N-alkoxyamides of 6-(substituted phenyl)-4-aminopicolinates and 2-(substituted phenyl)-6-amino-4-pyrimidinecarboxylates and their use as selective herbicides for crops

1. An herbicidal composition comprising an herbicidally effective amount of a compound of Formula I,

wherein

X represents CH, CF, or N;

Y represents phenyl substituted with 1-4 substituents independently selected from halogen, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, cyano, nitro, N(R 4 ) 2 , or where two adjacent substituents are taken together as —OCH 2 O—;

Z represents halogen, C 1 -C 3 alkoxy, or C 2 -C 4 alkenyl;

R 1 represents H, C 1 -C 3 alkyl, C 2 -C 4 acyl, or benzyl;

R 2 represents H, C 1 -C 3 alkyl, or C 2 -C 4 acyl;

R 3 represents H, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, alkylcarbonyl, alkylthio, alkylsulfonyl, C 2 -C 8 alkenyl, C 5 -C 8 cycloalkenyl, haloalkenyl, C 2 -C 8 alkynyl, unsubstituted or substituted phenyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclyl, alkylcycloalkyl, alkylcycloalkenyl, unsubstituted or substituted arylalkyl, or R 2 and R 3 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

R 4 represents H or C 1 -C 3 alkyl;

or a salt thereof; in a mixture with an agriculturally acceptable adjuvant or carrier.

2. A method for postemergent control of undesirable vegetation which comprises applying to said undesirable vegetation an herbicidally effective amount of a compound of Formula I,

wherein

X represents CH, CF, or N;

Y represents phenyl substituted with 1-4 substituents independently selected from halogen, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, cyano, nitro, N(R 4 ) 2 , or where two adjacent substituents are taken together as —OCH 2 O—;

Z represents halogen, C 1 -C 3 alkoxy, or C 2 -C 4 alkenyl;

R 1 represents H, C 1 -C 3 alkyl, C 2 -C 4 acyl, or benzyl;

R 2 represents H, C 1 -C 3 alkyl, or C 2 -C 4 acyl;

R 3 represents H, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, alkylcarbonyl, alkylthio, alkylsulfonyl, C 2 -C 8 alkenyl, C 5 -C 8 cycloalkenyl, haloalkenyl, C 2 -C 8 alkynyl, unsubstituted or substituted phenyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclyl, alkylcycloalkyl, alkylcycloalkenyl, unsubstituted or substituted arylalkyl, or R 2 and R 3 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

R 4 represents H or C 1 -C 3 alkyl;

or a salt thereof;

or an herbicidal composition thereof.

3. The method of claim 2 wherein the compound of Formula I is applied to said undesirable vegetation in the presence of corn; said undesirable vegetation comprises lambsquarters ( Chenopodium album ), velvetleaf ( Abutilon theophrasti ), wild buckwheat ( Polygonum convululus ), sicklepod ( Casia obtusifolia ), or pigweed, redroot ( Amaranthus retroflexus ).

4. The method of claim 3 wherein the compound of Formula I is selected from the group consisting of:

4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(2-methylpropoxy)picolinamide (Compound 1),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-methoxypicolinamide (Compound 2),

N-(2-Propenyloxy)-4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinamide (Compound 3),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-ethoxypicolinamide (Compound 4),

4-Amino-N-(benzyloxy)-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinamide (Compound 5),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-methoxy-N-methyl-picolinamide (Compound 6),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-propoxypicolinamide (Compound 7),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-isopropoxypicolinamide (Compound 8),

N-Acetyl-N-(2-propenyloxy)-6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinylpyrimidine-4-carboxamide (Compound 9),

N-(2-Propenyloxy)-6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinylpyrimidine-4-carboxamide (Compound 10),

N-(2-Propenyloxy)-6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxamide (Compound 11),

4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(tetrahydro-2H-pyran-2-yloxy)picolinamide (Compound 12),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(2-propynyloxy)picolinamide (Compound 13),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(4-methyl-benzyloxy)picolinamide (Compound 14),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(4-chloro-benzyloxy)picolinamide (Compound 15),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-((2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)tetrahydro-2H-pyran-2-yloxy)picolinamide (Compound 16),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(tetrahydrofuran-2-yloxy)picolinamide (Compound 17),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(cyclohex-2-enyl-oxy)picolinamide (Compound 18),

2-(4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinamidooxy)acetic acid (Compound 19),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-phenoxypicolinamide (Compound 20),

4-Amino-N-tert-butoxy-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinamide (Compound 21),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(4-fluoro-benzyloxy)picolinamide (Compound 22),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(4-methoxy-benzyloxy)picolinamide (Compound 23),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-hydroxy-N-methylpicolinamide (Compound 24),

