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United States Patent 0 Igatented Oct 2,767,173 United States Patent 0 igatented Oct. 16, 1955 2 the 4-chloro, S-chloro, 4-bromo, S-bromo, 3,5-dichloro, 3,5—dibromo, the various trichloro and tribrorno and tetrachloro thiosalicylhydrazides, the corresponding disul 2,767,173 ?des (dithiosalicylhydrazides), as well as benzyl and BACTERICIDAL AND FUNGICIDAL COMPOUNDS 5 benzal (benzylidene) and hydroxy, halogen, alkoxy and lower-alkylsulfonyl-substituted benzyl and benzal hy Leon Katz, Spring?eld, N. 3., assignor to Sehenley Indus drazides of thiosalicylic and the halogen-substituted thio tries, 130-, New York, N. Y., a corporation of Delaware salicylic acids and the corresponding disul?des of these No Drawing. Application April 22, 1953, hydrazides. The new benzal-substituted thiosalicylhy~ Serial No. 350,510 drazides may be represented by the general formula: 6 Claims. (Cl. 260-441)) HS The present invention relates to new compounds which 15 Y are derivatives of thiosalicylhydrazide, possessing re markably high fungicidal and bactericidal activity. I have found that, whereas the known salicylhydrazide in which X and Y are optional substituents; X may be one has little or no antifungal activity in vitro against such or more (maximum of four) halogen substituents of the organisms as Trichophyton menmgrophytes, Microspor 20 group consisting of chlorine and bromine and Y may be um gypsezzm, and Nocardia asteroides, its sulfur isologue, one or more (maximum of ?ve) substituents of the group thiosalicylhydrazide, surprisingly is remarkably active consisting of chlorine, bromine, loWer-alkyl and lower against these organisms. I also have found that 2,4-di alkoxy substituents, including particularly those required chlorobenzalthiosalicylhydrazide, having the formula to produce the 2,4-dichloro, 3,4-dichloro and Z-methoxy 25 benzal hydrazides of thiosalicylic and substituted dithio salicylic acids. Included also are the disul?des repre sented by the general formula HS 30 X X S-S is even more active than thiosalicylhydrazide itself and that thiosalicylhydrazide is readily oxidized to the disul ?de (dithiosalicylhydrazide) which itself is even more 35 active than the parent thiol against these organisms. The bactericidal and fungicidal activities of both the thiols and the disul?des are increased and other desirable pro perties are imparted thereto by the presence of various in which X and Y have the signi?cance hereinbefore as substituents in the compounds, as more speci?cially 40 signed. pointed out hereinafter. Compounds in which the phenyl portion of the benzal By the terms “thiosalicylhydrazide” and “dithiosalicyl radicals of the foregoing formulae are replaced by hydrazide,” as used throughout this speci?cation, I refer quinolyl radicals, such as are formed by the reaction of to, as thiosalicylhydrazide, the compound represented by a formylquinoline (quinolinecarboxaldehydes), particu the formula: 45 larly 2 and 4-formylquinolines, with thiosalicylhydrazide or dithiosalicylhydrazide, are also characterized by excellent bactericidal and fungicidal properties. Q-o O-NH—NH2 The corresponding benzyl compounds, obtained by I SN reduction of the benzal compounds, are also active 50 bactericides and fungicides. and, as dithiosalicylhydrazide, the compound represented The compounds of the present invention may be repre by the formula: sented by the following skeletal formula: 55 in which R is an ortho-phenylene radical which may be substituted by one or more chlorine or bromine atoms: I W is an amino, benzalimino (benzylidenimino, CeHsCH=H—) .by analogy with such designations as salicylamide and salicylanilide. Related compounds are referred to by 60 or benzylamino radical that may be substituted by one similar designations. or more hydroxy, chlorine, bromine, lower-alkyl, lower The thiol (thiosalicylhydrazide) is also known as thio alkoxy or lower-alkylsulfonyl radicals, or it may be a salicylic acid hydrazide, thiosalicyloylhydrazine, l-(or radical of the formula —N=CI-I——Q in which Q is a thomercaptobenzoyl)hydrazine and similar designations, quinolyl radical such as a 2 or 4-quinolyl radical; and while the disul?de (dithiosalicylhydrazide) is also re 65 Z is a hydrogen atom or a radical identical with the ferred to as bis-(benzoic acid hydrazide) ortho disul?de, —S—-R—CO—NH—W radical. 2,2.’-bis-carbohydrazinodiphenyl disul?de, and similar By virtue of the bactericidal and fungicidal activities resignations. possessed by the compounds of the present invention, The compounds of the present invention include thio and their comparatively low toxicities to humans, they salicylhydrazides, including thiosalicylhydrazide itself, 70 are especially adapted for use in therapeutic compositions 2,767,173 _ p i k ‘H " ‘ I} . d V _ for topical application. They may, however, be used, as acids, the following thiosalicylic acids have been_pre are other ‘fungicides, in compositions for the preservation pared: . V ' t of wood, textiles and other ?bres that are subject to mold attack. .These compounds are also starting materials for the production of N-benzylidene and N-quinolylmeth Thiosalieylic Acid ' M.P , °o. ylene-substituted Z-aminobenzisothiazolones, such as are 1. 