- 446 
 
 UNITED STATES DEPARTMENT OF AGRICULTURE 
 
 BUREAU OF ENTOMOLOGY AND PLANT QUARANTINE 
 
 DVISION OF INSECTICIDE INVESTIGATIONS 
 
 ^SSboard 
 
 ABSTRACTS OF FOREIGN AND DOMESTIC PATENTS RELATING TO 
 DERRIS, LONCHOCARPUS, TEPHROSIA, AND ROTENONE 
 
 By 
 R. C. ROARK 
 
 Washington, D. C. 
 August 1938 
 
 
I 
 
E- 446 August 1 538 
 
 United States Department of Agriculture 
 Bureau of Entomology and Plant Quarantine 
 
 ABSTRACTS OF FOREIGN AND DOMESTIC PATENTS RELATING 10 
 
 DEERIS, LONCHOCARFUS , TSPHROSIA, AND ROTENONE 
 
 (From the time the first amplication for a patent on derris 
 v/as filed (February 8, 1911) to April 1938 
 
 By R. C. Koark. Division of Insecticide Investigations 
 
 Eleven countries have issued patents which cover derris, cube, 
 
 tcphrosia, or rotenonc products as insecticides, methods of extracting 
 
 rotcnone from plants, or processes of making dihydrorotcnone or other 
 derivatives. 
 
 The number of patents granted by each country is shown in the 
 following list: 
 
 Country Number of p aten ts 
 
 Australia 3 
 
 Canada 14 
 
 Franco 6 
 
 G-ermany 7 
 
 Great Britain 23 
 
 Japan 3 
 
 Johorc 1 
 
 Netherlands 1 
 
 Sv/cden 2 
 
 Switzerland 1 
 
 United States of America \ 49 
 
 Total 110 
 
- 2 - 
 
 Australian Patents: 
 
 McDougail and Howies (59), in Australian patent 18,227/24, issued 
 November 10, 1924, applied for June 16, 19.94, make identical claims to 
 the invention described in British patent 226,250. 
 
 The Zaidan Hojin Rikagaku Keukyujo (110), in Australian potent 
 15,327/26, issued July 24, 1929, applied for August 28, 1928, in Japan, 
 November 16, 1927, claims powdered insecticide prepared by causing the 
 active ingredients of the root of derris species to be absorbed by an 
 earth or earths such as clay, china-clay, earthenware clay or kiesclguhr, 
 which is or are free from water, alkali, and like substances detrimental to 
 the active ingredients, adding thereto a suitable quantity of magnesium 
 carbonate, calcium carbonate, or like adhesive medium, and crushing the 
 resultant mixture to powder. 
 
 Examples arc (l) twenty-five grams of powder of powdered dry roots 
 of derris are extracted with a half pound of ether, and, while the liquid 
 is agitated, 150 grams of dry kiesclguhr are r added. The ether is then 
 recovered. This kiesclguhr containing the absorbed active ingredient is 
 mixed, with 2 grams of powdered sulphur, 2 grams of powdered resin, and 45 
 grams of magnesium carbonate. The mixture is then finely powdered, oy a 
 crusher. (2) Fifty grams of raw root of derris are crushed and pressed, 
 and the juice is collected. This operation is repeated two or more times. 
 To the juice, thus obtained, 150 grais of reddish earth is added, and the 
 water content of the mixture is entirely driven off as by a vacuum evapor- 
 ator under low temperature. This earth containing the absorbed active in- 
 gredients is mixed with quantities of powdered sulphur, powdered resin, 
 and magnesium carbonate as in the previous example. The resultant mixture 
 -is then finely powdered oy a crusher. 
 
 The Imperial Chemical Industries of Australia and Now Zealand 
 Ltd. (45), in Australian patent 20,894/35, issued February 14, 1935, applied 
 for January 11, 1935, claims a method of treating sheep or other animals 
 in order to render them immune from attack or infestation br blow flics or 
 the like, which consists in subjecting the animals to treatment with a 
 solution or a. suspension containing one of the xanthates. An insecticide! 
 agent such as a silicofluoride, derris, pyrethrum, etc. , may be added. 
 One of the claims reads: "A new article of manufacture ^'or the purposes 
 indicated, produced by mixing together the following substances substan- 
 tially in the proportions indicated.: — 
 
 pot-as sium ethyl xanthate 8 parts 
 
 derris root powd.cr 4 parts 
 
 bentonite 2 parts 
 
 sulphonated. cod oil 1 part" 
 
 British Patents: 
 
 ilcDougall, McDougail, and HcDougall (63), in British patent 3,204, 
 issued May 8, 1912, applied for February 8, 1911, claim in the manufacture 
 
Correction for E-446 
 
 The following information should bo inserted on page 22 
 after the 3 lines at the top of the page. 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, ir United States patent l,242,9. c >4 issued 
 October 16, 1317; applied for January 16, 1917; daim 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, and other portions 
 of the plant are ground to powder and if desired mixed with 
 other ingredients. In the manufacture of an insecticide for 
 use for the destruction of plant pests, the ground material 
 may be mixed with soap, sulphur, or other substances. The 
 said ground material may also bo mixed with various other 
 substances to form preparations for the destruction of earth- 
 worms, grubs, and the like. The compound contained within 
 the material is extract able therefrom, when in a finely di- 
 vided state, by moisture or by immersing the material in 
 water. The said compound when extracted then mixes with the 
 substances which may be added to the ground material to produce 
 the desired finished product ready for use for dipping or 
 spraying," Softening reagents, antiseptics or bactericides 
 may be added thereto. 
 
 Lemmens and Fryer, in United States patent 1,242,955 issued 
 October 16, 1917; applied for January 16, 1917; claim a new anti- 
 parasitic 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 compound is mixed 
 with soap, sulphur, or other ingredients 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 aforesaid may be mixer 1 with soap, 
 sulphur, or other substances which zsr^c as emulsifying or 
 carrying agents and diluents.**-* The din, w^sh, or the like 
 may contain any desired proportion of the compound, according 
 to the class of service to which it is to be put. Or it may 
 be let 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 the destruction of small and delicate 
 insects up to 12 ounces of the compound to 100 gallons of wator 
 for the destruction of the mor^ hardy and vigorous varieties." 
 
 (over) 
 
- 2 - 
 
 Grove, iii United States Patent 1,455,435 issued May 15, 1923; 
 applied for July 25, 1922; claims a medical compound for the treat- 
 ment 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 
 cf the urine and the lithia salt to activate as a solvent and 
 diaphoretic. The preferred formula is T. virginiana (ground roots), 
 9 ounces; lithii citras, 1 ounce; powdered cinnamon, 30 grains; 
 cochineal, 3 grains; alcohol, 2 ounces; and water, 16 ounces,, In pre- 
 paring this remedy the roots of the herb T. virginiana, dried and 
 powdered, are boiled with 1 pint of water for about 1 hour. The de- 
 coction is then cooled and strained. The other ingredients are then- 
 added, and the compound is allowed to stand for 2 days. It is then 
 filtered and bottled. The compound is to bo taken internally, and 
 under ordinary circumstances a dose is 2 teaspoonsful every 3 hours. 
 [From his references to the literature relating to the medicinal 
 properties of this plant, which he calls goatsrue and also Tephrosia 
 virginiana, it is probable that Grove confused T. virginiana with 
 Galega officinalis, as both are commonly known as goatsrue. It, C. E. ] 
 
of insecticides, sheep dips, aninal cashes and vcmifuges, and the like, 
 
 the use of an org.ir.ic salt :r salts, conpound or eorpcandn obtained fron 
 the- plants, "bushes, or trees knew:: is tuba rabut, tuba tcdong, acre (or 
 akar) tuba, and pcrkakal, is set forth. The powdered bark, root, or other 
 portions of the plant arc extracted by a suitable solvent, such as bensinc, 
 the excess of solvent is evaporated, and the gunny residue is then nixed 
 with the necessary ingrediez.ts for producing the required dip, wash, in- 
 secticide, or vcrnifugc, or it nay be crystallized before such use. Dur- 
 ing the nanuf acturc of the dip, a suitable water- softening reagent or a 
 suitable antiseptic, bactericide, or coloring ratter nay be added. In 
 practice the fixture employed will contain fron 1 ounce of the conpound to 
 100 inperial gallons of water for the destruction of snail one 1 do-licatc 
 insects, up to 12 ounces of the conpound to 100 inperial gallons cf niter 
 for the destruction of the r.orc hardy and vigorous caterpillars. A suit- 
 able apparatus for the extraction is described. The extract nay be nixed 
 with sulphur, soap, or other ingredients and nade into a piste, powder, or 
 liquid in any known nanncr, 
 
 LicDougall, McDougall, ancl McDougall (65), in British patent 10,215 of 
 1211, issued May 28, 1912, applied for April 27, 1911, clain in the nanu- 
 facturc of sheep dips, aninal './ashes, vernifuges, ancl insecticides, the use 
 of in organic silt or salts, conpound, or expounds obtained fron the plants, 
 bushes, or trees of the fanily ixm,n botanically as Derris of the order of 
 Lcgrninosac, as set forth. Shis invention is an inprovenent over that des- 
 cribed in Britisi patent 3,204 of 1911. Tac nixturc nay be used for destroy- 
 ing carthwoms and as a dose for aninal s for the destruction of internal 
 parasites, "As a dose the nixturc nay contain fron about l/2 to 1 evince of 
 the extract onulsificd with about 4 ounces of soapy natter, the -.mole being 
 then nade up t"< 20 ounces by the addition of sulphur." 
 
 McDougall, McD-mgall, and McDougall (64), in British patent 8,322 
 of 1212, issued Deecnber 13, 1212, applied for April 6, 1912, clain inproved 
 insecticides, sheep dip, vcrnifuges, and the like conprising, in a powdered 
 or finely divided forn, the root, bark, or other portions of the plints, 
 bushes, or t:~ces of the Dalbcrgiac tribe and Derris fanily an of pcrkakal, 
 fror. which an organic salt or salts, conpound, or v compounds is cxtractablc 
 by noisturc r -.rater, subs tan tlally .is described. This invention is on in- 
 provencnt ever that described ir the patentees' prior soecif icati ons--3ritish 
 patents 3,204 of 1911 and 10,215 of 1911. The ground derris root nay be 
 nixed 'iith snap, sulphur, or other substances. 
 
 Lenncns and Fryer (54), in Britain patent 105,525, issued. April 19, 
 1217, applied for Deecnber 4, 1916, clain 
 
 "In the lanufacturc of insecticides, sheep dips, aninal 
 washes and the li he, the use of an organic salt or salts, conpound 
 or compounds obtained fro:: the seed's, leaves and other portions of 
 the plant of the species and. varieties of the fjenus of plants known 
 is Tephrosia of the natural or'cr Leguninosac and the sub-order 
 Papilionaceac, particularly the species of Tephrosia known as 
 Tcphro s i a vo'gol i i . " 
 
A _ 
 
 Ail apparatus for extracting the powdered dry plant material with 
 benzine is described. I:: practice, the mixture employed will contain from 
 1-1/2 ounces of the compound to 100 imperial gallons of water for the 
 destruction of small and delicate insects up tc 12 ounces per 100 gallons 
 of water for the destruction of the more hardy and vigorous varieties. 
 
 Bagnall-Bull (4), in British patent 214,322, issued May 1, 1324, 
 applied for April 15,1923, claims a method of obtaining dcrris extract 
 for use as an insecticide, vermifuge, sheep dip, or the like, which con- 
 sists in breaking or crushing the fresh roots or other portions of the 
 plants of the family known botanically as Dcrris or Tuba, treating them 
 with water so as to obtain .a milky emulsion or suspension of the juices 
 containing toxic properties, and then separating the emulsified substance 
 from the -./hole or a part of the water. 
 
 To separate the emulsified substance from the water, evaporate the 
 vdiolc or a part, preferably in vacuo, thereby obtaining a paste of a con- 
 sistency sui table for transport, or add to the milky emulsion milk of lime, 
 which coagulates or precipitates the emulsified substance. Tree the prociio- 
 itate obtained by the last method from excess moisture by evaporation, by 
 filtration, or by centrifugalizing. Or mix it with tartaric acid or any 
 other suitable acid in quantity equivalent to the mount ->f lime contained 
 in the -precipitate. Or the milky emulsion may be rendered alkaline with 
 soda carbonate, to which is them ad/ed a brine t salt solution in a quan- 
 tity sufficient to salt out the emulsified substance, which then precipi- 
 tates. The emulsified substance or precipitate so obtained is then dried 
 and ground or com. be usee 1 , in a moist condition according to the use to which 
 it is tc be applied. Grinding produces a powder, which by reason of its 
 fineness admits of a suspension of the drug in water. This preparation 
 .alone or mixed with inert powder may be used as a dusting powder, or it may 
 be mixed with soap, sulphur, or other suitable substance for use as insecti- 
 cidal washes, sheep dips, or for spraying, either as a powder or when mixed 
 with water. 
 
 IIcDougall and Eowles (58), in British patent 220,250, issued Decem- 
 ber 23, 1924, .applied for June 23, 1923, claim a process for the -production 
 of an insecticide, shccf dip, vermifuge, or the like which is directly mis- 
 ciblc with water, by crushing or pressing the root portion of plants, bushes, 
 or trees of the Dalbcrgir. tribe and Dcrris family to a pulp, scouring the 
 fibrous particles by mechanical means in the presence of "motor .and finally 
 separating the fibrous material from the magna, substantially as described. 
 The latex may be evaporated in a vacuum at a low temperature. The active 
 material obtained as before described, may, if desired, be mixed with water 
 and/or soaps of various kinds, such as rosin, fatty acid or sulphonatcd. oil 
 soaps, sulphur, antiseptics, water softening materials, spreaders, end the 
 like, for the destruction of insect pests on animals and/or plants or for 
 internal or external parasites. The active ingredients may be separated 
 from the latex by precipitation with a basic salt of aluminum, iron, or lead. 
 For example, to 100 cubic centimeters of the latex, a quantity of concentrated 
 aluminum sulphate solution is added, so that the final dilution of the alum- 
 inum sulphate in the latex is equivalent to 0.2 percent. To this is added 
 a solution of caustic soda in quantity insufficient to precipitate the whole 
 
c _ 
 
 of tlic aluminum sulphate as hydroxide-. The coeg'olum is then treated with 
 an appropriate dilute acid to free it fron nctallic salts, after which it 
 is readily emulsified in water and soap. 
 
 HcDougall and Raiding, Ltd. and P. J. Fryer (69), i,n British patent 
 229,775, issued March 2, 1925, applied for December 1, 1223, claim insecti- 
 cides, sheep dips, animal washes and the like, .comprising an organic salt 
 or salts, compound or compounds obtained fron the root, hark or other por- 
 tions of the plants, hushes, or trees of the Dalbcrgiae trihe and Dorris 
 family and/or of pcrkakal, and sulphonated castor oil as a vehicle or spread- 
 ing or activating agent for such organic salt or salts, compound or compounds. 
 
 McDougall and Howies (60), in British patent 253,857, issued May 21, 
 1925, applied for April 15, 1924, claim in insecticides, the combination 
 comprising: a mixture of niotino with the aforesaid dorris extract or pow- 
 dered dorris plant and a neutral inert "body, substantially as descrihed. 
 An example of preparing this insecticide is: 2 parts by weight of nicotine 
 are nixed with 5 parts by weight ",f powdered root and 93 parts of precipi- 
 tated calcium carbonate. The extract may "or obtained by the process described 
 in prior specification }Tos. 3,204 of 1311, 10,215 of 1911, and 8,322 of 1912, 
 or in specification 'So, 226,250. This is used in powder form for dusting 
 hops and fruit trees for the destruction of aphids, psylla, and various 
 caterpillars. 
 
 The Zaidan Eojir i&kagaku Kcnkyujo (102), in British patent 239,483, 
 issued May 6, 1926, applied for April 24, 1925, in Japan, September 8, 1924, 
 claims a process of preparing a liquid insecticide containing the effective 
 ingredient Of the dorris species, comprising the stop of prep '.ring a primary 
 reagent in which the effective ingredient is mixed wi th one or more oils 
 and/ or fats, waxes, resins, higher alcohols, higher hydrocarbons, higher 
 fatty acids (excluding Turkey rod oil), which -.re entirely free fron water 
 and alkali; and the stop of preparing a secondary reagent in which the pri- 
 mary reagent is nixed as a col] )idal solution, substantially as described. 
 Examples arc: 
 
 " (l) A solution of 10 litres of ether containing 10 grammes 
 of rotcnor.c is added to a mixture of 400 grammes of fish oil with 
 40 grammes of hydrogonatcc! oil. After sufficient agitation, the 
 greater part of the jthcr is recovered by evaporation and conden- 
 sation, and thereby a semi-solid mixture is obtained as a primary 
 reagent. Five hundred grammes of so \p are nix.ee 1 with 100 kilogram- 
 mes of water to prepare a colloidal aqueous solution as a secondary 
 reagent. In use, the primary reagent is mixed with the secondary 
 ■reagent end it nay be suitably dilutee"! with addition of 10 n kilo- 
 grammes of water when used .as an insecticide. The secondary reagent 
 may be prepared at any tine by users. 
 
 "(2) Ton litters of ether arc added to 1 kilograaic of the 
 dorris root. After 4 days, the extract is added to 400 grammes of 
 chrysalis oil and 100 grammes of lard. After evaporating the ether 
 a semi-solid substance is obtained as a primary reagent. 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, bean 
 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 
 tallcw, hydi'ogeniGed 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 and the like. By higher hydrocarbons paraffin and 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, egg-albumin, bean milk, dextrine, starch, bengal 
 isinglass, animal albumin and the like. There may be added to said aqueous 
 solutions a small quantity of methyl alcohol, ethyl alcohol, chloroform, 
 ejrher, 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 pla.ee 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 ca,sein 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. 
 

