Abstracts of foreign and domestic patents relating to derris, lonchocarpus, tephrosia, and rotenone

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Title:
Abstracts of foreign and domestic patents relating to derris, lonchocarpus, tephrosia, and rotenone
Physical Description:
69 p. : ; 27 cm.
Language:
English
Creator:
Roark, R. C ( Ruric Creegan )
United States -- Bureau of Entomology and Plant Quarantine. -- Division of Insecticide Investigations
Publisher:
U.S. Dept. of Agriculture, Bureau of Entomology and Plant Quarantine, Division of Insecticide Investigations
Place of Publication:
Washington, D.C
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Subjects / Keywords:
Patents -- Bibliography   ( lcsh )
Botanical insecticides -- Patents   ( lcsh )
Botanical insecticides -- Abstracts   ( lcsh )
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abstract or summary   ( marcgt )
bibliography   ( marcgt )
federal government publication   ( marcgt )
non-fiction   ( marcgt )

Notes

General Note:
Cover title.
General Note:
Erratum slip inserted--P. 2.
General Note:
"E-446 ; August 1938."
Statement of Responsibility:
by R.C. Roark.

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University of Florida
Rights Management:
All applicable rights reserved by the source institution and holding location.
Resource Identifier:
aleph - 030261625
oclc - 03911859
Classification:
lcc - Z5356.L5 R6 1938
System ID:
AA00022942:00001


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August 1938


United States Dar.'tment of Agriculture
Bureau of Entomology and. Plant Quarantine


ABSTRACTS OF FOBZTGi% AND DOi.E.TIC PANTS hS~LATICG 0

MDERRIS, LO0ICHOCARPUS, TSFHROSIA, AND ROTE-JOIZ

(From the time the first application for a patent on dcrris
v1a.s filed (ebruery 8, 1911) to April 1938

By R. C. RoLark, Division of Insecticide Investigations


Elev..1 n countries have sued patents which _ov,.i' derris, cubc,

tephrosia, or rotenone products aLs insecticides, methods of extracting

rotenone from plants, or procosos of mnkiug dihydrorotenone or other

derivatives.

The number of patents gr?.ntcd. by each country is shown in the

following list:

Country 'THrb.r of .atcnt7

Australia 3

Canad. 14

F''Onc e 6

Germany 7

Great Britain 23

Jap.-. p3

Johore 1

T thecrlnnds 1

S'-cden 2

Switzcrland 1

United States of Ar.- rica 49

Total 110


S-446






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Australiman Patents:

McDougall and Howles (59), in Australianm ptznt 18,227/24, issued
Novcmbcr 10, 1924, applied for Juno 16, 1924, moake identical claIlms to
the invention described in British patent 226,250.

The Zaidan Hojin Rikag.akv Koukyujo (110), in Australian patent
15,327/28, issued July 24, 1929, applied for August 28, 1928, in J'papo,
Novemfoor 16, 1927, claims powdered insecticide proparcd by causing the
active ingredients of the root of dorris species to be absorbed by an
earth or earths such as clay, china-clay, earthenware clay or kieselruhr,
which is or are free from water, alkali, and like subst-ances detrimental to
the active i.-..redionts, aiding thereto a suitable quantity of .-.,ncsium
carbonate, calcium carbonate, or like adhesive medium, and cr-ishirng the
reosull',.nt mixture to powder.

xnles marc (I) twenty-fiv;e -r.is of powder of powdered dry roots
of dcer:,is are extracted, ith a half pound of other, and, while the liquid
is tated, 150 rams of dry kieosolgu'ahr caro added. The other is then
recovered. This kicsolguhr contai!iin& the absorbed active ingredient is
mixed with 2 grais of po-d.crcc3 :ulphur, 2 grens of pord.ered resin, and 45
~,r:.s of magncsium carbonat-. The nixturic is then finely powdered. by a
cmrsher. (2) Fifty grams of raw root of 6orris arc crushed and urcssed,
and the juice is collected. This operation is repeated two or more times.
To the juice, thus obtained, 150 grain of reddish earth is &..ud, and the
water content of the mixture is entirely driven off as by a vacuuI evaopor-
ator under low tonmporature. This earth containing the absorbed active in-
gredients is mixed with quantities of powdered nulphur, -,ow;dlered resin,
and mangnesiu. carbonate as in the previous cxnple. The resultant mixture
is then finely ,o.-. ere'-I by a crusher.

The Inporial Chcnical Industries of Australia and New Ze-mland
Ltd. (45), in Australian patent 20,894/35, issued February 14, 1235, applied
for January 11, 1935, claims a method of treating sheep or other aninals
in order to render them i-'--mL- from attack or infestation by blow flies or
the like, which consists in subjecting the aimiials to trcatnont with a
solution or a suspension ;ontainim one of the :.an-ithates. ir. insocticidal
agent such as a silicofluorido, derris, pyrethrun, etc., nay be ar:'.loed.
One of the clai:.s reoad.s: "A new article of manufacture for the purposes
indicated, produced by -i-:in.2 to,-ether the followi-.g substances substan--
tialIy in the proportions indic:.toe':--

potassium ethyl xanthate .......... 8 parts
dorris root powder ................... 4 parts
bcntonite .................... ..... 2 parts
sulphon',vto'e- cod oil ............... 1 part"


British Patents:

HcDougall, McDougall, and McDoulo;all (63), in British patent 3,204,
issuoEd May 8, 1912, applied for February 6, 1911, claim in the nanufacturc











Correction for E-446


The following information should be inserted on p., e 22
after the ) lines at the top of the pace. These patents, although
in E-402 (Tephrosia as an insecticide a review of the literature,
Feb. 1937) and two of which are also referred to on page 17 of the
present publication were inadvertently omitted from the abstracts of
United States Patents, beginning on page 21.

Lemmens and Fryer, in United States patent 1, 242,54 issued
October 16, 1917; applied for January 16, 1917; claim a parasiticidal
preparation comprising comminuted parts of Tephrosia, and a soap vehicle.

"In the manufacture of a sheep dip, in accordance with
the present invention, the seeds, leaves, a=Id other portions
of the plant are ground to powder and if desired mixed with
other ingredients. In th namarufacturc of an insecticide for
use for the destruction of plant pests, the ground material
may be mixed with soap, silltur, or other substances. The
said ground material may also be mixed with various other
substances to form preparations for the destruction of earth-
worms, grubs, and the like. Thu compound contained within
the material is extractable therefrom, when in a finely di-
vided state, by moisture or by immersing the material in
water. The said compound when extracted then mlixes with the
substances which may be added to the ground material to produce
the dosir"d finished product re.." for use for dipping or
spraying." Softc:la", reagents, antiseptics or bactericidcs
may be added thereto.

Lemmens and Fryer, in United States patent 1,242,9b55 issued
October 16, 1917; applied for January 16, 1917; claim a new anti-
par.sitic compound comprising a benzine extractive from desiccated
parts of the plants known as Tephrosia, mixed with an emulsifying agent.

"In the manufacture of sheep dip such coiiound is mixed
with soan, sulphur, or other ingrredients and made into a
paste, powder, or liquid in any known manner. Likewise, in
the manufacture of an insecticide for use for the destruction
of plant pests, the compound a'orejaid may be mixed with soap,
sulphur, or other substances which serve -.s emulsifying or
carrying: agents and diluents.**** The Hdi, wash, or the like
may contain Lr- desired proportion of tho compound, according
to the class of service to which it is to be put. Or it may
be lot down or diluted before use. In practice, the mixture
employed will contain from 1-1/2 ounces of the compound to 100
gallons of water for thc destruction of small and delicate
insects up to 12 ounces of the compound to 100 gallons of water
for the destruction of the more h..rdy and vigorous vc.rioti js."

(over)









- 2 -


Grove, ia United Sttes Pateont ,45,485 issued ..y 15, 1923;
applied for July 26, 1922; claims a. medical compound for the treat-
mcnt of diabetes, including a liquid preparation of Tephrosia
virginiana and a lithia salt in solution, T. virginiana being in such
proportions as to cause it to reduce the sugar content and insipidity
of the urine and the lithia salt to activate as a solvent and
diaphoretic. ThEo preforrod formula is T. virgiiiana (ground roots),
9 ounces; lithii citrus, 1 ounce; powvdered cinnamon, 30 grAins;
cochincal, 3 grains; alcohol, 2 ounces; and water, 16 ounces. In pro-
paring this remedy the roots of th- herb T. vir'inia dried and
powdered, are boiled with 1 pint of water for about i hour. The de-
coction is then cooled and strained. The other ingrAdicnts are then
addcd, and the compound is allowed to sta..d for 2 days. It is then
filtered and bottled. The compound is to be takc internally, and
under ordinary circumstances a dose. i- 2 tcaspoonsful every 3 hours.
[From his rofrrcr-cos to the lit.-ratur, relating to the; medicinal
properties of this plait, which he calls goatsrue a.nd also Tephrosia
virginiana, it is probable that Grove confused T. virginiana with
Galc ,a offici-alis, as both are cormionly know-n -as goatsrue. R. C. R. ]






0-


of insecticid-os, sheep drips, .ini-h'.l cashcs a.nd vcrnifugces, and the like,
the use of a- org-ric salt r salts, compound or coinpoundi obtainedI front
the-plants, bushes, or trees know s -s tuba rabut, tuba! tcdon", Lcro (or
akar) tuba, ani p'rk-ka' as set forth. The pow-.dcrorC ba-rk, root, or other
portions of the plant arc extracted by a suitable solvent, such as benzinc,
the excess of solvent is evaporated, and the rTu.'ny residue is then nigcd
with the noccssary inCre(.ients for producing the required di p, w.ach, in-
secticide, or vcrmifui,.e, or it may be crystallized before suc, -. use. DIr-
imn; the :ianufacturo of the dip, a suitable water-sof-t.cnin; rcoo-.t or a
suit)able antiseptic, bactericide, or coloring matter .-aay be ad'''e'*. In
practice the U.i:tur,: e. -.oyd w11ill contain fror.i 1 ounce of the comcunI to
100 ipc'..al gallons of water for th.; destruction of s-icll an': Cd.licate
insect-s, u-p to 12 ounces of the c m .un to 100 iporia.l allows cf water
for the destrucUtio of tlhe :oro h r0.- aand vigorous catorpilla-rc. A ruit-
able "-,)aratus for the extraction is Coscribed. The extract "... be r:ixcd
with uulphur, soap, or othor in.redeionts iand nardo into a paste, poowver, or
liquid in any- -novn oainnr.

LIcDoucal, i.ccD u.:ali, an cu:'.all (65), in British patent 10,215 of
1911, issued Ma K., 1912, .ppliAe for April 27, 3-911, claix in the noanu-
facturc of nhcop dips, aii:al "..'ashs, vrius, and insecticides, the use
0UoS obtaine fr71"-"I
of an organic salt or salts, c-;'.pound, or ccmpoutds obtained from the plants,
bushes, or trees of the family _-nii otanicollvy as crris of the order of
Lcr_.i:.osac, as set forth. This invnti-on iis aarovc.-ct over that does-
cri-'ed in British patent 3,204 of 1911. The .cixtureo :. be us-ed for destroy-
ing oarth;onris and as a dosc for ani.ials for the destruction of internal
parasites. "As a dose the ixt-reo nay contain frn.: ,hbo-it 1/2 to 1 ounce of
the extract emilsifioed with then ..delc up t-) 20 ounces b- the ead-ition of sulp.h.r."!I

1cC.ug.all, McD:u-',ll, ,JiIcZ".>,:all (64), in British patent 8,322
of 1912, issued Dccc-.ber 19, 1912, appliedC for April 6, 1912, claim improved
infecticiLes, ihc"cp di, verdif es, and tihe like conprisia<:, in a powdLercd
or finely divided forn, the root, bark, or other portionis of the plants,
bushes, or trees of the Dalb. r-'ie tribe ond Doerrio family .an of porkakal,
fror. w--ich a: organic salt or salts, conpemd, or compoundss is c.xtractable
by moisture "r -;ator, suostantialIy as described. This invention is an in-
prove -.nt over that described in- the patentees' prior soccifi ca.tions--British
patents 3,204 of 1911 and 10,215 of 1911. The ground dcrris rmet nay i be
ni:xed ith soap, sulphuiar, or other substamnc.s.

Le.--.iens and Fryer (.54), in Britain patent 105,?5, issued April 19,
1917, applied for Decerbor 4, 1913, cl.on

"In the nai.:dfacture of insecticides, shop dips, .i .
washes and the li-ke, the use of an orraniic salt or salts, conpounICLd
or conpounCs obtained fro,: the sccc's, leave and other portions of
the plant of the species and varieties of the onus of plants known
as T:_,hrosia of tihe nrtur orc-or Lec tminosac and the mab-order
Paopiliona.coac, particularly the species of ToPhrosia known as
TC hr ci-. voLclii.






-4-


Ani ap.paratus for extractinK the powdreod dry plant iatcrial with
benzine is described. In -;ractice, the ni::turc employed will contain from
1-1/2 ounces of the con-ound to 100 imperial, -allons of .watcr for the
dc.tr..ction of small an. delicate insects up tc 12 ounces per 100 .-:allons
of water for the destruction of the nmoro hardy and vigorous varicties.

Ba,-:nall-Bull (4), in British patent 214,822, issued .May 1, 1924,
applicCd for April 16,1923, claims a :.cthod of obtaining : (-.orris extract
for use as an insecticide, v,.zr.ifue, sheep dcip, or the like, which con-
sists in breokinc or crushing the fresh roots or other portions of-the
plants of the fo-iily known botanically as Dorris or Tuba, treating thel
with water so as to obtain a milk en-alsion or suspension of the juices
contairiinL' toxic properties, aend then separating the cnulsificd substance
from tlhe whole or part of the water.

To soparato the a:-ulsific'. substance from the water, evaporate the
whole or a -:art, prcfcrably in vacuo, thereby obtainin<-g a paste of a con-
sistency s-aitable for transport, or a; "- to the .ilky emulsion milk of l.i:-c,
which zoa;,i-Lates or prccipitatos the. orulsified substance. Frcc the 1prccip-
itate obtained by- the last nothod front excess moisture by evaporation, by
filtration, or by ccntrifi;a"izing. Or nix it with tarta'ric acid. or any
other suitrablc acid in qu.ntity oquivlont to the uount -*f line contained.
in the -precipitate. Or the ilky oulsion ay be rnderc' kalL with
'.I a-ulio I a Ce rcec("lkrmli. Lc' with
soda carbonate, to which is thor. a'J.ed a brine or salt solution in a (ju-x.-
tity sufficient to salt out the c;.ulsifiod substance, which then precipi-
tates. Thr onulsifid subostan.ce or orecipitate so obtai:n3d is then dried
and eroun.d or can be used in a r.oist conditi-n according to the use to which
it is t. boe aEpplied. Crrii produces a '....r, which by reason of its
fineness admits of a suspension of the drug in w&ter. This preparation
.alone or aixed with inert powder may be used as a dustin; powder, or it may
be mixed with soap, sulphur, or other suitable substance for use as in-secti-
cidal washes, shop dips, or for spraying, either as a powe.or or when mixed
with water.

IIcDouzall and Howles (58), in British patent 226,250, issued Docc.-
bor 23, 1924, applied for June 23, 1923, claim a procots for the production
of ain insecticide, shce dip, verriift-c, or the like which is directly mis-
cible with water, by cr-ushing or pressing the root portion of plants, bushes,
or trees of the Dalbcritia tribe and Dorris f=xily to a Tulp, scouring the
fibrous rarticles by nochanical moans in the presence of water and :'i:,lly
separatin.; the fi`rois .:atrial,. from the rxgn, ..ubstnAti:aly as described.
The lato:< may be cv:poratcd in a vacuum at a low temperature. The active
material obtain.cd as before described, nay, if Idesired, b,. nixed with water
and/or soaps of various kinds, such a.s resin, fatty acid -r sulphonatcd oil
soaps, sulphur, antiseptics, water softening materials, spreaders, and the
like, for the .destruction of insect pests on ani-aols and/or plants or for
internal or external iar,'sites. The active ;;ror'ricnts :.a':-be separated
from the latex by precipitation with a basic salt of aluminum, iron, or load.
For ox.7i,]qp, to 100 cubic ccntinoetcrs of the latex, a quantity of concentrated
aluminum sulphate solution is added, so that the final dilution of the alm-
imum s-olphate in the latex is equivalent to 0.2 c'ercent. To. this is added
a solution of caustic soda. in qu.-'.tity insufficient to prccipitate th"c holc









of the .lE inrun sulphate a h-rdro: idc. T.. cocuiyt-u; is then trcatecd 'ith
an appropriate dilute acid to iroc it fro- Pctaliic sits, after which h it
is readily7 eo.ulsificd in wator and. soap.

":o'l,, ar.d YalC.in-, Ltd. and P. J. Fryer (69) ir British patent
229,773, issued March 2, 1925, apZlicd for Dcccnbcr 1, ?l claim insocti-
cidCs, sheenC diCps, animal ,rtashlcs andc th like, con-risin; an organic salt
or salts, compound or conpour-nds obtained front the root, bark "-r other por-
ti'ns of thc plants, bushes, or trccs of the Dalbi:r -iae tribc -aC Dcrris
faily and/or of pcrk'.* and s-J.plionatcd castor oil as a vehicle or rc-
in0 or activati- a-,ent for such organic salt or salts, cmpound, or compounds.

.D-. a., ane Ho-ics (60), in British patent 233,857, iss.cd HdMay 21,
1925, appliced for April 15, 1924, clain in insccticidccs, the combination
corisiif a mixture of n-cotinc "-ith the aforesaid C.crris extract or pow-
deorcd derris plant an, a neutral .iert bo, substantially as described.
An CzrpA of oreoar: this i.sectic. is: 2 prt., by weight of nicotine
are nixe.d rth 5 parts 0,- weight of pro.dere root and 933 parts of precipi-
tatedO caecianm c:rbonate. The extract nay be obtained by the process describocl
in prior specific.ati-n :T-s. 3,204 of 1911, 10,215 of 1911, andL 8,322 of 1912,
or in s)ocificati)n *,o. 226,250. This is used in owd.er form for dusting
hops and fruit trecs for the destructionn of a:phids, psylla, and various
c atcrp illars.

The Zaical Hojin Rikato. Kni-::yujo (102), in British patent 239,483,
issued L;:r 5, 1926, applied for April 24, 1925, in Japan, September 8, 1924,
clai::s a process of prep.rin<, a liquid insecticide' c-ntJnin the effective
n:reoi ent of the dlerris species, con:risim': the stop of "prep.rir. -. primary
re ient in which the effective in-redient is ixcd ith one or moro rils
an, or fats, wa:nes, resins, hi-her alcohols, higher hydrocarbons, higher
fatty .aciC.s (e :cludin;T Turke.o. red oil), 1 jhich arc entir(7ly freoc from watcr
and al"ali; and the stcp c-f rcparinr, a secornd.O.ry reag'ent in which the pri-
ano.r rc.,-cnt is nixcd as a colloidal solution, substantially as describedd.
3x~a.,.L os are:

"(I) A solution. of 10 litres of ether containing 10 ranrios
of rotcnollc is addcd to a mixture of 400 gran-cs of fish oil with
40 srizrzos of hydrouo-at.cd oil. After v-.fficicnt agitation, the
greater part of the other is recovered by evooration an. condon-
sation, and th,,rcby a semi-solid mixture is obtained as a primary
regent. Five hund'rcd :gra.ncs of so fS aPrc n:ixeod With 100 kilourvu-
moes of vator to prepare a, collridoal aqueous solution as a secondary
reagent. In use, the pri'nry reagent is mireC with the secondary
,re-gent and it may be suitably diluted with adfVition of 100 kilo-
grrunmos of watcr -Jhoi. used. as an insecticide. The secondary rcae;ont
nay be preparee, at any time by users.

"(2) Ten littersa of ether arc add-cd to 1 kilogra'zmc of the
dcrris root. After 4 days, the extract is added to 400 v.ro-.ios of
chrys-.lis oil and 100 gram-nos of lard. After evaporating the ether
a smcni-sol.id substance is obtained as a prinry r,-o'ent. The pro-





-6-


paration of the secondary reagent may be effected as for Example 1.

"(3) Twenty liters of petroleum ether are added to 1 kilogramme
of derris root. After 4 days, the extract is added to 200 grammes of bees-
wax and 50 grammes of pine resin. The larger portion of the petroleum
ether is recovered by evaporation and condensation and thereby a semi-
colloidal substance is obtained as the primary reagent. The secondary
reagent may be prepared by adding a colloidal solution in which 200 grammes
of soap are dissolved in 100 kilogrammes of water."

"It is to be understood that substances containing rotenone is intended
to mean any pure or impure substance obtained from raw root of the. derris
species, solutions of the substances in one or more solvents such as methyl
alcohol, absolute alcohol, ether, petroleum ether, chloroform, tetrachloride
of carbon, and extracts of root of derris with such solvents. The solvents
are recovered during the process. By oils it is intended to mean all kinds
of animal oils such as sardine oil, herring oil, cod liver oil, shark oil,
chrysalis oil and all kinds of vegetable oils such as cocoa-nut oil, been
oil, rapeseed oil, castor oil and the like excluding Turkey red oil. By
fats it is intended to mean all kinds of animal fats such as lard, beef
tallow, hydi'ogenised animal oil and hydrogenised vegetable oil. By waxes
it is intended to mean wood wax, beeswax and the like, while resins include
pine resin, copal end the like. By higher hydrocarbons paraffin end the
like is intended, while higher alcohol includes glycerine and the like.
These substances are selected as desired. Colloidal aqueous solution includes
a solution of soap, glue, eg;-albumin, bean milk, dextrine, starch, bengal
isinglass, animal albumin and the like. There may be added to said Pqueous
solutions a small quantity of methyl alcohol, ethyl alcohol, chloroform,
e3rher, camphor oil, lemon oil, and other solvents. Said additional sub-
stances may be added after they are dehydrated to the oils or fats used in
preparing the rotenon-containing reagent. Ordinary water can be also em-
ployed in place of a colloidal aqueous solution."

McDougall and Yalding Ltd. and P. J. Fryer (70), in British patent
246,252, issued January 28, 1926, applied for November 12, 1924, claim an
improvement in or modification of the invention claimed in specification
no. 229,773, according to which the sulphonated caster oil is replaced by
any other sulphonated fatty oil, sulphonated sperm oil or a sulphonated
wax. The most satisfactory results are obtained by extracting derris with
benzene or other suitable volatile solvent, and after the solvent has been
distilled off, by dissolving the residue by the aid of gentle heat in the
sulphonated oil or wax. The best proportion is 1 part of derris extract to
10 to 50 parts of the sulphonated oil or wax. This mixture may be used with
lead arsenate and Bordeaux mixture, but for use with lime-sulphur solution
it is necessary to add from 5 to 20 percent of casein to prevent precipita-
tion. Powdered casein may be dissolved in the sulphonated oil by gently
warming and stirring.

The Japanese firm Nettai Sangyo Kabushiki Kaisha (76), in British
patent 247,140, issued August 5, 1926, applied for June 25, 1925, in Japan
February 4, 1925, claims a process for obtaining ihsecticidal or other toxic
substances from plants of the Derris species in solid form, consisting in
collecting fresh juice of crushed fresh roots of the plants with the addi-
tion of water, evaporating the juice at a temperature .not exceeding 70 C.
and drying the same into a solid state, removing surplus resinous matters
from the juice-, substantially as described.






