Ciba-geigy Corporation

John G Dingwall

Brian Tuck

Barry Cook

Laurenz Gsell

Pierre Martin

Peter Ackermann

Donald Richard Randell

Eric K Baylis

Hans Greuter

Colin D Campbell

Alan Marshall

Peter Miles

Brian Martin Thomas

The new compound 4-chloro-4-chloromethyloxetan-2-one can be prepared by reacting diketene with sulphuryl chloride under conditions in which free radicals are formed. The 4-chloro-4-chloromethyloxetan-2-one exhibits antimicrobial activity. It is also useful as an intermediate, for example for the production of pigments and dyestuffs.

4-Chloro-4-chloromethyloxetan-2-one

4-Chloro-4-chloromethyloxetan-2-one and a process for its production

Compounds having the formula ##STR1## are described, wherein X is oxygen or sulphur or the moiety X is absent and A and D are as defined in claim 1. Compounds I may be prepared by reacting a compound ##STR2## with diketene in the presence of an agent capable of forming free radicals. They are useful as friction modifiers and/or antiwear additives in lubricating oils or for imparting flame-retardancy to natural or synthetic polymers.

Phosphorus substituted 4-methyloxetan-2-ones, processes for their

Novel compounds having the formula I ##STR1## are described wherein X is a chlorine, bromine or iodine atom and Y is a residue having the formula R.sup.1 R.sup.2 R.sup.3 C- wherein R.sup.1 and R.sup.2 are the same or different and each is a fluorine, chlorine or bromine atom and R.sup.3 is a hydrogen, fluorine, chlorine or bromine atom, a group -CR.sup.4 R.sup.5 R.sup.6, a cyano group, a group-COR.sup.7 or -PO(R.sup.8).sub.2 wherein R.sup.4, R.sup.5, R.sup.6, independently, are F, Cl or Br, R.sup.7 nd R.sup.8 are the same or different and each is a chlorine atom or a group -OR.sup.9 wherein R.sup.9 is a C.sub.1 -C.sub.4 straight chain or branched alkyl group with the proviso that when X is a chlorine atom, none of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, can be a bromine atom. They can be obtained by reacting diketene with a compound XY in the presence of an agent capable of forming free radicals. Compounds (I) have biocidal activity against various organisms, e.g. bacteria, fungi and algae.

4-Halgeno-oxetan-2-ones and process for their production

There is described a new process for the preparation of optically active 2-(2',2'-dihalogenovinyl)-cyclopropane-1-carboxylic acids substituted in the 3 position, and derivatives thereof. A racemate of certain cyclobutanones is reacted with a sulfurous acid salt of an optically active base to obtain a mixture of diastereomeric 4-(2',2',2'-trihalogenoethyl)-cyclobutane-2-sulfonic acid salts; this mixture is then separated into the pure diastereomeric sulfonic acid salts. Either the pure diastereomeric sulfonic acid salts are converted directly to the desired optically active products, or the optically active cyclobutanones obtained from the pure diastereomeric sulfonic acids salts by decomposition are converted, in the presence of a base, to the desired product. Optionally, the product, optically active 2-(2',2'-dihalogenovinyl)-cyclopropane-2-carboxylic acids can be converted to their 1',2'-dibromo derivatives.

4-(2',2,2'-Trihalogenoethyl)-cyclobutane-1-sulfonic acid salts with

There is described a new process for the preparation of optically active 2-(2',2'-dihalogenovinyl)-cyclopropane-1-carboxylic acids substituted in the 3 position, and derivatives thereof. A racemate of certain cyclobutanones is reacted with a sulfurous acid salt of an optically active base to obtain a mixture of diastereomeric 4-2-(2',2',2'-trihalogenoethyl)-cyclobutane-1-sulfonic acid salts; this mixture is then separated into the pure diastereomeric sulfonic acid salts. Either the pure diastereomeric sulfonic acid salts are converted directly to the desired optically active products, or the optically active cyclobutanones obtained from the pure diastereomeric sulfonic acids salts by decomposition is converted, in the presence of a base to the desired product. Optionally, the product, optically active 2-(2',2'-dihalogenovinyl)-cyclopropane-1-carboxylic acids can be converted to their 1',2'-dibromo derivatives. SU

