GB1266172A - - Google Patents

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Publication number
GB1266172A
GB1266172A GB1266172DA GB1266172A GB 1266172 A GB1266172 A GB 1266172A GB 1266172D A GB1266172D A GB 1266172DA GB 1266172 A GB1266172 A GB 1266172A
Authority
GB
United Kingdom
Prior art keywords
compound
reaction
group
hydrogen
acyclic hydrocarbon
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
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 filed Critical
Publication of GB1266172A publication Critical patent/GB1266172A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen 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
    • A01N43/82—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 three ring hetero 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
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1,266,172. 1 ,3,4-Thiadiazoles. AIR PRODUCTS & CHEMICALS Inc. 11 March, 1969 [13 March, 1968; 25 Sept., 1968], No.12704/69. Heading C2C. Compounds of formula wherein R 1 is a C 1-7 acyclic hydrocarbon or halohydrocarbon radical, the halogen being fluorine, chlorine or bromine, R 2 is hydrogen, a C 1-4 acyclic hydrocarbon radical or a phenyl group optionally substituted by chlorine, bromine or a nitro, trifluoromethyl, C 1-4 alkyl, C 1-4 alkoxy or -N(R 5 ) 2 group, in which each group R 5 is a C 1-4 alkyl group, R<SP>11</SP> is hydrogen or a group -CONR 3 R 4 , wherein R 3 is hydrogen or a C 1-4 acyclic hydrocarbon radical and R 4 is a C 1-4 acyclic hydrocarbon radical, and R 6 is a methyl or ethyl group, with the proviso that at least one of R<SP>11</SP> and R 2 is other than hydrogen, and tautomers thereof having a double bond from the ring carbon atom to the attached exocyclic nitrogen atom, are prepared by formation of the amines and imines of the invention by reaction of (a) a compound R 1 COOH with a compound NH 2 NHCSNHR 2 in the presence of polyphosphoric acid, (b) reaction of a compound (R 1 CO) 2 0 with a compound NH 2 NHCSNHR 2 to give a compound B 1 CONHNHCSNHB 2 , and treating this with concentrated sulphonic acid, or (c) reaction of a compound R 1 COCI with a compound HN 2 NHCSNHR 2 and phosphorus trichloride, followed, if desired, by conversion to a urea by (d) reaction with butyl lithium or sodium hydride and a compound ClCONR 3 R 4 or (e) reaction with an isocyanate R 3 NCO. When an isocyanate is used, a 3-CONHR 6 compound may be obtained, and this may be converted to the urea isomer by heating or by dissolving it in an organic solvent. The products have herbicidal, insecticidal, acaricidal and fungicidal activity.
GB1266172D 1968-03-13 1969-03-11 Expired GB1266172A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US71258568A 1968-03-13 1968-03-13
US76260468A 1968-09-25 1968-09-25

Publications (1)

Publication Number Publication Date
GB1266172A true GB1266172A (en) 1972-03-08

Family

ID=27108852

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1266172D Expired GB1266172A (en) 1968-03-13 1969-03-11

Country Status (6)