 The fresh root of tuba is crushed, and after a snail quantity of 
 water is added it is filtered. The filtrate is allowed to settle for 
 ah out three hours in order to allow resinous natters tc separate. The 
 supernatant material is then evaporated in a vacuum evaporating pan or 
 an ordinary evaporator at a tenporature net exceeding 70°. The contents 
 when pasty, are spread on glass or iron plates and dried in a drying 
 chanter at' ?. ter.ipcrr.ture of 40° to 45° until they hecone a deep-brown, 
 solid nass» The solid mass nay he pulverized, for convenience of use. 
 The powdered product is a light-brown powder which contains about 30 to 
 32 percent of rotenonc, 34 to 35 percent of dorrid, and 35 percent of im- 
 purities, such as resin, albuncn, gun, and .ash. "When -it is properly di- 
 luted ''oy the addition of the desired quantity of water, it becor.es the best 
 insecticide for agricultural purposes." 
 
 "The product is no re effective than those containing the 
 sane quantity of a single kind cf toxin, because, as is well-known, 
 the simultaneous use of two or norc kinds of toxins is far norc 
 effective than the use of the sane quantity of any one of then," 
 
 LlcDougall and Yalding Ltd. end P. J. Fryer (71), in British patent 
 280,256, issued November 17, 1927, applied for November 24, 1926, claim a 
 process for producing concentrated complete and self-contained insecticides 
 containing physiologically active, substantially water- insoluble plant ox- 
 tracts, extracted from plants mainly of the order Leguninosae (particularly 
 those containing tuba-toxin (rotcnon) and. or tcphrosin) which consists in 
 dissolving such extracts in a phenolic body or suitable solvent, adding 
 the solution to a hydrocarbon oil or mixture of hydrocarbon oils and 
 finally emulsifying the whole, the emulsion so produced necessitating only 
 simple admixture with water in suitable proportions to form a spraying so- 
 lution. 
 
 According to one example, 1 part of the resinous active principle 
 from dorris or other source is dissolved by warning it with 2-l/2 parts of 
 commercial cresylic acid. This is now added to 28? parts of a suitable 
 hydrocarbon oil — for example, medium lubricating — oil fraction of American 
 petrol cum—an r 1 after the addition of 100 parts of a 10 percent glue solution 
 the whole is emulsified. According to a second example, tho. solution of the 
 active principle in cresylic acid, as described in tho first example, is 
 add.ed to 288 parts of suitable hydrocarbon oil, and the whole is mixed with 
 12 parts of ammonium oleate or linolc.te to form a homogeneous solution, 
 which is diluted with water. 
 
 The Zaidan Hojin Rikagaku Kenkyujo (108), in' British patent 285,797 
 issued November 29, 1928, applied for February 20, 1928, in Japan February 
 18, 1927, claims a process for producing a liquid insecticide containing 
 the effective ingredient of derris species, which comprises forming a pri- 
 mary material in which the effective ingredient is nixed with an anhydrous 
 and alkali free vehicle for the o.ctive ingredient, said vehicle consisting 
 of one or more oils, fats, waxes, resins, higher alcohols, higher hydro- 
 carbons, higher fatty acids, together with a substantially equal quantity 
 of the anhydrous solvent, benzol, carbon tetrachloride or trichlor ethane, 
 which primary material is subsequently to be nixed with ar aqueous soap so- 
 lution to form a colloidal solution. 
 
- 8 - 
 
 Examples arc: (l) To 100 grans of powdered dcrris root, 10 liters 
 of ether is added and thereby the effective ingredient of the derris root 
 is extracted, the whole or greater part of the ether is evaporated and 
 recovered. To the residual effective ingredient a mixture of 150 grans 
 of anhydrous and alkali-free fish oil (as a vehicle) and 150 grans of "benzol 
 (as the anhydrous solvent) is added, so that a solution of the effective 
 ingredient is thus prepared. This is the inprovod primary material. The 
 soap solution is easily prepared by, for instance, adding 500 grams of soap 
 to 100 kilograms of water. The solution thus obtained is mixed with the 
 improved primary material in use. 
 
 (II) To 1 kilogram of powdered derris root, 5 kilograms of benzol 
 is added and the effective ingredient of the derris root is extracted 
 while warning the benzol. The benzol is recovered by evaporation. To the 
 residual effective ingredient, a mixture of 600 grans of anhydrous and 
 alkali-free fish oil (as a vehicle) and 600 grams of carbon tetrachloride 
 (as an anhydrous solvent) is added so that a solution of the effective in- 
 gredient is formed. This is the improved primary material. The soap so- 
 lution employed therewith may be the same as in the above mentioned exam- 
 ple. Trichlor-ethane CoHr Z Cl^ as the anhydrous solvent can also be used. 
 Also in the two examples given, the improved primary material can oe easily 
 prepared in the form of powder when 900 grans of anhydrous gun arabic are 
 added. 
 
 The Zaidan Hojin Rikagaku Kcnkyujo (109), in British patent 300,606, 
 applied for July 17, 1928, in Japan, November 16, 1927, made essentially 
 the same claims as in Australian patent 15327/28 (110). 
 
 The Standard Oil Development Company (95), in British patent 350,897, 
 issued June 15, 1931, applied for February 15, 1930, claims an insecti- 
 cidal, insect-repellent, or fungicidal composition comprising petroleum 
 white oil, an extract of a plant having insccticidal properties and an emul- 
 sifying agent. The insccticidal plant nay be a fish poison such as Dcrris , 
 Lonchocarpus , or Tophrosia . Instead of, or together with the fish poison 
 pyrcthrun may be used. An example is "Two kilograms of ground derris roots 
 were extracted with four litres of benzol. Distilling off the solvent in 
 vacuo 113 grans of dry extract v/crc obtained representing 5.65 percent of 
 the dry derris roots and having the appearance of a reddish brown resin. 
 Eighty grans of this extract v/crc fed into a colloid mill with a solution 
 of 750 grams of oil-soluble sodium sulphonate derived from petroleum oil 
 in 2.5 litres of technically pure while oil. Water was also added in the 
 amount of 1,5 litres. A thick emulsion resulted similar in appearance to 
 mayonnaise and ready for marketing. Part of this prcparati~n was diluted 
 with 50 times its weight of water and : ';ave an effective insccticidal spray 
 for horticultural purposes," Dcrris may be extracted with a volatile sol- 
 vent such as benzol or isopropyl alcohol or with '.Thite oil directly. 
 Volatile solvents such as alcohols, ethers, esters, ketones, aromatic 
 hydrocarbons, etc., may be user 1 to increase its solvent power. It is de- 
 sirable to distil off subsequently most of the volatile solvent from the 
 proguct obtained. Another class of solvents may also be added to the while 
 oil before extraction, namely, steam distilled pine oil, terpincol , phenol, 
 
cresol, cyclohexanol and its homologues, and hydrogenated or chlorinated 
 naphthalenes such as the material known under the trade name "halowax 
 oil". The ingredients just mentioned are not removed by subsequent distil- 
 lation. They are desirable in the product and confer upon it a fungicidal 
 and bactericidal effect in addition to its insecticidal properties; they 
 also facilitate the omul si fi cation. 
 
 Various emulsifying agents may be used such as, for instance, fatty 
 
 acid soap, rosin soap, saponin, soaps of petroleum sulphonic acids, soaps 
 of sulphonated vegetable or animal oils, etc. When the plant is extracted 
 directly with the white oil, part of the soap used may be added to the 
 white oil before the extraction since it has beer- found that the presence 
 of a soap facilitates the extraction. In many cases it is preferred to 
 use the soap of an oil-soluble sulphonic acid derived from petroleum. Such 
 acids arc obtained in the refining of the white oils. This spray is ef- 
 fective against various aphids, tent caterpillars, scale insects, red mite, 
 tomato moth, cabbage worn, sawflies, etc. The oxidizing action of the air 
 on white oils and the development of acidity may be inhibited by the addition 
 to the oil of small percentages of some substance known generally under the 
 name of anti-oxidation catalyst. As examples, phenanthrcne and anthracene 
 nay be mentioned, 0.3 percent of which when added to the white oil prepar- 
 ation .arc Sufficient to protect completely the latter against the oxidiz- 
 ing- action of air. A Treat variety of other anti-oxidation catalysts may 
 be used such as, for instance, diphenyl, toluidiue, which have an oxida- 
 tion inhibiting action when present in concentration as low as 0.3 percent 
 of the oil. Other anti-oxidation catalysts which nay be used arc alpha- 
 naphthol, camphor, nitrocrcsol, phenylhydrazine, furoin, etc. The anti- 
 oxidation catalysts arc preferably added tc the white oil containing vege- 
 table insecticidal principle before the omulsif ication of the latter is 
 carried out, 
 
 Graafiand ana Nelleustcyn (30), in British patent 362,526, issued 
 December 10, 1931, applied for September 10, 1930. in Holland September 
 12, 1229; claim an antifouling composition against growth of and damage 
 by organisms in water comprising a. hydraulic binder anc! a poisonous sub- 
 stance other than one which acts upon iron to cause formation of salts of 
 iron, the composition being adapted to permanently retain its hydrophile 
 character, A suitable composition is Portland cement, 100 parts ^r weight; 
 powder of blossoms of Clar y san t horium cincrariaefel iun, 5 - 30 parts by 
 weight; water, 110 parts by weight. The Portland cement must be carefully 
 mixed with the powder of said blossoms. The mixture is rendered plastic 
 by the addition of a quantity cf water, which plastic mixture is applic- 
 able in an easy manner, such as for instance bj painting with a brush, by 
 spraying, or the like. After hardening of the coating a porous layer has 
 been formed, in which, because of its hydrophile character, the poison 
 remains effective and prevents the organisms from settling on or in it. 
 Another effective poison is for instance extract fro;: Scrris clliptica . 
 
 The I. C-. Farbenindustrie, A. G. (39), in British patent 377,069, 
 issued July 21, 1932, applied for November 27, 1951 ; in Germany November 
 27, 1930, claims a 'preparation for killing or eliminating files comprising 
 
-lo- 
 
 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 perhydrogenated petroleum boiling between about 180° and 290° CY and 
 the solution is utilized in the usual manner for killing flics, When 
 using extracts, as for instance extract of pyrethrum flowers, the said 
 hydrogenated products may be used as solvents for preparing these ex- 
 tracts. 
 
 The I. G. Farbcnindustric, A. G. (41), in British patent 378,300, 
 issued August 11, 1932, applied for December 12, 1931, in Germany De- 
 cember 13, 1930, claims a preparation 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 hydrogenated petroleum or petroleum dis- 
 tillates mentioned in British patent 377,069, favorable effects arc ob- 
 tained '"oy 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. Tor the preparation of agents for killing flics 
 there may, for instance, be used the hydrogenation products of mineral 
 oils (for instance lignite-tar oil, coal-tar oil or shale oil) or the hy- 
 drogenation products of distillation products thereof, or there may be 
 used synthetic oils of the same kind obtained, for instance, by the hy- 
 drogenation of brown coal until the hydrogenation products are free from 
 unpleasant odor or there may be used the distillation products of the oils 
 obtained by such hydrogenation. There may advantageously be used hydrog- 
 enated oils of a specific gravity of about 0.75 to 0.85 at 20° C. and 
 boiling between about 100° C. and about 300° C; such hydrogenated prod- 
 ucts may be obtained by hydrogenating, under raised pressure and temper- 
 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 may be pyrethrum extract, derris ex- 
 tract or an ester or ether of benzoic acid or a derivative or substitu- 
 tion product of this acid. For example 0.5 part of pyrethrum. extract, 
 3.5 parts of 5-chloro-2-hydroxybcnzcic acid ainyl ester and 2 parts of 
 iso-bornyl acetate arc dissolved in hydrogenated solvent naphtha. The 
 preparation completely hills flics, eulicidae, and similar insects. 
 
 The Standard Oil Development Co., assignees of Sankowsky and 
 Fulton (96), in British patent 394,977, issued July 4, 1933, applied for 
 January 4, 1932, in the United States January 5, 1931, claim .an improved 
 insecticide comprising hydrocarbons rich in "unsaturated hydrocarbons" 
 and obtained by the extraction of a petroleum naphtha with a solvent 
 having a preferential solvent action for said "unsaturated hydrocarbons" 
 in admixture with an insecticidal plant extract. The insecticidal plant 
 
- 11 
 
 extract nay be iron pyrethrum, cube, derris, or the like. Tests upon 
 houseflies showed that unsaturated hydrocarbons are more toxic than 
 saturated ones. 
 
 The Chenische Fabrik Marienfelde G.m.b.H. (14), in English 
 patent 432,626, issued July 30, 1935, applied for January 11, 1935, in 
 Germany, January 18, 1934, clain "a process for the manufacture of dur- 
 able, highly concentrated derris root extracts which arc enulsifiable with 
 water, characterized by adding weakly acid alkali resin soaps to a derris 
 root extract obtained by means of, and containing, di- or trichloroethylenc. " 
 
 An example of the process is as follows: 
 
 "Derris roots arc exhaustively extracted with di- or trichloro- 
 ethylenc, and the filtered solution is concentrated until it contains one 
 part of derris root extract in one part of di- or trichloroethylenc. Resin 
 is saponified with caustic soda solution of 36° Be, only sufficient caustic 
 soda solution being 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 dichlorocthylcnc, while being heated under a 
 reflux condenser, and the solution is mixed with 100 kg. of the derris 
 root extract concentrated to 1:1." 
 
 Pyrethrum extract may be similarly used. Di- and trichloroethylenc 
 are better solvents for derris constituents than arc alcohol, benzine, 
 carbontetrachloride , c tc. 
 
 Wikstron (102), in British patent 434,660, issued September 6, 1935, ■ 
 applied for March 19, 1934, claims an insecticide comprising cymene [cyr.ol] 
 or a derivative thereof and the active constituents of pyrethrum or derris 
 or quassia or equivalent vcrmin-dcstro.ying 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 may be extracted with cymene. 
 
 A further very valuable ingredient is chlorinated or sulphurated 
 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. These products may 
 be prepared by treating an ethereal oil, such as oleum citronellae, oleum 
 eucalypti (for example the product known as "Globulus"), oleum cedri, 
 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 may be alkaline, and is then dissolved in cymene (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 an attenuating agent and as 
 an emulsifying agent. 
 
 It nay a]. so "be of advantage to add a specific emulsifying agent, 
 for example, triothanolamine, -j 
 
 Examples are: (1). Derris-cynol extract (15 percent) 1 part, 
 Trietlianol amine- 0.1 part, water 100 parts. The triethanolaninc is first 
 dissolved in water and the derris-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). Pyrethrun-cynol extract (15 percent) 1 part, 
 derris-cynol extract 1 part, water 200 parts. (3). Pyrethrun-cynol ex- 
 tract (15 percent) 1 part, derris-cynol extract 1 part, quassia-cynol ex- 
 tract 1 part, water 300 parts. (4) Pyrethrun-cynol extract 15 percent 
 1-60 parts, derris-cynol extract or quassia-cynol extract 1-60 parts, 
 chlorinated or sulphurated ethereal nils 2-60 parts, soap 200-400 parts, 
 water 2,000-200,000 parts. 
 
 A convenient stock solution nay consist of: Pyrethrun-cynol ex- 
 tract (15 percent),- derris-cynol extract or quassia-cynol extract total 
 15 parts, chlorinated or sulphurated ethereal oils, 6 parts, soap 79 
 parts. To this mixture is added, when it is to he used, enough water to 
 nakc a 0,25-15 percent solution. The liquid nay be sprayed or sprinkled 
 on the plants or other objects which arc to be treated, but dipping or 
 other methods of distributing the liquid nay also be employed. 
 
 The Booth Steamship Co. Ltd. and H. G. Ward, (?), in British 
 patent 437,171, issued October 24, 1935, applied for March 30, 1935, 
 claim: 
 
 The process for extracting toxins for the manufacture of insecti- 
 cides from roots containing rotcnone, according to which the roots in 
 crushed or ground forn are digested in common alcohol acidulated by pure 
 sulphuric acid, and the mixture filtered so that the final filtrate con- 
 tains the rotcnone and incidentally also other toxins of an insecticidal 
 value present in the root. 
 
 The filtrate nay be neutralized with sodiun carbona.te .and refil- 
 tcrod. The final filtrate nay be nixed with soft soap so as to obtain a 
 scni-solid product which can be diluted with water before use, 
 
 Fawcctt and Imperial Chenical Industries, Ltd, (26), in British 
 patent 446,576, issued April 29, 1936, applied for October 29, 1934; 
 claim a, process for the production of rotcnone and/or preparations hav- • 
 ing insecticidal value and containing rotcnone, which comprises subjecting 
 the natural substances containing rotcnone, to distillation at raised 
 temperature in a high va.cuun and collecting the distillate. A vacuum of 
 between 10 and 10"^ mm. of .mercury is used. The condensate from the 
 distillation nay suitably be removed from the condensing surfa.ee by melt- 
 ing down, by scraping, or by rinsing with a solvent. An example of the process 
 
13 - 
 
 w 
 
 is as follows: """ifty ports of dry ground derris root are mixed with 100 
 parts of a linseed oil stand oil \7hich has previously been treated in a 
 high vacuum at 220° C. to remove volatile constituents. The mixture of 
 derris root and oil is fed on to a heated surface or surfaces maintained 
 at abcu.t 120° C. and in close proximity to a colri condensing surface, the 
 whole apparatus being evacuated to about 10~^ mms. of mercury. A pale 
 yellow condensate is obtained, giving the reactions of rotenonc and con- 
 taining substantially all the active material present in the original root, 
 
 Other carrier liquids such as Apiczon, heavy mineral 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 derris 
 or cube root may 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 respectively 
 under the trade names 'Apiezon A' end 'Apiczon K' nay bo v.sed. The active 
 ingredients distil over together with the 'Apiczon A' leaving behind a 
 suspension or solution of the residue in the 'Apiezon K' . The distillate, 
 which is a more or loss concentrate*-! solution of the rotenone etc. in 
 'Apiezon A' (the concentration can be varied by varying the proportion of 
 'Apiczon A' taken), is suitable for dilution with kerosene or other vol- 
 atile mineral oil for use as insecticidal spray." 
 
