LIBRARY STATE JPLANT fiOAf?D E- 514 October 1940 ABSTRACTS Or IHCEHT POiffllGII AIH) DOfflSTIC PATSITTS PEIu.TIlTG TO DEZRIS, LOITCEOGAZPUS, TSPHROSIA, Aim EOTEiTOlTE (First supplement to E-446) By R. C. PLoark In Au^st, 1933, the Bureau of Entcnolog;' and Plant ("quarantine issued miiaeographed pulDlication E-445 entitled "Abstrac'-.s of foreign and Domestic Patents Relating to Dorris, Lonchocarrms, Rotenone." ^ephrosia, and Since that time ;r.an;' additiorial patents in this field Iio,ve "been granted inventors in the United States and abroad, and in order to heep chemists and entomologists info:nned of the rapid derelop'ients in rotenone products it seems desii'a-ble to issue a supplement to S-446. In this supplement, the first of a series to be issv.ed from time to time, there is included mention of patents v;hich refer incidentall7 to rotenone^ derris, an& cube, and also of patents ^'hich describe adliosives, wetting agents, stabilizers, or other adjuvants intended especially for use :;ith rotenone prodiicts. Readers of this publication vill be interested in the legal status of United States reissue patent 18,G37 (issued to IJ. J. Dennis on On ilovenber 5, 1939, the decision of ;o revie'-r November 22, 1932), vrhich v;as 'abstracted in the Supreme Court of the United States refused the United States Circuit Coijj-t of Appeals for the Seventh Circuit in Chicago, v;hich had declared this patent to be invalid for lack of origin- alit7 on the ipart of the patentee and for lack of invention over the art. I-Ioreover, the Peruvian Ilinistr^ of Pomento (36) on rebruar^ 1, 1938, declared Dennis' Peravieui patent ITo. 98G (vrhich v;as granted him on September 15, 1932) null and void because in 1910, namel7, 20 ^ears prior to the granting of the patent, the G-overnment of Pera vras already carr^'-ing on studies vrith regard to the imioortance of cube or barbasco as insecticide or vermifuge, and also the use of this product in pov/der form and in the form of extract has been an industry- freelj carried on in the Republic since remote da,tes, vmich cler«,rl7 established facts show the absolute lack of originality of the TDatent in ouestion. - 2 - British patents: C-oldschjnidt and Ilartin (18), in British patent 471,153, issv.ed August 25, 1937, apx-)lied for re'oruriry 26, 1938, claini an insecticide coijrprisin^S an aromatic isothioc^anate aduixed vdth a pulverulent diluent or vrith an insecticide of a different cliaracter or v/ith 'ooth. Mixtures of arosiatic isothiocj'anates \i±th insecticides of a different cliaracter, such as, for exa-ple, nicotine, derrin extract, or rotenone, liave in- secticidal pro-perties greatly exceeding a mere aggregation; the^ form effective liquid insecticides, according to the invention, '-'hen dissolved in a solvent or formed into an enulsion, s.nd in this form are ii.seful for spra^/lnf:,. Che proportion of aromatic isothiocj-'anate na^ "be very small (cf. Canadian patent 357,959, issued May 19, 1936). Che Lu:ievale Procfucts Ltd. and PitzC-ihoon (29), in British patent 492,660, issued Septemoer 20, 1936, applied for Ilarch 20, 1937, claim the manufacture of nev; relatively './p.ter-inscluhle stable complex compounds hy hringing together in aqueous solution nicotine or a nicotine salt, a soluble stable copper salt, and a third compoimd capable of reacting ^rith the copper salt, the normal cirpected product of such reaction being modified by the inclusion of nicotine in a resultant complex bod;:'. Che products may be employed as such or they may be made into in- sec ticidal and fiuagicidal preparations by mixir^^, blending or coprecip- itatiiig them vn.th or upon or otherwise corapo-onding them vath solid diluents, fillers, or other insecticides and/or fungicides, e.g., lead arsenate, bordecux mixture, cui^rous oxide, derris preparations, etc., or thoy may instead be mixed •-.■rlth a liquid diluent or dispersing agent v/hich itself may liave insecticic?i2,l and/or fungicidal properties. Che I. G-. Tarbenindustrie A.-G. (24), in British patent 493,764, issued October 10, 1938, applied for April 9, 1937, in C-ermaJiy April 11, 1936, claims an insecticide comprising in aduuxture a diazoamino com- poiijid free from sulphonic acid groups and carbo:c:^l groups, and a solid inert substance and/or a vetting agent and/or an adiiering agent. Mir-.tures v/ith hno-.m contact poisons, for instance derris, may be prepared. Che ITaamloa::e '.''snnootscha-o Chemische Pabriel: Servo and r.ozenbroeJc (32), in British patent 501,801," issued rebruaiy 27, 1939, applied for August 25, 1937, in Holland -Vagtist 25, 1935, clai;.i a preparation for co:.;batiiig plant diseases, comprising a sulp:ioii?,tod ester derived from. an acid of boron or phosphorus and a hydroxy compound of high molecixlar v/eight together uith an insecticide of the class nicotine, rotenone, derris, and like vegetable insecticides. Cor e::ample, castor oil fatt^' acid, about 30 percent of vrhich is converted into the butjrl-ether, is esterified "ith glycol in such a vray tliat one hydroxj'- group of tl^e glycol remains unesterified. Che free hydrox;"- group is esterified vith phosphoric acid and s'absequently sulphonated, and the reaction product is made into a solution corresponding to 30 percent of castor oil fatty acid. 7x--is product improves the spreading povrer of derris or rotenone. - 3 - Ripper (37), in British patent 505,853, issued liay 18, 1939, applied for lTovem"ber 18, 1937, in Austria Hovembor 20, 1935, and April 20, 1977, claims a poison for destroying insects and other invertebrates corn- prising T)articles of a toxic substance which is injurious to plants vfhen a.pplied in normal insecticidal quantities or repellent to insects, the particles being coated with materials insoluble in water b\it soluble in the alimentary tract of the vermin and belonging to the classes of pro- teins or polysaccharides. Tor exa'^aple, a drug containing rotenone is finely ground and is then introdiiced into a suspension of 20 percent of casein and 3 percent of soap solution. The atomizing of the mass occurs in air of 90°. The re- sulting dust is hardened by a treatment vri.th fornialdehyde or another alde- hyde. Other materials used as coatings are cellulose, vegetable pro- teins, and zein. French Patents: Saliaris (38), in French patent 829,333, issued June 20, 1938, ap- plied for February 18, 1937, claims em insecticide made by absorbing in an artificially prepared colloidal gel the active principles of derris, cube, ajad ajislogous plants and evaporating the solvent. Suitable gels are those of silica, alumina, a mixture of silica and alumina, oxides of titanium, and those prepared according to G-erman patent 435,571. Suitable volatile solvents for the active principles of derris and cube are carbon tetrach-loride, acetone, ether, claloroform, etc. For ercsjnple, derris extract (25 percent active constituents) is dissolved in 20 tines its vreight of acetone, and colloidal silica, is impregnated ■'■/ith this solution and the acetone removed by evaporation. Saliaris (39), in French patent 329,339, issued June 20, 1938, applied for February' 18, 1937, claims a method of suspending or emulsifying in vrater the constituents of derris, cube, or analogous products by the use of a bod;- '.-rith an active cation, tliat is to say, a salt of certain organic bases, having high emulsifying properties. Suitable products are the claloride of laurj^l- 1 rime thy lanimonium, and the salts of the products resulting from the action of the cliloride of oleic acid upon diethyl diamine ethane. Sxarnples are (l) derris powder (rotenone 5 percent) is mixed vdth 10 to ^10 percent of its weight of a "sapamine"; (2) one part of cube extract (rotenone 25 per- cent) is added to 10 to 50 parts of the chloride of lauryltrimethyl- ammonium and emulsified in 40 to 200 parts of water. German Patents: The Imperial Chemical Industries Limited (25), in German patent 655,075, issued September 15, 1938, applied for October 29, 1935, in Great Britain October 29, 1934, malce es.d April 29, 1936. - 4 - Ueu (33), assignor to tlie Deutsche H^drier-Terke Alct.-G-es., in German patent 655,215, issued Sspten-ter 20, 1938, applied for June 27, 1935, claims a nixture of c^'-clic ketones and h^drogenated aronatic h^c^xo cartons as a solvent for rotenone, derris extract, or pj'rethrum extract in the preparation of solutior.s in petroleum distillates or emulsions in vrater. j?or example, 0,5 ^reia pure rotenone is dissolved in a mixture of 10 cc. cyclocaexanone (of 85 percent ketone content) and 25 cc. octohydro- phenanthrene, or a mixture of 10 cc. tetrali^'^dronaiohthalene and 20 cc. decaiiydronaphthalene to '.rhicli is added 50 to 80 cc, of light oil (h, p, 150-250° C.) in order to ohtain a clear solution ^'hich is effective as a fly spray. In another example 0,5 gram rotenone is dissolved in 10 cc. cyclohexanoiie and 10 cc. decahydronaphtlialene or hexahydrox2'-lol and added to 30 grams of a 30 percent aqueous solution of the sodium salt of a sulphated alcohol (vdth 8 to 10 car-oon atoms). A clear solution is thus obtained which is useful, vrhen diluted vrith vre.tev, against cattle gruts and garden insects, Dihydroroter^one and derris extract can he similarly'- used. Other cyclic ketones mentioned are c:''clopentanone and methyl cyclohexanone. Schotte and Gomitz (41), assignor to Schering A.-G. , Berlin, in German patent 671,152, issued Tehruar;^ 1, 1939, applied for iTovember 14, 1931, claim a mixture of rotenone and veratrin-containing drugs for comhating caterpillars. In addition to the mortality data obtained in tests upon Tephroclystia ahsinthiata (Cl.) and given in United States patent 2, 02^-, 392 (see pp. 34-36 of 2-4-:-6) , tests vere made upon cahbage vronns (5th-stage larvae) and 4th-stage larvae of Ilalacosoma neustria vrith Derris malacensis extract and povrdered cuoe root, \rith and '-.dthout sahadilla seed, sho\n.ng the mixtures to be more effective. Boclinulal ojid Gorr (4), in German patent 675,220, issued Ikiy 3, 1939, applied for Ilarch 25, 1934 (addition to 674,488), claim an insecti- cide consisting of derris, pyrethrum, or similar acting drug and an eniul- sifier without an organic solvent. Examples are, 10 parts of rotenone are dissolved in 100 parts of ethoxylated (a) castor oil, (h) oleylalcohol, (c) dodec-"lphenol, (d) iso- octylphenol, or (e) ox:,nohenol-campiian. In another example 100 parts fine derris povrder and 50 parts ethoxjrlated castor oil are warmed '-dth 500 parts ether, and the ether then evaporated. Boclonuhl and Gorr (3), assignors to the I. G. 7arbenindustrie A.-G., in Gennan patent 674,488, issued April 17, 1939, applied for Ilarch 9, 1934, claim an insecticide consisting of an extract of derris, pyrethrum, or similar acting drugs in an organic solvent together with an ether or ester of a polyh2''dric alcohol as an emulsifying agent. Examples are: Twenty-five parts of derris extract are dissolved in 100 parts of a mixture of equal parts of toluene and dioxan plus 3 parts ethoxiflated castor oil. fifteen parts of derris extract are dissolved in 100 parts glycol- monomethyl ether plus 5 parts ethoxylated castor oil. - 5 - T'/elve and' i'ive- tenths pp,r\is derris extract are dissolved in 02.5 parts gl^colmonomethyl ether plus 5 parts ethoxylated olej'-l alcohol. Tv/elve and five-tenths parts derris extract are dissolved in 82.5 parts glycolmonomethj'-l ether v;ith 5 parts etho:x:ylated doce;'"lphenol. Tv/elve and five-tenths parts derris extract are dissolved in 82.5 parts glj'-colrnonom ethyl ether plv.s 5 parts ethoxylated iso-octylphenol. "v/elve and five-tenths parts derris extract are dissolved in 82.5 parts glycolrnonomethyl ether plus 5 parts ethoxylated oxjnphenylccun-phan. Such solutions can he emulsified in v;ater. The f ollov/ing are mentioned as solvents for derris extractives: Alcohol, "benzene, carbon teti-achloride, oils, petroleum. United States Patents: IlcConnell (31), assignor to Tohacco By-Products and Chemical Corporation, in United States patent 2,071,171, issued Pehruarj^ 15, 1937, applied for June 15, 1935, claiins a fujni^ating package consisting of a hermetica,ll7 sealed metallic receptacle ii^.ving its vertical side wall scored to provide knock-outs, and a fiunigant within and only partly filling the receptacle, the fu.nigant consistin,^ of a comDustihle material, an oxj'-gen- supplying material, and a parasiticide material v/hich vdll evolve a parasiticidal vapor during f'airii,[;ation. There are a nujnher of such parasiticides, such as, for exa.;iple, nicotine, anaoasine, pyrethrum, derris, naphthalene, thiocyanates, and su.lfur. A specific mixture contains ahout 67 percent dry powdered tohacco, 14 percent anhydrous nicotine of 98 per- cent purity, and 19 ]percent sodium nitrate. 