EP1052902A1 - Compositions permettant de conserver du methomyle sous forme de solution - Google Patents

Compositions permettant de conserver du methomyle sous forme de solution

Info

Publication number
EP1052902A1
EP1052902A1 EP99905747A EP99905747A EP1052902A1 EP 1052902 A1 EP1052902 A1 EP 1052902A1 EP 99905747 A EP99905747 A EP 99905747A EP 99905747 A EP99905747 A EP 99905747A EP 1052902 A1 EP1052902 A1 EP 1052902A1
Authority
EP
European Patent Office
Prior art keywords
composition
methomyl
glycol
carbonate
group
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP99905747A
Other languages
German (de)
English (en)
Inventor
Edward Thomas Marquis
Howard Meyer Stridde
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Huntsman Specialty Chemicals Corp
Huntsman Petrochemical LLC
Original Assignee
Huntsman Specialty Chemicals Corp
Huntsman Petrochemical LLC
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
Application filed by Huntsman Specialty Chemicals Corp, Huntsman Petrochemical LLC filed Critical Huntsman Specialty Chemicals Corp
Publication of EP1052902A1 publication Critical patent/EP1052902A1/fr
Withdrawn legal-status Critical Current

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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Definitions

  • This invention relates to the preparation and use of solutions containing dissolved insecticidal compounds for which the solubility of the insecticide in the solution is a limiting factor of the concentration at which stable solutions may be stored. More particularly, it relates to the transportation, storage, and use of solutions containing methomyl, using an alkylene carbonate in combination with at least one other oxygen- bearing organic molecule as components of liquid-phase solutions that contain dissolved methomyl.
  • Methomyl is the methyl ester of N-[(methylcarbamoyl)oxy]thioacetimidic acid. This compound has found widespread use as an insecticide since the early 1970's. Although being a very effective insecticide of relatively low toxicity, the tendency of the material to crystallize out of its solutions at low temperatures is widely known to be a nuisance to personnel involved in the storage, transportation, and use of its solutions. Since it is convenient to provide agriculturally-active compounds dissolved in suitable solvent for later dilution in the field, the tendency of a given material to crystallize out of a concentrated solution is a limiting factor of the effective concentration at which solutions of the material may be prepared for commercial transport and sale.
  • methomyl inflated amounts of solution relative to other water-emulsifyable formulations have been found necessary when proceeding according to prior art methods for preparing solutions of methomyl. This has meant that proportionately-inflated amounts of solvent or other inert ingredients must be dispersed along with the active methomyl in a given insecticidal application. 2
  • compositions disclosed herein provide methomyl solutions of higher concentrations over prior art, possessive of a decreased tendency for dissolved methomyl to crystallize out when the solution is subjected to temperatures near zero degrees centigrade for prolonged periods of time.
  • This invention provides a single-phase, liquid methomyl concentrate composition comprising methomyl and certain organic solvents that can be diluted with water for spray tank use by an end user.
  • a solvent combination according to the invention useful for dissolving methomyl and maintaining it at high concentrations in solution over a wide temperature range comprises a first component that contains at least one alkylene carbonate, and a second component (or co-solvent) that includes least one organic oxygen compound.
  • the alkylene carbonate component may be selected from propylene and butylene carbonate
  • the organic oxygen compound may be selected from classes of compounds that may include alcohols, glycols, ketones, ethers, lactones and heterocyclic compounds in which a member of the ring structure contains a keto function, such as N- methyl pyrrolidone.
  • the combination of alkylene carbonate, methomyl, and other component(s) may contain a high concentration of methomyl, preferably 20 % by weight or more with respect to the total weight of the finished solution, is not chemically 3 reactive under conditions normally encountered in storage of methomyl solutions, is easily and quickly dilutable with water to the desired spray concentration, and the applied spray does not injure the crops targeted. Additionally, the solution retains a high degree of insecticidal qualities, does not have a tendency to separate into separate liquid layers in storage, and the ingredients possess low hazard potential during and after spray applications as defined by existing local and national environmental regulations.
  • the present invention is directed at solutions comprising methomyl dissolved in a solution combination that comprises a first component containing at least one alkylene carbonate and a second component that includes an organic oxygen compound.
  • a co-solvent organic oxygen compound
  • an alkylene carbonate for example propylene carbonate
  • the co-solvent may be selected from various glycols and ethers thereof; ketones; alcohols; lactones; and alkylene carbonates.
  • a suitable solvent combination To produce a suitable solvent combination according to the invention, one mixes the components of the solvent combination under ambient or slightly elevated temperature, and agitates to produce a homogeneous solution. This typically requires between about 5 minutes and l hour of agitation, depending upon the type of vessel in which the mixing is conducted and the agitation employed. (When using laboratory-scale equipment such as a 250 ml beaker and a glass stirring rod, suitable combination is produced within one minute when vigorous stirring with a glass stirring rod is employed).