 Canadian patents. 
 
 McDougall and Howies (61), in Canadian patent 247,627, issued 
 March 17, 1925, applied for May 22, 1924, make the same claims es in 
 British patent 226,250. 
 
 McDougall and Yalding Ltd.-, assignee of P. J. Fryer (67), in 
 Canadian patent 253,319, issued September 1, 1925, applied for November 
 26, 1924, claim a process for the production of insecticides, shcup 
 dips, animal washes, and the like which consists in nixing or incorpor- 
 ating with an organic salt or salts, compound or compounds obtained from 
 the root, bark, or other portions of the plants, bushes, or trees of the 
 Dalbcrgiac tribe and Derris family and/ or of perkakal, a sulphonatcd fat- 
 ty oil, sulphonatcd spem oil, or a sulphonatcd wax as a vehicle or spread- 
 ing or activating agent for such organic salt or salts, con-pound or com- 
 pounds. The sulphonatcd fatty oil nay be sulphonatcd castor oil. 
 
 Dennis (19), in Canadian patent 293,233, issued September 24,' 
 1929, applied for March 12, 1929, makes essentially the sane claims for 
 ground cube root with the fibrous element removed and for an extract of 
 cube root as he previously made it in his United States patents. 
 
 The Standard Oil Development Company , assignee of Grant (31), in 
 Canadian Patent 333,642, issued June 27, 1933, applied for October 25, 
 1929, makes the following claims: 
 
- 14 
 
 "A spray for sensitive foliage comprising a derris ex- 
 tract incorporated in white, oil. A composition of matter com- . 
 prising an aqueous amulision of-^hite oil containing an organic 
 solvent extract of derris. A, spray comprising a concentrated 
 aqueous emulsion of \7hite oil containing rotenone diluted with 
 about 50 to. 100 times .its volume of water.' 1 ' 
 
 The Standard Oil 'Company, assignee of Adams (1), in Canadian 
 patent 3.36,396, issued January 23, 1934, applied for October 23, 1931, 
 claims a mothproofing composition comprising a chlorinated 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 W. J. McG-ill (73), in 
 Canadian patent 336,597, issued January 23, 1934, applied for April 1, 
 1932, claims a mothproofing solution containing an extract of derris. 
 Claim is also made for a solution of the active principle of haiari in 
 petroleum naphtha boiling ■between 450-550° F. 
 
 The Standard Oil Development Co. , assignee of Sankonsky and 
 Fulton (37), 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- 
 carbons .and obtained ~r>y the extraction of a petroleum naphtha with a 
 solvent having a prcf orontial solvent action for said unsaturated hydro- 
 carbons, and containing the extractives of. at least one of the plants 
 selected from the group- consisting of pyre thrum, cube, derris, and the 
 1 ikc. 
 
 Thc International Eydrogcnation Patents Company, Ltd.,. Vaduz, 
 Liechtenstein, assignee of Pfaff end Dunked. (8.1), in Canadian patent 
 345,383, issued October 16, 1934, applied for December 12, 1931, in 
 Germany December 13, 1930, claim an insecticidal composition, compris- 
 ing a solution of an insecticidal plant extract and/ or a compound of 
 the group comprising esters and ethers of benzoic acid and substitution 
 products thereof in a hydrogenated mineral oil boiling between about 
 100 C. , and 300° C. and having a specific gravity of about 0.75-0.35 
 at 20° C. 
 
 Schottc and G-ornitz (88), in Canadian patent 343,579, issued 
 February 26, 1935, applied for January 24, 1934, claim an insecticidal 
 preparation consisting of a mixture containing extracts of drugs con- 
 taining rotenon end voratrin. They also claim an ivisecticidal prepar- 
 ation consisting of a mixture containing radix dcrridis cllipticac and 
 semen sabadiilae. 
 
 Schottc and Gb'rnitz (89), in Canadian patent 348,330, issued 
 February 26, 1935, applied for January 24, 1934, claim a solidified 
 finely distributed mixture of a molten carrier and finely distributed 
 derris root. Foddered tobaoco or pyrcthrum may be used in place of 
 the derris. 
 
- 15 - 
 
 The Kessler Chemical C^rp. , assignee of S. G-oldschmidt and K. 
 
 Martin (29), in Canadian patent 357,959, issued May 19, 1936, applied 
 for December 17, 1934, • in Germany December 27, 1933, claim as a toxic 
 agent and more particularly an .insecticide, a preparation comprising 
 as an active constituent an aromatic in so thio cyan ate 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 England, 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 Canadian patent 369,390 issued October 19, 1937, applied for December 
 24, 1936, 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 pyre thrum, and a small proportion of. a. substituted 
 aryl compound in which at least one hydrogen atom of the aroma-tic nucleus 
 is replacd!. by a member of the group consisting of amino, hydroxyl,, and 
 alkyl radicals. Dihydroxy and dialkyl mono-hydroxy aromatic compounds 
 are also included among the substituted aryl compounds. 
 
 Imperial Chemicals Industries Otd. (46), assignee of Fawcett, 
 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-contai-ning substance to 
 distillation without ebullition at a pressure of 10 to 1C~6 mm£t f 
 mercury under such conditions that the evaporating and condensing surfaces 
 are substantially co-extensive and 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 Uettai 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: (l) 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 
 
- 16 - 
 
 "be diluted with 100 kilograhs water* (2) T^ 1 kilogran of derris root 
 is added 10 liters of ether , After four days 400 grans of chrysalis oil 
 and 100 grans of hog suet arc added to the extract. The ether is evapor- 
 ated leaving about one-half the original volume. From here on proceed 
 as in Example No. 1. (3) One kilogran of dprris root is soaked with 20 
 liters of petroleum ether. After 4 days 200 grans of "beeswax end 50 
 grans of pine resin arc added to the extract.- ''After this has dissolved 
 as nuch as possible, the greater part of the pctroleun ether is recovered 
 "by evaporation and condensation, leaving a scnicolloidal nass. This resi- 
 due con "be dispensed as a colloid in a solution of 200 grans of soap in 
 100 kilograms of water, 
 
 Hotenone deconposcs on long contact 'v7ith water or with alcohol 
 containing water. Further, the active principle is unstable in the 
 presence of alkalies. 
 
 Suitable solvents for the extraction of dcrris arc ncthyl alcohol, 
 ethyl alcohol, ether, petroleup. ether, chlorofom, carbon tetrachloride, 
 etc. As oils the following nay bo used: oil sorts of ani.nal oils,- such 
 as sourdine oil, herrino 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 linseed oil, etc. As regards fats, all sorts of aninal fats 
 nay be used such as (hog) suet, beef tallow, as well as hardened plant 
 oils. As waxes, ray be used the following: Beeswax, wood wax, etc. As 
 resins, pine resins, copal, etc.' Suitable higher hydrocarbons nay be 
 paraffin or sinilar conpounds, higher alcohols, such as glycerine, etc., 
 the ones chosen depending on circunstanccs. 
 
 As emulsifying agents the following nay be used; aqueous solutions 
 of soap, glue, egg white, milk of soya bean, dextrin, starch, Bengal fish- 
 glue, animal protein, etc. Sometimes to the aqueous solutions are added 
 a smo.ll quantity ethyl alcohol, chloroform, ether, oil of camphor, citron 
 oil, or other solvents. 
 
 French Patents; 
 
 McDougall and Yalding Ltd. (68), in French patent 589,506, issued 
 May 30, 1925, applied for November 22, 1924, in England December 1, 1923, 
 make essentially the sane claims as in British patents 229,773 and 246, 
 252. A sulphonated wax or a sulphonatcd fatty oil (castor or spern) nay 
 be used as the spreading agent with derris extract. 
 
 McDougall and Howies (62), in French patent 589,969, issued June 
 9, 1925, applied for May 14, 1924, in England June. 23 and November 22, 
 1923, nako the sane claims a.s in British patent 226,250. 
 
 Dipre and Company (23), in French patent 769,' 45 published August 
 25, 1934; applied for February 28, 1934, claim an insecticide consisting 
 of quassia, extract, vegetable oil and rotenone (or extract of derris or of 
 cube), plus sassafras oil. This is nade by nixing 10 kilograms of quassia 
 
- 17 - 
 
 extract (25$) p]us about 4 kilograms of tricthanolamino with 50 kilo- 
 grans of vegetable oil (e.g.huile do arachidc) plus 11 kg, oleic acid 
 plus 1 kg. rotcnonc plus 100 grans sassafras oil. For use the nixturo 
 is diluted with from 100 to 150 tines its weight of water* 
 
 The J. D. Ric&el-E. Do Hacn A.-G. (82), in French patent 778,844 
 issued March 25, 1935, applied for September 24, 1934, in Gornany Sep- 
 tenber 30 and November 8, 1933, clain a process in which extracts of 
 plant insecticides (e. g. extracts of Cli r y s an th cmun ci nc rariaef ol iun and 
 of varieties of Dcrris) are atomized by air under pressure to destroy 
 insects. Aqueous emulsions of these extracts may be used. 
 
 Thc Booth Steamship Co., Ltd., and H. G. War'-" (8), in Trench 
 patent 794,206, issued February 11, 1936, applied for August 27, 1935, 
 in England, March 30, 1935, make the sane claims as in British patent 
 437,171. 
 
 The Imperial Chemical Industries Ltd. (44), in French patent 
 797,052, issued April 20, 1936, applied for October 29, 1935, in Eng- 
 land October 29, 1'934, make the same claims as in British patent 446,576. 
 
 German Patents; 
 
 Lcnricns and Fryer (55), in German patent 321,317, issued May 29, 
 1920, applied for December 21, 1915, make essentially the same claims as 
 inUnitcd States patent 1,242,955. 
 
 Lemons and Fryer (56), in German patent 327,583, issued October 11, 
 1920, applied for December 22, 1916, make essentially the sane claims as 
 in United States patent 1,242,954. 
 
 The I. G. Farbonindustrie, A. G. (40), in German patent 555,117, 
 issued July 18, 1932, applied for November 28, 1530., claims a fly spray 
 made by dissolving a fly destroying material such as amyl salicylate, 
 phenyl salicylate, pyrcthrun extract, or dorris extract in a partially 
 or wholly hydrogenated petroleum or petroleum distillation products. For 
 example, 0.4 part dcrris extract (from roots of Her ri s cllipti ca ) ' and 10 
 parts di -phenyl ether are dissolved in perhydrogonatod petroleum, 
 
 Steindorff, Pfaff, Kramer, and lorn (97), assignors to the I. G. 
 Farbonindustrie A.-G. , in German patent 594,018, issued November 12, 1932, 
 applied for July 5, 1931, claim a product for combating flics and similar 
 insects consisting of urethanes or their substitution products together 
 with extracts from pyrcthrun, or dcrris root, or synthetic insecticides. 
 
 Sichorn (24), in German patent 630,483, issued May 28, 1936, ap- 
 plied for November 22, 1932, claims the process of manufacturing .an in- 
 secticide containing dcrris extract vhich consists in extracting finely 
 divided dcrris root v/ith a dilute solution of sodium bisulphite' at 40° 
 tc 50° o., neutralizing the solution and concentrating in. vacuo. 
 
- 18 - 
 
 Exoraples are: 
 
 (1) 100 parts ground or shredded dcrris root and 100 parts of a 
 10 percent sodiun bisulphite solution arc ground 3 to 4 hours in a nill 
 at 40 to 50° C. The solution is filtered, neutralised and evaporated 
 in vacuo. 
 
 (2) 100 parts derris root arc extracted in a percolator Y7ith 200 
 parts of o. 10 percent sodiun bisulphite solution, with recirculation, and 
 the extract treated as in Exanple 1. 
 
 (3) The extraction of the derris root is carried oat in a diffus- 
 ion "battery. 
 
 The extract obtained iron derris by extraction '.7ith v/ater amounts 
 to 6 percent of the weight of the root and contains 4.23 percent rotonone, 
 whereas the extract obtained v/ith soclran bisulphite ar.ounts to 10 percent 
 of the weight of the root and contains 16.95 percent rotenono. 
 
 Tests on insects gave the follor/ing results; 
 
 Test aninal 
 
 Re sul t 
 
 
 dead stunned 
 
 
 Percent Percent 
 
 1. Derris po\7lcr*Y/ith \7atcr as 
 
 paste (10:50) Cockroaches 50 50 
 
 2. Aqueous extract of derris 
 
 root (1:50) l! - 100 
 
 3. Sodiun bisulfite extract of 
 
 dcrris root (1:50) l! 60 40 
 
 4. Aqueous extract of dcrris Japanese green- 
 root (1:50) house locusts 80 20 
 
 5. Sodiian bisulfite extract 
 
 of derris root (1:50) » 100 
 
 6. Aqueous extract of derris Stunned after 25 nin. 
 • root (1:50) Mole crickets dead after 60 ran. 
 
 7. S : odi-un bisulfite extract Stunned after 17 nin, 
 of derris root (1:50) - dead after 23 nin. 
 
 * contained 2 percent rotonone. 
 
- 19 - 
 
 Ciirorici- (15), in Ocnan pr.tcnl; 643,804, issued April 17, 1037, ap- 
 plied for Pebruary 7, 1932, claims an insecticide consisting; of on ex- 
 tract of a rotcnono-boaring root in aliphatic hydro carbons, c special 1 y 
 petroleum, hexackloroc thane, ammonium linolcate, and water. An example 
 is derris ponder 7 parts, hcxachloro ethane 12 parts, ammonium linolcate 
 •i parts, petroleum 25 parts, methyl salicylate 2 parts', and -Jatcr 50 
 parts. 
 
 The Booth Stcanship C< . Ltd. and ward Cg), in Gorman patent 646,570, 
 issue 1 . Juno 17, 1937, applied for September 11, 1935, in Great Britain 
 March 30, 1935, make essentially the sane clains as in British patent 
 •1-37,171 and United States patent 2,055,438. 
 
 Japanese Patents: 
 
 Iiba and Hakatura (42), in Japanese patent 91,478, issued May 20. 
 1931, claim a mixture of 57.6 percent trichloroethanc and 32.4 percent 
 methyl alcohol (the minimum boiling: mixture) for use as a solvent in ex- 
 tracting pyrcthrun flowers or derris root. The solvent is distilled and 
 the residue used as an insecticide. 
 
 Inai (43), in Japanese p .tent 91,645, issued June 3, 1931, patented 
 an insecticide consisting of vegetable vol '.tile oils (such as turpentine 
 or camphor oils.}, naphthalene, and extracts of derris roo.ts. 
 
 Isihara (47), in Japanese patent 91,375, issued June 20, 1931, paten- 
 ted a [process in which dried roots of plants belonging to the derris group 
 arc cut into pieces and powdered under cooling ly a special stamping 
 machine. The powder passed 1 throu ;;h a 60-nesh sieve is used as an insecti- 
 cide. 
 
 J chore Patent: 
 
 A report from 3oehringcr (5) [Japanese Pirn Claims New Process of Ob- 
 taining Toxic Substance from Derris], Assistant Trade Commissioner, Singa- 
 pore, dated March 8, 1934, stated that the ITettai Sangyo Kabushiki Kaisha. 
 of Tokyo, Japan, has been '-ranted the exclusive privilege of making, sell- 
 ing and using, in the State of Johore, an invention for "A new or improved 
 ■process of obtaining insccticidal or other toxic substances from plants 
 of the derris species." This privilege is for the term of IS years from 
 June 19, 1933. 
 
 Swedish Patents: 
 
 Wikstrom (103), in Swedish patent 85,03.3, issued April 15, 1936, ap- 
 plied for March 16, 1934, clains as an insecticide cynol [eyricnc] or its 
 derivatives. Dissolved or" suspended in cymol nay be pyrcthrun, derris, 
 quassia, rotononc, etc. 
 
20 - 
 
 Cynol can "be usee 1 , to extract the active principles of pyrothrun, 
 dc r r i s , an d quas s i a. 
 
