GB766690A - 2-mercaptobenzothiazole derivatives and herbicidal compositions containing the same - Google Patents

2-mercaptobenzothiazole derivatives and herbicidal compositions containing the same

Info

Publication number
GB766690A
GB766690A GB17801/54A GB1780154A GB766690A GB 766690 A GB766690 A GB 766690A GB 17801/54 A GB17801/54 A GB 17801/54A GB 1780154 A GB1780154 A GB 1780154A GB 766690 A GB766690 A GB 766690A
Authority
GB
United Kingdom
Prior art keywords
benzothiazylmercapto
mercaptobenzthiazole
benzthiazylmercapto
dimer
trichloroethylene
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
GB17801/54A
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.)
Monsanto Chemicals Ltd
Monsanto Chemical Co
Original Assignee
Monsanto Chemicals Ltd
Monsanto Chemical Co
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 Monsanto Chemicals Ltd, Monsanto Chemical Co filed Critical Monsanto Chemicals Ltd
Publication of GB766690A publication Critical patent/GB766690A/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
    • C07D277/60—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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention comprises (benzothiazylmercapto-2) pentachlorobutene, bis-(benzothiazylmercapto - 2) tetrachlorobutene, tris - (benzothiazylmercapto - 2) trichlorobutene, tetrakis(benzothiazylmercapto - 2) dichlorobutene, pentakis - (benzothiazylmercapto - 2) chlorobutene and hexakis-(benzothiazylmercapto-2) butene and mixtures thereof, and their preparation by reacting 2-mercaptobenzthiazole or an alkali metal derivative thereof with dimeric trichloroethylene. The reaction may be effected by mixing the reactants and allowing the mixture to stand, or by refluxing in an inert solvent, e.g. toluene, ethanol, nitrobenzene or ether. Alkali metal mercaptides mentioned are those of lithium sodium and potassium. In examples (1) 2-mercaptobenzthiazole is treated with ethanolic sodium hydroxide, the mixture filtered, cooled and dimeric trichloroethylene added; after leaving overnight mixture is filtered, and filtrate on standing for a month deposits a condensate of 2-mercaptobenzthiazole and trichloroethylene-dimer; (2) a suspension of sodium mercaptobenzthiazole in ether is treated with dimeric trichloroethylene as in (1); (3) as in (1), but refluxing the reaction mixture, to yield a condensation product in which substantially all the chlorine of the dimer is replaced; (4) mercaptobenzthiazole and the dimer are refluxed in toluene, giving essentially a mono - (benzothiazylmercapto - 2) pentachlorobutene; (5) ethanolic sodium mercaptobenzthiazole and the dimer are refluxed in toluene, and the condensation product obtained crystallized from alcohol.ALSO:Herbicidal compositions comprise the reaction product obtained by condensing 2-mercaptobenzthiazole or an alkali metal derivative thereof with trichoroethylene dimer, (i.e. (benzthiazylmercapto-2)- pentachlorobutene, bis (benzthiazylmercapto-2) tetrachlorobutene, tris (benzthiazylmercapto-2) trichlorobutene, tetrakis (benzthiazytmercapto-2) dichlorobutene, pentakis (benzthiazylmercapto-2) chlorobutene, hexakis (benzthiazylmercapto-2)-butene and mixtures thereof), and a finely-divided solid or a liquid carrier. Oil-in-water emulsions of the active compounds (cyclohexanone is the preferred organic medium), in corporate ionic or non-ionic emulsifying agents, e.g. alkylbenzene sulphonates and polyglycol ethers, and may further include other agricultural pesticides, insecticides and fungicides. Specified solid carriers are clay, pumice, talc and bentonite.
GB17801/54A 1953-06-17 1954-06-17 2-mercaptobenzothiazole derivatives and herbicidal compositions containing the same Expired GB766690A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US766690XA 1953-06-17 1953-06-17

Publications (1)

Publication Number Publication Date
GB766690A true GB766690A (en) 1957-01-23

Family

ID=22133486

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17801/54A Expired GB766690A (en) 1953-06-17 1954-06-17 2-mercaptobenzothiazole derivatives and herbicidal compositions containing the same

Country Status (1)

Country Link
GB (1) GB766690A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0420453A1 (en) * 1989-09-27 1991-04-03 Mobil Oil Corporation Sulphur coupled hydrocarbyl derived mercaptobenzothiazole adducts as multifunctional antiwear additives and compositions containing same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0420453A1 (en) * 1989-09-27 1991-04-03 Mobil Oil Corporation Sulphur coupled hydrocarbyl derived mercaptobenzothiazole adducts as multifunctional antiwear additives and compositions containing same
US5073279A (en) * 1989-09-27 1991-12-17 Mobil Oil Corporation Sulfur coupled hydrocarbyl derived mercaptobenzothiazole adducts as multifunctional antiwear additives and compositions containing same

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