6-aryl-4-aminopicolinates and their use as herbicides
First Claim
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1. A compound of the formula I whereinX represents H, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, aryloxy, nitro, C1-C6 haloalkyl, C1-C6 haloalkoxy, thiocyanide, or cyano;
- Y represents an aryl group selected from the group consisting of a phenyl, indanyl or naphthyl or a heteroaryl group selected from the group of 5- or 6-membered heteroaromatic rings containing one or more heteroatoms which may be fused to other aromatic systems, the aryl or heteroaryl group being unsubstituted or substituted with one or more substituents selected from halogen, hydroxy, nitro, cyano, aryloxy, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, halogenated C1-C6 alkyl, halogenated C1-C6 alkoxy, C1-C6 acyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, aryl, C1-C6 OC(O)alkyl, C1-C6 NHC(O)alkyl, C(O)OH, C1-C6 C(O)alkyl, C(O)NH2, C1-C6 C(O)NHalkyl, C1-C6 C(O)N(alkyl)2, —
OCH2CH2—
, —
OCH2CH2CH2—
, —
OCH2O—
or —
OCH2CH2O—
;
Z represents halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, aryloxy, nitro, C1-C6 haloalkyl, C1-C6 haloalkoxy, thiocyanide, or cyano; and
W represents —
NO2, —
N3, —
NR1R2, —
N═
CR3R4 or —
NHN═
CR3R4 wherein R1 and R2 independently represent H, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, aryl, heteroaryl, 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 R1 and R2 taken together with N represent a 5- or 6-membered saturated or unsaturated ring which may contain additional O, S or N heteroatoms; and
R3 and R4 independently represent H, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, aryl or heteroaryl or R3 and R4 taken together with ═
C represent a 5- or 6-membered saturated ring; and
agriculturally acceptable derivatives of the carboxylic acid group.
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Abstract
4-Aminopicolinic acids having aryl or heteroaryl substituents in the 6-position and their amine and acid derivatives are potent herbicides demonstrating a broad spectrum of weed control.
76 Citations
10 Claims
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1. A compound of the formula I
wherein X represents H, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, aryloxy, nitro, C1-C6 haloalkyl, C1-C6 haloalkoxy, thiocyanide, or cyano; -
Y represents an aryl group selected from the group consisting of a phenyl, indanyl or naphthyl or a heteroaryl group selected from the group of 5- or 6-membered heteroaromatic rings containing one or more heteroatoms which may be fused to other aromatic systems, the aryl or heteroaryl group being unsubstituted or substituted with one or more substituents selected from halogen, hydroxy, nitro, cyano, aryloxy, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, halogenated C1-C6 alkyl, halogenated C1-C6 alkoxy, C1-C6 acyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, aryl, C1-C6 OC(O)alkyl, C1-C6 NHC(O)alkyl, C(O)OH, C1-C6 C(O)alkyl, C(O)NH2, C1-C6 C(O)NHalkyl, C1-C6 C(O)N(alkyl)2, —
OCH2CH2—
, —
OCH2CH2CH2—
, —
OCH2O—
or —
OCH2CH2O—
;
Z represents halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, aryloxy, nitro, C1-C6 haloalkyl, C1-C6 haloalkoxy, thiocyanide, or cyano; and
W represents —
NO2, —
N3, —
NR1R2, —
N═
CR3R4 or —
NHN═
CR3R4 whereinR1 and R2 independently represent H, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, aryl, heteroaryl, 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 R1 and R2 taken together with N represent a 5- or 6-membered saturated or unsaturated ring which may contain additional O, S or N heteroatoms; and
R3 and R4 independently represent H, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, aryl or heteroaryl or R3 and R4 taken together with ═
C represent a 5- or 6-membered saturated ring; and
agriculturally acceptable derivatives of the carboxylic acid group. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10)
the heteroaryl group being unsubstituted or substituted with one or more halogen, C1-C2 alkyl or C1-C2 haloalkyl groups. -
4. The compounds of claim 1 in which Y represents a phenyl group unsubstituted or substituted with one or more halogen, C1-C2 alkyl or C1-C2 haloalkyl groups.
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5. The compounds of claim 4 in which Y represents a para-substituted phenyl group.
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6. The compound of claim 1 in which Z represents Cl.
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7. The compound of claim 1 in which W represents NR1R2 where R1 and R2 independently represent H or C1-C6 alkyl.
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8. The compound of claim 1 in which X represents H or F, Y represents a phenyl group unsubstituted or substituted with one or more halogen, C1-C2 alkyl or C1-C2 haloalkyl groups, Z represents Cl and W represents NR1R2 where R1 and R2 independently represent H or C1-C6 alkyl.
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9. A herbicidal composition comprising a herbicidally effective amount of a compound of Formula I, as claimed in any of claims 1 to 8, in admixture with an agriculturally acceptable adjuvant or carrier.
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10. A method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil to control the emergence of vegetation an herbicidally effective amount of a compound of Formula I, as claimed in any of claims 1 to 8.
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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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InventorsBryan, Kristy, Brewster, William Kirkland, Lowe, Christian Thomas, Balko, Terry William, Webster, Jeffery Dale, Ruiz, James Melvin, Fields, Stephen Craig, Irvine, Nicholas Martin, Buysse, Ann Marie, Lo, William Chi-Leung, Gast, Roger Eugene, Weimer, Monte Ray, Epp, Jeffrey Brian, Keese, Renee Joan, Richburg, John Sanders III, Green, Renard Antonio
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Primary Examiner(s)PRYOR, ALTON NATHANIEL
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Application NumberUS10/209,448Publication NumberTime in Patent Office763 DaysField of Search504/244, 504/251, 504/252, 504/254, 504/255, 504/260, 546/250, 546/268.1, 546/268.4, 546/280.4, 546/281.7, 546/283.4, 546/255US Class Current504/244CPC Class CodesA01N 43/40 six-membered ringsA01N 43/78 1,3-Thiazoles; Hydrogenated...C07D 213/79 Acids; EstersC07D 213/81 Amides; ImidesC07D 401/04 directly linked by a ring-m...C07D 405/04 directly linked by a ring-m...C07D 405/06 linked by a carbon chain co...C07D 409/04 directly linked by a ring-m...C07D 413/04 directly linked by a ring-m...C07D 417/04 directly linked by a ring-m...
