WO1991017152A1 - Preparation de derives d'acide propenoique - Google Patents

Preparation de derives d'acide propenoique Download PDF

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Publication number
WO1991017152A1
WO1991017152A1 PCT/GB1991/000695 GB9100695W WO9117152A1 WO 1991017152 A1 WO1991017152 A1 WO 1991017152A1 GB 9100695 W GB9100695 W GB 9100695W WO 9117152 A1 WO9117152 A1 WO 9117152A1
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WO
WIPO (PCT)
Prior art keywords
formula
compound
optionally substituted
compounds
methyl
Prior art date
Application number
PCT/GB1991/000695
Other languages
English (en)
Inventor
Richard Winston Gordon Foster
Original Assignee
Schering Agrochemicals 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
Application filed by Schering Agrochemicals Limited filed Critical Schering Agrochemicals Limited
Publication of WO1991017152A1 publication Critical patent/WO1991017152A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/36—Sulfur atoms
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/70—Sulfur atoms
    • C07D277/74—Sulfur atoms substituted by carbon atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

  • This invention relates to a new process for the preparation of certain propenoic acid derivatives.
  • R 1 is alkyl
  • R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted heterocyclyl(thio)carbonyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted N-substituted iminomethyl or substituted heterocyclylidenemethyl which comprises
  • R 2 is alkyl
  • the protecting group is preferably an acyl and especially an acetyl group.
  • steps B) and C) can be carried out under similar conditions to those described in our EP 299 694.
  • Removal of the protecting group can be carried out in conventional manner, usually under basic conditions, eg in the presence of an alkali metal base, especially an alkoxide, in which case the compound of formula I is usually obtained as a salt.
  • Alkylation of the compound of formula I can be carried out in known manner, eg using an alkyl halide or sulphate, preferably under basic conditions, eg in the presence of a metal (especially sodium) hydride.
  • Alkyl groups are preferably of 1 to 20, eg 1 to 4, carbon atoms, especially methyl or ethyl.
  • Alkenyl and alkynyl groups are generally of three to six carbon atoms. Substituents, when present on any alkyl, alkenyl or alkynyl group, include halogen, alkoxy (e.g. of 1 to 4 carbon atoms) , haloalkoxy (e.g. difluoromethoxy) hydroxy, alkylthio, nitro, optionally substituted amino, carboxy, alkoxycarbonyl, cyano, acyloxy and aryl.
  • Aryl groups are usually phenyl, optionally substituted, e.g. by halogen, optionally substituted alkyl or alkoxy, aryl, aryloxy, nitro, amino, COOH, COOR 2 , CN, CONR 2 R 2 or S(0) n R 2 .
  • heteroaryl and heterocyclyl include groups such as thienyl, furyl, pyridyl, pyrimidinyl, pyrazolyl, thiazolyl, thiazolinyl, oxazolyl, benzimidazolyl, tetrazolyl, benzoxazolyl, thiadiazolyl, dioxolanyl, imidazopyridinyl, 1,3-benzoxazinyl, 1,3-benzothiazinyl, oxazolopyridinyl, triazolyl, triazinyl, imidazolyl, orpholino, benzofuranyl, pyrazolinyl, quinolinyl, quinazolinyl, dihydroquinazolinyl or benzothiazolyl, which themselves may be substituted, e.g.
  • acyl includes the residue of sulphonic and phosphorus containing acids as well as carboxylic acids.
  • Acyl groups are preferably alkanoyl e.g. of 1 to 4 carbon atoms.
  • Amino groups may be substituted, e.g. by one or two alkyl groups or two substituents can form a ring, e.g. to form a morpholino or piperidino ring.
  • Iminomethyl groups can be substituted both on the nitrogen and carbon. Examples of substituents on the nitrogen include aryl and alkyl. Examples of substituents on the carbon include aryl, alkyl, alkylthio, alkoxy and cyano.
  • the product is generally heated under acidic conditions to convert any Z-isomer into E-isomer.
  • R 1 and R 2 are both preferably methyl.
  • Example 1 The invention is illustrated in the following Examples. Structures of isolated novel compounds were confirmed by elemental and/or other appropriate analyses. Temperatures are in °C. Example 1
  • Compounds are assessed for activity against one or more of the following:
  • Plasmopara viticola vine downy mildew (PV) Pyricularia oryzae: rice blast (PO) Venturia inaequalis: apple scab (VI) Septoria nodorum: glume blotch (SN)
  • Aqueous solutions or dispersions of the compounds at the desired concentration, including a wetting agent, were applied by spray or by drenching the stem base of the test plants. These plants were then inoculated with appropriate test pathogens and kept under controlled environment conditions suitable for maintaining plant growth and development of the disease. After an appropriate time, the degree of infection of the leaf surface was visually estimated. Compounds were considered active if they gave greater than 50% control of the disease at a concentration of 500 ppm (w/v) or less. Compounds la, lb, and 3b were active against PV; compounds lb and 3b were active against PO; compounds lb, 3a, 3b and 3c were active against VI and compound 2 was active against SN.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cette invention décrit des composés représentés par la formule (I) et des sels de ces composés, où m représente 0 à 18, R1 représente un alkyle et R représente un aryle, un hétéroaryle, un hétérocyclyle, un hétérocyclyl(thio)carbonyle, un alcényle, un alkynyle, un iminoéthylène N-substitué, ou un hétérocyclylidèneméthyle, tous facultativement substitués. Ces composés sont obtenus (A) en attachant un groupe protecteur, W, au groupe hydroxyle d'un composé ayant la formule (II) pour produire un composé ayant la formule (III), (B) en remplaçant un hydrogène sur le méthyle du composé de la formule (III) par un groupe à substituer, Z, pour produire un composé de formule (IV), (C) en traitant le composé de formule (IV) avec un composé de formule (V): R-(CH¿2?)m-SH pour produire un composé de formule (VI) et (D) en enlevant le groupe protecteur. Les composés de formule (I) sont nouveaux et font preuve d'une activité fongicide. Ils sont aussi des intermédiaires pour la préparation d'autres composés fongicides utiles. Plusieurs des composés de formule (VI) sont aussi fongicides.
PCT/GB1991/000695 1990-05-02 1991-05-01 Preparation de derives d'acide propenoique WO1991017152A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9009916.9 1990-05-02
GB909009916A GB9009916D0 (en) 1990-05-02 1990-05-02 Preparation of acrylic acid derivatives

