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United Stat Apr ---...-- RSS KEKEM SA (UUAV G 3 was 34 S. 2 3,506 fa () N v - i 2. ly 22. (a tA 3,506,720 United Stat Apr. 14, 1970 2 of a total of from 2 to 19 carbon atoms, alkyl-sulfonyl 3,506,720 of from 1 to 4 carbon atoms, bromo- and chloro-alkyl HALOGENATED HYDROXY-DIPHENYL ETHERS sulfonyl wherein each alkyl is of from 1 to 4 carbon Ernst Model, Basel, and Jakob Bindler, Riehen, Switzer land, assignors to Geigy Chemical Corporation, Green atoms, and chloro- and bromo-alkyl-carbonyl wherein burgh, N.Y., a corporation of Delaware w "alkyl' is of from 1 to 4 carbon atoms, piperidino No Drawing. Continuation-in-part of application Ser. No. carbonyl, and morpholino-carbonyl; 345,080, Feb. 7, 1964. This application Aug. 8, 1966, "alkanoyl" in the definition of Y having preferably 2 to 4 carbon atoms; or S. ClaimsSer. No. priority, 570,742 application Switzerland, Feb. 22, 1963, - 2,250/63 (b) a compound of the formula Int, C. C07c43/20, 43/22, 121/60 10 U.S. C. 260-613 4 Claims y H Cl ABSTRACT OF THE DISCLOSURE Halogenated-2-hydroxy-diphenyl ethers and esters Hall thereof are useful in Seigigs. compositions and 2-0 methods for the protection organic materials. Illus (IC) trative compounds are 4,2',4'-trichloro-2-hydroxy-di and phenyl ether . and 4,2',4'-trichloro-2-methoxy-diphenyl 20 alkyl ...H Ci ether. smallam Hall S This is a continuation-in-part of our copending appli alkyl35- O X 2 cation Ser. No. 345,080, filed Feb. 17, 1964, now aban 2-0 doned. 25 (ID) The present invention relates to novel halogenated hy wherein droxy-diphenyl ethers and esters thereof, which are useful Z, Hal and m and n have the above-given meanings, the in the control of microorganisms, and for the protection sum of m--n in Formula IC not exceeding 4, of organic materials and articles from microorganisms, X is a member selected from the group consisting of particularly from bacteria and especially from infestation 30 with bacteria and growth of bacteria thereon, more es hydrogen and chlorine, and pecially, in a first aspect, for the disinfection of personal Yi is a member selected from the group consisting of and household linen, and for the protection of such ma hydrogen, alkyl of from 1 to 3 carbon atoms, and terials from growth of microorganisms thereon, and as cyano; - . bacteriostatic agents in bactericidal compositions, for in “alkyl' is an alkyl radical of from 1 to 3 carbon atoms; stance, washing agents and liquors. w (preferably, Y in Formula IA/B has the same meaning Such control of microorganisms, and, particularly, bac as Y1 in Formula IC). teria, and moremena-Wanna especially disinfection of a substrate nor (When, in this specification and the appended claims, mally permitting undesirable growth of bacteria thereon the symbol His linked to a specific position of a benzene and/or protection of said substrate against such growth, 40 nucleus, as in the above and in some subsequent formulas, consists essentially of applying to said substrate a dis this means that that position is only occupied by hydrogen infecting and bacterial growth-inhibiting amount of and not by any other substituent of that ring encompassed (a) a compound of the formula by the respective formula.) (c) a compound of the formula 50 (IE) wherein wherein Hal represents a halogen atom, 55 Z, Hal and n have the same meanings as in Formula IA, m is an integer ranging from 0 to 3, each of Yi, Y2 and Y3 is a member selected from the n is one of the integers 0 to 2, and the sum of m--n is group consisting of hydrogen, alkyl of from 1 to 3 not more than 3; w carbon atoms, and cyano, X is a member selected from the group consisting of p is an integer ranging from 2 to 3; and the sum of chlorine and bromine, and 60 n-p is not more than 3; each Y, independently of the other, represents hydrogen, alkyl of from 1 to 3 carbon atoms, alkoxy of from (d) a compound of the formula 1 to 3 carbon atoms, alkanoyl of from 1 to 4 carbon atoms, -CF3, -CN or -NH2; but preferably not more than one Y is an alkoxy, alkanoyl or NH2 65 group; Z represents hydrogen, alkyl-carbonyl of from 2 to 18 - -carbon atoms, alkenyl-carbonyl of from 2 to 18 carbon atoms, benzoyl, chloro-benzoyl, alkyl-betazoyl wherein Hall “alkyl' is from 1 to 3 carbon atoms, N-alkyl-carbamyl 70 and N,N-dialkyl-carbamyl, each of whose "alkyl' groups is of from 1 to 3 carbon atoms, alkoxy-carbonyl 3 is . ; 3,506,720 3 4. wherein tain a compound falling under Formulas IA/B to F as active ingredients, in a bacteria growth-inhibiting amount, Z, Hal, m, Xi