BENZOIC ACID HERBICIDE COMPOSITION

• US 20180153161A1
• Filed: 05/06/2016
• Published: 06/07/2018
• Est. Priority Date: 05/07/2015
• Status: Active Grant

• Current Assignee: Nufarm Australia Limited (Nufarm Ltd.)
• Original Assignee: Nufarm Australia Limited (Nufarm Ltd.)
• Inventors: SHARMA, Sumit, PANAYI, Aristos, SAYER, Chad Richard Ord
• Granted Patent: US 10,772,323 B2
• Time in Patent Office: Days
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 25/02 containing liquids as carriers, diluents or solvents
• CPC Class Codes: A01N 25/04 Dispersions, emulsions, suspoemulsions, suspension concentrates or gels foams A01N25/16
• CPC Class Codes: A01N 25/30 characterised by the surfactants
• CPC Class Codes: A01N 33/04 Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
• CPC Class Codes: A01N 33/08 containing oxygen or sulfur
• CPC Class Codes: A01N 37/20 containing the group , wherein Cn means a carbon skeleton not containing a ring; 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 43/40 six-membered rings

Abstract

An emulsifiable concentrate comprising a benzoic acid herbicide in acid form dissolved in an amide solvent and an amide solvent and an amine emulsion stabiliser. Preferably: •the benzoic acid herbicide is selected from TBA, chloramben and dicamba acid, •the amine is of the formula (I) NR¹R²R³ where wherein R¹, R² and R³ are independently selected from the group selected from hydrogen; C₁ to C₁₀ alkyl; C₅ or C₆ cycloaliphatic optionally substituted with from one to four C₁ to C₄ alkyl groups and/or an amino-C₁ to C₄ alkyl group; C₁ to C₁₀ alkyl substituted with a substituent selected from the group consisting of hydroxyl, C₁ to C₁₀ alkoxy, amino, (C₁ to C₅ alkyl)amino and di-(C₁ to C₆ alkyl)amino; and the group wherein two of R₁, R² and R³ together form a ring of 5 or 6 constituent ring members selected from methylene, —O—, —N(H)— and —N(C₁ to C₆-alkyl) and the other of R¹, R² and R³ is selected from hydrogen, C₁ to C₅ alkyl and C₁ to C₅ alkyl substituted with a substituent selected from the group consisting of hydroxyl, C₁ to C₅ alkoxy, amino and (C₁ to C₅ alkyl)amino; and wherein at least one of R¹, R² and R³ is other than hydrogen, and •the amide solvents are of the formula (II) R⁴—CON—R⁵R⁶ where R is selected from the group consisting of hydrogen and C₁ to C₁₇ hydrocarbyl, and R⁵ and R⁶ are is selected from the group consisting of C₁ to C₁₅ hydrocarbyl and may together from a ring incorporating the nitrogen of the amide comprising 4 or 5 methylene groups.

Claims

1. An emulsifiable concentrate comprising a benzoic acid herbicide in acid form dissolved in an amide solvent and an amine.

2. An emulsifiable concentrate according to claim 1 wherein the amine comprises at least one amine of formula I

3. An emulsifiable concentrate according to claim 2 wherein, in the amine of formula I, R¹ is C₁ to C₆ hydroxyalkyl or C₁ to C₆ alkoxy substituted C₂ to C₄ alkyl and R² and R³ are independently hydrogen or C₁ to C₄ alkyl.

4. An emulsifiable concentrate according to claim 3 wherein, in the amine of formula I, R¹ is C₂ to C₆ hydroxylalkyl or C₁ to C₆ alkoxy-substituted C₂ to C₄ alkyl and R² and R³ are hydrogen.

5. An emulsifiable concentrate according to claim 3 wherein, in the amine of formula I, R¹ is C₂ to C₄ hydroxyalkyl or C₁ to C₆ alkoxy-substituted C₂ to C₄ alkyl and R² and R³ are hydrogen.

