Novel 4-amino-6-(pyridyl and 2-substitutedphenyl)-picolinates and 6-amino-2-(pyridyl and 2-substitutedphenyl)-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′, wherein R1′ is H, C1-C8 alkyl, or C7-C10 arylalkyl;
• 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 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 independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, 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 alkyl)sulfonyl, tri(C1-C6 alkyl)silyl, di(C1-C6 alkyl)phosphonyl, or R3 and R4 taken 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 independently hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 alkoxy or C1-C6 alkylamino, or, R3′ and R4′ taken together with the carbon atom to which they are attached form a 5- or 6-membered saturated ring;
• Ar is selected from the group consisting of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6
• wherein
• W1 is F;
• W2 is hydrogen or F;
• W3 is Cl, Br, I, 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, or C1-C4 haloalkylthio;
• X1 is hydrogen, F, Cl, Br, I, C1-C4 alkyl, C1-C4 haloalkyl, cyclopropyl, halocyclopropyl, C1-C4 alkoxy, or C1-C4 haloalkoxy;
• X2 is hydrogen, F, Cl, Br, I, C1-C4 alkyl, C1-C4 haloalkyl, cyclopropyl, halocyclopropyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, CN, CONH2, CO2H, or NO2;
• X3 is F, Cl, Br, I, C1-C4 alkyl, C1-C4 haloalkyl, cyclopropyl, halocyclopropyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, CN, CONH2, CO2H, or NO2;
• Y1 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, C1-C4 haloalkylamino, (C1-C6 alkoxy)-substituted C1-C6 alkyl, CN, or NO2;
• Y2 is hydrogen or F;
• Z1 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, cyclopropyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, or C1-C4 haloalkylthio;
• Z2 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, cyclopropyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, or C1-C4 haloalkylthio;
• Z3 is Cl, Br, I, C1-C4 alkyl, C1-C4 haloalkyl, cyclopropyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, or C1-C4 haloalkylthio;
• Z4 is C1-C4 alkyl, C1-C4 haloalkyl, cyclopropyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, or C1-C4 haloalkylthio;
• and
• wherein when Ar is:
• then X is N, CH, CF, CCl, or CCH3;
• with the provisos that:
• i) X1 is not hydrogen, F, Cl, or OCH3 when R2 is Cl or vinyl and X is N;
• ii) X1 is not hydrogen, Cl or OCH3 when R2 is Cl and X is CH;
• iii) X1 is not Cl when R2 is Cl and X is CF;
• and
• iv) X1 is not CF3, cyclopropyl, or OCH3 when R2 is OCH3 and X is CF;
• then X is N, CH, or CF;
• with the proviso that X1 is not hydrogen, CH3, or OCH3 when R2 is Cl and X is N;
• then X is N, CH, or CF;
• then X is N, CH, or CF;
• then X is N, CH, or CF;
• and
• then X is N, CH, or CF;
• with the proviso that W3 is not Cl, CH3, CF3 or OCH3 when Y2 is hydrogen;
• or an N-oxide or agriculturally acceptable salt thereof.