Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and fungicides

• US 9,730,445 B2
• Filed: 03/03/2014
• Issued: 08/15/2017
• Est. Priority Date: 03/15/2013
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Yerkes, Carla N., Mann, Richard K.
• Primary Examiner(s): Pryor, Alton
• Application Number:
  US14/769,606
• Publication Number:
  US 20150373972A1
• Time in Patent Office: 1,261 Days
• Field of Search: None
• CPC Class Codes: A01N 37/24 containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
• CPC Class Codes: A01N 37/50 the nitrogen atom being doubly bound to the carbon skeleton
• CPC Class Codes: A01N 43/12 condensed with a carbocyclic ring
• CPC Class Codes: A01N 43/16 with oxygen as the ring hetero atom
• CPC Class Codes: A01N 43/28 with two hetero atoms in positions 1,3
• 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 43/653 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• 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 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: A01N 47/14 Di-thio analogues thereof
• CPC Class Codes: A01N 47/18 containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
• CPC Class Codes: A01N 57/14 containing aromatic radicals

Abstract

Provided herein are synergistic herbicidal compositions containing (a) a compound of formula (I): or an agriculturally acceptable salt or ester thereof and (b) fungicides, including but not limited to, azoxystrobin, carbendazim, difenoconazole, flutolanil, hexaconazole, iprobenfos, isoprothiolane, isotianil, kasugamycin, mancozeb, myclobutanil, phthalide, probenazole, propiconazole, pyroquilon, tebuconazole, thifluzamide, tricyclazole, trifloxystrobin, validamycin, or a compound of formula (II) The compositions and methods provided herein control undesirable vegetation, e.g., in direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, plantation crops, vegetables, industrial vegetation management (IVM) and rights-of-way (ROW).

Claims

1. A herbicidal composition comprising a herbicidally effective amount of (a) a compound of the formula (I):

2. The composition of claim 1, wherein (a) is a benzyl ester of the compound of formula (I).

3. The composition of claim 1, wherein (a) is a C₁-C₄ alkyl ester of the compound of formula (I).

4. The composition of claim 1, wherein (a) is the compound of formula (I).

5. The composition of claim 1, further comprising at least one compound selected from the group consisting of:

herbicide safeners, carriers and adjuvants.

6. The composition of claim 1, wherein (b) is selected from the group consisting of isoprothiolane, phthalide, and pyroquilon.

7. The composition of claim 1, wherein the ratio between the compound of the formula (I) and azoxystrobin is from about 1:

11.8 to about 1;

47.2;

the ratio between the benzyl ester of the compound of formula (I) and azoxystrobin is from about 1;

1.95 to about 1;

57.1;

wherein the ratio between the benzyl ester of the compound of formula (I) and carbendazim is from about 1;

3.9 to about 1;

31.3;

wherein the ratio between the compound of the formula (I) and difenoconazole is from about 1;

9.4 to about 1;

37.7;

wherein the ratio between the benzyl ester of the compound of formula (I) and difenoconazole is from about 1;

1.6 to about 1;

45.7;

wherein the ratio between the benzyl ester of the compound of formula (I) and flutolanil is from about 1;

8.8 to about 1;

70;

wherein the ratio between the benzyl ester of the compound of formula (I) and hexaconazole is from about 1.3;

1 to about 1;

12.5;

wherein the ratio between the benzyl ester of the compound of formula (I) and isoprothiolane is from about 1;

6.3 to about 1;

66.6;

wherein the ratio between the benzyl ester of the compound of formula (I) and isotianil is from about 1;

3.1 to about 1;

47.5;

wherein the ratio between the benzyl ester of the compound of formula (I) and kasugamycin is from about 1.8;

1 to about 1;

8.8;

wherein the ratio between the benzyl ester of the compound of formula (I) and mancozeb is from about 1;

26.3 to about 1;

210;

wherein the ratio between the compound of the formula (I) and myclobutanil is from about 1;

11.8 to about 1;

23.6;

wherein the ratio between the benzyl ester of the compound of formula (I) and myclobutanil is from about 1;

1.6 to about 1;

57.1;

wherein the ratio between the benzyl ester of the compound of formula (I) and phthalide is from about 1;

6.3 to about 1;

37.5;

wherein the ratio between the benzyl ester of the compound of formula (I) and probenazole is from about 1;

31.3 to about 1;

500;

wherein the ratio between the compound of the formula (I) and propiconazole is from about 1;

9 to about 1;

35.9;

wherein the ratio between the benzyl ester of the compound of formula (I) and propiconazole is from about 1;

4 to about 1;

31.3;

wherein the ratio between the benzyl ester of the compound of formula (I) and pyroquilon is from about 1;

28.9 to about 1;

115.6;

wherein the ratio between the compound of the formula (I) and tebuconazole is from about 1;

11.8 to about 1;

47.2;

wherein the ratio between the benzyl ester of the compound of formula (I) and tebuconazole is from about 1;

2.0 to about 1;

57.1;

wherein the ratio between the benzyl ester of the compound of formula (I) and thifluzamide is from about 1;

2.3 to about 1;

9.4;

wherein the ratio between the compound of the formula (I) and tricyclazole is from about 1;

9.4 to about 1;

37.7;

wherein the ratio between the benzyl ester of the compound of formula (I) and tricyclazole is from about 1;

1.6 to about 1;

93.8;

wherein the ratio between the benzyl ester of the compound of formula (I) and trifloxystrobin is from about 1;

8.8 to about 1;

37.5;

wherein the ratio between the benzyl ester of the compound of formula (I) and a compound of formula (II) is from about 1;

1.2 to about 1;

18.8.

