N-ALKOXYAMIDES OF 6-(TRISUBSTITUTED PHENYL)-4-AMINOPICOLINATES AND THEIR USE AS SELECTIVE HERBICIDES FOR CROPS
First Claim
Patent Images
1. A compound of Formula I:
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whereinX represents CH, CF, or N;
Y represents halogen, C1-C8 alkyl, C3-C6 cycloalkyl, or phenyl substituted with 1-4 substituents independently selected from halogen, C1-C3 alkyl, C3-C6 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, cyano, nitro, N(R4)2, or where two adjacent substituents are taken together as —
OCH2O—
;
Z represents halogen, C1-C3 alkoxy, or C2-C4 alkenyl;
R1 represents H, C1-C3 alkyl, C2-C4 acyl, or benzyl;
R2 represents H, C1-C3 alkyl, or C2-C4 acyl;
R3 represents H, C1-C8 alkyl, C3-C8 cycloalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, alkylcarbonyl, alkylthio, alkylsulfonyl, C2-C8 alkenyl, C5-C8 cycloalkenyl, haloalkenyl, C2-C8 alkynyl, unsubstituted or substituted phenyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclyl, alkylcycloalkyl, alkylcycloalkenyl, unsubstituted or substituted arylalkyl, or R2 and R3 together with the O and N atoms to which they are joined form an unsubstituted or substituted 5- to 7-membered ring optionally containing one further heteroatom selected from O, N, and S; and
R4 represents H or C1-C3 alkyl.
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Abstract
N-Alkoxyamides of 4-aminopicolinic acids and 6-amino-4-pyrimidinecarboxylates are selective herbicides for corn, canola and sugar beet.
9 Citations
11 Claims
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1. A compound of Formula I:
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wherein X represents CH, CF, or N; Y represents halogen, C1-C8 alkyl, C3-C6 cycloalkyl, or phenyl substituted with 1-4 substituents independently selected from halogen, C1-C3 alkyl, C3-C6 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, cyano, nitro, N(R4)2, or where two adjacent substituents are taken together as —
OCH2O—
;Z represents halogen, C1-C3 alkoxy, or C2-C4 alkenyl; R1 represents H, C1-C3 alkyl, C2-C4 acyl, or benzyl; R2 represents H, C1-C3 alkyl, or C2-C4 acyl; R3 represents H, C1-C8 alkyl, C3-C8 cycloalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, alkylcarbonyl, alkylthio, alkylsulfonyl, C2-C8 alkenyl, C5-C8 cycloalkenyl, haloalkenyl, C2-C8 alkynyl, unsubstituted or substituted phenyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclyl, alkylcycloalkyl, alkylcycloalkenyl, unsubstituted or substituted arylalkyl, or R2 and R3 together with the O and N atoms to which they are joined form an unsubstituted or substituted 5- to 7-membered ring optionally containing one further heteroatom selected from O, N, and S; and R4 represents H or C1-C3 alkyl. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9)
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10. A process for making a compound of Formula I:
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wherein X represents CH, CF, or N; Y represents halogen, C1-C8 alkyl, C3-C6 cycloalkyl, or phenyl substituted with 1-4 substituents independently selected from halogen, C1-C3 alkyl, C3-C6 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, cyano, nitro, N(R4)2 or, where two adjacent substituents are taken together as —
OCH2O—
;Z represents halogen, C1-C3 alkoxy, or C2-C4 alkenyl; R1 represents H, C1-C3 alkyl, C2-C4 acyl, or benzyl; R2 represents H, C1-C3 alkyl, or C2-C4 acyl; R3 represents H, C1-C8 alkyl, C3-C8 cycloalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, alkylcarbonyl, alkylthio, alkylsulfonyl, C2-C8 alkenyl, C5-C8 cycloalkenyl, haloalkenyl, C2-C8 alkynyl, unsubstituted or substituted phenyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclyl, alkylcycloalkyl, alkylcycloalkenyl, unsubstituted or substituted arylalkyl, or R2 and R3 together with the O and N atoms to which they are joined form an unsubstituted or substituted 5- to 7-membered ring optionally containing one further heteroatom selected from O, N, and S; and R4 represents H or C1-C3 alkyl which comprises treating a compound of Formula II with an hydroxylamine NHR2OR3 or its conjugate acid, typically the hydrochloride salt, in the presence of a base wherein X, Y, Z, R1, R2, R3 and R4 are as previously defined.
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11. A process for making a compound of Formula I:
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wherein X represents CH, CF, or N; Y represents halogen, C1-C8 alkyl, C3-C6 cycloalkyl, or phenyl substituted with 1-4 substituents independently selected from halogen, C1-C3 alkyl, C3-C6 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, cyano, nitro, N(R4)2 or, where two adjacent substituents are taken together as —
OCH2O—
;Z represents halogen, C1-C3 alkoxy, or C2-C4 alkenyl; R1 represents H, C1-C3 alkyl, C2-C4 acyl, or benzyl; R2 represents H, C1-C3 alkyl, or C2-C4 acyl; R3 represents H, C1-C8 alkyl, C3-C8 cycloalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, alkylcarbonyl, alkylthio, alkylsulfonyl, C2-C8 alkenyl, C5-C8 cycloalkenyl, haloalkenyl, C2-C8 alkynyl, unsubstituted or substituted phenyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclyl, alkylcycloalkyl, alkylcycloalkenyl, unsubstituted or substituted arylalkyl, or R2 and R3 together with the O and N atoms to which they are joined form an unsubstituted or substituted 5- to 7-membered ring optionally containing one further heteroatom selected from O, N, and S; and R4 represents H or C1-C3 alkyl which comprises treating a compound of Formula III sequentially with an activating agent and an hydroxylamine NHR2OR3 or its conjugate acid, typically the hydrochloride salt, and, optionally, a base wherein X, Y, Z, R1, R2, R3 and R4 are as previously defined.
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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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InventorsEckelbarger, Joseph D., Schmitzer, Paul R., Boebel, Timothy A., Yerkes, Carla N., Satchivi, Norbert M., Whiteker, Gregory T.
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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 43/72 having rings with nitrogen ...A01N 43/78 1,3-Thiazoles; Hydrogenated...A01N 43/80 five-membered rings with on...A01N 43/82 five-membered rings with th...C07D 213/81 Amides; ImidesC07D 239/28 with hetero atoms or with c...C07D 239/30 Halogen atoms or nitro radi...C07D 239/42 One nitrogen atom nitro rad...C07D 239/47 One nitrogen atom and one o...C07D 405/12 linked by a chain containin...C07D 413/06 linked by a carbon chain co...C07D 413/12 linked by a chain containin...C07D 417/12 linked by a chain containin...