'filson (44), assignor to the Standard Oil Conrpany of Indiana, in United States patent 2,123,457, issued July 12, 1938, applied for January 16, 1931, claims the method of preventing highly refined viscous petroleum oils from deteriorating and forming acidic bodies, which comprises dissolv- ing in said oil a small proportion of an alkyl amino-phenol in vrhich the allcyl grouiD contains from 1 to 4 carbon atoms. Suito-ble inhibitors are ortho-aminophenol, para-aminophenol, para- methylaminophenol, para-benzylarainophenol, dibutylaiainophenol, or 1,2-amino- napithol. The quantity of inliibitor added to the oil may vary from about 0.002 percent to 0.2 percent. Usually 0.05 percent will be found effective. A tree siDray in the form of an emulsion base may be prepared by emulsifying tvro volumes of oil (technical v/hite oil, saybolt viscosity 50-100) in one voliome of v;ater containing about 5 to 10 percent of an emulsifying agent and a preservative. The emulsifying agent may be gliie, dextrin, gum tragacanth, or gum ghatti, and the preservative may be cresylic acid, formaldehyde, or wood creosote. Insecticides may also be incorporated, such as rotenone, pyrethrum, nicotine, etc. This concentrate mixed with 50 to 75 times its volume of water makes a spray suitable for sensitive foliage and which is particuls,rly effective in controlling codling moth, aphis, fruit tree scale, and other parasites. - 6 - TTotherspoon (45), assignor to Derris, Inc., in United States patent 2,126,854, issued August 16, 1938, applied for April 28, 1934, clains "as a nevr product having insect repelling properties, a mixture of petroleum hydrocarbons alid the oil obtainahle from an extract of derris and similar vegetable sources, the oil having the specific grc-vity at 25° C, of .998, an optical rotation of 100 m.m. of 45°, a saponification value of 24, a saponification value after acetylization of 82.6 and a "boiling range at 760 m. m. of 210°-250° C." ■.".'otherspoon states: "I have found that in the case of derris extract this viscous property is due to the presence of a small amount of the solvent used for extraction and also to the presence of an hitherto undiscovered constituent of derris root, i.e. essential oil of derris. This essential oil vrith, or vrithout, the traces of solvent left in the extract ?:eeps the product in a soft con- dition. "Proper removal of all, or part, of these materials results in a product that is readily pulverizable, thereby erJiancing its coniraercial practicability. ♦ * * This oil possesses the characteristic odor of derris root and is responsible for the insect repelling property of derris products v;hile the insecticide remains undistilled. "Valuable insect repellent preparations may be prepared vrith this oil. For example, an efficient fly and mosquito repellent can be made by mixing l/4 of 1 percent oil of derris vrith 99-3/4 percent of vrhite petrolatum." Solvents mentioned for extracting the active principles of derris are ethyl acetate, benzol, acetone, chloroform, ethylene dichloride, and saf rol. O'Kane (3^), in United States Patent 2,127,526, issued August 23, 1938, ap-plied for August 16, 1934, claims a fungicide or insecticide composition containing a glyceride oil, an oil-soluble insect poison, a hydrocarbon distillate, the hydrocarbon components of vrhich are of sub- stantially uniform molecular size, and an oil-soluble emulsifying agent, the constituents being present in proportions to yield an unsta,ble dis- persion in vrater. O'ICane states: "In addition, the composition may inclu.de substances, either in solution or in suspension in the oil or other contact agent, \;hich substances serve as a stomach poison for insects. Thus an extract of derris or of cube may be added to serve as such stomach poison." A specific example of a composition is as follows: Parts Corn oil 80 Lov; boiling petroleum derivative 20 Nicotine (98 percent pure) 2 Dispersing agent 2 "The emulsifying agents emplo:'ed arc desirably oil-solulDle emvilsifj'-ing agents, particularly v;hen the contact a^-ent is an oil. Such emulsifying agents include sulphonated castor oil, sulphonated vegetable or animal oils in general, triethylamine, potassium oleo-abietate, sodium "bisulphide, etc. These materials render the oil or similar contact agent soluble in the v/ater, or temporarily dispersible therein," Goodliue (19), in United States patent 2,129,517, issued September 6, 1938, applied for January 10, 1938, claims an adhesive for plant spray materials vrhich is noninjurious to plant foliage, comprising a substance remaining in the fractionating column after the removal of solvent and pine oil in the stem and solvent process for the production of naval store products from pine v/ood. This adhesive is suitable for use with pov/dered derris root, pov/dered cube root, powdered pyrethrum flov^ers, etc. It does not accelerate the decomposition of the active insecticidal ingredients in derris and cube and is not injurious to foliage. This adliesive is preferably employed when emulsified in water v/ith amiaonium caseinate containing an excess of ammonia, the insecticide.! mi:cture being applied as a spray. Blount (2), assignor to the Union Oil Company of California, in United States patent 2,133,013, issued October 4, 1938, applied for July 2, 1934, claims an insecticide comprising rotenone oxime, rotenone hydrazone, or rotenone phenylhydrazone, and aryl, allcyl, and metallic derivatives of these. These have some insecticidal value, but in contact v/ith moisture, such as dew, hj'-djrolyze to reform rotenone. Moreover, when the phenyl- hydrazone derivatives are used the regenerated phenylhydrazine displays desirable antioxidant properties for the protection of the regenerated rotenone. This invention may be stated broadly as residing in sup-Tlying to rotenone a stabilizing agent in any of various forms, such as an added oxidation inhibitor or retarder, or in a combined form producing toxic rotenone derivatives, or in combined forms from v;hich regeneration of the rotenone v;ill ta2:e place in use either v;ith or without the regeneration of an oxidation retarder or other agent capable of protecting the regenerated rotenone. Apparently all organic agents employed as oxidation inhibitors or retarders for other purposes, for example as gum inhibitors for gasoline, may be used as stabilizing agents. This includes monobenzylparaaminophenol, and also alpha-terpineol, "vanoline" v/hich is paraphenyl-aminophenol, pyrogallol, hydro quinone, dibenzyl para-aminophenol, and parahydroxyphenyl- morpholene. Similarly other s.gents used as gura inhibitors in gasoline may be employed, su.ch as tributyl-amine and the organic compounds of the non- gaseous members of the fifth group of the periodic system having a valence less tlian five v/hich includes monoaryl alkj'^l-, diaryl mono alkyl-, triaj-jri- and triallcj'-l arsines and corresponding stibines, bismuthines, phosphinea, and vanadines. Also arsine and stibine oxides such as aryl and alkyl aryl arsine and stibine oxides and substituted phen;--! arsine oxides like paraethoxy phenyl-arsine and dimethyl phenyl arsine oxides and other arsenic, antimony, and phosphorus compounds like arsenobenzol, cyclopentyl phenylstibine, phosphobenzol and the like. These organic agents all serve to retard and inhibit the oxidation of more or less readily oxidizable organic compounds, and consequently are useful for the stated purpose. This applies to all other of the knovm oxidation inhibitors included in this definition, and includes sjnines and other amino compounds than those heretofore mentioned. - 8 - In preparing stable insecticides containi/.g rotsnone per se by emplo:/Bent of any one or more of these added agents, the agent is supplied to the derris root or other form of rotenone in v;hatever physical form the insecticide is to be prepared, such as a pov;der or liquid. For exanple, the agent may be dissolved in a '/olatile solvent such as oil of cajaphor sassafrassy, pyridine, safrol, pine oil, "cellosolve" (monoethyl ether of diethylene glycol) and other solvents or in any other solvent having the required solvent or common solvent properties. This solution may then be added in desired quantities to powdered derris root, or rotenone ir.o.y be dissolved in the solution, either of these admixtures being then distributed through an inert powdered base if desired. Thus the rotenone material, before addition to the inert bo.se, viill have been intimately coTjningled v/ith the oxidation retarder and the rotenone-containing pr^rticles thereby siif- ficiently coated or enclosed to protect the rotenone and. insure that the full action of the retarder v/ill be exerted upon the rotenone material v/hen subsequently deposited upon foliage to be treated. Similarly, the solution of oxidation retarder and rotenone may be employed as such or may be intro- duced into v;ater or spray oils, spray oil emulsions, or other oily bases or the like thraagh the medium of the common solvents, such as above mentioned, i*e., pine oils, oil of caiJiphor sassafrassy, cellosolve and the like, the resultant liquids to be used as sprays or otherwir,e as may be desired. Thus in a mineral spray oil base, such as is well Icnovm in the art, paraphenyl- aminophenol, as a retarder, rotenone, and pino oil may be used. Here the pine oil acts as a common solvent for the rotenone, the retarder, and the spray oil, and the resultant insecticidal oil may be emroloyed as a spray. If it be desired to prepare an emulsion, any a.ppropriate soap may be intro- duced. Preferably, neutral or slightly acidic emulsifying agents will be employed such as triethanolamine oleate and stearate, or other neutral emulsifier such as calcium caseinate, and lecithin. In water containing emulsions of this character the retarder v;ill be effective to stabilize the rotenone before and after use. The oximes, hydrazones, and related products resulting from the chemical union with rotenone according to this in%'ention are such as can be dissolved in certain volatile solvents, l/hile the oximes or hydrazones are generally insoluble in the ordinary solvents, such as the petroleum oils used for orchard and garden pest control, they are nevertheless soluble in solvents such as oil of cajnphor, sassafrassy, safrol, pine oils, pyridine, cellosolve, etc. Coleman and Zemba (ll), assignor to the Dov; Chemical Coripan;'', in United States patent 2,133,972, issued October 25, 1938, applied for Aug-.ist 10, 1937, claim a substantially v;ater-free insecticidal spray comprising a noncorrosive organic solvent having dissolved tlierein as insecticidal toxicants a product selected from the class consisting of the extracts of pyrethrin- and rotenone-bearing plants, and a hydroxy-allryl ether of a phenol. A hydroxy-alkyl ether of 4- tertiary bxityl phenol and a i^Rtroleum distillate are specifically mentioned for use with rotenone. An example of results against flies, according to the Peet-urad;'- method, vdth solutions containing rotenone is as follovrs: A solution of 0.1 percent of rotenoue (melting point 163° C.) v^as prepared by dissolving 0.1 gram of rotenone in 12.5 grams of carbon tetra- - 9.- chloi'ide and c'ilutin.;]; to 300 milliliters xirith the usual petroleum diGtillr»,te. The carbon tetrachloride v;as emploj-ed to serve as a mutual solvent, whei-eby, in spite of its relative insolubilitv, the rotcnone v;as obtained and maintained in solution in tlie hydrocarbon oil. This preparation of 0,1 percent rotcnone soliition '-/as emplc:/ed as a base solution to prepare test compositions containing 0,075, 0.05, 0,025, and 0.01 percent rotenoiie. Further test solutions vmre prepared in vrhich the hr'-droxyalkr/l ethers of phenols v;ere employed as a mutual solvent for both rotcnone and petroleum distillate, in v;hich composition such hydroxyalkyl ethers vrere found to servo both as toxicants and as solubilizin^ agents. Such solutions were prepared by first dissolving the desired amount of rotenone in the hydroxyallq'l ether product and thereafter adding the -oetroleum distillate thereto. As the mortality of flies sprayed v;ith rotenone solutions did not reach a con- stant value for a period of approximately 72 hours following the spraying operation, all flies sprayed in this series of experiments v/ere examined at 24-, 48-, and 72-hour periods to deternine the mortality resulting from such treatment. The follovring results are representative of those obtained with compositions containing betv/een 0,01 and 0,075 percent of rotenone and from 1 to 3 percent of various hydroxy-allc^rl ether compounds. Material and concentration 0,01/j of rotenone 0.025;!' of rotenone 0,05;'.' of rotenone 0.075/j of rotenone 0.25f? of rotenone +'3/o of beta-hydroxy-ethyl ether of 4-tertiary-butyl-phenol 0,05'/j of rotenone + 3^ of beta- hydroxy-ethyl ether of 4- tertiary-butyl-phenol 0.075fj of rotenone + Z'^o of beta-hydroxy-ethyl ether of 4-tertiary-butyl-phenol 0.01^ of rotenone + 3^ of beta- hydroxy-ethyl ether of 2-cyclo- hexyl-phenol Average knockdo^irn in 10 lean mortality in 24 48 72 minutes hours hours hours Percent Percent Percent Percent 75 7 18 25 75 8.6 25.2 37.5 88 11 42,3 59,4 89 41 73,2 93 25 97 28 74 81 79.2 88,2 99 34 72.6 92.2 ;i.3 52 56.6 „,„'»S'bo.