- 7 -


The; fresh root of tuba is crushed, and pf tor a sna.l quantity of
.'ater is added it is filtered. The filtrate is allowed, to settle for
about three hours in order to allow resinous matters tc separ'tte. The
supernatant material is then evaporated in a vacuum evaporatinL; pan or
an ordinary evaporator at a temperature net cxceoC.i:': 70 The contents
when pasty, arc spread on glass or iron -lates an- dried in a dryin
chamber at ". temperature of 40 to 450 until they beco.meio a deep-brown,
solid mass. The solid. mass nay be pulverized for conve.icnce of use.
The powdc'cd product is a light-brown powder which contains about 30 to
32 percent of rotenonc, 34 to 35 percent of dcrrid, and 35 percent of in-
p)uritics, such as resin, albuncn, -Lun, and ash. "Whcn-it is proocrl di-
luted by the addition of the odesiredo quantity of water, it bocones the best
insecticide for agricultural purposes."

SLTh. product is more effective than those containing the
sa-:e qtuantity of a sirylc kind of toxin, because, as is well-known,
the simultaneous use of two or more kinds of toxins is far nore
cffcctive than the use of the sanec quantity of any one of the.1"

.IcDou:-;ill and Yaldin'7 Ltd. rand P. J. Fryer (71), in British patent
280,256, issued IT-vc,-'jor 17, 1927, applied for ovcw;nbcr 24L, 1926, claii a
process for pro"'.ucir- concentratc-d complete and self-contained insecticides
containinf-; physiologically active, substantially water-insoluble plant ex-
tracts, extracted from plants nainly of the order Locufinosac (particularly
those containing' tubaC-toxin (rotenon) and or tephrosin) which consists in
dissolving; 'such extracts in a phenolic body or suitable solvent, adding,
the solution to a hydrocarbon oil or mixture of hyrlrocarbonr oils anic
finally cnulsifying the ".rholc, the emlsion -o produced nocessitatinf only
simple ac.iixturo with water in suitable --roportions to form a spraying so-
lution.

According to one ex1nple, 1 part of the resinous .ictivc priiLciple
from dorris or other source is, dissolved by -!.'.rmin. it with 2-1/2 ,parts of
comnnorcial crcsylic acid. Thiis is now added to 2. part of a suitable
hydrocarbon oil--for .xamnpile, modi-ur lubricating,--oil fraction of Anmerican
petrolou-i-anr' after the aCdition of 100 parts of a 10 percent ,:luc solution
thc whole is emulsified. According; to a second example, tho.solution of the
active principle in crcsylic acid, as .described in the first example, is
added to 288 parts of suitable hydrocarbon oil, and the -wholo is nixed with
12 parts of nruloniun cleate nr linoletc to for: a hono'-oncous solution,
which is diluted with water.

The Zaidani Hojin Rikoi.r 'L Kc-kyljo (108), in*British patent 285,797
issued ,l vcmbor 29, 1928, applied. for February 20, 1928, in Japan. February
18, 1927, claims a process for producin{- a liquidL insecticide containinGi
the effective in'-rcient of dorris species, which co:iprises fominrg a pri-
marr .riaterial in which the effective incrediont is rixcd with an anhyd.rous
Mand alkali free vehicle for the active inrc.,'ient, said vehicle consisting
of one or nore oils, fa.ts, wa:cs, resins, higher alcohols, hihor hydro-
carbons, hig hor fatty acids, to.:th,.r with a substantially equal quantity
of the a .-,rous "-I.vent, ber-.zol, carbon tetrachloride or trichlorothano,
which primary natorial is subsequently to be mixed with an aqueous soap so-
luti-n to for:- a colloidal solution.





- 8-


Exam- les are: (I) To 100 cr.!-s of powclered O.erris root, 10 liters
of other is acd.ec, and thereby the effective in-re.iont of the .crris root
is c;:tracted, the whole or creator part of the ether is evaporatec and
recovoroc. To the resicdual effective inf;rcCient a mixture of 150 grans
of anhiydrous and alkali-frooee fish oil (as a vehicle) and 150 Grans of benzol
(as the anhydrous solvent) is 6Odo&., So that a solution of the effective
ingredient is thus prepareC. This is the inprovod primary natcrial. The
soap solution is easily prepare':' by, for instance, adC.inL: 500 gram:s of soap
to 1.00 kilog;rass of 1watcr. The solution thus obtainoedl is nmixod with the
i::,rovcd primar- material in use.

(II) To 1 kilogran of powcerccd cderris root, 5 kilograms of benzol
is adcdeL anc! the effective ingredient of the cleorris root is extracter'.
while wamin,; the benzol. The benzol is recovered by evaporation. To the
residual. effective ingredlient, a mixture of 600 cramns of anhyrdrous and.
alkali-froe fish oil (as a vehicle) and 600 C:;racis of carbon totrachloride
(as an anhydcrous solvent) is aCd.ed so thut a solution of the effective in-
.redient is forneod. This is the in;rovod primary material. The soap so-
lution enploycld therewith nay be the sane as in the above nentionod oxamn-
pVio. Trichlor-ethane C2HmC13 as the ahydrous solvent cnm, also be used.
Also in the two examples Civen, the inproved- primary -aterial can be easily
prepared- in the form of powder whon 900 gramis of anhydirous cxsn arabic are
add-cCd.

The Zaican Hojin P.il-?;o- Kenkyujo (109), in British patent 300,606,
app.liedL for July 17, 1928, in Japan, Novenbcr 16,..1927, nadc essentially
the soc claims as in Australii--l patent 15327/28 (110).

The Stand-ard Oil Dcvelop;.cnt Co-:'p.rIny (95), in British patent 350,897,
issued Juno 15, 1931, applied for February 15, 1930, claims Man insecti-
cidal, insect-repellent, or funjicid-al composition conprisi'.-: petroleuw:m
whito oil, an extract of a plant havi.vn insecticidal properties and an emul-
sifyin.; a-geont. The insecticidal plant nay be a fish poison such as Dorris,
Lonchocarpus, or Tchrosia. Instead of, or together with tho fish poison
py rcthrum, nay be usecO. An exrnple is "T17o kilo,:ras of ";r-,Un' dorris roots
wnor crtractedl with four litres of boenzol. Distilling off the solvent in
vacue 113 Cram.s of dry extract were obtained :-c-_rcscntinc 5,65 percent of
the dry clcrris roots anL haviniV the appearance of a reddish brown rosin,
Eighty -rams of this extract were fed into a colloid mill with a solution
of 750 r-ray. of oil-soluble sodium sulphon..toe decrived- from petroleum. oil
in 2,5 litres of technically ,pur. .7hile oil. Water was also added in the
amount of 1.5 litres. A thick cnuelsion resulted- similar in a.pear.a-,cc to
mayonnaise and- reaCy for narkctin;g. Part of this preparation was dilutccd
with 50 times its weight of water and ,ave an effective insocticid-al spray
for horticultural purposes." Dcrris nay be extracted- Jith a volatile sol-
vent such as benzol or iso .ropyl alcohol or with white oil directly.
Volatile solvents such as alcohols, ethers, esters, ketones, .ro:E.-tic
hydrocarbons, etc., -ay ibe used to increase its solvent power. It is d.e-
siraCle to distil off subsequently most of the volatile solvent from the
product obtained-. Another class of solvents nay also be ad-(-IL to the 'while
oil before extraction, n--.cly, stca-i distilled- pine oil, terpincl, phenol,






- 9-


cresol, cyclohexano-. and its hoiologues, and hydrogenated or chlorinated
naphthalenes such as the ziaterial known under the trade name "halowax
oil". The ingredients just mentioned are not removed by subsequent distil-
lation. They Lro desirable in the prc.uct and confer upon it a fungicidel
and bactcricidal effect in addition to its insecticidal properties; they
also facilitate the emulsification.

Various craulsifying agents may be used such as, for instance, fatty
acid soap, rosin soap, oaponin, soaps of petroleum sulphonic acids, soaps
of sulphonatod vegetable or animal oils, etc. When the pla.t is extracted
directly with the white oil, .art of the soap used nay be added to the
white oil before the extraction since it has boor found that the presence
of a soap facilitates the extraction. ILi many cases it is preferred to
use the soap of ar- oil-solr.uble suiphonic acid derived from petroleum. Such
acids are obtained in the rcfining of the white oils. This spray is ef-
fective against various aohids, tent caterpillars, scle insects, red mite,
tomato moth, cabbr',.;, worn, sawflies, etc. The oxidizirng action of the air
on white oils and the d.volepYe:nt of acidity ray be inhibited by the addition
to the oil of smaol pcrcent js of some substcnce known generally under the
namo of anti-oyid-.tion catalyst. As exaznples, ?hc:iLL-throne and anthracene
nay bo mentioned, 0.5 ocrcont of which when added to the white oil prepar-
ation are sufficient to protect completely the latter against the oxidiz-
ing action of air. A .rcat variety of other oanti-oxidation catalysts nay
be used such as, for instance, diphenyl, toluidixie, which hvve an. oxida-
tion irlnhibiting action when precoent in c.::centration as low as 0.3 percent
of t.c oil. Other arnti-oxidation catalysts which -i.. be used arc alpha-
najphth)l, cainiphor, nitrcresol, : e._l.yd.rzine, f-uroin, etc. T 1-o anti-
oxidation catalysts are preferably added t- the white oil containing vege-
table insecticides principle before the enmulsification of the latter is
cried out.

GraaflanL and eollest.yn (30), in British patent 362,526, issued
Decombcr 10, 1931, applied for September 10, 1930. in Holland September
12, 1S29; claim an antifouling composition -g-aeinrt growth of and dmn'.-ge
by o:'ganisms in water comprisinI. a i ; ic binder and a poisonous sub-
stance other than one which acts upoi. iron to cause formation of salts of
iron, the coronsition beinp adapted to permanently retain its hydrophile
character. A suitable composition is Portland cement, 100 .:,.rts by -weight;
powder of blossoms of "hr.-:-unthenui cincrariaofolium, 5 30 parts by
weight; water, 110 parts by w1-^!ht. The Portland cement must be carefully
ni5c.'. with the powder of said blossoms. The rlixture is rendered plastic
b, the addition of a quantity of water, which plastic ;d-Lurc. is applic-
able in an easy manner, such a's for instance byi paintirL, with a brush, by
spraying, or the like. After hardening of the coatin- a p, rous layer has
beocn formed, in which, bcc,,s.s,, of i-.s hydrophilo character, the poison
rcrains effective and pr: vents the orarnisns from settling on or in it.
Another effective poison is for instance extract fro:. Derris elliptica.

The I. G. Farbcnindustrie, A. G. (39), in British patent 377,069,
issued July 21, 1932, applied for Novemrber 27, 1931, in Germany ITovc.Yber
27, 1930, clair.s a'prcp.'.ration for killing or eliminating files comprising





- 10 -


an insecticidal substance and a product obtained by subjecting petroleum
or a petroleum distillate to partial or complete hydrogenation so that
the odor of the non-hydrogenated material is removed. For example, 0.4
part by weight of derris extract (obtained by extracting the roots of
Derris elliptica Benth.) and 10 parts of diphenyl ether are dissolved
in porhydrogonated petroleum boiling between about 180 and 290 C.* and
the solution is utilized in the usual manner for killing flies, When
using extracts, as for instance extract of pyrethrum flowers, the said
hydrogoenatod products may be used as solvents for preparing those ox-
tracts.

The I. G. Farbonindustrio, A. G. (41), in British patent 378,300,
issued August 11, 1932, applied for December 12, 1931, in Germany De-
comber 13, 1930, :claims a prop-'.ration for killing or eliminating flies
comprising ,an insecticidal substance and a product obtained by partial
or complete hydrogenation of a mineral oil or a distillation product
thereof, except petroleum or a petroleum distillate, or a product of
the same kind consisting of a synthetic oil or a distillation product
thereof. Instead of using the hyc'rogenatod petroleum or petroleum dis-
tillates mentioned in British patent 377,069, favorable effects are ob-
tained by using the products obtainable by subjecting other oils to par-
tial or complete hydrogenation, so that the odor of the non-hydrogenated
material is removed. For the preparation of agents for killing flies
there nay, for instance, be used the hydrogenation products of mineral
oils (for instance lignite-tar oil, coal-tar oil or shale oil) or the hy-
drogonation products of distillation products thorcof, or there nay be
used synthetic oils of the sane kind obtained, for instance, by the hy-
drogenation of brown coal until the hndrogonation products are free from
unpleasant odor or there nay be used the distillation products of the oil s
obtained by such hydrogenation. There may advant.-:.'cously be used hydrog-
enrated oils of a specific gravity of about 0.75 to 0.85 at 20 0. and
boiling bctweocn about 100 C. and about 300 C.; such hydrogenated prod-
ucts may be obtained by hydrogenating, under raised pressure and tempor-
ature in the presence of a suitable hydrogenation catalyst, lignite-tar
oil, coal-tar oil, shale oil, solvent naphtha and similar oils.

The insecticidal substance nay be pyrethrum extract, derris ox-
tract or an ester or ethor of benzoic acid or a derivative or substitu-
tion product of this acid. For example 0.5 part of pyrethrun extract,
3.5 parts of 5-chloro-2-hydroxybenzoic acid awyl ester and 2 parts of
iso-bornyl acetate are dissolved in hyC.rogenratcc0 solvent naphtha. The
preparation completely 1-ills flies, culicidac, and similar insects.

The Standard Oil Dovelopnent Co., assignees of Sankmoskj- and
Fulton (96), in British patent 3?4,977, issued July 4, 1933, applied for
Jan-aar 4, 1932, in the United States January 5, 1931, claim an in-provod
insecticide comprising hydrocarbons rich in "unsaturated hydrocarbons"
-nd obtained by the extraction of a petroleum naphtha with a solvent
having a preferential solvent action for said "unsaturated hydrocarbons"
in adnixturo with ar insecticidal plant extract. The insecticidal plant







- 11 -


extract ma. be from pyrethrunm, cube, derris, or the like. Tests upon
houseflies showed that unsaturated hydrocarbons are more toxic than
saturated ones.

The Chemische Fabrik Marienfelde G.n.b.H. (14), in English
patent 432,626, issued July 30, 1935, applied for January 11, 1935, in
Germiany, January 18, 1934, claim "a process for the manufacture of dur-
able, highly concentrated derris root extracts which are emulsifiable with
water, characterized by adding weakly acid alkali resin soaps to a dorris
root extract obtained by means of, and containing, di- or trichloroethylene."1

An example of the process is as follows:

"Dorris roots arc exhaustively extracted with di- or trichloro-
ethylene, and the filtered solution is concentrated until it contains one
part of derris root extract in one part of di- or trichloroethylene. Resin
is saponified with caustic soda solution of 36 Be, only sufficient caustic
soda solution bein6 added for the soap formed to have a pH value of 5.0
or less. In this way, there is formed a weakly acid resin soap having a
water content of only about 20%. Fifty kilograms of this soap are dis-
solved in 50 kilograms of dichloroethylone, while being heated under a
reflux condenser, and the solution is mixed with 100 kg. of the derris
root extract concentrated to 1:1."11

Pyrcthrum extract may be similarly used. Di- and trichloroethZlcne
are better solvents for derris constituents than are alcohol, benzine,
carbontctr.chloride, etc.

Wikstron (102), in British patent 434,660, issued September 6, 1935,
applied for viarch 19, 1934, claims an insecticide comprising cyeneno cy.nol]
or a derivative thereof and the active constituents of pyrethrum or dcrris
or quassia or equivalent vermin-destroyin- agent of vegetable origin or
a combination of any two or more of said agents, the cynol or its deriva-
tive serving as a solvent or carrier for the said agent or agents. The
derris nay be extracted with cymene.

A further very valuable ingredient is chlorinated or sulphur=ted
ethereal oils. These oils act as contact (external) poison and as intern-
al poison and further have very powerful paralyzing effects, thereby facil-
itating the action of the poison or poisons present. Those products may
be prepared by treating an ethereal oil, such as oleum citronellae, oleum
eucalypti (for example the product known as "Globulus"), oleun codri,
preferably in heat and with stirring with aqua regia, chlorine water,
liquid chlorine, sulphuric acid, sulphur chloride, sulphides or poly-
sulphides such as the alkali sulphides. The product obtained is washed
with ,water, which nay be alkaline, and is then dissolved in cynene (or
some other suitable solvent).

A further valuable addition is a soap, preferably a resinous soap
and preferably a soap which is not completely saponified, so as to retain
a certain degree of stickiness and prevent the vermin from moving while







- 12 -


the poison is acting. It further serves as -.l attenuating gent and as
an cnulsifying agent.

It may also be of advantage to add a specific emulsifying agent,
for example, triethanolamc.ine.:

E:.:anples are: (1),. Derris-cynol extract (15 percent) 1 part,
Tricthanolanineo-,...1 part, water 100 parts. The trietheanolamine is first
dissolvecd in water and the dorris-cynol extract is then added with stir-
ring. The rest of the water is then..added. The preparation is facili-
tated if heat is used. (2). Pyrothrun-cy-nol extract (15 percent) 1 part,
dorris-cymol extract 1 part, water, 200 parts. (3). Pyrethrun-cy-iol ex-
tract (15 percent) 1 part, dcrris-cynol extract 1 part, quassia-cymol ex-
tract 1 part, water 300 parts. (4) Pyrethrun-cynol extract 15 percent
1-60 parts, derris-cy.mol extract or quassia-cynol extract 1-60 parts,
chlorinated or sulphurated ethereal oils 2-60 parts, soap 200-400 parts,
water 2,000-200,000 parts.

A convenient stock solution rv:- consist of: Pyrethrun-cynol ex-
tract (15 percent), dorris-cynol extract or quassia-cynol extract total
15 parts, chlorinated or sulphuratod ethereal oils, 6 parts, soap 79
parts. To this mixture is added, when it is to be used, enough water to
nakc a 0,25-15 percent solution. The liquid nay be sproaycd or sprinkled
on the plants or other objects which are to be treated, but dipping or
other ncthods of distributing the liquid nay also be cnployed.

The Booth Stcanship Co. Ltd. and H. G. Ward, (7), in British
patent 437,171, issued October 24, 1935, applied1 for March 30, 1935,
claiI:

The process for extracting toxins for the manufacture of insecti-
cides front roots containing rotcnono, according to which the roots in
crus'cd or ground forn are digested in conmon alcohol cacidLulatec by pure
sulphuric acid, andl the nixturc filtered so that the final filtrate con-
tains the rotenone and inciCdcntr.lly also other toxins of anl insecticidal
value present in the root.

The filtrate nmay be neutralize? with sodium carbonate and refil-
torod. The final filtrate nay be .nixed with soft soap so as to obtain a
senmi-solid product which can be diluted with water before use.

FaT.cett and Inpcrial Chemonical Industrios, Ltd. (26), in British
patent 446,576, issued April 29, 1936, applied for October 29, 1934;
clain1 a process for the production of rotcnono and/or preparations hav-
ing insecticidal value and containing rotenone, which comprises subjecting
the natural substances containing rotenone, to distillation at raised
tonperature in a high vacuum and. collecting the distillate. A vacuun of
between 10 and 10-6 mn. of mercury is used. The condensate front the
distillation nmay suitably be rmnovcc! front the condensing surface by nelt-
ing down, by scraping, or by rinsing with a solvent. An cxmonple of the process






- 13 -


is as follows: Fifty ports of dry --round de:rris root are mixed. with 100
parts of a linseed oil stand oil whichh has previously been treated in a
high vacuum at 2200 C. to remove volatile constituents. The mixtu-e of
derris root and oil is fed on to a heated surface or surfaces mlaint-.ined
at about 120 C. and in close proximity to a cold condensing surface, the
whole apparatus being evacuated to about 10-4 mums. of mercury. A pale
yellow condensate is obtained, giving the reactions of rotenone and con-
taining substantially all the active material present in the original root.

Other carrier liquids such as Apiezon, heavy mirciral oil, cotton-
seed oil, olive oil, etc., may be used. "When it is desired to obtain a
solution of the active ingredients as distillate, the dry powdered dorris
or cube root ma', be mixed with a carrier liquid which is either wholly
distillable at the temperatures and pressures employed, or comprises a
portion so distillable. Thus a mixture of the oils known respccti-cly
under the trade names 'Apiezon A' and 'Apiezon K' nay be used. The active
ingredients distil over together with the 'Apiezon A' leaving behind a
suspension or solution of the residue in the 'Aopiezon K'. The distillate,
which is a more or loss concentrated solution of the rotenone etc. in
'Apiezoh At (the concentration can bo varied by varying the proportion of
'Apiezon A' taken), is suitable for dilution with kerosene or other vol-
atile mineral oil for use as insecticidal spray."


Canadian patents.

McDougall and Howlos (61), in Canadian patent 247,627, issued
March 17, 1925, applied for !lay 22, 1924, make the sae- claims as in
British patent 226,250.

McDougall and Yalding Ltd., assigned of P. J. 7rvcr (67), in
Canadian patent 253,319, issued Septnember 1, 1925, -pplicd for 1**vombcr
26, 1924, claim a process for the production of insecticides, sheep
dips, animal washes, and the like which consists in mixing or incolrpor-
ating with an organic salt or salts, coifjoLa.nd or compounds obt-ined front
the root, bark, or other portions of the plants, bushes, or trees of the
Dalbergiac tribe and Derris family and/or of perkakal, a sulphonated fat-
ty oil, sulphonatod sperm oil, or a sulphonatec wax as a vehicle or sprcad-
ing or activating agent for such or."inic salt or salts, comnpoundc or con-
pounds, The sulphonatcd fatty oil nay be sulphonatcd castor oil.

Dennis (19), in Cana.di'. patent 293,233, issued September 24,
1929, a.pplicrd for March 12, 1929, nakes essentially the ::ano claims for
ground cube root with the fibrous elonement removed and for an extract of
cube root as he previously made it in his United States patents.

The Standard Oil Develop:ient Comp-oany, assignee of Grant (31), in
Canadian Patent 333,642, issued June 27, 1953, apnlie1. for October 25,
1929, ,2kes the followin,- claims:






-14-


"A spray for sensitive foliage com -risinrg a derris ex-
tract incorporated in .7hi.tQ. .oil. A composition of matter corn-
prisirng an aqueous amulsion of -white '.oil containing an organic
solvent extract of derris. -A-,.pray compriE.-ing a concentrated
aqueous emulsion of white oil containing rotenone diluted with
about 50 to -100' times- .its volur:e 'of water.'I

The Standard Oil' Cormrpaihr, assign.ee of Adams (1), in Canadian
patent 3.38,896, iscu-d January 23,,1-934, applied for October 23,' 1931,
elaiis a mothproofing composition cori-ricing a chlorln:ated hydrocarbon
extract of cube. It also claims a mothproofing composition which com-
prises a chlorinated hydrocarbon extract of cube dissolved in petrol-
eum naphtha having a boiling range of about 450-550 F.

The Standard Oil Company, assignee 'of 7. J. McGill (73), in
~Cna-i patent 338,897, issued January 23, 1934, applied for April 1,
1932, claims a mothproofinr solution containing an extract of derris.
ClaLi is also made for a solution of the active principle of haiari in
petroleum naphtha boiling ,betw7ecn 450-550 3F.

The Standard Oil Devclopmcnt Co., assigned of Sankbwsky and
Fulton (87), in Canadian, patent 340,315, issued March 20, 1934, applied
for December 24, 1931, in the United States January 5, 1931, claim an
improved insecticide, comprising hydrocarbons, rich in unsaturated hydro-
carbon..s and obtained by the extraction of a petroleum naphtha with a
solvent having a preferential solvent action for said.unsaturated hydro-
carbons, and containing the extractives of,at least one of the plants
selected from the grouip'conisisting of pyrethrum, cube, daorris, and the
1 ike.