and Y have the meanings given herein are distinguished by slight toxicity for warm blooded before, the sum of m-n is not greater than 5, and, animals and, in conventionally used concentrations, do preferably not greater than 4, not irritate the skin. They are bactericidally effective Y4 is a member selected from the group consisting of both against gram positive as well as gram negative bac hydrogen, alkyl of from 1 to 3 carbon atoms and allyl, teria, for example, against Bacillus mesientericus, Sar and cina, spec. and particularly against forms of coli Such Y5 is a member selected from the group consisting as against Escherichia coli 96 and other gram negative of hydrogen and alkyl of from 1 to 3 carbon atoms, organisms. A further advantage of the halogen-o-oxy at least one of Y4 and Y5 being one of the aforesaid O diphenyl ethers used according to the invention is their members other than hydrogen. colorlessness or slight inherent color. This property en By “halogen" as used in this specification and in the ables them to be used for many purposes for which it is appended claims, there are meant fluorine, bromine, io not possible to use strongly colored known bactericidal dine, and, preferably, chlorine. compounds. Among these preferred halogen-o-oxydiphenyl ethers The above-described compounds used under the first of the foregoing formulas, two sub-groups can be dis aspect according to the invention are not soluble in water tinguished which have particularly good bactericidal ac but some are soluble in dilute sodium and potassium tivity in washing agents and which disinfect washed goods hydroxide solutions and/or in all practical organic Sol ind protect them against growth of microorganims there vents. Because of this solubility, they can be used in very di: i.e. o-oxyphenyl ethers the benzene ring B of which 20 many ways for the combatting of microorganisms, par is unhalogenated, of the formula : ticularly of bacteria, and for the protection of organic materials and objects from attack by microorganisms. They can thus be incorporated directly into the mate rial to be protected, for example in material having a synthetic resin basis, as polyamides and polyvinylchlo ride in paper treatment liquors, in printing thickeners made from starch or cellulose derivatives, in lacquers and (II) paints which contain, e.g., casein, in cellulose, in viscose wherein 30 spinning mass, in paper, in animal mucilages or oils, Hai and Z have the above-given meanings, in permanent dressing having a basis of polyvinyl alcohols, pis one of the integers 2 and 3, and the o-oxydiphenyl in cosmetic articles such as in soaps, e.g., in hand or ethers halogenated in benzene ring B in the p-position toilet soap, in ointments or powders. They can also be to the ether bond, of the formula added to preparations of inorganic or organic pigments 35 for the painting industry, plasticisers, etc. ; X Moreover, the above-described compounds of Formulas 1. 2 IA to IF can be used in the form of their organic Solu tions, e.g. as so-called spray or as dry cleaners or for the impregnation of wood. As organic solvents, preferably Half Z-O 40 those not miscible with water are used, in particular, (III) petroleum fractions, but also water miscible solvents wherein can be used such as low alcohols, e.g. methanol or ethanol or ethylene glycol monomethyl or monoethyl Hal and Z have the above-given meanings and ether. X and X both represent chlorine; or In addition, they can be used with wetting or dis X-represents bromine and X" represents hydrogen, and 45 persing agents in the form of their aqueous dispersions, m represents a positive integer of 0 to 3. e.g. for the protection of substances which tend to rot, In the compounds of Formulas II and III, the benzene such as for the protection of leather, paper etc. ring A can also contain the methyl, the trifluoromethyl or Solutions or dispersions of active ingredient which can the methoxy group. .. be used for the protection of these materials advantage The total number of halogen atoms in the molecule 50 ously have a content of active ingredient of at least 0.001 of these compounds is at most 5; when the benzene rings, g/liter. preferably ring B, further contain lower alkyl groups A preferred use for the diphenyl ether derivatives con which may be halogenated, the light-fastness of the com sists in disinfecting goods which are washed, and pro pounds of Formula III is generally enhanced. Two alkyl tecting such goods from attack by microorganisms.
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