Back to results
US 5,308,826 AGranted
Herbicidal 4-substituted pyridyl-3-carbinols
AssigneeZeneca Limited
InventorsHsiao-Ling M. Chin, Yi Q. Wei, Nhan H. Nguyen
Life of this patent
Estimating the term…
Abstract
4-substituted pyridyl-3-carbinols of the formula ##STR1## wherein R is hydrogen, or an acyl, alkyl or carbamyl group exhibit desirable preemergent and postemergent herbicidal activity. Also disclosed are herbicidal compositions comprising such compounds and; a method of controlling undesirable vegetation employing such compounds. The compounds wherein AR is hydroxyl serve as useful intermediates for the production of the alpha-benzyl substituted compounds as well as exhibiting herbicidal activity.
Claims51
A compound of the formula ##STR136## wherein R.sup.1 and R.sup.5 are each independently halogen, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkyl, 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, --S(O).sub.m --R.sup.10, cyano, --OH, thiocyano, nitro or --N(R.sup.11)(R.sup.12);
- R.sup.2, R.sup.3 and R.sup.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, nitro, halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 haloalkyl or --S(O).sub.m --R.sup.10 ;
- R.sup.6, R.sup.7, and R.sup.8 are each independently hydrogen, halogen, C.sub.1-C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkynyl, nitro, --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, cyano, --C(X)--R.sup.10 or --S(O).sub.m --R.sup.10 ;
- R.sup.9 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, 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, --S(O).sub.m --R.sup.10, cyano, hydroxy, thiocyano, nitro or --N(R.sup.11)(R.sup.12);
- A is oxygen or sulfur;
- n is 0 or 1;
- R is hydrogen, hydrocarbyl, hydrocarbyl substituted with one or more of halogen or C.sub.1 -C.sub.6 alkoxy or is of the formula --C(X)--R.sup.10, --C(O)--C(O)--R.sup.10, --S(O).sub.2 --R.sup.10 or --P(X)(R.sup.15)(R.sup.16);
- wherein:
- X is O or S;
- R.sup.10 is hydrocarbyl, substituted hydrocarbyl, hydrocarbyloxy, substituted hydrocarbyloxy, hydrocarbyl-S--, substituted hydrocarbyl-S-- or is of the formula --N(R.sup.11)(R.sup.12);
- wherein R.sup.11 and R.sup.12 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.13)(R.sup.14) wherein R.sup.13 and R.sup.14 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl;
- or R.sup.11 and R.sup.12 together with the nitrogen to which they are bound form an aziridine, piperazine, morpholine, thiomorpholine, thiomorpholine sulfinyl, thiomorpholine sulfonyl, hexamethyleneimine, piperidine or pyrrolidine ring, any of which may be optionally substituted with C.sub.1 -C.sub.6 alkyl;
- R.sup.15 and R.sup.16 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;
- and
- m is 0, 1 or 2;
- with the proviso that when R.sup.1 is chloro or fluoro;
- R.sup.5 is hydrogen, chloro, fluoro or methoxy;
- and R.sup.2, R.sup.3, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are hydrogen;
- R is not hydrogen;
- and agriculturally acceptable salts thereof.
16 more elements
A herbicidal composition comprising
- (A) a compound of the formula:
- ##STR145## wherein:
- R.sup.1 and R.sup.5 are each independently halogen, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkyl, 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, --S(O).sub.m --R.sup.10, cyano, --OH, thiocyano, nitro or --N(R.sup.11)(R.sup.12);
- R.sup.2, R.sup.3 and R.sup.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, nitro, halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 haloalkyl or --S(O).sub.m --R.sup.10 ;
- R.sup.6, R.sup.7, and R.sup.8 are each independently hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkynyl, nitro, --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, cyano, --C(X)--R.sup.10 or --S(O).sub.m --R.sup.10 ;
- R.sup.9 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, 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, --S(O).sub.m --R.sup.10, cyano, hydroxy, thiocyano, nitro or --N(R.sup.11)(R.sup.12);
- A is oxygen or sulfur;
- n is 0 or 1;
- R is hydrogen, hydrocarbyl, hydrocarbyl substituted with one or more of halogen or C.sub.1 -C.sub.6 alkoxy or is of the formula --C(X)--R.sup.10, --C(O)--C(O)--R.sup.10, --S(O).sub.2 --R.sup.10 or --P(X)(R.sup.15)(R.sup.16);
- wherein:
- X is O or S;
- R.sup.10 is hydrocarbyl, substituted hydrocarbyl, hydrocarbyloxy, substituted hydrocarbyloxy, hydrocarbyl-S--, substituted hydrocarbyl-S-- or is of the formula --N(R.sup.11)(R.sup.12);
- wherein R.sup.11 and R.sup.12 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.13)(R.sup.14) wherein R.sup.13 and R.sup.14 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl;
- or R.sup.11 and R.sup.12 together with the nitrogen to which they are bound form an aziridine, piperazine, morpholine, thiomorpholine, thiomorpholine sulfinyl, thiomorpholine sulfonyl, hexamethyleneimine, piperidine or pyrrolidine ring, any of which may be optionally substituted with C.sub.1 -C.sub.6 alkyl;
- R.sup.15 and R.sup.16 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;
- and
- m is 0, 1 or 2;
- and agriculturally acceptable salts thereof;
- and
- (B) a carrier therefor.