The International Hydrogenation Patents Coupa:.y, Ltd.,. Vaduz,
Liechtenstoin, assignee of Pfaff and Dhinkel (81), in Canadian patent
345,383, issued October 16, 1934, applied for December 12, 1931, in
Genrmany Decomber 13, 1930, claim an insecticidal composition, comnpris-
ing a solution of mn insecticidal plant extract a:-d/or a compound of
the group co:.prising esters and ethers of benzoic acid and substitution
products thereof in a hydrogcn:tcd mii-cral oil boiling between about
100" C., and 300 C. and having a specific gravity of about 0.75-0.85
at 20 C.

Schotte and GCrnitz (88), in Canadi-n patent 348,379, issued
February 26, 1,935, applied for J?nu-:.r' 24, 1934, claim -n insecticidal
preparation consisting of a mixture containing extracts of !rugs con-
taining rotonon and voratrin. They also claim an insecticidal prepar-
ation consisting of a mixture containing radix -c.rridis elliptical and
semcn srLbadiill,-lo.

Schotto and G4'rnitz (89), in Canadian patent 348,380, issued
Febru.r:' 26, 1935, applied for Januir:- 24, 1934, claim a soliified
finely distributed mixture of a molten carrier and finely distributed
lerris root. PomTl.crcd tobacco or pyrcthrun may bo used in place of
the derris,




- 15 -


The Kessler Chemical C-rp.,' assignee of S. G.o1dschmidt and K.
Martin (29), in Canadian patent 357,959, issued May 19, 1936, applied
for December 17, 1934,'in Crmany D cember 27, 1933, claim as a toxic
agent and more particularly an .Insecticide, a pr:pnration corprising
as an active constituent an aromatic insothiocypnate in which the
isothiocyanate radical is directly attached.,,to the aromatic nucleus,
in mixture with another insecticide such as nicotine, derris extract,
or rotenone, respectively.

Ward (101), in Canadian patent 362,903, issued December 22, 1936,
applied for August 29, 1935, in Er.nglnd, March 30, 1935, makes essen-
tially the same claims as in British patent 437,171 issued October 24,
1935, and in United States patent 2,056,438 issued October 6, 1936.

The Shell Development Company (92), assignee of W. J. Yates,
in Canadpian patent 369,390 issued October 19, .1937, apli-ed for December
24, 1:936&, in the United States January 6, 1936, claims an insecticidal
composition comprising a stable mineral oil distillate,, an oil-soluble
vegetable insecticide selected from the class consisting of rotenone and
active ingredients of pyrethrum, end a small proportion of a substituted
aryl compoi-nd in which at least one hydrogen ator of the aromatic nucleus
is replaced by a rcleobcr of the group consisting of amino, hi.dr-'Ayl, and
alkyl radicals. Dihydroxy and dialkyl r.ono-hydroxy aromatic compounds
are also included among the substituted aryl coi.ipounds.

Imperial Chemicals Industries Otd. (46), assignee of Fv.''ett,
in Canadian patent 369,499,, issued Oct. 26, 1937, applied for Oct.. 28,
1935, claims the process for the production of rotenone preparations
,which comprises subjecting a natural rotenone-cont-ining' substance to
distillation without ebullition at a pressure of 10-2 to 10-6 mms. of
mercury under such conditions that the evaporating end- condensing surfaces
are substantially co-extensive end are in close proximity to one another,
and collecting the distillate. The material may be dried and ground and
mixed with a carrier liquid which is substantially volatile at the temper-
ature and pressure to be employed This is similar to British patent
446,576; French patent 797,052 and United States patent 2,096,678.


Dutch patents.

The Japanese firm Nettai Sangyp Kabushiki Kaisha (77), in Dutch
patent 21,841, issued May 15, 1930, applied for February 10, 1926, claims
an insecticide whose activity is due to the active principle of derris
root, obtained by extraction with an organic solvent, and made by mixing
the extract with one or more kinds of oils, fats, waxes, resins, higher
alcohols, higher hydrocarbons, higher fatty acids (not including sulphon-
ated oils or fatty acids) which are absolutely free from water or
alkali. Examples are: (1) A solution of 10 grams of rotenone in 10
liters of ether is mixed with about 400 grams of fish oil and 40 grams of
hard oil. After complete mixing a large part of the ether is recovered
by evaporation and condensation. The volume is reduced to about one-half.
Before using, 500 grams of soap are dissolved in 100 kilograms of water
and into this is mixed the reduced portion above. Finally, the mixture can





t


16 -


bc (diluted with 100 kilogr.s water, (2) to i kilogram d of cerris root
is aCcd_ 10 liters of other After four days 400 grains of chrysalis oil
andcl 100 graous of hog siet 4c ailddcd to _thec extract. The ether is evapor-
ated leaving about one-half the original volume. From here on proceed
as in E:Naple No. 1. (3) One kilogr.in of dprris root is soakc'. with 20
liters of petrolom- ether. After 4 days 200 grams of bcoswax and 50
grans of pine resin are added to the cxtract.,- After this has dissolved
as such as possible, the greater part of the pct'oleun ether is rcc':vcrod
by evaporation and co -densation, leaving a senicolloidal mass. -This resi-
due can be dispensed as a colloid in a solution of 200 grams of soap in
100 kilograms of water,

Rotenone decomposes on long contact with water or with alcohol
containing water. Further, the active principle is unstable in the
presence of alkalies.

Suitable solvents for the extraction of dorris are methyl alcohol,
ethyl alcohol, ether, petroleum ether, chloroform, carbon tetrachloride,
etc. As oils the following{ nsay be used: all sorts of animal oils, such
as sardine oil, herring oil, cod liver oil, shark oil, chrysalis oil,
as well as all kinds of vegetable oil such as oil of coconut, bean (soya),
rape seed or linseedoo! oil, etc. As regards fats, all sorts of anirial fats
na- be used such as ("'.-) suet, beef tallow, as well as hardened plant
oils. As waxes, nay be used 'the following: Beeswax, wood wax, etc. As
resins, pine rosins, copal, etc.. Suitable higher hydrocarbons nay be
paraffin or similar compounds, higher alcohols, such as glycerine, "etc.,
the ones chosen depending on circumstances.

As emulsifying agents the following nay be used; aqueous solutions
of soap, glue, ej: white, milk of soya bean, dextrin, starch, Bengal fish
glue, animal protein, etc. Sometimes to the aqueous solutions are added
a saoll quantity ethyl alcohol, chloroform, ether, oil of camphor, citron
oil, or other solvents.


Fronch Patents:

McDougall and Yalding Ltd. (68), in French patent 589,506, issued
MI, 30, 1925, applied for iTov;mbor 22, 1924, in England Decemnber 1, 1923,
make essentially the same claims as in British patents 229,773 and 246,
252. A sulphonatcd wax or a sulohonated fatty oil (castor or sperm) nay
be used as the spreading agent with dcrris extract.

McDougall and Houles (62), in French patent 589,969, issued June
9, 1925, applied for H.ay 14, 1924, in England Junec 23 and Novcnbcr 22,
1D23, make the sane claims as in British patent 226,250.

Dupre and Conp-any (23), in French patent 769,i45 published August
25, 1934; applied for February 28, 1934, clain an ir.insecticide consisting
of quassia extract, cgotablQ oil and rotenono (or extract of dcrris or of
cube), plus sassafras oil. This is s.ade by nixing 10 kilograms of quassia






- 17


extract (25%) plus about 4 kilog.rans of triethanolanino 'ith 50 kilo-
crars of vegeotable oil (c.g.huile do arachidc) plus 11 k1. oleic acid
plus 1 k;. rotnonon plus 100 grans sassafras oil. For us' the mixture
is diluted with from 100 to 150 tines its weight of water.

The J. D. Riod.el-. Do Hacn A.-G. (82), in French patent 773,844
issued March 25, 17,35, applied for September 24, 1934, in Gcrmany Sep-
tember 30 and Tovcnboer 5, 1933, claim a process in which extracts of
plant insecticides (e. g. extracts of Crys:nth cnu__ cinerariaofoliu ." oand
of varieties of Dcrris) arc atomized by air mnder pressure to destroy
insects. Aqueous erulsions of these extracts nay be used.

The Booth Steoanship Co., Ltd., and H. G. 7ar< (8), in French
patent 794,206, issued Fobruary 11, 19,'36, applied for August 27, 1935,
in England, L.':rch 30, 1935, make the sine claims as in British patent
437,171.

The -Inmperial Che-. cal Industrie-s Ltd. (44), in French patent
797,052, issued Aoril 20, 1936, applied for October 29, 1935, in Eng-
land October 29, 1934, nakcc the sa.cm claims as in British patent 446,576.


Geraanr Patents:

Lci-ic,'s and Fry-'cer (55), in Gorman patent 321,317, issued cI'./ 29,
1920, applied for Decomber 21, 1916, mal-c essentially the sae claims as
inUnitcd States patent 1,242I,5.

Lomne.-icns anO Fryer (56), in Ger-:an- p-tcnt 327,583, issued October 11,
1920, applied for December 22, 1916, namkc essentially the saine claims as
in Unitcd States patent 1,2.2,454.

The I. C-. Farbenindustrie, A. G. (40), in German patent 555,117,
issued July 18, 1932, applied for Novoember 28, 1 70:, claims a fly spray
:ladoe by dissolvingi a fly destroyii,,; materiel such as aniyl salicylatc,
ph.-nyl salicylato, pyrcthrun extract, or dorris extr--act in a partially
or wholly hydroogenated potroloum or pctroloi-1 distillation products. For
example, 0.4 part dorris extract (from roots of Dorris elliptica)> and 10
parts di-phonyl othor rC dissolveod in pc'rh:-rogcnatecd petroleumz.

Steindorff, Pfaff, Kra-.cr, and Korn (97), assignors to ti*c I. G.
Farbcrinc.strio A.-.G., in Gern.n patent 564,018, issued :Tovc:bcr 12, 1932,
applied for July 5, 1931, claim a product for conbatin": flies and. sinilar
insects consisting ; of urethanes or their substitution products together
with extracts from ,oyrrhr- or dorri: root, or synthetic insecticides.

ich.rn (24,), in Gornan patent 630,483, issued 28, 1936, ap-
plied for November 22, 1932, claims the process of tnanufacturinC an in-
secticide rontaining dcerris extract which consists in extracting finely
divided derris ro-,t with a dilute solution of sodium bisulphite at 40
to 500 C., a2utr-.lizin., the solution r.a. concntrating, in.vacuo.






- 18 -


E;m .. lples are:

(1) 100 parts -rour.1 or shredded dcrris root -.nd 100 parts of a
10 percent socl-,-i bisulphito solution are ground 3 to 4 hours in a hill
at 40 to 50 C. The solution is filtered, neutralized and evaporat&eL
in vacuo.

(2) 100 parts fcerris root arc ettractec in a pcrcol.,tor with 200
parts of a 10 percent sod.iun bisulphitc solution, with recirculation, anc.
the extract treate'l as in Ex:anplc 1.

(3) The extraction of the dorris root is carried out in a diffus-
ion battery.

The tract 'btainOd I'rorn d(orris by extraction -with water amounts
to 6 percent of the woiL;ht of the root and contains 4.29 percent rotenone,
whereas the extract obtained .vith sodium bisulphite Lmounts to 1Q percent
of the woight of the root ane. contains 16.95 percent rotcnono.

Tests on insects c;avo the followiinr results:


Test animal Result
dcad. dtunnc(
_________________________________________Percent Perccrnt


1. Derris powmcr*%with jater as
paste (10:50)

2. Aqueous extract of derris
root (1:50)

3. Soclium bisulfite extract of
dorris root (1:50)

4. Aqueous extract of dorris
root (1:50)

5. Socliun bisulfito extract
of dorris root (1:50)

6. Aqueous extract of derris
r*)t (1:50)
7. Srclium bisulfite extract
of dorris root (1:50)

* contained 2 percent rotcn'-nc.


Cockriachcs



it



Japanesc green-
house locusts


Mole crickets


50


100


40


20


100

Stunned after 25 rin.
dcaC. after 60 nin.

Stunnccl after 17 nin.
dead after 23 nin.






- 19 -


Chro:oe: (15), in Gernan patent 64!,804, issued Aoril 17, 1937, ap-
plied for February 7, 1932, claims an insecticide consisting of an o:-
tract of o, rotcnono-boarinr root in aliphatic .-d:','carbons, especially
petrolcin, hoxachioroe thane, a-r-voniu'o linolcate, and n .mator. An cxO2iplc
is derris pooicr 7 parts, hexachlorecthane 12 p)arts, a"-noniun linolcateo
4 parts, petroleum 25 parts, nmethyl salicy-latc 2 parts, ?anO 7atcr 50


The Booth Stca.-.hip Ch Ltd. anC T- .rd (s), in Gernan patent 646,570,
issucK! June 17, 1937, ap)lic' for Scptc:ber 11, 1335, in Great Britain
...arch 30, 1935, csscntially' the sonc clai -x as in 3-ritish p'.tent
437,171 and- Unitdc States patent 2,056,4:5e.


Jaane:.se Patents:

liba and ih-2:atura (-12), in JOanesc patent 1,-78 issued Hay 20,
1931, clain a -n;ture of 67.6 percent tric.'lcr')cthan ando 32.4 percent
nethyl alcohol (the :.ini:nv- boiling r:ixitrro) for 'aso as a solvent in ex-
tractian. -p)yrcthrun flo.orers or d.crris root. The sr lvont is distilled a(
the rosid-uc used as arn insecticicc.

Inai (43), in Japanese p .tent S ,645, issucO June 3, 1931, p.atuenteC
an insccticid.c consisting of vc,_'cbta'le vol'.tilc oils (such as turpentine
or cr-aphor oils-), naphta" lcne, and extratcts of erris ots.

Isihara (417), in Ja.pa-cnese p'.tent 91,375, issued s. June 20, 1931, paten-
ted' a process in whichh dried roots of pints bclon;im" to the. dcrris froup
are cut into pieces and mo;dorcd under co'ol1in- L a sp.cil. stnpin:
-achino. I por/dor passed throu<'h a )- ::osh sieve is used. as an insecti-
cide,


Jc,._ro Patent:

-. report fro.i 3ochriv'or (3) iJ-nsc Firn Clai-is T-Ti Process of Ob-
tainin-: Toxic Substance froa Dorris], As-istont Tra.c Comissionor, SinC;.a-
pore, dLatcd '1. .-rch 8, 1934, stated c that thc icttai San;yo Kabushiki Kaisha
of To .m"o, Japa., hias boccn rantcd the exclusive privil ,;c of rooking, sell-
inf; and using in the State of Johorc, an invention for "A nc' or improvc-
process of obtainincr inscctici,.al or other toxic substances fro:i plants
of the dcrris sp)ecics." This Drivillo-co is for the torn of 16 ;:cars from
June 19, 1i2,11.


Svc7O sh Patents:

ikstro'. (103), in Swed.ish patent 86,C-J3, issued April 15, 1936, ap-
plied for 1Harch 16, 1934",' claims ,s an insecticiLde cyn. [cy-icnc] or its
derivatives. Dissnlveo or sUspended- in cynol na, b pyrtru, rris,
qu .assi a, rotrcnonc, ctc.











- 22 -


wash, or insecticide, a suitable water-softening reagent or reagents nay
be added to the composition. In like :annor .a suitable antiseptic or bac-
tericide and also a coloring matter nay be added.

Dew an! Halo (22), assignors to the Dow Cho-iic:ril Co., in United
States patent 1,514,377, i.-sucd NTovcnbcr 4, 1924, 2nniied for March 31,
1920, claim an insecticide consisting of uthe halohyerin extract of derris
aciixcd with benzyl alcohol. They also clain an insecticide comprising a
solution of benzyl alcohol and a halchydrin, the amount of the latter bo-
ing sufficient to render such alcohol freely soluble in water. Ethylene
chlorohydrin or propylene chlorohydrin are suitable halchydrins. The
preferred proportions are 1 part alcohol to 1 part chlorohydrin.

"We have also found that the combination of ingredients
just described serves as an excellent solvent for various so-
called deadly insecticides, such as timboin, nicotine vnd dorris
(or "Fish poison"). In- utilizing such combination of ingredients
in this connection, wo preferably extract the poison first with
the halohydrin, and admix the extract with benz-yl alcohol in
desired proportionsi, depondinc upon specific use to be nade of
insecticide. Furthormoro, such combination of ingredients nay
readily be nixed with inert dry .-:trcrials, such as line, lead,
calcium or magnesium arsc:natc, .,n.l the like, capable of absorb-
ing the sane, and. can then be applied in the form of a powder
or dust, with highly satisfactory results."


Bagnall-Bull (5), in United States patent 1,522,041, issued Jan-
uary 6, 1925, applied for July 22, 1924, sak the sano claims as in
British patent 214,822.
Fryer (27), assignor to McDougall and Yaldiin, Ltd., in United
States patent 1,583,681, issued May 4, 1926, applied for Novembcr 29,
1924, claims an insecticide conprisin4 derris, a vehicle of a sulphonated
fatty body, and a colloidal addition agent. The preferred insecticide
consists of 1 part of derris extract to 10 to 50 parts of sulphontcW. oil
or wax, for example, sulphonatcd castor oil. If it is desired' to use this
material in combination with line-sulphur so as to produce a conbinecdi in-
secticide and fungicide, precipitation of the nmatorial nay be ,rcvcnted
by the addition of a colloidal agent, of which casein (5 to 20 percent) is
found nost suitable. Powdcrc.- casein ;:ao' be dissolved in warn sulphonated
oil,

The active principles of derris are extracted with bcnz~ne or
other suitable volatile solvent. An extract of pcrkakal nay be similarly
used. The sulphonated oil nmy be sulphonatecd sperm oil. This insecticide
nay be used alone or in admixture with lead arsenate and bordcarnux mixture.

Dennis (17), on April 16, 1923 filed application for United States
patent 1,-21,240, which was granted him on !Larch 15, 1927. This patent
covers the use as an insecticide and vcrnifugc "f --r)und cube root with






- 23 -


the fibrous elemenr-t removed. Cube is stated to be a woody shruo found
in Peru and other South American countries ihich is classified by so.0
native botanists as of the family Solanaceac. Directions arc given for
preparing a. solid e:tract of cube by grinding the roots or plants, ex-
tracting4 with a suitable solvent such as benzol, or alcohol, filtering,
and *v-..-orating. The solid extract has a light stra':. color and is odor-
loss a:LL tastel-S.-,

"Fo)r identification, the pouder may be subjected to the
action of concentrated su]phuric acid and dilute nitric acid, vrhere-
upon it gives a bright clear reo, color. By the addition of po-
tassiumi hy'r::idc inr nearly equal vol-xme, a vi,,orous action is
obtained, and the, solution turns to a yelloni sh .pirnk. A further
addition. of ptassiun hydroxido produces a stable brolnl solution.

"ThI co- .ponuL.n the form -f- povTor or dubt -ry be used as
ar. insecticide lith ta.cu-: powder, corn. .:, rch or nthcr carrier.
It is very effective _rai'st fliis, roaches, a:-i other insects.
It is my belief that the po7ier sots up arn irritation of the
broat-i:-.c apparatus which reslIts in early d&ath.

"The compoui(l cnr-. be used with water or vith soap and -ater
or other omulsif:ine .?_on-t, :.s a 7-ash or spray for plants, ninals,
or trees. It is effective a.;ainst aphids, beetles, some insects,
,and woris.

"It can bo used as an extract *vith alcohol for similar 1pur-
poses, for instance as a i:ash for ticks or. cattle.

"As an alcoholic e-tract, tests sholv the solution to have
sli-:htly ,*'rcatcr effectiveness vhen sprayed on the cotton aphid.
than nicotine cz-iphate. n-:icricncc shows that it is ei.?ht tines
as effective as similar dorris extract.

"TnE proportions of the compound a~d the carrier may bo
varied as Cdesirodl for different purposes.

"For certain p-irposes, it is dosirablo to use the alcoholic
extract in a soap and -water cnulsification. A suitable solution
for o.phids c,.I be :adec byu using the extract fr r. one-third pound
of po.,rdcr in onc hundred a.UIons of soap solution."

In a reissue of this patent (reissue 18,6C7 f or 22, 132,
applied for F..br,,u.r- 25, 1929) Dennis (18) corrected. the information con-
corning the bota,.ical origin of cube -ivc:_ in his original pA.tcnt 1,521,
240, statia:-- "Th.lc the exact botanical clZu'--iiication of the plant is
not alto[ethor certain it is believed to be a species ")f the genus Loncho-
carpus of the family Le-:uninosae."

Takei (98), assignor to Zaidan Hojin Rikcmuiu Kenkyojo, ir United
States patent l,724,f26, issued Aurust 13, 1929, applieC. for AWuust 31,






24 -


1925, in Japan, Scptcnber 8,.1924, claims the process of producing a
liquid insecticides containing the offective-ingredient of the derris specie
which comprises oxtracting raff nateorial containing the aforesaid ingrcz'-
iont with a volatile ofjianic solvent therefore, nixing the extract with an
anhydrous alkali-free organic preservative for the inrient, varating
the solvent fro"k the ni::tuie and nixing the recsiting product with an or-
ganic colloidal natori.al in an aqu-eous neodluni. Exanples arc: (1) A so-
lution of 10 liters of ether added. to 10 grams of rotenonc, is :.ixcd with.
a mixture of 400 grains of fish oil with 40 .grzvi of hard oil. After suf-
ficient agitation, all or the greater part of the ether is rt.cmvcrcd by
evaporation and condensation and thereby a sonmi-solid mixture is obtain.
as a primary material. Five hundred lrams of soap arc nixod with 100 kilo-
gro;ns of water to prepare a colloi:1al aqueous solution as a secondary nater-
ial. In use, thc primary rca.;ent is .-ixc,'. with the colloidlal aqueous solu-
tion andm it nay be suitably diluted with addition of 100 kilograms of water
when used as insecticide. The colloidal solution or secondary reagent nay
.be -prcpared at any time by the users. (2) "cn liters of other are addOd.
to 1 kilo-gr,.-: of the dorris root. After 4 dcays, the extract is added to
400 crmas of chr;'-,?J.is oil and 100 ;ra;n-s of lard. After cva,oratin- the
ether, a soni-solid substance is obt"anecd as a primary rca-ent. The prepar-
ation of tIhe seconda:ry remoent is sne to t'.:at of oxanple o. .(3) Twienty
liters of petroleum cther arc added t.-) 1 kilogram of derris root. After 4
days, the extract is added, to 200 g:'.-; of beeswax and! 50 granvs of pine
resin. After solution, the lar:cr portion of the petroleum ether is re-
covered! by evaporation anm. con-Zonsation and thorcby the soni-colloidal
material is obtain' as the primary material or reagent. The secondary
reagent may be prepared by adding a colloidal solution in which 200 grams
of soap are dissolved in 100 kilograms of water.

Takei attrio-..tes the poor qualities of rotenone insecticides on the
market to the combined action of alkali and water. A superior product is
nade by nixin<; rotenone with one or more kin(s of oils, fats, waxes, resins,
higher hydrocarbons, hiphcr alcohols, higher fatty-acids which are entirely
free from water and alki-li to form a stable preservative mixture and this
mixture is mixed with colloidal -LiucouS solution such as soar. water in use.

