WO2011095859A4 - An improved formulation - Google Patents

An improved formulation Download PDF

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Publication number
WO2011095859A4
WO2011095859A4 PCT/IB2011/000144 IB2011000144W WO2011095859A4 WO 2011095859 A4 WO2011095859 A4 WO 2011095859A4 IB 2011000144 W IB2011000144 W IB 2011000144W WO 2011095859 A4 WO2011095859 A4 WO 2011095859A4
Authority
WO
WIPO (PCT)
Prior art keywords
acid
formulation
wall
forming component
organic
Prior art date
Application number
PCT/IB2011/000144
Other languages
French (fr)
Other versions
WO2011095859A1 (en
Inventor
Jaidev Rajnikant Shroff
Vikram Rajnikant Shroff
Prakash Mahadev Jadhav
Christian Becker
Original Assignee
United Phosphorus Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to RU2012137132/13A priority Critical patent/RU2529729C2/en
Priority to DK11739456.9T priority patent/DK2531023T3/en
Priority to US13/576,181 priority patent/US9288979B2/en
Priority to CN201180008250.4A priority patent/CN102770023B/en
Priority to BR112012019430-5A priority patent/BR112012019430B1/en
Priority to UAA201210303A priority patent/UA108372C2/en
Application filed by United Phosphorus Limited filed Critical United Phosphorus Limited
Priority to EP11739456.9A priority patent/EP2531023B1/en
Priority to AU2011212201A priority patent/AU2011212201B2/en
Priority to ES11739456.9T priority patent/ES2573430T3/en
Publication of WO2011095859A1 publication Critical patent/WO2011095859A1/en
Publication of WO2011095859A4 publication Critical patent/WO2011095859A4/en
Priority to US15/057,745 priority patent/US10342230B2/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • A01N33/18—Nitro compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
    • A01N25/28—Microcapsules or nanocapsules

Abstract

A microencapsulated formulation of pendimethalin comprising an alkali or an alkaline earth metal salt of an organic acid. Also described are processes for the preparation of the formulation and a method of controlling weeds at a locating by using the described formulation.