19 more elements
A method for controlling undesirable vegetation comprising applying to the area where control is desired an herbicidally effective amount of a compound of the formula:
- ##STR154## wherein:
- R.sup.1 and R.sup.5 are each independently halogen, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkyl, 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, --S(O).sub.m --R.sup.10, cyano, --OH, thiocyano, nitro or --N(R.sup.11)(R.sup.12);
- R.sup.2, R.sup.3 and R.sup.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, nitro, halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 haloalkyl or --S(O).sub.m --R.sup.10 ;
- R.sup.6, R.sup.7, and R.sup.8 are each independently hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkynyl, nitro, --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, cyano, --C(X)--R.sup.10 or --S(O).sub.m --R.sup.10 ;
- R.sup.9 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, 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, --S(O).sub.m --R.sup.10, cyano, hydroxy, thiocyano, nitro or --N(R.sup.11)(R.sup.12);
- A is oxygen or sulfur;
- n is 0 or 1;
- R is hydrogen, hydrocarbyl, hydrocarbyl substituted with one or more of halogen or C.sub.1 -C.sub.6 alkoxy or is of the formula --C(X)--R.sup.10, --C(O)--C(O)--R.sup.10, --S(O).sub.2 --R.sup.10 or --P(X)(R.sup.15)(R.sup.16);
- wherein:
- X is O or S;
- R.sup.10 is hydrocarbyl, substituted hydrocarbyl, hydrocarbyloxy, substituted hydrocarbyloxy, hydrocarbyl-S--, substituted hydrocarbyl-S-- or is of the formula --N(R.sup.11)(R.sup.12);
- wherein R.sup.11 and R.sup.12 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.13)(R.sup.14) where R.sup.13 and R.sup.14 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl;
- or R.sup.11 and R.sup.12 together with the nitrogen to which they are bound form an aziridine, piperazine, morpholine, thiomorpholine, thiomorpholine sulfinyl, thiomorpholine sulfonyl, hexamethyleneimine, piperidine or pyrrolidine ring, any of which may be optionally substituted with C.sub.1 -C.sub.6 alkyl;
- R.sup.15 and R.sup.16 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;
- and
- m is 0, 1 or 2;
- and agriculturally acceptable salts thereof.
14 more elements
A compound of the formula ##STR163## wherein R.sup.1 and R.sup.5 are each independently halogen, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkyl, 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, --S(O).sub.m --R.sup.10, cyano, --OH, thiocyano, nitro or --N(R.sup.11)(R.sup.12);
- R.sup.2, R.sup.3 and R.sup.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, nitro, halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 haloalkyl or --S(O).sub.m --R.sup.10 ;
- R.sup.6, R.sup.7, and R.sup.8 are each independently hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkynyl, nitro, --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, cyano, --C(X)--R.sup.10 or --S(O).sub.m --R.sup.10 ;
- R.sup.9 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, 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, --S(O).sub.m --R.sup.10, cyano, hydroxy, thiocyano, nitro or --N(R.sup.11)(R.sup.12);
- A is oxygen or sulfur;
- n is 0 or 1;
- R.sup.10 is hydrocarbyl, substituted hydrocarbyl, hydrocarbyloxy, substituted hydrocarbyloxy, hydrocarbyl-S--, substituted hydrocarbyl-S-- or is of the formula --N(R.sup.11)(R.sup.12);
- wherein R.sup.11 and R.sup.12 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.13)(R.sup.14) wherein R.sup.13 and R.sup.14 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl;
- or R.sup.11 and R.sup.12 together with the nitrogen to which they are bound form an aziridine, piperazine, morpholine, thiomorpholine, thiomorpholine sulfinyl, thiomorpholine sulfonyl, hexamethyleneimine, piperidine or pyrrolidine ring, any of which may be optionally substituted with C.sub.1 -C.sub.6 alkyl;
- R.sup.15 and R.sup.16 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;
- and
- m is 0, 1 or 2;
- with the proviso that when R.sup.5 is hydrogen, chloro, fluoro or methoxy;
- and R.sup.2, R.sup.3, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are hydrogen;
- R.sup.1 is not chloro or fluoro;
- and agriculturally acceptable salts thereof.
12 more elements
Dependencies are inferred from the claim text.