Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
  • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
  • C07C69/708—Ethers
• • 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

Definitions

• the present invention relates to solvents for agricultural applications (e.g., pesticides) and to pesticide formulations.
• Aromatic solvents such as xylene
• Xylene is commonly used as it provides several advantages, such as dissolving a variety of active ingredients and being easily emulsified in water on dilution.
• disadvantages to xylene’s use as a solvent such as flammability, combustibility, and toxicity.
• solvent alternatives to xylene for use in agricultural applications.
• the present invention provides solvents for pesticides that, in some embodiments, have a dissolving ability comparable to that of xylene while also being more environmentally friendly.
• the present invention provides a solvent for pesticides that comprises an ether ester of Formula 1:
• R 1 and R 2 are each independently one of an alkyl group having 1 to 4 carbon atoms or an aryl group, wherein R 3 is hydrogen, methyl, or ethyl, and wherein n is 1 to 6. In some embodiments, R 1 and R 2 are ethyl groups, R 3 is hydrogen, and n is 2.
• the present invention provides a pesticide formulation that comprises the ether ester of Formula 1 and a pesticide.
• an aqueous composition that includes particles of “a” hydrophobic polymer can be interpreted to mean that the composition includes particles of "one or more" hydrophobic polymers.
• the numerical ranges disclosed herein include all values from, and including, the lower and upper value.
• ranges containing explicit values e.g., 1 to 7
• any subrange between any two explicit values is included (e.g., 1 to 2; 2 to 6; 5 to 7; 3 to 7; 5 to 6; etc. ) .
• compositions claimed through use of the term “comprising” may include any additional additive, adjuvant, or compound, whether polymeric or otherwise, unless stated to the contrary.
• the term, “consisting essentially of” excludes from the scope of any succeeding recitation any other component, step, or procedure, excepting those that are not essential to operability.
• the term “consisting of” excludes any component, step, or procedure not specifically delineated or listed.
• solvent and like terms mean a substance that is capable of dissolving another substance (i.e., a solute) to form an essentially uniformly dispersed mixture (i.e., solution) at the molecular or ionic size level.
• a solvent for pesticides comprises an ether ester of Formula 1:
• R 1 and R 2 are each independently one of an alkyl group having 1 to 4 carbon atoms or an aryl group, wherein R 3 is hydrogen, methyl, or ethyl, and wherein n is 1 to 6. In some embodiments, R 1 and R 2 are ethyl groups, R 3 is hydrogen, and n is 2.
• a pesticide formulation comprises a pesticide and a solvent according to any of the embodiments disclosed herein.
• the solvent comprises 1 to 90 weight percent of the formulation and the pesticide comprises 10 to 99 weight percent of the formulation.
• the solvent in some embodiments, comprises 2 to 70 weight percent of the formulation, and the pesticide comprises 30 to 98 weight percent of the formulation.
• the pesticide comprises one or more of chlopyrifos, tebuconazole, difenoconazole, triazolone, quizalofop-p-ethyl, myclobutanil, pyraclostrobin, bifenthrin, buprofezin, and beta-cypermethrin.
• Solvents for pesticides comprise an ether ester of Formula 1:
• R 1 and R 2 are each independently one of an alkyl group having 1 to 4 carbon atoms or an aryl group, wherein R 3 is hydrogen, methyl, or ethyl, and wherein n is 1 to 6. In some embodiments, R 1 and R 2 are ethyl groups, R 3 is hydrogen, and n is 2.
• Solvents for pesticides consist of an ether ester of Formula 1:
• R 1 and R 2 are each independently one of an alkyl group having 1 to 4 carbon atoms or an aryl group, wherein R 3 is hydrogen, methyl, or ethyl, and wherein n is 1 to 6. In some embodiments, R 1 and R 2 are ethyl groups, R 3 is hydrogen, and n is 2.
• Solvents for pesticides consist essentially of an ether ester of Formula 1:
• R 1 and R 2 are each independently one of an alkyl group having 1 to 4 carbon atoms or an aryl group, wherein R 3 is hydrogen, methyl, or ethyl, and wherein n is 1 to 6. In some embodiments, R 1 and R 2 are ethyl groups, R 3 is hydrogen, and n is 2.
• the ether ester is ethyl-3-ethoxy propionate and are commercially available from The Dow Chemical Company as UCAR TM Ester EEP.
• Solvents for pesticides of the present invention can comprise, consist of, or consist essentially of two or more ether esters of Formula 1.
• “Two or more ether esters of Formula 1” means that the solvent comprises at least two distinct ether esters of Formula 1 (e.g., a first ether ester in which R 1 and R 2 methyl and a second ether ester in which R 1 and R 2 are ethyl; or a first ether ester in which n is 2 and a second ether ester in which n is 3 and all other substituents or components of the two ether esters are the same; etc.
• the ether esters can differ from one another in more than one substituent or component, and the solvent can comprise any number of different ether esters of Formula 1.
• solvents of the present invention comprise or consist essentially of at least 95 percent by weight of ether esters of Formula 1.
• Solvents of the present invention in other embodiments, comprise or consist essentially of at least 95 weight percent, or at least 97 weight percent, or at least 98 weight percent or at least 99 weight percent, or at least 99.9 weight percent of ether esters of Formula 1.
• solvents of the present invention comprise or consist essentially of at least 95 percent by weight ethyl-3-ethoxy propionate.