Country Link
JP (1) JPS5512404B1 (en)
BE (1) BE744812A (en)
DE (1) DE1912543C2 (en)
FR (1) FR2003832A1 (en)
GB (1) GB1266172A (en)
IL (2) IL31792A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2650362A1 (en) * 1975-11-07 1977-05-26 Lilly Industries Ltd HERBICIDAL AGENTS AND METHOD FOR ITS MANUFACTURING
DE2741394A1 (en) * 1977-08-29 1979-03-22 Lilly Co Eli Synergistic herbicidal compsns. - comprise inert carrier, aromatic amine and substd. nitrogen-sulphur heterocycle
US4271166A (en) * 1977-08-15 1981-06-02 Eli Lilly And Company N-(1,3,4-Thiadiazol-2-yl)benzamides
US4290798A (en) * 1972-08-14 1981-09-22 Air Products And Chemicals, Inc. Herbicidal compound and method of use
US4338449A (en) 1981-06-15 1982-07-06 Eli Lilly And Company Herbicidal thiadiazolines
US4346225A (en) 1981-06-15 1982-08-24 Eli Lilly And Company Herbicidal 2-methylamino thiadiazolines
EP2052609A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
DE102008037621A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1290223A (en) * 1969-04-21 1972-09-20
CA931961A (en) * 1970-04-17 1973-08-14 Gulf Research And Development Company Combating unwanted vegetation with 1,3,4-thiadiazolylureas
DE2059328C2 (en) * 1970-11-24 1984-02-23 Schering AG, 1000 Berlin und 4709 Bergkamen 1,1,3-Trimethyl-3- (5-ethylsulfinyl-1,3,4-thiadiazol-2-YL) urea
DE2330453A1 (en) * 1973-06-15 1975-01-09 Velsicol Chemical Corp Thidiazolyl ureidoacetaldehyde acetals - as herbicies
DE3612830A1 (en) * 1986-04-16 1987-10-22 Basf Ag THIADIAZOLYL URINE CONTAINING AGENT FOR DEBELING PLANTS

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB598072A (en) * 1944-03-20 1948-02-10 American Chem Paint Co Improvements in methods and compositions for killing weeds
US2655445A (en) * 1949-12-06 1953-10-13 Du Pont 3-(halophenyl)-1-methyl-1-(methyl or ethyl) ureas and herbicidal compositions and methods employing same
DE964548C (en) * 1955-06-03 1957-05-23 Bayer Ag Herbicides
DE1028986B (en) * 1956-01-17 1958-04-30 Hoechst Ag Process for the production of new urea derivatives
NL128117C (en) * 1959-08-21
CH403391A (en) * 1960-11-22 1965-11-30 Ciba Geigy Herbicidal agent containing new ureas
CH398543A (en) * 1961-05-06 1966-03-15 Ciba Geigy Process for the production of urea derivatives
BE632848A (en) * 1962-05-28
OA01933A (en) * 1965-04-06 1970-02-04 Pechiney Saint Gobain Thiazole derivatives.
DE1542789C3 (en) * 1965-09-18 1978-05-18 Bayer Ag, 5090 Leverkusen Selective weed control
CA931961A (en) * 1970-04-17 1973-08-14 Gulf Research And Development Company Combating unwanted vegetation with 1,3,4-thiadiazolylureas

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4290798A (en) * 1972-08-14 1981-09-22 Air Products And Chemicals, Inc. Herbicidal compound and method of use
DE2650362A1 (en) * 1975-11-07 1977-05-26 Lilly Industries Ltd HERBICIDAL AGENTS AND METHOD FOR ITS MANUFACTURING
US4271166A (en) * 1977-08-15 1981-06-02 Eli Lilly And Company N-(1,3,4-Thiadiazol-2-yl)benzamides
DE2741394A1 (en) * 1977-08-29 1979-03-22 Lilly Co Eli Synergistic herbicidal compsns. - comprise inert carrier, aromatic amine and substd. nitrogen-sulphur heterocycle
US4338449A (en) 1981-06-15 1982-07-06 Eli Lilly And Company Herbicidal thiadiazolines
US4346225A (en) 1981-06-15 1982-08-24 Eli Lilly And Company Herbicidal 2-methylamino thiadiazolines
EP2052609A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
DE102008037621A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides

Also Published As

Publication number Publication date
BE744812A (en) 1970-07-22
IL51763A0 (en) 1977-05-31
DE1912543C2 (en) 1985-10-10
JPS5512404B1 (en) 1980-04-02
IL31792A0 (en) 1969-05-28
DE1912543A1 (en) 1969-12-18
IL31792A (en) 1979-01-31
FR2003832A1 (en) 1969-11-14

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Legal Events

Date Code Title Description
414F Notice of opposition given (sect. 14/1949)
414A Case decided by the comptroller ** specification amended (sect. 14/1949)
SPA Amended specification published
PS Patent sealed [section 19, patents act 1949]