SAFENED HERBICIDAL COMPOSITIONS COMPRISING A PYRIDINE CARBOXYLIC ACID HERBICIDE

• US 20160073632A1
• Filed: 09/15/2015
• Published: 03/17/2016
• 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., Schmitzer, Paul R.
• Granted Patent: US 9,763,445 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: A01N 25/32 Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
• 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

Abstract

Disclosed herein are safened herbicidal compositions comprising (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt or ester thereof and (b) a quinolinyloxyacetate safener or agriculturally acceptable salt or ester thereof. Also disclosed herein are methods of controlling undesirable vegetation, comprising applying to vegetation or an area adjacent the vegetation or applying in soil or water to control the emergence or growth of vegetation (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt or ester thereof and (b) an quinolinyloxyacetate safener or agriculturally acceptable salt or ester thereof.

Claims

1. A safened herbicidal composition, comprising:

(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 A1, A2, A3, A7, A8, A9, A10, A11, A12, A13, A14, A15, A21, A22, A23, A24, A27, A28, A29, A30, A31, or A32;

R⁵ 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;

R⁶, R^6′

, 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 comprises one of the following:

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

7. The composition of claim 1, wherein the quinolinyloxyacetate safener comprises cloquintocet or an agriculturally acceptable salt or ester thereof.

8. The composition of claim 1, wherein the quinolinyloxyacetate safener comprises cloquintocet-mexyl.

9. The composition of claim 1, wherein the weight ratio of (a) in g ae/ha to (b) in g ai/ha is from 65:

1 to 1;

5.

10. The composition of claim 9, wherein the weight ratio of (a) in g ae/ha to (b) in g ai/ha is from 5:

1 to 1;

5.

11. The composition of claim 10, wherein the weight ratio of (a) in g ae/ha to (b) in g ai/ha is from 2:

1 to 1;

2.

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. 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) a pyridine carboxylic acid herbicide comprising a compound defined by Formula (I)

16. The method of claim 15, wherein the pyridine carboxylic acid herbicide comprises a compound defined by Formula (II)

17. The method of claim 16, 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 A1, A2, A3, A7, A8, A9, A10, A11, A12, A13, A14, A15, A21, A22, A23, A24, A27, A28, A29, A30, A31, or A32;

R⁵ 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;

R⁶, R^6′

, 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.

18. The method of claim 15, wherein the pyridine carboxylic acid herbicide comprises a compound defined by Formula (III):

19. The method of claim 15, wherein the pyridine carboxylic acid herbicide comprises one of the following:

20. The method of claim 15, wherein the pyridine carboxylic acid herbicide comprises

21. The method of claim 15, wherein the quinolinyloxyacetate safener comprises cloquintocet or an agriculturally acceptable salt or ester thereof.

22. The method of claim 21, wherein the quinolinyloxyacetate safener comprises cloquintocet-mexyl.

23. The method of claim 15, wherein (a) and (b) are applied simultaneously.

24. The method of claim 15, wherein (a) and (b) are applied post-emergence to the undesirable vegetation.

25. The method of claim 15, wherein (a) in g ae/ha and (b) in g ai/ha are applied in a weight ratio of 65:

1 to 1;

5.

26. The method of claim 25, wherein (a) in g ae/ha and (b) in g ai/ha are applied in a weight ratio of 5:

1 to 1;

5.

27. The method of claim 26, wherein (a) in g ae/ha and (b) in g ai/ha are applied in a weight ratio of 2:

1 to 1;

2.

28. The method of claim 15, wherein (a) is applied in amount of from 0.1 g ae/ha to 300 g ae/ha.

29. The method of claim 28, wherein (a) is applied in amount of from 4 g ae/ha to 140 g ae/ha.

30. The method of claim 29, wherein (a) is applied in amount of from 30 g ae/ha to 40 g ae/ha.

31. The method of claim 15, wherein (b) is applied in amount of from 1 g ai/ha to 300 g ai/ha.

32. The method of claim 31, wherein (b) is applied in amount of from 4 g ai/ha to 140 g ai/ha.

33. The method of claim 32, wherein (b) is applied in amount of from 30 g ai/ha to 40 g ai/ha.

34. The method of claim 15, further comprising applying an agriculturally acceptable adjuvant or carrier.

35. The method of claim 15, further comprising applying an additional pesticide.

36. The method of claim 15, wherein the undesirable vegetation is controlled in wheat, barley, triticale, rye, teff, oats, corn/maize, sorghum, rice, sugarcane, vineyards, orchards, perennial plantation crops, soybeans, cotton, sunflower, oilseed rape/canola, sugarbeets, turf, range and pasture, industrial vegetation management (IVM), rights-of-way, or combinations thereof.

37. The method of claim 15, wherein the undesirable vegetation is controlled in a glyphosate-, glufosinate-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, aryloxyphenoxypropionate-, acetyl CoA carboxylase (ACCase) inhibitor-, imidazolinone-, acetolactate synthase (ALS) inhibitor-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, triazine-, or bromoxynil-tolerant crop.

38. The method of claim 37, wherein the tolerant crop possesses multiple or stacked traits conferring tolerance to multiple herbicides or multiple modes of action.

39. The method of claim 15, wherein the undesirable vegetation includes a broadleaf weed.

40. The method of claim 15, wherein the undesirable vegetation comprises a herbicide resistant or tolerant weed.

41. The method of claim 40, wherein the resistant or tolerant weed is a biotype with resistance or tolerance to multiple herbicides, multiple chemical classes, or multiple herbicide modes of action.

42. The method of claim 40, wherein the resistant or tolerant weed is a biotype resistant or tolerant to acetolactate synthase (ALS) inhibitors, photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins, photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, microtubule assembly inhibitors, lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA) inhibitors, phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action, quinclorac, arylaminopropionic acids, difenzoquat, endothall, or organoarsenicals.

43. The method of claim 15, wherein the undesirable vegetation includes velvetleaf (ABUTH, Abutilon theophrasti), pigweed (AMARE, Amaranthus retroflexus), winter rape (BRSNW, Brassica napus), shepherd'"'"'s purse (CAPBP, Capsella bursa-pastoris), cornflower (CENCY, Centaurea cyanus or Cyanus segetum), lambsquarters (CHEAL, Chenopodium album), thistle (CIRAR, Cirsium arvense), nutsedge (CYPES, Cyperus esculentus), poinsettia (EPHHL, Euphorbia heterophylla), cleavers (GALAP, Galium aparine), Helianthus annuus (HELAN, common sunflower), kochia (KCHSC, Kochia scoparia), prickly lettuce (LACSE, Lactuca serriola), purple deadnettle (LAMPU, Lamium purpureum), wild chamomile (MATCH, Matricaria chamomilla), common poppy (PAPRH, Papaver rhoeas), wild buckwheat (POLCO, Polygonum convolvulus), Russian thistle (SASKR, Salsola kali), giant foxtail (SETFA, Setaria faberi), green foxtail (SETVI, Setaria viridis), wild mustard (SINAR, Sinapis arvensis), common sorghum (SORVU, Sorghum vulgare), chickweed (STEME, Stellaria media), bird'"'"'s-eye speedwell (VERPE, Veronica persica), wild pansy (VIOTR, Viola tricolor), or a combination thereof.

44. The method of claim 15, 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).