MODULATION OF RELEASE RATE FROM MICROENCAPSULATED PESTICIDES

• US 20160192645A1
• Filed: 01/06/2016
• Published: 07/07/2016
• Est. Priority Date: 01/06/2015
• Status: Active Grant

• Current Assignee: Monsanto Technology LLC (Bayer AG)
• Original Assignee: Monsanto Technology LLC (Bayer AG)
• Inventors: Friedman, Todd Charles, Yuan, Liwei, Zhang, Junhua, Hemminghaus, John W., Deng, Wenjin
• Granted Patent: US 10,638,751 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• 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 25/28 Microcapsules or nanocapsules
• CPC Class Codes: A01N 37/22 the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
• CPC Class Codes: A01N 37/26 containing the group; 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 41/10 Sulfones; Sulfoxides
• CPC Class Codes: A01N 57/20 containing acyclic or cycloaliphatic radicals

Abstract

Aqueous pesticidal mixtures comprising a microencapsulated pesticide and an agent that modulates the release rate of the pesticide from the microcapsules are described. Also described are various methods of modulating the release rate of a microencapsulated pesticide in a pesticidal mixture. Further, various pesticidal mixtures comprising a microencapsulated pesticide and a co-pesticide that provides for enhanced crop safety are described.

Claims

1. An aqueous herbicidal concentrate composition comprising:

(a) at least one particulate microencapsulated acetamide herbicide dispersed in an aqueous liquid medium comprising a water-immiscible core material comprising the acetamide herbicide and a polyurea shell wall containing the core material, wherein the acetamide herbicide concentration in the composition on an active ingredient basis is at least about 10 wt. %, and

(b) an alkali metal salt of an auxin co-herbicide dissolved in the aqueous liquid medium, wherein the auxin co-herbicide concentration in the composition on an acid equivalent basis is at least about 1 wt.

2. The aqueous herbicidal concentrate composition of claim 1 wherein the polyurea shell wall is formed in a polymerization medium by a polymerization reaction between a polyisocyanate component comprising a polyisocyanate or mixture of polyisocyanates and a polyamine component comprising a polyamine or mixture of polyamines to form the polyurea.

3. The aqueous herbicidal concentrate composition of claim 2 wherein the polyisocyanate component comprises an aliphatic polyisocyanate.

4. The aqueous herbicidal concentrate composition of claim 2 wherein the ratio of amine molar equivalents contained in the polyamine component to isocyanate molar equivalents contained in the polyisocyanate component is at least 1.01:

1, at least about 1.05;

1, at least about 1.1;

1, at least about 1.15;

1, or at least about 1.2;

1.

5. The aqueous herbicidal concentrate composition of claim 2 wherein the ratio of amine molar equivalents contained in the polyamine component to isocyanate molar equivalents contained in the polyisocyanate component is from 1.01:

1 to about 1.7;

1, from 1.01;

1 to about 1.6;

1, from 1.01;

1 to about 1.5;

1, from 1.01;

1 to about 1.4;

1, from 1.01;

1 to about 1.3;

1, from 1.05;

1 to about 1.7;

1, from 1.05;

1 to about 1.6;

1, from 1.05;

1 to about 1.5;

1, from 1.05;

1 to about 1.4;

1, from 1.05;

1 to about 1.3;

1, from about 1.1;

1 to about 1.7;

1, from 1.1;

1 to about 1.6;

1, from 1.1;

1 to about 1.5;

1, from 1.1;

1 to about 1.4;

1, from 1.1;

1 to about 1.3;

1, from about 1.15;

1 to about 1.7;

1, from about 1.15;

1 to about 1.6;

1, from about 1.15;

1 to about 1.5;

1, from about 1.15;

1 to about 1.4;

1, from about 1.15;

1 to about 1.3;

1, from 1.2;

1 to about 1.7;

1, from 1.2;

1 to about 1.6;

1, from 1.2;

1 to about 1.5;

1, from 1.2;

1 to about 1.4;

1, or from 1.2;

1 to about 1.3;

1.

6. The aqueous herbicidal concentrate composition of claim 2 wherein the weight to weight ratio of acetamide herbicide to the shell wall is from about 13:

1 to about 6;

1 or from about 10;

1 to about 6;

1.