«> - 10 liaterial and concentrati( Average Icnockdovm Mean mortality in — in 10 ninutes Percent 24 hours Percent 48 72 hours hours Percent Percent 0.025^ of rotenone + Z^o of beta- hydrox^'-'-ethvl ether of 2 c^xlo- hexyl-phenol 0,05;?! of rotenone + 3^ of beta- h^.'droxy- ethyl ether of 2-cyclo- hexyl-phenol 95 61 71.8 84.2 91.2 Simultaneous runs v;ith 3-percent solutions of the beta-hydroxy-ethj^l ethers of 4-tertiar:''-butyl-phenol and 2-c5'-clo-hexyl-phenol gave the follow- ing results: •laterial and concentration Average Icnockdovm in 10 minutes Mean nortality in 24 hours 4C hours 72 hours 3fj beta-hydroxy-ethyl ether of 4-tertiary-butyl-phenol Z^o beta-hydroxy-ethyl ether of 2-cyclo-hexyl -phenol Percent 94 Percent Percent Percent 81.7 34 24 52 28 54 31.1 Another series of tests shov'red conclusively that the addition of the hydroxy-alk7/l ethers to petroleum distillate solutions of pyrethrin and rotenone appreciably increased their "knockdovm" rate. That is to say, the combination of materials acconplished a more speedy control of flics sprayed therev/ith. These hydroxy-alkyl ethers of phenols stabilize solutions of pyrethrins and rotenone a-ainst deco.-,rposition 'oir light. ?iesults v/ith rotenO';e v;ere as follovrs: - 11 Material and concentration Official control insecticide Average iiean r.iortalit:/ in — Icnockdovm in 10 24 48 72 minutes hours hours hours Percent Percent Percent Percent 100 49.7 51 51.5 Official control insecticide after e.^oDosure to sunli-^ht for 12 davs 0.1/3 rotenone 0,1^ rotenone after exposure to sunlight for 12 da^s O.l^j rotenone + 3^ "beta-h^drox;','-- ethyl ether of 4-tertiar-'-"butj'l- phenol 0.1^ rotenone + 3^ heta-h^droxy- ethyl ether of 4-tertiary-hutyl- ?nenol after exposure to sunlight or 12 days 93 21 23.6 26.3 92 15.6 48.3 75.6 42 35.3 58.3 93 84.3 11.3 99.3 93 Schotte and Gornitz (40), assignors to Schering-Xahlhaim A.-C-. , Berlin, in the United States patent 2,135,868, issued IToveiaher 15, 1938, applied for Decemher 12, 1933, in G-ermany June 30, 1932, claim as an insecticide a finely divided mi^cture, solidified from the molten state, of an insecticidal vegetable material and a carrier suhstance, the said carrier sxibstance "being solid at ordino.ry temperatures, "bvit melting "below carbonization temperatures of said vegeta"ble material and in its molten state "being capo>"ble of ex- tracting the active insecticide from said insecticidal vegetable material. Tor example, derris root is mixed v/ith molten naphthol in the proportion of 3:5, and the solid mixture is ground v.dth a suitable dilut- ing agent, such as talc. The product is highly efficient against cater- pillars and possesses also fungicidal properties. ComiDarative tests each made uith 50 caterpillars of Liioari s monacha (5th stage), 20 kgs, being distribu.ted on 2,5 acres, gave the follovdng ■ results: A, Mixture of 80 percent of an inert pov/der and 20 percent of derris root Test 1 ::est 2 Test 3 Killed Killed Feeding after after condition 7 days 8 days 20 30 Strong 22 33 Strong 15 Strong o: - 12 - lixture of 80 percent of an inert -jtoviCer and 20 percent the derris-root-naphthol mixture . . Killed Killed Peeding after after coiidition 7 da^'s 8 da^s Test 4 32 39 V.'eak Test 5 33 41 Not feeding Test 6 29 35 Tfealc Another example is, equal parts ipyrethrum olossous and derris root are mixed v;ith molten naphthalene in the proportion of 3:5 and tlie mixture groruad v;ith alimina. In place of naphthalene or naphthol the follovang may be used: Sodium acetate, borax, carhazole, th;-mol, isothjnnol, and crude anthracene. Molten aliphatic, alic^clic, or cyclic hydrocarbons, terpenes, and inorganic salts such as crj-stallized sodium sulphate may "be used. The insecticides such as obtained according to the present inven- tion may also be combined v;ith other insecticidal substances, such as arsenic compounds, or v;ith fungicides, such as copper compounds, and ^rith adhesives, such as lime-soaps, or fillers, such as talc, alumina, china cla;^'', bole, and the like, VJhen using them for spraying purposes it is useful to add Turkey red oil or other salts of sulphonic acids. Sibley (42), assignor to the Monsanto Chemical Companj^, in United States patent 2,138,516, issued Noveraber 29, 1933, applied for October 16, 1936, claims an insecticide having as an active ingredient a material selected from the class consisting in rotenone and pyrethrum compositions and a preservative thereof selected from the class consisting in diaryl arylene diamines, aldehyde derivatives thereof, and the product obtained "by reacting a diaryl arylene diamine v;ith an aldehyde aJid an alcohol. Specific examples of diarj'-l ar--lene diamines v/hich may he used successfully as stabilizers of the toxicity effect of rotenone and pyrethrum insecticides are diphenj'-l p-phenylene diamine, di-phenyl m-phenylene diamine, diphenj'-l o-phenylene diamine, di-alpha and beta-naphthyl o-, m- and p- phenylene diamine, ditolyl o-, m- and p-phenylene diamine, di-biphenj^l o-, m- and p-phenjaene diamine, diphenyl dixylyl and ditolyl benzidine, and di-, 0-, and p-biphenyl benzidine. As examples of derivatives of diai^l ar^-lene dianines, vrhich are enrplo/ed according to this invention, aldehj'-des are reacted therewith, and the aldehyde amine products so formed employed as staoilizers of said rotenone and pyrethrum containing insecticides. Thus forriialdehyde, acetal- dehyde, hutyraldehyde, and heptaldehyde are reacted vith the diaryl arylene diamines defined above, and the resultant products enploj'-ed as stabilizers of insecticie^.l preparations conprising rotenone and pyrethrum. As a further and more preferred embodiment of the present invention the diarjrl arylene diamines of the present invention and as above disclosed are reacted sij.mltaneously vdth an alipk-tic aldehyde and an alcohol to produce exceptionally efficient stabilizers of insecticides containing, as an active principle, rotcnone and pyrethr"ura and related compounds, -hus aay one or more of the diaryl arylene diamines defined above are reacted simultaneously v/ith an allpli^.tic aldehyde, for example, formaldehyde, acetaldehyde, "butyraldehyde, heptaldehydc, and analogous aliphatic aldehydes, and an alcohol, for example, meth'"'l, ethyl, "butyl, propyl, amyl, and analogous alcohols, also benzj'-l alcohol and cyclonexanol. Varying proportions of the ptreferred class of stabilizers may be em- ployed. Preferably, however, the quantity employed varies from about 0.5 percent to 10.0 percent, based on the xireight of the insecticide. Paloon (13), assignor to Hoinmond Faint and Chemical Company, Inc., in United States patent 2,144,565, issued o'anuary 17, 1939, applied for October 24, 1935, claims an insecticide coaiprising an easily oxidizable organic vegetable toxic material of the grovip consisting of pyrethrjjn and rotenone and a phenol of the group consisting of lignocol, guaiacol, cresol, thjonol, phenol, eugenol, resorcinol, pyrogallol, and hydroquinone to stabilize the seune. Other materials that may be used as oxidation inhibitors are p-amino- phenol, aniline, benzidine, di-beta-naphthylamine, diphen.3'^larnine, hexamethylene tetrpxiino, alpha-naphthol, beta-naphthol, pjid phenyl alpha-naphth:^lojnine. Hydroquinone is the best oxidation inhibitor, and guaiacol is second best. The stabilizing compound is added to the extent of 0,0025 to 1.5 percent by vreight of the total insecticide. Solvents that may be used as. a vehicle, such as alcohol, acetone, carbon tetrachloride, ethylene dichloride, neutral petroleujn oil, kerosene, gasolene, mineral spirits, etc., or nixturos of tvro or more of these solvents, vary in their respective abilities to disperse the inhibitor or negative catalyst used in any instance so that different proportions of any particular catalyst are necessary './ith different vehicles. Acetone, for exsLMple, v/hich may contain some moisture, requires more nega.tive catalyst to inhibit oxidation thaft a vehicle of alcohol. Vehicles con- taining sulxohonated oils or moisture require larger proportions of in- hibitors than those not having these ingredients therein. Examples of su.itable compositions are: Composition Ho. 2 Percent by weight Derris 3.00 Beta naphthol .003 Eth^rlene dichloride 2.00 Alcohol 94.97 - 14 - Percent b;- Coinposit.ion iJo. 3. vrei^-ht Pyrethrun , 1.2 Rotenone 1,0 Hydro quiiione .0025 Carbon tetrachloride 1.0 Alcohol 06.7975 Composition Ho. 5 Percent "bj v/ei.^ht Derris 2.5 C-uaiacol .025 Alcohol 97. -1-75 Paloon (14), assignor to Ilaciiiond Paint and Chemical Conpany, Inc., in United States patent 2,144,367, issued January 17, 1939, applied for October 24, 1933, divided and this application Lay 14, 1930, claims an in- secticide comprising a volatile solvent vehicle, an easil" oxidizable organic vegetable toxic material of the group coasistin.T of pyrethrum and rotenone dissolved therein, and a naphthol o2' tlae group consisting of alpha naphthol and beta naphthol to stabilize the sap.e. The amount of inhibitor added varies from 0,05 to 1.5 percent by v/eight of the total combination. An example is: Percent by v;ei,'rht Lerris 3.00 Beta- naphthol .003 Ethylene dichloride 2.00 Alcohol 94.97 Faloon (15), assignor to Hammond Paint and Chemical Compan;^, Inc., in United States patent 2,144,368, issued January 17, 1939, applied for May 14, 1938, claims an insecticide coiiprising an easily oxidizable organic ve;;e table toxic material of the group consisting of pyrethrum and rotenone and naphthyl- ainine to stabilize the same. Some of the naphthylamines and derivatives v.'hich have been found satisfactory as oxidation inhibitors or negative catalysts in the present process are naphthylamino, phenyl alj^ha-naphthylamine, o.nd di-beta- naphthylamine. The amount of inhibitor added may vary from 0.05 to 1.5 percent by weight of the total composition, Faloon (15), assignor to Ham.nond Paint and Chemical Company, Inc., in United States patent 2,144,369, issued Januf».ry 17, 1939, applied for May 14, 1938, claims an insecticide comprising an easily oxidizable organic - 15 - vegetable toxic material of the Q^owp conaisting of pyre thrum and ro tenons and an aromatic amine of the group consisting of di;'-ihenj'-lpjnine and "benzidine, Hexamethylenetetramine and para-ai.^.inophenol are also suitable. The solvents ixsed and t?ie amount of orcid.ati on i.ihibitor axlded are the same as described in -oreviouo iDatents by ?aloon (United States r^atents 2,144,366; 2,144,367; 2,144,368). G-oodiiue (21), in United States loatent 2,146,257, ir,suod Tebruary 7, 1939, applied for September 23, 1S38, claims an ad.h3sive for insecticides comprising the reaction products of furfural v/ith aromatic amines of the group consisting of beta-naphthyl-amine, aniline, and p-toluidine. This adhesive can be used to prevent t'le removal of sprayed or d.