[go: up one dir, main page]

EP4573074A1 - Procédé de préparation et d'isolement de produits intermédiaires de certains pesticides mésoioniques - Google Patents

Procédé de préparation et d'isolement de produits intermédiaires de certains pesticides mésoioniques

Info

Publication number
EP4573074A1
EP4573074A1 EP23765126.0A EP23765126A EP4573074A1 EP 4573074 A1 EP4573074 A1 EP 4573074A1 EP 23765126 A EP23765126 A EP 23765126A EP 4573074 A1 EP4573074 A1 EP 4573074A1
Authority
EP
European Patent Office
Prior art keywords
phenyl
trifluoromethyl
solvent
moles
process according
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.)
Pending
Application number
EP23765126.0A
Other languages
German (de)
English (en)
Inventor
Michael L. Trippeer
Chunming Zhang
Honglu Zhang
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.)
Corteva Agriscience LLC
Original Assignee
Corteva Agriscience 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 Corteva Agriscience LLC filed Critical Corteva Agriscience LLC
Publication of EP4573074A1 publication Critical patent/EP4573074A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings

Definitions

  • Triflumezopyrim is a mesoionic pesticide that is used against rice plant hopper, as well as other pests. Ammonium, potassium, sodium, other metal salts, and organic amine salts of 2-[3-(trifluoromethyl)phenyl]propanedioate may be used as an intermediate in the synthesis of triflumezopyrim.
  • Triflumezopyrim has the following structure.
  • sodium 2-(3-(trifluoromethyl)phenyl)mal onate is prepared from dimethyl 2-(3- (trifluoromethyl)phenyl)malonate (hereafter also known as “DTPM”).
  • STPM is prepared, in general, by conducting a saponification reaction followed by crystallization to obtain STPM in a higher yield and higher purity than the prior art.
  • other alkyl substituents may be used such as diethyl 2-(3-(trifluoromethyl)phenyl)mal onate or dipropyl 2-(3- (trifluoromethyl)phenyl)malonate, as well as mixtures of alkyl substituents with or without DTPM
  • DTPM and sodium hydroxide are mixed under conditions to produce STPM.
  • about 2 moles to about 8 moles of NaOH per mole of DTPM preferably, about 2 moles to about 4 moles of NaOH per mole of DTPM, and more preferably, about 2 moles to about 3 moles of NaOH per mole of DTPM may be used.
  • the NaOH is preferably a solution of sodium hydroxide in water of 5 to 50 weight percent (wt %) concentration, and even more preferably, a solution of sodium hydroxide in water of 10 to 40 wt % concentration.
  • temperatures from about 0 °C to about 50 °C may be used; preferably temperatures from about 5 °C to about 25 °C may be used.
  • pressures from about 10 kilopascals (kPa) to about 1000 kPa may be used; preferably pressures from about 50 kPa to about 150 kPa may be used, however, generally, ambient pressure is preferred.
  • a resulting mixture comprising STPM is further mixed with additional solvent, preferably isopropyl alcohol, under temperatures from about 5 °C to about 20 °C, preferably from about 10 °C to about 15 °C, and pressures indicated above. These conditions promote better crystallization of STPM to obtain higher yield and higher purity of STPM.
  • the amount of additional solvent used is from about 1 mole to about 50 moles of solvent per mole of STPM, preferably, about 1 mole to about 30 moles of solvent per mole of STPM, and more preferably, about 1 mole to about 4 moles of solvent per mole of STPM may be used. It should be noted that a mixture of different solvents may be used, such as, for example, a mixture of isopropyl alcohol with water or other alcohols such as ethanol.
  • a process to produce sodium 2-(3-(trifluoromethyl)phenyl)mal onate from dimethyl 2-(3-(trifluoromethyl)phenyl)mal onate comprising: (1) mixing dimethyl 2-(3-(trifluoromethyl)phenyl)mal onate and NaOH in a solvent, wherein said solvent comprises isopropyl alcohol, and said mixing is under temperature and pressures to produce a mixture comprising sodium 2-(3-(trifluoromethyl)phenyl)malonate; and
  • 9D A process according to detail 7D wherein said pressure is about ambient pressure.
  • 10D A process according to details ID, 2D, 3D, 4D, 5D, 6D, 7D, 8D, or 9D, wherein the amount of solvent used is from about 1 mole to about 32 moles of solvent per mole of dimethyl 2-(3-(trifluoromethyl)phenyl)mal onate when mixing with NaOH.
  • a process according to detail 1 OD wherein the amount of solvent used is from about 1 mole to about 16 moles of solvent per mole of dimethyl 2-(3- (trifluoromethyl)phenyl)malonate when mixing with NaOH.
  • a process according to detail 10D wherein the amount of solvent to used is from about 1 mole to about 4 moles of solvent per mole of dimethyl 2-(3- (trifluoromethyl)phenyl)malonate when mixing with NaOH.
  • STPM sodium 2-(3-(trifluoromethyl)phenyl)malonate
  • DTPM dimethyl 2-(3-(trifluoromethyl)phenyl)malonate
  • Example One The procedure as in Example One was conducted four other times except that instead of using propan-2-ol, a different solvent selected from methanol, ethanol, 1 -propanol, and n- butanol, was used.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de production de 2-(3-(trifluorométhyl)phényl)malonate de sodium à partir de 2-(3-(trifluorométhyl)phényl)malonate de diméthyle.
EP23765126.0A 2022-08-18 2023-08-16 Procédé de préparation et d'isolement de produits intermédiaires de certains pesticides mésoioniques Pending EP4573074A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202263371760P 2022-08-18 2022-08-18
PCT/US2023/072301 WO2024040111A1 (fr) 2022-08-18 2023-08-16 Procédé de préparation et d'isolement de produits intermédiaires de certains pesticides mésoioniques

