Patent GB-1059799-A (GB)
Title: Benzothiadiazole esters of phosphorus acids and their use as pesticides
Inventor: HACKMANN JOHANNES THOMAS
IPC: C07D277/62
Filed: 1964-12-08
Abstract: The invention comprises compounds of the formula <FORM:1059799/C2/1> wherein R1 and R2 each represents an alkyl or alkoxy group; each Y individually represents a hydrogen or halogen atom, a nitro group or an alkyl group containing 1 to 4 carbon atoms and X represents an oxygen or sulphur atom.  They are prepared by reacting the appropriate (thio) phosphoric, (thio) phosphonic or (thio) phosphinic acid chloride with the appropriate hydroxy- or mercapto-1,2,3-benzothiadiazole in the presence of a base or with an alkali metal derivative of an hydroxy- or mercapto-1,2,3-benzothiadiazole. The reaction is suitably carried out in an inert organic reaction medium, e.g. benzene, toluene, xylene, acetone or preferably methyl isobutyl ketone at room temperature or slightly elevated temperature.  Suitable bases are pyridine, a trialkylamine in which the alkyl groups contain 1 to 5 carbon atoms or preferably an alkali metal carbonate such as potassium carbonate. A copper catalyst may be used to increase the reaction rate.  The compounds may be used as pesticides (see Division A5).  The 5-hydroxy-1,2,3-benzothiadiazole used as starting materials may be prepared by diazotization of 4-nitro-2-aminothiophenol, cyclization of the diazotization product to give 5-nitro-1,2,3-benzothiadiazol and replacement of the nitro group by a hydroxy group using the usual reduction, diazotization and hydrolysis procedures. 6-Hydroxy-1,2,3-benzothiadiazole may be prepared in a similar manner by employing 5 - nitro - 2 - aminothiophenol as starting material. Where halogenated hydroxy-1,2,3-benzothiadiazoles are required as starting materials they may be obtained by direct halogenation of hydroxy-1,2,3-benzothiadiazoles.  Similarly, nitro - hydroxy - 1,2,3 - benzothiadiazoles may be prepared by direct nitration of hydroxy-1,2,3-benzothiadiazolesALSO:A pesticidal composition comprises a carrier or a surface active agent, or both a carrier and a surface active agent and a compound of the formula: <FORM:1059799/A5-A6/1> wherein R1 and R2 each represents an alkyl or alkoxy group; each Y individually represents a hydrogen or halogen atom a nitro group or an alkyl group containing the 4 carbon atoms and X represents an oxygen or sulphur atom (see Division C2).  The carrier may be a solid, a liquid or a compressed gas e.g. clays, silicates, synthetic hydrated silicon oxides, resins, waxes, synthetic polymeric materials, carbon, sulphur, water alcohols, ketones, aromatic hydrocarbons, chlorinated hydrocarbons, suitable petroleum fractions, trichloromonofluoromethane or dichlorodifluoromethane.  Anionic, cationic or nonionic surface active agents may be used and take the form of an emulsifier, wetting agent, dispersing agent or sticker.  Examples of suitable surface active agents are alkylaryl sulphonates, alkyl sulphates containing more than 10 carbon atoms, alkylphenol/ethylene oxide condensates, sorbitan esters of fatty acids, alkylamide sulphonates and ethylene oxide/fatty acid ester condensates.  he composition may be formulated as a wettable powder, dust, granules, a concentrate, a solution, an emulsifiable concentrate, a conventional emulsion, an invert emulsion or aerosol or an encapsulated material.  Combinations of the compounds with known pesticides and/or fertilizers may also be used.