WO2005104846A1 - Dispersible pesticidal compositions - Google Patents
Dispersible pesticidal compositions Download PDFInfo
- Publication number
- WO2005104846A1 WO2005104846A1 PCT/US2005/012398 US2005012398W WO2005104846A1 WO 2005104846 A1 WO2005104846 A1 WO 2005104846A1 US 2005012398 W US2005012398 W US 2005012398W WO 2005104846 A1 WO2005104846 A1 WO 2005104846A1
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- WO
- WIPO (PCT)
- Prior art keywords
- composition
- sodium
- weight
- mixture
- concentration
- Prior art date
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Classifications
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- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Definitions
- the present invention relates to pesticidal compositions.
- the invention provides a soluble granule formulation of Flonicamid, a water-soluble pesticide, which is easily dispersed in an aqueous medium.
- Soluble granule formulations containing water-soluble pesticides are desirable in agricultural and related endeavors due to ease of handling and the elimination of organic solvents, which can be costly and dangerous to the environment. Safety, specifically eye irritation, caused by solvents, dispersants, clays and wetting agents in traditional formulations are also of concern.
- the process used to make the soluble granule formulation can be conducted in relatively simple equipment using relatively simple process steps.
- the formulation of soluble granule pesticides has been disclosed in the prior art, for example in U.S. Patent 6,387,388 (Misselbrook et al.).
- Challenges in formulating a soluble granule of a water-soluble pesticide include the requirements that the final product successfully achieves (a) good dispersibility/solubility in an aqueous medium and (b) chemical stability once dispersed.
- Good dispersibility/solubility in an aqueous medium is important in a soluble granule formulation since ineffective mixing of the pesticide into solution can result in reduced or inconsistent efficacy and, ultimately, costly returns of product and loss of sales.
- Chemical degradation is also important because there may be no physical sign of the degradation and resultant loss of efficacy until used on a pest. Examples of problematic chemical degradation include hydrolysis, oxidation, dehalogenation and bond cleavage.
- the present invention is directed to a soluble granule composition
- a soluble granule composition comprising Flonicamid, a dispersant, and a wetting agent.
- This soluble granule composition has improved dispersibility/solubility as compared to other formulations.
- Flonicamid refers to N-cyanomethyl-4-trifluoromethyl nicotinamide, or salts thereof.
- pesticide refers to a molecule or combination of molecules that repels, retards, or kills pests, such as, but not limited to, deleterious or annoying insects, weeds, worms, fungi, bacteria, and the like, and can be used for crop protection, edifice protection, turf protection, or protection of a person; pesticide as used herein includes, but is not limited to, herbicides, insecticides, acaricides, fungicides, nematicides, ectoparasiticides, and growth regulators, either used to encourage growth of a desired plant species or retard growth of an undesired pest.
- alkyl cycloalkyl
- alkoxy aryloxy
- alkoxyarylamino used alone or as part of a larger moiety, includes straight or branched chains of at least one or two carbon atoms, as appropriate to the substituent, and preferably up to 20 carbon atoms, more preferably up to ten carbon atoms, most preferably up to seven carbon atoms.
- Halogen or “halo” refers to fluorine, bromine, iodine, or chlorine.
- Aryl refers to an aromatic ring structure having 5 to 10 carbon atoms.
- the term "ambient temperature” as utilized herein shall mean any suitable temperature found in a laboratory or other working environment, and is generally not below about 15° C nor above about 30° C.
- the present invention is directed to a soluble granule composition comprising Flonicamid, a dispersant, and a wetting agent.
- the invention can further comprise a water-soluble carrier.
- Flonicamid can be present in a concentration of from 1 % by weight to 94% by weight, more particularly 45% by weight to 55% by weight, based upon the total weight of all components in the composition.
- the dispersant can be selected from the group consisting of sodium alkyl naphthalene sulfonate formaldehyde condensate, modified acrylate copolymer (sodium salt), alkyl naphthalene sulfonate salts and dodecyl benzene sulfonate (Na) salt.
- the dispersant is sodium alkyl naphthalene sulfonate formaldehyde condensate.
- the dispersant can be present in a concentration of from 0.5% by weight to 20% by weight, more particularly 2% by weight to 6% by weight, based upon the total weight of all components in the composition.
- the wetting agent can be selected from the group consisting of a mixture of sodium dioctylsufosuccinate and sodium benzoate wherein the sodium dioctylsufosuccinate is up to 85 weight percent, polyalkylencoxide modified heptamethyl trisiloxane, alkyloxypolyethylene glycol methyl ether and alcohol (C8- C16) ethoxylates with 3 - 20 moles of ethylene oxide.