Claims

AMENDED CLAIMS
received by the International Bureau on
17 August 201 1 (17.08.201 1 )
1. A capsule suspension formulation of pendimethalin comprising a herbicidally effective amount of microencapsulated pendimethalin, the microcapsules comprising said herbicidally effective amount of pendimethalin being encapsulated within a polymeric wall, said polymeric wall being in-situ formed by an interfacial polymerization reaction occurring between a first phase dispersed in a second phase, at least one of said first and second phases being characterized in comprising a predefined amount of at least one alkali or alkaline earth metal salt of an organic acid, wherein said organic acid is selected from acetic acid, propionic acid, citric acid, fumaric acid, tartaric acid, oxalic acid, succinic acid, valeric acid, malonic acid, glutaric acid, adipic acid and phthalic acid.
2. The formulation as claimed in claim 1, having a reduced staining property over an encapsulated pendimethalin formulation comprising an inorganic salt.
3. The formulation as claimed in claim 1 or claim 2, wherein said first and second phases are immiscible with each other.
4. The formulation as claimed in any one of the preceding claims, wherein said first phase is an organic phase dispersed in said second phase.
5. The formulation as claimed in claim 4, wherein said second phase is an aqueous phase.
6. The formulation as claimed in any one of the preceding claims, wherein said polymeric wall is selected from polyurea, polyurethane, polyamide, polycarbonate, polysulfonamide and crosslinked or non-crosslinked combinations thereof. /. he formulation as claimed in claim 6, wherein the capsule polymeric wall is a polyurea wall.
8. The formulation as claimed in any one of the preceding claims, wherein said polymeric wall is formed by an interfacial polymerization triggered by contacting a first wall forming component with a second wall forming component.
9. The formulation as claimed in claim 8, wherein said first and second wall forming components, being same or different, are included within at least one of said first and second phases.
10. The formulation as claimed in claim 8, wherein said first wall forming component is selected from polyisocyanate, polyacid chloride, polychloroformate and polysulfonyl chloride.
11. The formulation as claimed in any one of claims 8-10, wherein said second wall forming component is selected from polyamine and polyol.
12. The formulation as claimed in claim 10, wherein said first wall forming component is a polyisocyanate selected from tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, toluene diisocyanate, diphenylmethene- 4,4'-diisocyanate, polymethylene polyphenylene isocyanate, 2,4,4'-diphenyl ether triisocyanate, 3,3'-dimethyl-4,4'-diphenyl diisocyanate, 3,3'-dimethoxy-4,4'-diphenyl diisocyanate, 1,5-naphthylene diisocyanate and 4,4'4"-triphenytmethane triisocyanate.
13. The formulation as claimed in claim 11, wherein said second wall forming component is a polyamine selected from ethylenediamine, propylene- 1,3-diamine, tetramethylenediamine, pentamethylenediamine, 1 ,6-hexamethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, 4,9-dioxadodecane-l, 12-diamine, 1,3-phenylenediamine, 2,4- and 2,6-toluenediamine and 4,4'-diaminodiphenylmethane or acid addition salt thereof.
14. The formulation as claimed in any one of the preceding claims, wherein said first wall forming component is present in an amount of about 0.1% to about 20% by weight of the organic phase.
15. The formulation as claimed in any one of the preceding claims, wherein said second wall forming component is present in an amount of about 0.3% to 7.5% by weight relative to the total weight of the formulation.
16. The formulation as claimed in claim 7, wherein said polyurea shell wall is formed by a self-condensation reaction of a polyisocyanate wall forming component.
17. The formulation as claimed in claim 1 , wherein said alkali or alkaline earth metal moiety of said alkali or alkaline earth metal salt of an organic acid is selected from sodium and potassium.
18. The formulation as claimed in any one of the preceding claims, wherein said alkali or alkaline earth metal salt of an organic acid is sodium acetate or disodium succinate.
19. The formulation as claimed in any one of the preceding claims comprising 0.2% to about 5% by weight of a surfactant selected from ethoxylated lignosulfonic acid salts, lignosulfonic acid salts, oxidized lignins, lignin salts, salts of styrene-maleic anhydride copolymers, polyvinyl alcohol, salts of partial esters of styrene-maleic anhydride copolymers, partial salts of polyacrylic acid and partial salts of polyacrylic acid terpolymers.
20. The formulation as claimed in any one of the preceding claims wherein said alkali or alkaline earth metal salt of an organic acid or mixtures thereof is present in an amount of from about 2% to about 55% by weight of the formulation.
21. The formulation as claimed in any one of the preceding claims comprising from about 5% to about 60% of pendimethalin active ingredient.
22. The formulation as claimed in any one of the preceding claims, wherein said polymeric shell wall constitutes from about 1% by weight to about 20% by weight of the formulation.
23. The formulation as claimed in any one of the preceding claims, wherein said microcapsules have a particle size of about 2 micrometers to about 50 micrometers.
24. The formulation as claimed in any one of the preceding claims, additionally comprising at least one excipient selected from an anti-foam in an amount of about 0.01% to about 5% by weight of the formulation, a rheology modifier in an amount of about 0.01% to about 3% by weight of the formulation, a mineral acid from about 0.1% to about 10% by weight of the formulation and a biocide in an amount of from about 0.01% to about 3% by weight of the formulation.
25. A process for the preparation of a capsule suspension formulation, said process comprising:
a. forming an aqueous solution comprising at least one surfactant and a predefined amount of at least one alkali or alkaline earth metal salt of an organic acid, wherein said organic acid is selected from acetic acid, propionic acid, citric acid, fumaric acid, tartaric acid, oxalic acid, succinic acid, valeric acid, malonic acid, glutaric acid, adipic acid and phthalic acid;
b. forming an organic phase by melting a herbicidally effective amount of pendimethalin active ingredient and adding a predetermined amount of polyisocyanate wall forming component;
c. dispersing said organic phase in said aqueous solution to obtain an emulsion to form an interface between the discrete droplets of organic phase and the aqueous phase; and d. maintaining said emulsion for a sufficient period of time to allow substantial completion of the self-polymerization reaction of polyisocyanate such that said liquid droplets in the organic phase are converted to capsules comprising polyurea shells enclosing pendimethalin active ingredient.
26. The process as claimed in claim 25, wherein said polymeric shell wall is polyurea wall formed by a self-condensation reaction of a polyisocyanate wall forming component.
27. The process as claimed in claim 25 or claim 26, wherein said emulsion of said organic phase in said aqueous solution is heated to a temperature of between 20°C to about 100°C.
28. The process as claimed in any one of the claims 25-27, wherein the polymeric shell wall is formed by dispersing the organic phase droplets in the continuous aqueous phase to form an emulsion followed by heating the emulsion resulting therefrom; or heating the continuous aqueous phase and dispersing the organic phase droplets in the heated continuous aqueous phase to form the emulsion thereby effecting the desired self-condensation reaction at the interface between the organic droplets and the aqueous phase.
29. A process for the preparation of a capsule suspension formulation, said process comprising:
a. forming an aqueous solution comprising at least one surfactant and a predefined amount of at least one alkali or alkaline earth metal salt of an organic acid, wherein said organic acid is selected from acetic acid, propionic acid, citric acid, fumaric acid, tartaric acid, oxalic acid, succinic acid, valeric acid, malonic acid, glutaric acid, adipic acid and phthalic acid; b. forming an organic phase by melting a herbicidally effective amount of pendimethalin active ingredient and adding a predetermined amount of a first wall component to said organic phase;
c. dispersing said organic phase in said aqueous solution to obtain an emulsion; and
d. adding a second wall forming component to said emulsion such that said second wall forming component reacts with said first wall forming component comprised within said emulsion to polymeric wall encapsulating at least said herbicidally effective amount of pendimethalin active ingredient.
30. The process as claimed in claim 29, wherein said first wall forming component is added to molten pendimethalin while stirring.
31. The process as claimed in claim 29 or claim 30 additionally comprising neutralizing the reaction mixture with an inorganic acid.
32. The process as claimed in any of the claims 29-31, wherein the step of adding a second wall forming component to the emulsion is carried out at a temperature of about 35°C to about 85°C.
33. A method for controlling undesirable plant species at a locus, said method comprising applying to the desired locus a herbicidally effective amount of a microencapsulated pendimethalin formulation as claimed in claims 1-24 or a capsule suspension formulation obtainable by the process claimed in claims 25-32.