Rotonone *--ay be cxtra-tc- with such solvents as nethyl alcohol,
ethyl alcohol, other, petroleum ether, chl].oroform, or carbon tetracLloride.
The oils --ican all kinds of anmi'inal oils, such as sardine oil, herring oil,
cod-liver oil, shark oil, chrysalis oil, or a vegetable oil, such as coconut
oil, bean Qil, raposeod oil, and castor oil. Thc fatty oil ra.y be a natcr-
ial such as la.rd, beef tallow, aninal hard oil, and vegetable hard oil.
Waxes, such as wood wax, and beeswa.x may be used, also resins, such as pine
rcsin, and copal. Higher alcohol includes glyc--rin, and higher hydrocarbon
no ans paraffin, etc.

Colloidal aqueous solution includes solution of soap, glue, i;g-
albuiin, bean milk, do-:trino, starch, bongal isinglass, animal albuiAn-, etc.
Sometiies to said aqueous solution is added little quantity of ricthyl al-
cohol, c'thyl alcohol, chloroform, ether, caiphor oil, lc::on oil, .ncl other
solvents.






- 25 -


Ohori andLd ,l'.:a.:,a (78), assignors to Zaidan Hojin Rikagac-u Kenkyujo,
in United States patent 1,745,907, issued Februar, 4, 1930, apiNlicd( for
February 10, 1928, in Ja-nn, February 18, 1927, claim a process for pro-
ducing a liquid insecticide containing the effective ingredient of dorris
species, ;vhich comprises forming a primary natcrial in which the effective
ingredient is mixed with an anhydrous 2nd alkali-free material of an oily
nature and dissolved in an anhydrous solvent such as benzol, carbon tetra-
chlorido, or trichlorocthane, and then mixing the primary material with a
soap solution to form a colloidal solution. Examples are: (1) To 100
gr,.is of pod-.7ered dorris root, 10 liters of ether are added to extract the
effective ingredient of the erris root. After extraction is complete, the
ihole or greater part of the other is evaporated. and recovered. To the
residual effective in Tredient a mixture of 150 grans of ainhydrous and al-
kali-froee fish oil and 150 grras of benzol (as the anhydrous solvent) are
added, so that a solution of the effective ingredient in benzol results.
This is the improved primary material. The soap solution is easily pro-
piared. by, for instance, addim; 500 gra7s of soap to 100 kilogram-s of water.
The soap solution is nixed w-ith the in-proved primary material before use.
(2) To 1 kilogram of powdered dXerris root, 5 kilo -:-ans of benzol are ad-
dod and the effective ingredient )f the dcrris root is extracted while
airingg the benzol. The benzoL is recovered. evaporation, To the rosi-
dual effective ingredient, a ni::ture of 600 grams of aMh.y.'rr.us and alkali-
free fish oil andd 600 .-.rar of carbon tetrachloride (as the anhydrous sol-
vent) are added to form a solution of the effective ingredient. This is
the improved primary material. T.he .oap solution nay be the same :s exemn-
plified in E-.armle I. Trichloroethanc as the anhydrous solvent can be
used as well. Also in the two ex-i-ples given, the inprovod primary material
ca-n be easily prepared in the form of powder -when 800 grams of anhydrous
gun arabic are added..

O'Kane (79), in United States patent 1,786,125, issued December 23,
1930, applied for ..:Ma;- 18, 1927, claims a fungicide and insecticide con-
sisting of a hydrocarbon white oil emulsion carrying a colloidal copper
containing material. If desired this refined oil" may be used to extract
any suitable organic material such as pyrethrum of various species, dorris
of various species, or other substances that will furnish an additional
kill in-: agent effective ,-gainst insects. Or, such materials may be added
to the refined oil. Th.: colloidal metal derivative may be, for example,
colloidal cuprous oxide.

Sanders (84), in United States patent 1,803,870, issued. ilay 5,.1931,
applied for October 3, 1927, claims a process which comprises forming a
colloidal suspension containing a metal, the salts of which are adapted
to kill low forms of life, by reacting upon a compound of such a metal with
a casein compound, the p-roportion of the casein compound being not.less
than 1 pound of actual casein to 2 pounds of the metallic metal.

"In ra:inc up a paste copper f;ungicide it is preferable to
addC 4 lbs. of casein or 10 lbs. of calcium caseinate to 50 Ibs. of
paste formed by adding 25 lbs. of calcium hydroxide and 25 lbs. of
copper sulphate to 50 gals. of water and filtering, as otherwise






- 26 -


sonome of the colloidl,. co;..'--r would bo lost in the filter water. It
will bc understood, furthermore, th.t the ab-.vo ni;:turos nay be ad-
dclod to other insecticides or fungicides, either bcioro or after
causing then to rc.'.ct in water.' For exxonple, dry atrscnical con-
pounds or dcorris or pyrethrun or other insecticidal powders nra-r
be added to tieo dry mixture of the copper conportn:'1. and the casein
compound, or various fungicides or insecticides, such as enulsi-
fiod oils, nicotine or dorris compounds, etc., 1ayr be nixed with
the wet colloidal copper nixture."

Linlecr (57), in United States patent 1,(-20,394, issued August 25,
1931, applied for March 9, 1929, in Gernany, .!?rch ]2, 1929, assigned to
the Deutsche, Gcsollsch-ift fur Schadlingsbckanpmfugr- .'3.H.. of Fronkfort-on-
thc-IIai:., Gcany, claims a n.thodc of funigatin. 7hich c-,nsists in con-
verting a cy%-_idc of a :ctnl selected from thoe -rov.', cO-r isinj alka.linc
earth metals and n a -roium-, into shaped bodi-s of a size the hydrocyanic
acid content of which corresponr's to the c.iount required for funi(,atirg,
reducing the shaocd bodies into ;ow/cr, and bl.7ing the said powder into
the space to be funigated.

"Accordiz; to one method 'f carrying my invention into effect
other auxiliary subSto.nces, for cx2.m .:e, such as are also capable
of acting upon the v-re.ir to be dectrycd, as-for example, nicotine
or suitable nicotine compounds, as for c^?.n.le, nicotine sulpi.-..to,
pyrothirun, dorris root or stinulatinr or preventative substan-cs,
rhich vol atilizc sinultaneously- with the Lydroc,, a.nic acid which is
given off nay be incorporated with- the pulvcrous alkalinc earth
cyanide conLpounds or the shaped bodies to be ;roducecl therefrom."11

Sanders (85), in United States patent 1.,847,540, issued March 1,
1932, applied for arch 11, 1930, claims a r.cthoc f coating particles of
insecticide dust an d causing then to bcconm floatable )n water by utiliz-
ing the heat of slakin.- lino for neltin:- stearic .acid to coat the par-
ticles. Sufficient water is added to quicklimc to convert all or a por-
tion of it to hy('rated line.

Tis -s water may carr: in suspension cr in solution a. poison
or the poison -iny be added separately cithor before or after the
water. While the mass is hot and, being ,'.." itatcd I acdd a fatty
acid enough to coat nost of the -particles in the nass and render
then floatable. The fatty aci' nay be ixe' with either tc. lime
or the poison either before or after addin, the water to the line
without departing from the q.irit of the invention. I then grindc
and air float in a suitable nill. An oxranplo cf the -r'.portions
used is: 300 lbs. quickli-:c, 300 lbs. paste cc per arscnite.
When at its naxinup heat andi under acitation add 12 Ibs. of stearic
acid. This mixture should. be gr-_und before usin; to '-ct the best
results but -ray be ussed directly.11 "Other insecticides other thaz-
arsenic nTy Ib used as finely ground pyrethrumn, hellebore, dorris,
nicotine dust, etc."








- 27 -


'3-ill1 (72), in Unitepr States tentt 1,-54,948, issued April 19,
1?3a, "i-tli-:.I for No;venber 7, 1.'27, claims a solution containing ro-
tcnone.. LateI for use in the mothproofing of fabrics. Ie -also claims a
noth roofrr. solution cont',irif ani e-tract of derris, or of naiari.

"T.he invention Will or rc.il- -AT..naerstood from tice. following exam-
pl]e.

"One poundC of derris root is rromund to a porder a2nd admixed: u'7th
i'or of petrlen aphtha, boi'lr.- between approxiLatcly 300 =d 400
F. TL mixtrc is aliowed to stai. at room temperrature for a consid r.:lc
priod, for U-c fiv_. to soren da.-s, beo.r:- ocasion-Il.- aGit2te'l during
this 111Crid. The -.y"!.cca'bo. oil containi4hC the 2csirod active principles
of tiho dorris root in then rcm--"oed, filtered clear a-.d, if desired, minute
cnou.nt; of cr:seti.-l oils or. otLi. r s'.itablc odoriicro-Is c'.iub.tu.nces mr.y be
_A .

Sr the cxtriact, if it is, -.sir;... to h..ston the operation,
tho i-.tu-rc of oil and xi>.7 c:cd root r;: ',' heotcd sildi, s,- to a tcmpor-
L'.t;.iC of 150 to 200 0., ,I'.i pried required -or the extraction of the
aclivc. princi,ico ,by tho oil i!.. tt:or~b subs, tajntially redCuccd, sa;- to 24
or .' LoU:'L.

tractss oof .iCiari ma. be ir-ducod i. the o-ac n.".c-'. In
r.rin-- lac`- haiari, it io T ,rcfcrrcd to ,xtr...t both the roots asd.
ster, while in the cse of whit e iaiari, it is preferred to extract
the stc:m rand !oaves.

"It!k soticn produced -.s dcscrriboe is ....'iculrlal suitable
for bso by d i-j-.. the fbric.; tlixrin, prcss.- out excess solution
and T-... : I. thio" war.a, rotononro io distributed over every fiber
"- the fabric, which is thcrc.bi rendered .oth .r'rf for a consider-
able ti-e. The mth ,'r'ff"' dip n ay uit-'.ll: be the l].st ste1 in
a dry clc:.Tnhe operati i-o: .

"There it is cczired to apply the. active principle by noans
of a v'i.:r', it is prcferrcd to oe:mIoy a 1w'ir boilin, naphtha cut,
for oxaiple, m-).-c. *. ilir..-' bntw cen 5-5,500 'F., since the slo%7or
ervponation of such naphtn.- p-oernits a noro comnplto penetration of
the ;::tracts into cve:ry portion of the fabric or garnet which h
.t. not be lircctly exposec. to the -,r'rv

"Uhilc it is preferred to u-;pl-." petrolenm naph-iths as the
:--:tr,,cting fluid, it Mrat be -J.. .rstoo, that thu invention is not
in.. :,..... to be linitc,', in this rcsp.-ct since alcohol, benzol, other,
anO. other sinilar Drganic solvents are also offcctive in extracting
i h~l.'L.:_ in sciluti-n thc active principles of cerris root and
other substa.nccs contoi";.n rotcnonoe






- 28 -


"Rotonone hns ir'.prtant properties which rendecr it invaluable
as a mothproofirg agent. It can be -,pplied with groat cacs. It
has no pronounced or objectionable odor. It is of relatively low
volatility so that it persists n the fabrics for a considerable
time. It is highly toxic and repellent to the moth larvae, but is
non-injurious to human beings and warn blooded aninals."

Jones (49), in United States patent 1,928,256, issued Soptcnbcr 26,
1933, applied for August 23, 1930, clai.is ovi insecticide comprising water,
rotenone colloidally dispersed therein, :,nd a sm-.] proportion.of a pyridine
base. For c1::.,le, 1 gran of -pure rotenonec is dissolved in 100 cc. of
pyridine. One cc. of this solution is added to 100 cc. of distilled watcr
and shaken gently. A pale opalescent colloidal solution results which shows
no ovidenco of separation over an extended period of tiic. Theli various
:iethyl pyridines (alpha, beta, and ganma picolines), the di.ethyl, trincthyl,
oth'1, allyl, and other alKyl-pyridics nay bo cnployed in pl'.ce of pyridine.
Similarly the cdipyridyls and other compounds containing a pyridino nucleus'
mnay be used. These compounds are included 'under the terrn pyridinee base".
In place of pure rotonone, a crude rotcnono, or an extract of a plant con-
taining rotenono may be used. For example xtractives front Dcrris olliptica,
Lonchocarpus, and other plants known to contain 'r)tononc na, bc employed.

Jones (50), in United States patent 1,928,2?'C, issued October 3,
1933, appliod for Avrust 23, 1930, claims a process of producin, a liquid
insecticide. contai.. -. :- rotcnonc in a colloirlal state of dispersion which
consists in dissolvinF rote-anone in acetone, and a'''i:-n this solution to
water in the prosenceo of tannic acid with subsequent -ixing. For e2Wvnplc,
4 grams of pure rotenone andl 2 grans of tmannic acid U. S. P. are dissolved
in 100 cc. of acetone, a clear solution rTsilti:. :. 'wo and one-half cc.
of this solution is addod to 1,000 cc. of distilled water and shaken gently.
An opalescent colloi:dal solution results which shows no evidence of separ-
ation during; an extended period of tine. In atton:ts to form suspensions
such solvents as acetic -.cid, acetcne, diacotono alcohol, othyl alcohol,
ethyl fornate, ethyl.one chloro:.ydrin, a.d pyridine have been tried. With
the exctin of pyridine, none of these -avo satisfact',r- sus:cnsions when
no protective colloid was added. Acetic acid, ethyl alcohol, ethyl fornate,
ethylene chlorohydrin, and pyridlino did not give pcr:iancnt di.plrsions in
the pr.-sence of a protective -iatorial such as tanrnic acid. Acctrno rnd
diacetono alcohol, on the other han.r, have bcc. found to give very satis-
factory results when used in the presence of theo proper amount of suitable
protective material.

Experiments have been .ad to test the efficacy of a number of pro-
tective colloi(-s for this purpose, the protective materiall beiig dissolved
or suspended in water and an acetone solution of rotonono a-,cd. A-onc
.w-i -hatui -rc,,tn ttnrh,,~
those wore Cium acacia, [,um karaya, .U ghatti, clatin, starch, agar-agar,
saponin, tannic acid, triothanol..aninc oloate, Pmroniun ca.;inate, potassiuu
oleatc, calcium caseinato, .i-.toriaceous earth, bcntonite, and litholione.
Tanic acid was found to be the. nest suitable material as regards suspending
" or protecting power, as well as from the standpoints of s-lubility and cost.






- 29 -


I:: .-.cc of acetone mothyl ethyl kotono, diethyl koonc.c, 2ethyl cothl
acetone and. _cctyrl acetone nay bce usedC. In like nrnner such aryl co.i-
pounds as phoenyl- 6thyl ketono mnd o- or -'h1.;, toll ketone nay be
eCriloycd in place of ac, tone or di-acctono alcohol. iL place of pure
rotonono, a cr1idc rotcrone, or an extract of a -,lant cI'nntar.. rotenone
nmayj beo used. For cxnple, er:tr.tivcs front Dorris elliptica, Lonclhocarpus
and other plants known to coiLa"- rotenone ;-,M be ,mployedI.

G:.2nt (32), in Unitccd States patent 1,934,057, issued Nwo:vonbcr 7,
1.33, aopp1lied for c.-obror 31, 1. 3r., aIsifnCl to thc Standcard Oil Dcvclo-
i.cnt Ccp.ny claims an insccticideo or insect repellent conprisinr; a pc-
troIemu white -il, c'ri s cxtrct, a.nd an c..- 'lsif--ing aont. T..o cerris
r;ots are extra.cted vith a volatile solvent, s-uch as benzol, isopropyl
alcohol, etc. The; extraction nay be carried out b:, any of the kno-:n
n:-h.;ds, such as porcolation, naccration, etc. This nethodO is especially
ac' Itcd to prepare concentrate(' Cxtrrcts a(.d consists of causiln the sol-
vent to flow -ver o." thr'-ujh the o:,b-tancc to be cxtrc.ctc e without flooding
it. The volatile solvent is -.h:n cv-. ,rate& partially or wholly, pr-,'or-
aoly in vacuo, lc.vin,; a conc.ntratcl dcrris extract. Th.' latter is then
o-ulsificcl with a potrolcur: oil, preferably of the kind' kro-m as ,-Ahitc
oil, and made.o by intensive acid treoatcr.t of gas-oil or lubricating-oil
fractions, such as nachne oil, transfor-icr oil, light or niiri- lubricat-
iz oiniR, etc. The e'lsificetion ,; be carried. out by dissolving an
c:.Ulsifyin-; c. .'nt, such as so, in tie white oil and fecclin.-. it, together
with the "-ry derris c.,tr_.ct, into a colloid :ill to obtain a. stable cnvl-
sion. So-c wTater ?Jay be t!horou. i:" adjixcil with this product before nar-
kett ..

Another ncthod which :.ay often be sed wi th '.tae is the fol-
loiim ,. Th- inscticidal or active principles of the dcrris root aro ex-
tractc. di"cctly wit'2 the "white oil." Volatile sclvonts such as alcohols;
ethers; esters; ketones, for instance acetone; : -ro.-atic hydrocarbon.s, for
ins'cao... benzc.-,o; or chlorinated hydrocarbons m -y be added. to the white
oil to increase its solvent power. In this case, however, it is nreforable
to distill off subsequently nost of the volatile solvents from the product
obtained,. A similar result .,.y be obtained by adding stcan distilled pine
oil, terpincol, phenol, cresol, or their honolo:s, cylohcxaLnol and its
hon-ologs ,.d"rorronatc.d naphithalenes such, as tetralin or dccalin, chlorinated
napt'halonas 5sich as halowax )il, etc., to the white oil to increase its
slvcnt .o;.,cr for the derris extractives. T'.e nLrcei.aonts just iontioned
can.-Inot cnd shv'uld not b.c ren:'vei. by subsequent distillation but remain in
the product "n.. c-nfer upon it a f.ncicidL-al amd bactericidal effect in ad-
dition to its insecticidal- 2-5crties and facilitate its onulsification.
The derris--whitc oil c.:,tract is then 'nixod w-ith an enulsifyinA' oIont, such
as fatt soap, rosin soep, sa,)onin, soaps of ;ctrolcu' sulphonic acids,
soaps of suphonateCd vw.&tablo or aniiicl oils, ,to form a cor-.osition capable
of disporsinG in mater. Any one soap or a mixture of several soaps niay be
used. Part of the soa-p :-nay be a-dded to the white oil before the extraction
because it`'as been found that the presence .-f a soap facilitates the eox-
tractijn. Oil-soluble s-;lphonatos arc p-fcrably usoCe as an onulsifyinc
af;ent, and are obtalne-'. in the refining: of said white oils.






- 30 -


The product may be marketed either in the form of a homogeneous liquid
mixture of oil, derris extractives, enmulsifier and added solvents or fungi-
cides, practically free from water, or in the form of a stock emulsion of
creamy or buttery consistency containing up to 35 percent of water. Its
composition may greatly vary according to the requirements of the market and
the transportation facilities. Products containing as high as 75 percent
derris extractives may bo prepared. The practical limits of the components
are the following:

1 to 25 percent derris extractives, 40-80 percent white oil, 5-25
percent soap or other emulsifier and fungicide, 0-35 percent water. Usually
the percontie of the derris extractivcs is kept within the limits of 1 to
10 percent.

The marketed product is further diluted with water before use, to
such extent that the composition of the final diluted spray is about the
following: 0.06 to 0.25 percent dorris extractives, 0.5-1.00 percent
petroleum white oil, 0.2-1.00 percent soap, 97-99.00 percent water.

This new insecticide is effective against pests such as the various
aphids, tent caterpillars, scale insects, redmite, tomato moth, cnbbasgo
worm, saiflies, etc.

An example of preparing this insecticide is as follows:

Two kilograms of ground dorris roots wore extracted with 4 liters
of benzol. Distilling off the solvent in vacuo, 113 grams of dry extract
were obtained, representing 5.65 percent of the dry derris roots, and
having the appearance of a reddish-brown rosin. Eighty grrns of this extract
were fed into the colloid mill together with a solution of 750 gr.is of oil
soluble sodium solphonato in 2.5 liters of 'V17rol11, commercial brand of
white oil. later was also added in the amount of 1.5 liters. A thick
emulsion resulted similar in apporranco to mo:aunnaisc anrid ready for rMarketing.
Part of this preparation was diluted .with 50 times its weight of ;Jater and
gv ac final spray which was effective when sprayed on trees -.s nn insecticide.

Badortschor (2), assignor to McCormick & Co., Inc., in Unite(. States
patent 1,938,352, is.-uod Doceober 12, 1933, applied for August 20, 1931,
claims a horticultural spray includin- pine oil, an insecticide, n.d dipen-
tonae, the dipentoe.e being present in amount in excess of the nmount nrrmally
present in pine oil arnl in quantity sufficient to substantially negative ,
the tendency of the pine oil to burn foliage. Any suitable insecticide may
be included as, for example, nicotine or nicotine sulhatc, rotonunc,pyrcthrine
as an extract of pyrethrum flowers, quassiin as an extract of quassioa chips,
etc.

Grant (33), assignor to Standard Oil Devolopnont Co., in Urnited
Stat,.s patent 1,940,64:3, issued Decemrber 19, 1933, applied for October 19,
1927, clai'-.-s in the ramifacture of insecticides, the irprovoncnt which
cor.prises extracting the active insecticidal principles from vegetable 2at-
ter of the group consisting of pyrcthruar, derris, cube, and tephr-sia, with a







- 31 -


ni:;turc of an organic solvent, a blending a-kcnt and. n onulsifyirig r*I:nt.
Preferred or-'anic solvents :,re naphtha, kerosene, and light lubricating uil.
Suaitablc blc:-din, 4-onts are: oil soluble sulphonates, Turkey rod oil, rosin
..p, ;_.natod vegetable or mineral oils, stea:. distilled pine oil, torpin-
o0l, cresol, cyclohcxcanol, dichlorobenzcne, chloronapjhthalene, ono or :.Iro
of the higher alcohols, such as isopropyl or secondary butyl or secondary cnyl
alcol 1, ketonos, or cycl-hecx-nol or its horiolog-es. Sone of the above
natorials -.ny scrve both as blending agents and as enrulsifyin- -gents. Such
naterinls Laving this dual property are oil soluble sulphonates, Turkey rod
oil, o-. lrhonated vegetable or animal oils and to a certain extent als, rosin
so-ip. The active principles nay be extracted. with other solvents, for xam-
ple, :-lcoh-ols (ethyl, is'tiropyl, etc.), benzol, or carbon tetrachloridlc. The
extract so prepared ni:;y be concentrated to yield an oleo-resin which may be
nixe. witih oil-soluble s-lphonatc in suitable percenta'os. Various substances
nay be n'el to the composition either before or after the organic -.atorial
is extracted, and before or after concentration by evaporation or distillation.
Phe.ol., cresols, pine oil, etc., are suitable for this purpose. Illustra-
tive co:, site solvents are: (1) kerosene 31.6 cc, oil-soluble ullahonate
18.4 cc, .,rttcr 2.0 cc; (2) kcroso-.o 31.6 cc, oil-soluble sulphon..te 13.4
cc, secbu-,hry butyl alcohol 10.0 cc, water 68.0 cc; (3) kerosene 31.0 cc,
Ail-solAuble sulphornate 18.0 cc, ethyl methyl ketore 10.0 cc, water 35.0 cc;
(4) pctroleunm white oil (vis. 75-85 sec. Snybolt a,.t 100 F.) 45.0 cc, oil-
soluble .,ql-hoenato 5.0 cc, dichlorobenzone (crude) 9.5 cc, water 2.0 cc; (5)
mineral ceal oil 171.3 cc, oil-soluble sulphonato 30.2 cc, potash rosin soap
10.0 g., hex.ahydroh.nol 10.0 cc, ethyl methyl ketonc 10.0 cc, cresol, U.S.P.,
10.0 cc, water 24.0 cc; (6) petrolum white oil (vis. 75-85 sec. SaybAlt at
100 F.) 128.0 cc, oil-soluble sulphonate 14.2 cc, secondary ayl alcohol
6.6 cc, steo distilled pine oil 6.6 cc, chloronnaphthalenes (cride) E.6 cc,
potas'- rosin soap 8.6 ,.,., water 17.5 cc.