8. A method of controlling undesirable vegetation comprising:

contacting a plant, wherein the plant is undesirable vegetation, an area adjacent to the plant, soil, or water, wherein the soil or the water allows for the growth of the undesirable vegetation, with a herbicidally effective amount of a combination comprising (a) a compound of the formula (I);

9. The method of claim 8, wherein the undesirable vegetation is immature.

10. The method of claim 8, wherein the (a) and (b) are applied to water.

11. The method of claim 10, wherein the water is part of a flooded rice paddy.

12. The method of claim 8, wherein the (a) and (b) are applied pre-emergently and/or post emergently to the undesirable vegetation in a crop.

13. The method of claim 8, wherein the (a) and (b) are applied post-emergently to the undesirable vegetation in a crop.

14. The method of claim 8, wherein the undesirable vegetation is controlled in glyphosate-, 5-enolpyruvylshikimate-3-phosphate synthase inhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase inhibitor-, imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactate synthase or acetohydroxy acid synthase inhibitor-, 4-hydroxyphenyl-pyruvate dioxygenase inhibitor-, phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-, triazine-, or bromoxynil-tolerant crops.

15. The method of claim 14, wherein the tolerant crops possess multiple or stacked traits conferring tolerance to multiple herbicides.

16. The method of claim 8, wherein the undesirable vegetation comprises a herbicide resistant or tolerant plant.

17. The method of claim 16, wherein the resistant or tolerant plant is resistant or tolerant to multiple herbicides.

18. The method of claim 16, wherein the resistant or tolerant plant is resistant or tolerant to acetolactate synthase or acetohydroxy acid synthase inhibitors, photosystem II inhibitors, acetyl CoA carboxylase inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate synthase inhibitors, microtubule assembly inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid inhibitors, phytoene desaturase inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action, quinclorac, arylaminopropionic acids, difenzoquat, endothall, or organoarsenicals.

19. The method of claim 17, wherein the resistant or tolerant plant is a biotype resistant or tolerant to acetolactate synthase or acetohydroxy acid synthase inhibitors, photosystem II inhibitors, acetyl CoA carboxylase inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate synthase inhibitors, microtubule assembly inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid inhibitors, phytoene desaturase inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action, quinclorac, arylaminopropionic acids, difenzoquat, endothall, or organoarsenicals.

20. The method of claim 8, wherein (b) is selected from the group consisting of isoprothiolane, phthalide, and pyroquilon.

21. The method of claim 8, wherein the ratio between the compound of the formula (I) and azoxystrobin is from about 1:

11.8 to about 1;

47.2;

the ratio between the benzyl ester of the compound of formula (I) and azoxystrobin is from about 1;

1.95 to about 1;

57.1;

wherein the ratio between the benzyl ester of the compound of formula (I) and carbendazim is from about 1;

3.9 to about 1;

31.3;

wherein the ratio between the compound of the formula (I) and difenoconazole is from about 1;

9.4 to about 1;

37.7;

wherein the ratio between the benzyl ester of the compound of formula (I) and difenoconazole is from about 1;

1.6 to about 1;

45.7;

wherein the ratio between the benzyl ester of the compound of formula (I) and flutolanil is from about 1;

8.8 to about 1;

70;

wherein the ratio between the benzyl ester of the compound of formula (I) and hexaconazole is from about 1.3;

1 to about 1;

12.5;

wherein the ratio between the benzyl ester of the compound of formula (I) and isoprothiolane is from about 1;

6.3 to about 1;

66.6;

wherein the ratio between the benzyl ester of the compound of formula (I) and isotianil is from about 1;

3.1 to about 1;

47.5;

wherein the ratio between the benzyl ester of the compound of formula (I) and kasugamycin is from about 1.8;

1 to about 1;

8.8;

wherein the ratio between the benzyl ester of the compound of formula (I) and mancozeb is from about 1;

26.3 to about 1;

210;

wherein the ratio between the compound of the formula (I) and myclobutanil is from about 1;

11.8 to about 1;

23.6;

wherein the ratio between the benzyl ester of the compound of formula (I) and myclobutanil is from about 1;

1.6 to about 1;

57.1;

wherein the ratio between the benzyl ester of the compound of formula (I) and phthalide is from about 1;

6.3 to about 1;

37.5;

wherein the ratio between the benzyl ester of the compound of formula (I) and probenazole is from about 1;

31.3 to about 1;

500;

wherein the ratio between the compound of the formula (I) and propiconazole is from about 1;

9 to about 1;

35.9;

wherein the ratio between the benzyl ester of the compound of formula (I) and propiconazole is from about 1;

4 to about 1;

31.3;

wherein the ratio between the benzyl ester of the compound of formula (I) and pyroquilon is from about 1;

28.9 to about 1;

115.6;

wherein the ratio between the compound of the formula (I) and tebuconazole is from about 1;

11.8 to about 1;

47.2;

wherein the ratio between the benzyl ester of the compound of formula (I) and tebuconazole is from about 1;

2.0 to about 1;

57.1;

wherein the ratio between the benzyl ester of the compound of formula (I) and thifluzamide is from about 1;

2.3 to about 1;

9.4;

wherein the ratio between the compound of the formula (I) and tricyclazole is from about 1;

9.4 to about 1;

37.7;

wherein the ratio between the benzyl ester of the compound of formula (I) and tricyclazole is from about 1;

1.6 to about 1;

93.8;

wherein the ratio between the benzyl ester of the compound of formula (I) and trifloxystrobin is from about 1;

8.8 to about 1;

37.5;

wherein the ratio between the benzyl ester of the compound of formula (I) and a compound of formula (II) is from about 1;

1.2 to about 1;

18.8.