorophenoxy]pyrimidine,
5-chloro-2-[2-[3-(trifluoromethyl)-5-isoxazolyl]-3-chlorophenoxy]pyrimidine,
5-chloro-2-[2-[3-(trifluoromethyl)-5-isoxazolyl]-3-fluorophenoxy]pyrimidine,
5-chloro-242-[3-(difluoromethyl)-5-isoxazolyl]-3-chlorophenoxy]pyrimidine,
5-bromo-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3-chlorophenoxy]pyrimidine,
5-bromo-2-[2-[3-(trifluoromethyl)-5-isoxazolyl]-3-chlorophenoxy]pyrimidine, and
5-chloro-242-[3-(difluoromethyl)-5-isoxazolyl]-3-bromophenoxy]pyrimidine.
8. A compound that is 3-difluoromethyl-5-(2-fluoro-6-methoxyphenyl)isoxazole.
9. A compound that is 2-(3-difluoromethyl-5-isoxazolyl)-3-fluorophenol.