4-amino-6-(4-substituted-phenyl)-picolinates and 6-amino-2-(4-substituted-phenyl)-pyrimidine-4-carboxylates and their use as herbicides

A compound of Formula (I):

• wherein
• X is N or CY;
• wherein Y is hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, or C1-C3 haloalkylthio;
• R1 is OR1′ or NR1″R2″;
• wherein R1′ is H, C1-C8 alkyl, or C7-C10 arylalkyl;
• and R1″ and R2″ are each independently hydrogen, C1-C12 alkyl, C3-C12 alkenyl, or C3-C12 alkynyl;
• R2 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, amino, C1-C4 alkylamino, C2-C4 haloalkylamino, formyl, (C1-C3 alkyl)carbonyl, (C1-C3 haloalkyl)carbonyl, cyano, or a group of the formula —CR17═CR18—SiR19R20R21;
• wherein R17 is hydrogen, F, or Cl;
• R18 is hydrogen, F, Cl, C1-C4 alkyl, or C1-C4 haloalkyl;
• and R19, R20, and R21 are each independently C1-C10 alkyl, C3-C6 cycloalkyl, C1-C10 haloalkyl, C3-C6 halocycloalkyl, phenyl, substituted phenyl, C1-C10 alkoxy, or OH;
• R3 and R4 are each independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, hydroxy, C1-C6 alkoxy, C1-C6 haloalkoxy, formyl, (C1-C3 alkyl)carbonyl, (C1-C3 haloalkyl)carbonyl, (C1-C6 alkoxy)carbonyl, (C1-C6 alkyl)carbamyl, C1-C6 alkylsulfonyl, tri(C1-C6 alkyl)silyl, di(C1-C6 alkyl)phosphonyl, or R3 and R4 together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated ring, or R3 and R4 taken together represent ═CR3′R4′, wherein R3′ and R4′ are each independently hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 alkoxy, or C1-C6 alkylamino, or R3′ and R4′ together with the carbon atom to which they are attached form a 5- or 6-membered saturated ring;
• Ar is Ar1, Ar2, Ar3, Ar4, Ar5, or Ar6:
• wherein
• X1 is H, F, Br, I, ethynyl, CF2H, OCF2H, OCF3, CN, CONH2, CO2H, CO2CH3, or NO2;
• X2 is H, F, Cl, Br, I, ethynyl, CH3, CFH2, CF2H, CF3, OCF2H, OCF3, CN, CONH2, CO2H, or NO2;
• X3 is H, F, Br, I, ethynyl, CH3, CFH2, CF2H, CF3, OCF2H, OCF3, CN, CONH2, CO2H, or NO2;
• wherein
• a) when Ar is
• then X is N, CH, CF, CO, or CCH3;
• with provisos that:
• v) R2 is not Cl or vinyl, when X is N;
• vi) X1 is not H, F, OCF3, or CN, when R2 is CI and X is CH;
• vii) X1 is not F, I, CN, or ethynyl, when R2 is OCH3 and X is CF;
• viii) X1 is not H, when X is CCl;
• and
• b) when Ar is
• then X is N, CH, CF, CCl, or CCH3;
• with provisos that:
• v) R2 is not Cl, when X is N;
• vi) X2 is not Cl, when R2 is OCH3 or vinyl and X is N;
• vii) X2 is not Cl, when R2 is Cl and X is CH;
• viii) X2 is not Cl, Br, I, or CF3, when R2 is OCH3 and X is CF;
• and
• c) when Ar is
• then X is N, CH, or CF;
• with provisos that:
• v) R2 is not Cl, when X is N;
• vi) X3 is not CH3, when R2 is OCH3 and X is N;
• vii) X3 is not H, F, or CH3, when R2 is Cl and X is CH;
• viii) X3 is not Br or I, when R2 is OCH3 and X is CF;
• and
• d) when Ar is
• then X is N, CH, or CF;
• with provisos that:
• v) R2 is not Cl, when X is N;
• vi) X2 is not Cl, when R2 is OCH3 or vinyl and X is N;
• vii) X2 is not F, when R2 is Cl and X is CH;
• viii) X2 is not Cl, Br, I, or CF3, when R2 is OCH3 and X is CF;
• e) when Ar is
• then X is N, CH, or CF;
• with proviso that:
• iii) X3 is not CH3, when R2 is Cl and X is N;
• iv) X3 is not Br or I, when X is CF and R2 is OCH3;
• and
• f) when Ar is
• then X is N, CH, or CF;
• or an N-oxide or agriculturally acceptable salt thereof.