Herbicidal substituted aryl-haloalkylpyrazoles
AssigneeMonsanto Company
InventorsScott S. Woodard, Bruce C. Hamper, Kurt Moedritzer, Michael D. Rogers, Deborah A. Mischke, Gerard A. Dutra
Life of this patent
Estimating the term…
Abstract
The invention herein relates to certain substituted-arylpyrazole compounds, herbicidal compositions containing same, herbicidal methods of use and processes for preparing said compounds.
Claims29
Compounds according to Formula I:
- ##STR95## and agriculturally acceptable salts and hydrates thereof wherein R.sub.1 is independently C.sub.1-8 alkyl;
- C.sub.3-8 cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl;
- C.sub.2-8 alkenyl or alkynyl;
- or benzyl;
- or said R.sub.1 members substituted with halogen, amino, nitro, cyano, hydroxy, alkoxy, alkylthio, ##STR96## YR.sub.10, or NR.sub.11 R.sub.12 ;
- R.sub.2 is C.sub.1-5 haloalkyl;
- R.sub.3 is halogen;
- R.sub.4 is an R.sub.1 member, alkylthio, alkoxyalkyl or polyalkoxyalkyl, carbamyl, halogen, amino, nitro, cyano, hydroxy, C.sub.3-10 heterocycle containing O, S(O).sub.m and/or NR.sub.18 hetero atoms, C.sub.6-12 aryl, aralkyl or alkaryl, ##STR97## YR.sub.15, or NR.sub.16 R.sub.17 ;
- X is O, S(O).sub.m , NR.sub.19 or CR.sub.20 R.sub.21 ;
- Y is O or S(O).sub.m or NR.sub.22 ;
- R.sub.8-17 and R.sub.19-22 are hydrogen or one of said R.sub.4 members;
- m is 0-2;
- and
- n is 1 to 5.
Compounds according to Formula II ##STR98## and agriculturally acceptable salts and hydrates thereof wherein R.sub.1 is C.sub.1-5 alkyl, alkylthio, alkoxyalkyl, C.sub.2-4 alkenyl, benzyl, which members may optionally be substituted with halogen, amino, nitro, cyano, hydroxy groups or ##STR99## R.sub.2, R.sub.3, X, Y, and R.sub.8 are as defined for Formula I;
- R.sub.5 is halogen or hydrogen;
- and
- R.sub.6 and R.sub.7 are independently an R.sub.4 member as defined for Formula I.
Compounds according to Formula III:
- ##STR100## and agriculturally acceptable salts and hydrates thereof wherein R.sub.1 is C.sub.1-5 alkyl;
- R.sub.2, R.sub.3, R.sub.10, and Y are as defined for Formula I;
- R.sub.5 and R.sub.7 are as defined for Formula II;
- and
- R.sub.6 is halogen, nitro, cyano, or YR.sub.10.
4-Chloro-3-(4-chloro-2-fluoro-5 -propargyloxyphenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole.
(2-Chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyraz ol-3-yl)-4-fluorophenoxy)acetic acid, 1-methylethyl ester.
2-Chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-py razol-3-yl)-4-fluorobenzoic acid, 2-methoxy-1-methyl-2-oxoethyl ester.
2-Chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)- 4-fluorobenzoic acid, 1methylethyl ester.
Herbicidal composition comprising an adjuvant and a herbicidally effective amount of a compound according to Formula I:
- ##STR102## and agriculturally acceptable salts and hydrates thereof wherein R.sub.1 is independently C.sub.1-8 alkyl;
- C.sub.3-8 cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl;
- C.sub.2-8 alkenyl or alkynyl;
- benzyl;
- or said R.sub.1 members substituted with halogen, amino, nitro, cyano, hydroxy, alkoxy, alkylthio, ##STR103## YR.sub.10, or NR.sub.11 R.sub.12 ;
- R.sub.2 is C.sub.1-5 haloalkyl;
- R.sub.3 is halogen;
- R.sub.4 is an R.sub.1 member, alkylthio, alkoxyalkyl or polyalkoxyalkyl, carbamyl, halogen, amino, nitro, cyano, hydroxy,C.sub.3-10 heterocycle containing O, S(O).sub.m and/or NR.sub.18 hetero atoms, C.sub.6-12 aryl, aralkyl or alkaryl, ##STR104## YR.sub.15, or NR.sub.16 R.sub.17 group;
- X is O, S(O).sub.m , NR.sub.19 or CR.sub.20 R.sub.14 ;
- Y is O or S(O).sub.m or NR.sub.22 ;
- R.sub.8-17 and R.sub.19-22 are hydrogen or one of said R.sub.4 members;
- m is 0-2;
- and
- n is 1 to 5.