 Other valuable components that can to use'', are chlorinated or sul- 
 fonated ethereal oils. These ethereal oils act as contact poisons. Sane 
 cxanplcs follow: 
 
 I. Derris cynol extract (15 percent) 10 parts 
 
 Adhesive 1 part 
 
 Water 1,000 parts 
 
 II. Pyrcthrun cynol extract (15 percent) 1 part 
 
 Derris Cynol extract 1 part 
 
 Hater 200 parts 
 
 III. Pyrcthrun cyr.ol extract (15 percent) 1 part 
 
 Derris cynol extract 1 part 
 
 •Quassia cynol extract 1 part 
 
 water 300 parts 
 
 IV. Pyrcthrun cynol extract (15 percent) 1-60 parts 
 Derris or 
 
 Quassia cynol extract 1-60 parts 
 
 Chlorinated or sulphonatcd ethereal oils 2-60 parts 
 Soaps or cimlsifyin." agents 200-400. parts 
 
 later 2,000-200,000 parts 
 
 A cormon nixturc consists of 
 
 Pyrethrun cynol extract (15 per- 1 .^ 
 
 cent) or Derris - or quassia cynolV 15 parts) Diluted with 
 extract ;Chlorinated or sulfonated J ^HoO to yield 
 ethereal Mis 6 parts'! .25 to 15 
 
 Soaps 79 parts ^percent solns 
 
 r/ikstrcn (104). in Swedish patent 87,625, published October 13, 
 1S36, applied for March 15, 1934, clains an insect killing natorial char- 
 acterized as follows: That it contains cynol or a '"'erivativc thereof as 
 carrier or solvent for one or several chlorinated or sulfonate c 1 ethereal 
 oils — hut not such insect or pest killing .natcrials or poisons as cxtr.acts 
 of pyre thru i, derris, quassia, or the active derivatives thcrefron. 
 
 Swiss Patent: 
 
 The P. Hoffnann-LaRocho and Co. (37), in Swiss patent 124,290, 
 issued January 16, 1928, appliod for October 5, 1926, clair. ar. insecticide 
 
- 21 - 
 
 containing the dried, pulverized root of Derris elliptica or the crude or 
 pure extract therefrom in an emulsified form. The following examples are 
 given: (1) ' One j)art crude ether extract of the roots of D. el liptica and 
 2.5 parts of a 10 percent ether solution of ozonized rape oil (obtained 
 by treating 10 parts rape oil in 60 volume parts chloroform with ozone for 
 4 hours, distilling off the chloroform, taking up the residue in aqueous 
 alcohol, and shaking the solution with ether) are dissolved in 30 parts 
 alcohol, then treated with 10 parts ether, and, to facilitate the produc- 
 tion of an emulsion, normal sodium hydroxide is added until a reddish color 
 is obtained by phcnophthalcin. • This solution is slowly and with constant 
 stirring dropped into 50 parts distilled water at 70° to 80° C. Within 
 certain limits the solution ma;y be concentrated or diluted without the 
 separation of the emulsified products. (2) One part crystallized rotcn- 
 one, that is, the purified ether soluble principle of the roots of D. 
 elliptica , together with 0.1 to 0.2 part cholcstcrinozonide, is dissolved 
 in 20 parts acetone and 10 parts ether and treated with 10 parts alcohol, 
 and, in order to facilitate omul sificat ion, sodium hydroxide is added 
 until faintly alkaline. The solution is dropped into 60 parts water at 
 70° to 60° C. with vigorous stirring, (3) One part rotonono end 0.1 
 part phytosterinoxidc are dissolved in 12 parts alcohol and 4 parts ether 
 and, to facilitate cmulsificfition, made slightly alkaline with sodium hy- 
 droxide solution. The solution is slowly dropped with stirring into 50 
 parts water at 70° to 60° C. (4) One part finely pulverized roots of 
 D. elliptica and 0.1 part ozonized cholestcrin .are treated with hot .alcohol, 
 then with 10 parts ether, and tho residue is filtered off. To facilitate 
 cmulsifi cation sodium hydroxide solution is added until the reaction is 
 faintly alkaline. The solution is slowly dropped into 60 parts distilled 
 water at 70° to 50° C, with vigorous stirring; Claim is made for an in- 
 secticide consisting of oxidation products of unsaturated fatty bodies and 
 the insecticide! constituents of the root of Derris elliptica in emul- 
 sified form. 
 
 United States Patents: 
 
 McDougall, McBougall, and SlcDougall (65), in United States patent 
 1,055,156, issued Juno 17, 1913, applied for September 3, 1911, claim 
 a composition for use as an ingredient for animal washes, insecticides, 
 and vermifuges, comprising a concentrated extract of trees of the Derris 
 
 Lly, said extract giving a red color when treated, with concentrated, sul- 
 phuric and nitric acids and a fugitive brilliant green color on the fur- 
 ther a'." - of concentrated anmohia solution, as described. The powdorod 
 dried, roots are cxtractod with a suitable solvent, .such as benzine, and tho 
 extract is evaporated to a gummy mass. A suitable extraction apparatus is 
 shown - diagramnatica.il--. For a sheep dip a mixture of 5 ounces of the com- 
 pound, and 1 pound of soft soap nay bo used, such raixturo being ad.apted for 
 use with 1.00 gallons of water; r 5 ounces of the compound ray be nixed 
 with 15 ounces yf soft soap, the mixture then being absorbed into a powder 
 by neans of sulphur to make a total weight of 10 pounds. This preparation 
 should be used with 100 gallons of water. During the manufacture of the dip, 
 
- 22 - 
 
 wash, or insecticide, a suitable water- softening reagent or reagents nay 
 be added to the composition. In like manner a suitable antiseptic or bac- 
 tericide and also a coloring natter nay be added. 
 
 Low and Hale (22), assignors to the Sow Chonical Co., in United 
 States patent 1,514,377, issued November 4, 1924, .applied for March 31, 
 1920, clain an insecticide consisting of the halohydrin extract of dcrris 
 admixed with benzyl alcohol. They also clain an insecticide comprising a 
 solution of benzyl alcohol and a halohydrin, the amount of the latter be- 
 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 fouad that the combination of ingredients 
 just described serves as an excellent solvent for various so- 
 called deadly insecticides, such as timboin, nicotine end dcrris 
 (or "Eish poison"). In utilizing such combination of ingredients 
 in this connecticn, we preferably extract the poison first with 
 the halohydrin, and admix the extract with benzyl alcohol in 
 desired proportions, depending upon specific use to be made of 
 insecticide. Furthornorc , such combination of ingredients may 
 readily be mixed with inert dry ratcrials, such as lime, lead, 
 calcium or magnesium, arsenate, and 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, makes the sane claims as in 
 British patent 214,822. 
 
 Erycr (27), assignor to McLougall and Yalding, Ltd., in United 
 States patent 1,583,681, issued May 4, 1926, applied for November 29, 
 1924, claims an insecticide comprising dcrris, a vehicle of a sulphonatcd 
 fatty body, and a colloidal addition agent. The preferred insecticide 
 consists of 1 part of derris extract to 10 to 50 parts of sulphonatcd oil 
 or wax, for example, sulphonatcd castor oil. If it is desired to use this 
 material in combination with lime-sulphur so as to produce a combined in- 
 secticide and fungicide, precipitation of the material may be prevented 
 by the addition of a colloidal agent, of which casein (5 to 20 percent) is 
 found most suitable. Powdered casein may be dissolved in warm sulphonatcd 
 oil. 
 
 The active principles of dcrris arc extracted with benzene or 
 other suitable volatile solvent. An extract of pcrkakal nay be similarly 
 used. The sulphonated oil ray be sulphonatcd sperm oil. This insecticide 
 may be used alone or in admixture with lead arsenate and bordeaux mixture. 
 
 Lennis (17), on April 16, 1923 filed application for United States 
 patent 1,621,240, which was granted him on March 15, 1927. This patent 
 covers "the use as an insecticide and vermifuge rf ground cube root with 
 
- 23 - 
 
 the fibrous element removed. Cube is stated to "bo a woody shrub found 
 in Pern and other South American countries which is classified by some 
 
 native botanists as of the family Solanaceae. Directions are given for 
 preparing a solid e::tract of cube by grinding the roots or plants, de- 
 tracting with a suitable solvent such as benzol, or alcohol, filtering, 
 and evaporating. The solid extract has a light strav; color and is odor- 
 less and tasteless. 
 
 "For i dent if i cat ion, the powder nay be subjected to the 
 action of concentrated sulphuric acid and dilute nitric acid, v/hcre- 
 upoh it gives a bright clear red color. By the addition of po- 
 tassium hydroxide in nearly equal vol 'one, a vigorous action is 
 obtained, and the solution turns to a yellowi sh -pink. A further' 
 addition of potassium hydroxide produces a stable brown solution. 
 
 "The compound in the form of powder or dust nay be used as 
 an insecticide with talcum powder, cornstarch or other carrier. 
 It is very effective against flies, reaches, and other insects. 
 It is uy belief that the powdor sots up an irritation of the 
 breathing apparatus which results in early death. 
 
 "The compound can bo used with water or with soap and water 
 or other emulsifying agent, as a wish or spray for plants, animals, 
 or trees. It is effective against aphids, beetles, sono insects, 
 and worms. 
 
 "It can be used as an extract with alcohol for similar pur- 
 poses, for instance as a v:ash for ticks on cattle. 
 
 "As an alcoholic extract, tests show the solution to have 
 slightly greater effectiveness when sprayed on the cotton aphid. 
 than nicotine sulphate. Experience shows that it is eight tines 
 as effective as similar dcrris extract. 
 
 "The proportions of the compound and the carrier nay be 
 
 varied as desired for different purposes. 
 
 "For certain purposes, it is desirable to use the alcoholic 
 extract in a soap and water omulsif ication. A suitable solution 
 for aphids car. be made by using the extract from one- third pound 
 of powder in one hundred gallons of soap solution." 
 
 In a reissue of this patent (reissue 18,667 of November 22, 1932, 
 applied for February 25, 1929) Dennis (.18) corrected the information con- 
 cerning the botanical origin of cube given in his original patent 1,521, 
 240, stating: "While the exact botanical classification of the plant is 
 not -altogether certain it is believed to be a species of the genus Loncho- 
 earpus of the family Lcguminosae." 
 
 Takei (98), assignor to Zaidan Hojin Rikaguku Konkyujo, in United 
 States patent 1,724,626, issued August 13, 1929, applied for August 31, 
 
- 24 - 
 
 1925, in Japan, September 8,. 1924, claims the process of producing a 
 liquid insecticide containing the effective- ingredient of the derris specie 
 which comprises extracting raw material containing the aforesaid .ingred- 
 ient with a volatile organic solvent therefor, nixing the extract with an 
 anhydrous alkali-free organic preservative for the ingredient, evaporating 
 the solvent fro." the mixture and nixing the resulting product with an or- 
 ganic colloidal material in an aqueous medium. Examples arc: (l) A so- 
 lution of 10 liters of ether added to 10 grans of rotenonc, is nixed with 
 a mixture of 400 grans nf fish )il r/i th 40 grans of hard oil. After suf- 
 ficient agitation, all or the greater part of the other is recovered by 
 evaporation anc 1 condensation and thereby a soni-solid mixture is obtained 
 as a primary material. Five hundred grans of soap are nixed with 100 kilo- 
 grams of water tn prepare a colloidal aqueous solution as a secondary mater- 
 ial. In use, the primary reagent is nixed with the colloidal aqueous solu- 
 tion and it may be suitably diluted with addition of 100 kilograms of water 
 when used as insecticide. The colloidal solution or secondary reagent nay 
 ■be prepared at any tine by the users. (2) Ten liters of ether are added 
 to 1 kilogram of the derris root. After 4 days, the extract is add.cd to 
 400 grans of chrysalis oil and 100 grams of lard. After evaporating the 
 ether, a semi-solid, substance is obtained as a primary reagent. The prepar- 
 ation of the secondary reagent is sane to that of example 1. (3) [Twenty 
 liters of petroleum ether are .added to 1 kilogram of derris root. After 4 
 days, the extract is added to 200 grans of beeswax .and 50 grans of pine 
 resin. After solution, the larger portion of the petroleum ether is re- 
 covered by evaporation and condensation and thereby the semi-colloidal 
 material is obtained as the primary material or reagent. The secondary 
 reagent nay be prepared by adding a colloidal solution in which 200 grans 
 of soap are dissolved, in 100 kilograms of water, 
 
 Takei attributes the poor qualities of rotenone insecticides on the 
 market to the combined action of alkali and water. A superior product is 
 made by mixing rotenone with one or more kinds of oils, fats, waxes, resins, 
 higher hydrocarbons, higher alcohols, higher fatty-acids which arc entirely 
 free from water and alkali to form a static preservative nixturc and this 
 mixture is nixed with colloidal aqueous solution such as soap water in use. 
 
 Rotenone nay be extracted v/ith such solvents as methyl alcohol, 
 ethyl alcohol, ether, petroleun ether, chloroform, or carbon tetrachloride. 
 The oils mean all kinds of animal oils, such as sardine oil, herring oil, 
 cod-liver oil, shark oil, chrysalis oil, :r a vegetable oil, such as coconut 
 oil, bean oil, rapeseod oil, and castor oil. The fatty oil nay be a mater- 
 ial such as lord, beef tallow, animal hard oil, and vegetable hard oil. 
 Waxes, such as wood wax, and beeswax nay be used, also resins, such as pine 
 resin, and copal. Higher alcohol includes glycerin, and higher hydrocarbon 
 means paraffin, etc. 
 
 Colloidal aqueous solution includes solution of soap, glue, egg- 
 albumin, bean milk, dextrine, starch, bengal isinglass, animal albumin, etc. 
 Sometimes to said .aqueous solution is r.CC.cc. a little quantity of methyl al- 
 cohol, ethyl ale .hoi, chloroform, ether, camphor oil, lemon oil, and other 
 solvents. 
 
- 25 - 
 
 Ohori and Uakazawa (78), assignors to Zaidan Hojin Rikagaku Kcnkyujo, 
 
 in United States patent 1,745,907, issued February 4, 1930, applied for 
 February 10, 1928, in Japan, February 18, 1927, claim a process for pro- 
 ducing a liquid insecticide containing the effective ingredient of derris 
 species, which comprises foming a prinary material in which the effective 
 ingredient is nixed v/ith an anhydrous and alkali-free material of an oily 
 nature and dissolved in an anhydrous solvent such as "benzol, carbon tetra- 
 chloride, or trichl ore ethane, -and then nixing the prinary naterial with a 
 soap solution to form a colloidal solution. Examples arc: (l) To 100 
 grans of powd.cred derris root, 10 liters of ether arc added to extract the 
 effective ingredient of the derris root. After extraction is conplcte, the 
 whole or greater part of the ether is evaporated .and recovered. To the 
 residual effective ingredient a nixture of 150 grans of anhydrous and al- 
 kali-free fish oil and 150 grans of benzol (as the anhydrous solvent) arc 
 added, so that a solution of the effective ingredient in benzol results. 
 Txiis is the inproved ^urinary naterial. The soap solution is easily pre- 
 pared ~oy, for instance, adding 500 grans of soap to 100 kilograns of water. 
 The soap solution is nixed with the inproved prinary naterial before use, 
 (2) To 1 kilogran of powdered derris root, 5 kilograns of benzol are ad- 
 ded and the effective ingredient >f the derris root is extracted while 
 warning the benzol. The benzol is recovered by evaporation. ™o the resi- 
 dual effective ingredient, a nixture of 600 grans of anhydrous and alkali- 
 frcc fish oil and 600 grans of carbon tetrachloride (as the anhydrous sol- 
 vent) arc added to fori: a solution of the effective ingredient. This is 
 the inproved prinary naterial. The soap solution nay bo the sane as exem- 
 plified in Example I. Trichloroothanc as the anhydrous solvent can be 
 user" as well. Also in the two examples given, the inproved primary naterial 
 can be eo,sily -prepared in the forri of powder when 800 grans of anhydrous 
 gun arable arc added. 
 
 O'Xane (79), in United States patent 1,786,125, issued December 23, 
 1930, applied for Hay 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, derris 
 of various species, or other substances that will furnish on additional 
 killing agent effective against insects. Or, such materials may be added 
 to the refined oil. The colloidal metal derivative may be, for example, 
 colloidal cuprous oxide. 
 
 Sanders (84), in United States patent 1,803,870, issued. Hay 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 proportion of the casein compound being not. less 
 than 1 pound of actual casein to 2 pounds of the metallic metal. 
 
 "In making up a paste copper fungicide it is preferable to 
 add 4 lbs. of casein or 10 lbs. of calcium cas'oinate to 50 lbs. of 
 po.ste formed by adding 25 lbs. of calcium hyd.roxido and 25 lbs. of 
 copper sulphate to 50 gals, of water and filtering, as otherwise 
 
- 26 - 
 
 some of the colloidj.il. copper would "be lost in t] o filter water. It 
 will be understood, furthermore, that the above mixtures nay be ad- 
 ded to other insecticides or fungicides, either before or after 
 causing then to react in water. Fir example, dry arsenical con- 
 pounds or dcrris or pyrethrun or other insocticidal powders nay 
 be added to the dry mixture of the copper compound and the casein 
 compound, or various fungicides or insecticides, such as emulsi- 
 ficd oils, nicotine or derris corrpounds, etc., nay be nixed with 
 the wet colloidal copper mixture." 
 
 Linglcr (5?), in United States patent 1,820,394, issued August 25, 
 
 1931, applied for March 9, 1929, in Germany, March 3 2, 1923, assigned to 
 the Doutschu Goseilschaf t fur Schadlingsbokampfung M.3.H. of Frankfort-on- 
 thc-lla.in., Germany, chains a method of fumigating which consists in con- 
 verting a cyanide of a netal selected from the group comprising alkaline 
 earth metals and magnesium, into shaped bodies ">f a size the hydrocyanic 
 acid content of which corresponds to the amount required for funigatirg, 
 reducing the shaped bodies into powder, and blowing the said powder into 
 the sj^acc to be fumigatod. 
 
