Particles containing agricultural active ingredients

• US 7,070,795 B1
• Filed: 06/04/1999
• Issued: 07/04/2006
• Est. Priority Date: 06/30/1997
• Status: Expired due to Term

• Current Assignee: Monsanto Technology LLC (Bayer AG)
• Original Assignee: Monsanto Company (Bayer AG)
• Inventors: Miller, Maria L., Botts, M. Francis, Kohn, Frank C.
• Primary Examiner(s): Levy, Neil S.
• Application Number:
  US09/326,014
• Time in Patent Office: 2,587 Days
• Field of Search: 424/405, 424/407, 424/409, 424/411, 424417-421, 424/78.09, 424484-502, 424/439, 47/576, 514/937, 514950-952, 514/383, 504/272, 523/122
• US Class Current: 424/409
• 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 25/10 Macromolecular compounds
• CPC Class Codes: A01N 25/12 Powders or granules A01N25/26 takes precedence
• CPC Class Codes: A01N 43/653 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Abstract

One or more agricultural active ingredients (such as fungicides or insecticides) are entrapped in polymeric matrixes to form particles having a diameter in the range from about 0.2 to about 200 microns. The particles are applied to soil, to seeds, or to plants and release the active ingredient(s) at a rate sufficiently low to avoid phytoxicity but at a rate sufficiently high to provide effective amounts of the active ingredient(s), preferably throughout the growing period of the plant.

Claims

1. A particle for controlled release of a fungicide, wherein the particle is solid and generally spherical and is from 0.1 to 200 microns in size and comprises a triazole fungicide dispersed in a polymer matrix at a molecular level or as pockets containing a plurality of triazole molecules, wherein the fungicide-to-polymer weight ratio is from about 1:

99 to about 1;

1, wherein the triazole fungicide is selected from the group consisting of bitertanol, bromuconazole, cyproconazole, difenoconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, metconazole, myclobutanil, penconazole, propiconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, and triticonazole, and wherein the polymer matrix comprises a polymer selected from the group consisting of poly(methylmethacrylate), poly(lactic acid), a poly(lactic acid-glycolic acid) copolymer, cellulose acetate butyrate, a poly(styrene), hydroxybutyric acid-hydroxyvaleric acid copolymer, a styrene maleic anhydride copolymer, poly(methylvinyl ether-maleic acid), poly(caprolactone), poly(n-amylmethacrylate), wood rosin, a polyanhydride, a polyorthoester, a poly(cyanoacrylate), poly(dioxanone), ethyl cellulose, a ethyl vinyl acetate polymer, poly(ethylene glycol), poly(vinylpyrrolidone), an acetylated monogylceride, an acetylated digylceride, an acetylated trigylceride, poly(phosphazene), chlorinated natural rubber, a vinyl polymer, polyvinyl chloride, a hydroxyalkylcellulose, polybutadiene, polyurethane, a vinylidene chloride polymer, a styrene-butadiene copolymer, a styrene-acrylic copolymer, an alkylvinylether polymer, a cellulose acetate phthalate, an ethyl vinyl phthalate, cellulose triacetate, a polyanhydride, a polyglutamate, a polyhydroxy butyrate, polyvinyl acetate, a vinyl acetate-ethylene copolymer, a vinyl acetate-vinylpyrrolidone copolymer, an acrylic polymer, an alkyl acrylate polymer, an aryl acrylate polymer, an aryl methacrylate polymer, a poly(caprolactam), an epoxy resin, a polyamine epoxy resin, a polyamide, a polyvinyl alcohol polymer, a polyalkyd resin, a phenolic resin, an abietic acid resin, a silicone, a polyalkylene oxide, and a polyester.

2. A particle according to claim 1, wherein the triazole fungicide is dispersed evenly throughout the polymer matrix.

3. The particle of claim 1 wherein the triazole fungicide comprises a compound selected from the group consisting of cyproconazole, epoxiconazole, tebuconazole, triadimefon, and triadimenol.

4. The particle of claim 3 wherein the triazole fungicide comprises cyproconazole.

5. The particle of claim 3 wherein the triazole fungicide comprises tebuconazole.

6. The particle of claim 1 wherein the triazole fungicide comprises epoxiconazole.

7. A particle according to claim 1, wherein the triazole fungicide is dispersed as a concentration gradient in the polymer matrix.

8. The particle of claim 1 further comprising a plasticizer.

9. A fungicidal composition comprising:

(a) particles that are solid and generally spherical and from 0.1 to 200 microns in size and which comprise a triazole fungicide dispersed in a polymer matrix at a molecular level or as pockets containing a plurality of triazole molecules, wherein the fungicide-to-polymer weight ratio is from about 1;

99 to about 1;