6. An emulsifiable concentrate according to claim 1 wherein the amine is selected from the group consisting of ethanolamine, methoxypropylamine and hexyloxypropylamine.

8. An emulsifiable concentrate according to claim 1, wherein the amount of the amine in the concentrate composition is from 0.5% to 10% by weight based on the weight of an emulsifiable concentrate containing benzoic acid herbicide in acid form.

9. An emulsifiable concentrate according to claim 1, wherein the amount of the amine in the concentrate composition is from 3% to 5% by weight based on the weight of an emulsifiable concentrate containing benzoic acid herbicide in acid form.

10. An emulsifiable concentrate according to claim 1, wherein the amide solvent is of formula II:

11. An emulsifiable concentrate according to claim 10 wherein the amide solvent of formula II wherein

R⁴ is C₆ to C₁₇ alkyl;

and

R⁵ and R⁶ are independently selected from C₁ to C₄ alkyl.

13. An emulsifiable concentrate according to claim 1, wherein the amide solvent is selected from the group consisting of N,N-dimethyl octanamide, N,N-dimethyl decanamide, N,N-dimethyl caprylamide, N,N-dimethyl 2-ethylhexanoamide, N,N-dimethyl oleamide, N,N-dimethylLauricamide, N,N-dimethylmyristicamide, N,N-dimethyl 9-decenamide, and mixtures of two or more thereof.

14. An emulsifiable concentrate according to claim 1, wherein the benzoic acid herbicide is selected from the group consisting of TBA, chloramben and dicamba acid.

15. An emulsifiable concentrate according to claim 1, wherein the benzoic acid herbicide is present in an amount of at least 200 g acid per litre of emulsifiable concentrate

16. An emulsifiable concentrate according to claim 1, wherein the benzoic acid herbicide is present in an amount of at least 450 g/L.

17. An emulsifiable concentrate according to claim 1 further comprising a hydrocarbon co-solvent having a flash point of at least 60.5°

C. comprising at least one hydrocarbon selected from alkyl substituted aromatics selected from the group consisting of mono-, di- and trialkyl benzenes.

19. An emulsifiable concentrate according to claim 17, wherein the hydrocarbon co-solvent is present in an amount in the range of from 2% to 25% w/w of the emulsifiable concentrate.

21. An emulsifiable concentrate according to claim 1 comprising emulsifier in an amount in the range of from 5% w/w to 25% w/w of the concentrate composition.

23. An emulsifiable concentrate according to claim 21, wherein the emulsifier comprises a non-ionic emulsifier selected from alcohol ethoxylates, fatty acid ethoxylates, fatty amide ethoxylates and EO/PO block copolymers, in an amount in the range of from 2% w/w to 20% w/w of the concentrate composition.

24. An emulsifiable concentrate according to claim 21 comprising anionic emulsifier in an amount of from 1% to 10% w/w of the concentrate composition and non-ionic emulsifier in an amount of from 2% to 15% w/w of the concentrate composition.

27. A method of controlling weeds comprising providing an emulsifiable concentrate according to claim 1 diluting the concentrate with water to form an emulsion and applying the diluted composition to the weeds.

7. (canceled)

12. (canceled)

18. (canceled)

20. (canceled)

22. (canceled)

25. An emulsifiable concentrate composition comprising:

dicamba acid in an amount of at least 250 g/L;

fatty acid amide solvent in an amount of from 25% to 60% w/w of the concentrate composition;

hydrocarbon co-solvent in an amount of from 2% to 25% w/w of the concentrate composition;

anionic emulsifier in an amount of from 1% to 10% w/w of the concentrate composition;

non-ionic emulsifier in an amount of from 2% to 25% w/w of the concentrate composition; and

monoethanolamine, methoxypropylamine or mixture thereof in an amount of from 0.5% to 10% by weight based on the weight of an emulsifiable concentrate composition.

26. (canceled)