- the wetting agent is a mixture of sodium dioctylsufosuccinate and sodium benzoate wherein the sodium dioctylsufosuccinate is present in a concentration up to 85 weight percent.
- the wetting agent can be present in a concentration of from 0.1% by weight to 20% by weight, more particularly 0.5% by weight to 3% by weight, based upon the total weight of all components in the composition.
- the water-soluble carrier can be selected from the group consisting of lactose, sucrose, glucose, starch, sodium tripolyphosphate and water-soluble salts. Preferably, the water-soluble carrier is lactose.
- the water-soluble carrier can be present in a concentration of from 0.001% by weight to 97% by weight, more particularly 35% by weight to 45% by weight, based upon the total weight of all components in the composition.
- Another embodiment of the present invention is a soluble granule composition
- Flonicamid a dispersant selected from the group consisting of sodium alkyl naphthalene sulfonate formaldehyde condensate, modified acrylate copolymer (sodium salt), alkyl naphthalene sulfonate salts and dodecyl benzene sulfonate (Na) salt
- a wetting agent selected from the group consisting of a mixture of sodium dioctylsufosuccinate and sodium benzoate wherein the sodium dioctylsufosuccinate is present in a concentration up to 85 weight percent, polyalkylencoxide modified heptamethyl trisiloxane, alkyloxypolyethylene glycol methyl ether and alcohol (C8- C16) ethoxylates with 3 - 20 moles of ethylene oxide; and a water-soluble carrier selected from the group consisting of lac
- Another embodiment of the present invention is a soluble granule composition
- a soluble granule composition comprising from 1% to 94% of Flonicamid, from 0.5% to 20% of sodium alkyl naphthalene sulfonate formaldehyde condensate, from 0.1% to 20% of a mixture of sodium dioctylsufosuccinate and sodium benzoate wherein the sodium dioctylsufosuccinate is present in a concentration up to 85%, and from 0.001% to 97% of lactose, wherein all % are % by weight based upon the total weight of all components in the composition.
- Yet another embodiment of the present invention is a soluble granule composition
- a soluble granule composition comprising from 25% to 88% of Flonicamid, from 0.5% to 20% of sodium alkyl naphthalene sulfonate formaldehyde condensate, from 0.4% to 5.0% of a mixture of sodium dioctylsufosuccinate and sodium benzoate wherein the sodium dioctylsufosuccinate is present in a concentration up to 85%, and from 6% to 70% of lactose, wherein all % are % by weight based upon the total weight of all components in the composition.
- Yet another embodiment of the present invention is a soluble granule composition
- a soluble granule composition comprising from 45% to 55% of Flonicamid, from 2% to 6% of sodium alkyl naphthalene sulfonate formaldehyde condensate, from 0.5% to 3% of a mixture of sodium dioctylsufosuccinate and sodium benzoate wherein the sodium dioctylsufosuccinate is present in a concentration up to 85%, and from 35% to 45% of lactose, wherein all % are % by weight based upon the total weight of all components in the composition.
- the composition may further comprise an anti-foam agent and/or an anti- bacteria agent.
- the present invention also encompasses a method of controlling unwanted pests, comprising applying to an area infested with such pests an effective amount of the soluble granule composition, discussed above, in an aqueous solvent.
- the present invention also encompasses a process for preparing the soluble granule composition comprising a) forming a mixture of Flonicamid, a dispersant, a wetting agent and, optionally, a water-soluble carrier; b) kneading the mixture; c) extruding the kneaded mixture from step b); and d) drying the extruded mixture from step c).
- the process further comprises milling the mixture prior to kneading.
- testing to demonstrate the dispersibility/solubility of the composition was carried out in the following manner: 1) At ambient temperature, 1.0 gram of the composition prepared in the example was added to 100 ml of water in a cylinder of appropriate size; 2) the cylinder was repeatedly inverted 180 degrees to effect dispersion/solution of the composition into the water; 3) the number of inversions required for full dispersion/solution to a clear state was determined visually and recorded. The results of these tests are presented in each example.
- Example 1 This example illustrates the preparation of a 50SG composition (Composition A) of the present invention.
- Composition A A mixture of 52.0 grams of Flonicamid, 5.0 grams of sodium alkylnaphthalene sulfonate formaldehyde condensate, 1.0 gram of a combination of sodium dioctylsufosuccinate and sodium benzoate (Aerosol OTB available from Cytec Industries, Inc. in West Paterson, NI) and 42.0 grams of lactose were combined and agitated under high shear. To this mixture was added 14.0 grams of water and then the mixture was kneaded in a Hobart mixer for about 2 minutes.
