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

• US 8,889,694 B2
• Filed: 08/08/2013
• Issued: 11/18/2014
• Est. Priority Date: 02/27/2009
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Eckelbarger, Joseph D., Schmitzer, Paul R., Yerkes, Carla N., Boebel, Timothy A., Satchivi, Norbert M., Whiteker, Gregory T.
• Primary Examiner(s): Leeser, Erich A
• Application Number:
  US13/962,333
• Publication Number:
  US 20130324412A1
• Time in Patent Office: 467 Days
• Field of Search: 514/256, 514/336, 514/340, 514/342, 514/352, 544/298, 544/329, 546/297, 546/309
• US Class Current: 514/256
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/72 having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: A01N 43/82 five-membered rings with three ring hetero atoms
• CPC Class Codes: C07D 213/81 Amides; Imides
• CPC Class Codes: C07D 239/28 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
• CPC Class Codes: C07D 239/30 Halogen atoms or nitro radicals
• CPC Class Codes: C07D 239/42 One nitrogen atom nitro radicals C07D239/30
• CPC Class Codes: C07D 239/47 One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 413/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links

Abstract

N-Alkoxyamides of 4-aminopicolinic acids and 6-amino-4-pyrimidinecarboxylates are selective herbicides for corn, canola and sugar beet.

Claims

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

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,

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).