^sted insecticides and fungicides from plants by rain, vrind, or a combina,tion of these factors. More particularly this invention rela.tos to a group of chemical compounds or mixtures t'lereof , v.rhich, although nonadJiesive v/hen applied to plants v;ith the insecticide, becone adhesive, resinous, taoky^ and insoluble in uater after exposure to sunlight. This invention can be used v;ith spray insecticides, but it is especiallj" ada-pted for use vrith insecticides applied in the form of a dust. One advantage of this adJiesive is that any amount of the material ma,7 be incorporated without materially changing the physica]. i^roperties of the dust. Another advantage is tlia.t no dependence need be placed on moisture to cause the material to a,ct as an adhesive. And still another advantage lies in the storage of such dusts containing the adiiesive, since it is easy to protect the material from light in inexpensive bags, thus eliminating the difficulties due to caking v;hen adhesives sensitive to moisture are \ised. Several methods of incorjporation vrith the insecticide maj'' be used. For use vdth dusts simple mixing of the dry pov/dered light-sensitive compomid v/ith the insecticides gives good results. A better practice, however, is to grind the insecticide v;ith the adiiesive in a ball mill or other effective grinding machine. A still better but more complicated method of incorporation is to add the light-sensitive adhesive to the dry insecticide in the form of a solution in v/ator or organic solvents. After removal of the solvent the adiiesive and insecticide mixture is ptilverized before dusting. An amount of adiiesive equo.l to from 5 to 25 percent of the weight of the insecticide is recommended. ITor use with sioray insecticides, t]ie light-sensitive co-.vposition may be dissolved in the v;ater or added in the form of a suspension, depend- ing on the solubility of the substajice to be used as the adiiesive. 2his adhesive is effective when used v/ith powdered derris. Goodhue (20), in United States patent 2,146,253, issued Tebniary 7, 1939, applied for Septem.ber 26, 1938, claims an adjiesive for insecticides comprising the reaction products of furfural v/ith hetones of the group consisting of acetone, methylethyl-ketone, acetoi-)henono, benzophenone and 2-naphthyl ketone. The properties and uses of this ac'hesive are similar to those of the products described in United States patent 2,145,257. This adhesive is effective when used with pov/dered derris. T. 16 T Kilgore (25), assitjnor to the Kilgore Devolopraent Corporation in United States patent 2,149,917, issued March 7, 1939, applied for April 24, 1936, claims a process '.;hich comprises the extraction of rotenono and other compounds having insecticidal properties from rotenone-h earing plants "by means of an ester helonging to the class of organic compounds knovm as delta-epsilon-unsaturated-alpha-garama-diketo carhoxylic esters of the general f onnula, R R ')C=C-.CO-CH -CO-COOR_ ■n 2 3 ^2 v;herein B.-^ and Rp are the ssane or different organic radicals or respectively one organic radical and one hydrogen atom, R^ is an aHq'^l radical or a hydrogen atom, and R is any organic radical forming an ester of the carhoxyl group, Not only do these esters effectively extract rotenone from such plants "but they carry the extracted rotenone into solution in sprayo.lDle vehicles such as hydrocarbon solvents, thus effecting a direct transfer of the rotenone from the plant to the final insecticide solution. The follov;ing are examples; Example I One part of a drj'-, powdered derris root containing 5 percent of rotenone is intimately admixed vdth four parts "by v;eight of mesityl oxide oxalate, n-butyl ester, ^ C=CH-CO-CH -CO-COOC^H Tlie paste formed "by this mixture is then heated at approximately 100° C. for an hour and the solvent removed. The extract so ©"btained has a red-yellovr color and contains approximately 0,8 percent rotenone. These extractions are suita"bly made between 30° and 200° C, the use of materia,lly higher temperatures causing decomposition of the solvent. It is frequently advisable to make those extractions in an inert atmosphere, such as nitrogen or carbon dioxide, especially v/hen a more elevated temperature is used, in order to prevent excessive coloration. Example II One part of dry, pov;dered root of D erris elliptica containing 5 percent of rotenone is mixed with five parts of raesit^-l oxide oxalate, n-butyl ester. This mixture is then heated to 150° C. for half an hour in an atmosphere of nitrogen. The solvent containing the extracted rotenone is then removed from the mixture. - 17 - Example III One part of dry, powdered root of D. ellirttica containing 5 per- cent of rotenone is mixed v/ith five parts of mesityl oxide oxalate, n-butyl ester. This mixture is then heated to 150^ C. for half an hour in an atmosphere of carbon dioxide. The solvent containing the extracted rotenone is then removed from the mixture. Example IV Pour parts of pov;dered root of D. elliptica containing 5 percent of rotenone are maceratrd ^dth five parts "by weight of ethyl-3-methj'l-3- heptene-2-1 oxalate, n-C H CH=i-COCH_ COOC^H^ and treated as in Example I., The resulting extract \/as of a deep straw- yellow color which formed an almost colorless solution in kerosene. A 4 percent solution is then made "by diluting 1 part of the extract v/ith 24 parts "by volume of a suita'ble carrier, as l-erosene. This diluted solution now contains, in addition to the insecticidal properties of the solvent ester, those of the rotenone, and any other insecticidal su"b- stances so extracted from the plants. This solution is a finished in- secticide having desirable concomitant physical properties, such as absence of undesirable odor, little or no color, and good atomization properties. The exEiraples that follov; show the extraction of rotenone from suit- able plant materials now used' commercially as a source of rotenone ^ and the consequent production of a new composition having strong insecticidal properties. The extracts used in the work reported here are made by forming a paste or heavy dispersion of the povrdered plant materials, roots, in the ester vrherein 10 parts of the root are admixed with 25 parts by weight of the ester. This mixture is then heated at 100° C. for 1 hour. The extract is removed by filtration, yielding in most pases extracts liaving straw*-- yellov; to brown-red color. Pour-percent solutions of each of the extracts are then made, using a deodorized kerosene solvent suitable for insecticidal tests and filtered vmenever necessary. Tlie insecticidal effects of these solutions are then compared v/ith that of similar concentrations of the esters alone by bio-assays using house flies under identical controlled conditions. The results of these tests are shown in Table 1, ' The bio-assys vrere made by using 5-day-old houseflies ( Ilusca domestica). The flies v/ere caged in 5 x 5 inch, cylindrical, all-wire cages, approximately 100 flies to the cage. Each cage v/as separately ex- posed to the same amount of finely atomized spray or fog from wliich the larger droplets had been removed. This v/as accomplished by using an L- shaped pipe, 6 inches in diajm«ter and 1 foot long on each side of the elbow. - ib - moiinted vdth one side of the L in a vertical position* The cage of flies v/as then suspended in the top of the upright pipe, and the atomizer v;as placed at the other end of the L. ?ive cuhic centimeters of the diluted ester of the extract was then atomized into the pipe at the "bottom end, producing a highly dispersed, smokelike fog, v;hich v;as driven evenly throughout the cage containing flies. The cage of flies so exposed to the atomized insecticide vra,s then removed and set aside for 24 hours, when the number of "dead" was determined. "Dead" here included those flies v;hich v;ere paralyzed and unable to feed after 24 hours. This is a common prac- tice in rotenone "bio-assays. In addition to the a"bore "bio-assays showing that rotenone is removed from rotcnone-'bearing plants Ly extraction v;ith the esters which are shovm herein, the colorimetric method of Rogers and Calainari shov/ed strong posi- tive tests for rotenone in each case, shovdng that rotenone had been carried into solution in the finished insecticide. Table 1 Biological record shov;ing increase in the kill of flies due to insocticidal material extracted from rotenone-"bearing plants by the esters. Esters used as cxtractants A. Derris root extractions 1 Mesityl oxide oxalate, ethyl ester 2 Ilesityl oxide oxalate, n-butyl ester 3 Ilesityl oxalate, iso-butyl ester 4 Mesityl oxide oxalate, scc.-c.unyl ester 5 Ilesityl oxide oxalate, cyclohoxyl ester 6 Ilesityl oxide oxalate, tctrahydrofurfurj'-l ester 7 Acetalacetone oxalate, n-butyl ester 8 n-Butyralacetone oxalate, ethj'-l ester 9 3-Methyl-3-pentene-2-one-oxalate, ethyl ester 10 3-Mothyl-3-heptene-2-one-oxalate, ethyl ester 11 Tetrahydroacetophenone oxalate, ethyl ester Percent killed by — Pure Sster and ester extracted only rotenone 9 100 30 100 16 100 53 100 17 100 4 85 80 100 6 95 45 85 2 100 4 98 B. Cracca virginiana root extraction 12 ilesityl oxide oxalate, n-butyl ester 30 67 C. Cube root extraction 13 Iloaityl oxide oxalate, n-butyl ester 30 62 Suitable esters for use in this process are the following: Mesityl oxide oxalate, ethyl ester; mesityl oxide oxalate, n-butyl ester; mesityl oxide oxalate, iso-butyl ester; mesityl oxide oxalate, sec.-amyl ester; mesityl oxide oxalate, cyclohex:/l ester; mesityl oxide oxalate, tetrahj'-dro- furfuryl ester; acetalacetone oxalate, n-butyl ester; n-butyralacotone oxalate, ethyl ester; 3-methyl-3-pentcno-2-one oxalate, ethj'-l ester; 3- mothyl-3-hopteno-2-one oxalate, ethyl ester; tetrahydroacetophenone oxalate, othyl o3tor. - 19 - Christraann and Jayno (lO), assignors to American Cyanamid Companj'", in United States patent 2,151,551, issued March 21, 1939, applied for Hovemlier 13, 1932, claim rotenone containing a stai)ili2cr selected from a class consisting of aminopiienols, dichloroaniline, salicylic acid, and anthranilic acids. The stabilizer raaterial may "be incorporated in the rotenone in substantially any desired or convenient manner, Tor example, the rotenone may be dissolved in a solvent, such as acetone, which is also a solvent for most of the stabilizers, and then the stabilizer may be incorporated therein, Q^5.ite satisfactory results are obtained by the use of an acotone solution containing 0.3 percent of rotenone and 0.1 to 0.3 grojn of any of the above indicated stabilizers per 100 cubic centimeters of solution. Other solvents or mixtures of these solvents vith acetone may likevrise be employed. Other compounds suitable for stabilizing rotenone, especially v/hen it is used for mothiDroofing fabrics, a::c methyl- and ethyl-chloro-anilines, dichloroaniline, mono- and dichloro-anthranilic acids, polyhydroxy phenols polj'"amino compounds, and mixed hydroxy-amino, Ivdi'ox^r-carbo::;'', and amino- carboxy compounds. Uitro substituted phenolic amino compounds may be used. A mixture of 2.5-dichloro-aniline v;ith oleic acid is pr.rticularly satisfactory. Marsico (30), in United States pv^tont 2,150,241, issued May 16, 1939, applied for June 18, 1935, claims in an insecticide a rotenone solution consisting of coranercially pure (90 percent) rotenone dissolved in chloroform liniment in about the proportions of 1 grcjn of rotenone to 40 cc. of chloroform liniment, the chloroform liniment being composed of about 30 percent chloroform and about 70 percent camphor soap liniment, and the CDjnphor soap liniment being composed of hard soap, camphor oil, oil of Rosemary, alcohol, oJid distilled water in the proportions of hard soap 50 gr., crunphor oil 45 gr., oil of Rosamary 10 cc, alcohol 700 cc, and suf- ficient distilled vrater to raalce 1,000 cc. of the camphor soap liniment. A pyrethrin solution is similarly propo^rod (2 ounces of flov;ers to 400 cc, of chloroform liniment). Solutions are also made of copper sulphate in v;ater (2 ounces to 500 cc.) and green soap in wa'cer (l ounce to 200 cc). The above described rotenone, pyrethrin copper sulphate, and green soap solutions are then nixed together cjid added to pine oil rjxd comiiiercially pure or 90-percent nicotine, in the proportions of substantially 20 percent of rotenone solution, 20 percent of pyrethrin solution, 10 percent pine oil, 15 percent green soap solution, 30 percent nicotine, and 5 percent copper sulphate solution, Marsico states: "Tfliile the rotenone solution, pyrethrin solution, nicotine, and copper suljDhate solution are individually very effective poisons, I have found that they are rendered comparatively ineffective vrhen liighly diluted in vrater for spraying lourposes unless all of them arc employed together and in substantially the proportions set forth o-bove. At the same - 20 - time, the simtultsjieous use of all of these poisons, or active ia^redients na^urallv v.'idens the raiii^'e of use and ■ effectiveness of the insecticide as reg;o,rc-.s the kind of insects v;liich may "be destroyed thareoy. " ?ho::ipson-;(43)., assignor to Hercules Pov.'der Co., in United States patent 2,1SC>5?