- composition A required 3 inversions for full dispersion into a clear solution.
- Example 2 This example illustrates the preparation of a 50SG composition (Composition
- composition B required 8 inversions for full dispersion into a clear solution.
- Example 3 This example illustrates the preparation of a 50SG composition (Composition 1)
- Example 4 This example illustrates the preparation of a 24SG composition (Composition D) of the present invention.
- Composition D A mixture of 25.0 grams of Flonicamid, 5.0 grams of sodium alkylnaphthalene sulfonate formaldehyde condensate, 0.5 gram of a combination of sodium dioctylsufosuccinate and sodium benzoate (Aerosol OTB available from Cytec Industries, Inc. in West Paterson, NI), 68.45 grams of lactose, 1.0 gram of an anti- bacteria agent (Dowcide A available from Dow Chemical Company in Midland Michigan) and 0.05 gram of an anti-foam agent were combined and agitated under high shear.
- composition D required 5 inversions for full dispersion into a clear solution.
- Example 5 This example illustrates the preparation of a 24SG composition (Composition
- composition E required 3 inversions for full dispersion into a clear solution.
- Example 6 This example illustrates the preparation of an 85SG composition (Composition
- Example 7 This example illustrates the preparation of a 50SG composition (Composition
- G of the present invention.
- composition H This example illustrates the preparation of a 70SG composition (Composition H) of the present invention.
- a mixture of 72.0 grams of Flonicamid, 5.0 grams of sodium alkylnaphthalene sulfonate formaldehyde condensate, 1.0 gram of a combination of sodium dioctylsufosuccinate and sodium benzoate (Aerosol OTB available from Cytec Industries, Inc. in West Paterson, NI) and 22.0 grams of lactose were combined and agitated under high shear.
- Example 9 This example illustrates the preparation of a 91SG composition (Composition I) of the present invention.
- Composition I A mixture of 94.0 grams of Flonicamid, 5.0 grams of sodium alkylnaphthalene sulfonate formaldehyde condensate and 1.0 gram of a combination of sodium dioctylsufosuccinate and sodium benzoate (Aerosol OTB available from Cytec
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NZ550372A NZ550372A (en) | 2004-04-14 | 2005-04-13 | Dispersible pesticidal compositions |
EP05736085A EP1734822A4 (en) | 2004-04-14 | 2005-04-13 | Dispersible pesticidal compositions |
CA2563261A CA2563261C (en) | 2004-04-14 | 2005-04-13 | Dispersible pesticidal compositions |
US11/578,005 US8227493B2 (en) | 2004-04-14 | 2005-04-13 | Dispersible pesticidal compositions |
MXPA06011760A MXPA06011760A (en) | 2004-04-14 | 2005-04-13 | Dispersible pesticidal compositions. |
AU2005237438A AU2005237438B2 (en) | 2004-04-14 | 2005-04-13 | Dispersible pesticidal compositions |
BRPI0509858-0A BRPI0509858A (en) | 2004-04-14 | 2005-04-13 | soluble granule composition, method for controlling unwanted pests, and process for preparing a soluble granule composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US56207104P | 2004-04-14 | 2004-04-14 | |
US60/562,071 | 2004-04-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005104846A1 true WO2005104846A1 (en) | 2005-11-10 |
Family
ID=35241366
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2005/012398 WO2005104846A1 (en) | 2004-04-14 | 2005-04-13 | Dispersible pesticidal compositions |
Country Status (11)
Country | Link |
---|---|
US (1) | US8227493B2 (en) |
EP (1) | EP1734822A4 (en) |
AU (1) | AU2005237438B2 (en) |
BR (1) | BRPI0509858A (en) |
CA (1) | CA2563261C (en) |
CR (1) | CR8688A (en) |
EC (1) | ECSP066923A (en) |
MX (1) | MXPA06011760A (en) |
NZ (1) | NZ550372A (en) |
WO (1) | WO2005104846A1 (en) |
