2-SUBSTITUTED-6-AMINO-5-ALKYL, ALKENYL OR ALKYNYL-4-PYRIMIDINECARBOXYLIC ACIDS AND 6-SUBSTITUTED-4-AMINO-3-ALKYL, ALKENYL OR ALKYNYL PICOLINIC ACIDS AND THEIR USE AS HERBICIDES
First Claim
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1. A compound of the formula I whereinR1 represents C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkoxyalkyl, C2-C4 alkythioalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkoxyalkenyl, C2-C4 thioalkylalkenyl, C2-C4 alkynyl or C2-C4 haloalkynyl, formyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl;
- R2 represents C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl or
whereinW1 represents H or halogen;
X1 represents H, halogen, nitro, cyano, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C2-C4 alkoxyalkyl, C2-C6 alkylcarbonyl, C1-C6 alkythio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C4 alkenyloxy, C2-C4 alkynloxy, C2-C4 alkenylthio, C2-C4 alkynylthio, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C1-C6 haloalkoxy, C2-C4 haloalkoxyalkyl, C2-C6 haloalkyl-carbonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 halo-alkylsulfonyl, C3-C6 trialkylsilyl, C2-C4 haloalkenyloxy, C2-C4 haloalkynyloxy, C2-C4 haloalkenylthio, C2-C4 haloalkynylthio, —
C(O)OR7, —
C(O)NR6R7, —
CR6NOR7, —
NR6R7, —
NR6OR7, —
NR6SO2R7, —
NR6C(O)R7, —
NR6C(O)OR7, —
NR6C(O)NR6R7 or —
NCR6NR6R7;
Y1 represents H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl or C2-C6 haloalkenyl, or, when X1 and Y1 are taken together, represents —
O(CH2)nCH2—
, or —
O(CH2)nO—
wherein n=1 or 2; and
Z1 represents H or halogen;
R3 and R4 independently represent H, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, hydroxy, C1-C6 alkoxy, amino, C1-C6 acyl, C1-C6 carboalkoxy, C1-C6 alkylcarbamyl, C1-C6 alkylsulfonyl, C1-C6 trialkylsilyl or C1-C6 dialkyl phosphonyl or R3 and R4 taken together with N represent a 5- or 6-membered saturated ring; and
R6 represents H, C1-C4 alkyl or C1-C4 haloalkyl; and
R7 represents C1-C4 alkyl or C1-C4 haloalkyl;
and agriculturally acceptable derivatives of the carboxylic acid group.
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Abstract
6-Amino-4-pyrimidinecarboxylic acids having alkyl, alkenyl or alkynyl substituents in the 5-position and 4-aminopicolinic acids having alkyl, alkenyl or alkynyl substituents in the 3-position, and their amine and acid derivatives, are potent herbicides demonstrating a broad spectrum of weed control.