$ issued May 30, 1939, applied for April 23, 1937, claims an insscticidal composition comprising an additive ether of a terpene and an alcohol, a contact insecticide e-troctsd from a plant "bodj'-, and. a carrier. Claim is aiao BiadjD for an insecticidal composition comjorising an additive ether of a terpene and an alcohol, and a pov^dered plant insecticidal material. Suitable toxic materials for addition to the terpene ether are, for example, the active principles of pjTethrum or of rotenone-h earing plants; nicotine; nicotine compounds, as nicotine sulfate, etc.; alipliatic thiocyanates, etc. According to Thompson, mixtures of terpene ethers vrith certain other insecticidal materials have far greater to"ic action on insects than that of either componeirt of the mixture alone; also certain of the terpene ethers have a definite action in preventing the deterioration of other insecticides, such as, for example, the active principles of pyrethrum and of rotenone-hearing plants, etc, and prolonging their useful life. The terpene ethers used in the compositions in accordi?.nce v;ith this invention are chai'acteri?:ed by containing an ether linka.ge connecting a terpenic group v;ith another group, and may "be prepared in either of two ways. They may he prepared "oy the etherification of the hydroxyl group of a terpene alcohol v/ith a.nother alcohol, or they may "be prepared "by the direct addition of an alcohol to a dou'ole "bond of an ujasaturated terpene compound. The latter type ethers will, for convenience, "be termed "additive" terpene ethers. The alcohol used as the etherifying agent may, in either method, "be a monohydric alcohol or a polylij-dric alcohol. The monohydric alcohol may he, for example, methyl alcohol, ethyl alcohol, propyl alcohol, butyl" alcohol, amyl alcohol, ethylene glycol monethyl ether, ethylene glycol monohutyl ether, diethylene glycol moneth;:^ ether, etc. The polj'-- hydric alcohol may he, for exaiTiple, eth^'-lene glycol, diethylene gljrcol, glycerol, etc. The terpene alcohol used to prepare a terjoene ether by the etherification of its hydroxyl group maybe any terpene alcohol having a reactive hydroxyl group, such as, for exairii^le, alpha terpineol, borneol, fenchyl alcohol, etc. Crude terpene cuts rich in teri^ene alcohols may likev;ise be etherified. Such ethers may be readily prepared by well-knovm methods. The unsaturated terpene compound used to prepare', a terpene ether by the addition of an alcohol at a double bond may be, for example, alpha pinene, nopinene, dipentene, teroinene, terpinolone, phellandrene, sylvestrene, alpha, terioineol, beta terpineol, carene, camphene, bornj'-lene, etc. These terpene compounds do not need to be in pure form, but may be reacted in the form of a crude mixture. Tims, in place of the several pure ter^jene compounds, crude natural mixtures, as for example, turpentine, pine oil, etc., or crude fractions of the riixtures may be reacted without the necessity of isolating the resulting ethers in their pure state. ^ 21 - for use in the irsecticid£'.l compos! ticns in accordance with this invention. The resultini^ mixbires of terpene ethers may be, and from the st:.indpoint of econori^r will desirably !:<>, iised per ?,e in the^e insecticidal compositions. V-Tiere herein a terpene ether is specified, it vrill be understood to mean either a pure ccm-oound or a ini:;tui'e preparod froi-i a mi.^od terpene fraction. Specific compositions conprise the additive ether of ethylene glycol and turpentine, rotenono, aJtid a carrier; also the additive ether of ethylene glycol and turpentine and powdered derris root. A highly active insecticidal dust may "be prepared in accordance v/ith this invention. Such a dust vTiil comprise a terpene ether in- coiporated into a powdered insecticidal material such as, for exajnple, ground pyrethrum flowers, powdered derris root, powdered cube, etc, JPaloon (17), assignor to Hammond Paint and Chemical Co., Inc., in United Str.tes patent 2,168,064, issuod August 1, 1939, applied for June 11, 1935, claims an insecticidal com-oosition having asprincipal toxic ingredients powered organic plant material from a group con- sisting of derris, cube, or pyrethr-jim coated with a light-reflecting pigment in sui'ficient quantity to inhibit the loss of toxic principles of said insecticide when exposed to Xig.ht, such pigment being selected from a group consisting of titcini\;m oxide, tibanated lithopone, and zinc oxide. The light-reflecting rabstpjices particularly applicable as an ingredient of comraercial insecticides are, preferably, titanium- containing compounds such as titanium oxide, calcium titanox, barium titanox and titanatad lithoponos, antimony oxide, lithopone-zinc sulphide, zinc oxide, highly calcined gypsum, and barium siilphate, Tj'-pical formulae for the novel insecticides are the following: formula A - 5 -percent rotenone-bearing root (ground), 15 percent; or pyrethrum powder, 25 percent; titaniujn oxide base pigment, 12 percent; kaolin or other inert material, 63 to 73 percent, Titanium oxide base pigment consial^^ prijnarily of titanium oxide In combination \d.th barium sulphate cr a calcium base, and, vhile the above percentage of this substance is preferred, the percentage may vary with reasonable limits. For instance, the titanium oxide base pigment may be increa3ed to 20 percent, v/ith a proportional reduction in the percentage cf inert carriers. In the place of the titariom oxide base pigment, tit.'iiium oxide alone maybe employed, 6r there maybe a mixture of the base pigment and the oxide. Other forrmilae substitute 12 percent of antimony oxide, or 15 percent of lithopone zinc sulphide pigment, or 75 to 85 percent of barium sulphate or calcined gypsum for the 12 percent of titanium oxide base pig- ment in Formula A. Jaloon states that pyrethrum and rotenone dusts made according to Jorinala A exert a toxic effect on both the cabbage worm and the bean beetle for a period 65 percent longer than the active life of untreated dusts. " 22 - Adams and Nikitin (l), asaignor to the tmstees of the Crop Pro- tection Institute, in United States patent 2,172,314, issued Septemher 5, lG39j -applied for October 28, 1335, claim a dusting corposition com- prising a yoppor fuiigicidal ocmpoiiiid, a zeolite from the group consisting of alkali and alkaline earth metal zeolites, and an insecticide from the group consisting of pyrethrum and derris, said zeolite acting to stalailize the dust and prevent caking thereof. Vath a couposition containing 10 parts sodium zeolite, 10 parts copper sulphate, 7 parts derris, and 75 parts clay, there was more tlian 90 percent control of the Mexican bean "beetle, v.dth no copper injury to foliage. Lind (28), assignor to Lin-Tox Corporation, in United States patent 2,173,849, issued Septomler 26, 1939, applied. for September 4, 1937, claims an insecticide comprising an aqueous solution of a soap of linseed oil, fatty acids, and a contact poison. A tT-pical composition has the follov/ing formula: Linseed oil soft potash soap (dry "basis'* , 21,79 percent; total water, 77,93 percent; rotcnone (e.g., from derris root), 0.07 percent; other derris extractives, 0.21 percent; to Lai, IGO pc-rccn'j. The rotcnone and other extractives may be obtained by extracting derris root v;ith acetone or other suitable solvent or extracting agent, Jor exyj^rple, the derris extractives may be used in the form of an acetone solution containing about 5 porccnt rotcnone, 15 percent other extractives, and 80 percent acetone. If stica solution is used as such, the above fornrtila v;ould contain abotit 1.12 percent of acetone in lieu of the same percentage of v;ater, I'or amplication to exterminate the Japanese beetle, it is diluted by mixing 1 volui'ae v;ith 9 volumes of water and applying the diluted solu- tion with any suitable sprayer, e. g., of the atomiser type. i^nTithor. composition v;hich Is stated to h.ave a rapid lethal effect on Japanese beetle contains the foll6v;ing, v;hen diluted ready for use: Linseed oil soft potash soap (cry basis), 1 percent; rotenone, 0.0035 percent; other derris extractives, 0.010 percent; nicotine, 0,005 percent, Bousquot (5), ascignor to E. I. du Pont de Nemours ond Company, in U. S. patent 2,1G6,119, issued July 18, 1939, applied for October 3, 1936, claims an insccbicidal composition containing as an essential toxic in- gredient a butyl amide of io,ll-undocylenic, acid. The amide is generally, though not necessarily, employed in conjunc- tion with one or more other liquid, soniliquid, or solid insccticidal or noninsocticidal sxibstances or co.rriers, such as a substance of the type commonly used in formulating insccticidal compositions. A few such sub- stances or carriers are mentioned as tjrpical: Zeroscne, gasoline, pyrethrura, derris, talc, thiocyanatos, phthalates, and pine oil. Bousquet and Salzberg (6), assignors to E. I. du Pont He Nemours and Company, in U. S. patent 2,106,118, issued July 10, 1939, applied for - 23 - carbox;:,'"lic acid amide having a hntorocyclic radical and an aliphatic hydro- carbon residue of at least six carbon atons. Ah example is 4-(lO,ll-undecylenoy!I.) niorpholino. This amide is generally, though not necessarily, employed in conji'nction v;n th one or more other liquid or solid insecticidal or noninsccticidal substances, such as the type of subst:incos coranonly iised in formulating insecticidal compositions. Such substances are numerous, and only the following few are mentioned as tj'pical: ICerosene, gasoline, pyrethrum, derris, t^lc, thio- cyanatos, phthalates, and pine oil. Boyce (7), assignor to tho Govcnunent and People of the United States, in United States patent 2,191,421, issued Pebrua.ry 20, 1940, anplicd for December 2, 1937, claims an insecticidr.l dust comprising as a major con- stitutent v/alnut-shell floujr pf smaller particle size than 100 screen mesh and a relatively small amount of an insecticidal toxicant, selected from the class consisting of the extracts of rotenone- and pyrethrin-bearing plants, intimately incorporated therevdth, V/alnut-shell flour of 250-400 screen mesh particle s±'aq was com- pounded with cube, derris, and other vegetable products of high rotenone content. Compositions containing from 0.5 to 1.0 percent by v/eight of rotenone were dusted on insect- infastod plants and deciduous and citrus trees at 1 pound per tree. All parts of the dusted trees were found to be covered "by a uniform deposit of the product, and no injury resulted therefrom. In- sect pests v/hich these compositions were foxand to control were the citrus thrips, the greenhouse thrips, the flov;er thrips, citrus aphids, and the orange tortrix. Other ligno-cellulosic materials ma^' be employed in finely divided form substantially as described above in the preparation of insecticidal du«tihg compositions, such as tho flour prepared from coconut shells, pecoii shells, Brazil nut shells, poach pits, cherry pits, apricot pits, olive pits, plum pits, cedar wood and bark, birch, and similar ligno-cellu- iosic products. Brubakor (8), assignor to H. I. du Pont de Nemours £>:ad Com:pany, in United States patent 2,098,942, issued November 16, 1957, applied for June 17, 1936, in Oerraany June 18, 1935, claims a composition of matter suit- able for protecting materials ago.inst parasitic attack comprising a disper^ sion of a parasiticide in a so?Lution of a salt (e.g., the acetate of deace- tj'lated chitin) of a polymeric amino-nitrogen containing bod;^ substantially insoluble in water and in 5 percent aqueous ammonia but soluble in at least the stoichiometrical coaount of 2 percent aqueous acetic acid and capable of forming a coherent film therefrom. Any dispersable liquid or solid parasiticide compatible with the salts of the amino polymer may be used in this invention, for examiple, derris pow- der, Carsv/ell (9), assignor to lionsanto Chemical Company, in United States patent 2,192,894, issued March 12, 1940, applied for November 23, 1936, claims insecticidal compositions 'containing derivatives of cyclohexylamine, e. g,, N-amyl-N-benzoyl-cyclohexylamine, v;hich is especially valiip.blc for the . - 24 - concrol of Icrf hoppers on apple trees and gra.pevines. 