  • a solution of methomyl in accordance with this invention one preferably adds the desired amount of methomyl to the solvent combination once the solvent combination 4 has been made homogeneous, and agitates the solvent until solution is effected. This may be done with or without the assistance of added heat energy, but preferably the solution is heated to about 45 degrees Centigrade prior to the methomyl addition, to facilitate the rapid dissolution thereof.
  • compositions of several formulations useful for keeping methomyl in solution at high concentration over a wide range of temperatures have been discovered, the formulations of which are set forth in examples 1 - 12 below.
  • synergistic properties of the solvent combinations are believed responsible for their unexpected ability to maintain methomyl in solution in which no crystallization is evident even after prolonged storage at 0 degrees C.
  • the unexpectedness of the success in examples 1 - 12 is evidenced by the compositions of the samples in tables III and IV in which methomyl crystallization was evident after prolonged storage of the solutions at the same low temperatures.
  • Table II Successful solution compositions for systems retaining 28.0 and 30 % methomyl dissolved at 0 degrees C with no crystallization evident after one month.
  • the most preferred composition is that set forth in example 1. This is most preferred because of the low toxicity of the DPNB, its high flash point, its odorless character, and its relatively low cost.
  • compositions for which methomyl crystallization was evident after 30 days aging at 0 degrees C are set forth in tables III and IV below:
  • Table TV More examples of systems that displayed methomyl crystallizing out when stored at 0 degrees C for 30 days
  • These solutions are suitable for use (after appropriate dilution) in the control of pestiferous insects belonging to such orders as Lepidoptera, Homoptera, Hemiptera, Diptera, and Coleoptera, including but not limited to cotton bollworm, tobacco budworm, southern armyworm, soybean looper, beet armyworm, cotton aphid, tarnished plant bug, and white flies.
  • the insects are controlled by applying the solutions to the area to be protected, or to the pests themselves. In the case of agricultural applications, a dispersion or emulsion of the solvents are applied to the foliage to be protected.
  • Effective amounts depend upon the species to be controlled, its life stage, its size and location, the amount of rainfall, time of year, moisture, temperature. type of application and other variables, all of which are known or readily determinable by those of ordinary skill in the art. Generally, dosage levels of between about 0.0625 to 4 kilograms per hectare of methomyl are required, with levels between about 0.125 to 2.0 kilograms per hectare being sufficient in most instances.
  • the solutions of this invention may be combined with surfactants, wetting agents, dispersing agents, antifoam agents and the like, as such admixtures are typical in the agricultural field and are well-known to methomyl users having ordinary skill.
  • the formulations herein set forth may be mixed with fungicides, bacteriocides, acaricides, nematicides, or other biologically active compounds.
  • Suitable surfactants are known to those skilled in the art, and include without limitation sodium lauryl sulfate and its functional anionic, non-ionic and cationic equivalents, as such are well-known to artisans of ordinary skill.
  • concentration of methomyl relates to the amount of methomyl that is dissloved in either a neat or a mixed liquid solvent combination.
  • Methomyl is known to be soluble in various organic solvents to varying degrees; however, most solvents in which it has appreciable solubility are not approved for spray use on crops or foliage. Of those solvents that are acceptable for 9 spray use, the solubility of methomyl therein is not as high as is desired, and is typically on the order of only about 20 % by weight.
  • the term "high concentrations of methomyl” means a concentration of methomyl in solution of at least 20 % by weight based upon the total weight of the solution. According to this invention, stable solutions having methomyl concentrations as high as 30 % may be prepared, which permits one-and-a-half times as much active chemical to be transported per given volume over prior art solutions containing only 20% methomyl.
  • organic oxygen compound means a chemical compound whose molecular structure includes carbon atoms and oxygen atoms, including compounds belonging to the classes: alcohols, ethers, glycols, polyalkylene glycols, ethers of glycols, ethers of polyalkylene glycols, ketones, pyrrolidones, and lactones, including substituted analogs or derivatives of compounds within these classes, whether the substituents are straight chain, branched, aromatic, or aliphatic.
  • a typical means by which the instant invention may be employed in the destruction of unwanted pests is by diluting a composition of any one of examples 1 through 12 with a desired amount of water, either alone or with additional diluents, which may include but are not limited to dyes, oils, fungicides, bacteriocides, acaricides, nematicides, or fungicides, to produce an emulsion of desired methomyl concentration.
  • the emulsion is sprayed through a conventional atomizer, including as an example 10 illustrative and not delimitive hereof, a DeVilbiss No. 152 atomizing nozzle available from the DeVilbiss Company, Somerset, Pennsylvania 15501 using atomizing air at 12 p.s.i. onto a cotton, corn, tomato, or other food-bearing plant.
  • Non-food-bearing plants, such as tobacco may also be the target.