Publications (1)

Publication Number Publication Date
EP4573074A1 true EP4573074A1 (fr) 2025-06-25

Family

ID=87930306

Family Applications (1)

Application Number Title Priority Date Filing Date
EP23765126.0A Pending EP4573074A1 (fr) 2022-08-18 2023-08-16 Procédé de préparation et d'isolement de produits intermédiaires de certains pesticides mésoioniques

Country Status (5)

Country Link
EP (1) EP4573074A1 (fr)
JP (1) JP2025526908A (fr)
KR (1) KR20250051696A (fr)
CN (1) CN119698404A (fr)
WO (1) WO2024040111A1 (fr)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI401023B (zh) 2008-02-06 2013-07-11 Du Pont 中離子農藥
UA110924C2 (uk) 2009-08-05 2016-03-10 Е. І. Дю Пон Де Немур Енд Компані Мезоіонні пестициди
CN102574815A (zh) 2009-08-05 2012-07-11 杜邦公司 介离子杀虫剂
KR20120050467A (ko) 2009-08-05 2012-05-18 이 아이 듀폰 디 네모아 앤드 캄파니 메소이온성 살충제
TWI528899B (zh) 2010-12-29 2016-04-11 杜邦股份有限公司 中離子性殺蟲劑
TWI572587B (zh) 2011-12-15 2017-03-01 杜邦股份有限公司 丙二酸二鹽及用以製備丙二醯基二鹵化物之方法
TW201738229A (zh) 2016-04-26 2017-11-01 杜邦股份有限公司 製備ｎ－［（５－嘧啶基）甲基］－２－吡啶胺之方法
CN111683530A (zh) 2018-03-05 2020-09-18 纳幕尔杜邦公司 用于制备某些介离子类杀虫剂的方法和中间体

Also Published As

Publication number Publication date
CN119698404A (zh) 2025-03-25
KR20250051696A (ko) 2025-04-17
WO2024040111A1 (fr) 2024-02-22
JP2025526908A (ja) 2025-08-15

Similar Documents

Publication Publication Date Title
KR960000758B1 (ko) 광학적 활성 히드록시벤질아민 유도체 및 그의 제조방법
EP4573074A1 (fr) Procédé de préparation et d'isolement de produits intermédiaires de certains pesticides mésoioniques
JPS60136573A (ja) １，２，４−トリアゾロン誘導体の製造方法
JPS6261587B2 (fr)
US4187225A (en) Novel synthesis of bis pyrazolone oxonol dyes
SK45395A3 (en) Method of production of dimethylaminborane
JP3790880B2 (ja) 新規な２，４，６−トリメルカプト−１，３，５−トリアジンのトリリチウム塩又はトリカリウム塩の水和物並びに水和物及び無水物の製造法
US4197410A (en) N-[(N-Nitrosoalkylamino)methyl]carbamic acid esters for generating diazoalkanes
JP2010018595A (ja) Ｎ，ｎ’−ジアルキルヒドラジン化合物の製造方法およびピラゾリジンジオン化合物
US5475140A (en) Process for producing N,N-disubstituted p-phenylenediamine derivative sulfate
JP3044383B2 (ja) 含窒素６員環化合物の製造方法
JP3042123B2 (ja) Ｎ−シアノアセトアミジン誘導体の製法
JP4340914B2 (ja) 新規な２，４，６−トリメルカプト−１，３，５−トリアジンのトリリチウム塩又はトリカリウム塩の水和物並びに水和物及び無水物の製造法
WO2024021190A1 (fr) Procédé de préparation d'un composé à base de phosphine et son utilisation
JP3165871B2 (ja) ジアルキル（ｎ−シアノイミド）カーボネートの製造方法
SU595312A1 (ru) Способ получени 2,4,6-замещенных перхлоратов пиримидини
JPH107645A (ja) アルキルニトログアニジン誘導体の製造方法
JPS61140554A (ja) アルキルｎ‐マレイルフエニルアラネートの用途およびその製造方法
JP2021181407A (ja) アミドアルコール化合物の水和物及びその製造方法、並びに、及びラクトン化合物の製造方法
JPS5857354A (ja) ２−アジド−３−ベンジルオキシ−プロピオン酸−ベンジルエステル及びその製法
JPS63275568A (ja) Ｎ−メチロ−ルヒダントイン類の製造法
JPH10316605A (ja) ３−置換−１−プロパノールの製造方法
WO1995021828A1 (fr) Procede de production de derives de l'hexahydropyridazine et de l'hexahydropyridazine-1,2-dicarboxylate
JPS58154537A (ja) オキシ安息香酸低級アルアルキルエステルの製造法
WO1997030972A1 (fr) Procede de preparation de ng-monomethyl-l-hydrochlorure d'arginine

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

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

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

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

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

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20250224

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC ME MK MT NL NO PL PT RO RS SE SI SK SM TR

DAV Request for validation of the european patent (deleted)