3uita"ble concentra- tions to use for this pur-ose are prepar?.tions containing a'bout 0,1 percent of the aaiyl'ben2o:';lcj-clohe:^laJiiine in an emulsion made with the aid of a sulfonated castor oil or a similar netting o-r enulsifying agent. In such uses the compounds of the invention act similarly to materials such as nico- tine, pyrethmm, derris, rotenone, and proprietary alipliatic thiocyanates "but possess the c-istinct advantage over such suhstances in their toxicity, Colenan and Semba (12), assignors to the Dow Chemical Compar^'-, in United States patent 2,194,924, iss^ied March 26, 1940, applied for July 2, 1953, claim a substantially water-free insecticidal spray comprising a noncorrosive organic solvent laaving dissolved therein a toxicant selected from the class consisting of the extracts of pyrethrin- and rotenone-bearing plants, and as an added toxicant a conpound selected from the group consist- ing of the "beta-hydr ox;'- ethyl ethers of 2,4-diethyl phenol and 4-secondary- "butyl phenol. Hydroxy-all<:j'-l ethers may be mixed v/ith rotenone and the toxicant mixture dissolved in a jjetroleum distillate to obtain a spray composition of increased effect ivenesG, the hydroxy-allcyl ether both increasing the effectiveness of tho composition and serving as a muturJ solvent for the rotenone and petrolo\un distillate,, thereby obviating the use of a co-solvent, such as carbon teti'achloride, in the composition, 1-he proportions of hjrdroxy- alkyl ether compounds and of the plant extract can be v/idely varied, to pro- duce compositions effective for insect control. Various solvents may be employed as a carrier for the toxicants in the above-described compositions, depending uiDon the use for which the com- positions are intended. Por exanple, if an indoor spray is desired, a readily volatile solvent is most suitable. Por outdoor v;orlc, e. g. , in the spraj"- ing of cattle, where it is desirable that the spray residue be retained for a considerable period of time, a heavier and lesr volatile oil may be employed. In case the hydroxy-al^c^'l ether lias a limited solubility in a preferred sol- vent such as kerosene or naphtha, a mixture of such petroleum distillate vdth, for example, methyl-ethyl ketone, or carbon tetrachloride ma;;'' be employed. Other noncorrosive organic solvents such as benzene, eth;>'-lene dichloride, hydro^enatod naphthalene, butyl alcohol, and the like may be used to dissolve the hydroxy-alkyl ether or mixtures thereof with plant extracts, provided only tlia.t such solvent be inert viith respect to the toxicants employed and : aoninjuriouo to hi^mans, T'ests on houseflies by the Peet-G-rady method are recorded. A 0.1-percent solution of rotenone (a". P. 163° C.) v;as prepared by dissolving 0.1 Qvoja of rotenone in 12.5 grams of carbon tetrachloride and diluting to 100 milliliters v;ith the usual petroleum distillate, the carbon tetrachloride being employed as a mutual solvent to hold tho rotenone in solution. This solution vra,s employed as a base solution from which to prepare tost compositions containing 0.075, 0.05, 0.035, and 0.01 percent of rotenone. Other test solutions v;ero prepared in which the hydroxy-alkyl ethers were erai^loyed as a rnutiial solvent for both rotenone and potrolemi distillate, the hydroxy-allQ''l ethers serving both as toxicants and as solubilizing agents. Such solutions v;ore prepared by first dissolving the desired amount of rotenone in the hydroxj.^-alkyl ether and thereafter adding the petroleum distillate to the mixture. As the mojv tality of flies sprayed v;ith rotenone solutions did not reach a constant « 25 - Value for a period of approximahel;- IP. hourr? follov/ing the sprri^ing opera- tion, all flies sprayed irx this aerion of errperiilitintn v;erD examined at 24-, 48-, and 72^1iour periods to debermiiie the mortality resulting from sUch treatment. The folloT-ring results are representative of those ohtaincd v;ith compositions containing lietv;oen 0.01 and 0.075 percent of rotonojic and from 1 to 3 percent of the hydro;<:3'--'alkyl ethers: Material and concentration 0,01 percent rotenone 0,025 percent rotenone 0,05 percent rotenone 0,075 percent rotenone 3 percent of "beta-hydroxy-ethyl ether of 4-t>ortiary-'butyl-phenol 2 percent of he ta-hydroxy~e th.vl ether of 4-secondary-.hut7l«phenol 0.025 percent rotenone -f 3 percent of heta-hydroxj^-ethyl ether of 4- tertiary-hutyl-phenol 0,05 percent rotenone -f 3 percent of heta-hydroxy-ethyl ether of 4-tertiary-hutyl-phenol 0,075 percent rotenone + 3 i^ercent of "beta-hydrox^r-ethyl ether of 4-tertiary-"butyl-phenol 0,05 percent rotenone -i- 2 percent of l)eta-li3'"droxj'"-ethyl ether of 4-secondary^'butyl-phenol Average Moan mortality, in- ■nockdown in 24 48 72 10 minutes hours hours hours Percent • ? e r c e n t 75 7 18 25 76 8.G '25.2 37.5 83 . 11 42.3 59,4 89 41 73.2 94 34 52 54 77 28 51 33 93 97 99 25 34 74 79. 88, 72,5 92.2 33 74 ■ Tests were made to determine the stahilising effect exerted "by hy droxy-allryl ethers upon solutions containing rotenone. Material and concentration 0,1 percent rotenone Ditto 0.1 percent rotenone 4 3 per- cent of heta-hydroxy-ethyl ether of 4-tcrtiary-hutyl- phenol 0,1 percent rotenone -h 3 per- cent of heta-hydroxy-ethyl ether of 4— tertiary- Dutyl- phenol llumher Average Mean mortality in- of days kiiockdov/n 24 48 72 e:cposure in hours hoiirs hours to lifjht 10 minutes Percent Percent 92 15.5 48.3 75,5 12 42 5 8 11.3 12 98 95 35,3 38,3 99.3 84,3 93 , - 26 - Other hydroxj*'-alkyl ethers of allc^d-pHenols may be used in the compo- sitions descrlljed in tha foregoing examples, e.g., ■beta-hydroxj^-ethj'-l ether of 4-normal-'butyl -phenol J bsta-hydi-oxy- ethyl ether of 4-iso"butyl«phenol; "beta- hydroxy-ethyl ether of 4-norTiial-anyl -phenol; beta-*ydroxy-ethyl ether of 2- ethj'l-4-.tertiarj'-aiayl phonol; "beta-hydroxy- ethyl ether of 2.4-di-isopropyl- phenol; Tjeta-hydroxy- ethyl ether of di-isopropyl-phenol; "beta-hydroxj'-ethyl etlier of 2-ethyl-4-isopropyl-phenol; "beta-hj'droxy- ethyl ether of 4-normal- hexyl««amylphenol 5 percent dibutyl^^hthalate, 2 percent of 20:1 derris extract (containing rotenone,.. deguelin and tephrosin) and, 90,5 percent insecticide naphtha, when tested by the P©et-»Omdy method, caused a knockdovm of 98 percent in 10 min- utes, a kill of 70 percent in 24 hours, and 72 percent killed and moribixnd in 72 hours, Hockenyos i2Zy, assignor to Monsanto Chemical Cnnpany, "'In . ' - United" States patent 2,197,500, issued April l£^}9aD., applied for May 7, 1934, claims a dry loaecticidxl composition which is readily dispersible in water to form a stable dispersion, comprising an organic insecticide of the rotenone ■aJidpyretlarum. class, and a water-eoluble salt of a hydroxy substituted aromatic sulphonlc acid which is soluble in acetone, said product being produced by diaaolving a mixture of the Insecticide and dispersing agent in acetone and evaporating aald -solution to dryness. For example, Are^co and an equal weight of derric or cube resin are dissolved in acetone. Certain mbter ant.ioxidrntr, are effective in overcor.ing the deterio- rative influence of light on rctenone. Exrimpleg are phen7l~ljeta-naphthylamine^ phenyl-alphn.-naphthylainine, and the homolof^u.es thereof. Tests upon aphids with derris resin at from 1:4,000 to 1:0,000 v;ith the addition of Aresco, phenyl-heta-naphth^lanine, phonj-l-Tjeta-naphthylamine plus lanphlack, oleic acid, and oleic acid plus Ifunphlack, are recorded, from v/hich it is concluded that Aresco has a distinct inscosBicidal value even when u.sed in very dilute solutions; that Aresco has a preservative effect on the active principle and may he employed advantaj.'^cously with the phenolic amine preservatives; and that the addition of lamp "black has a favorable effect in combination with the preservatives. Knight (27), assignor to Shell Development Company, in United States patent 2,190,173, issued February 13, 1240, allied for Js.nuary 18, 1937, claims the method of increasing the effectiveness in tree sprpy oils of oil- soluble toxics of the class consisting of nicotine and rotenone, which method comprises incoiinoi-ating said toxics in a mineral oil of about 40 to 100 seconds Sayboldt viscosity at 100*^ F. , adding to said oil about 1 percent to 5 ]percent of an emulsifior comprising an liydroxy ester of a Iiigh molecular v;eight organic acid (e.g., glycol mono-oleate, glycero-moho-oleate or glycero- di-oleate), emulsifying said nil in water in the presence of a small amount of bentonite whereby oil clusters are formed in the water, and spraying said emulsion on trees, Bentonite insures a satisfa,ctory emulsion and oil deposit v.'hon added toxic materials, such as cryolite, lead arsoncite, nicotine, rotenone, or other toxic materials, are incorjporated in the emulsion. Such added ma- terials may markedly interfere vdth proper emulsif ication and oil deposit in the absence of a conditioner. However, the bentonite composition insures proper em\ilsification and protects against inversion, and by causing the substantially coinplete deposit of oil it mcJces oil-soluble toxics such as rotenone and nicotine even more effective. Neu (34), assignor to Deutsche Ilydrierwerke A.-G-., in United States patent 2,194,446, isstied March 19, 1940, applied for June 25, 1936, in G-eiinany June 26, 1935, clan.ms a iDest-destroying a.queous emulsion consisting of a poison of the group consisting of rotenone, di~hydro-rotenone, pyre- thrins, pyrethrum and derris-root extracts; cyclo-hexanone; hydrcgenatad naphthalene; with kerosene as a solvent; a fatty alcohol sulfonate having eight to ten carbon atoms in the molecule as an emulsifying agent, and water, the cyclo-hexanone and hydrogenated naphthalene being present in substantial proportions and sufficient to produce a clear and lasting ao?-ution. In p].ace of cj'clohexanone other cyclic ketones con be used, e.g., cyclopentanone, methji^lcyclohexanone, beta-dekalinone. Of the hydrogenated products of naphthalene the tetrahydronaphthalene and the dekah.ydrona^ohtlaaleno have proved particularly suitable Acetone, chloroform, and benzine are mentioned as known solvents for rotenone. - 28 - The follov;ing are examples: In dissolving 0.5 grajn of a lOC-pei-cent rotonone (163° C.) in 10 cc. of cycloliexanone ("bearing 35 percent of ketone) and in adding 90 cc. of kerosene or a mixture of 10 cc. of tetra-hj'-dro- ?jnd 10 of deka-hydro-naphthalene, the rotenone v/ill cr-stallize out after some tine, "but "b:/ the adr'.ition of a solution of 0.5 gram of rotenone in 10 cc, of cj-clohexanone (85 percent), 10 cc» of tetrahydronaphthalene, 20 cc. of cleka- -. bj'dro-naphthalene, and 60-80 cc. of kerosene, one obtains a liquid which also after a long standing remains clear and which is very suitable for couhating flies and gnats. Also, in dissolving 0,5 gram of rotenone in 10 cc, of cyclohexanone (85 percent; and 10 cc, of dcka-liydro -naphthalene and in adding 50 grams of an aqueous 30-percent solution of the sodium salts of the sulfuric acid esters of fatty alcohols with 8-10 C-atoms, one obtains a lasting, clear, and transpar.^nt solvition v;hich, v;hen diluted with vrater, is particularly fit for combating gadfly grubs with pasture animals. The dilution made v/ith water, and viherein the rotenone is finely suspended, has a milky- turbid aspect and it scarcely precipitates. This diluted solution is also an excellent means to conibat the horticulture-damaging pests and doesnH do any ham to the plants, Dihjrdrorotenone, derris extracts, pyrethrins, and pyrethrum extracts cr-n be dissolved in quite the same v;ay as rotenone, v/hen the above prescrip- tions are followod. • 29 - Patenbs Gitud 1. ADAiMS, J. P., and NIZITIK, A. A. 1939. Stable parasiticide. U. S. Patent 3,172,314; issuod Sept--:;i"ber 5, 1939; applied for October 28, 1935; as^if^ned to ':!. C. O^.Kane and P. Iloore, as trustees for Vie Crop Protection Institute. 2» BLOUIIT, A, L. ■ 1938. Insecticide, U. S. Patent 2,132,013; issued October 4, 1933; applied for July 2, 1934; assigned to Union Oil Ccnipon^- of California. 3. BOCBIUHL, M., and GOHR, 'G, 1939. Schadlingshek"jyiipflm«;smittel, Geruio.n Patent 674,408; issued April 17, 1939; applied for i-b.rch 9,. 1934; assi.'^iried to I, &, Farboiiindusirio A,-G, and GOER, 1939. Schadlingsbekanipfungsmittol. German Patent 675,220; issued May 3, 1939; applied for March 25, 1934; assit^ncd to I. G. larbenindustrie A.-G. (addition to 674,483). 5. BOUSqOET, E. 17. 1939, Insecticide. U. S. Patent 2,153,119; issued July 18, 1939; applied for October 3, 1933; assi^-ned to E. I, du Pont de llemotirs & Company-. and SALZ.3EI-:G, P. L. 1939, Insecticidal compositions containing heterocyclic ajnides, U, S. Patent 2,16'3,118; issued July 18, 1939; apijlied for October 3, 1936; assigned to £. I. du Pont do Hemours & Company, 7, BCYCS, ALP5ED l-I. 1940, Dustnng composition. U. S. Patent 2,191,421; issued Pebruary 20, 1940; applied for Dece;nber 2, 1937; assigned to the Government and the People of the United States of America. 8. BHUBAKEP. M. M. 1937, Protection of materials subject to parasitic ••^ttrcl:. U. S, Patent 2,098,942; issued ITovtmbcr 15, 1937; applied for June 17, 1936; in German:'- Jirne 18, 1935; assigned to- E. I. du Pont de Nemours & Compan;,'". - 30 - 9. CAESV.'ELL, T. S. 1940. Insecticide. U. S. Patent 2 ,192,394; issued March 12, 1940; applied for November 2o, 1936; assigned to Monsanto Chem- ical Company. 