Patent GB-998920-A (GB)
Title: Phosphorus-containing nitrophenyl esters
IPC: C07F9/12
Filed: 1963-12-20
Abstract: The invention comprises compounds of the general formula <FORM:0998920/C2/1> in which R is a (C1-C12) straight or branched chain, unsubstituted or substituted alkyl, cycloalkyl or aryl radical, R1 and R11 which may be the same of different, are (C1-C8) unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aralkyl or aryl radicals which may be linked directly to the phosphorus atom or via an oxygen, sulphur or nitrogen atom, X is an oxygen or sulphur atom and n is 0 or 1.  They may be prepared by reacting an ester monohalide of the general formula <FORM:0998920/C2/2> in which R1, R11 and X have the same meanings as above and Hal is a halogen atom, with a mononitrophenol of the general formula <FORM:0998920/C2/3> in which R and n have the same meanings as above, the phenol being used in the form of a salt or the reaction being carried out in the presence of an acid-binding agent such as alkali metal alkoxides and carbonates, and tertiary amines.  The reaction is preferably carried out in the presence of inert organic solvents such as unchlorinated or chlorinated aliphatic or aromatic hydrocarbons, alcohols, low boiling aliphatic ketones and nitriles.  The reaction is conveniently effected at slightly to moderately elevated temperatures.  Preferred R groups are methyl, methoxy-carbonyl-methyl, ethyl, hydroxyethyl, propyl, isopropyl, n-butyl, cyclohexyl, isooctyl or n-dodecyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl or nitrophenyl radicals, whilst R1 and R11 preferably denote methyl, ethyl, chloromethyl, isopropyl, isobutyl, isooctenyl, methoxyphenyl, ethylthiophenyl, isopropoxy, chloroethoxy, methylmercapto, ethylmercapto, isopropyl mercapto, chloroethylmercapto radicals or mono- or di - methyl - (-ethyl, -cyclohexyl) - amino groups. The compounds have pesticidal properties (see Division A5).  The mononitrophenols used as starting materials can be prepared by reacting the corresponding monochloromononitrophenols with a mercapto compound R-SH, where R has the same meaning as above, the reaction being effected in a liquid medium in the presence of an inorganic base at a temperature of 0 DEG  to 120 DEG  C.  Specification 955,310 is referred to.ALSO:A pesticidal composition comprises a solid or liquid diluent or carrier in admixture with a compound of the general formula <FORM:0998920/A5-A6/1> in which R is a (C1-C12) straight or branched chain, unsubstituted or substituted alkyl, cycloalkyl or aryl radical, R1 and R11 which may be the same or different, are (C1-C8) unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aralkyl or aryl radicals, which may be linked directly to the phosphorus atom or via an oxygen, sulphur or nitrogen atom, X is an oxygen or sulphur atom and n is 0 or 1 (see Division C2). Suitable solid carriers are talc, chalk, bentonite and clay and suitable liquid carriers are water, alcohols, ketones and liquid hydrocarbons. The compounds of the above formula may also be used in combination with each other or with, for example, other insecticides and/or fertilizers.  A typical liquid composition contains dimethyl formamide, a commercial emulsifier consisting of a benzyl hydroxy diphenyl polyglycol ether containing about 10 to 15 glycol ethers and water.