4 Chloro -__-_-__- 195‘196 described and claimed in my copending applications ‘with 2. 193-194 William Schroeder, Serial No. 478,507 and 478,508, ?led 3. ' 196-198 4. 210-211 December, 29, 1954. 5. 3,5-D1bromo- _____ __ 221-222 6. 4-Methylsulfonyl- ____ __ 180-181 10 7. 4-Methoxy- ________________________ .1 _______ I. ...... __ 240 , Preparation of thiosalicylic and substituted ' thiosalicylicr acids. ' Preparation of dithiosalicylic acids 7 7' _ Thiosalic'ylic acid and its‘ hydrazide and‘ their deriva v Dithiosalicylic acid,’fromwhichthiosalicylic acid may V15 tives oxidize to the corresponding disul?desonexposure be obtained, can be prepared by known methods. ‘ ' to air. ‘However, for purpose of complete. conversion ' Thios‘alicylic acid can be“ prepared by the method de-. a and preparation of thecorresponding disul?des, the re ' scribed in Organic Syntheses, vol. 12 (1932), page 77, action can be hastened'with mild oxidizing agents such which involves a reduction of dithiosalicylic acid with as halogens, particularly iodine. The preparation of 5,5,’- ' .zinc and acetic acid, or preferably, with sodium hydro 20 dichlorodithiosalicylic acid, which is a typical procedure, sul?te in alkaline solution- Thiosalicylic acid can also may be conducted as follows: , ' a ' ‘ be- prepared by diazotization of anthranilic acid with Three (3) grams, of ‘5-chlorothiosalicylic acid, pre sodium nitrite; and condensation of the diazonium solu- ' pared as described hereinbefore, is dissolved in 50 mil! 1 7 tion with potassium ethyl xanthate, followed by hy liliters of methanol and slightly more than one equivalent . drolysis; 'This latter general method i'srused for the 26 (approximately 2.1 grams) of iodine crystals are, added prepartion of substituted thiosalicylicracids because sub thereto. The solution is allowed to stand at room tem-, ' stituted anthranilic acids are more readily available or perature for several minutes and the precipitated 5,5'-di can be more easily prepared than the substituted di chlorodithiosalicylic acid is separated by ?ltration. ;The thiosalicylic acids. The preparation of S-chlorothiosali product has a melting point of 326-328" C., and; weighs ' cylic acid 30 approximately 2.8 grams. On recrystallization from’ a mixture of methyl cellosolve, methanol and Water, its melting point is increased to 330° C. Its formula is 01 Cl 85 which is a typical method ‘of preparing substituted thio OOOH ' JJOOH V > salicylic acids, may be e?ected as follows : Preparation of alkyl esters of thiosulicylic and . .A solution of 94 grams (0.545 mole) of 5-chloroan 40 substituted thiosalicylic acids. - , thranilic acid, 23 grams (0.55 mole) of sodium hydroxide Alkyl esters of thiosalicylic and substituted thio and 34.5 grams (0.545 mole) of sodium nitrite in 650 milliliters of water is added slowly and with good agita salieylic acids can be readily prepared ‘by. conventional: procedures of esteri?cation with alkanols. A preferred tion to a mixture of 150 milliliters of concentrated hy method is that typi?edby the following preparation of drochloric acid'ancl 200 grams of ice in a beaker im methyl thiosalicylate: . ' 7 mersed in an ice bath, while the temperature is main 'Into a solution of thiosalicylic acid in approximately tainedfbetween 0 and 5° C. After completion of the 7 addition of the solution, 10 volumes of methanol, which is heated to and ,heldjat' the mixture is stirred for 30 a‘ temperature su?icient to maintain’ a gentle re?ux, a minutes and neutralized to Hydrion paper with potassium stream of dry hydrogen chloride gas is passed slowly ,for acetate. The cold diazonium solution is then charged, 50 in a thin stream, into a beaker containinga solution'of a period between approximately 8 and approximately 10 250 grams (1.55 moles) of potassium ethyl xanthate in hours. The excess methanol is then evaporated‘and the 800 milliliters of water that has been heated to 75~80° ester is recovered by vacuum distillation. The ester is, 7 thus obtained in a yield of approximately 80 to 85% of C. andris stirred vigorously. The temperature is main the theoretical. Its boiling point is 115-119" C. at a tained at 7,5-80° C. during the addition, which is ac cm companied by a copious evolution of nitrogen. Some .0. pressure of 1 .to 2 millimeters. Small proportions of oily material may separate during the reaction. The re methyl dithiosalicylate, which has a melting point of: action mixture is cooled, acidi?ed to approximately pH 130-132° C., may be recovered from the residue, 7 3 with concentrated hydrochloric acid and the aqueous In this manner the methyl esters of each of the fore phase is decanted from the semi-solid ‘sludge that forms. , 1 going thiosalicylic acids'were prepared. The melting ' points of those which were characterized, were as “The sludge is dissolved in 400 milliliters of 10% follows: aqueous sodium hydroxide solution and'heated on a steam bath for approximately 2 hours.
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