Basf Aktiengesellschaft

Juergen Varwig

Gerhard Hamprecht

Wolfgang Rohr

Heinrich Adolphi

Walter Seufert

Gerd Husslein

Wolfgang Seppelt

Bruno Wuerzer

Norbert Goetz

Ernst Buschmann

Bernd Zeeh

Rainer Becker

Norbert Meyer

Werner Hoffmann

Karl Kiehs

Heinz-Guenter Oeser

Diethers of m- or p-hydroxyphenol, as well as the monoethers, are prepared by reacting m- or p-tert.-butoxyphenol of the formula II ##STR1## with a halogen compound in the presence of a hydroxide, carbonate and/or bicarbonate of an alkali metal or alkaline earth metal and an organic solvent which is inert under the reaction conditions, at from 20.degree. C. to 150.degree. C., and, if desired, reacting the resulting diether with a dilute aqueous inorganic acid at from 30.degree. to 100.degree. C. to give the monoether. The end products which can be prepared by the process according to the invention are useful starting materials for the preparation of dyes, drugs and crop protection agents.

Diethers of m- or p-hydroxyphenol

4H-Pyrido[2,3-d][1,3]oxazin-4-one derivatives of the formula ##STR1## where Y is oxygen or sulfur and R is phenyl which is unsubstituted or substituted by halogen, haloalkyl, haloalkoxy, haloalkylmercapto, haloalkylsulfinyl or haloalkylsulfonyl, are used for controlling undesirable plant growth.

Use of 4H-pyrido[2,3-d][1,3]oxazin-4-one derivatives for controlling

Fluorophthalimides are prepared by a process in which a fluorophthalic anhydride is reacted, in the presence of an aliphatic sulfone, with from 0.4 to 0.8 mole of urea per mole of fluorophthalic anhydride, and the reaction is carried out first at 110.degree.-140.degree. C. and then at 150.degree.-170.degree. C.

Preparation of fluorophthalimides

2-Phenyl-4H-3,1-benzoxazin-4-ones of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or halogen, R.sup.1 may furthermore be methyl or methoxy and R.sup.2 may furthermore be haloalkyl, haloalkoxy, haloalkylmercapto or haloalkylsulfonyl, each of 1 to 3 carbon atoms, are prepared by reacting an appropriate anthranilic acid with an appropriate benzoyl halide in the presence of a base (acylation) and effecting ring closure by removal of water (cyclization), the process being carried out in a suspending agent which is immiscible with aqueous alkali metal hydroxide solution and in the presence of a phase-transfer catalyst.

Preparation of substituted 2-phenyl-4H-3,1-benzoxazin-4-ones

Novel fluoromethylthiobenzoyl fluorides are prepared by reacting a trichloromethylthiobenzoyl chloride with hydrogen fluoride at from 10.degree. to 130.degree. C., and are useful starting materials for the preparation of crop protection agents. The process of the invention is selective in permitting the optional production of either a trifluoromethylthiobenzoyl fluoride or a difluoromonochloromethylthiobenzoyl fluoride, depending upon the temperature employed.

Preparation of fluoromethylthiobenzoyl fluorides

Fluoroethoxyphenyl (di)thiophosphates of the formula ##STR1## where R.sup.1 is alkyl of 1 to 3 carbon atoms, R.sup.2 is alkyl of 1 to 5 carbon atoms, alkoxyalkyl or alkylthioalkyl, each of 2 to 8 carbon atoms, or cycloalkyl of 3 to 6 carbon atoms, R.sup.3, R.sup.4 and R.sup.5 independently of one another are each hydrogen, fluorine, chlorine, bromine or cyano, or alkyl of 1 to 4 carbon atoms which is unsubstituted or substituted by halogen, cyano, alkoxy or alkylthio, X is oxygen or sulfur, and Y is hydrogen, fluorine, chlorine or bromine, their preparation and their use as pesticides.

Fluoroethoxyphenyl (di)thiophosphates, a process for their preparation

2-Trifluoromethylphenyl (di)thiophosphates of the formula ##STR1## where R.sup.1 is alkyl of 1 to 3 carbon atoms, R.sup.2 is alkyl of 1 to 5 carbon atoms, alkoxyalkyl or alkylthioalkyl of 2 to 8 carbon atoms or cycloalkyl of 3 to 6 carbon atoms, R.sup.3, R.sup.4 and R.sup.5 independently of one another are each hydrogen, cyano, halogen, alkoxy, alkylthio, each of 1 to 4 carbon atoms, or alkyl of 1 to 4 carbon atoms, which may be substituted by halogen or cyano, and X is oxygen or sulfur, are used for pest control.

2-Trifluoromethylphenyl (di)thiophosphates, and their use for pest

Novel 4H-3,1-benzoxazine derivatives of the formula ##STR1## where R.sup.1, R.sup.2 and Y have the meanings given in the disclosure, a process for their preparation, and their use for combating unwanted plant growth.

4H-3,1-Benzoxazine derivatives, compositions and herbicidal use

Fluorophthalic anhydrides containing 1 or 2 fluorine atoms are prepared by a process in which a chlorophthalic anhydride containing 1 or 2 chlorine atoms is treated with an acid chloride of sulfurous acid or of carbonic acid in the presence of an aliphatic sulfone, and the reaction mixture is then reacted with potassium fluoride.

Preparation of fluorophthalic anhydrides

Difluoromethoxyphenyl thiophosphates of the formula I ##STR1## where R.sup.1 is alkyl of not more than 3 carbon atoms, R.sup.2 is unsubstituted or substituted alkyl of not more than 5 carbon atoms, Y is hydrogen or chlorine, X is oxygen or sulfur and R.sup.3, R.sup.4 and R.sup.5 are each hydrogen, halogen, nitrile, alkoxy or alkylthio, each of not more than 4 carbon atoms, or unsubstituted or substituted alkyl of not more than 4 carbon atoms, their preparation and their use as agents for controlling pests, in particular insects and other arthropods.

Difluoromethoxyphenyl thiophosphates as pesticides

Trifluoromethoxyphenyl-(di)-thiophosphoric acid esters of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and X have the meanings given in the description, and their use in pest control.

Trifluoromethoxyphenyl-(di) thiophosphoric acid esters and their use in

A novel process for the preparation of phenylpropyl halides of the formula ##STR1## by reacting the corresponding phenylpropyl halides, substituted only by R.sup.2 and R.sup.1, with an alcohol, alkyl halide or olefin; and phenylpropyl halides where R.sup.3 has certain meanings.

Growing community of inventors

Heidelberg, Germany

Juergen Varwig