10, CHRISTI4AN1T, L. J. , and JMIS, 33. >/. , Jr. 1939. Stabilized rotenone compositions. U. S. Patent 2,151,651; ; issued March 21, 1959; applied for November 18, 1932; assigned to American Cyanamid Company. 11. C0L3MAN, G. H. , and ZEMEA, J. W. 1938. Household spray. U. S, Patent 2,133,972; issued October 25, 1938; applied August 10, 1937; assigned to the Dow Chemical Company, 12, and ZEtSA, J. W, 1940. Spray composition. U. S. Patent 2,194,924; issued March 26, 1940; applied for July 2, 1938; assigned to Dov; Chemical Company. 13. I'ALOON, D. B, 1939, Oxidation inhibitor for insecticides. U. S. Patent 2,144,366; issued Janua.ry 17, 1939; applied for October 24, 1933; assigned to Hammond Paint w Clieraical Company, Inc. 14. -^— — --f;,. 1939. Oxidation inhibitor for insecticides. U. S. Patent 2,144,367; issued Janua.ry 17, 1959; applied for October 24, 1953; assigned to Hajnmond Paint and Chemical Company, Inc.; divided and this application May 14, 1938. 15. 16, 17. 1939. Oxidation inhibitor for insecticides. U. S. Patent 2,144,368 issued January 17, 1939; applied for May 14, 1938; assigned to Hojomond Paint and Chemical Co., Inc, 1939. Oxidation iniiibitor for insecticides. U. S. Patent 2,144,369; issued January 17, 1939; applied for May 14, 1938; assigned to Hsxraond Paint and Chemical Co., Inc. . 1939. Insecticide, U. S. Patent 2,168,064; issued August 1, 1939; applied for June 11, 1935; assigned to Hammond Paint and Chemical Company, Inc, - 31 - 18, GOLDSGHMIDT, S., and MARTIN, K, 1937, ImproveMents in or relating to toxic agents, more particularly insecticides. British Patent 4-71,153; issued August 26, 1937; applied for ?ebruarj;- 26, 1836. 19. GOODHUE, L, D, 1938, Adhesive for insecticides and a process for raalcing soine. U.S. Patent 2,129,517; issued Septca'ber 6, 193C; applied for January 10, 1933; dedicated to free use of the People of the United States of America, 20, 1939. Adhesive for insecticides. U. S. Patent 2,146,258; issued February 7, 1939; applied Septomber 26, 1938; dedicated to the free use of the People of the United States of Aaorica, 21. — 1939, Aai\6sive for insecticides, U. S, Patent 2,146,257; issued Pehruary 7, 1939; applied for Septcmher 23, 1938; dedicated to the free use of the People of the United States of Amorico.. 22, HILL, M, L., and PEHGUSON, B., Jr. 1940, Insecticide, U; S. Patent 2,192,347; issued March 5, 1940; applied for February 1, 1937; assigned to Gulf Oil Cor- poration, 23. HOCIffiNYOS, G. L, 1940, Insecticidal com-oosition and method of preparing the sajne, U. S. Patent 2^,197,500; issued April 16, 1940; applied for May 7, 1934; assigned to Monsanto Chemical Company, 24, I. G. PAEBMIITDUSTHIE AETCBNGESELLSCI^APT 1938, Improvements relating to insecticides. British patent 493,764; issued October 10, 1938; a^^plied for April 9, 1937, in Germany April 11, 1935. 25. Il-PEEIAL CHEMICAL linDUSTRIES LIMITED 1938, Verfahren 2ur Gev/innung von Ho tenon und ihm verv;andten Insekticidcn, German Patent 665,076; issued September 16, 1938; applied for October 29, 1935; in Great Britain October 29, 1934. - 32 - 26. KILGORE, L. B. 1939. Selective extraction of rotenone by certain esters. U, S, Patent 2,149,917; issued March 7, 1939; applied for April 24, 1936; assigned to Kilgore Development Corporation. 27. KNIGHT, H. 1940. Oil tree spray. U. S. Patent 2,190,173; issued lebruary 13, 1940; applied for January 18, 1937; assigned to Shell Development Company. 28. LIND, T. 1939, Insecticide. U, S. Patent 2,173,849; issued September 26, 1939; applied for September 4, 1937; assigned to Lin-Tox Corporation. 29. LUNEVALE PRODUCTS LIMITED and FitzGIBBON, M. 1938, Improvements in or relating to the manufacture of complex nicotine products and of insecticidal and fungicidal preparations comprising the same. British Patent 492,660; issued September 20, 1938; applied for March 20, 1937. 30. MARIICO, S. E. 1939. Insecticide and process of making the same, U. S, Patent 2,158,241; issued May 16, 1939; applied for June 18, 1936, 31. McCOMELL, H. K. 1937. Fumigating package. U. S, Patent 2,071,171; issued February 16, 1937; applied for June 15, 1935; assigned to Tobacco By-Products and Chemical Corporation. 32. NAAiViLOOZE VENNOOTSCHAP CHEMISCHE FABRIEK SERVO and ROZEi^IBROEK , M. D. 1939, Improvements in or relating to preparations for combating plant diseases. British Patent 501,601; issued February 27, 1939; applied for August 26, 1937; in Holland August 26, 1936. 33. KEU, R. 1938. Verfahren zur Herstellung von zur Insektenbek&npfung geeif.neten L'dsungen des Rotenons, seiner Abkttmmlinge, der Pyrethrine, der Pyrethrum- oder Derriswurzelextrakte. German Patent 665,216; issued September 20, 1938; applied for June 27, 1935; assigned to Deutsche Hydrierwerke A,-G. 34. NEU, R. 1940. 33 Pest destroying onnilsion. U. S. Patent 2,194,^46; issued March 19, 1940; applied for June 26, 1936; in Germany June 26, 1935; assigned to Deutsche Hydriervrerke A.-G, 35. O'KANE, W. C. 1938. Active insecticide and fungicide. U. S. Patent 2,127,526; issued August 23, 1938; applied for August 16, 1934. 36. PERUVIAN MINISTRY OF EOMEKTO 1938. Vermifuges and insecticides. Patent of Invention No. 986, Off. Communication No. 28, February 1, 1938. 37. RIPPER, W. E. 1939. Poison for destroyiag insects, animals and the like. Brit- ish Patent 505,863; issued May 18, 1939; applied for November 18, 1937; in Austria November 20, 1936, and April 20, 1937. 38. SALIARIS, M. C. 1938. Perfectionnements a la preparation des produits insecticides et parasiticides. French Patent 829,338; issued June 20, 1938; applied for February 18, 1937. 39. 1938. Perfectionnements a la preparation des produits ins#cticides et parasiticides en suspension ou en emulsion. French Patent 829,339; issued June 20, 1938; applied for February 18, 1957. 40. SCHOTTE, H. , and GORi^TZ, K. 1938, Insecticide and method of making same. U. S. Patent 2,136,863; issued November 15, 1938; applied for December 12, 1933; in Germany June 30, 1932; assigned to Schering- Kahlbaura A.-G. • 41, 1939. Raupenbekampfungsraittel. German Patent No, 671,162; issued February 1, 1939; applied for November 14, 1931; assigned to Schering A.-G., Berlin - 34 - 42. SIBLEY, R. L. 1938. Insecticidal composition. U. S. Patent 2,138,516; issued iJovenber 29, 1938; applied Octo"ber 16, 1936; assigned to Monsanto Chemical Company, 43.. THOMPSON, F. M. ' 1939. Insecticide. U. S. Patent 2,160,579; applied for April 28, 1937; issued Jiay 30, 1939; assigned to Hercules Pov/der Company, 44. WILSOiJ, R. E. 1938. Stabilized white oil. U. S. Patent 2,123,457; issued July 12, 1938; applied for January 16, 1931; renewed December 6, 1937; assigned to Standard Oil Company of • Indiana, 45. WOTHERSPOOK, R, 1938, Process for preparing improved derris and cube extracts and hydrogenated derivatives and products produced thereby, U. S. Patent 2,126,854; issued August 16, 1938; applied for April 28, 1934; assigned to Derris, Inc. Junior Patentees Index Ferguson, B. , Jr.; see Hill, ii. L, FitzGibbon, M, ; see Lunevale Products Limited Gornitz, K. ; see Schotte, H. Gorr, G. ; see Bockmuhl, M. Jayne, D. W. , Jr.; see Chri stmann, L. J. Martin, K. ; see Goldschiaidt, S, Nikitin, A, A.; see Adams, J. F, Rosenbroek, M, D, ; see Naamlooze Vennootschap Chemische Fabriek Servo Salzberg, P, L. ; see Bousquet, S. \v, Zemba, J. V/, ; see Coleman, G. H. Assifjnee Index American Cyanamid Company; see Christmann, L. J., and Jayne, D. W. , Jr. Derris, Inc.; see Wotherspoon, R, Deutsche Hydrierwerke A,-G, ; see Neu , H. Dow Chemical Company; see Coleman, G. H. , and Zemba, J. \K E. I. du Pont de Nemours and Company; see Bousquet, E. W.; Bousquet, g. w. • and Salzberg, P. L. ; and Brubaker, w. M. Government and People of the United States of America; see Boyce, A. M, Gulf Oil Corporation; see Hill, M. L., and Ferguson, B., Jr. Hammond Paint and Chemical Compaiiy, Inc. ; see Faloon, D. B, Hercules Powder Company; see Thompson, F. h. I. G. Farbenindustrie A.-G.; see Bockmuhl, M. , and Gorr, G. - 35 - Kilgore Development Corporation; see Kil^ore, ,L. B. Lin-Tox Corporation; see Lind, T. Monsanto Chemical Company; see Carswell, ll, S. ; Hockenyos, G. L. ; and Sibley, R. L. O'Kane, W. C.i and Moore, P.; see Adams, J. T. , and Nikitin, A. A. People of the United States of America; see Goodhue, L. D. Schering-Kahlbaura A.-G. Berlin; see Schotte, E. , and Gornitz, K. Shell Development Company; see Knight, H. Standard Oil Company of Indiana; see v^ilson, R. S, Tobacco By-Products and Chemical Corporation; see McConnell, K. K. Union Oil Company of California; see Blount, A. L. Insecticidal Ingredients, Diluents, Solvents, Stabilizers, etc.. Used with Rotenone Products Acetalacetone oxalate n- butyl ester, U^ S. 2,149,917 Acetaldehyde diaryl arylene diamine product, U. S. 2,138,516 Acetate of deacetylated chitin,^ U. S. 2,098,942 Acetone, French 829,338; U. S. 2,126,854; 2,144,366; 2,151,651; 2,173,849; 2,194,446; 2,197,500 Acetone-furfural product, U. S. 2,U-6,258 Acetophenone- furfural product, U, S. 2,146,258 Additive ebher, U. S. 2,160,579 Alcohol, Ger. 674,488; U. S. 2,144,366; 2,144,367 Alcohol, polyhydric, ester of, Ger, 67^,488 Alcohol-diaryl arylene diamine products, U. S. 2,138,516 Alcohol, sulphated, sodium salt, Ger. 065,216 Aldehyde-diaryl arylene diamine products, U, S, 2, 138,d16 Alumina, U. S. 2,136,868 Alumina gel,, French 829,338 Amino-carboxy compounds, U. S. 2,151,651 Ammonia, U. S. 2,129,517 Ammoni\ira caseinate, U, S, 2,129,517 Amyl alcohol-aldehyde-diaryl arylene diamine product, U. S. 2,138,516 Amyl alcohol-terpene ether, U. S. 2,160,579 Aniline, U. S. 2,144,366 Aniline , dichloro,' U. S. 2,151,651 Aniline, 2, 5-dichloro, U. S. 2,151,651 Aniline ethylchloro, U. S. 2,151,651 Aniline-furfural product, U. S. 2,146,257 ..■Aniline methylchloro, U. S. 2,151,651 Anthracene, crude, U. S. 2,136,368 Anthranilic acid, U. S. , 2,151,651 Anthranilic acid, chloro, U. S. 2,151,651 Anthranilic acid, dichloro, U. S. 2,151,651 Antimony oxide, U. S. 2,158,064 Apricot pit flour, U. S, 2,191,421 Aresco, U. S. 2,197,500 Arsenic compounds U. S. 2,136,868 Arsenobenzol, U. S. 2,132,013 Arsine oxide, dimethylphenyl, U. S." 2, 132,013 - 36 - Arsine oxides, U. S. ??^ 132^013 Arsine, ppraethoxyphenyl, U. S. 2,132,013 Arsines, U. S. 2,132,013 BsriTim sulphate, U. S. .2, 163,064 Bari\im titanox, U. S. 2,168,054 Bentonite, U. S. 2,'190,173 Benzene, Ger. 674,488; U. S. 2,194,446; 3,194,924 Benzidine, U. S. 2,144,366; 2,1^4,369 Benzidine, di-o-biphenyl, U. S. 2,138,516 Benzidine, di-p-biphenyl, U. S. 2,138,516 Benzidine, diphenyl, U. S. '2,138,516 Benzidine ditolyl, U. S. 2,138,516 Benzidine, dixylyl, U. S. 2,138,516 Benzol, U. S. 2,125,854 Benzophenone, furfural product, U. S. 2,146,258 Benzyl alcohol-aldehyde-diaryl arylene diamine product, U, S. 2,138,516 Birch flour, U. S. 2,19i;42i Bismuthines, U. S. 2,152,013 Bole, U. S. 2,136,868 Borax, U. S. 2,136,863 Boric acid ester, sulphonated, Brit. 501,801 Borneol ethers, U. S. 2,160,579 Bornylene additive ether, U. S. 2,160,579 Brazil nut shell flour, U. S. :-:^ 191, 421 Butyl alcohol, U. S. 2,19'±,924 Butyl alcohol-aldehyde-diaryl arylene diamine product, U. S. 2,138,516 Butyl alcohol-terpene ether, U. S. 2,160,579 m-Butyralacetone oxalate ethyl ester, U. S. 2,1'±9,917 Butyraldehyde diaryl arylene diamine product, U. S. 2,138,516 Calcium caseinate, U. S. 2,132,013 Calcium titanox, U. S. 2,168,06i Camphan, oxyphenyl, ethoxylated, G-er. 674,488 Caraphene additive ether, U. S. 2,160,579 Camphor sassafrassy oil, U. S. 2,132,013 Carhazole, U. S. 2,136,868 Carhon tetrachloride, French 829, 338 ; Gar. 674,488; U. 3. 2,133,972; 2,1^4,366; 2,194,924 Carene additive ether, U. S. 2,160,579 Casein, Brit. 505,853 Castor oil, ethoxylated, Ger. 674,488; 675,220 Castor oil fatty acid glycol ester, sulphonated phosphoric acid ester of, Brit. 501,801 Castor oil, sulphonated, U. S. 2,127,526 Cedar bark flour, U. S. 2,191,421 Cedar wood flour, U. S. 2,191,421 Cellosolve, U. S. 2,132,013 Cellulose, Brit. 505,853 Cherry pit flour, U. S. 2,191,421 China clay, U. S. 2,136,868 Chitin, deacetylpted, acetate Chloroform, French 829,338; U. S. 2,126,854; 2, 19-1, -^.46 Chloroform liniment, U. S. 2, ! of. U. S. 2,098 .942 r. S. 2. 