Table Of ContentTHE STHTHXSIS AMD XHSECTICISAL ACTX7ITT OF SOME HALGGEKATED
ABOMATIC OTHERS
A Dissertation
Submitted to the Graduate Faculty of the
Louisiana State University and
Agricultural and Mechanical College
in partial fulfillment of the
requirements for the degree of
Doctor of Philosophy
in
The Department of Chemistry
by
Tien- chih Chen
B-S., National South-western Associated University, 19&L
M.S., Louisiana State University, 19^8
August, 19^9
UMI Number: DP69324
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MANUSCRIPT THESES
Unpublished theses submitted for the master’s and doctor’s
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LOUISIANA STATE UNIVERSITY LIBRARY
119-a
4 93
R2096
ACraOWISDGMEHT
The author wishes to express his sincere appreciation for
the advice and assistance of Dr. W. T. Susaerford? under whose
direction this InvestIgatIon was conducted.
The author is indebted to Dr- J. L. S. Erickson of Louisiana
State Dhiverslty for the use of his laboratory in carrying out
the elementary analyses of the new compounds described herein.
The author is also indebted to Dr. S. W. Simons? Chief?
and to Dr. B. V* l»hy of the Technical Development Division of
the Ccanmunicable Disease Center of United States Public Health
Service at Savannah? Georgia? for the use of the laboratory
facilities and their methods for testing the biological activity
of the compounds prepared in this study.
ii
m m m r n
I* Xtefesodu«t±<m ^ # , X
XX* Review *£ J&teaew&ar© * * » « . » • * * * » * « * 9
X2X* SUsewHtlOB. • « • • * . * * • . . . . * # » + .* 3U»
T. Suanoxy f > * * • » * » « • * • . » • • * » . « # 37
IX. Selected 3&H$g*ig$y « • • • • • « * » * * » » * 39
HI. Yite .............. . . . « b*f
Hi
cast
OtaMMrolallsr iSsg^wTvtia'^ Sthere *ftH#
i*
Xaaoeto acq u it stfcLoli tEhey aero Active « . . .
XX. ASfl&m&$mm of the Williamson's Method
far tte S&rntheeis of Aretmtlc Bthero * « . . ♦
11
XXX. Of tht W*o of DlManltM
Ca^miBdi la ito %nthe»ia of Arcaaatic Ethers • 12
XX. Arotteofttoae ©f Boaetiona tmt&y£og
Mbgtoo&iOM la tto syxrfchoole of AawetMa
f* t o Asplieatiea* of tot Bo*©tion Between
a Ttoaol and on Olofin la th* Synthesis of
t o a t o I t o t • » • # * * • • . * » • • , lb
w « Sew* t o t o t w of ®*nwF«l Ufooollwmoa*
Beeetlene la the Synthesis of Aromatic Bthors 15
* m
TO.
Cooperati** t o t o torfeality o f____
tarte after ^ and to t o * of
tAmeae IbQOOOW* to fee BHiitloao of * * *
Tin. emwmmbtm a m m » Morteli% at confuted
XlMT BwrtXog after s. .Ka.ns.r.. ©.S’ .Xaq.pa.m.mm. .to
W ttM W t Mtt t»Nd( 30
.
a of Adult TTtoni*
) efte* 19 tol 30 SHmte*
[to of 200 mg* per «$. ft*
of TfcMoti* a^beeemted Xttore on 01m s Surface.
x. IWIyN^atotoor tortalltie* of Bat Jfcttee
baeoti) after 30 Minute* Exposure
to tto ltoieatod Percentages of Tfcrioub
t o W t o Ethers la Bjrtropbylllte Dusts * • * * 36
It
Sine* m & 19 predestined to share the earth pith insects,
it is desirable, and In 0m m cases necessary* for hla to con-
tral these vhieh transmit disease* reduce the food 0 9 $^# and
(wnii Ifflwa wf iii i
Chemical gt&a&aaeee, hath natural and synthetic, have been
used in this M M U s t for a long tlaw. She introduction of
2*2~hls(£-chlxxroph*£yl) -XA*X~tPichlor©ethaM (J30T) and its
SBonssful sgplleettexx, as a contact poison ©gainst
species of hungftd insects suggest the possibility of finding
otter u s « M insecticides among the synthetic compounds•
SEN? appears to depend on Its lipophilic CCX^~ group for
penetration of the insect and its chlorinated aryl rings' for
its paralysing affects* ISnxs it appeared earth ahlle to oh*
other **?&*&**&* having lipophilic groups and appropriately
si tasted halogen atone for tasting against harmful insects*
Therefore* a series of sixteen aliphatlc-aroinatic ethers
halogenated in either or hath the a&yl and aryl group was
synthesised hy standard procedures. These ethers were tested
Individually against three types of harmful insects and one
tenfid Aveofcnlda bar exposing the test organisms to predeter*
mined quantities of the compounds deposited on suitable surfaces#
y
An ineature flying insect (mosquito larvae), a mature flying
insect (bona* flies)# «qS a mature crawling insect (confused
flour beetles) and a fcanafuX Arachnid* (rat mites) were se
lected Mr these biological testa# EE&P ms mad as the refer-*
standard wfffie ist w'Mi of the tests with these
organisms*
Sena of the ecrapounds sere inactive against the Indicated
organises trader the conditions of our testa# Others were quite
active* end In oats oaf tee instances* their activity exceeded
that eT KBf« Shis Indicates that it is possible to build an
around the ether Xinhage in oonjeietion
' with me pesiasoO' of atoms in either the or
aromatic portions of the molecule*
It is likewise obvious that these features characteristic
of certain oseenS* round to he active nust he associated with
a molecular configuration of a certain degree of specificity
for swriml insecticidal activity#
She 3-chlorinated ally! ethers were definitely superior to
the iscrasrle 2~chlor1nate& allyl ethers as fudged by the degree
of Mortality in the four types of test organisms* the subetitu-
time of railtlple halogen atoms in the phenyl group of aliphatic*
aromatic ethers failed to enhance the basicity of the compounds
toward the test erganlsnis • She o* chlorinated benzyl ethers of
the p-sUbstituted phenols were more active than the correspoiiA-
ing benzyl ethrafs except in the case of rat mites#
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