(Contribution from the Basic Sciences Research Department, U. S. Naval 

 Civil Engineering Research and Evaluation Laboratory) 



STUDIES ON SYNIHSTIC PPffiNOLS .AND ARYLAIiINF,S FOR fclARINS BORER INHIBITION 



By Thomdyke Roe, Jr., Robert L. Alurabaugh, and Herbert McKennis, Jr. 



One approach to the problem of deterioration of wooden structures by 

 marine borers lies in economical synthetic pesticides which can effectively 

 preserve woods over a long peri-^d of time. Sjrnthetic organic chemicals 

 have received wide usage in the preservation of tiibers whore utilization 

 is restricted to non-marine conditions, w'any of these compounds belong 

 to the general class of .aromatic alcohols called phenols. In Figure I, 

 four coiiiraon nitrophenols vfhich have enjoyed some popularity as preserva- 

 tives are shown. Introduction of the nitro group enhances fungicidal 

 activity, but probably contributes to the corrosive action of the phenols 

 on fastenings (l). 



Chlorinated phenols (Fig. I), especially the familiar pentachlorophenol, 

 have found wide applicatioh, Pentachlorophenol, i/irhile effective in many 

 environments, is not reconrraended for conditions where wood T;ill be immersed 

 in salt water (2). 



It is interesting that Clapp and Richards reported that creosote ivhich 

 was low in phenols (cresylic acids) had lost some of its effectiveness 

 as a marine borer deterrent (3). Phenols as a group are noted for the 

 T/ide biological spectra of their toxic activity. The series of phenols 

 currently under study in this laboratory are all derived from benzylamine 

 and are illustrated in Fig, IV, 



Presence of the amino group may serve to inhibit corrosive action. This 

 point, however, has not been investigated. The series is of further 

 interest since many of the intermediates in the chosen synthetic routes 

 have been shown to possess or are related to compounds with marked local 

 anesthetic activity. 



Local anesthesia, according to the theory of Thimann, results from inter- 

 ference with the production or utilization of acetylcholine (U), The 

 experimental work of Bullock establishes a close relationship between 

 inhibition of choline sterase and production of local anesthesia, (5). 

 Many economic poisons may, in part at least, ovje their effectiveness to 

 interference with acetylcholine metabolism vdiich is attributable to their 

 inhibition of choline sterase (6), 



Figure V shows the preparation of three para-substituted benzyl morpholines. 

 The para nitro and the para anino compounds are both known to possess local 

 anesthetic activity (7). 



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