Salts of carboxylic acid herbicides

• US 10,334,849 B2
• Filed: 10/26/2012
• Issued: 07/02/2019
• Est. Priority Date: 10/26/2011
• Status: Active Grant

• Current Assignee: Monsanto Technology LLC (Bayer AG)
• Original Assignee: Monsanto Technology LLC (Bayer AG)
• Inventors: Zhang, Junhua, Wright, Daniel R., Abraham, William
• Primary Examiner(s): Richter, Johann R
• Assistant Examiner(s): Brown, Courtney A
• Application Number:
  US14/354,287
• Publication Number:
  US 20140309114A1
• Time in Patent Office: 2,440 Days
• Field of Search: 504128, 504225, 504235, 504275, 544358, 544401, 544403, 544 87, 546184, 546186, 546242, 546248, 5483351, 5483435
• 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 39/04 Aryloxy-acetic acids; Derivatives thereof
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/50 1,3-Diazoles; Hydrogenated 1,3-diazoles
• CPC Class Codes: A01N 43/60 1,4-Diazines; Hydrogenated 1,4-diazines
• CPC Class Codes: A01N 43/84 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
• CPC Class Codes: A01N 57/20 containing acyclic or cycloaliphatic radicals

Abstract

Amine salts of certain herbicides that in free acid form include at least one carboxylic acid moiety are described. Herbicide salts comprising the cation of various imidazole, piperazine, piperidine, and morpholine compounds are provided. The herbicide amine salts described are suitable for formulation into herbicidal application mixtures and/or stable concentration compositions that exhibit acceptable volatility characteristics upon application.

Claims

1. A herbicide salt comprising an anion of an auxin herbicide and a cation of a compound selected from the group consisting of:

(a) Formula I;

2. The herbicide salt of claim 1 comprising a cation of the compound of Formula I.

3. The herbicide salt of claim 2 wherein R² and R³ are independently hydrogen, substituted or unsubstituted C₁-C₂₀ alkyl, substituted or unsubstituted C₁-C₂₀ alkanol, substituted or unsubstituted C₅-C₂₀ cycloalkyl, substituted or unsubstituted C₃-C₂₀ heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

4. The herbicide salt of claim 1 comprising a cation of the compound of Formula II.

5. The herbicide salt of claim 4 wherein R⁴ and R⁵ are independently substituted or unsubstituted C₁-C₂₀ alkyl, substituted or unsubstituted C₁-C₂₀ alkanol, substituted or unsubstituted C₃-C₂₀ cycloalkyl, substituted or unsubstituted C₁-C₂₀ heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, provided that when R⁵ is an unsubstituted C₁-C₆ alkyl, then R⁴ is not an aminoalkyl or when R⁴ is an unsubstituted C₁-C₆ alkyl, then R⁵ is not an aminoalkyl.

6. The herbicide salt of claim 1 comprising a cation of the compound of Formula III.

7. The herbicide salt of claim 6 wherein R⁶ is a substituted or unsubstituted C₁-C₁₀ alkyl, substituted or unsubstituted C₁-C₁₀ alkanol, substituted or unsubstituted C₅-C₁₀ cycloalkyl, substituted or unsubstituted C₃-C₁₀ heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, or substituted or unsubstituted heteroaryl.

8. The herbicide salt of claim 1 comprising a cation of the compound of Formula IV.

9. The herbicide salt of claim 1 comprising a cation of a compound of Formula V.

10. The herbicide salt of claim 1 comprising the cation of a compound selected from the group consisting of:

11. The herbicide salt of claim 1 wherein the auxin herbicide comprises at least one herbicide selected from the group consisting of 3,6-dichloro-2-methoxybenzoic acid (dicamba);

2,4-dichlorophenoxyacetic acid (2,4-D);

4-(2,4 dichlorophenoxy)butanoic acid (2,4-DB);

2-(2,4-dichlorophenoxy)propanoic acid (dichloroprop);

2-(4-chloro-2-methylphenoxy)acetic acid (MCPA);

4-(4-chloro-2-methylphenoxy)butanoic acid (MCPB);

4-amino-3,6-dichloro-2-pyridinecarboxylic acid (aminopyralid);

3,6-dichloro-2-pyridinecarboxylic acid (clopyralid);

2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]acetic acid (fluroxypyr);

[(3,5,6-trichloro-2-pyridinyl)oxy]acetic acid (triclopyr);

2-(4-chloro-2-methylphenoxy)propanoic acid (mecoprop);

4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid (picloram);

3,7-dichloro-8-quinolinecarboxylic acid (quinclorac);

6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (aminocyclopyrachlor) and combinations thereof.