Publications (1)

Publication Number Publication Date
WO1991017152A1 true WO1991017152A1 (fr) 1991-11-14

Family

ID=10675386

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1991/000695 WO1991017152A1 (fr) 1990-05-02 1991-05-01 Preparation de derives d'acide propenoique

Country Status (3)

Country Link
EP (1) EP0527182A1 (fr)
GB (1) GB9009916D0 (fr)
WO (1) WO1991017152A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0656351A1 (fr) * 1993-12-03 1995-06-07 Sumitomo Chemical Company, Limited Dérivés de dithiocarbonimide comme fongicides, insecticides et acaricides
US5510344A (en) * 1989-01-11 1996-04-23 Schering Agrochemicals Limited Acrylate fungicides
KR100392075B1 (ko) * 2000-09-25 2003-07-22 한국화학연구원 살균효과를 가지는 옥사졸 유도체
KR100392074B1 (ko) * 2000-09-25 2003-08-19 한국화학연구원 살균효과를 가지는 싸이아졸 유도체

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0256667A2 (fr) * 1986-08-06 1988-02-24 Imperial Chemical Industries Plc Dérivés d'acides phényl-2-propénoiques substitués utiles en agriculture
EP0299694A2 (fr) * 1987-07-11 1989-01-18 AgrEvo UK Limited Acrylates fongicides
EP0379098A1 (fr) * 1989-01-20 1990-07-25 BASF Aktiengesellschaft Esters acryliques contenant du soufre, et fongicides les contenant
WO1991007385A1 (fr) * 1989-11-18 1991-05-30 Schering Agrochemicals Limited Preparation de derives d'acide propenoique

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0256667A2 (fr) * 1986-08-06 1988-02-24 Imperial Chemical Industries Plc Dérivés d'acides phényl-2-propénoiques substitués utiles en agriculture
EP0299694A2 (fr) * 1987-07-11 1989-01-18 AgrEvo UK Limited Acrylates fongicides
EP0379098A1 (fr) * 1989-01-20 1990-07-25 BASF Aktiengesellschaft Esters acryliques contenant du soufre, et fongicides les contenant
WO1991007385A1 (fr) * 1989-11-18 1991-05-30 Schering Agrochemicals Limited Preparation de derives d'acide propenoique

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5510344A (en) * 1989-01-11 1996-04-23 Schering Agrochemicals Limited Acrylate fungicides
EP0656351A1 (fr) * 1993-12-03 1995-06-07 Sumitomo Chemical Company, Limited Dérivés de dithiocarbonimide comme fongicides, insecticides et acaricides
US5563159A (en) * 1993-12-03 1996-10-08 Sumitomo Chemical Company, Limited Dithiocarbonimide derivatives useful as acaricidal, fungicidal, and insecticidal agents
KR100392075B1 (ko) * 2000-09-25 2003-07-22 한국화학연구원 살균효과를 가지는 옥사졸 유도체
KR100392074B1 (ko) * 2000-09-25 2003-08-19 한국화학연구원 살균효과를 가지는 싸이아졸 유도체

Also Published As

Publication number Publication date
GB9009916D0 (en) 1990-06-27
EP0527182A1 (fr) 1993-02-17

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