B3.ad.ertschor (3), assi.--nor to .:cComichk & Co., Inc., in UniteK States
patent 1,940,89, issued December 26, 1933, -.. .lied for January 21, 1932,
cloi.:s the T;oCthod of producing a horticultural dust whichc h includes spraying
.a n^-.- '.2>1e inert material in finely l.i-idcd forn with the active grin-
ciple uf -pyreth.run in solution in a volatile solvent "-hilo agitatink the
inert material and nainta.inirn- it at a temperature at which the solvent -.ill
ovapu rate.

ro non-alkaline inert material nay bo a siliceous earth, talc, bcnton-
ite, etc. Te-. active principle of pyrcthr-a :.-y be used in admi: ture
with rotonone. A horticultural dust nadoe in accordance with this invention
nMay conTrise 80-95 inert material and 5-20 pyrothrui:, or pyrethlrua nand ro-
toroncu, -vc. the coated, inprc.-.atoed, inert material may, if desired, be ad-
nixed wit'. ground derris root or rou.-id cube root in the proportion of 60
parts inert material to 40 parts of ground derris or cube root, or a r.,ixture
there ,f.

Jo-,c (51), in United States patent 1,942,104, issued January. 2,
19-1, -"7 plied for Fobruary 20, 1933, claims a process for naking a chcrlical
cor.pou'.1 of rotenone and carbon totraclorido which consists substanticlly
in extracting the roots of plants of the genus Do-,cilia (Dorris) with warn
carbon totr-,.chlorido, and crysta-llizin-. Boots of Lonchocarous or S.iatholobus
TnI be uscd likewise.






- 32 -


For example 50 grams of the roots of Deg-uelia (Derris) sp. (tuba root)
is completely extracted in a continuous extractor with carbon tetrachloride.
The extract is evaporated to a volume of 25 cc. and cooled in a refrigerator.
When crystallization is complete the separated material is filtered, excess
solvent removed by suction and the noedlclike crystalline product dried in
the air.: The solvate C23H2206.0014 contains 71.9 percent by weight of ro-
tonone and has highly valuable properties as an insecticide, and mothpro6fing
agent.

Mills and Fayerweather (75), assignors to tfl Dow Chemical Co. in
United States patent 1,942,827, issued Jn/,uary 9, 19734, applied for I',-rch 27,
19,3, claim 1,2-dihydroxy-4-tertiary alkyl benzene, especially the tertiary
'butyl and tertiary amyl derivatives. As little as between 0.D0O1 and 0.05
percent of those compounds in gasolinc inhibits gum formation. Theso new
compounds may also be employed 4s stabilizers for insecticide compositions,
such as pyrethrun and rotenone. They may also bo used as antioxidants in
vegetable and animal fats, wax s, soaps, etc.

Hller and Schaffor (34), in U. S. patent 1,945,312, i3;.3uod JaCuary
30, 1934, applied for April 10, 1933, claim the process of naling di-hydror-
otenone which comprises hydrcgenating a rot or.0o0-bearing plant extract
dissolved in an organic solvent in the presence of a nickel catalyst obtained
by alloying equal parts of nickel and alunainum and then dissolvi-g out the
latter with aqueou. sodium hydroxide. Benzene, acetone, ethyl '-cotato, Lond
ether are suitable solvents. The reaction proceeo.s at atmospheric pressure
and at room temperature and the yield of dihydrorotenono is about 90 percent
of the theoretical.

For example 50 grams of tho groain:d root of Deo.-uelia (Dorris) sp.
(tuba root) is exhaustively extracted in a conutir2-uous extractor with acetone.
The extract is concentrated to 50-75 cc. and placed in the reaction bottle
of a suitable catalytic reduction apparatus and 3 rramns of r-nickol catalyst
suspended in 10 cc. ethyl alcohol are added. The apparatus is evacuated,
then filled with h-,Irogen and the mixture is shaken with 1iydro7L'n ur-til the
rate uf absorption of hydrogen is very slow. The solution is d.c-.-r.nted from
the catalyst, filtered, and concentrated to a small volume, and 10-25 cc.
of ethyl alcohol are added. After standinC for a short time the crystalliza-
tion of dihydrorotenor.e is usually complete. The product is practiCrlly pure
dihydrorotenone.

BTusquet and Tisdale (ll), assignors to E. I. du Pont do Ncmoure & Ci., in
United States patent 1,954,517, iss-ued April 10, 1934, applied for July 8,
1932, claim the method of killing insects vhich comprises contacti-ng the
insects with a writer emulsion of beta beta-dichlordiethyl ether and an in-
secticide of the group consisting of water-insoluble dithiocarban-.tes, water-
insoluble thiurc: sulphides (especially tetraethyl thiuram monosulphido)
and the toxic in-;redient of dorris root.


E:,am1p leu are:






- 33


Y'-.sturtium plants infested with black aphids wore sprayed ;.ith a
sm.,.., o.isiori containing 0.1 percent of a solution composed of 10 percent of
the toxic ingredient from dorris rojt and 90 percent beta beta-dichlordiethyl
other. After 24 hours, noro than 99 percent of the aphids were dead.

Co-:non houseflies wore sprayed with kerosene containing 2 percent of
a beta beta-dichlordiethyl ether extract of derris root. Approximately 90
percent of the flies were p-.ralyzcd in 6 minutes and 90 pcrcont were dead
in 24 hzurs.

Dougherty and Andecroi- (21), in United States patent 1,963,838,
is.u&'C. J1:-,o 19, 1934, apPlied for May 23, 1933, described a portable sprayer
which a uses stoe-a.; oenerated by an electric, heating unit to expel insecticidal
fluids. Rotcnono is -..citioned as a botanical. derivative Tich can be used
in such an insecticidal composition.

Fulton (28), :asi7n.or to StancL. Inc., in United Stntes patent 1,967,024,
issued July 17, 1934, applied for June 6, 1929, claims an insecticide con-
prising pyrethrins and the active o' >'.-;t containing; rotenone obtained from
a plant. For exanple pyrethr: extract is preyarod by extracti:g pyrethrum
flowaors with 8 tines their woi-ht of kerosuno and decolorizinc the obtained
solution with 3 percent of its weoiit of chemically r.repared absorptive clay,
su&ch -s "Filtrol". This is i-.provcd by dissolving 0.025 percent by w.eight
of rotenone in the extract. In case it is desired to dissolve A' higher per-
contv-,c f rotcn oic it is ncecoss:arj to use a nixed solvent. If for instance
1 percent by weight of chloroform is added to the pyrothr'e-kerosene extract
0.1 percent by weight of rotenone is soluble in it, i.e., four tines as much
as in the -bsonce of chloroform. A benzol extract of derris nay be used in-
stofad of pure rotcnrono. Carbon tetrnc:loridc is also mentioned as a solvent.

Bouusquet (10), assignor to the Gr sscclli Chemical Co., in United States
patent 2,006,227, issued June 25, 1935, applied for October 19, 1932, claims
a contact insecticide comprising an aqueous preparation contrinirn technical
soy- bca:. lecithin -.s the essential active iri-redIient and sulphornated fish
oil or !t.'l alcoh.ol or other irn1redients as a dispersing n.-cnt. It is stated
lecithin preparations are compatible with other contact insecticides such as
nicotil-e, rotenone, and pyrethrum preparations.

Ja.yCs (48), assignor to C. P. Byrnes, Trustee, in United States
patent 2,006,456, issued July 2, 1935, pp:liei for M.-irch 12, 1930, claims
in the- process of treating, sulpho-nated products obtained by treating lighter
petrulci.. fractions such as gasoline with sulphuric acid to obtain an enul-
sifiable insecticide or fungicide, the stops consisting of neutralizing the
sulphuric and sulphurous acids present by adding, a strong solution of a
"iater-soluble alkali capable of said neutralization, removing the neutralized
aci., then aUitatiL: the remaining mass with a weaker alkaline water solution,
decanting and rerioving the water solution, then washinC the remainder to re-
move excess alkali, and then adding a small percent-ce of an insect poison.
Th'e insect poison nay be nicotine,derris rot, or other organic poisons, or
inorga.nic poisons such as copper and arsenic derivatives.





Z :34 -


Voorhees (99), assignor to the Standard Oil Company of Indiano, in
United States patent 2,011,428.` issued Apgast 13, 1935, applied for Hay 4,
1931, clcir-ms "an insecticidal. and fungi.cidal: composition comprising C. min-
eral oil, an oil-soluble organic insecticide of vegetable origin which
tends to lose its toxicity in the presence of light, and a light-scrocning
oil-soluble organic compound- selected from the class consistiWn of nmino an-
thrraq-u.i none s. .

"Also di-amino and substituted di-aniro anthraquinones m. be used.
The nucleus of the anthraquinone and the organic rcsiduo may be substituted
with alkyl, aryl, ,aralkyl, nitro, hydrox.yl! -nd othor groups. 'Tho above
class of anthrrvjuinone compounds include phonylated amino anthr-quinonrn,
o0-qhc:fyl-rminoanthraquinonos, alkyl phenyl rtnino, anthraqcincno s, diarylnjnirno
anthr-quinoncs, 1,4-toluido anthrr.quinone and aryl diwmino anthraquir.oncs.

"The followin-; specific exrnple of a concentrate eonulsi.n suitable
for dilution to yield an insecticidal or fungicid.l spray is as follows;
Gum ghatti, 2.4 percent; cresylic -.ci., 0.1.8 percent; water, 35 percent; white
oil (80 second Saybolt at 1000 F.), 62.4 perc-oit; and 1,4-toluido nnthr.-.
quinioe, 0.02 percent: The cjrccn.tr.ted emulsiojn .'cy be prepared by intinatoely
nixi-ng the irgrcdicnt' in a colloid mill or by passing the mixture through
a centrifugal punp or in rany other suitable manner. to give o, corncL-ntrated
e0aulsifiablo composition which nay readily be Oilutod to ;.ield a'n er.ulsion
suitable for spraying purposes."

"TIne oil may contain the active principles If pyrethru or other
"oil-soluble or:anc.- insecticide of vegetable origin" [e.g. dorris extract.]

Buc (12), assignor to Standard. Oil Dcvol.opi.,cnt 0o., in United Stntes
patent 2,013,028, issued Soptoriber 3, 1935, aoplied for March 12, 1931, clirmns
an inoccticida.l composition consisting of a non-volatile viscous potroleun
oil contrJning not less than 0.1 percent of insecticidal iatcrial sclocted
from t:ho group conrsistin-i of rotonone and rotenr.Ai'.s anrl not less th:..n 1.5
percent of a non-voI'i'.o highly hX: loycn'r.tel ,.'lroc.rboi. BRc' lcfines ro-
tenoi-..s a.s the in octicidal principles of certaiA fish poison plants such
as de4.ris and cu.i x;/h are not exactly iOentical witl. rotenono in their
chemical constitution but ht;v.e a similar insecticid-al action. A suit,.v-le
insecticide Tiay. be nade by dissolvi-:g 1 cram rotenone, 20 ,gran.s .lu..c:,tcd
naphtha lone of specific C'ravity 1.25in 1 liter kerosene. Other ea:,ples
are: (i) 2 *r;-r ',3 tc:teone, 30 7rr.s- hrlo.enf t n-,phthlaenc (hol-owcx oil)
of specific rTviy ,:-5 in 1 liter li,-ht lb--i&a'.L:l o'i.; (2) 1.5 .*r.ns
rotenon, 25 gruas of chlorinatcd gasclL.e conGaci:.un 50 ,,.rcer.t of chlorine in
1 lier of petroleum oil hLaving a gravity of 27 A.P.I. and a viscosity of
115 Sayjbolt at 100 F.; (3) an aqueous c.-.ilsion containing 0.7 percent of
thc cor.iposition give:. in ET.:arple 1.

Schotto ,,nd GSrnitz (90), assi;nors to Schcrin;-Kahlbaum A. G, of
Berlin, Girr.-iany', in United States patent 2,024,392, issued Decomnbcr 17, 1935,
applied fQ-r December 12, 1933, in Gcrnmny, Nove-iber 13, 1931, claiti -.n insecti-
cidal preparation consisting of a mixturo containi:-; rotcnor-o nr.d ".-cr-trin.






- 35-


They also claim an insecticidal proparption consisting of a mixture con-
taining 2.5 p,.rts radix dcrridis ollipticac a.d 7.5 parts s wicT sabadilla-e.
Thoe p-tuntees state that by combining one of those drags containing rotenone
with a durag containing veratrin, for instance sabadilla seed. or ca c-.tr-ct
or alkaloids recovered from such products, !a insecticidal effect is ob-
ta.iroil, 1vhich is far gre.atcr than the effects exerted by the two drugs if
used sirngly.

"That this is true, is shown by the followinZ compar=.tivo
tests made by usi.-:g strowable trceparations cr.sisting of intimate
ground nixturos of semon sabadillaoe with talc, radix dorridlis cllip-
ticae with talc anl with a mixture of sr.cnn sabadillao -:.,l -ix
l-eriidis olliptic'.o. In each test 30 caterpillars of Tcphruc-lstia
absir-thieta Cl. (Goometridaoc) placed on blottong paper were duasted
v ith a quantity of one of the mixtures corresponding to .16 nil-
li.ran per square centimetre, the powicr being even tdistributedl.






- 36 -


ea N Iumber of-
Preparation. a caterpillars
caterpillars not killed

Talc + 2.5% derris root ......... 1 29
Talc + 5% derris root ........... 10 20
Talc + 7.5% derris root ......... 18 12
Talc + 7.5% sabadilla seed ...... 17 13
Talc + 10% sabadill-'. seed ....... 19 11
Talc + 15% sabadilla seed ....... 26 4
Talc + 2.5% derris root + 7.5%
sabadilla seed .............. 30 0
Control test .................... 0 30


A ground mixture of 2.5 parts radix derridis ellipticae, 7.5
parts semen sabadillae and 90 parts talcum proved useful in exter-
minating grasshoppers (for instance Tachycines asynamorus), flea beetles,
bugs (Lygus campestris) and many kinds of caterpillars. Instead of the
drugs themselves we may also use their effective extracts or the alka-
loids recovered therefrom, for instance by mixing 0.2% rotcnono, 0.3%
veratrin and 99.5% kaolin."

Hamilton (35), in United States patent 2,030,584, issued February
11, 1936, applied for June 5, 1934, claims an insecticide including water,
a suitable oil, and finely powdered natural parts of a plant selected
from the group consisting of derris and cube root containing an inherent
emulsifier and properties toxic to insects. Reference is made to the use
of acetone, alcohol, ether, and ethylene dichlorides as solvents for the
active principles of dorris and cube. To prepare the paste, 3 or 4 parts
of finely povwoered derris or cube root are added. to 8 parts of water and
8 parts of oil either mineral, vegetable, or animal and the mixture
emulsified in a suitable machine. In case the derris is reduced to 1
part it is necessary to add 2/3 to 1 part colloidal clay (wilkeito, bentonite,
etc.) to make a physically stable emulsion. A preservative such as 1/2 to
1 percent of carbolic acid may be added; a sodium, potassium, or an
ethanolamino soap may be used instead of the clay and an antioxidant such
as tannic acid nay also be added.
The paste c ulsion insecticide produced as aforesaid, nakes a quick
breaking emulsion vhen diluted with water for spraying. Insecticide sprays
of this invention possess frcm 15 to 20 percent greater toxicity to plant
lice than sprays of the saic high dilution made frcm derris and cube
insecticides of the chemical extracted kind.

Hamilton (36), assignor to the Endovment Foundation of New Brunswick,
N. J., in United States patent 2,035,546, issued .March 31, 1936, applied
for May 14, 1932, claims a composition to be used in paste form for killing
boring insects including as ingredients a colloidal clay, an insecticide,
ethyl alcohol and only sufficient water to form a paste. The insecticide
may be an organic insecticidal material such as free nicotine, nicotine
sulphate, pyrethrins and rotenono. Rotonone nay be used in the forn of a
solution in acetone, alcohol, carbon tetrachlorido, etc.






- 37 -


Buc (13), assignrrr to the Starndard Oil Devel.p-.ent Co., in United
States patent 2,042,296, issued May 26, 1936, appliQd-.for March 12, 1931,
claizis an irsccticidal ipropir.tion, coriprisi:.g a relatively non-volatile
potroleum oil, insecticidal material selected from the -Toup consisting
of rotanono and rotenoids, and an ar-yl alkyl ether, the omouWt of aryl
alkyl ether being sufficient to keep the insecticidal material dissolved
in the petroleum oil. The following example is given: 0.5 Percent
rotenone, 5 percent secondary hexyl cresyl ether, 94.5 percent petroleum
oil having a gravity of 270 A. P. I. and a viscosity of 115 Saybolt at
1000 F. Buc prepared a stable kerosene solution containing 0.25 percent
of rotcnono with only 0.75 percent of secondary hexyl phenyl ether as
mutual solvent.

Ryan and Moran (83), in U. S. patent 2,043,267, issued June 9,
1936, applied for October 2, 1933, claim a product adapted to serve as
concentrate for a germicide, insecticide, or parasiticide, comprising a
product which is the result of a chemical reaction between the toxic
principle of herbs of the class including pyrcthrun flowers and derris
root with a chemical compound of the alkyllolamine family. For example,
derris extract, 1 part, is mixed and heated to about 100 C. with 0.7
part by weight of triethanolamine; then 1 part fatty acid (e. g. oloic)
is added. A "disinterested" solvent (one that does not undergo chemical
reaction) such as diothylene glycol monoethyl ether is now added in any
amount "depending upon the bulk and the ease of solubility desired."

L. E. Smith (94), in U. S. patent 2,049,725 issued Aueist 4, 1936,
applied for M-'rch 20, 1935, claimed diaryl thioxins, especially pihcr.o-
thioxin, as an i-Isccticide. Upon mosquito larvae, phenothioxin in nqucous
solutions in all concentrations up to 1 part in 500,000 was as effective
as rotenone.

Wothersponn (105), assig.or to Derris, Inc., in United States
patent 2,052,374, issued Auguot 25, 1936, applied for April 28, 1934,
claims an aqueous-disser'i:-,.atable composition of nr:'tter consisting of an
insecticide obtair.!ble from derris and similar ins.ctici-.al-coxtai.iig
plant materials containing rotenone, degu elin, tcphrosin, and toxicarol.
and a water-soluble phel.ol ccntainit-g at least two hydroxyl groups.

"I have found that if rotonone, dihydroroto :-cne, finely ground
derris or cube, solid extracts of derris or cube, the hyfrogenatcd
derivatives of same, either alone or in mixtures, are melted or intimately
mixedd with a solid water-soluble phenol containing twu or more hydroxyl
groups, the resulting product after codling and grinding is soluble, or
miscible, with water in any proportions.

"The products thus produced nmay be mixed, if desired, with a-y
powdered materials which act as wetting i-jcits, such as soap, alkali
salts of msulplonated hydrocarbons or alcohols, sulphonated oils, et cetera.

"Fillers such as starch, glue, guns, O.extrins, flour, clays, talc,
bentonite, chalk, diac-,maceous earth, et cetera, may also be incorporated
therein if desired.







38 -

"The maximum-results are obtained with these insecticides when
treated in this manner.

"The phenols referred to above may be one or more of the dihydric
phenols such as catechol, resorcinol and quinol and their homologues,
and the trihydric phenols such as pyrogollol, phloroglucinol and
hydroxyquinol and their homologues."

Examples are: (1) 12.5 parts by weight of rotenone are mixed with
87.5 parts by weight of resorcinol in a vessel equipped with a.heating
arrangement. Heat is applied and when melted the contents are withdrawn
and allowed to cool. The product is then ground in a suitable grinding
mill. This material is miscible with water in all proportions and when
so mixed is highly toxic to most insects.- (2) Twelve and 1/2 parts by
weight of dry hydrogenated derris extract are melted wibh 43.75 parts
by weight of resorcinol. The cooled product is ground to a fine powder
and mixed with 50 parts by weight of powdered soap. The resulting
product when mixed with water is quickly dispersed and yields a most
satisfactory hortiicultural spray. (3) Ten parts by weight of dihydro-
rotenone are melted with 90 parts by weight of pyrogallol. The resulting
product when ground and dissolved in water yields a valuable insecticide
that may be used for mothproofing woolen materials.

Organic solvents mentioned as suitable for dissolving the active
principles of Derris, Lonchocarpus, Spntholobus, etc., are ethyl acetate,
benaol, acetone, chloroform, ethylene dichloride, and safrol.

Ward (100), in United States patent 2,056,438, issued October 6,
1936, applied for September 4, 1935, in Great Britain, March 30, 1935,
claims the process for extracting toxins for the manufacture of insecti-
cides from barbasco root, comprising the steps of treating the root, in
a broken up state, with common alcohol in the proportion of 100 gr.-mmes
of the root to 400 cc. of common alcohol to which is added 1-1/2 per-
cent by volume of chemically pure sulphuric acid, allowing the mixture ,
to digest under the action of the internal heat generated, the common .
alcohol dissolving out the rotenone, tephrosin, deguclin, and toxicarol,
raising the temperature of the mixture by heat derived from an external
source, filtering the mixture, neutralizing the filtrate by adding
sodium carbonate thereto, refiltering, this final filtrate containing
not only the rotenone but also the degiielin, teophrosin, and toxicarol,
and mixing the final filtrate with soft soap. Reference is made to the
process of obtaining rotenone by extracting the roots with ether and
recrystallizing from carbon tetrachloride. This invention relates to
the extraction of toxins, for the manufacture of insecticides, from
derris, barbascoand tinbo roots, such, for example, as Lonchocarpus
nicou, Derris elliptic.., Derris chinensis, Derris malaccensis and other
roots containing rotenone.

Wotherspoon (106), assignor to Derris, Inc., in United States patent
2,058,200, issued October 20, 1936, applied for September 12, 1932, claims
a composition of matter consisting of a nonaqueous solution of the insecti-
cidal principles obtainable from one or more members of the group consist-
ing of derris and pyrethrum in at least one member of the group of alkylated


I" I - I' I I oh"' II..-Wn.M .*i .1i '1 .wi y c<




- 39 -


phenolic ethers consisting of safroli anethol, methyl eugenol, and camphor
oil said solvents being in sufficient quantities to maintain the insect-
icidal principles in solution. Solvents previously used to extract derris
and cube include benzene, acetone,' acetbne-4alcoh6l mixture, petroleum
distillate, chloroform, ethyl.nc dichloride,' ether, toluene, xylene, etc.
Solvents less effective than safrol, etc&. include oil of turpentine, pine
oil, terpineol, dipentene, phellan-drene, terpinOlene, limonene, cedrene,
and petroleum distillates, The new solvent extracts of derris or cube may
also be used in conjunction with water provided a proper colloid is
present to form a stable emulsion. These colloids are soap, starch, gum
acacia, gum ghatti, gum.karaya, gum tragacanth, dextrin, glucose, sucrose,
and saponin or extracts of plants rich in the latter.