ZA (1) | ZA200608450B (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009275036A (en) * | 2008-04-17 | 2009-11-26 | Ishihara Sangyo Kaisha Ltd | Harmful organism control agent composition and method for controlling harmful organism |
CN102228028A (en) * | 2011-05-30 | 2011-11-02 | 青岛海利尔药业有限公司 | Pesticide composition containing sulfur-fluorine oxime ether and part of amide pesticides |
CN104012539A (en) * | 2014-05-14 | 2014-09-03 | 青岛瀚生生物科技股份有限公司 | Compound insecticide containing flonicamid and tetrchlorantraniliprole |
CN104837344A (en) * | 2012-12-06 | 2015-08-12 | 石原产业株式会社 | Oil-based pesticidal suspension |
US9253981B2 (en) | 2006-10-17 | 2016-02-09 | Fmc Corporation | Stable suspension concentrate formulation for water-soluble compounds |
WO2017133868A1 (en) * | 2016-02-02 | 2017-08-10 | Evonik Degussa Gmbh | Powdery formulations with surface active substances on solid, water-soluble carriers, method for the production and use thereof |
CN107212018A (en) * | 2017-03-02 | 2017-09-29 | 华南农业大学 | A kind of composition pesticide of suitable drip irrigation |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2006254199B2 (en) * | 2005-06-02 | 2011-07-28 | Akzo Nobel N.V. | Synergistic blends of (alkyl) naphthalene formaldehyde condensate sulfonates and lignosulfonates useful in agrochemical formulations |
MY165281A (en) * | 2010-07-29 | 2018-03-21 | Ishihara Sangyo Kaisha | Copulation Disruption Agent for Sap-Sucking Pests |
CN108184835B (en) | 2018-01-17 | 2019-07-26 | 重庆岭石农业科技有限公司 | Acaricide and its application |
CN110074115A (en) * | 2019-05-24 | 2019-08-02 | 安徽省益农化工有限公司 | A kind of insecticide dry suspending agent and its processing method |
CN114711244B (en) * | 2021-01-04 | 2024-03-12 | 顺毅股份有限公司 | Composite dispersing agent and application thereof in preparation of water dispersible granule |
Citations (1)
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US5360806A (en) * | 1992-07-23 | 1994-11-01 | Ishihara Sangyo Kaisha Ltd. | Amide compounds and their salts and pesticidal compositions containing them |
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US3986979A (en) * | 1969-05-15 | 1976-10-19 | Westvaco Corporation | Process for making combination wetting-dispersing agent |
US4731379A (en) * | 1983-12-07 | 1988-03-15 | H.S.C. Corporation | Flea eradicator |
US4936901A (en) * | 1986-07-09 | 1990-06-26 | Monsanto Company | Formulations of water-dispersible granules and process for preparation thereof |
US5462915A (en) * | 1989-09-28 | 1995-10-31 | Sandoz Ltd. | Process for producing microcapsules |
US5696024A (en) | 1995-06-06 | 1997-12-09 | American Cyanmid | Herbicidal water soluble granular compositions |
WO1997016968A1 (en) | 1995-11-08 | 1997-05-15 | Merck & Co., Inc. | Pesticidal formulation |
CN1915016B (en) * | 1995-11-08 | 2010-12-22 | 默沙东公司 | Pesticidal formulation |
ATE272104T1 (en) * | 1998-05-18 | 2004-08-15 | Ciba Sc Holding Ag | WATER SOLUBLE GRANULES OF PHTHALOCYANINE COMPOUNDS |
US6855327B1 (en) * | 1998-07-02 | 2005-02-15 | Cognis Corporation | Pesticide dispersant |
CO5210943A1 (en) * | 1999-05-04 | 2002-10-30 | Novartis Ag | PESTICIDE COMPOUNDS DERIVED FROM TRIAZINE, COMPOSITIONS FOR THE CONTROL OF PESTS THAT UNDERSTAND SUCH COMPOUND AND WHEN LESS THAN AN AUXILIARY AND METHODS FOR CONTROLLING PESTS |
-
2005
- 2005-04-13 MX MXPA06011760A patent/MXPA06011760A/en active IP Right Grant
- 2005-04-13 NZ NZ550372A patent/NZ550372A/en unknown
- 2005-04-13 BR BRPI0509858-0A patent/BRPI0509858A/en not_active Application Discontinuation
- 2005-04-13 CA CA2563261A patent/CA2563261C/en active Active
- 2005-04-13 AU AU2005237438A patent/AU2005237438B2/en active Active
- 2005-04-13 US US11/578,005 patent/US8227493B2/en active Active
- 2005-04-13 WO PCT/US2005/012398 patent/WO2005104846A1/en active Application Filing
- 2005-04-13 EP EP05736085A patent/EP1734822A4/en not_active Withdrawn
