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US 5,668,088 AGranted
Herbicidal substituted 3-aryl-pyrazoles
AssigneeMonsanto Company
InventorsBruce C. Hamper, Lisa L. Mc Dermott
Life of this patent
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Abstract
The invention herein relates to certain substituted-arylpyrazole compounds, herbicidal compositions containing same, herbicidal methods of use and processes for preparing said compounds.
Claims12
A compound according to Formula I:
- ##STR13## 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 cycloalkylalkyl;
- C.sub.2-8 alkenyl or alkynyl;
- benzyl;
- or said R.sub.1 members substituted with halogen, amino, nitro, cyano, hydroxy, C.sub.1-8 alkoxy, C.sub.1-8 alkylthio, --C(.dbd.X)YR.sub.8, --C(.dbd.X)R.sub.9, YR.sub.10, or NR.sub.11 R.sub.12 ;
- R.sub.2 is C.sub.1-6 haloalkyl;
- R.sub.3 is C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, CHO or CH.sub.2 OH;
- R.sub.4 members are independently an R.sub.1 member, C.sub.1-8 thioalkyl, C.sub.1-8 polyalkoxyalkyl, carbamyl, halogen, amino, nitro, cyano, hydroxy, C.sub.6-2 aryl, aralkyl or alkaryl, --C(X)YR.sub.13, --C(X)R.sub.14, YR.sub.15, or NR.sub.16 R.sub.17 group;
- or two R.sub.4 groups may be combined through a saturated and/or unsaturated carbon, or --(C.dbd.X)--, linkage to form a cyclic ring having up to 9 ring members which may be substituted with an R.sub.1 member, halogen, amino, nitro, cyano, hydroxy, C.sub.6-12 aryl, aralkyl, alkaryl, --C(.dbd.X)YR.sub.13, --C(.dbd.X)R.sub.14, 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, S(O).sub.m or NR.sub.22 ;
- wherein at least one R.sub.4 member is a non-halogen;
- R.sub.8-22 are hydrogen, C.sub.1-8 alkyl, C.sub.3-8 cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkylalkyl, C.sub.2-8 alkenyl or alkynyl, benzyl, or said R.sub.1 members substituted with halogen, amino, nitro, cyano, hydroxy, C.sub.1-8 alkoxy, C.sub.1-8 alkylthio, C.sub.6-2 aryl, aralkyl, alkaryl, carboxyl, alkoxy C.sub.1-8 -alkyl, C.sub.1-8 alkylamino, di-C.sub.1-8 -alkylamino, C.sub.1-8 alkoxy, or carbamyl;
- m is 0-2 and
- n is 1-5.
12 more elements
Herbicidal composition comprising an adjuvant and a herbicidally-effective amount of a compound according to Formula I:
- ##STR17## 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, C.sub.1-8 alkoxy, C.sub.1-8 alkylthio, --C(.dbd.X)YR.sub.8, --C(.dbd.X)R.sub.9, YR.sub.10, or NR.sub.11 R.sub.12 ;
- R.sub.12 is C.sub.1-6 haloalkyl;
- R.sub.3 is C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, CHO or CH.sub.2 OH;
- R.sub.4 members are independently an R.sub.1 member, C.sub.1-8 thioalkyl, C.sub.1-8 polyalkoxyalkyl, carbamyl, halogen, amino, nitro, cyano, hydroxy, C.sub.6.sub.2-12 aryl, aralkyl or alkaryl, --C(X)YR.sub.13, --C(X)R.sub.14, YR.sub.15, or NR.sub.16 R.sub.17 group;
- or two R.sub.4 groups may be combined through a saturated and/or unsaturated carbon, or --(C.dbd.X)--, linkage to form a cyclic ring having up to 9 ring members which may be substituted with an R.sub.1 member, halogen, amino, nitro, cyano, hydroxy, C.sub.6-12 aryl, aralkyl, alkaryl, --C(.dbd.X)YR.sub.13, --C(.dbd.X)R.sub.14, 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, S(O).sub.m or NR.sub.22 ;
- wherein at least one R.sub.4 member is a non-halogen:
- R.sub.8-22 are hydrogen, 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, C.sub.1-8 alkoxy, C.sub.1-8 alkylthio, C.sub.6-12 aryl, aralkyl, alkaryl, carboxyl, alkoxy-C.sub.1-8 -alkyl, C.sub.1-8 alkylamino, di-C.sub.1-8 -alkylamino, C.sub.1-8 alkoxy, or carbamyl;
- m is 0-2 and
- n is 1-5.
12 more elements
Method for combatting undesirable plants in crops comprising applying to the locus thereof a herbicidally-effective amount of a compound according to Formula I:
- ##STR21## 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, C.sub.1-8 alkoxy, C.sub.1-8 alkylthio, --C(.dbd.X)YR.sub.8, --C(.dbd.X)R.sub.9, YR.sub.10, or NR.sub.11 R.sub.12 ;
- R.sub.2 is C.sub.1-6 haloalkyl;
- R.sub.3 is C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, CHO or CH.sub.2 OH;
- R.sub.4 members are independently an R.sub.1 member, C.sub.1-8 thioalkyl, C.sub.1-8 polyalkoxyalkyl, carbamyl, halogen, amino, nitro, cyano, hydroxy, C.sub.6-12 aryl, aralkyl or alkaryl, --C(X)YR.sub.13, --C(X)R.sub.14, YR.sub.15, or NR.sub.16 R.sub.17 group;
- or two R.sub.4 groups may be combined through a saturated and/or unsaturated carbon, or --(C.dbd.X)--, linkage to form a cyclic ring having up to 9 ring members which may be substituted with an R.sub.1 member, halogen, amino, nitro, cyano, hydroxy, C.sub.6-12 aryl, aralkyl, alkaryl, --C(.dbd.X)YR.sub.13, --C(.dbd.X)R.sub.14, 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, S(O).sub.m or NR.sub.22 ;
- wherein at least one R.sub.4 member is a non-halogen;
- R.sub.8-22 are hydrogen, C.sub.1-8 alkyl, C.sub.3-8 cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenyl alkyl, C.sub.2-8 alkenyl or alkynyl, benzyl, or said R.sub.1 members substituted with halogen, amino, nitro, cyano, hydroxy, C.sub.1-8 alkoxy, C.sub.1-8 alkylthio, C.sub.6-12 aryl, aralkyl, alkaryl, carboxyl, alkoxy-C.sub.1-8 -alkyl, C.sub.1-8 alkylamino, di-C.sub.1-8 -alkylamino, C.sub.1-8 alkoxy, or carbamyl;
- m is 0-2 and
- n is 1-5.
12 more elements
Dependencies are inferred from the claim text.