12. The herbicide salt of claim 1 wherein the auxin herbicide comprises 3,6-dichloro-2-methoxybenzoic acid (dicamba) or 2,4-dichlorophenoxyacetic acid (2,4-D).

13. A herbicidal application mixture useful for killing or controlling the growth of unwanted plants comprising the herbicidal salt of claim 1.

14. The herbicidal application mixture of claim 13 further comprising at least one surfactant wherein the weight ratio of the herbicidal salt acid equivalent to surfactant is from about 1:

1 to about 20;

1.

15. The herbicidal application mixture of claim 13 further comprising at least one co-herbicide selected from the group consisting of auxin herbicides and salts thereof;

acetyl CoA carboxylase (ACCase) inhibitors, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, photosystem II inhibitors, photosystem I inhibitors, protoporphyrinogen oxidase (PPO or Protox) inhibitors, carotenoid biosynthesis inhibitors, enolpyruvyl shikimate-3-phosphate (EPSP) synthase inhibitor, glutamine synthetase inhibitor, dihydropteroate synthetase inhibitor, mitosis inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (4-HPPD) inhibitors, synthetic auxins, auxin transport inhibitors, nucleic acid inhibitors, and salts and esters thereof;

racemic mixtures and resolved isomers thereof; and

combinations thereof.

16. The herbicidal application mixture of claim 13 further comprising at least one co-herbicide selected from:

2,4-D, aminocyclopyrachlor, mecoprop, mecoprop-P, triclopyr, acetochlor, acifluorfen, alachlor, atrazine, azafenidin, bifenox, butachlor, butafenacil, carfentrazone-ethyl, diuron, dithiopyr, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluthiacet-methyl, fomesafen, glyphosate, glufosinate, imazethapyr, lactofen, metazochlor, metolachlor (and S-metolachlor), metribuzin, oxadiargyl, oxadiazon, oxyfluorfen, pretilachlor, propachlor, propisochlor, pyraflufen-ethyl, sulfentrazone and thenylchlor, and salts and esters thereof;

racemic mixtures and resolved isomers thereof, and combinations thereof.

17. The herbicidal application mixture of claim 13 wherein the co-herbicide comprises glyphosate or a salt or ester thereof.

18. A method of controlling unwanted plants comprising applying the herbicidal application mixture of claim 13 to the unwanted plants.

19. A method of controlling carboxylic acid herbicide-susceptible plants growing in and/or adjacent to a field of crop plants comprising applying the herbicidal application mixture of claim 13 to the foliage of the carboxylic acid herbicide-susceptible plants.

20. The method of claim 19 wherein the crop plant comprises a transgenic crop plant comprising a herbicide tolerant trait selected from the group consisting of a dicamba tolerance trait, a 2,4-D tolerance trait, a glyphosate tolerance trait, a glufosinate tolerance trait, and combinations thereof.

21. The herbicide salt of claim 3 wherein R² and R³ are independently hydrogen or substituted or unsubstituted C₁-C₁₀ alkyl.

22. The herbicide salt of claim 21 wherein R¹ is a substituted or unsubstituted C₁-C₁₀ alkyl, substituted or unsubstituted C₁-C₁₀ alkanol, substituted or unsubstituted C₅-C₁₀ cycloalkyl, substituted or unsubstituted C₃-C₁₀ heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

23. The herbicide salt of claim 22 wherein R¹ is a C₁-C₆ alkyl, C₁-C₆ alkanol, C₅-C₆ cycloalkyl, or aryl.

24. The herbicide salt of claim 23 wherein R¹ is methyl, ethyl, isopropyl or phenyl.