Herbicidal composition comprising an adjuvant and a herbicidally effective amount of a compound according to Formula II:
- ##STR105## and agriculturally acceptable salts and hydrates thereof wherein R.sub.1 is C.sub.1-5 alkyl, alkylthio, alkoxyalkyl, C.sub.2-4 alkenyl, benzyl, which members may optionally be substituted with halogen, amino, nitro, cyano, hydroxy groups or ##STR106## R.sub.2, R.sub.3, X, Y, and R.sub.8 are as defined for Formula I;
- R.sub.5 is halogen or hydrogen;
- and
- R.sub.6 and R.sub.7 are independently an R.sub.4 member as defined for Formula I.
Herbicidal composition comprising an adjuvant and a herbicidally-effective amount of a compound according to Formula III:
- ##STR107## and agriculturally acceptable salts and hydrates thereof wherein R.sub.1 is C.sub.1-5 alkyl;
- R.sub.2, R.sub.3, R.sub.10, and Y are as defined for Formula I;
- R.sub.5 and R.sub.7 are as defined for Formula II;
- and
- R.sub.6 is halogen, nitro, cyano, or YR.sub.10.
Composition comprising an inert adjuvant and a herbicidally-effective amount of 4-Chloro-3-(4-chloro-2-fluoro-5-propargyloxyphenyl)-1-methyl-5-(trifluorom ethyl)-1H-pyrazole.
Composition comprising an inert adjuvant and a herbicidally-effective amount of (2-Chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluo ro-phenoxy)acetic acid, 1-methylethyl ester.
Composition comprising an inert adjuvant and a herbicidally-effective amount of 2-Chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluor obenzoic acid, 2-methoxy-1-methyl-2-oxoethyl ester.
Composition comprising an inert adjuvant and a herbicidally-effective amount of 2-Chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluor obenzoic acid, 1-methylethyl ester.
Method for combatting undesirable plants in crops which comprises applying to the locus thereof a herbicidally effective amount of a compound according to Formula I ##STR109## and agriculturally acceptable salts and hydrates thereof wherein R.sub.1 is independently C.sub.1-8 alkyl;
- C.sub.3-8 cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl;
- C.sub.2-8 alkenyl or alkynyl;
- benzyl;
- or said R.sub.1 members substituted with halogen, amino, nitro, cyano, hydroxy, alkoxy, alkylthio, ##STR110## YR.sub.10, or NR.sub.11 R.sub.12 ;
- R.sub.2 is C.sub.1-5 haloalkyl;
- R.sub.3 is halogen;
- R.sub.4 is an R.sub.1 member, thioalkyl, alkoxyalkyl or polyalkoxyalkyl, carbamyl, halogen, amino, nitro, cyano, hydroxy, C.sub.3-10 heterocycle containing O, S(O).sub.m and/or NR.sub.18 hetero atoms, C.sub.6-12 aryl, aralkyl or alkaryl, ##STR111## YR.sub.15, or NR.sub.16 R.sub.17 group;
- X is 0, S(O).sub.m , NR.sub.19 or CR.sub.20 R.sub.21 ;
- Y is 0 or S(O).sub.m or NR.sub.22 ;
- R.sub.8-17 and R.sub.19-22 are hydrogen or one of said R.sub.4 members;
- m is 0-2;
- and
- n is 1 to 5.
Method for combatting undesirable plants in crops which comprises applying to the locus thereof a herbicidally effective amount of a compound according to Formula II ##STR112## and agriculturally acceptable salts and hydrates thereof wherein R.sub.1 is C.sub.1-5 alkyl, alkylthio, alkoxyalkyl, C.sub.2-4 alkenyl, benzyl, which members may optionally be substituted with halogen, amino, nitro, cyano, hydroxy groups or ##STR113## R.sub.2, R.sub.3, X, Y, and R.sub.8 are as defined for Formula I;
- R.sub.5 is halogen or hydrogen;
- and
- R.sub.6 and R.sub.7 are independently an R.sub.4 member as defined for Formula I.
Method for combatting undesirable plants in crops which comprises applying to the locus thereof a herbicidally effective amount of a compound according to Formula III:
- ##STR114## and agriculturally acceptable salts and hydrates thereof wherein R.sub.1 is C.sub.1-5 alkyl;
- R.sub.2, R.sub.3, R.sub.10, and Y are as defined for Formula I;
- R.sub.5 and R.sub.7 are as defined for Formula II;
- and
- R.sub.6 is halogen, nitro, cyano, or YR.sub.10.
Dependencies are inferred from the claim text.