-
2006
- 2006-10-10 ZA ZA200608450A patent/ZA200608450B/en unknown
- 2006-10-12 CR CR8688A patent/CR8688A/en unknown
- 2006-10-12 EC EC2006006923A patent/ECSP066923A/es unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US5360806A (en) * | 1992-07-23 | 1994-11-01 | Ishihara Sangyo Kaisha Ltd. | Amide compounds and their salts and pesticidal compositions containing them |
Cited By (19)
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US11006630B2 (en) | 2006-10-17 | 2021-05-18 | Fmc Corporation | Stable suspension concentrate formulation for water-soluble compounds |
US9949481B2 (en) | 2006-10-17 | 2018-04-24 | Fmc Corporation | Stable suspension concentrate formulation for water-soluble compounds |
US9253981B2 (en) | 2006-10-17 | 2016-02-09 | Fmc Corporation | Stable suspension concentrate formulation for water-soluble compounds |
US9848601B2 (en) | 2008-04-17 | 2017-12-26 | Ishihara Sangyo Kaisha, Ltd. | Pesticidal composition, and method for controlling pests |
EP2263455A1 (en) * | 2008-04-17 | 2010-12-22 | Ishihara Sangyo Kaisha, Ltd. | Harmful organism control composition, and method for control of harmful organisms |
CN102006774A (en) * | 2008-04-17 | 2011-04-06 | 石原产业株式会社 | Harmful organism control composition, and method for control of harmful organisms |
EP2263455A4 (en) * | 2008-04-17 | 2012-12-19 | Ishihara Sangyo Kaisha | Harmful organism control composition, and method for control of harmful organisms |
AU2009236987B2 (en) * | 2008-04-17 | 2014-03-06 | Ishihara Sangyo Kaisha, Ltd. | Harmful organism control composition, and method for control of harmful organisms |
AP2983A (en) * | 2008-04-17 | 2014-09-30 | Ishihara Sangyo Kaisha | Harmful organism control composition, and method for control of harmful organisms |
JP2009275036A (en) * | 2008-04-17 | 2009-11-26 | Ishihara Sangyo Kaisha Ltd | Harmful organism control agent composition and method for controlling harmful organism |
KR101603806B1 (en) * | 2008-04-17 | 2016-03-16 | 이시하라 산교 가부시끼가이샤 | Harmful organism control composition, and method for control of harmful organisms |
CN102228028A (en) * | 2011-05-30 | 2011-11-02 | 青岛海利尔药业有限公司 | Pesticide composition containing sulfur-fluorine oxime ether and part of amide pesticides |
CN104837344A (en) * | 2012-12-06 | 2015-08-12 | 石原产业株式会社 | Oil-based pesticidal suspension |
CN104012539B (en) * | 2014-05-14 | 2015-09-23 | 青岛瀚生生物科技股份有限公司 | Flonicamid and four chlorantraniliprole compounded pesticides |
CN104012539A (en) * | 2014-05-14 | 2014-09-03 | 青岛瀚生生物科技股份有限公司 | Compound insecticide containing flonicamid and tetrchlorantraniliprole |
WO2017133868A1 (en) * | 2016-02-02 | 2017-08-10 | Evonik Degussa Gmbh | Powdery formulations with surface active substances on solid, water-soluble carriers, method for the production and use thereof |
EP3410851B1 (en) * | 2016-02-02 | 2020-07-22 | Evonik Operations GmbH | Powder formulations of surface active agents on solid, water-soluble carriers, method for their preparation and their use |
CN107212018A (en) * | 2017-03-02 | 2017-09-29 | 华南农业大学 | A kind of composition pesticide of suitable drip irrigation |
CN107212018B (en) * | 2017-03-02 | 2019-11-19 | 华南农业大学 | A kind of composition pesticide of suitable trickle irrigation |
Also Published As
Publication number | Publication date |
---|---|
AU2005237438A1 (en) | 2005-11-10 |
US8227493B2 (en) | 2012-07-24 |
NZ550372A (en) | 2009-12-24 |
AU2005237438B2 (en) | 2010-01-07 |
CR8688A (en) | 2007-10-12 |
CA2563261A1 (en) | 2005-11-10 |
ECSP066923A (en) | 2007-02-28 |
ZA200608450B (en) | 2008-08-27 |
CA2563261C (en) | 2013-04-09 |
BRPI0509858A (en) | 2007-10-09 |
EP1734822A1 (en) | 2006-12-27 |
MXPA06011760A (en) | 2006-12-15 |
EP1734822A4 (en) | 2010-03-31 |
US20100120870A1 (en) | 2010-05-13 |
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