The following are examples of this invention:

Example 1. 50 parts of a solution of the active principles of derris
roots in safrol containing about 10 percent of the derris extractives and
90 percent safrol. 50 parts triethanolamine oleate.

Example 2. 25 parts 5 percent solution of rotenone in c-.aphor oil S. G.
970. 25 parts concentrated solution pyrethrum flowers in camphor oil S.
G., 970. 50 parts triethanolamine oleate.

Example 3. 25 parts of a. solution of the active principles of derris root
containing about 10 percent of the derris extractivos and 90 percent
safrol. 75 parts of aqueous solution of gun Lcacia containing 10 percent
of the latter. This mixture is passed through a homogenizer or colloid
mill to disperse same.

Example 4. 15 parts of a 5 percent solution of rotenone in camphor oil
S. G., 970. 10 parts of a concentrated solution of pyrethrum flowers in
camphor oils S. G., 970. 25 parts of a concentrated aqueous solution of
cocoanut oil soap. 50 parts of an aoueous solution of gum ghatti con-
taining 5 p-rcent of the latter. This Tixture is passed through a homo--
genizer or colloid mill to disperse same.

Example 5. 5 parts of a 2 percent solution of rotenone in safrol are
mixed with 95 parts by volume of petroleum distillate. ,

Example 6. 10 parts of a 1 percent solution of rotenone in car.r'phor oil
are nixed with 90 parts by volume of pe'troleun distillate.

Example 7. 2-1/2 parts of pyrethrum extract (20 to l) and 5 parts of a
2 percent solution or rotenone in safrol. are mixedd with 92-1/2 parts by
*olune of petroleum distillate.

0ankowsky (86), Assignor to Stance, Inc., in United States
patent 2,058,832, issued October 27, 1936, applied for March 17, 1933,
claims a method for preparing a clear concentrated liquid insecticide
which comprises extracting rotenone and other constituents toxic to
insects, fromn.a plant contp.ining such toxic substances, by treating said
plant with a mixed solvent, which is cz.pable of selectively dissolving said






- 40 -.


toxic substances to the exclusion of resinous materials which, upon
dilution of the extract with kerosene, would be precipitated, comprising
a petroleum distillatehaving-a,maxinmnm.boiling point below 625 F.
and a sufficient amounttof an organic,-solvent soluble in the petroleum
distilla.te and having solvent power for said toxic substances to. dis-
solve at least 2-1/2 percent- of ,,said toxic substances.

Derrie root, cube rop-t, or other plants containing rotenone are
extracted by a counter-flow method, or by percolation, etc., with about
20 to 30 percent solution of- ethylene dichloride in a petroleum
distillate. A concentrated extract is obtained. containing about 2.5
percent of rotenone and about 5 percent of rotenoids. This concentrated
extract, after being clarified if turbid by the addition of a small
amount of ethylene dichloride or other similar. .solvent (e. g. p-dichlo-
robenzene is mentioned) may be used for the preparation of insecticidal
solutions by diluting with a petroleum distillate to the strength desired
without the formation of a residue, or it may be first mixed with a
concentrated solution of other Insecticides and then diluted to the
desired strength. The petroleuir, distillate prefetrably used i.s one having
a macimum boiling point below 6? F. The term rotenoids is applied to
the insecticidal constituents of Derris, Lonchoc ius, and Tephrosia
other than rotenone. Other solvents that may be used nixed with a
petroleum distillate to extract rotenone and rotenoids from derris root,
cube root, or other plants containing rotenone are as follows: acetone,
benzol, chlorobenzene, chloroform, dichloroethyl ether, ethylene
chlorohydrin, n-propyl format, toluene, trichloroethylene, and xylene.

Mikeska (74), assignor to the Standard Oil Development Co., in
United States patent 2,066,184, issued December 29, 1936, applied for
October 29, 1932, claims an improved insecticide, comprising a hydro-
genated extract obtained by extracting petroleum oil with a solvent
having a preferential solvent action for aromatic and unsaturated hydro-
carbons of a petroleum oil, separating the solvent from the extract, hy-
drogenating the separated extract and dissolving in the hydrogenated
extract the active principles of a fish-poisoning plant. For example,
keros-ne having a solvent power for rotenone and/or rotenoids of from
0.25 to 0.05 percent was extracted with sulphur dioxide. The extract
was separated from the solvent by means of distillation and the solvent
power for rotenon was found to be increased to 2.3 percent. The extract
was then hydrogenated and marked improvements both in the odor and the
solvent power were found. The solvent power of the hydrogenated extract
for rotenone and/or rotenoids was increased to 7.2 percent. The hydro-
genated extract is suitable for use as a solvent in extracting the toxic
ingredients from the fish-poisoning plants, by percolation or by
maceration of the plant in the presence of the solvent and separating
the solvent containing the toxic ingredients from the residual solids,

The hydrogenated extract with the toxic ingredients in solution
may be diluted and used as a spray in killing insects, such as flies,
mosquitoes, etc. A spray of the emulsion type mpy be prepared for
dipping and spraying animals to control external parasites, such as lice,
ticks, mange mites, cattle grub, etc. The emulsion for cattle dips or







- 41 -


sprays is prepared by taking; hydrogenated oil extract solution containing
5 to 10 percent of rotenone arid/or rotenoids and mixing with water, using
a suitable emulsifier such as oil soluble sulphonatod soap, fish oil soap,
saponin, etc. Other insecticides may be added to the emulsion, such as
lead arscnate, nicotine, pyrethrum, etc.

Another use for the spray solution of the emulsion type is for
Uprrying plants such as trees, shrubs, etc. to control parasites such as
aphids, leafhoppers, thrips, greenhouse white flies, tent caterpillars,
red spiders, squash bugs, roaches, iLcxican bean beetles, Japanese beetles,
potato beetles, etc.

Rotenoids are defined as the non-crystalline extract of fish-
poisonineD plants consisting of a mixture of deguelin, tephrosin, toxicarol,
etc.

:Jilgpre (53), in U. S. patent 2,070,603, issued February 16, 1937,
applied for January 3, 1936, claims certain esters as insectifuges or
insecticides. An example is mesityl oxide oxalate methyl ester. Botanical
extractives (e. g. derris extract) Ithemselves toxic to a greater or less de-
gree to insects may be combined with one or more of the compounds described
in this patent. In this way the insecticidal and insectifugal values of
such extractives are enhanced, and stabilized.

Sessions (91), in U. S. parent 2,083,098, issued June 8, 1937,
applied for April 4, 1934, assignorr to the Cplifornia Spray-Chemical Corp.]
claims a parasiticidal composition comprising a neutral copper-calcium
silicate containing complex, and a botanical insecticide selected from the
group consisting of rotenone, pyrethrum, and nicotine.

Hunn (38), assignor to Stance, Inc., in United States patent 2,087,599,
issued July 20, 1937, applied for September 8, 1932, claims an insecticide
including water, a suitable oil and finely powdered natural parts af a plant
selected from the group consisting of derris and cube root containing an
inherent emulsifier and properties toxic to insects.

The following specific example is given of one way of carrying out
the invention. Spent pyrethrum flowers containing approximately 10 percent
oil residue extract from a previous extraction of the fresh flowers with oil
are pulverized and mixed with water in the proportion of 1 part of flowers
to 3 parts of water and about 2 percent of c-esylic acid (based on the whole
mixture) is added as a preservative. This -ixturc is, after proper agitation,
suitable as a stock emulsion which will be ready for use with mere dilution
with water. Ground derrie.or cube root can be satisfactorily used in a
composition similar to the above instead of the spent pyrethrum.

Simanton (93), assignor to the Gulf Research and Development Co.,
in United States patent 2,089,766, issued August 10, 1937, applied for March
7, 1936, claims:

11R ARY
STATES P1_W 30R






- 42 -


"An improved insecticide comprising in stable admixture
a petroleum fraction, a substance chosen from the class consisting
of ethylene glycol mor.oethyl ether acetate and diethylene glycol
monoethyl ether acetate, pyrethrins, and at least one of the active
toxic ingredients of derris and cube."

Chloroform and acetone are mentioned as solvents for rotenone. Among
the solvents that have been employed as blending agents in combination
with petroleum naphthas are: ethylene dicnloride, carbon tetrachloride,
acetone, camphor sassafras oil, benzol, and chloroform.

Diethylene glycol monoethyl ether acetate is miscible with a
petroleum oil having a viscosity of 100 sec. S. U. V. at 100 F. in
concentrations up to 5 percent. With a petroleum oil having a viscosity
of 200 sec. S. U. V. at 100 F. the same solvent is miscible in concentra-
tions up to 2 percent. Ethylene glycol monoethyl ether acetate is completely
miscible with both of the above oils. Either ethylene glycol monoethyl
ether acetate or diethylene glycol monoethyl ether acetate, if miscible
with a petroleum fraction in proportion of 1 percent or over, will hold in
stable solution toxic amounts of dr.:-ris extractives. Large proportions of
either solvent may be easily incorpor tted by admixture of light naphthas.

"I find that diethylene glycol monoethyl ether acetate is slightly
superior to ethylene glycol monoethyl ether acetate as a solvent for the
various extracts of derris and cube, but ethylene glyjcol monoethyl ether
acetate is miscible with the heavier petroleum fractions in larger propor-
tions than is diethylene glycol monoethyl ether acetate. Both compounds are
useful."

"Either of the new solvents of my invention is capable of holding
0.05 percent rotenone or other extracts of derris anrid cube in a petroleum
base insecticide when as little as 1 percent is blended with the petroleum
oil. Higher percentages will hold greater quantities of derris and cube
extracts in solution."

"To be effective as an insecticide, rotenone or other of the derris
or cube ext:Lcts mentioned should be present in the finished product in
concentrations ranging from ,01 to 0.1 per cent by weight."

Exar.plcs of this invention are:

"In one actual embodiment of the invention I prep-ared such a solution
by first fo --ing a 5 per cent solution of cry-stallin rotenone in diethylene
glycol monr.whyl ether acetate and then adding one part of this solution to
100 parts of a petroleum naphtha extract of pyrethrum flowers prepared by
extrocting 1.2 pounds pyrethrum flowers with a deodorized petroleum naphtha.
The resulting product was a stable, non-volatile, substantirn.lly odorless
solution of excellent insecticidal properties. When tested according to
the Peet-Grady method the solution repeatedly gave a knock down value of
98 and a kill of 85.

"In another embodiment of the invention I first prepared a crude
extract of dry derris roots by extracting the roots with acetone and







- 43 -


evaporating off the solvent to yield a resinous m'ss. I made a 5 percent
solution of, this resinous mass in dieth'ylene -Iycol monoethyl ether
acetate and preparrc -an insecticidal solution by adding 'ttwvo parts of this
5 per cent solution to 100 parts of a naphtha-pyrethrum extract prepared
as before. The resulting insecticidal solution when tested by the Peet-
Grady method gave a knock down of 98 and a kill of 88.

,y invention is also applicable to insecticides other than liquid
solutions. For instance, the invention is useful when incorporating
rotenone or other extracts of derris and cube in insecticidal salves.
In one such embodiment of my invention, I first blended 5 parts of a
concentrntcd naphtha solution of pyrethrins with one part of ethylene
glycol monoothyl ether acetate containing dissolved therein 5 percent of
total extractives prepared by extracting derris with acetbne and evapor-
ating off the solvent. I then incorporated this blend with 100 parts
of petrolatum b; melting the petrolatum, permitting it to cool, and adding
the blend while stirring just before the petrolatum became solid. The
resulting mixture was a stable odorless insecticide of salve-like homogeneous
consistency. This salve is useful for application to the ears of cattle
to kill ear ticks."

Coe (16), in United States patent 2,090,109, issued August 17, 1937,
applied for Iovember 15, 1933, claims

"A composition of matter comprising a suspension of a
powdered insecticide of plant origin subject to deterioration
by ordinary light, in a colored globule forming liquid of ad-
hesive tendency and non-repellent to insects, the color of the
globule forming liquid having a spectral transmission of above
4900 Angstrom units of the visible spectrum."

For example '. liquid gelatin is formed by dissolving the gelatin in
water. The resulting liquid gelatin is then colored with a water soluble
chlorophyll 6recn dye which may be made of thiocarmine blue and tartrazine
yellow. Powderud rotenone is then a ded to the chlorophyll green liquid
gelatin. The amount of rotenone to be used is &overned by the desired
toxic strength of the insecticide, and sufficient water is added to bring
the suspension to the desired consistency for spraying purposes.

The color screen may be formed of %n or, .go yellow dye, or the colors
above 4900 Ax..str3m units of the visible spectrum, although chlorophyll
green and orange yellow are preferable. A black piLment or opaque substance
may be used in forninq the color screen by the use of which all light is
excluded from the particles of the substance being protected.

Fawcett (25), assignor to Imperial Chemical Industries Ltd., in
United States patent 2,096,678, issued October 19, 1937, applied for October
25, 1935, in Great Britain October 29, 1934, makes essentially the same
claims as in British patent 446,576.






-44-


Donlan (20), assiemor to Stanco, Inc., in United States patent
2,096,885, issued October 26, 1937, .applied for October 21, 1933, claims
an insecticidal composition comprising as an active ingredient a sub-
stantial quantity of mineral oil of 300 to 600 F. boiling range
consisting predominantly of paraffinic hydrocarbons segregated from the
normally accompanying naphthenic hydrocarbons and added active Insecti-
cidal principles of vegetable origin, e.g., pyrethrum, cube, tuba, and
haiari.

Jones (52), in United States patent 2,103,195, issued. December
21, 1937, applied for July 3, 1937, dedicated to the free use of the
people of the United States of America, claims a new chemical combination
or rotenone and dichloroacetic acid having the empirical formula
C23H2206.02H202C12. He also claims a process for making-a chemical
compound of rotenone and dichloroacetic acid, which comprises essentially
dissolving an extract of plant material (e.g. Derris, Lornchocarpus,
Tephrosia) containing rotenone in dichloroacetic acid, adding water and
separating the resulting crystalline product. Reference is made to the
addition compounds of rotenone with aketic acid, propionic acid and alpha-
chloropropionic acid in each of which the molecular ratio is two mols of
rotenone to one mol of acid.

0'Kane (80), in United States patent 2,104,757, issued January 11,
1938, applied for May 31, 1934, claims as an insecticidal agent, a
substantially nonaqueous combination of an oil selected from the class
consisting of vegetable and animal oils, a contact insecticide selectively
soluble in said oil, and an emulsifying agent soluble in said contact
agent in proportions to give an unstable dispersion in water.

Among the insect poisons, a wide variety of materials may be in-
cluded, and particularly exemplifying the nerve poisons or contact in-
secticides, there may be mentioned the extracts of pyrethrum flowers,
and other oil-soluble extracts, such as those of derris root, cube root,
or oil-soluble nerve poisons, such as the active principle of strychnia,
as well as synthetic chemicals including various amine derivatives.

Patents Cited

1. ADAMViS, E. W.

1934. Mothproofing composition. Canadian Patent 338,896; issued
January 23, 1934; applied for October 23, 1931.

2. BADERTSCHER, A. E.

1933. Horticultural spray. U. S. Patent 1,938,652; issued
December 12, 1933; applied for August 20, 1931.
3.

1933. Method of preparing horticultural dust. U. S. Patent 1,940,899;
issued December 26, 1933; applied for January 21, 1932.







- 45 -


4. BAGITALL-BULL, E.

1924. Improvmcrnts relating to insecticides, vermifuges, sheep
dips and the like. British Patent 214,822; issued May 1,
1924; applied for April 16, 1923.

5. ---

1925. Insecticide, vermifuge, sheep dip, and the like. U. S.
Patent 1,522,041; issued January 6, 1925; applied for
July 22, 1924.

6. BOEHRIiTGER, C. H.

1934. Japanese firm claims new process of obtaining toxic substances
from derris. U. S. Dept. Corn., Bur. Foreign and Dom. Corn.,
Economic and Trade Notes no. 310. Rept. from the Asst.
Trade Commissioner, Sir.Capore, S. S., dated March 8, 1934.

7. BOOTH STEAL'SHIP CO. LTD., and WA2D, H. G.

1935. Improvements in or relating to the extraction of toxins from
roots for the manufacture of insecticides. British Patent
437,171; issued October 24, 1935; applied for March 30, 1935.

8. ----

1936. Perfectionnements a l'extraction des toxines, pour la fabrica-
tion d'insecticides, de racines. French Patent 794,206; issued
February 11, 1936; applied for August 27, 1935; in England
March 30, 1935.

9. -----

1937. Verfahren zur Herstellung von fur die Insektenvertilgung
verwendbaren Auszugen aus Rotenon enthaltenden Wurzeln.
German Patent 646,570; issued June 17, 1937; applied for
September 11, 1935.

10. BOUSQUET, E. W.

1935. Contact insecticide. U. S. Patent 2,006,227; issued June 25,
1935; applied for October 19, 1932.

11-. ------- and TISDALE, W. H.

1934. Contact insecticide. U. S. Patent 1,954,517; issued April
10, 1934; applied for July 8, 1932.

12. BUC, H. B.

1935. Insecticidal oil. U. S. Patent 2,013,028; issued September
3, 1935; applied for March 12, 1931.







- 46 -


13. BUC, H. E.

1936. Insecticide. U. S. Patent 2,042,296; issued May 26, 1936;
applied for March 12, 1931.

14. CHEMISCHE FABRIK MARIEN1ELDE G.m.b.H.

1935. Improved manufacture of derris root extracts and other
plant extracts. British Patent 432,626; issued
July 30, 1935; applied for January 11, 1935; in
Germany, January 18, 1934.

15. CHROMEK, F.

1937. Aus rotenon oder tubatoxin enthaltendcn pflanzonwurzeln
hergestelltes insektenbekimpfungsmittel. German Patent
643,804; issued April 17, 1937; applied for February 7,
1932.

16. COE, M. R.

1937. Stabilized insecticide of plant origin. U. S. Patent
2,090,109; issued August 17, 1937; applied for
November 15, 1933.

17. DENNIS, W. J.

1927. Vermifuge and insecticide. U. S. Patent 1,621,240; issued
March 15, 1927; applied for April 16, 1923.

18. ----

1932. Vermifuge and insecticide. U. S. Patent Re. 18,667; issued
November 22, 1932; applied for February 25, 1929.

19. -----

1929. Insecticide and vermifuge. Canadian Patent 293,233; issued
September 24, 1929; applied for March 12, 1929.

20. DONLAN, T. R.

1937. Insecticide. U. S. Patent 2,096,885; issued October 26,
1937; applied for October 21, 1933.

21. DOUGHERTY, L. B., and ANDERSON, W. J.

1934. Vermin destroyer. U. S. Patent 1,963,838; issued June 19,
1934; applied for May 23, 1933.






- 47 -


22. DOW, H. H., anrd HALE, W. J.

1924. Insecticidal compound. U. S. Patent 1,514,377; issued
November 4, 1924; applied for March 31, 1920; assigned
to the Dow Chemical Co.

23. DUPEE ET CIE

1934. Produit insecticide. French Patent 769,445; issued
August 25, 1934; applied for February 28, 1934.

24. EICHHORN, X.

1936. Verfahren zur Herstellung eines derrisextrakthaltigen
insektenbekimpfungsmittels. German Patent 630,483;
issued May 28, 1936; applied for November 22, 1932.

25. FAWCETT, E. W.

1937. Process of producing rotenone and associated substances
from natural sources containing the same. U. S. Patent
2,096,678; issued October 19, 1937; applied for October
25, 1935; assigned to Imperial Chemical Industries, Ltd.

26. ---.--. and IMPERIAL Ch MICAL INDUSTRIES, LTD.

1936. Process of producing rotenone and associated substances
from natural sources containing the same. British
Patent 446,576; issued April 29, 1936; applied for
October 29, 1934.

27. FRYER, P. J.

1926. Insecticide, sheep dip, and the like. U. S. Patent
.1,583,681; issued May 4, 1936; applied for November
29, 1924.

28. FULTON, S. C.

1934. Insecticide. U. S. Patent 1,967,024; issued July 17,
1934; applied for June 6,. 1929.

29. GOLDSCHMIDT, S., and MARTIN, K.

1936. Insecticide. Canadian Patent 357,959; issued May 19,
1936; applied for December 17, 1934; in Germany
December 27, 1933.

30. GRAAFLAND, A. J. N., and NELLENSTEYN, F. J.

1931. Antifouling composition. British Patent 362,526; issued
December 10, 1931; applied for September 10, 1930; in
Holland, September 12, 1929.






- 48 -


31. GRAITT, D. H. :

1929. Insecticide. Canadian'Patent 333,642; issued June 27,
1933; applied for October 25,i:1929.

32. ----

1933. Insecticide. U. S. Patent 1,934,057; issued November 7,
S1933;W applied for October- 31,- 1928; assigned to-
*Standard>Oil Development Co.. -;. '

33. -- i' t .. '

1933. Insecticide 'and process of making the same;:U. S. Patent
1,940,646; issuedtDecember 19, 1933; applied for October
S19, 1927; assigned to Standar4 Oil-Development Co.

34. CALLER, H. L. J. and SCHAFFER, P. S. .**:;

1934; Process of preparing, dihydrorotenone. e'U. S. Patent
1,945,312; issued January .30, 1934-"apTplied for April
10, 1933. : ,

35. HAMILTON, C. C.

1936. Insecticide. U. S. Patent 2,030,584; issued February 11,
... 1936; applied for June 5, 1934. 7. ; "

36. -----.. ,

1936. Insecticide composition. U. S. Patent 2,035,546; issued
March 31, 1936; applied for May 14, 1932. -

37. HOFFMANN, F.-LA ROCHE ANI) QO.. ;... ''

1926. Schadlingsbeka*pfungsmittel. Swiss Patent 124,290; issued
January 16, 1928; applied for October 5, 1926.

38. HUNN, E. B.

1937. Horticultural oil spray. U. S. Patent .2,087,599; issued
July 20, 1937; applied for September 8, 1932.
... . .. ;
39. I. G. FARBENINDUSTRIE A. G.

1932. Improved prcparatibns for killing flies. .British Patent
377,069; issued July 21, 1932; applied for November 27,
1931; in Germany, ITovember 27, 1930.

40.

1932. Fliegenvertilgungsmittel. German Patent 555,117; issued
July 18, 1932; applied for November 28, 1930




- 49 -


41. I. G. FARBENTINDUSTRIE A. G.

1932. Improved process for killing or eliminating flies and
preparations therefore. British Patent 378,300; issued
August 11, 1932; applied for December 12, 1931; in
Germany, December 13, 1930.

42. IIBA, T., and NAKATIUKA, S.

1931. Insecticide. Japanese Patent 91,478; issued May 20, 1931;
[Abstract in Chem. Abs. 26;1703. 1932.]

43. IM&AI, Y.

1931. Insecticide. Japanese Patent 91,645; issued June 3, 1931;
[Abstract in Chem. Abs. 26;1703. 1932.]

44. IMPERIAL CHEMICAL INDUSTRIES, LTD.

1936. Procede de fabrication de la rotenone et des substances
associees en partant des products naturels qui en
contiennent. French Patent 797,052; issued April 20,
1936; applied for October 29, 1935; in England,
October 29, 1934.

45. IMPERIAL CHEMICAL INDUSTRIES OF AUSTRALIA AND :IEW ZEALAiD LTD.

1936. Improvements in or relating to the protection of sheep
and cattle from infestation by insects. Australian
Patent 20,894/35; issued February 14, 1935; applied for
January 11, 1935.