126, ,854; 2,194 158, 241 - 3^ - Clay, U. S. 2,172,314 Coconut shell flour, U. S. 2,101,421 Copper compounds, U. i. 2,136,868 Copper-nicotine coraplex,, Brit. 492,560 Copper sulphate, U. S. 2,158,241; £.172,314 Corn oil, U. S. 2,127,526 Creosote wood, U. S. 2,123,457 Cresol, U. S. 2,14^,366 Cresylic acid, U. S. 2,123,^57 Cyclohexonol-aldehyde-diaryl arylene diamine product, U. S. 2,138,516 Cyclohexanone, Ger. 665,216; U. S. 2,194,446 Cyclopentanone, Ger. 665,216; U. S. 2,194,446 Dekahydronaphthalene, U. S. 2,194,446 beta-Dekalinone, U. S. 2,194,4^6 Derris oil, U. S. "2,126,854 Dextrin, U. S. 2,123,457 Diamines, disryl arylene, U. S. 2,138,516 Diazoamino corapomid, Brit, 493,764 Di-beta-naphthylamine, U. S. 2,144,366; 2,144,363 Diethylene glycol, rconoethyl ether, U. S. 2,132,013 Diethylene glycol monoethyl ether-terpene ether, U, S, 2,160,579 Diethylene glycol terpene cthjr, U. S. 2,160,579 Dihydrorotenone, Gor. 665,216; U. S. 2,194,446 Dioxaii, Ger, 674,488 Dipcntene additire ether, U. S. 2,160,579 Diphanylamine, U. S. 2,144,366; 2,144,369 Ester of a polyhjdric alcohol, Gor, 674,488 iBter^ enilpjionated, Brit. 501,801 Esters, unsaturated diketo carhoxylic, U. S» 2,149,917 Ether, Preuch 829,338; Ger. 674,488 Ethyl acetate, U. S. 2,126,854 Ethyl eJvcchol-aldohyde-diaryl arylene diamine product, U. S. 2,138,516 Ethyl alcohol-terrjone ether, U. 3. 2,160,579 Ethyl-3-n.etl.yl-3-Leptene-2-:i'-oxalate, U. S. 2,149,917 Ethylene dichloride^ U. S. 2,126,854; 2,144,366; 2,144,367; 2,194,924 Ethylene- glycol raonohutyl ether-terpcne ether, U. S. 2,160,579 Ethylene glycol monrjethyl ether terpone ether, U, s. 2,160,579 Ethylene glycol-tcrpcne ether, U. S. 2,160,579 Ethylene glycol- turpentine ether, U. S. 2,160,579 Eugen^l, U. S. 2, 144, 366 ' Eendhyl alcohol-ether, U. S. 2,160,579 Jornuadahyde, U. S. 2,123,457 E^rmaldehyde-diaryl arylene diamine product, U. S. 2,138,516 I\irfural-amine products, U. S. 2,146,257 l^arfuraL-ketorte. products, U, S. 2,1^6,258 Gasoline, U. G. 2,l-i^,366 Glue, U. S. 2, 123, '457 Glycwro-di-cleate, J. S. 2,190,173 Glycoro-mono-oleate, U. S. 2,190,173 Glycerol-te.rpeue ether, U. S. 2,1^^0,579 ' GlyooX-sionomfithj^l ether, Ger, 674,488 - 38 - Glycol mono-oleate, U. S, 2,190,173 Green soap, U. S. 2,158,24:1 Guaiacol, U. S. 2,144,366 Gun ghatti, U. S. 2,123,^57 Gum tragacanth, U. S. 2,125,457 Gypsum, calcined, U. S. 2,168,064 Heptaldehyde diaryl arylene diamine product, U, S. 2,138,516 Hexahydroxylol, Ger. 665,216 Ee.xamethylene tetramine, U. S. 2,144,366; 2,144,369 Hydrocarbon distillate, U. S, 2,127,526 Hydrocarbons, alicyclic, U. S, 2,136,868 Hydrocarbons, aliohatic, U. S. 2,136,868 Hydrocarbons, cyclic, U. S. 2,136,868 Hydrocarbons, hydrogenated arouatic, Ger, 565, 216'" Hydrocarbons, petroleum, U. S. 2,126,854 nydroquinone, U. S. 2,132,013; 2,144,566 Hydroxy-amino compoujids, U. S, 2,151j651 Kydroxy-carboxy compounds, U, S. 2,151,651 Hydroxy ethyl ether"i U, S. 2,133,972 Isothiocyanate, aromatic, Brit. 471,153 IsothjTiiol, U. S. 2,136,868 Kaolin, U. S. 2,168,064 Kerosene, U. S. 2,144,366; 2,149,917; 2,194,446; 2,194,924 Ketones, cyclic, Ger. 665,216 Lampblack, U. S. 2,197,500 Laxiryl trimethylanmonium chloride, French 829,339 Lecithin, U. S. 2,132,013 Li^ht oil, G-or. 6o:'i,266 Lignocol, U. S. 2,1-4,366 Lime-soap, U. S. r:,l.?5,868 Linseed oil-potash soap, U. S, 2,173,849 Lithopone-zinc sulphide, U. S, 2,168,064 Lithopones, titanated, U, S. 2,168,064 Mesityl oxide oxalate cyclohexyl ester, U. S. 2,149,917 Mesityl oxide oxalate etlij^ ester, U. S. 2,149,917 Mesityl oxide oxalate isobutyl ester, U. S, 2,149,917 Mesityl oxide oxalate n-butyl ester, U. S. 2,149,917 Mesityl oxide oxalate sec.-amyl ester, U. S. 2,149,917 Mesityl oxide oxalate tetrahydrofurfuryl ester, U. S. 2,149,917 Methyl alcohol-aldchyde-diaryl arylene diamine product, U. S. 2,138,516 Methyl alcohol-terpene ether, U. S. 2,160,579 Methyl cyclohexanone, Ger. 665,216; U. S. 2,194,446 Methyl ethyl ketone, U. S. 2,194,924 3-kethyl-3-heptene-2-one-oxalate ethyl ester, U. S. 2,149,917 3-wethyl-3-pentene-2-one-oxalate ethyl ester, U. S. 2,149,917 t;ethylothylkotone- furfural product, U. S, 2,146,258 Mineral oil, U. S. 2,190,173 Mineral spirits, U. S. 2,144,566 Morpholene, parahydroxyphenyl, U. S. 2,132,013 Morpholino, 4-(l0, 11-undecylenoyl) , U. S. 2,166,118 Naphtha, U. S. 2,199,924 - 39 ilaphthn, insecticide, U. S. 2,192,347 Faphthalene, U. S. 2,136,868 Naphthalene, decahydro,' Gar. 665,216 Naphthalene, hydrogenated, U. S. 2,194,446; 2,194,924 Naphthalene, tetrahydro, 'Ger. 665,216 Naphthol, U. S. 2,136,868 Naphthol, 1,2-ariiino', U. S. 2,123,457 alpha-Naphthol, U. S. 2,144,36G; 2,144,367 beta-Naphthol, U. S. 2,144,366; 2,144,367' Uaphthylpmine, U. S. 2,144,368 alphs-Naphthylanine, phenyl, U. S. 2,144,366; 2,144,368 "beta-Kaphthylamine-furfural product, U. S. 2,146,257 2-Iaphthy]ke tone- furfural product, U. S. 2,146,258 Nicotine, U. S. 2,158,241; 2,173,849 Nicotine-copper complex, Brit. 493,660 Nopinene additive ether, U. S. 2,160,579 Oil, glyceride, U. S. 2,127,526 Oil, white, U." S.' 2,123,457 Oils, Ger. 674,488 Oils, animal, sulphonated, U. S. 2,127,526 Oils, petroleum, U. S. 2,123,457 Oils, vegetable, sulphonated, U. S. 2,127,526 Oleic acid, U. S. 2,151,651; 2,197,500 Oleyl alcohol, ethoxylated, Ger. 674,488; 675,220 Oleyl chloride-di ethyl diaminoethane product, French 829,339 Olive pit flour, U. S. 2,191,421 Organic acid, U. S. 2,190,173 Peach pit flour, U. S. 2,191,421 Pecan shell flour, U. S. 2,191,421 Petrolatum, white, U. S. 2,126,854 Petroleum, Ger. 674,488 Petroleum distillate, Ger. 665,216; U. S. 2,133,9.72 Petroleum oil, U. S. 2,144,365 Phellandrene additive ether, U. S. 2,160,579 Phenanthrene octohydro, Ger. 665,216 Phenol, U. S. 2,144,366 Phenol, alkyl-amino, U. S. 2,123,457 Phenol, 2-cyclohexyl, "beta hydroxyethylether, U. S. 2,133,972 Phenol, dibenzyl paraajnino, U. S. 2,132,013 Phenol dibutyla^ino, U. S. 2,123,457 Phenol, 2,4-diethyl, beta-hydroxyethyl ether, U. S. 2,194,924 Phenol, 2,4-diethyl, hydroxy-butyl ether, U. S. 2,194,924 Phenol, 2,4-diethyl, hydroxy-propyl ether, U. S. 2,194,924 Phenol, di-isopropyl, betr-hydroxyeth^'l ether, U. S. 2,194,924 Phenol, 2,4-di-isopropyl, beta-hydroxyethyl ether, U. S. 2,194,924 Phenol, dodecyl, ethoxylated, Ger. 674,488; 675,220 Phenol, 2-ethyl-4-isopropyl, beta-hydroxyethyl ether, U. S. 2,194,924 Phenol, 2-ethyl-4-tertiary-arayl, beta-hydroxj'-ethyl ether, U. S. 2,194,924 Phenol, 4-heptyl, beta-hydroxyethyl ether, U. S. 2,194,924 Phenol, hydroxyalkly ether, U. S. 2,133,972 Phenol, 4-isobutyl, beta-hydroxyethyl ether, U. S. 2,194,924 Phenol, iso-octyl, ethoxylated, Ger. 674,448, 675,220 - 40 Phenol, 2-methyl-4-isopropyl, hydroxy-propyl ether,. U. S, 2,194,924 Phenol, monobenzylparasraino, U. S. 2,132,013 Phenol, 4-nonnal-iiiiiyl, 'oeta-hydroxj'ethyl ether, U. S. 2,194,924 Phenol, 4-nonnal-butyl, "beta-hydroxyethyl ether, U. S. 2,19^,924 Phenol, 4--normal-hexyl, beta-hydroxyethyl ether, U. S. 2,194,924 Phenol, ortho-amino, U. S. 2,123,457 Phenol, para-amino, U. S. 2,123,457; 2,144,366; 2,144,369 Phenol, para-benzylamino, U, S. 2,123,457 Phenol, para-methylamino, U. S. 2,123,457. Phenol, prraphenylamino, U, S. 2,132,013 Phenol, para-tertiary-amyl, U. S. 2,192,347 Phenol, 4-second8ry-butyl, beta-hydroxyethyl ether, U. S. 2,194,924 Phenol, 4-secondary-butyl, hydroxybutyl ether, U. S. 2,194,924 Phenol, 4- secondary-butyl, hydroxypropyl ether, U. S. 2,194,924 Phenol, 4- secondary- hexyl, beta-hydroxyethyl ether, U. S. 2,194,924 Phenol, 4-tertiary-butyl, betR-hydroxj-'ethyl ether, U. S. 2,133,972; 2,194,924 Phenol, 4-tertiary-butyl, hydroxj^alkyl ether, U. S. 2,133,972 Phenol, 4-tertiary-hexyl, beta-hydroxyethyl ether, U. S. 2,194,924 Phenol-camphan, oxy, ethoxylated, Ger. 675,220 Phenols, amino, U. S. 2,151,651 Phenols, nitro amino, U. S. 2,151,651 Phenols, polyh;y'droxy, U, S. 2,151,651 Phenyl alpha-naphthylainine, U. S, 2,144,368; 1 Phenyl beta-naphthylamine, U. S. 2,197,500 ra-Phenylenediamine, N-N'-dialphanaphthyl, U. S. m-Phenylenedi amine, H-I-I' - dibetanaphthyl, U. S, m-Phenylenediamine, N-iT'-di-biphenyl, U. S, 2,138,516 ra-Phenylenediamine, H-il'-diphenyl, U. S. 2,138,516 m-Phenylenediajnine, H-N'-ditolyl, U. S. 2,138,516 o-Phenylenediamine, IJ-H'-dialphanaphthyl, U. S. 2,138,516 o-Phenylenediamine, lI-N'-dibetanaphthyl, U. S. 2,138,516 o-PhenylenedipEiine, N-H'-di-biphenyl, U. S. 2,138,516 H-H'-diphenyl, U. S. 2,138,516 ',197,500 2,138,516 2,1 '8, 515 H-N»-ditolyl, U. S. 2,138,516 N-N'-dialphanaphthyl, U. S. 2,138,516 N-N'-dibetrJiaphthyl, U. S. 2,138,516 IJ-lT'-dibiphenyl, U. S. 2,138,516 S. 2,138,516 3. 2,138,516 o-Phenylenediamine o-Phenylenedianiine p-Phenylenedi amine p-Phenylenediamine p-Phenylenedi amine p-Phenylenedismine, N-lJ'diphenyl, U p-Phenylenediajaine, il-N'-ditolyl, U Phosphines, U. S. 2,132,013 Phosphobenzol, U. S. 2,132,013 Phosphoric acid ester, sulphonated, Brit. 501,801 Fhthalate, dibutyl, U. S. 2,192,347 Pine oil, U. S. 2,132,013; 2.158,241 Pine oil additive ether, U, S. 2,160,579 Pine oil foots, U. S. '2,129,517 glpha-Pinene additive ether, U, S. 2,160,579 Plum pit flour, U. S. 2,191,421 Polyamino compounds, U. S. 2,151,651 Polysaccharides, Brit. 505,853 rotassivLii oleo abietate, U. S. 2,127,526 Propyl alcohol-aldehyde-diaryl arylene diamine product, U. S. 2,138,516 - 41.- Propyl alcohol-terpene ether, U. S. 2,160,579 Proteins, Brit. 505,853 Pyrethrins, U. S. 2,158,241; 2,19^,4'i6 Pyrethrmi, U. S. 2,136,868, 2,144,366; 2,194,446 Pyridine, U. S. 2,132,013 Pyrogallol, U. S. 2,132,013; 2,144,366 Essorcinol, U. S. 2,144,366 Rosin residxie, U.- S. 2,129,517 Rotenone hydrazone, U. S. 2,132,013 Rotenone oxime, U. S. 2,132,013 Rotenone phenylhydrazone, U. S. 2,132,013 Sabadilla seed, Ger.: 671,162 Safrol, U. S. 2,126,854; 2,132,013 Salicylic acid, ,U. S. 2,151,651 Sapamine, French 829,539 Silica gel, French 829,338 Soap, U. S. 2,132,013 . . Soap solution, Erit. 505,853 Sodiuni acetate, U. S. 2,136,868 ■ ' Sodimi bisulphide, U. .S. 2,127,526 Sodiiojn nitrate.. U. S. .2,0.71,171 Sodium sulphate, U.. S.. 2,.136,868 Sodium zeolite,- U. .S. .2,172,314 Stibine, cyclopentylphenyl, U. S. 2,132,013 Stibine oxides, U. S. .2,132,013 Stibines, U. S.- 2, 132,013 Sulfonate, fatty alcohol, U. S. 2,194,446 Sulphonated oils, U. S. 2,144,366 Sulphonic acid, hydroxy substituted aromatic, U. S, 2,197,500 Sylvestrene additive ether, U. S. 2,160,579 Talc, U. S. 2,136,868. . Terpene ethers-, U.- S.. 2, .160, 579 Terpenes, U. S. 2, 136 ,868 Terpinene additive ether, U. S. 2,160,579 alpha-Terpineol, U. S. 2,132,013 alpha-Terpineol additive ether, U. S. 2,160,579 alpha-Terpineol ether, U. S. 2,160,579 beta-Terpineol additive, ether, U. S. 2,160,579 Terpinolene additive. ether, U. S. 2,160,579 Tetrahydroacetophenone oxalate ethyl ester, U. S. 2,149,917 Tetrahydronaphthalene, U. S. 2,194,4-6 ThjTnol, U. S. 2,136,868; 2,144,366 Titanium oxide, U. S, 2,168,034 Titanium oxide gel, French 829,338 Toluene, Ger. 674,488 . p-Tolui dine- furfural product, U. S. 2,146,257 Tributylemine, U. S.. 2,132,013 Triethanolamine oleate, U. S. 2,132,013 Triethanolamine stearate, U. S. 2,132,013 Triethylamine, U. S. 2,127,526 Turkey red oil, U. S. 2,136,868 - 42 - Turpentine, additive ether, U, S. ?, 160, 579 10,ll-Undec:'lenic acid, U. S. 2,166,119 Vanadines, U. S. 2,132,013 Vanoline, U. S. 2,132,013 Vegetable proteins, Brit. 505,853 Veratrine, Ger. 671,162 Walnut shell flour, U. S. 2,191,421 Zein, Brit. 505,853 ... Zinc oxide, U. S. 2,168,064 A List of All Patents Arrar^ged According to Filing Dates Filing date January 16, 1931 l^'oveinber K, 1931 lToveta"ber 18, 1932 October 24, 1933 October 2-±, 1933 December 12, 1933 karch 9, 1934 March 25, 1934 April 28, 1934 May 7, 1934 July 2, 1934 August 16, 1934 June 11, 1935 June 15, 1935 June 27, 1935 October 23, 1935 October 29, 1935 February 26. 1936 Patent April 24 , 1936 June 17. 1936 June 13, 1936 Jvxne 26, 1936 October . 0, 1936 October 3, 1936 October 16, 1936 Hobember 23, 1936 January 18, 1937 February 1, 1937 February 13, 1937 February 13, 1957 I'iarch 20, 1937 April 9, 1937 April 28, 1937 August 10, 1937 Au,-ust 26, 1937 Septeraber 4, 1937 November 18, 1937 U. 3. 2,123,457 G-er, 671,162- U. S. 2,151i651 U. S. 2,144,366 u. s. 2, 144, 367 u. s. 2,136,868 Ger. 674,488 Ger. 675,220 u. s. 2,125,854 u. s. 2,197,500 u. s. 2,132,013 u. s. 2,127,526 u. s. 2.168,064 u. s. 2,071,171 Ger. 665,216 u. s. 2,172,314 Ger. 665,076 Brit. 471,153 U. S. 2,149,917 u. s. 2,098,942 u. s. 2,1133,241 u. s. 2,194,446 u. s. 2.166,118 u. s. 2,166,119 u. s. 2,138,516 u. s. 2,192,894 u. s. 2,190,173 u. s. 2,192,347 French 829,338 French 829,339 Brit. 492, 660 Brit. 493,764 U. S. 2,160,579 U. S. 2.133,972 Brit. 501,801 U. S. 2,173,849 Brit. 505,853 43 Filing date Za ben t DecemlDer 2, 1957 U. S. 2,191,421 JanuDxy 10, 1958 U. s. 2,129,617 May 14, 1938 u. s. 2,144,368 May 14, 19o8 U. s. 2,144,369 July 2, 19o8 U. s. 2,194,924 September 23, 1938 U. s. 2,146,257 September 26, 1936 u. s. 2, 146, 258 DIVERSITY OF FLORIDA_ ■3 1262 09224 7765