7. The aqueous herbicidal concentrate composition of claim 1 wherein the alkali metal salt comprises sodium or potassium.

8. The aqueous herbicidal concentrate composition of claim 1 wherein the auxin co-herbicide is selected from the group consisting of 2,4-D, 2,4-DB, dichloroprop, MCPA, MCPB, aminopyralid, clopyralid, fluroxypyr, triclopyr, diclopyr, mecoprop, dicamba, picloram and quinclorac, and mixtures thereof.

9. The aqueous herbicidal concentrate composition of claim 1 wherein the auxin co-herbicide comprises dicamba.

10. The aqueous herbicidal concentrate composition of claim 1 wherein the auxin co-herbicide comprises 2,4-D.

11. The aqueous herbicidal concentrate composition of claim 1 wherein the alkali metal salt of the auxin co-herbicide comprises sodium.

12. The aqueous herbicidal concentrate composition of claim 1 wherein the auxin co-herbicide concentration in the composition on an acid equivalent basis is from about 1 wt. % to about 30 wt. %, from about 1 wt. % to about 25 wt. %, from about 1 wt. % to about 20 wt. %, from about 1 wt. % to about 15 wt. %, from about 1 wt. % to about 10 wt. %, from about 5 wt. % to about 30 wt. %, from about 5 wt. % to about 25 wt. %, from about 5 wt. % to about 20 wt. %, from about 5 wt. % to about 15 wt. %, from about 5 wt. % to about 10 wt. %, from about 10 wt. % to about 30 wt. %, from about 10 wt. % to about 25 wt. %, from about 10 wt. % to about 20 wt. %, or from about 10 wt. % to about 15 wt. %.

13. The aqueous herbicidal concentrate composition of claim 1 wherein the weight ratio of acetamide herbicide to auxin herbicide (acid equivalent basis) is from about 1:

30 to about 30;

1, from about 1;

20 to about 20;

1, from about 1;

10 to about 10;

1, from about 1;

8 to about 8;

1, from about 1;

5 to about 5;

1, from about 1;

1 to about 30;

1, from about 1;

1 to about 20;

1, from about 1;

1 to about 10;

1, from about 1;

1 to about 8;

1, from about 1;

1 to about 5;

1, from about 1;

1 to about 3;

1, from about 2;

1 to about 30;

1, from about 2;

1 to about 20;

1, from about 2;

1 to about 10;

1, from about 2;

1 to about 8;

1, from about 2;

1 to about 5;

1, from about 2;

1 to about 3;

1, from about 1;

1.5 to about 30;

1, from about 1;

1.5 to about 20;

1, from about 1;

1.5 to about 15;

1, from about 1;

1.5 to about 10;

1, from about 1;

1.5 to about 8;

1, from about 1;

1.5 to about 5;

1, or from about 1;

1.5 to about 3;

1.

14. The aqueous herbicidal concentrate composition of claim 1 further comprising one or more additional co-herbicides.

15. The aqueous herbicidal concentrate composition of claim 14 wherein the additional co-herbicide is selected from acetyl CoA carboxylase inhibitors, enolpyruvyl shikimate-3-phosphate synthase inhibitors, glutamine synthetase inhibitors, photosystem II inhibitors, acetolactate synthase or acetohydroxy acid synthase inhibitors, photosystem I inhibitors, mitosis inhibitors, protoporphyrinogen oxidase inhibitors, cellulose inhibitors, oxidative phosphorylation uncouplers, dihydropteroate synthase inhibitors, fatty acid and lipid biosynthesis inhibitors, auxin transport inhibitors and carotenoid biosynthesis inhibitors, salts and esters thereof, racemic mixtures and resolved isomers thereof, and mixtures thereof.

16. The aqueous herbicidal concentrate composition of claim 14 wherein the additional co-herbicide comprises glyphosate, or a salt or ester thereof.

17. The aqueous herbicidal concentrate composition of claim 14 wherein the additional co-herbicide comprises glufosinate or glufosinate-P, or a salt or ester thereof.