46. IMPERIAL CHEMICAL INDUSTRIES, LTD.

1937. Rotenone production. Canad. patent 369,499; issued
October 26, 1937; applied for October 28, 1935.
Assignee of E. W. Fawcett.

47. ISIHARA, T.

1931. Insecticide. Japanese Patent 91,875; issued June 20,
1931; [Abstract in Chem. Abs. 26;1703. 1932.].

48. JAMES, J. H.

1935. Manufacture of insecticides and fungicides. U. S. Patent
2,006,456; issued July 2, 1935; applied for March 12,
1930.

49. JO1ES, H. A.

1933. Insecticide and process for making the same. U. S. Patent
1,928,256; issued September 26, 1933; applied for August
23, 1930.





- 50 -


50. ------

1933. Process for making an insecticide. U. S. Patent 1,928,968;
issued October 3, 1933; applied for August 23, 1930.

51. ----

1934. Process of extracting rotenone from plant material. U. S.
Patent 1,942,104; issued Januarj 2, 1934; applied for
February 20, 1933.

52.

1937. Insecticide. U. S. Patent 2,103,195; issued December 21,
1937; applied for July 3, 1937.

53. KILGORE, L. B.

1937. Insectifuge and insecticide. U. S. Patent 2,070,603;
issued February 16, 1937; applied for January 3, 1936.

54. LELE'-TS, G. J., and F:CfER, P. J.

1917. Tr2-.rovements relating to insecticides, sheep dips, animal
washes and the like- British Patent 105,525; issued
April 19, 1917; applied for December 4, 1916.

55. anid FRYER, P. J.

1920. Mlittel zur vertilgung von insekten und sonstigen auf
tieren oder pflanzen wohnondcrn parasiten. German Patent
321,317; issued May 29, 1920; applied for December 21,
1916.

56. ------ and FILVER, P. J.

1920. Mittel zur vertilgung von insekten und sonstigen auf
tieren oder pflanzen wohnenden parasiten. Germrn Patent
327,583; issued October 11, 1920; applied for December
22, 1916.

57. LIiJC-LE, J.

1931. Method of fumigating with calcium cyanide. U. S. Patent
I1,-20,394; issued August 25, 1931; applied for liarch
9, 1929; in Germany, March 12, 1928.

58. McDOUGALL, I., and HOtTLES, F.

1923. Improvements in the manufacture of insecticides, sheep dips,
vermifuges and the like, British patent 226,250; issued
December 23, 1924; applied for June 23, 1923.






- 51 -


59. ---- and HOLE0S, F.

1924. Improvements in the manufacture of insecticides, sheep
dips, vermifuges and the like. Australian Patent
18,227; issued November 10, 1924; applied for June 16,
1924.

60. ------- and H0WiLES, F.

1925. Improvements relating to insecticides. British Patent
233,857; issued May 21, 1925; applied for April 15,
1924.

61. ---: and HOWLES, F.

1925. Insecticide, sheep dip, vermifuge, etc. Canadian Patent
247,627; issued March 17, 1925; applied for lMay 22, 1924.

62. ------- and HO7LES, F.

1925. Perfectionnements dans la fabrication d1 insecticides, de
bains pour moutons, de vermifuges et de preparations
similaires. French Patent 589,969; issued June 9, 1925;
applied for May 14, 1924.

63. McDOUGALL, I. S., McDOUGALL, I., and H'cDOUGALL, S.

1912. Improvements relating to insecticides, sheep dip, vermifuges,
and the like. British Patent 3,204 of 1911; issued May
8, 1912; applied for February 8, 1911.

64. ----McDOUGALL, I., and McDOUGALL, & .;

1912. Improvements relating to insecticides, sheep dip, vermifuges
and the like. British Patent 8,322; issued December 19,
1912; applied for April 6, 1912.

65. -------- McDOUGALL:,, I., and McDOUGALL, S.

1912. Improvements relating to insecticides, sheep dips, vermifuges
and the like. British Patent 10,215; issued :.ay 28, 1912;
applied for April 27, 1911.

66. ------- McDOUGALL, I., and :'IcDOUGALL, S.

1913. Insecticide, sheep-dip, vermifuge, etc. U. S. Patent
1,065,156; issued June 17, 1913; applied for September 8,
1911

67. McDOUGALL AND YALDING (LTD.)

1925. Insecticide, sheep dips and the like. Canadian Patent
253,319; issued September 1, 1925; applied for ITovember
26, 1924.








68.. McDOUGALL and YALDING (LTD.)

1925. Perfectionneaents aux insecticides, aux bains pour moutons
et aux substances similaires. French Patent 589,506;
issued May 30, 1925; applied for November 22, 1924.

69. -- and YALDING (LTD.), and FRYER, P. J.

1925. Improvements in insecticides, sheep dips, and the like.
S British Patent 229,773; issued March 2, 1925; applied
for December 1, 1923.

70. ------- and YALDING (LTD.) and FRYER, P. J.

1926. Improvements in insecticides, sheep dips and the like.
British Patent 246,252; issued January 28, 1926; applied
for November 12, 1924.

71. ------- and YALDING (LTD.) and FRYER, P. J.

1927. Improvements in insecticides, sheep dips and the like.
British Patent 280,256; issued November 17, 1927; applied
for November 24, 1926.

72. McGILL, W. J.

1932. Mothproofing. U. S. Patent 1,854,948; issued April 19, 1932;
applied for November 7, 1927.

73. ----

1934. Mothproofing composition. Canadian Patent 33L9, '"issued
January 23, 1934; applied for April 1, 1932; assigned to
Standard Oil Co.

74. MIKESKA, L. A.

1936. Insecticide and insect repellent and mu'o3 of ':aicing the
same. U. S. Patent 2,066,184; issued December 29, 1936;
S.' .applied for October' 29, 1932.

75. MIILLS, L. E. and FAYERWEATEZR, B. L.

1934. Tertiary alkyli substituted orthodihydrojybenzenes. U. S.
.Patent 1,942,827; issued January 9, 1934; applied for
*"i March 27, 1933. :
t * '
76. NETTAI SANGYO KABUSHIKI KAISHA

1926. A new or improved process for obtaining insecticidal or
other toxic substances from plants of the derris species.
British Patent 247,140;- issued August 5, 1926; applied for
June 25, 1925; in Japan, February 4, 1925.


*" l_ ^ *






- 53 -


77. ----

1930. Werkwijze voor het bereiden van een-insecticide, dat een
v.'erkzaam bestanddeel van derrissoorten bevat, verkregen
door extractie met organische oplosmiddelen. Dutch Patent
21,841; issued May 15, 1930; applied for February 10, 1926.

78. OHORI, T., and NAKAZAWA, K.

1930. Process for producing a liquid insecticide containing
effective ingredient of derris.species. U. S. Patent
1,745,907; issued February 4, 1930; applied for February
10, 1928; in Japan, February 18, 1927; assigned to Zaiden
Hojin Rikagaku Kenkujo, Tokyo, Japan,.

79. 0'KAME, W. C.

1930. Fungicide and insecticide. U. S. Patent 1,786,125; issued
December 23, 1930; applied for May 18, 1927.

80.

1938. Insecticide spray. U. S. Patent 2,104,757; issued January
11, 1938; applied for May 31, 1934.

81. PFAFF, K. and DUNKEL, M.

1934. Insecticidal agent. Canadian Patent 345,383; issued October
16, 1934; applied for December 12, 1931; in Germany,
December 13, 1930.

82. RIEDEL-E. DE HAEN, J. D., A.-G.

1933. Procede dlaneantissement de la vermine, en particulier
d'insectes. French Patent 778,844; issued March 25, 1935;
applied for September 24, 1934; in Germany, September 30,
and November 8, 1933.

83. RYAN, V. H., and MORAIT, J. A.

1936. Preparation of insecticides. U. S. Patent 2,043,267; issued
June 9, 1936; applied for October 2, 1933.

84. SANDERS, G. E.

1931. Process of forming colloidal suspensions containing copper
and product thereof. U. S. Patent 1,803",870; issued May
5, 1931; applied for October 3, 1927.

85. ----

1932. Method of making insecticides floatable. U. S. Patent
1,847,540; issued March 1, 1932; applied for March 11, 1930.







- 54 -


86. SANKOWSKY, N. A.

1936. Insecticides containing derris extracts and methods of
preparing the same. U. S. Patent 2,058,832; issued
October 27, 1936; applied for March 17, 1933.

87. ------- and FULTON, S. C.

1934. Insecticide. Canadian Patent 340,315; issued March 20, 1934;
applied for December 24, 1931; in the United States
January 5, 1931.

88. SCHOTTE, H. and GORNITZ, K.

1935. Insecticide. Canadian Patent 348,379; issued February 26,
1935; applied for January 24, 1934.

89. ------- and GORNITZ, K.

1935. Insecticide. Canadian Patent 348,380; issued February 26,
1935; applied for January 24, 1934.

90. ------- and GOPITZ, K.

1935. Insecticidal preparation. U. S. Patent 2,024,392; issued
December 17, 1935; applied for December 12, 1933; in
Germany, November 13, 1931.

91. SESSIONS, A. C.

1937. Parasiticidal composition. U. S. Patent 2,083,098; issued
June 8, 1937; applied for April 4, 1934; assigned to
California Spray-Chemical Corp.

92. SHELL DEVELOPMENT COMPANY

1937. Insecticide. Canad. Patent 369,390; issued October 19, 1937;
applied for December 24, 1936; in United States, January 6,
1936.

93. SIiiIA.ITON, W. A.

1937. Insecticide. U. S. Patent, 2,089,766; issued August 10, 1937;
applied for March 7, 1936.

94. SMITH, L. E.

1936. Insecticide. U. S. Patent 2,049,725; issued August 4, 1936;
applied for March 20, 1935.







- 55 -


95. STANDARD OIL DEVELOPMENT COMPANY

1931. Improved insecticidal, insect-repelling and fUngicidal
compositions. British Patent 350,397; issued June 15,
1931; applied for February 15, 1930.

96. --------SAI KOWSKY, N. A., and FULTON, S. C.

1933. Improvements in or relating to insecticides. British Patent
394,977; issued July 4, 1933; applied for January 4, 1932;
in the United States, January 5, 1931.

97. STEINDORFF, A., PFAFF, K., KRI aER, R., and KERN, H.

1931. Mittel sur bekampfung von musciden und sonstigen insekten.
German Patent 564,018; issued November 12, 1932; applied
for July 5, 1931.

98. TAKEI, S.

1929. Process for producing a liquid insecticide containing
effective ingredient of derris species. U. S. Patent
1,724,626; issued August 13, 1929; applied for August 31,
1925; in Japan, September 8, 1924.

99. VOOPHEES, V.

1935. Light stable insecticide. U. S. Patent 2,011,428; issued
August 13, 1935; applied for May 4, 1931; assigned to
Standard Oil Co., of Indiana, Chicago, Ill.

100. WARD., H. G.

1936.. Extraction of toxins from roots for the manufacture of
insecticides. U. S'. Patent 2,056,438; issued October 6,
1936; applied for September 4, 1935; in Great Britain
March 30, 1935.

101. ----

1936. Insecticide extraction. Canad. Patent 362,903; issued
December 22, 1936; applied for August 29, 1935; in
Great Britain March 30, 1935.

102. WII:STRO14, E. G. A.

1935. Insecticide and method of producint the same. British
Patent 434,660; issued September .6, 1935; applied for
March 19, 1934.






- 56 -


103.


1936. Insektd6daride medel." Swedish Patent 86,063; issued April
15, 1936; applied for March 16, 1934.


104.


1936. Iisektd6dande medel. Swedish -Pateant. 87,625; issued October
13, 1936; applied .for March '-16, 1934.

105. WOTHERSPOON, R. "

1935. Process for producing water-soluble and water miscible
insecticides and products produced thereby. 11. S. Patent
2,052,374; issued August 25, *1935; applied for April 28,
1934.

106. ,

1936. Insecticidal solution. U. S. Patent 2,058,200; issued
October 20, 1936; applied for September 12, 1932.

107. ZAIDAN HOJIN RIKAGAKU I.ENJTUJO


1926. A






1928. A


process for producing a liquid insecticide containing
effective ingredient of derris species. British
Patent 239,483; issued May 6, 1926; applied for April
24, 1925; in Japan, September 8, 1924.



process for producing a liquid insecticide containing
effective ingredient of derris species. British .
Patent 285,797; issued November 29, 1928; applied for
February 20, 1928; in Japan, February 18, 1927.


109. ----

1928. Ins'ectici'des. British Patent 300,606; applied for July
17, 1928; in Japan November 16, 1927; not yet accepted.
Illus. Offic. Jour. No. 2086, 6904 (1929). (Reproduced
by permission of the Controller of His Britannic
Majesty's Stationery Officer).


110. ----


1929. Powdered insecticide containing actiVe ingredients of
roots of.derris species. Australian, Patent 15,327/28;
issued July 24, 1929; applied for August 28, 1928; in
Japr-n, November 16, 1927.


108.





- 57 -


Junior Patentees Index


Anderson, W. J.; see Dougherty, L. B.
Dunkel, M.; see Pfaff, K.
Fayerweather, B. L.; see Mills, L. E.
Fryer, P. J.; see Lemmens, G. J.
Fryicr, P. J.; see McDougall and Yalding (Ltd.)
Fulton, S. C.; see Sankowsky, N. A.
Fulton, S. C.; see Standard Oil Development Company
G6Ornitz, K. ; see Schotte, H.
Hale, W. J.; see Dow, H. H.
Howles, F.; see McDougall, I.
Imperial Chemical Industries, Ltd.; see Fawcett, E. W.
Kern, H.; see Steindorff, A.
Kramer, R.; see Steindorff, A.
Martin, K.; see Goldschmidt, S.
McDougall, I.; see McDougall, I. S.
McDougall, S.; see McDougall, I. S.
Moran, J. A. see eyan, V. H.
Nakatuka, S. see liba, T.
iJaKazawa, K. ; see Ohori, T.
ITellensteyn, F. J.; see Graafland, A. J. N.
Pfaff, K.; see Steindorff, A.
Sankowsky, N. A.; see Standard Oil Development Company
Schaffer, P. S.; see Haller, H. L. J.
Tisdale, W. H.; see Bousquet, 2. W.
Ward, H. G.; see Booth Steamship Co., Ltd.

Assignee Index

C. B. Byrnes, Trustee; see James, J. H.
California Spray-Chemical Corp.; see Sessions, A. C.
Derris, Inc.; see Wotherspoon, R.
Deutsche Gesellschaft fur Schadlingsbekampfung M.B.H. of Frankfort-on-the
Germany; see Lingler, J.
Dow Chemical Co.; see Dow, H. H. and Hale,-W. J.
Dow Chemical Co.; see Mill, L. E. and Fayerweather, B. L.
E. I. du Pont de :;emours & Co., see Bousquet-E. W. and Tisdale, W. H.
Endowment Foundation of New Brunswick, N. J. ; see Hamilton, C. C.
Grasselli Chemical Company; see Bousquet, E. W.
Gulf Research and Development Company; see Simanton, W. A.
Imperial Chemical Industries, Ltd.; see Fawcett, E. W.
International Hydrogenation Patents Co., see Pfaff & Dunkel.
Kessler Chemical Corp.; see Goldschni idt, S. and Martin, K.
McCormick & Co., Inc.; see Badertscher, A. E.
1cDougall & Yalding, Ltd.; see Fryer, P. J.
Schering-Kahlbaum, A. G. of Berlin, Germany; see Schotte, H. and G6rnitz, K.
Stanco, Inc.; see Donl'an, T. R.
Stanco, Inc.; see Hunn, E.. B.
Stanco, Inc.; see Sankowsky, N. A. '
Standard Oil Company of Indiana; see Voorhees, V.





- 58 -


Standard Oil Development Company; see Adams, E. W., Bu-ac, H. E., Grant, D. H.,
McGill, W. J., Mileska, L. A., Sankowsky, N. A. and Fulton, S. C.
Yates, W. J.; see Shell Development Co., Ltd. :
Zaiden Hojin Rikagaku Kenkujo; see Ohori, T. and !akazawa, 'K.

Diluents

Agar-agar, U. S. 1,928,968
Albumin, animal, Brit. 239,483; U. S. 1,724,626
Alcohol, Swiss, 124,290
Alcohols, higher, Brit. 239,483, 285,797; Dutch 21,841; U. S. 1,724,626,
1,940,646
Alkaline earth cyanide, U. S. 1,820,394
Alkylolamines, U. S. 2,043,267
Ammonium compounds -
alginate, U. S. 1,928,968
linoleate, Brit. 280,256; Ger. 643,804
oleate, Brit. 280,256
sec-Amyl alcohol, U. S. 1,940,646 '
Amyl salicylate, Ger. 555,117
Anthreaquinone, 1,4-toluido, U. S. 2,011,428
Antioxidant, U. S. 2,030,584
Antiseptic agent, U. S. 1,065,156, Brit. -3,204/1911
Aryl compounds, substituted, Can. 3609,30 0.
Bean milk, Brit. 239,483; U. S. 1,724,626' '
Bean oil, Brit. 239,483; U. S. 1,724,626'
Beeswax, Brit. 239,483; Dutch 21,841; U. S. 1,724,626
Bentonite, Austral. 20,894/35; U. S. 1,928,968, 19940,899, 2,030,584,
2,052,374
Benzene, dichloro, U. S. 1,940,646 ....
Benzoic acid esters, Canad. 345,383
Benzoic acid ethers, Canad. 345,383
Benzyl alcohol, U. S. 1,514,377 ....
Bordeaux mixture, Brit. 246,252; U. S. 1,583,681, 1,803,870
sec-Butyl alcohol, U. S. 1,940,646
Calcium arsenate, U. S. 1,514,377
Calcium carbonate, Austral. 15,327/28
Calcium caseinate, U. S. 1,803,870, 1,928,968
Camphor oil, Brit. 239,483; Japanese 91,645 .
Casein, Brit. 246,252; U. S. 1,583,681, 1,803.,870
Castor oil Brit. 23S,483; U. S. 1,724,626
sulphonated, Brit. 229,773; Canad. 253,319; French 589,506; U. S.
1,583,681
Catechol, U. S. 2,052,374 .
Cement, hydraulic Brit. 362,526
Chalk, U. S. 2,052,374 .
Chloresterinozonide, Swiss 124,290
Chrysanthemum (Pyrethrum), U. S. 1,940,899, 2,066,184 .
Chrysanthemum extract, Brit. 434,660; Canad. 369,390 :.
Clay, colloidal, U. S. 2,030,584, 2,035,546
Clays, U. S. 2,052,374, Austral. 15,327/28







- 59 -


Cocoanut oil, Brit. 239,483
Cocoanut oil soap, U. S. 2,058,200
Coconut oil, Dutch 21,841; U. S. 1,724,626
Codliver oil, Brit. 239,483; Dutch 21,841; U. S. 1,724,626
Colloids, clay, U. S. 2,030,584, 2,035,546
Copal, Brit. 239,483; Dutch 21,841; U. S. 1,724,.626
Copper-calcium silicate, U. S. 2,083,098
Copper, colloidal, U. S. 1,803,870
Copper oxide, U. S. 1,786,125
Cornstarch, U. S. 1,621,240
Cresol, U. S. 2,011,428; 2,087,599
Cresols, U. S. 1,940,646
Cube, U. S. 1,940,899
Cyclohexanol, U. S. 1,940,646
Cyclohexanol homologues, U. S. 1,940,646
Dextrin, Dutch 21,841; U. S. 2,052,374, 2,058,200
Dextrine, Brit. 239,483; U. S. 1,724,626
Dipentene, U. S. 1,938,652
Egg albumin, Brit. 239,483; U. S. 1,724,626
Egg white, Dutch 21,841
Ethane, hexachlore, Ger. 643,804
Ethanolamine soap, U. S. 2,030,584
Ether, beta, beta dichlorodiethyl, U. S. 1,954,517
Ether, diphenvl, Brit. 377,069; Ger. 555,117
Fats, Brit. 239,483, 285,797; Dutch 21,841; UJ. S. 1,724,626
Fatty acids higher, 3rit. 239,483, 285,797; Dutch 21,841; U. S. 1,724,626
Flour, U. S. 2,052,374
Gelatin, U. S. 1,928,968
Glucose, U. S. 2,058,200
Glue, Brit. 239,483, 280,256; Dutch 21,841; U. S. 1,724,626, 2,052,374
Glue, Bengal fish, Dutch 21,841
Glycerol, Brit. 239,483; Dutch 21,841; U. S. 1,724,626
Gum U. S. 2,052,374
Gum acacia, U. S. 1,928,968, 2,058,200
Gum arabic, U. S. 1,745,907
Gum tragacanth, U. S. 2,058,200
Gums -
ghatti, U. S. 1,928,968, 2,011,428, 2,058,200
karaya, U. S. 1,928,968, 2,058,200
Halowax oil, U. S. 2,013,028
Hard oil, Dutch 21,841; U. S. 1,724,626
Hardened plant oils, Dutch 21,841
H-drocarbons -
higher, Brit. 285,797, 239,483; Dutch 21,841; U. S. 1,724,626
non-volatile, highly halogenated, U. S. 2,013,028
sulphonated, U. S. 2,052,374
Hydrogenated animal oil, Brit. 239,483
Hydrogenated vegetable oil, Brit. 23Q,483
Hydroxyquinol, U. S. 2,052,374
Isinglass, bengal, Brit. 239,483; U. S. 1,724,626





- 60 -


Isopropyl alcohol, U. S. 1,940,646
Isothiocyanate, aromatic, Canad., 357,959
Kaolin, U. S. 2,024,392
Ketones, U. S. 1,940,646
Kieselguhr, U. S. 1,928,968, 2,052,374
Lard, Brit. 239,483; U. S. 1,724,626 -
Lead arsenate, Brit. 246,252; U. .S. 1,514,377; 1,583,681, 2,066,184
Lecithin, soybean, U. S. 2,006,227
Lime, U. S. 1,514,377, 1,847,540
Lime sulphur solution, Brit. 246,252; U. S. 1,583,681
Linseed oil, Dutch 21,841
Lithopine, U. S. 1,928,968
Magnesium arsenate, U. S. 1,514,377
Magnesium cyanide, U. S. 1,820,394
Methyl salicylate, Ger. 643,804
Mineral oil U. S. 2,030,584
I:ineral oil, sulprhonated, U. S. 1,940,646
Molten carrier, Canad. 348,380
Naphthalene, Jap. 91,645
iTaplthalene, chloro, U. S. 1,940,646
Naphthalene, halogenated, U. S. 2,013,028
Nicotine, Brit. 233,857; U. S. 2,066,184
Oil, U. S. 2,087,599
Oil, animal, Dutch 21,841; U. S.' 1,724,626, 2, 030,584
Oil, animal, hydrogenated, Brit. 239,482
Oil, fatty sulphonated, French 589,506; Canad. 253,319
Oils Brit. 239,483, 285,797; Dutch '21,841; U. S. 1,724,626, 2,030,584
chrysalis, Brit. 239,483; Dutch 21,841; U. S. 1,724,626
ethereal, chlorinated, Brit. 434,660; Swedish 86,083
ethereal, sulphonated, Brit. 434,660; Swedish 86,083-
fish, Brit. 239,483, 285,797; Dutch 21,841; U. S. 1,724,626, 1,745,907
hardened plant, Dutch 21,841
essential, U.. S. .1,854,948
herring, Brit. 239,483; Dutch 21,841; U. S. 1,724,626
hydrogenated, Brit. 239,483
lemon, Brit. 239,483
pine, U. S. 1,938,652, 1,940,646
pine, steam distilled, U. S. 1,940,646
plant, Dutch 21, 841
rape, Brit. 239,483; Dutch- 21,841; U, S. .1,724,626
rapeseed, Brit. 239,483; Dutch 21,841; U. S. 1,724,626
sassafras, French 769,445
sardine, Brit. 239,483; Dutch 21,841; U. S. 1,724,626

shark oil, Brit. 239,483; Dutch 21,841; U. S. 1,724,626
sulphonated, U. S.- 2,052,374, 1,940,646, 1,583,681
vegetable, Dutch 21,841; French 769,445; U. S. 1,724,626; 2,030,584
vegetable hard, U. S. 1,724,626'
vegetable hydrogenated, Brit. 239,483
vegetable sulphonated, U. S. 1,940,646
whale, sperm, Canad. 253,319; French 589,506; U. S. 1,583,681




