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US 5,707,930 AGranted
4-cycloalkyl-5-substituted pyrimidine compounds useful as crop protection agents
AssigneeZeneca Limited
InventorsRaymond A. Felix, Hsiao-Ling M. Chin, Frank X. Woolard, David L. Lee, David B. Kanne
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Abstract
Herbicidal 4-cycloalkyl-5-substituted pyrimidine compounds of the formula ##STR1## are described. Herbicidal compositions containing such substituted-pyrimidinyl compounds and methods of controlling undesirable vegetation employing these compounds are also disclosed. The compounds in which XR, is hydroxyl are also useful as intermediates for producing the disclosed substituted-pyrimidinyl derivatives.
Claims19
A compound of the formula (I):
- ##STR37## wherein Z is independently halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, nitro, cyano, hydroxy, thiocyano, --N(R.sup.11)(R.sup.12), C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, (C.sub.1 -C.sub.6)alkoxy-(C.sub.1 -C.sub.6)alkyl, halo(C.sub.1 -C.sub.6)alkoxy-(C.sub.1 -C.sub.6)alkyl, --C(X)--R.sup.10 or --S(O).sub.k --R.sup.10 ;
- q is 0, 1, 2, 3, 4 or 5;
- A is C or N;
- X is oxygen or sulfur;
- R is hydrogen, hydrocarbyl, hydrocarbyl substituted with one or more of halogen or C.sub.1 -C.sub.6 alkoxy, pyridyl, substituted pyridyl, azabenzyl, pyrimidinyl, substituted pyrimidinyl or is of the formula --C(Y)--R.sup.6, --C(O)--C(O)--R.sup.6, --S(O).sub.2 --R.sup.6, --P(Y)(R.sup.11)(R.sup.12) or --Si(R.sup.13)(R.sup.14)(R.sup.15);
- wherein
- Y is oxygen or sulfur;
- R.sup.6 is hydrocarbyl, substituted hydrocarbyl, hydrocarbyloxy, substituted hydrocarbyloxy, hydrocarbyl-S--, substituted hydrocarbyl-S--, furyl or is of the formula --N(R.sup.7)(R.sup.8);
- wherein R.sup.7 and R.sup.8 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl, hydrocarbyloxy, substituted hydrocarbyloxy, pyridyl, furyl, thienyl, (C.sub.1 -C.sub.6)-alkoxycarbonyl(C.sub.1 -C.sub.6)alkyl, hydroxycarbonyl(C.sub.1 -C.sub.6)alkyl, or N(R.sup.9)(R.sup.10) wherein R.sup.9 and R.sup.10 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl or substituted phenyl;
- or R.sup.7 and R.sup.8 together with the nitrogen to which they are bound form an aziridine, piperazine, morpholine, thiomorpholine, thiomorpholine 1-oxide, thiomorpholine 1-1,dioxide, hexamethyleneimine, piperidine or pyrrolidine ring, any of which may be optionally substituted with C.sub.1 -C.sub.6 alkyl;
- R.sup.11 and R.sup.12 are each independently C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkylthio or C.sub.1 -C.sub.6 alkoxy;
- R.sup.13, R.sup.14 and R.sup.15 are each independently C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, aryl or arylalkyl;
- and
- k is 0, 1 or 2;
- Y.sub.1 is C.sub.3 -C.sub.6 cycloalkyl;
- Y.sup.2 is independently C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, mercapto, C.sub.1 -C.sub.6 alkylcarbamylthio, C.sub.1 -C.sub.6 haloalkoxy, nitro, cyano, hydroxy, thiocyano, (C.sub.1 -C.sub.6)-alkoxy-(C.sub.1 -C.sub.6)alkyl, --S(O).sub.k --R.sup.10 or --N(R.sup.11)(R.sup.12), wherein k, R.sup.10, R.sup.11 and R.sup.12 have the same meanings as above;
- n and m are each independently 0 or 1;
- and p is 0, 1, or 2;
- or an agriculturally acceptable salt thereof.
16 more elements
Dependencies are inferred from the claim text.