 "According to one method of carrying ny invention into effect 
 other auxiliary substances, for example, such as arc also capable 
 of acting "upon the vermin to be destroyed, as -for example, nicotine 
 or suitable nicotine compounds, as for example, nicotine sulphate, 
 pyrethrun, derris root or stimulating or preventative substances, 
 which volatilize simultaneously with the hydrocyanic acid which is 
 given off .may be incorx'orated with- the pulvcrous alkaline earth 
 cyanid.e compounds or the shaped bodies to be produced the re fro:-.." 
 
 Sanders (85). in United States patent l,84?,54(i, issued March 1, 
 
 1932, applied for March 11, 193'), chains a method ^f coating particles of 
 insecticide dust and causing them to become floatable on water by utilis- 
 ing the heat of slaking lime for melting stearic acid to coat the par- 
 ticles. Sufficient water is added to quicklime to convert all or a por- 
 tion of it to hydrated lime. 
 
 "This water may corr t , ; in suspension or in solution a poison 
 or the poison may be added separately cither before or after the 
 water. While the ma.ss is hot and being agitated I add a fatty 
 acid enough to coat most of the particles in the mass and render 
 then floatable. The fatty acid nay be mixed with either the lime 
 or the poison either before or after adding the water t n the lime 
 without departing from the spirit of the invention. I then grind, 
 and air float in a suitable mill. An example of the proportions 
 used is: 300 lbs. quicklime, 300 lbs. paste copper arscnitc. 
 When at its maximum heat and under agitation add 12 lbs. of stearic 
 acid. This mixture should be ground before using to get the best 
 results but may bo .user 1 directly." "Other insecticides other than 
 arsenic may he used as finely ground pyrethrun, hellebore, derris, 
 nicotine dust, etc." 
 
- 27 - 
 
 McGill (7?), in United States patent 1,854,943, issued April 19, 
 1932, applied for November 7, 1927, claims a solution containing ro- 
 tenone adapted for use in the mothproofing- of fabrics, lie also claims a 
 mothproofing solution containing an extract of derris, or of haiari. 
 
 "The invention will be readily understood from the following exam- 
 
 pie. 
 
 o 
 
 "One pound of derris root is ground to a 'powder and admixed with 
 one gallon of petroleum naphtha, boiling between approximately 300 and 400 
 F. Tnc mixture is allowed zo stand at room temperature for a considerable 
 
 riod, for example, five to seven days, being occasionally agitated during 
 this peri >d. The hydrocarbor. oil containing the desired active principles 
 of the derris root in then removed, filtered clear and, if desired, minute 
 amounts of essential oils or other suitable odoriferous substances may be 
 
 "I:, preparing the extract, if it is desired bo hasten the operation, 
 the mixture of cil and powdered root may be heated mildly, say to a temper- 
 ature of 150 to 200° I. , and cJ:h period required for the extraction of the 
 ac.tivt principles by the oil is thoreb" substantially reduced, s,r to 24 
 
 or 36 Lours. 
 
 "Extracts of haiari na;> be produced in the sane manner. In 
 using black haiari, it is preferred to extract both the roots and 
 stem, while in the case of white haiari, it is -preferred to extract 
 the stem and leaves. 
 
 'The solution produced as described is particularly suitable 
 for ase by dipping the fabrics therein, pressing out e:;cess solution 
 and drying. In this Way, rotenonc is distributed over every fiber 
 of the fabric, which is thereby rendered moth proof for a considcr- 
 ablc tine. The moth proofing dip may suitably be the last step in 
 a dry cleaning operation. 
 
 "Where it ic; desired to apply the active principle by means 
 of a spray, it is referred to employ a higher boiling naphtha cut, 
 for example, one boilin between 450-5.50° F. , since the slower 
 evaporation of such naphtha permits a more complete penetration of 
 the extracts into ever:/ portion <f the fabric or garner t "hich 
 night not bo directly exposed to the spray. 
 
 "While it is preferred to employ petroleum naphthas as the 
 extracting fluid, it mart be understood that the invention is not 
 intended to be limited in this respect since alcohol, benzol, other, 
 and other similar organic solvents are also effective in extracting 
 and holding in solution the active principles of derris root and 
 other substances containing rotenonc* 
 
- 28 
 
 "Rotenone has important properties which render it invaluable 
 as a mothproofing agent. It can be applied with great ease. It 
 has no pronounced or objectionable odor. It is of relatively low 
 volatility so that it persists n the fabrics for a. considerable 
 tine. It is highly toxic and repellent to the noth larvae, but is 
 non- injurious to hunan beings and warn blooded animals." 
 
 Jones (49), in United States patent 1,928,256, issued September 26, 
 1933, applied for August 23, 1930, clains an insecticide comprising water, 
 rotenone colloidally dispersed therein, and a snail proportion, of a pyridine 
 base. For example, 1 gran of pure rotenone is dissolved in 100 cc. of 
 pyridine. One cc, of this solution is added to 100 cc. of distilled water 
 and shaken gently. A pale opalescent colloidal solution results which shows 
 no evidence of separation over on extended period of tine. The various 
 ncthyl pyridines (alpha, beta, and gamma pi col ines), the dinethyl, trinethyl, 
 ethyl, allyl, and other alkyl-pyridinos nay be employed in place of pyridine. 
 Similarly the dipyridyls and other compounds containing a pyridine nucleus 
 nay be used. These compounds arc included raider the tern "pyridine base". 
 In plo.ee of pure rotenone, a crude rotenone, or an extract of a plant con- 
 taining rotenone nay be used. For example extractives iron Derris elliptica , 
 Loncho carpus , and other plants known to contain r >tenone nay be employedg 
 
 Jones (50), in United States patent 1,928,968, issued OctoDor 3, 
 1333, applied for August 23, 1930, clains a process of producing a liquid 
 insecticide containing rotenone in a colloidal state of dispersion which. 
 consists in dissolving rotenone in acetone, and adding this solution to 
 water in the presence of tannic acid with subsequent nixing. For example, 
 4 grans of pure rotenone and 2 grams of tannic acid U. S. P. .are dissolved 
 in 100 cc. of acetone, a clear solution resulting. Two and one-half cc# 
 of this solution is added to 1,000 cc, of distilled water and shaken gently. 
 An opalescent colloidal solution results which shows no evidence of separ- 
 ation during an extended period of tine. In attempts to form suspensions 
 such solvents as acetic acid, acetone, diacetone alcohol, ethyl alcohol, 
 ethyl formate, ethylene chlorohydrin, and pyridine have been tried. With 
 the exception of pyridine, none of these gave satisfactory suspensions when 
 no protective colloid was added. Acetic acid, ethyl alcohol, ethyl formate, 
 ethylene chlorohydrin, and pyridine did not give permanent dispersions in 
 the presence of a protective material such as tannic acid. Acetone and 
 diacetone alcohol, on the other hand, have been found to give very satis- 
 factory results when used in the presence of the proper amount of suitable 
 protective natcrial. 
 
 Experiments have been made to test the efficacy of a number of pro- 
 tective colloids for this purpose, the protective natcrial being dissolved 
 or suspended in water and an acetone solution of rotenone .added. Avtong 
 these were gum acacia, gun karaya, gun ghatti, gelatin, starch, agar-agar, 
 saponin, tannic acid, tricthanolanine oleate, ammonium alginate, potassium 
 oleate, calcium caseinato, diatomaceous earth, bentonite, and lithoponc. 
 Tannic acid was found to be the most suitable material as regards suspending 
 or protecting power, as well as from the standpoints of solubility and cost. 
 
- £9 - 
 
 I/, place of acetone -.ethyl ethyl ketone, diethyl ketone, methyl ethyl 
 acetone and acetyl acetone nay be used. In like manner such aryl com- 
 pounds as phenyl ethyl ketone and o- or n-phenyl tolyl ketone nay he 
 employed in place of acetone' or di-acctono alcohol, lo plo.ee oz pure 
 roter.one, a crude rotcnoric, or an extrr.ct of a plant containing rotenone 
 nay be used. For example, extractives fron Derris elliptica, lonchoca rpus 
 and other plants known to contain rotenone nay he enployed. 
 
 Grant (32), in United States patent 1,934,057, issued November 7, 
 1933, applied for October 31, 1328, assigned to the Standard Oil Develop- 
 ment Company, claims an insecticide or insect repellent comprising a pe- 
 troleum white oil, derris cxtro.ct, and on emulsifying a; cnt. The derris 
 roots arc extracted with a volatile solvent, such as benzol, isoprOpyl 
 alcohol, etc. The extraction nay be carried out by any of the known 
 methods, such as percolation, maceration, etc. This method is especially 
 is apted to prepare concentrator" extracts end consists of causing the sol- 
 vent to flow over and through the substance to be extracted without flooding 
 it. The volatile solvent is then evaporated partially or wholly, prefer- 
 ably in vacuo, leaving a concentrated derris extract. The latter is then 
 emulsified with a petroleum oil, preferably of the kind known as white 
 oil, and nado by intensive acid treatment of gas-oil or lubricating-oil 
 fractions, such as machine oil, transformer oil, light or medium lubricat- 
 ing oils, etc. The ermlsification nay he carried out by dissolving an 
 emulsifying agent, ouch as s^op, in the white oil and feeding it, together 
 with the dry derris extract, into a colloid mill to obtain o, stable envi- 
 sion. Some water may he thoroughly adnixed with this product before mar- 
 keting. 
 
 Another method, which may often be use'' with advantage is the fol- 
 lowing. The insecticidal or active principles Df the derris root are ex- 
 tracted directly with the "white oil." Volatile solvents such as alcohols; 
 ethers; esters; ketones, for instance acetone; :~ro, v?tic hydrocarbons, for 
 instance benzene; or chlorinated hydrocarbons nay he added to the white 
 oil to increase its solvent power. In this case, however, it is preferable 
 to distill off subsequently most of the volatile solvents from the product 
 obtained. A similar result may he obtained by adding steam distilled pine 
 oil, torpincol, phenol, cresol, or their honologs, cyclohcxanol and its 
 hon.oiogs hydrooenatcd naphthalenes such as tetralin or decalin, chlorinated 
 napthalones inch as holowox oil, etc., to the white oil to increase its 
 solvent power for the derris extractives. The ingredients just mentioned 
 cannot end snould not he renovod by subsequent distillation bat remain in 
 the product and confer upon it a fungicidal and bactericidal effect in o.d- 
 dltion to its insecticidal properties and facilitate its ermlsification. 
 The derris-white oil extract is then mixed with on cnulsifyirp; agent, such 
 o.s fatt; soon, rosin soap, saponin, soaps of petroleum sul phonic acids, 
 soaps of sulplionatcd vegetable or animal oils, to form a composition cepable 
 of dispersing in water. Any one soo.p nr a mixture of several soaps may he 
 used. Po.rt of the soap may be added, to the white oil before the extraction 
 because it has been found that the presence of a soap facilitates the ex- 
 traction. Oil-soluble s.lph- notes are preferably usee as an emulsifying 
 agent, and arc obtained 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, emulsifier 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, 40-30 percent white oil, 5-25 
 percent soap or other emulsifior and fungicide, 0-35 percent water. Usually 
 the percentage of the derris extractives 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 derris 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, cabbage 
 worm, sawflies, etc. 
 
 An example of preparing this insecticide is as follows: 
 
 Two kilograms of ground derris roots were 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 resin. Eighty grams of this extract 
 were fed into the colloid mill together with a solution of 750 grans of oil 
 soluble sodium solphonato in 2.5 liters of "Wyrol" , a commercial brand of 
 white oil. Viator was also added in the amount of 1.5 liters. A thick 
 emulsion resulted similar in appearance to mayonnaise and ready for marketing. 
 Part of this preparation was diluted with 50 times its weight of water and 
 gave a final spray which was effective when sprayed on tru^s as an insecticide. 
 
 Badertschor {?,) , assignor to McCormick & Co., Inc., in United States 
 patent 1,938,652, issued December 12, 1933, applied for August 20, 1951, 
 claims a horticultural spray including pine oil, an insecticide, and dipen- 
 tane, the dipentone being present in amount in excess of the amount normally 
 present in pine oil and in quantity sufficient to substantially negative 
 the tendency of the pine oil to burn foliage. Any suitable insecticide nay 
 be included as, for example, nicotine or nicotine sulphate, rotonone.pyrethrine 
 as an extract of pyrethrum flowers, quassiin as an extract of quassia chips, 
 etc. 
 
 Grant (33), assignor to Standard Oil D G velopment Co., in United 
 States patent 1,940,645, issued December 19, 1933, applied for October 19, 
 1927, clai'-s in the manufacture of insecticides, the irprovement which 
 comprises extracting the active insecticidal principles from vegetable mut- 
 ter of the group consisting of pyrethrum, derris, cube, and tophrosia, with a 
 
- 31 - 
 
 mixture of an organic solvent, a blending agent and an emulsifying agent. 
 Preferred organic solvents are naphtha, kerosene, and light lubricating oil. 
 Suitable blending agents are: oil soluble sulphonates, Turkey rod oil, rosin 
 soap, sulphonsvtod vegetable or r.incral oils, steam distilled pine oil, t orpin- 
 col, crcsol, cyclohcxanol, dichloro benzene, chloronaphthalone, one or more 
 of the higher alcohols, such as isopropyl or secondary butyl or secondary anyl 
 alcohol, ketones, or cyclohcx-nol or its honolognes. Sonc of the above 
 materials nay servo both as blending agents and as emulsifying agents. Such 
 materials having this dual property are oil soluble sulphonates, Turkey red 
 oil, su.lphor.ated vegetable or animal oils and to a certain extent also rosin 
 soap. The active principles nay be extracted with other solvents, for exam- 
 ple, alcohols (ethyl, isopropyl, etc.), benzol, or carbon tetrachloride. The 
 extract so prepared may be concentrated to yield an oloo- rosin which may be 
 mixed with oil-soluble sulphonate in suitable percentages. Various substances 
 may be added to the composition either before or after the organic material 
 is extracted, and before or after concentration by evaporation or distillation. 
 Phenol-.,, cresols, pine oil, etc., arc suitable for this purpose. Illustra- 
 tive composite solvents arc: (l) kerosene 31.6 cc, oil-soluble sulphonate 
 18.4 cc, water 2.0 cc; (2) kerosene 31.6 cc, oil-soluble sulphonate 13.4 
 cc, secondary butyl alcohol 10.0 cc, water 68.0 cc; (3) kerosene 31.0 cc, 
 ^il-soluble sulphonate 1S.0 cc, ethyl methyl ketone 10.0 cc, water 35.0 cc; 
 (4) petroleum white oil (vis. 75-85 sec. Saybolt at 100° p.) 45.0 cc, oil- 
 soluble sulphonate 5.0 cc, dichlorobenzene (crude) 9.5 cc, water 2.0 cc; (5) 
 mineral seal oil 171.3 cc, oil-soluble sulphonate 30.2 cc, potash rosin soap 
 10.0 g. , licxahydrophonol 10.0 cc, ethyl -ethyl ketone 10.0 cc, crcsol, U.S. P., 
 10.0 cc, water 24.0 cc; (6) petroleum white oil (vis. 75-85 sec. Saybolt at 
 100 p.) 128.0 cc, oil-soluble sulphonate 14.2 cc, secondary amyl alcohol 
 6.6 cc, steam distilled pine oil 6.6 cc, chloronaphthalenes (crude) 6.6 cc, 
 potash rosin soap 8.6 gm. , water 17.5 cc. 
 
 Badertscher (3), assignor to McCormick & Co., Inc., in Unite'. States 
 patent 1,940,899, issued December 25, 1933, applied for January 21, 1932, 
 claims the method of producing a horticultural dust which includes spraying 
 a non-alkaline inert material in finely divided form with the active prin- 
 ciple of pyrethrum in solution in a volatile solvent while agitating the 
 inert Material and maintaining it at a temperature at which the solvent will 
 evaporate. 
 
 Hie non-alkaline inert material nay be a siliceous earth, talc, benton- 
 ite, etc. The active principle of pyrethrum may be used in admixture 
 wit/, rotenone. A horticultural dust made in accordance with this invention 
 nay comprise 80-95 inert material and 5-20 pyrethrum, or pyrethiun and ro- 
 tenone, and the coated, impregnated, inert material may, if desired, be ad- 
 mixed with ground derris root or ground cube root in the proportion of 60 
 parts inert material to 40 parts of around derris or cube root, or a mixture 
 thereof. 
 
 Jones (51), in United States patent 1,942,104, issued January 2, 
 1934, applied for February 20, 1933, claims a process for making a chemical 
 compound of rotenone and carbon tetrachloride which consists substantially 
 
 in extracting the roots of plants of the genus DcTuelia ( Derris ) with warm 
 carbon tetrachloride, and crystallizing. Roots of Lonchocarpus or Soatholobus 
 nay be used likewise. 
 
_ 3^ - 
 
 For example 50 grams of the roots of Deguelia ( De rri s) 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 needlelike crystalline product dried in 
 the air. The solvate C 23 E 22 6 .CC1 4 contains 71.9 percent by weight of ro- 
 tenone and has highly valuable properties as an insecticide, and mothproofing 
 agent • 
 
 Kills and Fayerweathor (75), assignors to the D077 Chemical Co. in 
 United States patent 1,942,827, issued January 9, 1934, applied for March 27, 
 1933, claim 1, 2- dihydroxy-4- tertiary alkyl benzene, especially the tertiary 
 butyl and tertiary arayl derivatives. As little as between 0.001 and 0.05 
 percent of these compounds in gasoline inhibits gam formation. These new 
 compounds may also bo employed as stabilizers for insecticide compositions, 
 such as pyre thrum and rotenone. They may also be used as antioxidants in 
 vegetable and animal fats, waxes, soaps, etc. 
 