1, wherein the triazole fungicide is selected from the group consisting of bitertanol, bromuconazole, cyproconazole, difenoconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, metconazole, myclobutanil, penconazole, propiconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, and triticonazole, and wherein the polymer matrix comprises a polymer selected from the group consisting of poly(methylmethacrylate), poly(lactic acid), a poly(lactic acid-glycolic acid) copolymer, cellulose acetate butyrate, a poly(styrene), hydroxybutyric acid-hydroxyvaleric acid copolymer, a styrene maleic anhydride copolymer, poly(methylvinyl ether-maleic acid), poly(caprolactone), poly(n-amylmethacrylate), wood rosin, a polyanhydride, a polyorthoester, a poly(cyanoacrylate), poly(dioxanone), ethyl cellulose, a ethyl vinyl acetate polymer, poly(ethylene glycol), poly(vinylpyrrolidone), an acetylated monogylceride, an acetylated digylceride, an acetylated trigylceride, poly(phosphazene), chlorinated natural rubber, a vinyl polymer, polyvinyl chloride, a hydroxyalkylcellulose, polybutadiene, polyurethane, a vinylidene chloride polymer, a styrene-butadiene copolymer, a styrene-acrylic copolymer, an alkylvinylether polymer, a cellulose acetate phthalate, an ethyl vinyl phthalate, cellulose triacetate, a polyanhydride, a polyglutamate, a polyhydroxy butyrate, polyvinyl acetate, a vinyl acetate-ethylene copolymer, a vinyl acetate-vinylpyrrolidone copolymer, an acrylic polymer, an alkyl acrylate polymer, an aryl acrylate polymer, an aryl methacrylate polymer, a poly(caprolactam), an epoxy resin, a polyamine epoxy resin, a polyamide, a polyvinyl alcohol polymer, a polyalkyd resin, a phenolic resin, an abietic acid resin, a silicone, a polyalkylene oxide, and a polyester; and

(b) an agricultural adjuvant.

10. A fungicidal composition according to claim 9, wherein the triazole fungicide is dispersed evenly throughout the polymer matrix.

11. A fungicidal composition according to claim 9, wherein the triazole fungicide is dispersed as a concentration gradient in the polymer matrix.

12. The fungicidal composition of claim 9 wherein the agricultural adjuvant comprises a diluent.

13. The fungicidal composition of claim 9 wherein the fungicidal composition is in the form of a liquid suspension.

14. The fungicidal composition of claim 9 wherein the fungicidal composition is in the form of a wettable powder.

15. The fungicidal composition of claim 9 wherein the fungicidal composition is in the form of a granule.

16. The fungicidal composition of claim 15 wherein the granule is a water-dispersible granule.

17. The fungicidal composition of claim 9 wherein the agricultural adjuvant comprises a dispersant.

18. A method for the treatment or prophylaxis of a fungal disease in a target plant wherein the method comprises contacting a plant cell, a plant tissue, or a seed with particles which are solid and generally spherical and from 0.1 to 200 microns in size and comprise a triazole fungicide dispersed in a polymer matrix at a molecular level or as pockets containing a plurality of triazole molecules, wherein the fungicide-to-polymer weight ratio is from about 1:

99 to about 1;

1, wherein the triazole fungicide is selected from the group consisting of bitertanol, bromuconazole, cyproconazole, difenoconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, metconazole, myclobutanil, penconazole, propiconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, and triticonazole, and wherein the polymer matrix comprises a polymer selected from the group consisting of poly(methylmethacrylate), poly(lactic acid), a poly(lactic acid-glycolic acid) copolymer, cellulose acetate butyrate, a poly(styrene), hydroxybutyric acid-hydroxyvaleric acid copolymer, a styrene maleic anhydride copolymer, poly(methylvinyl ether-maleic acid), poly(caprolactone), poly(n-amylmethacrylate), wood rosin, a polyanhydride, a polyorthoester, a poly(cyanoacrylate), poly(dioxanone), ethyl cellulose, a ethyl vinyl acetate polymer, poly(ethylene glycol), poly(vinylpyrrolidone), an acetylated monogylceride, an acetylated digylceride, an acetylated trigylceride, poly(phosphazene), chlorinated natural rubber, a vinyl polymer, polyvinyl chloride, a hydroxyalkylcellulose, polybutadiene, polyurethane, a vinylidene chloride polymer, a styrene-butadiene copolymer, a styrene-acrylic copolymer, an alkylvinylether polymer, a cellulose acetate phthalate, an ethyl vinyl phthalate, cellulose triacetate, a polyanhydride, a polyglutamate, a polyhydroxy butyrate, polyvinyl acetate, a vinyl acetate-ethylene copolymer, a vinyl acetate-vinylpyrrolidone copolymer, an acrylic polymer, an alkyl acrylate polymer, an aryl acrylate polymer, an aryl methacrylate polymer, a poly(caprolactam), an epoxy resin, a polyamine epoxy resin, a polyamide, a polyvinyl alcohol polymer, a polyalkyd resin, a phenolic resin, an abietic acid resin, a silicone, a polyalkylene oxide, and a polyester.

19. The method of claim 18 comprising contacting a seed with the particle.

20. The method of claim 19 wherein the contacting is performed before the seed is planted.

21. The method of claim 18 wherein the triazole fungicide comprises cyproconazole.

22. The method of claim 18 wherein the triazole fungicide comprises tebuconazole.

23. The method of claim 18 wherein the triazole fungicide comprises epoxiconazole.

24. The method of claim 18 wherein the triazole fungicide comprises triadimenol.

25. The method of claim 18 wherein the triazole fungicide comprises triadimefon.

26. A method according to claim 18, wherein the triazole fungicide is dispersed evenly throughout the polymer matrix.

27. A method according to claim 18, wherein the triazole fungicide is dispersed as a concentration gradient in the polymer matrix.