Imidazo[1,2-a]pyrimidine sulfonic acids and acid halides
AssigneeThe Dow Chemical Company
InventorsNorman R. Pearson, William A. Kleschick, Shannon L. Bartley
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Abstract
Novel substituted imidazolo[1,2-a]pyrimidine-2-sulfonanilides are prepared from novel substituted imidazolo[1,2-a]pyrimidine-2-sulfonic acids by conversion to the corresponding sulfonyl halides and condensation with substituted anilines and by other methods. N-(2,6-difluorophenyl)-3-chloro-4,6-dimethylimidazolo[1,2-a]pyrimidine-2-s ulfonamide is typical of the compounds prepared. The compounds are useful general and selective pre- and post-emergence herbicides.
Claims13
An imidazolo[1,2-a]pyrimidine-2-sulfonyl halide compound of the formula ##STR36## wherein X and Z each, independently represents R, OR.sup.3, SR.sup.3, NR.sup.1 R.sup.2, F, Cl, Br, or CN;
- Y represents R, OR.sup.3, F, Cl, Br, or CN;
- W represents R, OR, SO.sub.n R.sup.3, NR.sup.1 R.sup.2, F, Cl, Br, NO.sub.2, CN, C(O)E, or phenyl, phenoxy, or phenylthio, each phenyl optionally having 1 to 3 substituents selected from the group consisting of F, Cl, Br, CN, CF.sub.3, NO.sub.2, and CH.sub.3 ;
- G represents Cl or Br;
- R represents H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl;
- R.sup.1 and R.sup.2 each, independently represents H or C.sub.1 -C.sub.4 alkyl;
- R.sup.3 represents C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl;
- E represents R, OR, SR, NR.sup.1 R.sup.2, or phenyl;
- and
- n represents an integer of 0, 1, or 2.
A compound according to claim 64 wherein X and Z each, independently represents H, F, Cl, Br, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 alkylthio.
An imidazolo[1,2-a]pyrimidine-2-sulfonic acid compound of the formula ##STR37## wherein X and Z each, independently represents R, OR.sup.3, SR.sup.3, NR.sup.1 R.sup.2, F, Cl, Br, or CN;
- Y represents R, OR.sup.3, F, Cl, Br, or CN;
- W represents R, OR, SO.sub.n R.sup.3, NR.sup.1 R.sup.2, F, Cl, Br, NO.sub.2, CN, C(O)E, or phenyl, phenoxy, or phenylthio, each phenyl optionally having 1 to 3 substituents selected from the group consisting of F, Cl, Br, CN, CF.sub.3, NO.sub.2, and CH.sub.3 ;
- R represents H, C.sub.1 -C.sub.4 alkyl, or C.sub.1 -C.sub.4 haloalkyl;
- R.sup.1 and R.sup.2 each, independently represents H or C.sub.1 -C.sub.4 alkyl;
- R.sup.3 represents C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl;
- E represents R, OR, SR, NR.sup.1 R.sup.2, or phenyl;
- n represents an integer of 0, 1, or 2;
- and
- alkali metal and amine salts thereof.
Dependencies are inferred from the claim text.