N-(2-Propenyloxy)-6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxamide (Compound 25),

N-(2-Propenyloxy)-4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-methylpicolinamide (Compound 26),

N-(2-Propenyloxy)-4-amino-3,6-dichloropicolinamide (Compound 27),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(2-methyl-2-propenyl-oxy)picolinamide (Compound 28),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(2-chloro-2-propenyl-oxy)picolinamide (Compound 29),

(E)-4-Amino-N-(2-butenyloxy)-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)picolinamide (Compound 30),

(E)-4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(3-chloro-2-propenyl-oxy)picolinamide (Compound 31),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(cyclopropyl-methoxy)picolinamide (Compound 32),

4-Amino-N-(but-3-en-2-yloxy)-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)picolinamide (Compound 33),

4-Amino-3,6-dichloro-N-(4-fluorobenzyloxy)picolinamide (Compound 34),

N-(2-Propenyloxy)-6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methoxypyrimidine-4-carboxamide (Compound 35),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(thiazol-5-yl-methoxy)picolinamide (Compound 36),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(2-fluoro-2-propenyl-oxy)picolinamide (Compound 37),

4-Amino-N-(3-butenyloxy)-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinamide (Compound 38),

N-(2-Propenyloxy)-4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinamide (Compound 39),

(4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridin-2-yl)(isoxazolidin-2-yl)methanone (Compound 40),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-((2-chlorothiazol-5-yl)-methoxy)picolinamide (Compound 41),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(furan-2-yl-methoxy)picolinamide (Compound 42),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(furan-3-yl-methoxy)picolinamide (Compound 43),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(cyclohexenyl-methoxy)picolinamide (Compound 44),

(E)-4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(2-pentenyl-oxy)picolinamide (Compound 45),

4-Amino-N-butoxy-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinamide (Compound 46),

4-Amino-3-chloro-N-((5-chloro-1,2,3-thiadiazol-4-yl)methoxy)-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinamide (Compound 47),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-N-(tetrahydro-2H-pyran-2-yloxy)picolinamide (Compound 48),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(2-methoxy-ethoxy)picolinamide (Compound 49),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(2-cyanoethoxy)picolinamide (Compound 50),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-((2-methoxyethoxy)-methoxy)picolinamide (Compound 51),

(4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridin-2-yl)(3,6-dihydro-2H-1,2-oxazin-2-yl)methanone (Compound 52),

N-(2-Propenyloxy)-4-amino-3-chloro-6-(4-methylphenyl)picolinamide (Compound 53),

N-(2-Propenyloxy)-4-amino-3-chloro-6-(benzo[d][1,3]dioxol-5-yl)-3-chloropicolinamide (Compound 54),

N-(2-Propenyloxy)-4-amino-3-chloro-6-(4-fluorophenyl)picolinamide (Compound 55),

N-(2-Propenyloxy)-4-amino-3-chloro-6-(4-cyanophenyl)picolinamide (Compound 56),

4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-hydroxypicolinamide (Compound 57),

6-Amino-2-(4-chloro-2,3-difluorophenyl)-N-hydroxy-5-methoxypyrimidine-4-carboxamide (Compound 58), and

sodium 2-propenyloxy(4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinoyl)amide (Compound 59).

5. The method of claim 2 wherein the compound of Formula I is applied to said undesirable vegetation in the presence of sugar beet; said undesirable vegetation comprises lambsquarters ( Chenopodium album ) or purple deadnettle ( Lamium purpureum ).

6. The method of claim 5 wherein the compound of Formula I is selected from the group consisting of

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-methoxypicolinamide (Compound 2),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-ethoxypicolinamide (Compound 4),

(E)-4-Amino-N-(2-butenyloxy)-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)picolinamide (Compound 30),

(E)-4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(3-chloro-2-propenyl-oxy)picolinamide (Compound 31), and

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-((2-chlorothiazol-5-yl)-methoxy)picolinamide (Compound 41).

7. The method of claim 2 wherein the compound of Formula I is applied to said undesirable vegetation in the presence of oilseed rape; and said undesirable vegetation comprises lambsquarters ( Chenopodium album ) or purple deadnettle ( Lamium purpureum ).

8. The method of claim 7 wherein the compound of Formula I is selected from the group consisting of:

4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-(2-methylpropoxy)picolinamide (Compound 1),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-methoxypicolinamide (Compound 2),

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-ethoxypicolinamide (Compound 4),

(E)-4-Amino-N-(2-butenyloxy)-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)picolinamide (Compound 30),

N-(2-Propenyloxy)-4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinamide (Compound 39), and

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-N-(tetrahydro-2H-pyran-2-yloxy)picolinamide (Compound 48).