Landscapes

  • 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

L'invention concerne des compositions liquides de substances contenant l'insecticide méthomyle sous une forme concentrée pouvant être diluée sans difficultés afin d'être pulvérisée, ou appliquée d'une autre façon, sur des récoltes ou des feuillages. Ces compositions contiennent le méthomyle en concentrations plus importantes que celles de l'état actuel de la technique et le méthomyle ne se cristallise pas dans des solutions soumises à des températures de zéro degrés centigrades. L'invention permet de transporter des quantités plus élevées de méthomyle pour un volume donné de solution et de limiter la quantité de composés inertes appliqués aux récoltes, ce qui permet d'obtenir des avantages supplémentaires du point de vue de l'environnement et des coûts.
EP99905747A 1998-02-06 1999-02-04 Compositions permettant de conserver du methomyle sous forme de solution Withdrawn EP1052902A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US7398898P 1998-02-06 1998-02-06
US24339499A 1999-02-01 1999-02-01
US243394 1999-02-01
PCT/US1999/002437 WO1999039581A1 (fr) 1998-02-06 1999-02-04 Compositions permettant de conserver du methomyle sous forme de solution
US73988P 2008-06-19

Publications (1)

Publication Number Publication Date
EP1052902A1 true EP1052902A1 (fr) 2000-11-22

Family

ID=26755131

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99905747A Withdrawn EP1052902A1 (fr) 1998-02-06 1999-02-04 Compositions permettant de conserver du methomyle sous forme de solution

Country Status (3)

Country Link
EP (1) EP1052902A1 (fr)
CA (1) CA2317127A1 (fr)
WO (1) WO1999039581A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107613767A (zh) * 2015-04-09 2018-01-19 Isp投资有限公司 协同防腐组合物

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1230293A1 (fr) * 1999-09-23 2002-08-14 The Dow Chemical Company Composition de solvant
DE19948589A1 (de) * 1999-10-08 2001-04-12 Bayer Ag Neue Flüssigformulierungen
US6503891B1 (en) * 2000-08-31 2003-01-07 Huntsman Petrochemical Corporation Water emulsifiable formulations
EP1411922A1 (fr) 2001-07-31 2004-04-28 Pfizer Products Inc. Compositions pharmaceutiques, necessaires et methodes faisant intervenir des combinaisons d'agonistes/antagonistes des oestrogenes, d'oestrogenes et de progestines
DE102005008949A1 (de) * 2005-02-26 2006-09-14 Bayer Cropscience Ag Agrochemische Formulierung zur Verbesserung der Wirkung und Pflanzenverträglichkeit von Pflanzenschutzwirkstoffen
GB2566700B (en) * 2017-09-20 2022-05-25 Rotam Agrochem Int Co Ltd Pesticidal composition comprising an oxime carbamate and the use thereof
GB2566696B (en) 2017-09-20 2020-09-16 Rotam Agrochem Int Co Ltd Pesticidal composition comprising an oxime carbamate and the use thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU568717B2 (en) * 1984-01-19 1988-01-07 Shell Chemical (Australia) Proprietary Limited Pesticide composition comprising a ketone, lower alkanol and dipolar aprotic solvent system
DE3574330D1 (en) * 1985-01-29 1989-12-28 Hoffmann La Roche Herbicidal mixture

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9939581A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107613767A (zh) * 2015-04-09 2018-01-19 Isp投资有限公司 协同防腐组合物

Also Published As

Publication number Publication date
CA2317127A1 (fr) 1999-08-12
WO1999039581A1 (fr) 1999-08-12

Similar Documents

Publication Publication Date Title
US9192159B2 (en) Azoxystrobin formulations
US3894149A (en) Pesticidal Concentrates
AU5086598A (en) Microemulsion and method
NZ210326A (en) Pyrethroid-based pesticide composition
JPS63236532A (ja) 水中油型エマルシヨン、その製造方法および使用方法
WO1999039581A1 (fr) Compositions permettant de conserver du methomyle sous forme de solution
EP0533057B1 (fr) Agent herbicide sélectif sous forme de micro-émulsions concentrées
US6187715B1 (en) Water-based microemulsions of a lower alkyl ester of quinoxalinyl herbicide
EP0645964B1 (fr) Composition herbicide
US5234919A (en) Water soluble, highly active dimethoate formulations in an alcohol/ester solvent system
HU204393B (en) Insecticide aqouos solutions containing piretroides as active components and microemulsion compositions containing former solutions
US6541516B1 (en) Water miscible emulsions of pyrethroid insecticides or triazole fungicides
US5326789A (en) Water-based microemulsions of a triazole fungicide
JP3424304B2 (ja) 液状農薬組成物
JP2959995B2 (ja) 殺虫液剤
FR2883702A1 (fr) Concentre emulsifiable contenant du 2&#39;,4&#39;-difluoro-2-(alpha, alpha-trifluoro-m-tolyloxy)-nicotinanilide et composition aqueuse obtenue par dilution du concentre
JP3660440B2 (ja) 安定な殺虫乳剤
JPH0733605A (ja) 改良された農薬乳剤組成物
US4285968A (en) Pesticidal concentrate with stabilizing agent
JPH0789802A (ja) セミスルホコハク酸誘導体を含む水溶性植物保護組成物
AU2002312741B2 (en) Insecticidal composition having improved storage stability
EP0497806A1 (fr) Herbicides selectifs
JP2501241B2 (ja) 農園芸用殺虫殺ダニ剤
EP0226285A1 (fr) Compositions pesticides
WO2011157101A1 (fr) Composition pesticide

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20000803

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): DE FR GB

17Q First examination report despatched

Effective date: 20020627

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Withdrawal date: 20021111