 Hailer and Schaffer (34), in U. 3. patent 1,945,312, issued January 
 30, 1934, applied for April 10, 1933, claim the process of making di-hydror- 
 otenone which comprises hydrcgenating a ro ten one- bearing plant extract 
 dissolved in an organic solvent in the presence of a nickel catalyst obtained 
 by alloying equal parts of nickel and aluminum and then dissolving out the 
 latter with aqueous sodium hydroxide. Benzene, acetone, ethyl acetate, and 
 ether are suitable solvents. The reaction proceeds at atmospheric pressure 
 and at room temperature and the yield of di hydro rote none is about 90 percent 
 of the theoretical. 
 
 F^r example 50 grams of the ground root of Deguelia (Derris) sp. 
 (tuba root) is exhaustively extracted in a continuous 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 grams of nickel catalyst 
 suspended in 10 cc. ethyl alcohol arc added. The apparatus is evacuated, 
 then filled with hydrogen and the mixture is shaken with hydrogen until the 
 rate of absorption of hydrogen is very slow. The solution is decanted from 
 the catalyst, filtered, and concentrated to a small volume, and 10-25 cc. 
 of ethyl alcohol are added. After standing for a short time the crystalliza- 
 tion of dihydro rotenone is usually complete. The product is practically pure 
 dihydro rotenone. 
 
 Bousquet and Tisdale (ll), assignors to S. I. du Font dc Nemours & Co., in 
 United States patent 1,954,517, issued April 10, 1934, applied for July 8, 
 1932, claim the method of killing insects which comprises contacting the 
 insects with a water emulsion of beta beta-dichlordiethyl ether and an in- 
 secticide of the group consisting of water-insoluble dithio carbamates, water- 
 insoluble thiuran sulphides (especially tetraethyl thiuram nonosulphido) 
 and the toxic ingredient of derris root. 
 
 Examples are: 
 
- 33 - 
 
 hasturtium plants infested with "black aphids were sprayed v;ith a 
 soap emulsion containing 0.1 percent of a solution composed of 10 percent of 
 the toxic ingredient from derris root and 90 percent beta beta-dichlordiethyl 
 ether. .After 24 hours, norc than 99 percent of the aphids wore dead. 
 
 Cannon houseflios were sprayed with kerosene containing 2 percent of 
 a beta beta-dichlordiethyl ether extract of derris root. Approximately 90 
 percent of the flics were paralyzed in 6 minutes and 90 percent wore dead 
 in 24 hours* 
 
 Dougherty, and Anderson (21), in United States patent 1,963,338, 
 issued June 19, 1934, applied for May 23, 1933, described a portable sprayer 
 which uses steam generated by an electric, heating unit to expel insecticidal 
 fluids. Eotenonc is mentioned as a botanical derivative which can be used 
 in such an insecticidal composition. 
 
 Fulton (23), assignor to Stance. Inc., in Urn ted States patent 1,967,024, 
 issued July 17, 1934, applied for June 6, 1929, claims an insecticide com- 
 prising pyrethrins .and the .active extract containing rotonono obtained from 
 a plant. For example pyrothrun extract is pre, ared by extracting pyre thrum 
 flowers with 8 times their weight of kerosene and decolorizing the obtained 
 solution 7/i th 3 percent of its weight of chemically prepared absorptive clay, 
 such as "Filtrol". This is improved by dissolving 0.025 percent by weight 
 of rotenone in the extract. In case it is desired to dissolve a higher per- 
 centage of rotenone it is necessary to use a mixed solvent. If for instance 
 1 percent "oy weight of chloroform is added to the pyre thrum-kerosene extract 
 0.1 percent by weight of rotenone is soluble in it, i.e., four times as much 
 as in the absence of chloroform. A benzol extract of derris may be used in- 
 stead of pure rotenone. Carbon tetrachloride is also mentioned as a solvent. 
 
 Bousquet (10), assignor to the Grasselli 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 containing technical 
 soya bean lecithin as the essential active ingredient and sulphonated fish 
 oil or butyl alcohol or other ingredients as a dispersing agent. It is stated 
 lecithin preparations are compatible with other contact insecticides such as 
 nicotine, rotenone, and pyrcthrum preparations. 
 
 Janes (43), assignor to C. P. Byrnes, Trustee, in United States 
 patent 2,006,456, issued July 2, 1935, applied for March 12, 1930, claims 
 in the process of treating sulphonated products obtained by treating lighter 
 petroleum fractions such as gasoline with sulphuric acid to obtain an emul- 
 sifiable insecticide or fungicide, the steps consisting of neutralizing the 
 sulphuric and sulphurous acids present by adding a strong solution of a 
 water-soluble alkali capable of said neutralization, removing the neutralized 
 acid, then agitating the remaining mass with a weaker alkaline water solution, 
 decanting and removing the water solution, then washing the remainder to re- 
 move excess alkali, and then adding a small percentage of an insect poison. 
 The insect poison may be nicotine, derris root, or other organic poisons, or 
 .inorganic poisons such as copper and arsenic derivatives. 
 
- 3-1 - 
 
 Voorhees (99), assignor to the Standard Oil Company of Indiana, in 
 United States patent 2,011,428. issued August 13, 1935, applied for May 4, 
 1931, claims "an insecticidal and fungicidal composition comprising a 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-screening 
 oil-soluble organic compound selected from the class consisting of r 'jnino an- 
 thraqui nones. " . ■ ■<■ . 
 
 "Also di- amino and substituted di-amino anthraqui nones m?.y be used. 
 The nucleus of the anthraquinone and the organic residue may be substituted 
 with alkyl, aryl, aralkyl, nitro, hydroxyl' and other groups. The above 
 class of anthraquinone compounds include phony lated amino anthraquinone, 
 oxpheiiyl -minoanthraquinonos, alkyl phenyl ami no. anthraqui nones, diary lamino 
 anthraquinone s, 1,4-toluido anthraquinone and aryl diamine anthraqui nones. " 
 
 "'The following specific example of a concentrated emulsion suitable 
 for dilution to yield an insecticidal or fungicidal spray is as follows: 
 Gum ghatti , 2.4 percent; cresylic acid, 0.18 percent; water, 35 p rcent; white 
 oil (30 second Saybclt at 100°. P.), 62.4 percent; and 1,4-rtoluido anthra- • 
 qui none, 0.02 percent. The concentrated emulsion may be prepared oy intimately 
 mixing the ingredients in a colloid mill or by passing the mixture through 
 a centrifugal pump or in any other suitable manner, to give .a concentrated 
 emulsif iablc composition which nay readily be diluted to yield an emulsion 
 sui t ab 1 e f o r sp r ayi ng pu rp o s e s . " 
 
 "The oil may contain the active principles uf pyrethrum or other 
 "oil-soluble organic insecticide of vegetable origin" [e.g. dcrris extract.] 
 
 Buc (12), assignor to Standard Oil Development Co., in United Strtes 
 patent 2,013,028, issued September 3, 1935, applied for March 12, 1931, claims 
 an insecticidal composition consisting of a non-volatile viscous petroleum 
 oil containing not less than 0.1 percent of insecticidal material selected 
 from the group consisting jf rotenone and rotenoils and not less than 1.5 
 percent of a non-volatile highly halogenated hydrocarbon. Buc defines ro- 
 tenoios as the insecticidal principles of certain fish poison plants such 
 as debris and cube which are not exactly identical v/ith rot one no in their 
 chemical constitution but have a similar insecticidal action. A suitable 
 insecticide may be made by dissolving 1 gram rotenone, 20 grams halogenated 
 naphthalene of specific gravity 1.25 in 1 liter kerosene. Other examples 
 arc: (l) 2 grru; rotenone, 30 grams halogent tec! naphthalene (halowax oil) 
 of specific graviuy 1- -o in 1 liter light lubri2a ! :ii:g oil; (2) 1.5 grams 
 rotenon, 25 grams of chlorinated gasoline contriving 50 .percent of chlorine in 
 1 liter of petroleum oil having a gravity of 27° A.P.I, and a viscosity of 
 115 Saybolt at 100' P.; (3) an aqueous emulsion containing 0.7 porcent of 
 the composition given in Example 1. 
 
 Schotte and Gornitz (90), assignors to Schering-Kalilbaum A. G-, of 
 Berlin, Germany, in United States patent 2,024,392, issued December 17, 1935, 
 applied for December 12, 1933, in Germany, November 13, 1931, claim an insecti- 
 cidal preparation consisting of a mixture containing rotenone and ver-.trin. 
 
- 35 - 
 
 They also claim an insocticidal preparation consisting of a mixture con- 
 taining 2.5 parts radix derridis ellipticac and 7.5 parts somen sabadillae. 
 The. patentees state that by combining one of these drugs containing rotenone 
 with :. drag containing veratrin, for instance saba&illa seed or an extract 
 or alkaloids recovered from such products, an insecticidal effect is ob- 
 tained, which is far grea-ter than the effects exerted by the two drugs if 
 used singly. 
 
 "That this is true, is shown by tho following comparative 
 tests made by using strcwable preparations consisting of intimate 
 ground mixtures of semen sabadillae with talc, radix derridis ellip- 
 ticac with talc and with a mixture of semen sabadillao and radix 
 ierridis ellipticac. In each test 30 caterpillars of Tephrocyistia 
 absinthiqta CI. (G-eometridae) placed on blottong paper were dusted 
 with a quantity of one of the mixtures corresponding to .15 mil- 
 ligram ;.er square centimetre, the powder being even distributed. 
 
- 36 - 
 
 Preparation De f?, 
 
 caterpillars 
 
 Number of 
 laterpillai 
 not killed 
 
 Talc 4 2.5$ dorr in root 1 29 
 
 Talc + 5$ dorris root 10 20 
 
 Talc + 7.5$ derris root 18 12 
 
 Talc + 7.5$ sabadilla soed 17 13 
 
 Talc + 10$ sabadilla seed 19 11 
 
 Talc + 15$ sabadilla seed 26 4 
 
 Talc + 2.5$ derris root + 7.5$ 
 
 sabadilla seed 30 
 
 Control test 30 
 
 A ground mixture of 2.5 parts radix derridis ellipticae, 7.5 
 parts semen sabadillae sad 90 parts talcum proved useful in exter- 
 minating grasshoppers (for instance Tachycines asyramorus), 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$ rotenone, 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 cf derris and cube. To prepare the paste, 3 or 4 parts 
 of finely powdered 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 (wilkeite, bentonite, 
 etc.) to make a physically stable emulsion. A preservative such as l/2 to 
 1 percent of carbolic acid may be added; a sodium, potassium, or an 
 ethanolamine soap may be used instead of the clay and an antioxidant such 
 as tannic acid may also be added. 
 
 The paste emulsion insecticide produced as aforesaid, makes a quick 
 breaking emulsion when diluted with water for spraying. Insecticide sprays 
 of this invention possess from 15 to 20 percent greater toxicity to plant 
 lice than sprays of the same high dilution made from derris and cube 
 insecticides of the chemical extracted kind. 
 
 Hamilton (36) , assignor to the Endowment 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 rotenone. Rctenone may be used in the form of a 
 solution in acetone, alcohol, carbon tetrachloride, etc. 
 
- 37 - 
 
 Buc (13), assignor tc the Standard Oil Development Co., in United 
 States patent 2,042,296, issued May 26, 1936, applied for March 12, 1931, 
 claims an insccticidal preparation, comprising a relatively non-volatile 
 petroleum oil, insccticidal material selected fron the group consisting 
 of rotcnonc and rotenoids, and an aryl alkyl ether, the amount of aryl 
 alkyl ether "being sufficient to keep the insccticidal notorial 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 27° A. ?. I. and a viscosity of 115 Saybolt at 
 100° F. Buc prepared a stable kerosene solution containing 0.25 percent 
 of rotenone 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 pyrethrya flowers and derris 
 root with a chemical compound of the alkylolaminc family. For example, 
 derris extract, 1 part, is mixed and heated to about 100° C. with 0.7 
 part by weight of triethanolanine; then 1 part fatty acid (e. g. oleic) 
 is added. A "disinterested" solvent (one that does not undergo chemical 
 reaction) such as dict'aylene 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 August 4, 1936, 
 applied for March 20, 1935, clained diaryl thioxins, especially pheno- 
 thioxin, as an insecticide. Upon mosquito larvae, phenothioxin in aqueous 
 solutions in all concentrations up to 1 part in 500,000 was as effective 
 as rotenone. 
 
 Wotherspoon (105), assignor to Derris, Inc., in United States 
 patent 2,052,374, issued Augast 25, 1936, applied for April 28, 1934, 
 claims an aqueous- dis sen. inatable composition of matter consisting of an 
 insecticide obtainable from derris and similar insccticidr.l-containing 
 plant materials containing rotenone, deguclin, tcphrosin, and toxicarol .. 
 and a water-soluble phenol containing at least two hydroxyl groups. 
 
 "I have found that if rotcnor.o, dihydror'-tenone, finely ground 
 derris or cube, solid extracts of derris or cube, the hylrogenated 
 derivatives of same, either alone or in mixtures , are melted or intimately 
 mixed with a solid water- soluble phenol containing two or more hydroxyl 
 groups, the resulting product after cooling and grinding is soluble, or 
 miscible, with water in any proportions. 
 
 "The products thus produced may be mixed, if desired, with any 
 powdered materials which act as wetting agents, such as soap, alkali 
 salts of sulphonated hydrocarbons or alcohols, sulphonated oils, et cetera, 
 
 "Fillers such as starch, glue, gums, dextrins, flour, clays, talc, 
 bentonite, chalk, diacomaceous earth, ct 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 dihydr.ic 
 phenols such as catechol, resorcinol and quinol and their homologues, 
 and the trihydric phenols such as pyrogollol, phloroglucinol and 
 hydroxy quinol and their homologues." 
 
 Examples are: (1) 12.5 parts "by weight of rotenone are mixed with 
 37.5 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 l/2 parts "by 
 weight of dry hydrogenated derris extract are melted with 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 horticultural 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 , Lonchocar pus , Spatholobu s, etc., are ethyl acetate, 
 ben«ol, 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 G-reat 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 grammes 
 of the root to 400 cc. of common alcohol to which is added l-l/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, deguelin, 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 deguelin, tephrosin, and toxicarol, 
 and nixing 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, barbasco. and timbo roots, such, for example, as Lonchocarpus 
 nicou, Derris e llipti ca, Derris chinensis , D erris malacconsis 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 pyre thrum in at least one member of the group of alkylated 
 
- 39 - 
 
 phenolic ethers consisting of safrol* anethol, methyl eugenol, raid 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, acetone-alcohol mixture, petroleum 
 distillate, chloroform, ethylene dichloride, ether, toluene, xylene, etc. 
 Solvents less effective than safrol, etc. include oil of turpentine, pine 
 oil, terpineol, dipentene, phellandrene, 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 trietha^.ol amine oleate. 
 
 Example 2. 25 parts 5 percent solution of rotenone in camphor oil S. G-. 
 970. 25 parts concentrated solution pyrethrum flowers in camphor oil S. 
 G-., 970. 50 parts triethanol amine oleate. 
 
 Example 3. 25 parts of a solution of the active principles of derris root 
 containing about 10 percent of the derris extractives and 90 percent 
 safrol. 75 parts of aqueous solution of gum acacia 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 pyrethrun flowers in 
 camphor oils S. G-. , 970.- 25 pa,rts of a concentrated aqueous solution of 
 cocoanut oil soap. 50 parts of an aqueous solution of gum ghatti con- 
 taining 5 percent of the latter. This mixture is pa,ssed 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 camphor oil 
 are nixed with 90 parts by volume of petroleum distillate. 
 
 Example 7. 2-l/2 parts of pyrethrun extract (20 to l) and 5 parts of a 
 2 percent solution or rotenone in safrol. are mixed with 92-l/2 parts by 
 volume of petroleum distillate. 
 
 Sankowsky (86), Assignor tc Stanco, Inc., in United States 
 patent 2,058,332, 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, from a plant containing such toxic substances, by treating said 
 plant with a mixed solvent, which is capable 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 distillate, having a, maximum- "boiling point below 625° F. 
 and a sufficient amount of an organic solvent soluble in the petroleum 
 distillate and having solvent power for said toxic substances to dis- 
 solve at least 2-1/2 percent of said toxic substances. 
 
 Derris root, cube root, 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 petroleum distillate preferably used is one having 
 a macimum boiling point below 625° F. The term rotenoids is applied to 
 the insecticidal constituents of Derris , Lonchocm pu s, and Te phrosia 
 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 formate, 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- 
 drogonating the separated extract and dissolving in the hydrogenated 
 extract the active principles of a fish-poisoning plant. For example, 
 kerosene 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 may 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 hydro gen at ed oil extract solution containing 
 5 to 10 percent of rotenone and/or rotenoids and mixing with water, using 
 a suitable emulsifier such as oil soluble sulphonatcd soap, fish oil soap, 
 saponin, etc. Other insecticides may be added to the emulsion, such as 
 lead arsenate, nicotine, pyrethrum, etc. 
 
 Another \ise for the spray solution of the emulsion type is for 
 spraying plants such as trees, shrubs, etc. to control parasites such as 
 aphids, leafhoppers, thrips, greenhouse white flies, tent caterpillars, 
 red spiders, squash bugs, roaches, Mexican bean beetles, Japanese beetles, 
 potato beetles, etc. 
 
 Hotenoids are defined as the non-crystalline extract of fish- 
 poisoning plants consisting of a mixture of deguelin, tephrosin, toxicarol, 
 etc. 
 