STATEMENT UNDER ARTICLE 19

PCT International Application No. PCT/IB2011/000144

International Filing Date: January 31, 2011

Applicant: UNITED PHOSPHORUS LIMITED

Title: "AN IMPROVED FORMULATION"

Priority: 284/MUM/2010 dated 03/02/2010

Agents' File Ref.: FPAA2399PCT

The applicant respectfully acknowledges the Written Opinion of the International Searching Authority, Australia that the originally filed claims 16, 17, 19 and 26-33 are novel, involve an inventive step and are capable of industrial application.

The independent claim 1 and the renumbered process directed independent claims 25 and 29 now recite the organic acids recited in the original claim 17. The Written Opinion of the International Searching Authority acknowledges the original claim 17 as being novel and involving an inventive step, which is now merged into the independent claims 1 , 25 and 29. The remaining claims now depend upon these independent claims. Accordingly, by logical extension, all the claims being presented herewith in the amended set of claims must be acknowledged to be directed to subject matter that is both novel and involves an inventive step.

Even otherwise, none of the cited prior art references, either alone or in combination, suggests that the presence of an alkali or an alkaline earth metal salt of an organic acid recited in the claims would (i) provide a substantially non-staining formulation vis-a-vis the conventionally known formulations; (ii) reduce or eliminate phytotoxicity; (c) enhance the suspension stability of the formulation; (iv) prevent the early rupture of the polymeric capsule wall; and (v) not corrode the container. Therefore, at least for this reason, the inventiveness of the amended claims being presented herewith must be acknowledged.

The amended claims annexed hereto may kindly be taken as amended claims under Article 19 of the PCT.

PCT/IB2011/000144 2010-02-03 2011-01-31 An improved formulation WO2011095859A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DK11739456.9T DK2531023T3 (en) 2010-02-03 2011-01-31 improved formulation
US13/576,181 US9288979B2 (en) 2010-02-03 2011-01-31 Microencapsulated pendimethalin comprising alkali or alkaline earth metal salt of organic acid
CN201180008250.4A CN102770023B (en) 2010-02-03 2011-01-31 An improved formulation
BR112012019430-5A BR112012019430B1 (en) 2010-02-03 2011-01-31 PENDIMENTALINE CAPSULE SUSPENSION FORMULATION, PROCESS FOR PREPARING CAPSULE SUSPENSION FORMULATION AND DESIRED VEGETABLE CONTROL METHOD
UAA201210303A UA108372C2 (en) 2010-02-03 2011-01-31 COMPOSITION OF PENDIMETHALINE Capsular SUSPENSION, METHOD OF ITS PREPARATION AND METHOD OF FIGHTING UNWANTED PLANTS
RU2012137132/13A RU2529729C2 (en) 2010-02-03 2011-01-31 Improved composition of pendimethalin capsule suspension, method of obtaining said composition (versions) and method of controlling undesirable species of plants
EP11739456.9A EP2531023B1 (en) 2010-02-03 2011-01-31 An improved formulation
AU2011212201A AU2011212201B2 (en) 2010-02-03 2011-01-31 An improved formulation
ES11739456.9T ES2573430T3 (en) 2010-02-03 2011-01-31 An improved formulation
US15/057,745 US10342230B2 (en) 2010-02-03 2016-03-01 ZC composition comprising microencapsulated pendimethalin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN284MU2010 2010-02-03
IN284/MUM/2010 2010-02-03

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US13/576,181 A-371-Of-International US9288979B2 (en) 2010-02-03 2011-01-31 Microencapsulated pendimethalin comprising alkali or alkaline earth metal salt of organic acid
US15/057,745 Continuation-In-Part US10342230B2 (en) 2010-02-03 2016-03-01 ZC composition comprising microencapsulated pendimethalin

Publications (2)

