Synergistic weed control from applications of pyridine carboxylic acid herbicides and synthetic auxin herbicides and/or auxin transport inhibitors

• US 9,521,847 B2
• Filed: 09/15/2015
• Issued: 12/20/2016
• Est. Priority Date: 09/15/2014
• Status: Active Grant

• Current Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Satchivi, Norbert M., Bangel, Bryston L., Degenhardt, Rory Frank, Juras, Len, Schmitzer, Paul R., Bell, Jared L., Ransberger, Jennifer Lynn
• Primary Examiner(s): PAK, JOHN D
• Application Number:
  US14/854,912
• Publication Number:
  US 20160135458A1
• Time in Patent Office: 462 Days
• US Class Current: 1/1
• CPC Class Codes: A01N 37/10 Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
• CPC Class Codes: A01N 37/30 containing the groups —CO—N< and , both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
• CPC Class Codes: A01N 37/40 having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
• CPC Class Codes: A01N 37/44 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
• CPC Class Codes: A01N 39/02 Aryloxy-carboxylic acids; Derivatives thereof
• CPC Class Codes: A01N 39/04 Aryloxy-acetic acids; Derivatives thereof
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/42 condensed with carbocyclic rings
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: A01N 47/34 containing the groups , e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 417/04 directly linked by a ring-member-to-ring-member bond

Abstract

Disclosed herein are herbicidal compositions comprising a herbicidally effective amount of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt or ester thereof, and (b) a synthetic auxin herbicide, an auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof. Also disclosed herein are methods of controlling undesirable vegetation which comprise applying to vegetation or an area adjacent the vegetation or applying to soil or water to prevent the emergence or growth of vegetation (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt or ester thereof, and (b) a synthetic auxin herbicide, an auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof, wherein (a) and (b) are each added in an amount sufficient to provide a herbicidal effect.

Claims

1. A herbicidal composition comprising a synergistic herbicidally effective amount of (a) a pyridine carboxylic acid herbicide defined by Formula (I)

2. The composition of claim 1, wherein the pyridine carboxylic acid herbicide comprises a compound defined by Formula (II)

3. The composition of claim 2, wherein

R¹ is OR^1′

, wherein R^1′

is hydrogen, 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, C₁-C₄-alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, or C₁-C₄ haloalkylthio;

R³ and R⁴ are hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, or R³ and R⁴ taken together represent ═

CR^3′

(R^4′

), wherein R^3′

and R^4′

are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino;

A is A2, A3, A8, A13, or A15;

R⁵, when A is A2, A3, A8, or A13, is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, or C₂-C₄ haloalkylamino;

R⁵, when A is A15, is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, or C₂-C₄ haloalkylamino;

R⁶ and R^6′

are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, CN, or NO₂;

R⁷ and R^7′

are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, cyclopropyl, amino, or C₁-C₄ alkylamino; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₄ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, or C₁-C₆ alkylcarbamyl.

4. The composition of claim 1, wherein the pyridine carboxylic acid herbicide comprises a compound defined by Formula (III):

5. The composition of claim 1, wherein the pyridine carboxylic acid herbicide is one of the following:

6. The composition of claim 1, wherein the pyridine carboxylic acid herbicide is

7. The composition of claim 1, wherein (b) is a synthetic auxin herbicide.

8. The composition of claim 7, wherein the weight ratio of (a) to (b) is from 1:

8000 to 300;

1.

9. The composition of claim 1, wherein (b) is an auxin transport inhibitor.

10. The composition of claim 9, wherein the weight ratio of (a) to (b) is from 1:

1000 to 85;

1.

11. The composition of claim 1, further comprising a herbicidal safener.

12. The composition of claim 1, further comprising an agriculturally acceptable adjuvant or carrier.

13. The composition of claim 1, further comprising an additional pesticide.

14. The composition of claim 1, wherein the active ingredients in the composition consist of (a) and (b).

15. The composition of claim 1, wherein the composition is provided as a herbicidal concentrate.

16. A method of controlling undesirable vegetation comprising applying to vegetation or an area adjacent the vegetation or applying to soil or water to control the emergence or growth of vegetation a synergistic herbicidally effective amount of the composition of claim 1.

17. The method of claim 16, wherein (a) and (b) are applied post-emergence to the undesirable vegetation.

18. The method of claim 16, wherein (a) is applied in amount of from 0.1 g ae/ha to 300 g ae/ha.

19. The method of claim 16, wherein (b) is a synthetic auxin herbicide and (b) is applied in amount of from 1 g ae/ha to 4000 g ae/ha.

20. The method of claim 16, wherein (b) is an auxin transport inhibitor and (b) is applied in an amount of from 1 g ae/ha to 5500 g ae/ha.

21. The method of claim 16, further comprising applying a herbicidal safener.

22. The method of claim 16, further comprising applying an additional pesticide.

23. The method of claim 16, wherein the undesirable vegetation is controlled in spring barley (Hordeum vulgare, HORVS), winter wheat (Triticum aestivum, TRZAW), spring wheat (Triticum aestivum, TRZAS), common rice (Oryza sativa, ORYSA), maize (Zea mays, ZEAMX), or combinations thereof.

24. The method of claim 16, wherein the undesirable vegetation includes a broadleaf weed.

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

26. The method of claim 16, wherein the undesirable vegetation includes velvetleaf (Abutilon theophrasti, ABUTH), blackgrass (Alopecurus myosuroides, ALOMY), pigweed (Amaranthus retroflexus, AMARE), wild oat (Avena fatua, AVEFA), Chinese kale (Brassica alboglabra, BRSAG), brown mustard (Brassica juncea, BRSJU), rutabaga (Brassica napus var. napobrassica, BRSNA), black mustard (Brassica nigra, BRSNI), spring rape (Brassica napus, BRSNN), spring rape-Roundup Ready (Brassica napus, BRSNN-RR), winter rape (Brassica napus, BRSNW), turnip (Brassica rapa, BRSRR), common lambsquarters (Chenopodium album L., CHEAL), Canadian thistle (Cirsium arvense, CIRAR), nutsedge (Cyperus esculentus, CYPES), large crabgrass (Digitaria sanguinalis, DIGSA), poinsettia (Euphorbia heterophylla, EPHHL), soybean (Glycine max, GLXMA), sunflower (Helianthus annus, HELAN), ivyleaf morningglory (Ipomoea hederacea, IPOHE), kochia (Kochia scoparia, KCHSC), mallow (Malva pusilla, MALPU), wild buckwheat (Polygonum convolvulus, POLCO), lady'"'"'s thumb (Polygonum persicaria, POLPE), wild radish (Raphanus raphanistrum, RAPRA), Russian thistle (Salsola iberica, SASKR), wild mustard (Sinapsis arvensis, SINAR), grain sorghum (Sorghum vulgare, SORVU), Indian hedge mustard (Sisymbrium orientale, SSYOR), common chickweed (Stellaria media, STEME), ivyleaved speedwell (Veronica hederifolia, VERHE), wild pansy (Viola tricolor, VIOTR), or a combination thereof.

27. The method of claim 16, wherein the active ingredients applied to the vegetation or an area adjacent the vegetation or applied to soil or water to control the emergence or growth of vegetation consist of (a) and (b).