 Ailgore (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 jxide oxalate methyl ester. Botanical 
 extractives (e. g. derris extract) V omselves 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 insect icidal 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, [assignor to the California 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 Stanco, 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 of a plant 
 selected from the group consisting of derris and cube root containing an 
 inherent erulsifier 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 T esylic acid (based on the whole 
 mixture) is added as a preservative. This fixture is, after proper agitation, 
 suitable as a stock emulsion which will be ready for use with mere dilution 
 with water. Ground derris 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: 
 
 „*.«#— 
 
- 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 di ethylene glycol 
 monoethyl ether acetate, pyrethrins, and at least one of the active 
 toxic ingridients 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 dichloride, 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 derrie extractives. Large proportions of 
 either solvent may be easily incorporated 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 glycol 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 and cube in a petroleum 
 base insecticide when as little as 1 percent is blended with the petroleum 
 oil. Higher percentages will In Id greater quantities of derris and cube 
 extracts in solution." 
 
 "To be effective as an insecticide, rotenone or other of the derris 
 or cube e^t reacts mentioned should be present in the finished product in 
 concentrations ranging from ,01 to 0.1 per cent by weight." 
 
 Examples of this invention are: 
 
 "In one actual embodiment of the invention I prepared such a solution 
 by first forming a 5 per cent solution of crystallin rotenone in diethylene 
 glycol monoethyl ether acetate and then adding one part, of this solution to 
 100 parts of a petroleum naphtha extract of pyrethrum flowers prepared by 
 extracting 1.2 pounds pyrethrum flowers with a deodorized petroleum naphtha. 
 The resulting product was a stable, non-volatile, substantially odorless 
 solution of excellent insecticidal properties. When tested according to 
 the Pee t -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 mass. I made a 5 percent 
 solution of' this resinous mass in diethylene glycol inonoethyl ether 
 acetate' and prepared an insecticidal solution by adding two parts of this 
 5 per cent solution to 100 parts of a naphtha-pyre thrum extract prepared 
 as before. The resulting insecticidal solution when tested by the Peet- 
 G-rady method gave a knock down of 98 and a kill of 88. 
 
 "My 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 
 concentrated naphtha, solution of pyrethrins with one part of ethylene 
 glycol monoethyl ether acetate containing dissolved therein 5 percent of 
 total extractives prepared by extracting derris with acetone and evapor- 
 ating off the solvent. I then incorporated this blend with 100 parts 
 of petrolatum by 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 tc the ears of cattle 
 to kill car ticks." 
 
 Coo (16), in United States patent 2,090,109, issued August 17, 1937, 
 applied for November 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 a. liquid gelatin is formed by dissolving the gelatin in 
 water. The resulting liquid gelatin is then colored with a water soluble 
 chlorophyll green dye which may be made of thiocarmine blue and tartrazine 
 yellow. Powdered rotenone is then added to the chlorophyll green liquid 
 gelatin. The amount of rotenone to be used is governed 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 an orange yellow dye, or the colors 
 above 4900 Angstrom units of thr< visible spectrum, although chlorophyll 
 green and orange yellow are preferable. A black pigment or opaque substance 
 may be used in forming 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), assignor 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 paraff inic 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 
 ^23^22^6' ^2^202^2* ^ e a lso 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 , Lor cho carpus , 
 Tephrosia ) containing rotenone in dichloroacetic acid, adding water and 
 separating the resulting crystalline product. Referer.ee is made to the 
 addition compounds of rotenone with acetic acid, propionic acid and alpha- 
 chloropropionic acid in each of which the molecular ratio is two mols of 
 rotenone to one mol of acid. 
 
 O'Xane (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 ma.y 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. ADAMS, E. 1. 
 
 1934. Mothproofing composition. Canadian Patent 338,896; issued 
 January 23, 1934; applied for October 23, 1931. 
 
 2. BADEKCSCHER, 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. BAG1UIL-3ULL, S. 
 
 1924. Improvements 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. BOEHRIHGER, C. H. 
 
 1934. Japanese firm claims new process of obtaining toxic substances 
 
 from derris. U. S. Dept. Com., Bur. Foreign and Dom. Com., 
 Economic and Trade I\ T otes no. 310. Rcpt. from the Asst. 
 Trade Commissioner, Singapore, S. S. , dated March 8, 1934. 
 
 7. BOOTH STEAMSHIP CO. LTD., and WAHD, 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. 
 
 9. 
 
 1936. Perf ectionnements a 1' extraction des toxines, pour la fabrica- 
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 February 11, 1936; applied for August 27, 1935; in England 
 March 30, 1935. 
 
 1937. Verfahren zur Kerstellung von fur die Insektenvertilgung 
 verwendbaren Auszugen aus Rotenon enthaltenden Wurzeln. 
 German Patent 646,570; issued June 17, 1937; applied for 
 September 11, 1935. 
 
 10. BOUSQJJET, E. W. 
 
 1935. Contact insecticide. U. S. Patent 2,006,227; issued June 25, 
 1935; applied for October 19, 1932. 
 
 11. and TISDALE, 1. H. 
 
 1934. Contact insecticide. U. S. Patent 1,954,517; issued April 
 
 10, 1934; applied for July 8, 1932. 
 
 12. BUC, H. E. 
 
 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. CKEMISCHE FABRIK MARIENPELDE G.m.b.H. 
 
 1935. Improved manufacture of derris root extracts and other 
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 July 30, 1935; applied for January 11, 1935; in 
 Germany, January 18, 1934. 
 
 15. CHROMEK, P. 
 
 1937. Aus rotenon oder tubatoxin enthaltenden pflanzenwurzeln 
 
 hergestelltes insektenbekampfungsmittel. 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 
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 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, I. J. 
 
 1934. Vermin destroyer. U. S. Patent 1,963,838; issued June 19, 
 1934; applied for May 23, 1933. 
 
- 47 - 
 
 22. DOW, H. H., and 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. DUPRE ET CIE 
 
 1934. Produit insecticide. French Patent 769,445; issued 
 August 25, 1934; applied for February 28, 1934. 
 
 24. EICHKORN, K. 
 
 1936. Verfahren zur Herstellung eines derrisextrakthaltigen 
 
 insektenbekampfungsmittels. German Fatent 630,483; 
 issued May 28, 1936; applied for November 22, 1932. 
 
 25. EAWCETT, 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 CHEMICAL INDUSTRIES, LTD. 
 
 1936. Process of producing rotenone and associated substances 
 from natural sources containing the same. British 
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 27. FRYER, P. J. 
 
 1926. Insecticide, sheep dip, and the like. U. S. Patent 
 
 1,583,681; issued May 4, 1936; applied for November 
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 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. GRANT, D. H, . ■ ■ ... 
 
 1929. Insecticide. Canadian Patent 333,643; issued June 27, 
 1933; applied for October 25,- 1929. 
 
 32. 
 
 1933. Insecticide. U. S. Patent 1,934,057; issued November 7, 
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 33. 
 
 1933. Insecticide and process of making the same. U. S. Patent 
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 34. KALLER, H. L. J. and SCHAFEER, P. S. .'•" . 
 
 1934. Process of preparing dihydrorotenone. ; : U. S. Patent 
 
 . 1,945,312; issued January 30, 1934- "applied 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. 
 
 36. '.. . 
 
 1936. Insecticide composition. U. S. Patent 2,035,546; issued 
 
 March 31, 1936; applied for May 14, 1932. .'•" 
 
 37. HOFFMANN, P. -LA ROCHE AND GO. . 
 
 1926. Schadlingsbekampfungsmittel. 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. 
 
 i t ■ i 
 
 39. I. G. EARBENINDUSTPJE A. G-. 
 
 1932. Improved prcparatibns for killing flies. British Patent 
 377,069; issued July 21, 1932; applied for November 27, 
 1931; in Germany, November 27, 1930. 
 
 40. 
 
 1932. Pliegenvertilgungsmittel. German Patent 555,117; issued 
 July 18, 1932; applied for November 28, 1930 
 
 
- 49 - 
 
 41. I. G. FARBENINDUSTRIE A. G. 
 
 1932. Improved process for killing or eliminating flies and 
 
 preparations therefor. British Patent 378,300; issued 
 August 11, 1932; applied for December 12, 1931; in 
 Germany , December 13, 1930. 
 
 42. IIBA, T., and NAKATUKA, S. 
 
 1931. Insecticide. Japanese Patent 91,478; issued May 20, 1931; 
 [Abstract in Chem. Abs. 26;1703. 1932. J 
 
 43. IMAI, Y. 
 
 1931. Insecticide. Japanese Patent 91,645; issued June 3, 1931; 
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 44. IMPERIAL CHEMICAL INDUSTRIES, LTD. 
 
 1936. Procede de fabrication de la rotenone et des substances 
 associees en partant des produits naturels qui en 
 contiennent. French Fatent 797,052; issued April 20, 
 1936; applied for October 29, 1935; in England, 
 October 29, 1934. 
 
 45. IMPERIAL CHEMICAL INDUSTRIES OF AUSTRALIA AND NEW ZEALAND LTD. 
 
 1936. Improvements in or relating to the protection of sheep 
 
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 46. IMPERIAL CHEMICAL INDUSTRIES, LTD. 
 
 1937. Rotenone production. Canad. patent 369,499; issued 
 
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 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.] , 
 
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50, 
 
 52. 
 
 56, 
 
 IS 33. 
 
 51. 
 
 1934. 
 
 - 50 - 
 
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- 51 - 
 
 59. — and HOWIES, F. 
 
 1924. Improvements in the manufacture of insecticides, sheep 
 
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- p 2 - 
 68.. McDOUGALL and YALDING (LTD.) • - 
 
 1925. Perfectionnements aux insecticides, aux "bains pour moutons 
 et aux substances similaires. French Patent 589,506; 
 issued May 30, 1925; applied for November 22, 1924. 
 
 69. —*^aod YALDING (LTD.), and FRYER, P. J. 
 
 1925. Improvements in insecticides, sheep dips, and the like. 
 
 ' 3ritish 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 33b;<9\' ? issued 
 January 23, 1934; applied for April 1, 1932; assigned to 
 " Standard Oil Co. 
 
 74. MIKESKA, L. A. 
 
 1936. Insecticide and insect repellent and matb.od of .caking the 
 same. U. S. Patent 2,066,184; issued December 29, 1936; 
 " . ;; _ 'applied for October 29, 1932. 
 
 75. MILLS, L. E. and FAYERWEATHER, B. L. 
 
 1934. Tertiary alkyl substituted orthodihydroxybenzenes. U. S. 
 Patent 1,942,827; issued January 9, 1934; applied for 
 March 27, 1933. 
 
 76. NETTAI SANGYO KABUS-HIKI KAISRA 
 
 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. 
 
- 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. 0H0RI, T., and NAZAZAWA, Z. 
 
 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 Pdkagaku Zenkujo, Tokyo, Japan. 
 
 79. O'ZANE, 77. 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, Z. and DUNZEL, M. 
 
 1934. Insecticidal agent. Canadian Patent 345,383; issued October 
 16, 1934; applied for D e cember 12, 1931; in Germany, 
 December 13, 1930. 
 
 82. PJEDEL-E. DE EAEN, J; D. , A.-G. 
 
 1933. Procede d'aneantissement 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 MOHAN, J. A. 
 
 1936. Preparation of insecticides. U. S. Patent 2,043,267; issued 
 June 9, 1936; applied for October 2, 1933. 
 
 84. SANDEHS, 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. SAMOTCSKY, 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 GOHNITZ, K. 
 
 1935. Insecticide. Canadian Patent 348,380; issued February 26, 
 1935; applied for January 24, 1934. 
 
 90. and GORNITZ, E. 
 
 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. SLMANTON, 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. 
 
* 66 - 
 
 9 5. STANDARD OIL DEVELOPMENT COMPANY 
 
 1931. Improved insecticidal, insect-repelling and fungicidal 
 
 compositions. British Patent 550,397; issued June 15, 
 1931; applied for February 15, 1930. 
 
 96. SANKOWSKY, N. A., and PULTON, 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., PPAPP, K., KRAMER, R. , and KEEN, 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. VOORHEES, V. 
 
 1935. Light stable insecticide. U. S. Patent 2,011,428; issued 
 August 13, 1935; applied for Mgy 4 } 1931; assigned to 
 Standard Oil Co., of Indiana, Chicago, 111. 
 
 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. WIICSTROM, E. G. A. 
 
 1935. Insecticide and method of producint the same. 3ritish 
 Patent 434,660; issued September .6, 1935; applied for 
 March 19, 1934. 
 
- 5b - 
 
 103, 
 
 1S36. Insektdodande medel.' Swedish Patent 86,063; issued April 
 15, 1936; applied for March 16, 1934. 
 
 104 
 
 1936. Insektdodande medel. Swedish Patent 87,525; issued October 
 13, 1936; applied for March 16, 1934. 
 
 105. WOTHERSPOON, R. 
 
 1935. Process for producing water-soluble end water miscible 
 
 insecticides and products produced thereby. U. 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 HO JIN EIKAGAKU IvENKYUJO 
 
 1926. 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. 
 
 108 
 
 1928. A 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. Insecticides. British Patent 300,606; applied for July 
 17, 1928; in Japan November 16, 1927; not yet accepted. 
 Illus. Of fie. Jour. No. 2086, 6904 (1929). (Reproduced 
 by permission of the Controller of His 3ritannic 
 Majesty's Stationery Officer). 
 
 110. 
 
 1929. Powdered insecticide containing active ingrediants of 
 
 roots of- derris species. Australian Patent 15,327/28; 
 issued July 24, 1929; applied for August 28, 1928; in 
 Japan, November 16, 1927. 
 
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. 
 
 Fryer, P. J.; see McDougall and Yalding (Ltd.) 
 
 Fulton, S. C. ; see Sankowsky, N. A. 
 
 Fulton, S. C. ; see Standard Oil Development Company 
 
 Go'rnitz, K. ; see Schotte, H. 
 
 Kale, W. J.; see Dow, H. H. 
 
 Howies, 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 Ryan, V. H. 
 
 Nakatuka, S. ; see Iiba, T. 
 
 Nakazawa, K. ; see Ohori, T. 
 
 Nellensteyn, F. J. ; see G-raafland, 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, E. W. 
 
 Ward, H. G. ; see Booth Steamship Co. , Ltd. 
 
 Assignee Index 
 
 C. 3. 3yrnes, Trustee; see James, J.'H. 
 
 California Spray-Chemical Corp. ; see Sessions, A. C. 
 
 Derris, Inc. ; see Wotherspoon, R. 
 
 Deutsche Gesellschaft fur Schadlingshekampfung 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 Nemours & Co., see Bousquet E. W. and Tisdale, W. H. 
 Endowment Foundation of New 3runswick, 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 Eydrogenation Patents Co. , see Pfaff & Dunkel. 
 Kessler Chemical Corp.; see Goldschmidt, S. and Martin, K. 
 McCormick & Co. , Inc. ; see Badertscher, A. E. 
 McDougall & Yalding, Ltd. ; see Fryer, P. J. 
 
 Schering-KahToaum, A. G. of Berlin, Germany; see Schotte, H. and Gbrnitz, K, 
 Stanco, Inc. 
 Stanco, Inc. 
 Stanco, Inc. 
 
 see Donlan,' T. R. 
 
 see Hunn, E. B. 
 
 see Sankowsky,' N. A. 
 
 Standard Oil Company of Indiana; see Voorhees, V. 
 
- 58 - 
 
 Standard Oil Development Company; see Adams, 3. W. , Buc, H. E. , Grant, D. H. 
 
 McG-ill, W. J., Mileska, L. A., Sankowsky, N, A. and Fulton, S. C. 
 Yates, W. J.; see Shell Development Co., Ltd. • ..•• .- 
 Zaiden Hojin Rikagaka Eenkujo ; see Ohori, T. and llakazawa, ' E. 
 
 Diluents 
 
 Agar- agar, U. S. 1,926,968 
 
 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 
 
 lir.oleate, Brit. 280,256; Ger. 643,804 
 
 oleate, Brit. 280,256 
 sec-Amyl alcohol, U. S. 1,940,646 
 Amyl salicylate, Ger. 555,117 
 Anthraquinone, 1,4-toluido, l T . 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. 369,390 
 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; tJ. S. 1,724,626 
 Bentonite, Austral. 20,894/35; U. S. 1,928,968, 1,940,899, 2,030,584, 
 
 2,052,374 
 Benzene, dichloro, TJ. S. 1,940,646 
 Benzoic acid esters, Canad. 345,383 
 Benzoic acid ethers, Canad. 345,383 
 Benzyl alcohol, TJ. S. 1,514,377 
 
 Bordeaux mixture, Brit. 246,252; U. S. 1,583,581, 1,803,870 
 sec-Butyl alcohol, U. S. 1,940,646 
 Calcium arsenate, TJ. 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. 245,252; TJ. S. 1,583,681, 1,803,870 
 Castor oil - Brit. 239,483; TJ. S. 1,724,626 
 
 sulphonated, Brit. 229,773; Canad. 253,319; French 589,506; U. S. 
 
 1,583,681 . . 
 