Publication Number Publication Date
WO2011095859A1 WO2011095859A1 (en) 2011-08-11
WO2011095859A4 true WO2011095859A4 (en) 2011-10-13

Family

ID=44355014

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2011/000144 WO2011095859A1 (en) 2010-02-03 2011-01-31 An improved formulation

Country Status (11)

Country Link
US (1) US9288979B2 (en)
EP (1) EP2531023B1 (en)
CN (1) CN102770023B (en)
AU (1) AU2011212201B2 (en)
BR (1) BR112012019430B1 (en)
DK (1) DK2531023T3 (en)
ES (1) ES2573430T3 (en)
HU (1) HUE028432T2 (en)
RU (1) RU2529729C2 (en)
UA (1) UA108372C2 (en)
WO (1) WO2011095859A1 (en)

Families Citing this family (12)

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CA2842763C (en) * 2011-08-10 2018-10-16 Upl Limited Capsule suspension formulation comprising polymeric wall encapsulated pendimethalin and clomazone
WO2014078642A1 (en) * 2012-11-16 2014-05-22 Basf Se An encapsulated fertilizer particle containing pesticide
ES2800074T3 (en) 2015-06-19 2020-12-23 Basf Se Pendimethalin microcapsules with a shell made of tetramethylxilylene diisocyanate and a polyamine with at least three amine groups
CR20180046A (en) 2015-06-19 2018-04-30 Basf Se PESTICIDED MICROCAPPS WITH A COATING MADE OF TETRAMETILYXYLYLENE DIISOCIANATE, CYCLALIPHYTIC DIISOCIANATE AND ALIPHATIC DIAMINE
CN105409997A (en) * 2015-12-24 2016-03-23 安徽美兰农业发展股份有限公司 Pyrazosulfuron-ethyl and pendimethalin compounded wettable powder and preparation method thereof
CR20220024A (en) * 2016-01-21 2022-02-22 Upl Ltd An improved herbicidal formulation
CN105875607B (en) * 2016-05-16 2018-07-03 中国农业大学 A kind of Pendimethalin microcapsule suspending agent and preparation method thereof
CN107027774B (en) * 2017-06-12 2018-09-18 南京高正农用化工有限公司 A kind of ternary weeding composition containing Pendimethalin
CN107950525A (en) * 2017-10-31 2018-04-24 华南理工大学 A kind of fertilizer microcapsules and preparation method and application
WO2020051244A1 (en) * 2018-09-05 2020-03-12 The Regents Of The University Of California Microencapsulation of chemicals and bioactives by in situ complex coacervation during spray drying
CN109497061A (en) * 2018-12-21 2019-03-22 江苏精禾界面科技有限公司 A kind of pendimethalin microcapsule suspending agent and preparation method thereof
CN114747583A (en) * 2022-05-19 2022-07-15 北京傲锐科技有限公司 Plant growth inhibitor composition and application thereof

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ATE156728T1 (en) * 1992-01-03 1997-08-15 Ciba Geigy Ag SUSPENSION OF MICRO CAPSULES AND METHOD FOR THE PRODUCTION THEREOF
US5705174A (en) * 1995-06-07 1998-01-06 American Cyanamid Company Process for the preparation of microcapsule compositions
US6022501A (en) * 1996-08-15 2000-02-08 American Cyanamid Company pH-sensitive microcapsules
BR9913057A (en) * 1998-08-18 2001-10-09 Fmc Corp Process for encapsulating clomazone and a second agricultural agent, agricultural composition and, process for preparing the same
ATE347263T1 (en) 2002-07-22 2006-12-15 Basf Ag METHODS OF USING DINITROANILINE COMPOUNDS AS MICROCAPSULATION FORMULATIONS
SI1622447T1 (en) 2003-04-14 2010-10-29 Basf Se An aqueous, flowable concentrate composition of pendimethalin
MY146405A (en) * 2005-03-01 2012-08-15 Basf Ag Fast-release microcapsule products
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Also Published As

Publication number Publication date
EP2531023A4 (en) 2013-08-21
CN102770023A (en) 2012-11-07
AU2011212201A1 (en) 2012-08-16
WO2011095859A1 (en) 2011-08-11
RU2529729C2 (en) 2014-09-27
BR112012019430B1 (en) 2018-06-05
DK2531023T3 (en) 2016-06-27
ES2573430T3 (en) 2016-06-07
EP2531023B1 (en) 2016-03-23
BR112012019430A2 (en) 2015-09-22
UA108372C2 (en) 2015-04-27
RU2012137132A (en) 2014-03-10
US20120309627A1 (en) 2012-12-06
US9288979B2 (en) 2016-03-22
CN102770023B (en) 2014-10-15
EP2531023A1 (en) 2012-12-12
HUE028432T2 (en) 2016-12-28
AU2011212201B2 (en) 2014-09-25
BR112012019430A8 (en) 2017-10-10

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