Process for producing optically active

A compound or mixture of compounds of the general formula: ##STR1## in which m and n may be 0 or 1 but both cannot be 1, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently H or CH.sub.3, X.sup.1, X.sup.2, Z.sup.1 and Z.sup.2 are independently hydrogen or straight or branched chain C.sub.1 -C.sub.4 alkyl; and the water-soluble inorganic or organic salts thereof, with the proviso that at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 must be CH.sub.3, and when m and n are both 0, R.sup.2 and R.sup.3 are each methyl and R.sup.4 and R.sup.5 have their previous significance, when added to an aqueous system imparts one or more of the following beneficial effects to be treated system:

Method of treating aqueous systems with phosphonoadipic acids

A compound or mixture of compounds of the general formula: ##STR1## in which m and n may be 0 or 1 but both cannot be 1, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently H or CH.sub.3, X.sup.1, X.sup.2, Z.sup.1 and Z.sup.2 are independently hydrogen or straight or branched chain C.sub.1 -C.sub.4 alkyl; and the water-soluble inorganic or organic salts thereof, with the proviso that at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 must be CH.sub.3, and when m and n are both 0, R.sup.2 and R.sup.3 are each methyl and R.sup.4 and R.sup.5 have their previous significance, when added to an aqueous system imparts one or more of the following beneficial effects to be treated system: (a) the corrosion of ferrous metals in contact with the system is inhibited; (b) the precipitation of scale-forming salts of calcium, magnesium, barium and strontium from the treated aqueous system is inhibited; and (c) inorganic materials present in the treated aqueous system are dispersed.

Phosphonoadipic acid additives to aqueous systems

Agent for influencing plant growth, in particular a herbicidal and plant growth-inhibiting agent containing in addition to carriers and/or other additives, at least one compound of the formula: ##STR1## in which R is hydrogen an alkyl group having from 1 to 5C atoms, which is unsubstituted or substituted by hydroxyl, salts thereof with either strong monobasic or polybasic acids or with inorganic or organic bases, or optical isomers thereof, as the active component.

Agent and method for influencing plant growth

The present invention relates to new phosphonous acid derivatives, especially to .alpha.-amino-phosphonous acids and processes for their production. The new phosphonous acids are valuable chemotherapeutica in the treatment of pathogenic bacteria, gram-negative bacteria and yeast.

.alpha.-Amino-phosphonous acids for inhibiting bacteria and yeast

A method of treating an aqueous system to inhibit the corrosion of metals in contact therewith and/or inhibit the deposition of scale therefrom comprising adding to the aqueous system a minor proportion of a compound of the formula: ##STR1## wherein n is 0 or 1 and when n is O, R.sub.3 and R.sub.4 are the same or different and each is hydrogen, an alkyl group having from 1 to 4 carbon atoms, a benzyl, allyl, --CH.sub.2 PO.sub.3 H.sub.2 -- or --CHCOOH.CH.sub.2 COOH group or a group of formula ##STR2## wherein R.sub.5 is hydrogen, a methyl, --CH.sub.2 COOH or --CH.sub.2 CH.sub.2 COOH group and Z is a group --COOH or --PO.sub.3 H.sub.2, with the proviso that when Z is a PO.sub.3 H.sub.2 group then R.sub.5 is hydrogen or methyl, and when n is 1, R.sub.1 and R.sub.2 are the same or different and each is hydrogen, or a methyl or phenyl residue and R.sub.3 is hydrogen and R.sub.4 is hydrogen, an alkyl group having from 1 to 4 carbon atoms or a --CH.sub.2 CH.sub.2 COOH group, or R.sub.3 and R.sub.4 together may form a methylene group .dbd.CH.sub.2.

Corrosion inhibitors

Novel 4-(3,5-dialkyl-4-hydroxyphenyl)-1,2-dithiole-3-thiones are used as additives for organic materials. They are prepared by reacting a corresponding alkylated phenol with sulfur and if necessary reacting the resulting compound with sodium disulphide and then with a corresponding halide.

4-(3,5-Dialkyl-4-hydroxyphenyl)-1,2-dithiole-3-thiones

Novel (3-thioxo-1,2-dithiol-4-yl)substituted triaylphosphates and thiophosphates are used as additives for lubricating oils. The are prepared by reacting corresponding phosphoryl chlorides with 4-(hydroxy-aryl)-1,2-dithiole-3-thiones.

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Sale, United Kingdom

John G Dingwall