 Catechol, TJ. S. 2,052,374 
 Cement, hydraulic Brit. 362,526 
 Chalk, U. S. 2,052,374 
 Chloresterinozonide, Swiss 124,290 
 
 Chrysanthemum ( Pyre thrum) , U. S. 1,940,899, 2,056,184 
 Chrysanthemum extract, Brit. 434,660; Canad. ' 369,390 
 Clay, colloidal, TJ. 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. 3. 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, diphenyl, Brit. 377,069; Ger. 555,117 
 
 Eats, Brit. 239,483, 285,797; Dutch 21,841; "J. S. 1,724,626 
 
 Fatty acids higher, Brit. 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, IT. 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 
 Hydrocarbons - 
 
 higher, Brit. 235,797, 239,483; Dutch 21,641; 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. 239,483 
 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; T J. 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 
 ; Mineral oil, sulphonated, IT. S. 1,940,646 
 Molten carrier, Canad. 348,380 
 Naphthalene, Jap. 91,645 
 Naphthalene, 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, hydrogena.ted, Brit. 239,482 
 Oil, fatty sulphonated, French 539,506; Canad. 253,319 
 
 Oils - Brit. 239,483, 235,797; Dutch 21,841; U. S. 1,724,626, 2,030,584 
 chrysalis, Brit. 239,483; Dutch 21,841; J. S. 1,724,626 
 
 ethereal, chlorinated, Brit. 434,660; Swedish 66,083 
 
 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. 239,463; 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 21,641; U. S. 1,724,626 
 
 sulphonated, U.- S.- 2,052-, 374, 1,940,646, 1,583,681 
 
 vegetahle, Dutch 21,841; French 769,445; T J. S. 1,724,626; 2,030,584 
 
 vegetable hard, U. S. 1,724,626 
 
 vegetahle 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 21,641; U. S. 1,724,626 
 
 Paraffin wax, sulphonated, Canad. 253,319; French 589,506; U. S. 1,583,681 
 
 Peanut oil, French 769,445 
 
 Potrolatuni, U. S. 2,089,765 
 
 Fetroleum - 
 
 fractions, sulphonated, U. S. 2,006,456 
 
 sulfonates, U. S. 1,934,057 
 
 sulphuric sopp 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 21,641; U. S. 1,724,626 
 Potassium oleate, U. S. 1,926,968 
 Protein, animal, Dutch 21,841 
 
 Pyrethrins, U. S. 1,967,024, 2,058,200, 2,089,766 
 Pyre thrum, U. S. 1,940,899, 2,066,184 
 Fyrethrum, 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. 265,797; 239,483; Dutch 21,841; U. S. 1,724,626 
 Resorcinol, U. S. 2,052,374 
 
 Roiin soap, Brit. 350,897; U. S. 1,934,057, 1,940,646 
 Sabadilla seeds, Canad. 348,379; U. S. 2,024,392 
 
 Saponin, Brit. 350,697; 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, 2(y 
 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 infg. 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 
 
 Sulphonated 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 
 
 Tannic acid, U. S. 1,928,968, 2,030,534 
 
 Terpineol, U. S. 1,940,646 
 
 Triethanolamine, Brit. 154,660 
 
 Triethanolamine, oleate, French 769,445; U. S. 1,928,968, 2,043,267, 2,058,206 
 
 Turkey red oil, U. S. 1,940,646 
 
 'Turpentine, Japanese, 91,645 
 
 Urethanes - Ger. 564,018 
 
 substituted, Ger. 564,018 
 Veratrin, Can. 343,379; U. S. 2,024,392 
 Water softening agent, U. S. 1,065,156, Brit. 3204-/1911 
 Waxes, Brit. 239,483, 285,797; Butch 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 
 Wyrol, U. S. 1,934,057 
 
 Extractants and Solvents 
 
 Acetic acid, U. S. 1,923,968, 2,103,195 
 
 dichloro, U. S. 2,103,195 
 Acetone, U. S. 1,928,968, 1,934,057, 1,945,312, 2,030,534, 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. 1,533,681; 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. L,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. 85,083 
 
 Decalin, U. S. 1,934,057 
 
 Diacetone alcohol, U. S. 1,928,963 
 
 Dipentene, U. S. 2,058,200 
 
 Esters, Brit. 350,397; U. S. 1,934,05? 
 
 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, monocthyl, U. S. 2,039,766, 2,043,257 
 Ether, sec-hcxylcresyi ether, U. S. 2,042,295 
 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 alcohol, Dutch 21,841; U. S. 1,724,626, 1,928,968, 1,940,646 
 Ethyl alcohol, absolute, Brit. 239,483 
 Ethyl formate, U. S. 1,928,968 
 
 Ethylene chlorohydrin, U. S. 1,514,377, 1,928,968 
 Ethylene dichloride, U. S. 2,o3o,534, 2,052,374, 2,058,200 
 Ethylene, dichloro, Brit. 423,625, 432,626 
 Ethylene, trichloro, Brit. ^32,626 
 Gasoline, chlorinated, U. S. 2,013,023 
 
 Glycol, diethylene, monocthyl 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, Ger. 643,804 
 Hydrocarbon, aromatic, Brit. 350,397; U. S. 1,583,057 
 Hydrocarbon oil, Brit. 280,256 
 Hydrocarbon white oil, U. S. 1,786,125 
 Hydrocarbon white oil, chlorinated, Canad. 338,896; U. S. 1,934,057 
 
- 64 - 
 
 Hydrocarbons - -...'. 
 
 chlorinated, Canad. 358,696;- U. ' S. 1,934,057 
 
 Paraffinic, U. S. 2,096,885 . . 
 
 Unsaturated, Brit. 394,977; Canad. 340,315 
 
 Hydro genated 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. 1,940,645, 1,957,024, 2,013,028, 2,042,296 
 
 Kerosene plus chloroform, U. S. 1,967,024 
 
 Kerosene plus oil soluble sulfonate, U. S. 1,940, 6^6 
 
 Kerosene plus oil soluble sulfonate plus ethyl methyl ketone, U. S. 1,940,546 
 
 Kerosene plus sec-butyl alcohol, U. S. 1,940,646 
 
 Ketone, diethyl, 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. 376,300 
 
 Limonene, U. S. 2,058,200 
 
 Linseed stand oil, Brit. 446,576 
 
 Lubricants, oils, Brit. 280,255 ... 
 
 Lutidinc, (dimethyl 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; IT. S. 1,724,626 
 
 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 potash, rosin soap plus 
 
 ethyl methyl ketone, plus hexahydrophenol, plus crespl,. U. S. 1,940,646 
 Naphtha, U. S. 1,940,646 
 
 Naphthalenes, chlorinated, Brit. 350,897; U.' S. 1,934,057 
 Naphthalenes, hydrogenated, Brit. 350,897; U. S. 1,934,057 
 Qlls - 
 
 pine, U. S. 2,058,200 .."... 
 
 pine, steam distilled, Brit. 350,897; U. S. 1,954,057 
 Olive oil, Brit. 446,576 ' . , - 
 
 Petroleum - Ger . 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 
 
 chlorobcnzcne, U. S. 2,058,832 
 
 chloroform, U. S. 2,058,832 . ■ . 
 
 dichlo.ro ethyl ether, U. S. 2,053,832' 
 
- 65 - 
 
 ethylene dichloride, U. S. 2,058,832 
 
 ethylene chlorohydrin, U. S. 2,058,832 
 
 n-propyl formate, U. S. 2,058,832 
 
 toluene, U. S. 2,058,832 
 
 trichloroethylene, U. S. 3,058,832 
 
 xylene, U. S. 2,058,832 
 Petroleum ether, Brit. 239,483; Dutch 21,841; U. S. 1,724,626 
 Petroleum naphtha, Canal. 338,896, 358,897; U. S. 1,854,948 
 Petroleum naphtha plus - 
 
 acetone, U. S. 2,089,766 
 
 benzol, U. 5. 2,089,766 
 
 camphor sassafras oil, U. S. 2,089,766 
 
 carbon tetrachloride, U. S, 2,089,766 
 
 chloroform., U. S. 2,089,766 
 
 di ethylene glycol mono ethyl ether acetate, U. S. 2,089,766 
 
 ethylene dichloride, U. S. 2,089,766 
 
 ethylene glycol monoethyl ether acetate, U. S. 2,089,766 
 Petroleum oil - 
 
 hydrogenatod, U. S. 2,066,184 
 
 non- volatile, U. S. 2,042,296 
 
 non- volatile viscous, U. S. 2,013,028 
 
 white, Brit. 350,897 
 Petroleum white oil, Brit. ,350,837; U. S. 1,334,057 
 Petroleum white oil plus chloro naphthalene plus K- rosin soap, plus oil soluble 
 
 sulphonatc, plus scc-amyl alcohol, plus steam distilled pine oil, 
 
 U. S. 1,940,646 
 Petrol cum white oil r>lus oil soluble sulpr.onatc plus crude dichlorobcnzcne, 
 
 U. S. 1,340,645 
 Phellandrene, U. S. 2,058,200 
 Phenol, Brit. 350,897; T J. S. 1,934,057 
 Phenol ether, alkylated, U. S. 2,058,200 ' 
 Phenols, Brit. 280,256 
 Phenyl ethyl ketone, U. S. 1,928,968 
 m-phenyl tolyl ketone, U. S. 1,928,968 
 o-phenyl tolyl ketone, U. S. 1,926,968 
 alpha-picoline, U. S. 1,928,256 
 beta-pi coline, U. S. 1,928,256 
 g amm a-pic ol ine , U. S. 1,928,256 
 Propionic acid, U. S. 2,103,195 
 Propionic acid, alpha chloro, U. S. 2,103,195 
 Propylene chlorohydrin, U. S. 1,514,377 
 Pyridine, U. S. 1,928,256, 1,328,968 
 Pyridine, alkyl, U. S. 1,928,256 
 Pyridine allyl, U. S. 1,928,236 
 Pyridine, ethyl, U. S. 1,926,256 
 Pyridine base, U. S. 1,328,256 
 Pyridine, dimethyl, U. 3. 1,928,256 
 Pyridine, trimethyl, U. S. 1,928,255 
 Safrol, U. S. 2,052,374, 2,058,200 
 Shale oil, hydrogenated, Brit. 378,300 
 Sodium bisulphite solution, G-er. 630,483 
 
- 66 - 
 
 Terpineol, Brit. 350,897; U. S. 1,934,057, 2,058,200 
 
 T'erpinolene , U. S. 2,058,200 ' '■ 
 
 Tetralin, U. S. 1,934,057 
 
 Toluene, U. S. 2,058,200 
 
 Turpentine, oil, U. S. 2,058,200 , • ■ 
 
 Vegetable oil, U. S. 2,104,757 
 
 white oil, Brit. 350,39'7; "Uanad. 3.73,642; U. S.- 2,011,426 
 Xylene, U. S. 2,053,200 
 
 Reagents Used in Preparing Derris Extract 
 
 Aluminum salt for coagulating derris latex ■ 
 Aluminum sulphate for coagulating derris latex 
 Iron salt for coagulating derris latex 
 Lead salt for coagulating derris latex- 
 Lime, milk of, for coagulating derris latex 
 Sulphuric acid in alcohol for extracting derris 
 Salt in [preparing derris extract • • 
 
 Sodium carbonate in preparing derris extract ■ 
 Sodium hydroxide in preparing derris -extract 
 Tartaric acid in preparing derris extract 
 
 Brit. 226,250 
 
 Brit. 226,250 
 
 Brit. 226,250 
 
 Brit. 226,250 
 
 Brit. 214,822 
 
 Brit. 437,171 
 
 Brit. 214,822 
 
 Brit. 214,822, 437,171 
 
 Brit. 226,250 
 
 Brit. 214,822 
 
 Staoilizers 
 
 Anthracene, Brit. 350,897 
 
 An th raqui n ones 
 An thraqui none s 
 An. thraqui nones 
 Anthraquinone s 
 An thraqui no nc s 
 Anthraquinoncs 
 An thraqui nones 
 Anthraquinone r 
 An thraqui nones 
 Anthraquinone s 
 An thraqui n ones 
 Anthraquinone s 
 An thraqui none s 
 
 alkyl , 
 amino, 
 amino , 
 amino , 
 amino , 
 amino , 
 
 n 
 
 S. 2,011,428 
 U. S. 2,011,428 
 alkylphenyl, U. S. 2,011,428. 
 diaryl, U. S. 2, OIL, 428 
 oxyphonyl, U. S. 2,011,428 
 phenylated, U. S. 2,011,428 
 aralkyl, U. S. 2,011,423 
 aryl, U. S. 2,011,423 
 arjrl diamino, U. S. 2,011,428 
 
 a?, arm no, 
 
 ,011,428 
 
 S. 1,942,827 
 
 hydroxy, U. S. 2,011,428 
 nitro, U. S. 2,011,428 
 4,4-toluido, li. S. 2,011,428 
 
 Benzene, 1 ,2-dihydroxy-4-tert. alkyl, U. S. 1,942,827 
 
 Benzene, i,2-dihydroxy-4-tert. amyl , U. S. 1,942,827 
 
 Benzene, 1 ,2-dihydroxy-4-tert "butyl, I". 
 
 Black 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- ITaphthol , Brit. 350,397 
 
 tfitrocresol, Brit. 350,897 
 
 Orange yellow dye, U. S. 2,090,109 
 
Phenanthrene, Brit. 350,897 
 Phenylhydrazine, Brit. 350,397 
 Toluidine, Brit. 350,397 
 
 A List of All Patents Arranged According to Piling Dates 
 
 Filing Date 
 
 February 8, 1911 
 Auril 37. 1913. 
 
 September 8, 1911 
 April 6, 1913 
 December 4, 1916 
 December 21 , 1916 
 December 22, 1916 
 March 31, 1920 
 April 16, 1923 
 April 16, 1933 
 June 23, 1923 
 December 1, 1923 
 April 15, 1924 
 May 14, 1924 
 Hay 22, 1924 
 June 16, 1924 
 July 22, 1924 
 November 12, 1924 
 November 22, 1924 
 November 26, 1924 
 No vemb e r 2 9 , 1 924 
 April 24, 1925 
 June 25, 1925 
 August 31, 1925 
 February 10, 1926 
 October 5, 1926 
 November 24, 1926 
 i.Iay 18, 1927 
 October 3, 1927 
 October 19, 1927 
 November 7, 1927 
 February 10, 1926 
 February 20, 1928 
 July 17, 1928 
 August 28, 1928 
 October 31, 1926 
 February 25, 1929 
 March 9, 1929 
 March 12, 1929 
 June 6, 1929 
 October 25, 1929 
 February 15, 1930 
 
 Patent 
 
 Brit. "3,204/1911 
 Brit. 10,215/1911 
 
 r 
 
 IT. ST 1,065,156 
 Brit. 8,322/1912 
 Brit. 105,525 
 C-er. 321,317 
 C-er. 327,583 
 17. S. 1,514,377 
 Brit. 214,822 
 IT. S. 1,621,240 
 Brit. 226,250 
 .Trit. 229,773 
 Brit. 233,857 
 French 589,969 
 Canad. 247,627 
 Austral. 18,227/24 
 U. S. 1,522,041 
 Brit. 246,252 
 French 589,506 
 Canad. 253,319 
 U. S. 1,583,681 
 Brit. 239,483 
 Brit. 247,140 
 IT. S. 1,724,626 
 Dutch 21,841 
 Swiss, 124,290 
 Brit. 280,256 
 U. S. 1,786,125 
 U. S. 1,803,370 
 0. S. 1,940,646 
 U. S. 1,854,948 
 IT. S. 1,745,907 
 Brit. 285,797 
 Brit. 300,606 
 Austral. 15,327/28 
 U. S. 1,934,057 
 Reissue 18,667 (IT. S.) 
 U. S. 1,820,394 
 Canad. 293,233 
 U. S, 1,967,024 
 Canad. 333,542 
 Brit. 350,897 
 
- 68 - 
 
 Filing date- 
 
 Patent 
 
 Harch 11, 1230 
 March 12, 1930 
 August 23, 1930 
 August 23, 1930 
 September 10, 1930 
 November 28, 1930 
 March 12, 1931 
 March 12, 1931 
 May 4, 1931 
 July 5, 1931 
 August 20, 1931 
 October 23, 1931 
 November 2? , 1931 
 December 12, 1931 
 December 12, 1931 
 December 24, 1931 
 January 4, 1932 
 January 21, 1932 
 February 7, 1932 
 April 1, 1932 
 May 14, 1932 
 July 6, 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 25, 1935 
 October 2, 1933 
 October 2.1, 1933 
 November 15, 1933 
 December 12, 1933 
 January 24, 1934 
 January 24, 1934 
 February 20, 1932 
 March 16, 1934 
 March 16, 1934 
 March 19, 1934 
 April 4, 1934 
 April 28, 1934 
 May 31, 1954 
 June 5, 1934 
 September 24, 1934 
 October 20, 1934 
 
 U. S. 1,847,540 
 U. S. 2,006,456 
 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. 338,896 
 Brit. 377,069 
 Brit. 378,300 
 Canad. 345 , 383 
 Canad. 340,315 
 Brit. 394,977 
 IT. 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. 2,066,184 
 Ger. 630,483 
 U. S. 1,942,104 
 U. S. 2,058,832 
 U. S. 1,942,827 
 "J. S. 1,945,312 
 U. S. 1,963,338 
 U. S. 2,043,267 
 U. S. 2,096,885 
 U. S. 2,090,109 
 U. S. 2,024,392 
 Canad. 343,379 
 Canad. 348,380 
 French 769,445 
 Swedish 85,083 
 Swed. 87,625 
 3rit. 434,660 
 U. S. 2,033,098 
 U. S. 2,052,374 
 U. S. 2,104,757 
 U. S. 2,030,584 
 French 778,844 
 Brit. 446,576 
 
- 69 - 
 
 Filing Date 
 
 Patent 
 
 December 17, 1934 
 January 11, 1935 
 January 11, 1935 
 llarch 20, 1935 
 Llarch 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 
 March 7, 1936 
 December 24, 1936 
 July 3, 1937 
 
 Canad. 357,959 
 Austral. 20,994/35 
 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