18. The aqueous herbicidal concentrate composition of claim 14 wherein the additional co-herbicide comprises an acetyl CoA carboxylase inhibitor selected from the group consisting of alloxydim, butroxydim, clethodim, cycloxydim, pinoxaden, sethoxydim, tepraloxydim, tralkoxydim, chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenthiaprop, fluazifop, haloxyfop, isoxapyrifop, metamifop, propaquizafop, quizalofop and trifop, salts and esters thereof, and mixtures thereof.

19. The aqueous herbicidal concentrate composition of claim 14 wherein the additional co-herbicide comprises a photosystem II inhibitor selected from the group consisting of ametryn, amicarbazone, atrazine, bentazon, bromacil, bromoxynil, chlorotoluron, cyanazine, desmedipham, desmetryn, dimefuron, diuron, fluometuron, hexazinone, ioxynil, isoproturon, linuron, metamitron, methibenzuron, metoxuron, metribuzin, monolinuron, phenmedipham, prometon, prometryn, propanil, pyrazon, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine and trietazine, salts and esters thereof, and mixtures thereof.

20. The aqueous herbicidal concentrate composition of claim 14 wherein the additional co-herbicide comprises an acetolactate synthase or acetohydroxy acid synthase inhibitor selected from the group consisting of amidosulfuron, azimsulfruon, bensulfuron-methyl, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florazulam, flucarbazone, flucetosulfuron, flumetsulam, flupyrsulfuron-methyl, foramsulfuron, halosulfuron-methyl, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, metsulfuron-methyl, nicosulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrithiobac, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron and triflusulfuron-methyl, salts and esters thereof, and mixtures thereof.

21. The aqueous herbicidal concentrate composition of claim 14 wherein the additional co-herbicide comprises a protoporphyrinogen oxidase inhibitor selected from the group consisting of acifluorfen, azafenidin, bifenox, butafenacil, carfentrazone-ethyl, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluthiacet-methyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pyraflufen-ethyl, saflufenacil and sulfentrazone, salts and esters thereof, and mixtures thereof.

22. The aqueous herbicidal concentrate composition of claim 14 wherein the additional co-herbicide is selected from the group consisting of glyphosate, glufosinate, flumioxazin, fomesafen, lactofen, sulfentrazone, oxyfluorfen, saflufenacil, metribuzin, thiencarbazone, mesotrione, atrazine, flumetsulam, isoxaflutole, and fluometuron, salts and esters thereof, racemic mixtures and resolved isomers thereof, and mixtures thereof.

23. The aqueous herbicidal concentrate composition of claim 14 wherein the additional co-herbicide comprises fomesafen or salt thereof.

24. The aqueous herbicidal concentrate composition of claim 14 wherein the additional co-herbicide comprises metribuzin.

25. The aqueous herbicidal concentrate composition of claim 1 further comprising a release modulating agent comprising a polyvalent metal cation, wherein the molecular weight of the release modulating agent is no greater than about 1000 g/mol.

26. An aqueous herbicidal concentrate composition comprising:

(a) at least one particulate microencapsulated acetamide herbicide dispersed in an aqueous liquid medium comprising a water-immiscible core material comprising the acetamide herbicide and a polyurea shell wall containing the core material, wherein the acetamide herbicide concentration in the composition on an active ingredient basis is at least about 10 wt. %, and wherein the polyurea shell wall is formed in a polymerization medium by a polymerization reaction between a polyisocyanate component comprising a polyisocyanate or mixture of polyisocyanates and a polyamine component comprising a polyamine or mixture of polyamines to form the polyurea and wherein the ratio of amine molar equivalents contained in the polyamine component to isocyanate molar equivalents contained in the polyisocyanate component is at least 1.01;

1; and

(b) a release modulating agent comprising a polyvalent metal cation, wherein the molecular weight of the release modulating agent is no greater than about 1000 g/mol, and

wherein the ratio of moles of polyvalent metal cation to amine molar equivalents contained in the polyamine component is from about 0.05;

1 to about 10;

1.

27-72. -72. (canceled)

73. A liquid herbicidal mixture comprising:

(a) at least one particulate microencapsulated acetamide herbicide dispersed in an aqueous liquid medium comprising a water-immiscible core material comprising the acetamide herbicide and a polyurea shell wall containing the core material;

(b) a release modulating agent comprising a polyvalent metal cation, wherein the molecular weight of the release modulating agent is no greater than about 1000 g/mol; and

(c) an acidic co-herbicide.