14 Citations
11 Claims
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1. A compound of the formula I
wherein R1 represents C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkoxyalkyl, C2-C4 alkythioalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkoxyalkenyl, C2-C4 thioalkylalkenyl, C2-C4 alkynyl or C2-C4 haloalkynyl, formyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl; -
R2 represents C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl or wherein W1 represents H or halogen; X1 represents H, halogen, nitro, cyano, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C2-C4 alkoxyalkyl, C2-C6 alkylcarbonyl, C1-C6 alkythio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C4 alkenyloxy, C2-C4 alkynloxy, C2-C4 alkenylthio, C2-C4 alkynylthio, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C1-C6 haloalkoxy, C2-C4 haloalkoxyalkyl, C2-C6 haloalkyl-carbonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 halo-alkylsulfonyl, C3-C6 trialkylsilyl, C2-C4 haloalkenyloxy, C2-C4 haloalkynyloxy, C2-C4 haloalkenylthio, C2-C4 haloalkynylthio, —
C(O)OR7, —
C(O)NR6R7, —
CR6NOR7, —
NR6R7, —
NR6OR7, —
NR6SO2R7, —
NR6C(O)R7, —
NR6C(O)OR7, —
NR6C(O)NR6R7 or —
NCR6NR6R7;Y1 represents H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl or C2-C6 haloalkenyl, or, when X1 and Y1 are taken together, represents —
O(CH2)nCH2—
, or —
O(CH2)nO—
wherein n=1 or 2; andZ1 represents H or halogen; R3 and R4 independently represent H, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, hydroxy, C1-C6 alkoxy, amino, C1-C6 acyl, C1-C6 carboalkoxy, C1-C6 alkylcarbamyl, C1-C6 alkylsulfonyl, C1-C6 trialkylsilyl or C1-C6 dialkyl phosphonyl or R3 and R4 taken together with N represent a 5- or 6-membered saturated ring; and R6 represents H, C1-C4 alkyl or C1-C4 haloalkyl; and R7 represents C1-C4 alkyl or C1-C4 haloalkyl; and agriculturally acceptable derivatives of the carboxylic acid group. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 10, 11)
wherein W1 represents H or halogen; X1 represents H, halogen, nitro, cyano, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C2-C4 alkoxyalkyl, C2-C6 alkylcarbonyl, C1-C6 alkythio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C4 alkenyloxy, C2-C4 alkynloxy, C2-C4 alkenylthio, C2-C4 alkynylthio, C1-C6 haloalkyl, C2-C6 halo-alkenyl, C2-C6 haloalkynyl, C1-C6 haloalkoxy, C2-C4 haloalkoxyalkyl, C2-C6 haloalkyl-carbonyl, C1-C6 haloalkythio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C3-C6 trialkylsilyl, C2-C4 haloalkenyloxy, C2-C4 haloalkynyloxy, C2-C4 haloalkenylthio, C2-C4 haloalkynylthio, —
C(O)OR7, —
C(O)NR6R7, —
CR6NOR7, —
NR6R7, —
NR6OR7, —
NR6SO2R7, —
NR6C(O)R7, —
NR6C(O)OR7, —
NR6C(O)NR6R7 or —
NCR6NR6R7;Y1 represents H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl or C2-C6 haloalkenyl, or, when X1 and Y1 are taken together, represents —
O(CH2)nCH2—
, or —
O(CH2)nO—
wherein n=1 or 2; andZ1 represents H or halogen; R6 represents H, C1-C4 alkyl or C1-C4 haloalkyl; and R7 represents C1-C4 alkyl or C1-C4 haloalkyl.
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8. A compound of claim 7 in which W1 represents H or F, X1 represents H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or —
- NR6R7, Y1 represents Cl or halomethyl, and Z1 represents H or F.
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10. An herbicidal composition comprising an herbicidally effective amount of a compound according to claim 1, in a mixture with an agriculturally acceptable adjuvant or carrier.
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11. A method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil or irrigation water to prevent the emergence of vegetation an herbicidally effective amount of a compound according to claim 1.
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9. A compound having the formula
in which W1 represents H or F; -
X1 represents H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or —
NR6R7;Y1 represents Cl or halomethyl; Z1 represents H or F; and agriculturally acceptable derivatives of the carboxylic acid group.
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Specification
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Current AssigneeCorteva Agriscience LLC (Corteva, Inc.)
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Original AssigneeDow Agrosciences LLC (Corteva, Inc.)
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InventorsRuiz, James M., Lo, William C., Schmitzer, Paul R., Epp, Jeffrey B., Yerkes, Carla N., Siddall, Thomas L., Balko, Terry W.
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Granted Patent
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Time in Patent OfficeDays
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Field of Search
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US Class Current504/239
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CPC Class CodesA01N 43/40 six-membered ringsA01N 43/54 1,3-Diazines; Hydrogenated ...A01N 47/18 containing a —O—CO—N< group...C07D 213/79 Acids; EstersC07D 239/42 One nitrogen atom nitro rad...