- 61 -


Paraffin, Brit. 239,483; Dutch 21,841; U. S. 1,724,626
Paraffin wax, sulphonated, Canad. 253,319; French 589,506; U. S. 1,583,681
Peanut oil, French 769,445
Potrolatum, U. S. 2,089,766
Petroleum -
fractions, sulphonated, U. S. 2,006,456
sulfonates, U. S. 1,934,057
sulphuric soap acid, Brit. 350,897
white oil, Brit. 350,897
Phenols, U. S. 1,940,646, 2,030,584
Phenols, dihydric, U. S. 2,052,374
Phenols, trihydric, U. S. 2,052,374
Phenyl salicylate, Ger. 555,117
Phloroglucinol, U. S. 2,052,374
Phytosterinoxide, Swiss 124,290
Pine resin, Brit. 239,483; Dutch 21,6.41; U. S. 1,724,626
Potassium oleate, U. S. 1,928,968
Protein, animal, Dutch 21,841
Pyrethrins, U. S. 1,967,024, 2,058,200, 2,089,766
Pyrethrum, U. S. 1,940,899, 2,066,184
Pyrethrum, extract, Brit. 434,660, Canad. 369,390
Pyrogallol, U. S. 2,052,374
Quassia extract, Brit. 434,660; French 769,445
Quinol, U. S. 2,052,374
Resins, Brit. 285,797; 239,483; Dutch 21,841; U. S. 1,724,626
Resorcinol, U. S. 2,052,374
Rolin soap, Brit. 350,897; U. S. 1,934,057, 1,940,646
Sabadilla seeds, Canad. 348,379; U. S. 2,024,392
Saponin, Brit. 350,897; U. S. 1,928,968; 1,934,057, 2,058,200, 2,066,184
Siliceous earth, U. S. 1,940,899
Soaps Brit. 239,483, 285,797; 434,660; Dutch 21,841; Swedish 86,083; U. S.
1,621,340, 1,724,626, 1,745,907, 1,934,057, 2,052,374, 2,058,20
Soaps, fatty, U. S. 1,934,057
Soaps, fatty acid, Brit. 350,897
Soaps, fish oil, U. S. 2,066,184
Soaps, oil-soluble sulphonated, U. S. 2,066,184
Soaps, potassium, U. S. 2,030,584
Soaps, petroleum sulphonic acid, Brit. 350,897
Soaps, resin, Brit. 432,626, 434,660
Soaps, sodium, U. S. 2,030,584
Soaps, soft, Brit. 437,171; U. S. 1,065,156, 2,056,438
Soaps, sulphonated vegetable oil, U. S. 1,934,057
Sodium carbonate in mfg. extract, U. S. 2,056,438
Soy bean -
milk, Dutch 21,841
oil, Dutch 21,841
Starch, Brit. 239,483; Dutch 21,841,-U. S. 1,724,626, 1,928,968, 2,052,374,
2,058,200
Stearic acid, U. S. 1,847,540
Sucrose, U. S. 2,058,200
Suet, hog, Dutch 21,841





- 62 -


Sulphonated alcohols-, U. S. 2,052,374
Sulphonria.ted animal oil soaps, U. S. 1,934,057
Sulphonated fatty body, U. S. 1,583,681
Sulphonated oil soluble, U. S. 1,940,646
Sulphur, U. S. 1,065,156
Talc, U. S. 1,940,899, 2,024,392, 2,052,374
Talcum powder, U. S. 1,621240
Tallow, beef, Brit. 239,483; Dutch 21,841; U. S. 1,724,626
Tanrnicfid, U. S. 1,928,968, 2,030,584
Terpineol, U. S. 1,940,646
Triethanolamine, Brit. 434,660
Triethanolamine, oleate, French 769,445; U. S. 1,928,968, 2,043,267, 2,058,200C
Turkey red oil, U. S. 1,940,646
Turpentine, Japanese, 91,645
Urethanes Ger. 564,018
substituted, Ger. 564,018
Veratrin, Can. 348,379; U. S. 2,024,392
Water softening agent, U. S. 1,065,156, Brit. 3204/1911
Waxes, Brit. 239,483, 285,797; Dutch 21,841; U. S. 1,724,626
Wilkeite, U. S. 2,030,584
Wood wax, Brit. 239,483; Dutch 21,841; U. S. 1,724,626
WIrol, U. S. 1,934,057

Extractants and Solvents

Acetic acid, U. S. 1,928,968, 2,103,195
dichloro, U. S. 2,103,195
Acetone, U. S. 1,928,968, 1,934,057, 1,945,312, 2,030,584, 2,035,546,
2,052,374, 2,058,200, 2,089,766
Acetone plus alcohol, U. S. 2,058,200
Acetone plus ether, Swiss 124,290
Acetyl acetone, U. S. 1,928,968
Alcohol, Brit. 432,626, 437,171; U. S. 1,621,240, 1,854,948, 1,945,312,
2,030,584, 2,035,546
Alcohol plus ether, Swiss, 124,290
Alcohol plus sulphuric acid, U. S. 2,056,438
Alcohols, Brit. 350,897; U. S. 1,934,057, 1,940,646
Alkyl pyridines, U. S. 1,928,256
Allyl pyridine, U. S. 1,928,256
Anethol, U. S. 2,058,200
Animal Oil, U. S. 2,104,757

Apiezon, Brit. 446,576
Benzene, Brit. 246,252; U. S. 1,583,681; 1,934,057, 1,945,312, 2,058,200
Benzene, p-dichloro, U. S. 2,058,832
Benzine, Brit. 3204/1911, 432,628, 105,525; U. S. 1,065,156
Benzol, Brit. 285,797, 350,897; U. S. 1,621,240, 1,745,907, 1,854,948;
1,934,057, 2,934,057, 1,940,646, 1,967,024, 2,052,374
Bipyridine, U. S. 1,928,200, 1,928,256
Brown coal oil, Brit. 378,300




- 63 -


Camphor oil, Dutch 21,841; U. S. 1,724,626, 2,058,200
Carbon tetrachloride, Brit. 239,483, 285,797, 432,626; Dutch 21,841;
U. S. 1,724,626, 1,745,907 1,940,646, 1,942,104, 1,967,024, 2,035,546,
2,056,438
Cedrene, U. S. 2,058,200

Chloroform, Brit. 239,483; Dutch 21,841; U. S. 1,724,626, 2,052,374, 2,058,200
2,089,766
Citron oil, Dutch 21,841
3

coal tar oil, Brit. 378,300
Cottonseed oil, Brit. 446,576
Cresol, Brit. 280,256, 350,897; U. S. 1,934,057
Cresol, homologues, U. S. 1,934,057
Cyclohexanol, Brit. 350,897; U. S. 1,934,057
Cyclohexanol homologues, U. S. 1,934,057
Cymene, Brit. 434,660; Swed. 86,083
Decalin, U. S. 1,934,057
Diacetone alcohol, U. S. 1,928,968
Dipentene, U. S. 2,058,200

Esters, Brit. 350,897; U. S. 1,934,057
Ethane, trichloro, Brit. 285,797; U. S. 1,745,907
Ethane, trichloro, plus methyl alcohol, Japan. 91,478
Ether, Austral. 15,327/28; Brit. 239,483, 285,797; Dutch 21,841; Swiss 124,290;
U. S. 1,724,626, 1,745,907, 1,854,948, 1,945,312, 2,030,584, 2,056,438,
2,058,200
Ether arylalkyl, U. S. 2,042,296
Ether diethylene glycol, monoethyl, U. S. 2,039,766, 2,043,267
Ether, sec-hcxylcresyl ether, U. S. 2,042,296
Ether, sec-hexyphenyl ether, U. S. 2,042,296
Ethers, Brit. 350,897; U. S. 1,934,057
Ethyl, Dutch 21,841; U. S. 1,724,626, 1,928,256
Ethyl acetate, U. S. 1,945,312, 2,052,374
Ethyl alcQhol, Dutch 21,841; U. S. 1,724,626, 1,928,968, 1,940,646
Ethyl alcohol, absolute, Brit. 239,483
Ethyl format, U. S. 1,928,968
Ethylene chlorohydrin, U. S. 1,514,377, 1,928,968
S Ethylene dichloride, U. S. 2,o3o,584, 2,052,374, 2,058,200
Ethylene, dichloro, Brit, 423,625, 432,626
Ethylene, trichloro, Brit. 432,626
Gasoline, chlorinated, U. S. 2,013,023
Glycol, diethylene, monoethyl ether, U. S. 2,043,267, 2,089,766
Halohydrin, U. S. 1,514,377
Halowax oil, Brit. 350,897; U. S. 1,934,057
Hydrocarbon, aliphatic, Gor. 643,804
Hydrocarbon, aromatic, Brit. 350,397; U. S. 1,583,057
Hydrocarbon oil, Brit. 280,256
Hydrocarbon white oil, U. S. 1,736,125
Hydrocarbon white oil, chlorinated, Canad. 338,896; U. S. 1,934,057






- 64 -


Hydrocarbons -
chlorinated, Canad. 338,896;' U.S. 1,934,057
Paraffinic, U. S. 2,096,265
Unsaturated, Brit. 394,977; Canad. 340,315
Hydrogenated shale oil, Brit. 378,300
Hydrogenated solvent naphtha, Brit. 378,300
Isopropyl alcohol, Brit. 350,897; U. S. 1,934,057, 1,940,646.

Kerosene, Brit. 446,576; U. S. 1,940,646, 1,967,024, 2,0l3,020,
Kerosene plus chloroform, U. S. 1,967,024
Kerosene plus oil soluble sulfonpte, U. S. 1,940,646
Kerosene plus oil soluble sulfonate plus ethyl methyl ,ketone, U.
Kerosene plus soc-butyl alcohol, U. S. 1,940,646
Ketone, dicthyl, U. S. 1,928,968
Ketones, Brit. 350,897; U. S. 1,934,057


Lemon oil, U. S. 1,724,626
Lignite tar oil, Brit. 378,300
Limonene, U. S. 2,058,200
Linseed stand oil, Brit. 446,576
Lubricants, oils, Brit. 280,255
Lutidinc, (dimrethyl pyridine) U. S. 1,928,256
Mesityl oxide oxalate methyl ester, U. S. 2,070,603.
Methanol (methyl-alcohol), Brit. 239,483; Dutch 21,841;


2,042,296


S. 1,940,646


U. S. .,724,626


Methyl eugenol, U. S. 2,058,200 :
Methyl ethyl acetone, U. S. 1,928,968
Methyl ethyl ketone, U. S. 1,928,968
Mineral oil, U. S. 2,011,428
Mineral oil b.p. 300-600 F., U. S. 2,096,885
Mineral oil distillate, Canad. 369,390
Mineral oil, heavy, Brit. 446,576
Mineral oil, hydrogenated, Canad. 345,383
Mineral oil, volatile, Brit. 446,576
Mineral seal oil plus oil soluble sulphonate plus potn.sh ros-in soap plus
ethyl methyl ketone, plus hcxahydrophenol, plus cres.1o,, U. S. 1,940,646
Naphtha, U. S. 1,940,646
TNaphthalenes, chlorinated, Brit. 350,897; U. S. 1,934,057
Naphthalenes, hydrogenated, Brit. 350,897; U. S. 1,934,057.
Oils -


pine, U. S. 2,058,200
pine, steam distilled, Brit. 350,897; U. S,
Olive oil, Brit. 446,576
Petroleum Gea. 643,804
Petroleum distillate, U. S. 2,058,200
Petroleum oil, Brit. 377,069; Ger. 555,117
Petroleum distillate plus -
acetone, U. S. 2,058,832
benzol, U. S. 2,058,832
chlorobenzene, U. S. 2,058,8bc
chloroform, U. S. 2,058,832
dichloroethlrl ether, U. S. 2,058,832


10934,057





- 65 -


ethylene dichloride, U. S. 2,058,832
ethylene chlororydrin, U. S. 2,058,8932
n-,roTyl format, U. S. 2,058,832
toluene, U. S. 2,058,832
triciiloroethyl ne, U. S. 2,058,832
xylene, U. S. 2,058,832
Petroleum ether, Brit. 239,483; Tatch 21,841; U. S. 1,724,626
Petroleum naphtha, Canad. 338,896, 338,897; U. S. 1,854,948
Petroleum naphtha plus
acetone, U. S. 2,089,7'3
benzol, U. S. 2,089,766
ca:;phor sasafras oil, U. S. 2,039,766
carbon tetrachloride, U. S. 2,089,766
chloroform, U. S. 2,.89,766
diethylene glycol monoethyl ether acetate, U. S. 2,089,766
cthylrnc dichloride, U. S. 2,089,766
ethylene glycol monocot.hyl ether acetate, U. S. 2,089,766
Petroleum oil -
hydrogenatod, U. S. 2,066,184
non-volatile, U. S. 2,042,296
non-volatilc viscous, U. S. 2,013,028
white, Brit. 350,897
Petroleum white oil, Brit. -30,897; U. S. 1,934,057
Petroleum whito oil plus chloronaphthalcnc plus K-rosin soap, plus oil soluble
sulphonate, plus seoc-an-l alcohol, plus steam distilled pine oil,
U. S. 1,940,646
Petroleum white oil plus oil soluble sulphonate plus crude dichlorobonzono,
U. S. 1,940,646
Phollandrone, U. S. 2,058,200
Fne.ol, Brit. 350,897; U. S. 1,934,057
Phenol ether, alkylatod, U. S. 2,058,200
Phenols, Brit. 2c0,256
Phcnyl ethyl ketone, U. S. 1,2f8,968
m-phenyl toll ketone, U. S. 1,928,968
o--.henyl tolyl ketone, U.'S. 1,928,968
alpha-picoline, U. S. 1,928,256
beta-picoline, U. S. 1,928,256
gaar.a-picoline, U. S. 1,928,25'.
Prop-ionic acid, U. S. 2,103,195
Propionic acid, alpiha chiloro, U. S. 2,103,195
Fro)-.-lene chlorohydrin, U. S. 1,514,377
Pyridine, U. S. 1,923,25 1,928,968
Pyridine, alkyl, U. S. 1,928,256
Pyridine allyl, U. S. 1,928,236
Pyridine, ethyl, U. S. 1,928,256
Fyridine base, U. S. 1,928,256
Pyridine, dimethyl, U. S. 1,928,256
Pyridine, trimethyl, U. S. 1,928,256
Safrol, U. S. 2,052,3,74, 2,0538,200
Shale oil, :i;.-?rogenated, Brit. 378,300
Sodium bisulphite solution, Ger. 630,483






- 66 -


Ter-oineol, Brit. 350,897; U. S. 1,T34,057, 2,058,200
Terr)inolene, U. S. 2,058,200
Tetral.n, U. S. 1,934,057
Toluene, U. S. 2,058,200
Turpentinc oil, U. S. 2,058,200
Vegetable oil, U. S. 2,104,757

white oil, rit. 350,897; 'Uana. '3,73,642; U. S.. 2,011,428
Xylone, U. S. 2,058,200


PoaCents Used in Preparing Dorris extract


Aluiinmmn salt for coagulating daerris latex ,
Aluiinum sulphatec for coavulating dorris latex
Iron salt for coaallat in; derris latex
Load salt for coa-T;latinZ dorris latex- .
Lime, milk of, for coa,"ulating dcrris latex
Sulphuric acid in alcohol for C-7.tractin., derris
Salt in preparing dcrris extract
Sodium carbonate in preparing dorris uytract-
Sodium hydroxzide in prc;2,.Lring derris -extract
Tartaric acid in orefaring dorris extract


Brit.
Brit.
Brit.
Brit.
Brit.
Brit.
Brit.
B* ri t.
Brit.
Brit.


226,250
226,250
22P., 250
226,250
214,822
437,171
214,822
214,822, 437,171
226,250
214,822


Stabilizcrs


Anthracene, Brit. 350,897


Anthraquinones,
Anthraquinone s,
Anthraquinones,
Anthraquinoncs,
Anthraquinonos,
Anthraquinoncs,
An t- raqu i o no s,
Anthraquinonc s,
Anthraquinones,
AntiL ra Luinones,
Anthraquione s,
Anthraquinone s,
Anthraqui none s,


alkyl, U. S. 2,011,428
amino, U. S. 2,011,428
amino, alkylphenyl, U. S. 2,011,428.
amino, diary, U. S. 2,011],428
amino, oxrph:nyl1, U. 5. 2,011,428
mnino, phcnylated, U. S. 2,011,428
aralkyl, U. S. 2,011,428
aryl, U. S. 2,011,428
aryl diamino, U. S. 2,011,428
diamino, U. S. 2,011,428
-y:/ro-^, U. S. 2,011,428
nitro, U. S. 2,011,428
4,4-toluido, U. S. 2,011,428


Benzene, 1,2-dihydroxy-4-tert. alkyl, U. S. 1,942,827
Be~ieae, l,2-dihy-.-.roxy-4-tert. amyl, U. S. 1,942,827
Ee-izene, ],2-dihydroxy-4-tert batyl, U. S. 1,942,827
3BlacI: pigment, U. S. 2,090,109
Camphor, Brit. 350,897
Chlorophyll green dye, U. S. 2,090,109
Diphenyl, Brit. 350,897
Furoin, Brit. 350,897
alpha-I-aphthol, Brit. 350,897
Nitrocresol, Brit. 350,897
Orange yellow dye, U. S. 2,090,109






- 67 -


Phenanthrene, 3rit. 350,897
Phenylhydrazine, Brit. 350,897
Toluidine, Brit. 350,897

A List of All Patents Arranged According to Filing Dates


Filing Date
February 8, 1911
A-oril 27. 1911.

Teptembc.r 8, 1911
April 6, 1912
December 4, 1916
December 21, 1916
December 22, 1916
March 31, 1920
April 16, 1923
April 16, 1923
June 23, 1923
December 1, 1923
April 15, 1924
May 14, 1924
Hay 22, 1924
June 16, 1924
July 22, 1924
ITovember 12, 1924
November 22, 1924
November 26, 1924
November 29, 1924
April 24, 1925
June 25, 1925
August 31, 1925
F.3b;uary 10, 1926
October 5, 1326
November 24, 1926
Hay 18, 1927
October 3, 1927
October 19, 1927
November 7, 1927
February 10, 198
February 20, 1928
July 17, 1928
August 28, 1928
October 31, 1928
February 25, 1929
":arch 9, 1929
Harch 12, 1929
June 6, 1929
October 25, 1929
February 15, 1930


Patent
Brit. 3,204/1911
Brit. 10,215/1911

U. S 1,065,156
Brit. 8,322/1912
Brit. 105,525
Ger. 321,317
G-er. 327,583
U. S. 1,514,377
Brit. 214,822
U. S. 1,621,240
Brit. 226,250
rit. 229,773
Brit. 233,857
r.rnc.LI 589,969
Canad. 247,627
Austral. 18,227/24
S 1,522,041
irit. 246,252
French 589,506
Canad. 253,319
U. S. 1,583,681
:t. 239,483
Brit. 247,140
U. S. 1,724,626
Dutch 21,841
Swiss, 124,290
.-rit. 280,256
U. S. 1,786,125
U. S. 1,803,870
u. S. 1,940,646
U. S. 1,854,948
U. S. 1,745,907
Prit. 285,797
Brit. 300,606
Austral. 15,327/28
U. S. 1,934,057
Reissue 18,667 (U. S.)
U. S. 1,820,394
Canad. 293,233
U. S, 1,967,024
Canad. 333,642
Brit. 350,897









Filing date


March 11, 1930
March 12, 1930
Auagust 23, 1930
Aur-iast 23, 1930
September 10, 1930
November 28, 1930
1iarch 12, 1931
March 12, 1931
lay 4, 1931
July 5, 1931
Auguist 20, 1931
October 23, 1931
,Tovember 27, 1931
December 12, 1931
December 12, 1931
December 24, 1931
January 4, 1932
January 21, 1932
February 7, 1932
April 1, 1932
:.ay 14, 1932
July 8, 1932
September 8, 1932
September 12, 1932
October 19, 1932
October 29, 1932
November 22, 1932
February 20, 1933
March 17, 1933
March 27, 1933
April 10, 1933
May 23, l.-S
October 2, 1933
October 21, 1233
ilovembrer 15, 1933
December 12, 1933
January 24, 1934
January 24, 1'734
February 23, 1932
March 16, 1934
MIarch 16, 1934
March 19, 1934
April 4, 1934
April 28, 1934
May 31, 1934
June 5, 1934
September 24, 1934
0ctobr 2C, 1934


U. S. 1,847,540
U. S. 2,006,-53
U. S. 1,928,256
U. S. 1,928,968
Brit. 362,526
Ger. 555,117
U. S. 2,013,028
U. S. 2,042,296
U. S. 2,011,428
Ger. 564,018
U. S. 1,938,652
Canad. 33:.,896
Brit. 377,069
Brit. 378,300
Canad. 345,383
Canad. 340,315
Brit. 394,977
U. S. 1,940,899
Ger. 643,804
Canad. 338,897
U. S. 2,035,546
U. S. 1,954,517
U. S. 2,087,599
U. S. 2,058,200
U. S. 2,006,227
U. S. 2,C'66,184
Ger. 630,483
U. S. 1,942,104
U. S. 2,058,832
UT. S. 1,942,827
U. S. 1,945,312
U. S. 1,963,638
U. S. 2,043,267
U. S. 2,096,885
U. S. 2,090,109
U. S. 2,024,392
Canad. 348,379
Canad. 348,38n
French 769,445
Swedish 85,083
Swed. 87,325
Brit. 434,660
U. S. 2,083,098
U. S. 2,052,374
U. S. 2,104,757
U. S. 2,030,584
French 778,8,44
Brit. 446,576


- 68 -


Patent










Filing Date


December 17, 1934
January 11, 1935
January 11, 1935
Ilarch 20, 1935
March 30, 1935
August 27, 1935
August 29, 1935
September 4, 1935
September 11, 1235
October 25, 1935
October 28, 1935
October 29, 1935
January 3, 1936
:larch 7, 1936
December 24, 1936
July 3, 1937


Canad. 357,959
Austral. 20,894/35
Brit. 432,626
U. S. 2,049,725
Brit. 437,171
French 794,206
Canad. 362,903
U. S. 2,056,438
Ger. 646,570
U. S. 2,096,678
Canad. 369,499
French 797,052
U. S. 2,070,603
U. S. 2,089,766
Canad. 369,390
U. S. 2,103,195


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Patent










UNIVERSITY OF FLORIDA
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