• Solvents of the present invention in other embodiments, comprise or consist essentially of at least 95 weight percent, or at least 97 weight percent, or at least 98 weight percent or at least 99 weight percent, or at least 99.9 weight percent of ethyl-3-ethoxy propionate.
• Pesticide formulations according to the present invention comprise a pesticide and a solvent according to any of the embodiments of solvents for pesticides disclosed herein.
• pesticides include, but are not limited to, chlopyrifos, tebuconazole, difenoconazole, triazolone, quizalofop-p-ethyl, myclobutanil, pyraclostrobin, bifenthrin, buprofezin, and beta-cypermethrin.
• a pesticide formulation comprises 1 to 90 weight of a solvent according to any of the solvents for pesticides disclosed herein and 10 to 99 weight percent of the pesticide, each based on the total weight of the formulation. In some embodiments, a pesticide formulation comprises 2 to 70 weight of the solvent and 30 to 98 weight percent of the pesticide, each based on the total weight of the formulation.
• a pesticide formulation consists of 1 to 90 weight of a solvent according to any of the solvents for pesticides disclosed herein and 10 to 99 weight percent of the pesticide, each based on the total weight of the formulation. In some embodiments, a pesticide formulation consists of 2 to 70 weight of the solvent and 30 to 98 weight percent of the pesticide, each based on the total weight of the formulation.
• a pesticide formulation consists essentially of 1 to 90 weight of a solvent according to any of the solvents for pesticides disclosed herein and 10 to 99 weight percent of the pesticide, each based on the total weight of the formulation. In some embodiments, a pesticide formulation consists essentially of 2 to 70 weight of the solvent and 30 to 98 weight percent of the pesticide, each based on the total weight of the formulation.
• Optional materials that are not essential to the operability of, but can be included in, the pesticide formulations of this invention include, but are not limited to, _antioxidants, colorants, water scavengers, stabilizers, and the like. These materials do not have any material impact on the efficacy of the pesticide formulation. These optional materials are used in known amounts, e.g., 0.10 to 5, or 4, or 3, or 2, or 1, weight percent based on the weight of the solvent, and they are used in known ways.
• Pesticide formulations can be prepared using techniques known to those of skill in the art. For example, the active ingredient (pesticide) can be dissolved in a solvent, and then emulsifiers or other conventional additives can be added.
• the xylene is from Sinopharm, Co., China.
• Solvesso 150 is an aromatic solvent (CAS No. 64742-94-5) from ExxonMobil Chemical Co.
• the ethyl 3-ethoxypropionate is UCAR TM Ester EEP available from The Dow Chemical Company.
• the solubility of various pesticides in these solvents are evaluated.
• the pesticides are shown in Table 2:
• Each pesticide powder is added by solvent in 2%stepwise increments to the final pesticide concentration.
• Each pesticide reaches a concentration where the pesticide powder is not dissolved by the solvent.
• the concentration just prior to the concentration where the pesticide powder is not dissolved is shown in Table 3.
• the data in Table 3 reflects a solubility that is no more than 2%lower than the actual solubility.
• Comparative Solvent A has a stronger dissolving ability than Inventive Solvent 1 for some active ingredients (e.g., chlopyrifos, quizalofop-p-ethyl and bifenthrin) . However, for the rest of evaluated active ingredients, Inventive Solvent 1 exhibits better solubility than Comparative Solvent A. Overall, Inventive Solvent 1 is believed to exhibit comparable dissolving performance relative to Comparative Solvent A with respect to the various pesticides evaluated. While exhibiting comparable dissolving performance, Inventive Solvent 1 is also advantageously believed to be more environmentally friendly than Comparative Solvent A.
• active ingredients e.g., chlopyrifos, quizalofop-p-ethyl and bifenthrin
• Comparative Solvent B In comparing the dissolving ability of Comparative Solvent B and Inventive Solvent 1, the two solvents have comparable dissolving ability as to three of the evaluated active ingredients (buprofezin, bifenthrin and quizalofop-p-ethyl) .
• active ingredients buprofezin, bifenthrin and quizalofop-p-ethyl
• Inventive Solvent 1 provides much better solubility performance than Comparative Solvent B.
• Inventive Solvent 1 has a stronger dissolving ability for these active ingredients than Comparative Solvent B.
• Inventive Solvent 1 While exhibiting generally stronger dissolving performance, Inventive Solvent 1 is also advantageously believed to be more environmentally friendly than Comparative Solvent B.

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• Life Sciences & Earth Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Health & Medical Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Plant Pathology (AREA)
• Toxicology (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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• 2017
  • 2017-11-03 EP EP17930200.5A patent/EP3704088B1/en active Active
  • 2017-11-03 CN CN201780096176.3A patent/CN111247122B/zh active Active
  • 2017-11-03 US US16/638,416 patent/US20200253196A1/en not_active Abandoned
  • 2017-11-03 WO PCT/CN2017/109246 patent/WO2019084895A1/en not_active Ceased
  • 2017-11-03 ES ES17930200T patent/ES3040472T3/es active Active
  • 2017-11-03 BR BR112020008102-7A patent/BR112020008102B1/pt active IP Right Grant
  • 2017-11-03 JP JP2020522868A patent/JP7227239B2/ja active Active

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