GB1323045A - 2-acylaminothiazole derivatives and their use as herbicides - Google Patents

2-acylaminothiazole derivatives and their use as herbicides

Info

Publication number
GB1323045A
GB1323045A GB191371A GB191371A GB1323045A GB 1323045 A GB1323045 A GB 1323045A GB 191371 A GB191371 A GB 191371A GB 191371 A GB191371 A GB 191371A GB 1323045 A GB1323045 A GB 1323045A
Authority
GB
United Kingdom
Prior art keywords
alkyl
hydrogen
cycloalkyl
carbon atoms
methyl
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.)
Expired
Application number
GB191371A
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB1323045A publication Critical patent/GB1323045A/en
Expired legal-status Critical Current

Links

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
    • C07D277/54—Nitrogen and either oxygen or 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
    • 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

Landscapes

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

Abstract

1323045 Derivatives of 2-acylaminothiazoles SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ NV 14 Jan 1971 [16 Jan 1970 20 April 1970] 1913/71 Heading C2C Novel thiazoles of the formula in which R and R<SP>1</SP> are hydrogen or C 1-4 alkyl, R<SP>2</SP> is C 2-8 alkyl, cycloalkyl of up to 8 carbon atoms, C 2-8 alkenyl or aryl (each of which may be substituted by F, Cl, Br, -CN or -CF 3 ), or R 2 is -NR<SP>3</SP>R<SP>4</SP>, where R<SP>3</SP> is hydrogen, C 1-2 alkyl or R<SP>5</SP>CO- (where R<SP>5</SP> is C 1-3 alkyl) and R<SP>4</SP> is C 1-2 alkyl or R<SP>5</SP>CO-, n is 0, 1 or 2, and R<SP>6</SP> is hydrogen (when n is 0), C 1-4 alkyl, cycloalkyl of up to 4 carbon atoms, or -NR<SP>7</SP>R<SP>8</SP> (when n is 2) where R<SP>7</SP> is hydrogen, C 1-4 alkyl, or cycloalkyl of up to 4 carbon atoms and R<SP>8</SP> is as R<SP>7</SP> or an alkali metal ion or R<SP>5</SP>CO-, or when R<SP>7</SP> is H or alkyl R<SP>8</SP> may be C 1-3 alkoxy or -NR<SP>9</SP>R<SP>10</SP>, where R<SP>9</SP> and R<SP>10</SP> are hydrogen or C 1-3 alkyl, or R<SP>7</SP> and R<SP>8</SP> together represent an alkylene radical, are prepared by reacting an amine of the formula with an acyl halide R<SP>2</SP>COX, or to obtain the ureas in which R<SP>3</SP> is hydrogen, with an isocyanate R<SP>4</SP>NCO. The 5-thioethers, where n is 0, may be oxidized with chloroperbenzoic acid to the sulphoxides or with hydrogen peroxide to the sulphones. The 5-sulphamoyl derivatives may be obtained by chlorosulphonation of the 2-acylaminothiazoles and subsequent reaction with an amine R<SP>7</SP>R<SP>8</SP>NH. A large number of amides and ureas are specified. 2 - Amino - 5 - (ethyl- or methyl - thio)-thiazole is obtained by bromination of 2-aminothiazole and condensation of the resulting 2-amino-5- bromothiazole with ethyl or methyl mercaptan. The 4-methyl analogues are obtained similarly. The novel thiazoles possess herbicidal properties and are used in conventional forms as pre- and post-emergence weed-killers.
GB191371A 1970-01-16 1971-01-14 2-acylaminothiazole derivatives and their use as herbicides Expired GB1323045A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US351070A 1970-01-16 1970-01-16
US3036770A 1970-04-20 1970-04-20

Publications (1)

Publication Number Publication Date
GB1323045A true GB1323045A (en) 1973-07-11

Family

ID=26671852

Family Applications (1)

Application Number Title Priority Date Filing Date
GB191371A Expired GB1323045A (en) 1970-01-16 1971-01-14 2-acylaminothiazole derivatives and their use as herbicides

Country Status (6)

Country Link
CA (1) CA984848A (en)
CH (1) CH564301A5 (en)
DE (1) DE2101640A1 (en)
FR (1) FR2075560A5 (en)
GB (1) GB1323045A (en)
NL (1) NL7100497A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001047904A1 (en) * 1999-12-23 2001-07-05 Bayer Aktiengesellschaft Thiazolyl amide derivatives
KR100899491B1 (en) 2001-06-22 2009-05-26 아이쿠리스 게엠베하 운트 코. 카게 Topical Application of Thiazolyl Amides
US8784887B2 (en) 2005-03-30 2014-07-22 Aicuris Gmbh & Co. Kg Pharmaceutical preparation of N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6500817B1 (en) 1999-03-08 2002-12-31 Bayer Aktiengesellschaft Thiazolyl urea derivatives and their utilization as antiviral agents
HUE061307T2 (en) 2017-10-05 2023-06-28 Innovative Molecules Gmbh Enantiomers of substituted thiazoles as antiviral compounds

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001047904A1 (en) * 1999-12-23 2001-07-05 Bayer Aktiengesellschaft Thiazolyl amide derivatives
US7105553B2 (en) 1999-12-23 2006-09-12 Bayer Aktiengesellschaft Thiazolyl amide derivatives
KR100899491B1 (en) 2001-06-22 2009-05-26 아이쿠리스 게엠베하 운트 코. 카게 Topical Application of Thiazolyl Amides
US7883713B2 (en) 2001-06-22 2011-02-08 Aicuris Gmbh & Co. Kg Topical application of thiazolyl amides
US8784887B2 (en) 2005-03-30 2014-07-22 Aicuris Gmbh & Co. Kg Pharmaceutical preparation of N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide

Also Published As

Publication number Publication date
NL7100497A (en) 1971-07-20
FR2075560A5 (en) 1971-10-08
CH564301A5 (en) 1975-07-31
CA984848A (en) 1976-03-02
DE2101640A1 (en) 1971-07-22

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees