E-537 April 1941 A BZYU'.J OF IP?OR:.IATIOiI OH MABASDTE By R, C. Eoark, Division of Insecticide Investigations Contents Page Introduction 2 The chemistry of ana"basine 3 The determination of analaasine 5 Occurrence of anatasine 7 The pharmacology^ of ana'Dasine 11 Tae use of ana"basin9 as an insecticide 12 Patent s 31 Heviei;7s and popular articles on ans-oasine 32 Summa,ry 34 Literature cited '. 35 Index to insects against which anal^asine lias "been tested 54 Digitized by the Internet Archive in 2013 http://archive.org/details/reviewofinformatOOunit INTIiODUCTIOK Anatasine is a liquid alkaloid vihich closely rese!n"bles nicotine in its physical, cherni cjal. , pharmacological, and insecticidal properties. It is soluble in wate- in all proportions and is less volatile than nicotine Anatasine has the r^olecular formula Cio%4^'2 ancL the follovrins structural formula: H Hj- C '\ H- C H- C C - H %^ C - H2 C-H C - K2 Hg-C C- He H A. H - C' "C C^ -C- H2 i H - C C-H CH AN ABAS IN NICOTINE The structural formula of nicotine is shown for comparison, and it is evident that no other possible pyridyl-piperidine so closely resembles nicotine as does anabasine , which chemically is beta-pyridyl-alpha- piperidine. The principal physical constants of anabasine are as follows: Anabasine is a colorless, somewhat viscous liquid which turns brown on standing in contact with air. It is very stable, appreciably basic in reaction, and forms salts in typical alkaloidal fashion. The odor of anabasine resembles that of nicotine but is less intense. Solubility: Soluble in water in all proportions. Nicotine i-s sol^lblt in water in all proportions only below 60^. Anabasine is also soluble in all organic solvents. Specific gravity : 20/20 1.0481 (Nelson, 85) Boiling point ; 280.9° at 760 mm. (Nelson, 85) Refractive index : 20 1.5443 (Nelson, 85) Optical rotation: [alpha]^ -59.66 (Nelson, 85) - 3 - On long standing at roon temperature, or in 3 to 5 days rrhen heated in a sealed tute at 200*^, anabasine auto-racemizes with a corres^oonding drop in totation. Vapor pressure : Log Pm.m. = 7.2423 - 2416.14 T^ (i:elson, 85). --it 100° the vapor pressure is 6 rm. of mercury, Anabasine is the only alkaloid that was synthesized before it was foimd in nat-ore. Its synthesis from pyridine was effected by C. E, Smith (133) in 1929 and was fully dc3cribed by him (134) in 1931. Because of its close resemblance to nicotine. Smith called s:,Tithetic anabasine neo- nicf.tine. The Hussian chemist Crekhov (90) in 1929 reported the isolation of the natural alkaloid from a weed belonging to the sugar beet family (Chenopodiaceae) . This weed, called Anabasis aphylla , is indigenous to the steppes of the Caspian region, T-orkestan, and Transcaucasia. Because of this source the alkaloid was called aiiabasine. In 1935 Smith (138) found anabasine in an American weed belonging to the Solanaceae, namely Hi cot i ana glauca B , Grah. , Itnown in the Southwestern States as tree tobacco . Anabasine is of interest to the entomologist because it is a potent insecticide, ^hen sprayed upon certain species of aphids it is reported to be four or five times as toxic as nicotine. The purpose of this review is to call attention to the promising results that have been obtained with anabasine in combating certain insects and to stimulate the American production of this alkaloid so that it may again be commercially available in this country. Anabasine is reported as being manufactured by the Staat lichen Alka- loid Pabrik zu Tzchimkent (liasalzstan) , U. S. S. 2., which is represented in this country by the Amtorg Trading Corporation of l-ew York. Since 1936, however, anabasine has n'>t been obtainable in the United States. TI-3 GH3:,IISTRY OF AI>;ASASIIS Orekhov (90) in 1929 was the first to report the isolation of anaba- sine from Anabasis aphylla . From this subshrub, Orekhov extracted, with ammoniacal alcohol, a nixtiire of alkaloids. The chief of these, called anabasine, was purified. It is a yellov/ish oil, distillable in vacuo, soluble in water, and entrainable "oir steam, Oreldiov reported the physical constaiits to be; Boiling point 145-146° at 15 mm.; specific grarTity 20/0, = 1.044; optical rotation, [alpha]g°= -47021'. The physical constants reported by Helson (85) in 1934 and given on pages 2 and 3 of this publication axe believed to be more nearly accurate than t'lose reported by Orekhov, - 4 - Analyses indicated tl^e formula C-jQH^^Ng. It formed a picrate, C-Lo2T^4N2;2CgH2(OH)(w02)3, melting point 205-207°, and a picrolonate, melting point 235-237'^.. Silicot'ongstic abid gave a ^hite amorpho'-is precipitate with even ver;;-- dilute solutions of the base. Orekhov and I'enshikov (98) in 1931 published the first of a series of papers on the alkaloids of Ana.basi s aphylla L. Percolation of the dried plant with 2 percent of ammonia in 95- percei.t alcohol, evaporation to dryness, e:?traction with 10-percent liydro- chloric acid, precipitation with 50-percent scdi-um hydroxide, extraction with . ether, drying with potassium carbonate, and evaporation yielded 2.33 ; 'ercent of a thick oil, separated by vacuum distillation (12 mni. pressure) into 85 percent of a fraction boiling at 13.5-6.5° and 15 percent arouni. 200°. The lower-boiling fraction could be separated by benzoyla- tion, by the action of nitric acid, or by vacuum distillation into a tertiary amine, C]lo^'^19^-^» ^^a-ving all the properties of the lupinine obtaii ed from Lupinus luteus , and a secondary amine, CiQHi4iJ2» designated anabasLne, which with potassrom permanganate gave nicotinic acid in good yield, and on dehydrogenation, either bj'- heating with silver acetate or by ref -uxing with zinc dust, lost 5 hydrogen atoms, forming a bipyridyl, boilini point 293-4° (picrate, melting point 151-2°), thought to be iden- tiiJBl wl th the alpha, beta' -bipyridyl of Slcraup and Yortmann , boiling point 295-6° '^picrate, melting point 149.5^). Anabasine is, therefore, very probably' alpha-piperidyl-beta-pyridine, which, however, is certainly dif- ferent from Pictet's nicotimine for which he suggested the same structure. Anabasine, prepared from the benzoyl derivative (m. 82-33) and hydJTOchloric acid (d. 1.19) in sealed tubes at 100° was reported to have the following properties: ^^qq21So, d|g 1.0455, n^^ 1.5430, alpha^]§^= -82.20*-'. Anabasine reacts strongly al.caline , is quite difficultly volatile with steam, stable for nours towards potassium permanganate in sulphuric acid; the hydrochloride salt immediately deliquesces in the air, and is dextrorotary. -he chemistry of anabasine has been studied by the Russian chemists Crekhov and associates (79, 80, 81, 82, 88, 90, 91, 92, 93,94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106), Katznel'son and associates (47, 48, 49, 50, 53, 54, 55, 55), and ilenshikov (78); and by the German chemists Bhrenstein (22) and 17enusch (158, 159); and the reader is re- ferred to their publications for detailed information on this subject. Other alkaloids of Anabasis aphylla Orekhov and iienshikov (99) in 1931 reported isolating additional alkaloids from Anabasis aphylla , called aphylline and aphyllidine. In 1937 Orkhov (95) proposed a structure for aphyllidine, '^i^^'^'^^-2'^ , melt- ing point 112-13°, alphan 5.5, and also for aphylline, ^\^^2^2'^ ^ melting point 162-4°, alpha^ 54.5, which is the corresponding saturated compound. Synthesis of Anabasine Anabasine was s^aithesized before it was found in nature, a reversal - 5 - of the usual order .in. the chemistrv of allcaloids. The s;-nthetic product ^as first made oy Snith (133) in 1929 and descri'bed in 1931. Prom its resenolance to nicotine it was called neonicotine. By the reaction of pyridine, nstallic so^lua, and oxygen a nixture of coEpot'nds \7as formed from rrhich neonicotine (oeta-pyridyl-alpha-piperidine' was isolated. In 1935 Spath and ilamoli (l49) annovjiced a nev; synthesis of dl- analiasine vhich consisted in reflijxing N-"benzoyl piperidone with ethyl nicotinate and dry sodiim ethoxide in "benzene, evapora,ting in vacuo, and heating rith strong hydrochJLoric acid vinder pressure at 130°. In 1337 Spath and ICesztler (145) resolved dl-anatasine into the active components "by means of the 6,o'-dinitro-2,2'-diphenic acids. Infra-red alDsorption spectra of analDasine O'Bjrrne (89) in 1933 reported on the infra-red a'Dsorption spectra of certain allcaloids, including anabasine. The absorption ^^irves and wave lengths of absorption bands measured between l.GO microns and 12.00 microns by means of constant-deviation spectrometers with rock-salt and fluorite prisms are given for alpha-be ta-bipyridyl, anabasine, neonicotine, methyl- anabasine, nicotine, and other alkaloids. The C-i', C-H, C-H^ and CgHg bands are present. i>Tatura.l anabasine and neonicotine show small differ- ences in absorption. Anabasine bentonite Smith (l37) in 1934 reported on the base exchange reactions of bentonite and salts of organic bases. The reaction between bentonite and salts of organic bases is princi- pally one of base exchange. Bentonite enters into base exchange with a definite chemical equivalent of organic bases where saturation can be reached. In the one sample of bentonite used 1 gram combined with 6.2 to 5.4 cc. of 0.1 N organic base, '"hen saturation is approached with most bases, flocculation is produced. Flocculation indicates that a reaction has talcen place 'dth partial or complete saturation of the silicate. Saturation is promoted by the insolubility of the silicate complex and by removal of the inorganic sa.lts by washing. Anabasine reacting in two different concentrations showed an absorp- tion close to that of nicotine. Nicotine bentonite has proved of great value in combating codling moth larvae, and anabasine bentonite is worthy of testing for the same purpose. Tld DETSK.iniATION OF MABASIN3 i7enusch and iilowitzki (l58) in 1934 published methods for the determination of anabasine. Anabasine can be qua:atitatively steam- distilled from an alkaline solution of commercial anabasine -sulfate, a nonvolatile base remaining in the residue. The distilled base can be further purified as the salt of picric acid, but even after several crystallizations from water and from alcohol, it gives no definite melt-, ing point. For the determination, add to 100 cc. of distillate 5 cc. . 8 - of 1:4 hydrochloric acid and 5 cc. of 12-percent silicotungstic acid and, after 12 hours, col].ect the precip-'.tate in a G-ooch cruciols and dry at 120°. The T7eight of precipitate x 0.1001 = grams of anahasine. Ho'.vever , in order to avoid aixy admixt'ore v^hlch vro'oJ-d give a similar precipitate, acidify slightly the 100 cc. of distillate with acetic acid and add 50 cc . of sat-ijirated picric acid solution. After 12 hours filter through a G-ooch crucihle and dry to constant Tveight at 650. On acco^ont of the soluhility of the salt, the Tveight of the precipitate x 0.29 = grams of anatasine. finally, a third quantitative procedure is offered ty precipitation ^7ith picrolouic acid, as described "before, and drying of the salt at 70°. The v/eight x 0.234 gives very good results. By this proced'ire it is possible to obtain anahasine picrolonate even in concentrations v/hich no longer jrield any precipitates with nicotine. liiown solutions of p-orified anabasine were analyzed with these re- agents. The results ootained with the different reagents were a,s follows: (l) 12-percent silicotungstic acid solution, precipitate dried at 120° C (assuming precipitate of 12^703- Si022C3_QHi4N2.2E20) , loiind 0.0088 gram anahasine (in 100 cc), theoretical 0.0090 gram; (2) cold- saturated aqueous picric acid solution, precipitate dried at 65° C. (using th.eoretical factor 0.258), foiJind 0.0080 gram (in 150 cc), theoretical 0.0090 gram; (3) cold- saturated aqueous picrolonic acid, precipitate dried at 70° C. (using theoretical factor 0.234), found 0.0292, 0.0143, 0.0072, and 0.003 gram (in 200 cc. ) , theoretical 0.0287, 0.0143, 0.0072, and 0.003 gram. I^tz (52) in 1937 reported that anabasine sulfate and nicotine sul- fate have many reactions in common. Sokolw (141) has shown that iTj'-c'rofluosilicic acid is an excellent reagent for precipitating anaoasine fluosilicate in the presence of nicotine, and it is nov shown that if an ethereal solution of nicotine is mixed with an equal voTome of ethereal iodine solution a precipitate of Cxo2i4^'2-^2*^-^ is formed, whereas anahasine does not give a similar precipitate . Surkat (15) in 1937 described qualitative reactions of anahasine vdth picric acid, phosphcmolybdic acid, and mercuric chloride. For a quantitative determinant ion, the alkaloid is distilled from sodium liydroxide and sodium chloride into standard acid and hack titrated. Zerhey, Orinick, and '"illard (152) in 1937 reported comparative tests of anabasine and its related, compuunds, its purification, and some physical constants. Anabasine is a colorless or pa-le-yellow liquid when pure, miscible with water in all proportions, and, like nicotine, it darkens on standing. An attempt was made to prepare p-ure ana-basine from its sulfate by treating with 20-percent sodium hydroxide, allowing to stand overnight, and extracting the oil layer with ether. The oil thus obtained contained all the alkaloids. It was distilled under reduced press\ire and separated into 21 fractions. Determinations of the density by the micro-pj'cnometer method, of the optical rotation with 5-percent solutions in alcohol, and of the refractive index with an Abbe refrac- tometer were made on fractions 2, 5, 8, 11, 16, and 19. Since the values were different with each fraction tested, it was impossible to tell which one corresponded to pure anabasine, but it is probable that n20^ 1.536-1.538, E^O,, 1.046-1.048, and [alpha]^^= -76.2 to 79.1°. A -liable is given showing the behavior of anabasine and the related c.l'c£-:.lcids ricotine, lupinine, collidir.e, a.id 1-atidine torrard -gold chloride, merc-oric chloride, Sraut ' s reagent, "ag:.^er's reagent, Mayer's reasent , picric acid, tari'om nitrate, chloroplatinic acid, silicotuiigstic acid, phosphoantiiiionic acid, phosphoTnolyodic acid, cadmium iodide, pctas- siun iodide + hydrogen peroxide, co'Calt thiocyar.ate , and Millon's re- agent. A taole is also ^iven sho'jins the oehavior of the different fractions to-.7ard most of these reagents and potassitin chronate in addi- tion. The most distinctive test is that with gold chloride; the crystals produced axe quite different from those forcied rrith nicotine. Sokolov (142) in 1937 claimed priority for some of these tests. CCCUEiGFCS CI JilJAIASIlS In addition to Ana'oasis aphylla , the follor^ing ^jlants have "oeen found to 2''ield anaoasine: Mcotiana tahacim (£path and Kes.itler, 147, in 1C37). H icotiana .glauca (Smith, 138, in 1935, and Zhiinura, 57, 53, in 1937 ar.d 133e). Smith (138) reported that i^icotiana gl auca roots contain ahout 1 per- CEnt of anabasirie ; it also occ^^rs in thB dried leaver;. lot more than a trace of nicotine is present. J^jiatasine xras isolated oy digestion vrith. warm 1-percent hydrochloric acid, filtration, making alkaline, aiid ex- tracting rith ethyl ether. iComura (57) in 1937 write that -'ico tiana .^lauca may "become of com- mercial importance "because it conts-ins 0.74 percent of anabasine , 7.16 percent of citric acid, and 7.90 percent of malic acid. The citric acid is concentrated mainly in the lorer leaves, vrhile anabasine is fo^^nd mainly in the yoxmg upper lea,ves. The amo'jjit of ara.ba.sine extracted with chloroform exceeds that extracted by petroleum ether by 100 percent. A considerable amount of anabasine is present in the stalks and roots. In 1933 Ihmvrs, (58) published additional information on the al".:aloid of Hicotiai'-a glauca, Anabasine was extracted from the plajit with 3-percent alcoholic ammonia solution. After distillation of the alcohol and solution of the residue in 5-percent lydrochZ.oric acid, the alkaloid was set free by alkali sation of the solution, anc extracted with et"ner. T"-^e ^'ield was 24.4 'grails of pure alkaloid per 7.5 kilograms of plant (=0.32 percent). Stanley (150) in 1924 described Nicotian a glauca G-rah. as a glabrous shrub or sma.ll tree, 18 feet high or less. A native of Argentina and oruguay, it has become thorouglilj'- naturalized in come parts of North America. In the United States it is found from western Texas to southern California; in Mexico, from Sonora to Tamaulipas and Oaxaca. Its common names are as follows: - 8 - ar"bol de tabaco lengiia de uuey tebaco cimarron "buena moza marihuana tabacon coneton Marquianfe. tabaquillo Don Juan moataza moiitie^ tacote gigante palft -^irgen tepoze^.! extranjero gretana palo virgin tronadora ^ hierba del gigante tataco ainarillo virginio This plant is abuj^dant in some parts of Llexico. It is reputed to be very poisonous. The leaves are often applied as poultices to relieve pain, especially hca-dache. An interesting report on H icotiana glauca , growing in the lo'.rer Hio Grande Valley of Texas and Mexico, was submitted by Bibby and Higdon (ll) of the Sureau of Entomology and Plant Q,uarantine in January 1940. The ;i|lant is imown by severaJ cosmon names, including the following: Arbol de tabaco, lingua de vaca, lingua de buey, mostazo monte, quebradora, sacred mustard, tabaco amarillo, tabaco cimarron, tabaquillo , tree to- bacco, and tronadora. Nicotiana glauca gro-^s on Trell-drained sandy waste land along or near irrigation canals and usually in colonies. It is a fast growing plant; one tree 4 inches in dj ameter and 25 feet tall was only 18 rao»ths old. Sprouts from stumps apparently mrJce an extrenely rapid and succulent growth, bearing leaves much larger than those on t}ie older plants. In January 1940 temperatures as low as 29° F. were recorded at Brownsville, Tex., but apparently only yoting seedlings and young sprouts were injured by the freeze. In fact, many older plants bore fresh blooms, apparently uninjured. Bibby and Higdon were informed by Ing. Tomas Leal Moreno of the Mexican Department of Agriculture that some Mexicans believe that plants of Nicotiana glauca will rid premises of fleas. It is concluded that Hicotiana glauca could be grown commercially in the lower Eio Grande Valley. Clayton and Foster (l7) in 1940 reported on disease resistance in the genus i'icotiana . H. glauca (n=12) is immune from black root rot ( Thielaviopsis a as i cola ) and highly/ resistant to mosaic, root Imot ( Heterodera marioni ), and wildfire (Bacterium tabacun ) . Smith's allo- polyploid (N. tabacum + iJ . glauca , n=35) shows resistance to root loiot and root rot. Schmuck (128) in 1937 reported on the chemical composition of alkaloids in inter-species liybridization of plants of the genus Nicotiana . N. glauca contains anabasine; N. sylvestris and N. rusbyi probably contain nornicotine; and ll^. tabacum , alata, rustica and langsdorffii contain nicotine. The alkaloids from plants of the first generation of hybrids (N. tabacum x 'S_. glauca) consisted of anabasine only, and the content of this was always considerably higher than in the original parent plant (N. glauca ) . r.ie hybrid plajits of fis third, fo'JU'tla, and fifth generations con- tained either anabariiie or nicotine as vrell as a nixture of nicotine vrith anabasine , "but in such fixtures of the anabasine predoninatsd. Th.e conplex hybrids (nakhorka x 2-li.ucc. x toba.cco) inr?j:is.bly contained gjiabasine or a nixture of anabasine aiid nicotine, ""'o ne-" alkaloids rere found in any h^j/brids. As a r\ile the first- generation hybrid con- tains only one alkaloid, typical of one of the pc?rents; in the following generation splittin;; occurs aJid plants appear bearing mixt-'Jires of the alkaloids as vrell as plants containing only one or the other of the parental alkaloids. Spath and Ilesztler (143) in 1S37 reported that a minute quantity of levo-N' methylanabasine (picrate melting point 237-8°) v/as isolated fron 1,800 grams of crude nicotine obtained from tobacco. Zul'ov (165) in 1959 reported on the inheritance of nicotine and anabasine in interspecific hybrids i^icotiana rurtica L. x iJ. glauca Orah. N. rustica contains nicotine only and i£. glauca . contains anabasine only. Comiaercia.. production of anabasine is based on the wild-grovring half- shrub Ar abas is aphylla ; in the youngest parts of this plant is contained up to 2.53 percent of anabasine. The demand for anabasine cannot be Trholly satisfied oT/ing to the low proportion of it in A. aphylla and to limited production. Breeding a new form rich in anabasine is, therefore, not only of theoretical, but also of practical interest. Of 105 h^.^brids studied, 41 contained only anabasine, 40 only nicotine, and 24 both alkaloids. a11 the anr.bar.ine-boajring plants morphologically belonged to typical mal±iorka ejad. r/ere self-fert:< le. The anab?.r:-ine content varied in these plants from 0.87 to 2.03 percent. The a:ialysis of leaves V7as conducted on unpruned plants. By me3ns of pruning and other agrotechinical treatment this percentage may be increased several times. As much as 6.61 percent of anabasine was found in the leaves of one of the u:;pruned hybrids. Kostoff (62) in 1939 reported on the nicotine and citric a,cid con- tent in the progeny of the allo-polyploid hybrid i£. rustica L. x H. gla-uca GraJ-. Kostoff was of the opinion that this alio-poljTloid as well as the ba.ckcrosses axd other hybrids between K. rustica arid Ij_. glauca ma^;^ ansv/er the de^iands of industry for ai:abasine if breeding work with these plants be done on a somewhat laj'ger scale. Some of the allo- polyploid segregates, on the other hand, gror very rapidly and give a very large amoiont of green mass, provided suitable environmental con- ditions are secured for their growth. Allo-polyploid rTicot iana rust i ca- glauca is a plant interesting from an agricultural point of view, because it segregates forns v;ith larger amounts of anabasixie (1.986, 1.449, 1.395 percent, etc.) than the parental species N. gla-uca which, when grov.m under the same invironraental condi- tions, contained 0.837 percent. At the same time the offsr^ring contain a relatively large amo'jnt of citric acid. Further generations of some of the offsprinii should give the possibility to select forms with larger content of anabasine and citric acid. The populations produced from the backcrosses can be used for the same p-urpose. It should also be mentioned here that anabasine content can be increased about three times after de- capitation, as the analysis by Zukov showed. - 10- Carl von Linne (70) in 1755 -ras the first to descriT^e Ana"basis aphjlla. It occurs on the shores of the Caspian sea. In 1797 he descri'bed 4 additional species of this genus. 3ogdanov-Iat 'kov (l2' in 1933 reported that Ana':asis aphr/jla (family Chenopodiacea-e) . grov;s ab-'mdatitly in the louver Volt;a region, sor.thern Ural, pjid especially. Kazs.kstan. The amount of anatasine contained in the plant depends on the stage of development; a sharp decline occurs during the flov/ering period and as the seeds mature, the inaximum "oeing found dixring the ve^-etative period "before and after floTvering. The raw material is, therefore, collected from the first of June till r:id-0ctcher, hut not during the time of flov?ering. The uipjciman qu.?jitity of the alkaloid (2.53 percent) is found in the small green twigs; the thick green "branches contain 0.37 percent, and the old woody ones only 0.17 percent. The best method of collection is to remove small t'^^igs s-t the level of the branch- ing of the main stem; in this ws-y it is possible to obtain a second crop of tT/igs 50 to 50 days after the first harvest. G-oryainov, G-oryainova, and Zoblova (38) in 1935 aitalyzed different parts of Anabasis aphylla and fo"ind the mazcimxm quantity of alkaloids (1.84 to 2.63 percent) in the small green twigs, whereas the thick green branches contained 0.25 to 0.41 percent. Anabasine was easily extracted from ground plant material with water. At 20° C. material containing 2.98 percent of the alkaloids yielded 2.2 percent in 7 hoiars and 2.7 percent in 48 hours when added to water at the rate of 30 pounds per 100 imperial gallons. Heating or acidifying the water accelerated the ex- traction; at 70 to 80° all the alkaloids passed into the water, and in acidified cold water 2.7 percent was liberated in 7 houjrs. A lOT-iter -under the initials C-. Z-L (46) in April' 1937 wrote that, according to Balachowsiij' , j--naba.s:' s aretioides from Irenca North Africa contains no anabasine. Frein (ill) in 1938 reported Qn the alkaloids in different species of Anabasis. Alkaloids were fo^ond in samples of Ana- basi r^ a/ohylla, A. eugeniao , A. t run cat a , A. eriop oda , A. salsa , and A. rrjo eissima . The alkaloid content varied within the sa;'ie species according to the origin of the sample, e.g., from 4.31 to 1.29 percent in A. apnyl la, and from 0.014 to 1.15 percent in A. salsa (considered alkaloid-free) . Ilyin (43) in 1938 reported on the possibilities of growing Anabasis aphylla . Of all the various species of Chenopodiaceae , only Ana basis a phylla contains anabasine. A large factorj-- situated near Chimket, U. S. S. E. , is solely devoted to the production of anabasine. Anaba sis P,t)hylla is usually found growing wild in the semiarid regions, although the nature of the soil does not play an important part. Cultivation should take place during the first part of the s-jmmer, in order that the roots of the young plants may reach the moist subsoil. The seeds ejre preferable to seedlings. Harvesting very near to the sxirface of the soil is recommended, because the plant, as a rule, assumes the sha.pe of a bush. The harvest from one plantation yielded approximately 5,000 kilograms of fresh, green, raw material. - u - TH3 PHAPJ/J.COLOGY OF AlIAMSHS ITie pharmacology of ana^asine ras first studied "by Haag (40), v7ho reported his findings in 1933. "he lethal dose of ana"basine for gaifea pigs (suh cutaneous) is 22 milligraas per kilogram, compared with 26 milligrams per kilogram for nitotine. Toxic Sjonptoms from the two allcaloids are similar, anahasine "being somewhat less exciting and more depressing. Anabasine is readily absorhed from the skin and is detoxified in the liver. It appears more toxic than nicotine to guinea pigs and ra-hbits, but nicotine is someT7hat the more active on frogs and earthworms. Gersdorff (34) in 1933 compared the toxicity of nicotine and anabasine to goldfish. As compared with rotenone, solutions of nicotine and anabasine be- come toxic at relatively high concentrations. 'The theoretical thresholds of toxicity for the three compounds against fishes from the same group, are 0.013, 8.0, and 9.5 milligrams per liter, respectively. The relatively low toxicities of the t^^o alkaloids are also reflected in a comparison of the rates of increase of the theoretical velocity of fatality with in- crease in concentration. These rates, in the same order, are 90, 5.6, and 5.2 cc. per milligram per minute. Thus rotenone is 15 to 20 times as toxic as the two alka,loids. However, if the survival time alone is considered in comparison at the regions of constant velocity of toxicity, where the time periods are in the same order, about 130, 20, and 22 ninutes, the two allcaloids have a toxicity 6 to 7 times as great as . rotenone. Anabasine is slightly less toxic than nicotine throughout the range of concentrations used. Sarguine (121) in 1933 and again (122) in 1934 also published on the pharmacology of anabasine. This alkaloid is very similar to micotine in its -action on animals. It changes the blood pressure and affects the intestines and uterus the same waj'; as nicotine, and its general effects show that it can hardly be used in therapy. The other alkaloids of Anavbasis aphylla , aphylli^lne and aphylline , proved to be of negligible pharmacological activity. :'eth:,'-l anabasine proved to be much less active than anabasine. Anich!:ov (4) in 1935 reported tha.t anabasine is vaso-constrictor on the rabbit's ear, the effect being two-thirds as strong as that of nicotine. Earuishnikov (9) in 1936 reported that the action of anabasine sul- fate on the animal orgajnism is similar to that of nicotine. Pilosofov (24) in 1936 published a study of the effect of alkaloids on yeast. 2xx>erinents with nicotine and anabasine sulfate showed that large quantities of these substances slow up fermentation, while small quantities have a stimi^ln.ti.nv--; effect find produce normal yeast. - 12 - Anichkov (5) in 1937 compared the action of cytisine, coniine, and other poisons on the carotid sinus -"ith th-at of nicotine, anaoasine, and other compu-onds. Leont'ev (58) in 19C6 reported on the pharmacolofiy of ana'basine- protein coapounds. AnaDo.tine v/ken injected Yiith protein (fro:a peas or soylDean) is almost nontoxic for the conunon laboratory animals. The sj-iptoms of intoxication with anahasine are analogo^J.s to those of nico- tine, v'hich are as follorrs: Increased irritability, lack of coordination shivers, clonic conAT.ilsions, and nervous depression. The death of the animal is, as a result, caused "by disturbances in the resporatoiT process. The protein acid obt?.ined fron soya beans, combined in equal proportion with t'le alI:a,loid, res'ilted in a.i anabasine product v/hich had no harmful effects on \7arn-bloocLed or cold-blooded anima-ls. Sxperiments revealed that the resistajace of tested animals to anaba,sine vras in the follorring increasing order: Guinea pigs, white .-nice, fish, white rats, birds, frogs. Studies were reported in 1957 'a^r P-otaian (ll9) of the effect of ana- basine on the gt seous exchange in insects, by T'arascva (152) on the effect of anabasine on the a.ctivity of the heart in insects, and by Ivanova (45) on the permeability to ainabasine of the integument of in- sects. These pa.pers are reviewed in the section of this paper dealing vdth the use of ana,basine as an insecticide. Mednilqran (77) in 1938 reported the results of compa^rative studies of the effect of certain ganglionic poisons on resioirration. The intra- venous injection of 0.04-0.05 milligram of nicotine, or 0.15-0.18 milli- grajn of ana,basine per kilogram of bod.y weight, gives rise to practically equa^l values for the excitation of respiration. TIE USi: OJ AI^ALASI^v"^ AS J'J E'SSCTICIE^ JL93G Tests with anaba„sine a-s an insecticide were first made with the syn- thetic, optica.lly inactive form ca.lled neonicotine and were reported by Smith, Richardson, and Shephard (140) in October 1930. Twenty-five bipyridyl derivatives and related compounds not previously reported were prepared and examined as contact insecticides. These included a number of isomeric bipyrid^^is, bipiperidyls, ajad pyridyl piperidines. Neo- nicotine (beta-p3'-ridyl-alpha-piperidine) was the most toxic of these compounds, compa,ring closely with nicotine, to which it is chemically similar. Alpha- pyridyl-bsta-piperidine stood next in toxicity to neonicotine of the compo-'uiids investigated. In general, the compounds with the s,lpha-beta. and beta-alpha groupings lea.d in toxicity over compounds with rings located in other positions. Solutions or emulsions of each compound plus 0.3 percent of sodium fish oil soa,p or 1 percent of saponin were tested by spraying on Aphis ru:nicis L. on dv;arf nastur- tium iDlan.ts, - 13 - 1931 Uagel (84) in 1931 reported tests vrith an c.queoua solution of dipyri- dyl sulfate containing 40 percent of the dipyricSyls, and also with an emulsion containing 80 percent of dipyridyls, upon larvae of the llediter- rpne.an flour noth (Sp hestia lai eliniella Zell.). The more concentrated dipyridyl preparation exceeded nicotine sulfate (40 percent) in toxicity, Tvhich \Yas pro'bahly due to the presence of some neonicotine in the mixture. 1932 Austin, Jary, arid I'artin (7) in 1932 reported that when a commercial preparation of anahasine sulfate, g-j.aranteed to contain 35 percent of anabasine, was diluted 1:5,600 (=1:15,000 anahasine), the insecticidal efficiency against hop aphids, ?horodon humuli (Schr.), was equal to if not greater than that of nicotine at the same weight concentration. Sodium oleate or sulphite lye was used as a, spreader. Zalkind (l5l) in 1932 studied the effect of anatasine sulfate upon the beet louse, Aphis fabae. Tests were carried out in the fields, on second-year beet plants, the flower stalks of which were entirely covered with colonies of the beet louse; and in laboratories, using Koch cups where young as well as grown-up specimens of beet lice had been puifc on sugar beet lea.ves. A 35-percent solution of anabasine sulfate wa,s tested at concentrations in water of 0.01 percent to 4 percent. Zalhind con- cluded: 1. As a contact insecticide for the beet louse, anabasine sulfate is not inferior to the best contact insecticides known. 2. A 0.05-percent concentration of anabasine in wa.ter is the mini- miom dose producing 90 percent of mortality of the louse on second-year plants. This concentration destroys all the yotmg lice; only grown-up females survive. 3. A complete destruction of ^''oung as well as of gro\7n-up lice en second-year plants was attained by a 0,1-percent anabasine concentration abundantly moistened. 4. A 0.5-percent concentration of the anaba.sine solution produces a very prompt destruction of the louse. lor practical use Zalkind advised a 0.3-percent concentration cf the anabasine solution (equivalent to 0.1 percent of actual anabasine). 1933 Craig and Richardson (18) in 1933 reported the results of studies of the relative toxicity (expressed as the concentra.tion that killed 50 percent in 24 hours) of 11 alpha- substituted N-me thy Ipyrroli dine com- pounds to Aphia rumicis L. The comuounds were made up with 0.25 percent of sodium oleate and applied as a fine spray to the wingless adults. ---14 - There ras a correlation 'oet'Teeii tlie rel-^.tive toxicity and the tasicity (dissociation const?nts) of- the corpounds , th^ former decreasinei: £-s the latter increased. The causes cf this are discussed. The toxicity of most of the corapoicids to goldiich, tadpoles, and luoin seedlings are included for conparison. The Tae-ro-nicotine vras considera'^ly niore toxic to aphids thcji the opticr-lly inactive mixt-are (dl-nicotine) and also more toxic th^n anahasine. Cpjaphell, Sullivan, and Smith (l6) in 1933 conpered the relative toxicity of nicotire, ana"basine, methyl ana'oasine, and luplnine for culicine r.osqiiito larvae. The anahasine, methyl anahasine, and, Irpinine viere preiiared from e. cbmr.'ercial insecticide laheled "anatasine sulfate, 40 percent." Based on the concentration required to kill 5C percent of a population of larv3,e culicine -nosouitoes, Gulex pipier s, C. territans , ?nd C. quinquerasci atus , in S hours \t P.S.r^o C. [84.74^ I.j, the the relative toxicity of the fotir alte-i.loid'5 is as foll^T.s: nicotine 100, anahasine 38, methyl rjiatasine 21, and lupinins 6 (?). According to the unpublished ohserva.ticn of other ^or.'cers, ijicotine and a-nahasine may 'be equally effective aga.inst apids. Ficotins and anahasine are ruch less toxic th.an rotenone against inoyquito larvae and ncusefiies, Garnan and Tc-'nsehd io2) in 1933 reported on the seasona.l life his- tory of the T7hite a,pple leafhopper, ^-phlocyoa. pom aria IvicAtee, and. experi- ments in its control in Connecticut. Extensive field ccints made in apple orchards in Connecticut in 1932 sho\7ed that the first nj^phs a-ppeared early in May, hatching- he ing complete a.hout the middls of. June; In experi- ments on the suismer hrood, sprays of nicotine sulfate and soap had some residual effect in killing eggs within the lea.ves, or rymphs after ha.tch- ing and feeding on spr.a-'-ed foliage. Ilar.y more n^rmphs hatched from un- sprayed "branches than frcm those sprayed vrith 1 percent oil and 1:500 nicotine sulfa.te. The addition of 3 pounds of soap to a spray of 1 pint of nicotine sulfate in 100 gallons of T;ater shorred no significant differ- ence in field comits. Spraying should he directed a.gainst the lower surfaces of the lea.ves. Anaha.sine* sulfate killed as na.ny nyriphs a.s did nicotine sulfate rrheii used a.t the same dilution in sna-11 field experiments. Carmaji (27) in 1933 reported greenhouse tests which showed commercial anahasine sulfate to he about 5 times as toxic for Aphi s rumicis as nico- tine sulfate. Under greenhouse conditions commercial anahasine sulfate ga,ve a good clean-up of i'yzus percicae (Sulz.) at 1:1000 without spreader. Aphis spiraecola Pfitch on spirea hushes were killed at 1:1500, and anaha- sine sulfa-te was equa.l to nicotine sulfate against n;^Tnphs of Typhlocyoa pomaria I.IcAtP.e on a-pple trees. Ho foliage injury wa,s caused by anahasine sulfa.te. Bogdanov-Kat ' kov (12) in 1933 wrote that as an insecticide the com- mercial solution of anaha-sine sulfa.te containing 35 to 40 percent of ana.ba.sine may be used as a„ spray- at a concentration of 0.03 percent with the addition of 0.4 percent of soft soa^p or naphthene soap. For orchard spraying, etc., the soap ma.y be omitted and the ajiabasine sulfa^te com- bined a-t the" same ra.te with waiter containing 0.08 percent of fine freshly slaked lime or with lime sulfur (l:60); it is not effective if used alone. - iS - It may sJ-so "be employed as a dust rith a carrier such as lime or xjith calcium arsenate, at rates of from 5:95 to 15:85. The dust is prepared ty spraying the solution uniformly over the carrier to obtain different concentrations of spray or dust. If the solution contains less than 36-40 percent of the alkaloid, the quantities are increased accordingly. The present high cost of anahasine preparations makes their ex- tensive use prohibi-cive , and further vrork should "be carried out to determine the minimum effective dosages. Tables are given showing the amount of spray or dust necessarj'- to treat a given area of orchard, vineyard, or cultivated field at a tenperat^ore of 15-20° C [59-68° ?.] The toxicity of ana"basine increases at higher temperatures, ejnd this permits of a decrease in dosage. 1934 Harman (41) in 1934 reported experiments ^rhich had been made during 1933 in three apple orchards in vrestern uev York -'ith five cover sprays of various materir.ls against Carpocapsa pomonella (L.), which was so abundant that 100 percent of the fruit was infested when cover sprays were omitted. In a badly infssted orchard of the King variety the following re- sults were obtained: Treatment, materials Stings, TJorms, Total injiiry, used per 100 gallons percent percent percent Lead arsenate 3 pounds 60 13 73 iMicotine-oil 29 14 43 First cover, lead arsenate 3 TDounds Remaining sprays, nicotine sulfate 1 pint, oil 3 quarts Anabasine-oil 19 50 69 Tirst cover, lead arsenate 3 pounds Remaining sprays, anabasine sulfate 1 pint, oil 3 quarts Check, no treatment 99 99 Slcalov (l3l) in 1934 reported on the application of anabasine sulfate as an insecticide for tobacco plants in the U. S. S, R. A solution of 20 grams of anabasine sulfate in 10 liters of water, when sprayed on tobacco plants, killed all Myzus pe rsicae (Sulz.) organisms in 48 hours; a solu- tion containing 10 grams of anabasine sulfate and 100 grams of green soap in 10 liters of water required only 24 hours. Lower concentrations of anabasine sulfate were insufficient in combating the insect. The appear- ance and the taste of the finished goods prepared from tobacco treated in the above manner were normal. - 1€ - Garman (28) in 1934 reported studies on the control of the white apple leafhopper, IN'-phlocy'ba pomaria i.IcAtee , in Connecticut. This in- sect \7as tmusually abundant on apple in 1929-1930. Anabasine sulfate 1:800 ''.'ithout soap caused a redi;.ction of 98.5 percent of second-genera- tion nymphs, ilicotine silfate similarly tested caused reductions of 89.4, 90,1, and 96.1 percent. Garman (29) in 1934 reported tests of ten proprietary'- insecticiJ'.es against Aphi s r-gmicis L. on nastiXTtium leaves in greenhouses. None T7as as effective as nicotine sulfate or anaoa-sine siilfate. At a dilution of 1:3200 with the addition of soap, anabasine sulfate vras superior to nicotine sulfate. Apparently neither inoecticide deteriorated v^ith keeping. ?ure anabasine gave "better control than pure nicotine alkaloid, "both in water alone and with p-'ore soap, '.'hen 1 quart of either sulfate was used with 4 poimds of soap flakes in 200 gallons of water against Anurami s roseus (3aker) on apple, anabasine sulfate was slightly more toxic to aphids that were actuallj?- covered with spray. In other trials both materials gave good control at 1:800 viith. soap, and favorable re- sults were obtained by combining anabasine sulfate with lime-sulrjr , Anabasine sulfate (l:1000) with 1 part of bead soap almost completely exterminated Ilyzus persicae (Sulz.) on peach seedlings. Tests on eggs of the oriental fruit moth, Grapholitha molesta (Busck) , show that anaba.sine sulfate lias no value as en ovicide, and it is apparently not a stomach poison, Fleming and Baker (25) in 1934 reported on the effectiveness of several stomach poisons against tlie Japanese beetle, Popillia .jaDonica Ne^Tm. , when determined under controlled conditions. In each test 1000 beetles were confined in 5 cages without food (so that their mortalit" could be subtracted from that of the poisoned ones to allow for the repellent auction of the insecticide on some individuals), 1000 v/ith plants sprayed with commercial acid lead arsenate (8 po-onds to 100 gallons, which proved slightly more effective than higher dosages), and 1000 with plants sprayed with the material to be tested. The efficiency'- of 8 pounds of lead arsenate being reckoned as 1, the values of 1, 2, 4, atid 5 pounds v;ere respectively 0.4, 0.7, 0.84 and 0.9. The spray was applied 24 hours before the beetles fed, and half the leaves were washed with the eo^uivalent of 1 inch of rain, which reduced the efficiency of the standard 8-go^jnd spray to 0.61. The efficiencies of nicotine and anabasine sulfate as dusts (5. percent absorbed on bentonite) was 0.22 and 0.03 respectively. 1935 Vaviloy and Ilukhitdinova (15?) in 1935 published a report on the substitution of lime for soap in solutions of anabasine sulfate. In the 'J. S. S. R. anabasine sulfate is largely used as an insecticide, soft soap or sometimes lime being added to the spray. The authors consider that the great variations in the concentrations of anabasine sulfate required are probably due to differences in the hardness of water employed. The soap serves to liberate the free alkaloid; but when the water is hard, much of the soap reacts with the calcium and magnesium salts present, so that the harder the water, the less toxic - !•? - is tiae solution of anaoasine sulfate vrith the same anoiuat of soap. In the Crimea in 1934, solutions of 0.1 percent of anaoasine sulfate were tested on -"yzus (llyzoides ) persicae (Sulz.) 'The aphids vrere immersed "oy a method alread"'- described, "but to ^-et them evenly the test tuoes v/ere slov/ly rotated round their perpendicular axes, first in one direction and then in the other. 3ach test lasted 2 minutes, after TThich the aphids were kept at 25° C. [77° F.] and 70-75 percent relative humidity for 24 ho-Jirs, and the dead and living individuals were counted. -1 stilled water was used in the control. The solutions were prepared with distilled water and water taken from a well and a river, the dei,rees (G-erman) of hardness of which were 9.8 and 15.6, respectively, and were applied alone or with the addition of 0.1 percent of soap or 0.2 percent of lime. 'Then anaoasine sulfate was used alone, the nortalitj'- percentages were 19.15, 47.56, and 60.2 in distilled, well, and river water respectively, '"ith soap, the corresponding figures were 98.91, 88.04, and 94.68; and with lime, 53.06, 63.54, and 82.95. The author considers that alkaline earths in the hard waters liberated part of the allcaloid and that the toxicity of the hard-water solutions was decreased oy the addition of soap "because it softened the water, -o determine the Gest proportion of line in sprays prepared with the well water, it was added at the rate of 0.2-0.8 percent to 0.1 percent of anaoasine sulfate. The highest mortality (74.47 percent) was olDtained with 0.3 percent of lime. G-inshurg, Schinitt, and Granett (35) in 1935 reported on the compara- tive toxicity of ana-tasine and nicotine s'ulfates to insects. In prelimi- nary work in 1931, 0.1 percent of anahasine sulfate applied as a contact spray killed 100 percent of honey^bees in 24 hours. Onl;'- 10 percent died in the same period when fed on honey containing 0.2 percent of anabasine sulfate . In 1934, in laboratory'- tests with sprays of anabasine avnd nicotine sulfate with 0.2 percent of coconut oil soap as wetting agent, each at a dilution of 1:2400 gave over 90 percent mortality of Aphis pomi Deg. and Aphis rumicis L. .^t half or a quarter of this strength anabasine sulfate was decidedly more toxic than nicotine sulfate; at 1:4800 it killed over 90 percent of both aphids. Hacrosiphum rosae (L.) was more resistant to both sprays, but anabasine sulfate was in all cases more efficient. The wetting, agent used alone killed 14, 21, and 13 percent of the three aphids, respectively. In greenhouse tests with a dilution of 1:2400 against aphids on chrysanthemums, both insecticides killed 100 percent of iiacrosiphum ( ^lacrosiphoniella ) sanborni (Gill.), but anabasine sulfate killed 87.1 to 87.8 percent of Hhopalo siphum rufomaculatum ("'ilson), and nicotine sulfate killed only 32.1 to 28.8 percent . "iThen applied as a stomach poison to Bombyx mori L. , at dilutions of 1:400, nicotine sulfate killed 100 percent in 2 days and anabasine sul- fate 30 percent in 3 days. At 1:800 they killed 95 and 15 percent respectively in 3 days. The neutral wetting agent used (O.l percent of Arescap) killed none. "uHien a,dults of Melanoplus femur-rubrum (Dag.) were fed on tomato plants sprayed with dilutions of 1:800 and 1:400 with 0.1 percent of Arescap, nicotine sulfate killed 80 and 90 percent and anabasine sulfate 40 and 60 percent. Arescap alone killed 15 percent. - 1-8 - The Kev7 Jersey State Agricii3.tural Sxpericsnt Station (37) in its • annual report for 1935, reported that, oecav.se of frequent inquiries from grorrers as \7ell as manufacturing concerns on the value of anahasine sul- fate, a stud^.' was nade of the insecticidal properties of aaji^.TDasine sul- fate as compared vrith nicotine sulfate. The results of Ginshiirg et al. (35) are summarized. Savchenko and Ilolcrzhitzlcaya (126) in 1935 reported on the imectici- dal properties of nicotine sulphite in comparison rith some other nicotine preparations. A detailed account is given of investigations in the Ukraine in 1932-1933 on the toxicity to insects of solutions of nicotine sulphite (the nicotine salt of sulphurous acid, which vras first prepared in 1S32) . In laboratory tests various aphids, the larvae of H7/po nomeuta ' oadellus malinellus Zell. and of the hug Pyrrhocoris a.pt erus (L.) '.vere immersed for 5 minutes in the various solutions hy a method similar to that of Shepard and Sichardson. The nicotine sulp'iite proved more toxic than nicotine sulfate, nicotine chJ.oride, nicotine naphthenate, or anauasine sulfate. The effect of nicotine sulphite on the aphids varied ^ith the different species and forms; the ^vingless females of the summer genera- tions were the most resistant species, 100 percent mortality of the larvae requiring a 0.105 percent concentration of 40 percent nicotine sulphite, as compared vith 0.040 and 0.053 percent concentrations for larvae of Aphis sgjDOuci L. and A. fahao Scop., respectively. The mean lethal con- centration for the various species of aphids treated T^as 0.031 percent of actual nicotine in the form of the sulphite as compared rdth 0.05 percent of chemically pure nicotine. In field tests, which were made against A phis fahae on "beet, a mortality of 96.98 percent was obtained only with a 0.23-0.25 percent concentration of 40 percent nicotine sulphite. Special experiments confirmed the higher toxicity of nicotine salts as compared with pure nicotine at equivalent concentrations, and did not support tie conclusions of de Ong ajid Shepard and Ilich^rdson, whose work is critically reviewed. The mean percentages of mortality of aphids treated with different nicotine salts and anabasine sulphite were 98 and 91, respectively, as ccnpared with 77 and 85 for p-ore nicotine and anabasine, At Goncentrat ions -equivalent by weight, hoT/ever, nicotine. cr ejiabasine pro- duced a slightly higher mortality than the salts. The high toxicity of nicotine sulphite solutions may be explained by the complex action of the nicotine and of sulfur dioxide liberated during iTj^drolysis, and by such physical properties as high viscosity and low surface tension. The effect of these factors on the toxicitjr of the various nicotine and ane^basine preparations is discussed, and the corre- lation is shown in graphs and formulas. It was found that with the in- crease in the toxicity of the preparation, the cxirve of viscosity shov/ed a pronounded tendency to rise, whereas that of the surface tension dropped. Klokov (60) in 1935 reported tests against the hessian fly, Phy t ophaga de st r uctor_ (Say) (liayetiola destructor (Say)) on wheat in the Ukraine and the Crimea. - 19 - Experiments vith dusts anc' sprays dssiined to kill the eggs and young larvae ^rere carried out on autuian- and spring-soni wheat in pots or field plots, and the results vere estimated "by comparison with vin- treated plants. Soap was added to oil sprays as a spreader. The fol- lowing were the percentage controls obtained with the more effective insecticides, the figures in parentheses showing the percentage concen- trations of the latter in the sprays or dusts: 74.3-99.2 with anabasine sulfate (O.l spray); 60,6-94.1 with nicotine sulfate (0.1-0.15 spray); 80-36 with sodium fluoride (0.75-0.8 spray); 91.8 and 95.5 with anabasine sulfate (2.5 and 5 dust, respectively); 92.4-94.1 with anthracene (10 dust with lime). The rate of the application por acre depends on the size of the plants; about 40 gallons of spray or 20 pcands of dust is suffi- cient for sprouting wheat. Tvro applications should be made during the ■neriod of mass oviposition of the fly, with an interval of 4 to 7 days. Goryainov, Goryainova, and I'loblova (38) in 1935 gave an account of tests of tho toxicity to leaf aphids, etc., of preparations from plants that produce alkaloids, chiefly Anabasis aphylla . The technique oi test- ing the insecticidal value of dusts and solutions prepared from such plants is described. The solxitions ".'ere tested as dips and sprays. The toxicity to aphids of alkaloids other than anabasine present in Anabasis aphylla (aphylline, aphyllidine, and lupinine) "'as negligible. A water e::tract of anabasine was as toxic to aphids as a solution of anabasine sulfate v.'hen the allraloid contents were about the same. Solutions of anabasine sulfate were not verjr effective against aphids when used alone, but were rendered effective by the addition of soap, or cheaper materials, including petroleum acids and residue from the manufactiire of viscose. In tests v/ith 5-percent anabasine svilfate dust with a number of carriers, 100 percent mortality of aphids was obtained on the day of the application of dusts mixed with silica gel, carbonates, chalk, or limestone. Special experiments showed tnat dusts prepared with car- bonates killed the aphids in 10 to 12 minutes, whereas when other carriers were used the insects remained active after an hour. Further tests s"^o^7ed that the effectiveness of inert carriers, such as tripoli or loess dust, can be raised by the addition of at least 15 percent of carbonates, such as sodivim carbonate, all the aphids being killed on the day of the application. I>asts of anabasine sulfate were as effec- tive as the standard nicotine dusts, 100 percent mortality being obtained in 10 minutes at 16^ to 17" C. [50.8° to 62.6° F.]. An anabasine dust (named "Aning" ) that was as effective as dry anabasine sulfate and is easier to prepare was made by wetting 2 parts of finely ground plant material ^vith 1 part of water containing 1 percent sulfui'ic acid, and after 5 to 6 hours mixing it with 4 parts of a carrier, such as limestone powder or equal parts of limestone powder and loess dust. The 7-ho\ar water extract of anabasine sulfate (30 grams per liter), containing 0.06 percent of alkaloids, gave 90 percent mortality of Aulacarium pelargi . The 24-hour extract (anabasine sulfate 0.07 percent) gave 100 percent mortality. The deficiency of water extract, however, is the fact that it must be used fresh, as it becomes mouldy if left standing. - 2fO- Howard, Erannon, and Mason (42) in 1935 reported on insecticides tested for the control of the Mexican "bean "beetle. Nicotine dusts containing 2 percent of nicotine in a "b enton it e- sulfur carrier and nicotine-"bentonite-sulfur sprays at the rate of 1 pint of nicotine sulfate and 3 pounds of "ben t on ite- sulfur to 50 gallons of r^ater gave very poor results and indicated that these mixtures are not satisfactory stomach poisons for the control of the Mexican "bean "beetle. AnalDasine sulfate was used under "both laboratory and field conditions in Ohio during 1933. At a dilution of 1 part in 100 parts of water the control was poor and there v;as moderate injury to "bean foliage. Such unfavor- able results were obtained that the use of the material was discontinued. G-arman (31) in 1935 reported that nicotine and ana.basine sulfate (1:800) gave efficient control of the whits apple leafhopper, T'yph l ocyba pomaria I.'IcAtee , in field tests without the addition of soap. Anabasine sulfate is equal to nicotine sulfate in effectiveness. Garman (30) in 1935 also reported on the toxicity of pure anabasine and pure nicotine for Aphis ruiaicis . On nasturtium leaves under con- trolled conditions, anabasine v;as superior in every case. It gave as high ,a kill as nicotine at 3 or 4 times the strength. Only mature wing- less agamic females wore counted in each experiment. Chemically pure sodium oleate (l:100) was used as a spreader. Kovaleva (53) in 1935 reported on the chemical control of the cod- ling moth in the U. S. S. R. Ivio applications of a spray of paris green, bordeaujc mixture, and anabasine sulfate reduced the percentage of injured fruit to 5.5. In tests on a sraall scale linseed-oil emulsion containing 2 percent of anabasine sulfate killed 18 percent of the eggs. Mizerova (83) in 1935 reported on the chemical control of the apple sucker, Psylla mali Schm. , in central Russia. The most satisfactory ovi- cide in the laboratory was lime-sulfur (7 percent), which killed 76.7 percent of the eggs. In orchard experiments, however, the only sprays that showed any promise were two 4-percent mineral oil emulsions, and the percentages of dead eggs on trees sprayed with them were only 40.4 and 23.1, as compared with 10.7 on ^onsprayed trees. One application in the orchard of a spray of 0.1, 0.3, or 0.4 percent of anabasine sulfate with 0,4 percent of soft soap and 0.75 percent of lime-sulfur killed 75.4 percent of the young nymphs and 42 percent of the older ones, the difference in strength of the anabasine sulfate having no effect on the rate of mortality. A second spray did not further reduce the infestation enough to justify its cost. One application of 0.75-percent lime-sulfur killed 79.8 percent of the young nymphs and 59.9 percent of the older ones. Of insecticides used against the adults, a dust of anabasine sulfate (5 percent) and a spray of nicotine sulfate (0.3 percent with soft soap) were the iaost effective. Pavlov (107) in 1935 reported a test of carriers of local importance in the manufacture of anabasine dusts. These tests were designed to find suitable carriers for anabasine sulfate dust that are available in large quantities in the black soil zone of the U. S. S. R. The anabasine sulfate used contained 28 percent of the alkaloid. In experiments against - 21 - the catttage aphid, 3i-evicoryne "brasslca e (L.), the "best results Tvere 96.8 percent mortality in 3 da^s ^7ith a 4-percent dust in ccmlDination V7ith a highly alkaline white clay and 95.7 vrith a 7-percent dust in comtination v;ith lime. The rate of application was 90 pounds per acre. In tests against the apple aphis, Aphi s pomi Ceg., all the aphids were killed in 3 days after the application of a 4-percent dust, with wood ash as th'3 carrier, at the rate of 10 grams to a 4- or 5-year old tree. A 2-percent dust with wood ash or white clay killed 98.8 and S8.0 per- cent, respectively. In experiments against the app^e moth, Hyponomeuta padellus i-ialinelluG Zell., 91.4 percent of the larvae of the fourth and fifth instars were killed in the field and 100 percent in the lahoratory within 5 days "by a 7- and 4-perc9nt dust, respectively, mixed with white clay and applied at the rate of 3.5 ounces to an cl-year old tree. Dust mixed with wood ash came next in effectiveness. Special experiments with Aphi s pomi showed that analiasine sulfate maintained its effective- ness for 24 to 28 hours after application, apparently irrespective of the carrier used. The comparatively strong action of anatasine dust upon aphids transferred to leaves dusted with it may be explained "by a considerahle fumi2;ating action. However, the experiments conducted indicate that spraying is more effective. Sorogozhskaj'-a (144) in 1935 reported field experiments against the sawflj- Caliroa l imacin a Ketz. on cherry trees in the Department of Voro- nezh, U. S. S. E., in 1934. The sprays were applied on the 5th or 6th of August when most of the larvae were hatchinrT, on the 19th of August when they were in the second and third instars, and on the 2nd of Sep- temlDer when they were full fed. Anahasine sulfate, 0.05 and 0.1 percent, and nicotine sulfate, 0.1 percent, with soft soap, 0.4 percent, acted more quickly than paris i^^reen, 0.1 percent, with lime, 0.2 percent. The hest time for spraying is when the young larvae hatch. Lisitzuina (71) in 1935 reported that in the Russian ilnion the weevils St enocarus ful iginosus Mshl. and Ceutorliynchus macula-alha Hhst. cause severe daraa^^e to poppies, which are an important crop. Observa- tions on them were, therefore, carried out in 1933 and 1934 in the Department of Voronezh. In laboratory experiments with insecticides, dusts of anahasine sulfate (l:20), lime being the carrier used, gave ■ 100 percent mortality of the weevils on the third day after the treat- ment. Sprays of anabasine sulfate and soap were less effective. Of all the insecticides tested, only calcium arsenite scorched the plants. Kraiter (64) in 1935 reported on the comparative toxicity of soaps in connection with their chemical composition and some physical and chemical properties. An accotu.t is given of laboratory experiments carried out in 1933 in Hussia on the toxicity to insects of various liquid soaps. Ttn acidity of the fatty acids extracted from vegetable oils, dolphin blubber, colophony, and naphthene vja.s determined, and neutral sodium, potassium, and ammonium soaps were prepared from them. Alkaloid soaps were also prepared by substituting nicotine and anabasine for the alkali. The tests were made on adults of Brevicoryne brassicae (L.) and a temperature of 21-24° C. [69.8-75.2° F.] was maintained. - 22 - In each experiment 50 aphids placed in a Petri dish lined rvith flannel vrere sprayed with 1 cc. of the tested solution. Control aphids viere sprayed with distilled water. The insects '-ere then transferred to glass t"umblers \7ith fresh cablDage leaves at the bottom, and the percent- age of mortality after 43 hours was calculated. It was found that the sodium soaps were more toxic in all concen- trations than the potassium soaps, and the ammonium soaps were the least effective. The alkaloid soaps '-'ere much more toxic than the alkali soaps, 100 percent mortality "being obtained in all cases with soaps containing 0.25 percent of any of the fatty acids and 0.14 per- cent of the alkaloid. At low concentrations the anabssine soaps were more effective than the corresponding nicotine soaps, probably because the latter are transformed into the molecularly dispersed dispersal condition and lose their colloidal properties sooner. Solutions of pure nicotine and anabasine and of their sulfates were considerably less toxic than the soaps with the same content of the alkaloid in the solutions. 1936 Daniel and Cox (19) in 1935 reported on control of the oriental fruit moth, G-rapholitha molesta (Busck) , in quince plantings in western New York. Tests were made with anabasine sulfate 1:800, also anabasine sulfate 1:800 S- Volck oil 1:50, but it was little better than nicotine and less readily a,vailable. Sinel'nikova (130) in 1936 reported that in tests under field condi- tions of 3. ntmber of insecticides against the woolly aphid, Sriosoma lanigernm (Hausm.), on apple in Central Asia, various sprays containing anabasine, tobacco extract, or kerosene emulsion gave 90 to 98 percent mortality. The most effective consisted of 8 ounces of 36-percent anabasine sulfate and 3 po-unds of soap or Petrov' s "Contact" in 100 gallons of water. If the aphids are ab^andant and infest the smallest twigs, the quantity of the spray used should be at least 11 gallons to each tree 16 to 20 feet high. Lesnikovskaya (69) in 1936 reported that a spray of anabasine sul- fate applied t'bree times against the San Jose scale, Aspidiotus pernio iosus Comst . , failed to give control, as it did not kill the more mature scales. ^en a certain species of fruit aphid was sprayed with paris green, the mortality was 22,4 percent, and when the same insect ^7as sprayed with anabasine sulfate, the mortality was 24.7 percent. G-arman and Townsend (33) in 1936 recorded the results of investiga- tions carried out in Connecticut in 1932-34 on the bionomics and control of the white apple leaf hopper, Typhlocyba pomaria McAtee , on apple. In 1935 tiiere was verjr little difference in the percentage of njonphs killed on trees spraj'-ed with nicotine sulfate (.1:800) alone and those sprayed with nicotine sulfate and soap. Pyrethrum soaps have given satisfactory control in some tests, but in general both pyrethrum and derris or rotenone sprays have not been so efficient as nicotine sulfate - 23 - cr rjiabasine sulfate. I'o spra:' or dust has proved satisfactory against tie adults in the field. Anon~ other insecticides for control of the vhite r.p-ole leaf hopper, anabasine sulfate has proved equr.lly if not more effective than nicotine sulfate at the sane strength. This material rras used by commercial prefers in Connecticut in 1834 rvith good results but is novT (1936) off the market and cannot be obtaii'.ed. S!:alov, Skalova, and Ileleberdinskii (132) in 1935 reported that "Insectitzin," a new contact poison made of tobacco tar, nhich is a by- product obtained in the preparation of nicotine, proved to be the most effective of the sprays tested for the control of Tlirips t abaci . "Jsed at concentrations of 0.5 or 0.25 percent vrith the addition of 0.5 per- cent of soft soap, it was considerably more. toxic than anabasine sul- fate applied at the same or even higher concentrations and caused no injury to the tobacco plrjits. In a 0.2 percent concentration T-ith 0.3 percent of soft soap, anabasine was more effective than anabasine sul- fate. Experiments carried out by Skalov and Keleberdinskii shorred that insecticides against the tlirips are most effective in control if applied at the beginning of the vegeta,tive period ^aen. the thrips are least numerous. The best method is to make t>jee applications 20, 27, and 37 days, respectively, after the planting of the tobacco. Investigations by Skalov (131) showed that spraying with anabasine sulfate is ver^/- effective against I.'yzus persicae on tobacco, a concentra- tion of only 0.2 "oercent killing almost all the aphids if both surfaces of the leaves ^ere -re 11 covered by the spray. The addition of 1 percent of soft soap increased its effectiveness. The treatment did not injure the plants or affect the chemical composition or flavor of the tobacco from them. IZremer and Ilu-^achinskii (S5) in 193S stated that a carefully mixed dust of anabasine sulfate and finely ground slal:ed lime, called "Imago- cide" and containing 5 to 10 percent of anabasine, has proved effective in destroying mosquitoes in houses, sheds, etc. It keeps r'ell in corked bottles and is applied 'Jith a hand duster; contact '-'ith the smallest particle paralyzes and kills a mosquito in 1 to 2 minutes. Kag?nova-l^harnskaya (51) in 1933 reported that, in experiments in the Russian Far East, spraying with anabasine sulfate at concentrations of 0.1 and 0.2 percent gave 100 percent mortality of the cabbage aphid, Erevicor:,TLe brassicae (L.), in 24 hours, and good results against Aphi s gossypii Glov. on cucumbers in greenhouses were obtained even with a 0.05-percent concentration. rotaraya (llO) in 1935 reported tests to control Aspidiotus destructor , '"lich has 2 or 3 generations a year in the tea regions of the U. S. S. R. Sprays of 0,07 percent of anabasine sulfate and 0.05 percent of nicotine sulfate, each vita the addition of dolphin-oil soap (l pound to 12 gal- lons), gave 89.1 and 85.4 percent mortality'', respectively, before scale formation. r-ichardson, Craig, and Hansberrj' (112) in 1936 reported a studj^ of the toxic action of nicotines, nornicotines, and anabasine upon Aphi s iumicis. - 24 - Six nitrogen heterocyclic corapo^ands, tested as sprays in 0.25-per- cent sodium oleate solution under standardized conditions, yielded the follov/ing toxic order rrhen "based upon median lethal concentrations: imabasine > l-beta-nicotine = dl-beta-nornicotine > dl-beta-nicotine > dl- alpha-nicotine = dl-alpha-nornicotine . 2he presence or absence of a raetl\Yl group on the pyrrolidine nitrogen of a pyridyl pyrrolidine is not essential for toxic action to Aphis rumicis . Compounds vrith linlcage at the beta position of the pyridine raucleus are the most toxic in this series. The relation between the beta position and toxicity in these compoionds may prove to be fairly general; it seems to hold for certain vertebrates and invertebrates. The dl-beta-nicotine is about half as toxic as natural nicotine, the laevo fraction probably containing most of the toxicity, juiabasine, the most toxic to aphids of the compounds reported here, is probably somewhat more toxic than its racemic form, neonicotine. Bel'skii (10) in 1936 reported tests of baits of fermenting molasses in large shallov; wooden ba.sins which are extensively used in the Prussian Union to catch the adults of 3uxoa seget-um Schiff . and other noctuids. In some experiments a poison v;as added to the molasses, and it is concluded from the results that this should always be done if the con- tainers used are of a tj'pe from which many of the moths can escape. Of the poisons used, sodium arsenite at a concentration of 0.05 percent retarded fermentation of the molasses, but sodium fluoride at less than 0.4 percent and anabasine sulfate and nicotine s-olfate at any concentra- tion tested did not hinder it. The relative efficiency of these poisons vras not constant during the three years' tests; on the whole, sodium fluoride (0.25 percent) appeared to be the best, though in individual tests sodium arsenate (0.05 percent) and anabasine sulfate (l percent) were superior to it. The attractiveness of the baits was increased by the add.ition of a few drops of amyl acetate. Devices that exposed the poisoned molasses by means of a wick did not prove so effective as the stajidard containers. ?or the future experiments it is proposed to use anabasine and nico- tine sulfa.tes at a concentration of 0.5 percent. Savchenlio and Ratner (127) in 1935 reported la.boratory experiments in Hussia, to compare the effectiveness against aphids of anabasine, its sulfate, naphthena-te, and resinate, and of lupinine , which is obtainable in considerable quantities from Anabasis a^iohylla.. . The aphids used v/ere ■c^phi s faba.e Scop, and Ilyzus persicae Sulz. , and the ra,te of mortality produced 'oi' spraying with tie various preparations are sho^m in ta-bles; the percenta.ges give the a.verage for both species. In the first series of tests the anabasine and the salts were dissolved in water (with or without the addition of naphthene soap) at a concentration equivalent to 0.02 percent of the alkaloid. Lupinine was also tested at a higher concentration. Then used without the soap, the most effective was anabar' sine naphthenate, which hilled 79 percent of the aphids. If its efficiency is ra.ted as 100, the relative efficiencies of the other sprays were anaba.sine sulfate 91, ajia.basine resina.te 77, anabasine 58, and lupinine 5. TJhen naphthene soap was used in the sprays, the highest kill (89 percent) was obtained with anabasine sulfate, and the relative - 25 - efficiencies viere ^nnp.'basine s^ulfate 100, anatasine naphthenate 98, analDasine 96, anatasine resinate 35, and lupinine 3. The relative decrease in the effectiveness of anabasine naphthenate rrhen combined T7ith naphthene soap v:as probably d-iie to a decrease of the hydrolysis of the soap as the result of the presence in the spray of ions of n3.phthene acid from t'-zo sources (the soap and the pjiabasine naphthenate), so that the concentration of the free naphthene acid, tvhich possesses an independent insecticidal action, '^as reduced. Fron these tests it is concluded that anabasine resinate and lupinine are unsuitable for use in insecticides. Further tests on ilyzus persicae , in rrhich various concentra.tions of anabasine and ?xiabasine sulfate were used vrith 0.4 percent of naphthene soap, and anabasine naphthenate was used alone, sho^ved that the latter spray TToiild be the cheapest, since even at a concentration of 0,03 per- cent it killed 96 percent of the aphids. Tlie a,ddition of mineral oil emulsions or of small quantities of "Conta.ct" or pectin glue considerably increased the effectiveness for anabasine. ■~ith a vie-;: to deter.ninin^- tha factors on vhich the effectiveness of these preparations depends, the physico-chemical properties of the solutions r/ere studied and are discussed in detail. It r:as found that the hydro::^:en-ion concentration exercises a considerable influence on the effectiveness of the spray, chiefly in the case of cliff erent solutions of the same prepa.ration. 'Vith the a.ddition of naphthene soap all the preparations acquired an ?.lkaline reaction, r/hereas the addition of large q-cantities of "Contact" or pectin jjlue considerablj'- increased the concentration of the hj'drogen ions, vrhich reduced the effectiveness of the spray. Tith a decrease of the s'xrface tension and viscositj'- the effectiveness of the spr.ay usually increased. There is a certain antagonism of action bet^Teen surface tension on one side and viscosity and pH on the other. A high, concentration of hydrogen ions and high viscosity usually neutralizes the effect of lo- s'jrface tension. It appears that the bicyclic alkaloids are more toxic thaji the mono- cyclic ones. The insecticidal properties of alka,loids that are similar in structure depend on the elasticity and volatility of their vapors, but their toxicity is eq-ua.lly decreased uhen volatility is too high or too lor;. The comparative effectiveness of the r;ater solutions of nicotine or anaba.sine rjid their salts also depends on the volatility of the vapors since, '7hen applied as sprays, they act as f-omigajits. The volatile ajiabasine and nicotine rapidly form high concentrations but do not maintain them for long, vrhereas the corresponding salts eva.porate sloTTly and keep up a definite concentration of vapors dviring a prolonged period, rrhich explains their relatively grea.ter effectiveness. The authors suggest the use of the term ''effectiveness" instead of "toxicity" to express the insecticidal value of alkaloids in sprays. Under these conditions the alkaloids and their salts possess equal potential toxicity, as the active principle of both is the alkaloid that penetrates into the body of the insect in a vaporous or gaseous state through the tracheal system. The insecticidal action, therefore, does not depend on the different toxicity of the preparations, but on the effect of the physical properties of the solutions on the rate of evaporation and penetration of the alkaloid into the tracheae. - 2:b- Eeference is no-ds to investigations concucted Td:/ Dashu-:evitch in 1935 rrliich indicated that anabr.sine TiS more toxic than, lupinine to the l^Tvae of mosquitoes of the Cvler. species. Ilason (76) in 195£ reported tests '-ith anr.Dasine sulfate (4-0 percent) to determine its toxicit" to the sqiJash bug, A^iTSf- tris tis (Leg.). He found that at a dilution of 1:10C anabasins sulfate ::illed a nigli percen- tage of sq"uash bugs under both laboratory' and field, conditions. Under the latter conditions slight injur;' resulted to the margins of some of the squash leaves, but it rras not serious. In combination r;ith Fenetrol (sulfonated oxid.ized gas oil) 1:200 or pine oil 1:200, serious injury'- resulted to the ;''oung growing tips of the squ^ash vines, -he percentage of kill from anabasine sulfate 1:200 was unsatisfactory, and 1:400 gave practically no kill at all. Po'^dered soap, 1 pound to 50 gallons of water, in combination with anabasine sulfate, although tested only ixider laboratory conditions, increased the hill several percent. 1937 Richardson, leonier, and Simer.ton (113) in 19 G7 fotmd that 5 percent of ax.abasine sulfate in bentonite used as a dust in the field, hilled only 5 percent of chinch bugs (third end fourth instars). There was no injury to com plants. [A mixture of anabasine sulfate and bentonite reacts to form a definite chenical comT)ound, namely, anabasine bentonite, which is nonvolatile and insoluble in water. R. C. R.] Kremer .and Iluvichinshii (65) in 1937 reported laboratory and field tests in the Crimea of the effectiveness against mosquitoes ejid sand flies ( Phlebotomus ) of dusts of anabasine sulfa.te ?rid finely ground slaJced lime. 'The results of dusting mosquitoes in buildings in various localities at temperatures varying from 1 to 30° C. [33.8-36° F.] with dusts conta.in- ing 10, 15, or 20 percent of anabasine s''Jlfate are given in a table; the stronger dusts gave 100 percent mortality in all tests and the wealiest one did so in 4 tests out of 7. It is emphasized that the dust must come in contact with the body of the insect. In hot weather the mosquitoes were pe^ralyzed in 1 to 2 minutes and eventually all died, tho'ogh a few of those dusted '-'ith the lowest concentration survived until the follov/ing de,y. The rapidity of action of the dust increased with the temperatiire . I>asting at the rate of 1 ounce to 2,000 cubic feet in inhabited houses and 1 ounce to 1,500 cubic feet in animal quarters was found sufficient to destroy all the mosquitoes, whereas 75 oiinces of tob?.cco dust would be required to fumigate the same space. In tests in houses in Sebastopol, practically all sand flies were paralyzed almost instantaneously by 10 to 15 percent concentrations of the dust, and died in 5 to 10 minutes. In the laboratory tests the mosquitoes were placed into cages pro- tected with fine-mesh wire, and were dusted from outside from a distance of 1 to I-I/2 meters with 10 percent anabadust. If the outside temper- ature was sufficiently high, the mosquitoes showed indications of poison- ing in 1 to 2 minutes. They were unable to fly, fell on their backs; their legs and heads were contorted with spasms. In the majority of cases their abdomen.s became inflated like balloons, ready to bxirst. Anattasine dusts are prepared "by ?.at\irating the ^ell-dried, sifted lime rrith the required qu^ijitity of analDasine sulf.?.te, after which the noistened lime rras nixed in a mixirxg apparatus. After 15 to 20 minutes of nixing, the preparation is slightly dried in the sun r^Xid plp.ced in a tank protected from sun and moisture. Anahasine dust is preserved in large "bottles made of dark glass, ^hich are secxirely corked. If placed in paper contp.iners or in open "boxes, it loses its potency and, therefore, especially when the temperature is high, it is essential that the anahasine dust containers oe hermetically closed. The control sprayings were made v'ith a solution containing 0.3 percent of anahasine srilfate and 0.6 percent of lime. Eunyantezev (120) in 1937 reported that of a numoer of dust insecti- cides tested against the hemp flea-heetle, ?sylliodes attenur.ta Koch, on hemp in the Gor'kii Province of the U. S. S. H. , sodium fluosilicate was the most effective and rapid in action. Calcium r'jrsenate and anahasine dust were practically valueless. Ivanova and l^'e.-niritzkii (44) in 1937 reported tests of insecticides for quarantine treatment of living plants against scale insects "by suhmer- sion in toxic solutions. In experiments in Leningrad and Sulch-Jin on the control of coccids on nurserj'- stock (chiefly citrus";, infested "branches were immersed in water solutions of various insecticides. Those tested were pure ana'basine and nicotine; naphthenates of ana'ba.sine, nicotine, sodiiom, and potassium; sul- fates of ana"basine and nicotine; and soaps of ena'basine, nicotine, or sodium prepared with fatty acids of dolphin "bluVoer. i^one of the solu- tions caused complete mortality of the coccids, e\'en with concentrations of up to 0.5 percent of the alk-^.loid and an exposure of 60 to 90 minutes, at an average temperature of 20° C. [68° ?.]. Heating the solutions to 45° C. [ll3° ?.] gave a mortalit;/- of up to 100 percent, "but equal results are o"btainahle with hot water at 50° C. [122^ ?.]. Since, ho-^ever, some plants do not survive expos\:;re to hot water at 50° C, ?jid as the alkaloid soaps proved to "be considerahly more effective than any of the other solutions tested, further investigations on their application at 40-45° C. [104-113° ?.] are recommended. The in-.;ecticidal properties of rjna'oasine and nicotine (as pure all^.- loids, naphfienates, sulfates, and dolphin oil soaps) were investigated on the imaginal stage of the following coccids: Chrysomphalus dictyospenni , Lepidosa-iohes gloverii , Pseudococcus gahani , ?. mrjitimus , and P. adonidum . i ot one of these prepojrations, even when tc^lzen in concentrations of 0.5 percent of alkaloid content in the average temperat-are of 20° to 25° C, produced a lethal effect on P. adon id-urn , wnen this insect was submerged for 40 to 60 minutes in the preparation. The mortality of C. dictyospermi reached, however, with some of tne above preparations, nearly 100 percent. Hotmrn (119) in 1937 studied the effect of ana'basine on the gaseous exchange in incects. Larvae of ?le tonus riversii Scop., after "being capped into a 0.5-percent solution of ana"basine, or a l-percent solution of pnabasine sulfate (containing 40 percent ana'basine), discharged liquid from the mouth and aiius and "became prjralyzed in 2 to 15 minutes. Tlie - 23 - rate of respiration of larvae dipped in anabasine sulfate first increased strongly, "but soon retiirned to practically the normal level; no increase in the rate was observed in those dipped in basic anabasine. In about 1 to 3 hours paral^'-sis of the older larvae passed and the normal respira- tion rate was restored; "oun^-er larvae remained paralyzed for 8 to 12 hours, and some died. It is concluded that tne .anabaslne preparations probably act on the nervous and muscular systeras and only in a secondary way on the respiratory system. Similar experiments with larvae of Pieris brassicae L. resulteidin a slow decrease in the respiratory ra-te and a general sluggishness, and death often ensued during molts. Savchenko (123) in 1937 reported on the determination of effective dosages of anabadusts [anabasine dusts] for the control of beet aphids. The results are given of laboratoiy tests against immature beet aphids of dusts of anabasine sulfate mixed in concentrations of 1 to 6 percent with various carriers. Their effectiveness was compared with that of "Aning" which gave 98.5 percent mortality. All the d.usts were applied at a rate equive.lent to 36 pounds per acre. A 4-percexit dust prepared with freshly slaked lime was the most effective, giving 93.3 percent mortality. Dusts mixed with talc or kieselg;ihr were the least effective, and although a 4-percent dust prepared with magnesrjm carbonate gave 95.7 percent mortality, it did not adhere X7ell and formed Itunps- Savchenko and Dzevaltovskaya (125) in 1937 reported the results of comparative tests on new activators for gjiaba-sine sulfate in combating the beet aphid. In the Russian Union soft soap is usually added to sprays of anaba- sine sulphate to increase their effectiveness against aphids on beet. It is, however, expensive and can be used onlj with soft water. Other possi- ble activators were, therefore, tested in the laboratory in 1935-36; they were applied in sprays containing 0.03 percent of anabasine sulfate to immature examples of Ilyzus pe rsicae (Sulz.) on leaves of beet. At this concentration anabasine sulfate alone g?>.ve 37 percent mortality in 24 hours. Several of the activators proved to be satisfactory substitutes for soft soap; the best were three samples of sodi-um salts of naphthalene- sulfonic acids, since they increased the percentage of morta,lity of the aphids to 80 or more when used at a concentration of only 0.5 percent, dissolved easily, e^id could be u.sed with hard water as well as soft. The physico-chemical properties of the solutions were studied and are discussed. Practically all the orgojiic activators (notably the sodium naphthalene- sulfonates) decreased the surface tension of the solution, which showed maximum effectiveness when the surface tension was rather less than half that of distilled water. An activator that gave an acid solution did not reduce its effect to any marked extent provided that the s-'orface tension was s-officiently reduced. On the whole, viscous solu- tions were less effective than others, as they moved more slowly along the tracheae of the aphids. A comparison of the mechanism of activation of anabasine s'olfate with that of nicotine sulfate showed them to be identical. Carbonates of alkaline metals, which are loiown to increase the effectiveness of nicotine - ^9 - - - sulfate, could, therefore, "ce used to activate ariatasine sulfate; they do not scorch "beet and so could "be applied against oeet aphids without preliminary tests. iCevskii, Jsper.skrya., and ShaposhniJ^-ova (S6) in 1937 reported on a control program for the codling- moth, (Cydia) Cai-p ocapsa -pomonell r. (L.). in I-ussia. Hicotine sulfate and anaossine sulfa'^e vyere ineffective vrhen used alon*, even if they were prepared as "fixed compounds" adsorbed on sulfur, hut they increased the effectiveness of arsenical sprrys to which they vrere added. Pavlov (108) in 1937 reported on chemical methods for controlling the pea aphid in Hussia. In field experiments against the paa aphid. M acro si - yhvm c nohrychis 3oy. , on peas in the eastern paxt of the r'rovince of Voro- nezh in 1935, no difference was observed in the effectiveness of dusts containing anabasine or nicotine. Complete mortality of the aphids was obtained on the fifth day after applying 5-percent dusts ?.t the rate of 90 pounds per acre, but 5-percent dusts at the same rate or 7-percent dusts at 45 poiTTids per a.cre were much less effective. The cabbage aphid, Erevi- coryne brassicae (L.}, proved to be more susceptible, as 3-percent anabasine dust at the rate of bo^po-oiir's per acre killed 90 percent of the aphids on seed cabbage, and a second application 8 days later killed the remainder - rivovarov and Guterman (109) in 1937 re-oorted that in experiments in Voronezh, U. S. S. H,, a dust of finely ground sicked lime impregnated with 5 to 10 percent of ana.basine s-a3.f?.te was found effective agadnst hiberno-ting mosquitoes, when applied at the ra,te of 5 ouices per 1,000 cubic feet. In the la.boratory, at temperatures ranging from 59.2 to 24.8° F. and humidity of 59 to 91 percent, it gave 100 percent mortality of culicines taken from hiberi-.,ation qunxters in foiar tests and 99.15 percent in another. Some of the mosquitoes were not killed immedia.tely but died in the course of 2 to 3 days as a result of paralysis of the motor centers. TThen the dust was a.pplied with a h^nd duster in cellars in which mosquitoes were hibernating, it killed over 98 percent of Culer. and 97,5 percent of ■Anopheles . As the dust acts only when in direct contact with a mosquito, it is essential for the carrier to be dry and for the apparatus to effect a good dispersion. Tarasova (152) in 1937 reported a study of the effect of anabasine on the activity of the heart in insects. Larvae of Pie tonus ribesii submerged in a 1-percent solution of ana.basine sulfate survived for up to 6 hours, ^^nereas they died in a 1-percent solution of sodiimi chloride in about 2 hours. The rate of pulsations of the dorsal veisel in the larvae submerged in the anabasine sulfate solution at first somewhat increased, but became normal in half an hour,.- ".Taen the solution was applied with a brush the larvae reacted immediately by strong movements and emission of fluid from the mouth and ajius; in 7 to 10 minutes paralysis occurred, and the rate of pulsation of the dorsal vessel increased four times as compared with the normal ra,te. The paralysis continued for a few hours (up to 24), after which the larvae appealed to recover comj^letely . The action of the poison on the pulsation was much less noticeable when the ventral nervous chain was cut, which suggests that anabasine sulfate - 30 - acts not directly on the circulr.torr' sycten, "but on the nervous and muscular systems, llxperiments on the direct application of anabasine sulfate to the dorsal vessels of larvae of Pieris brassicae dissected alive shovred that ever, concentrations as lo^" as 0.00001 percent result in an imraediate and final cessation of its pulsations. This suggests the possibility of using the dorsal vessels of these caterpillars as an indicator for anabasine sulfate. Incidentally, the experiments showed a characteristic difference in the rate of pulsation of larvae parasitized by Apan teles glom eratus L. , in which it was 6 per minute, as against 29 in the normal caterpill?jrs. Caterpillars fed on nast-urtixm leaves had an irregular pulsation rhythm. The action of anabasine sulfate on the dorsal vessel of 51atta orientalis L. was only temporary. Ivanova (45) in 1937 reported a study of the permeability of the in- tegument of insects with regard to anabasine. Experiments v.'ith dialysers prepared from the integuments of larvae of Fieris brassicae and Pteronus ribesii showed that the degree of penetration of fluids is variable and depends on such factors as food, season, parasitization, etc. The chitinous cuticle is penetrated very easily, but the hj^podermal layer presents an effective barrier to penetration. Anabasine and anabasine sulfate facili- tated penetration of fluids through the integuments, the rate of penetra- tion increasing with the increase in the concentration of the poisons. It is suggested that anabasine acts by narcosis of the hypodermal cells. Savchenko (124) in 1938 reported that nicotine sulfate is more potent than anabasine sulfate when tested upon beet flies. Under favorable meteorological conditions, and in the presence of soft or medium-hard water, and provided liquid soap is added to the solution, nicotine sul- fate can be used at a concentration of 0.06 percent, and anabasine sulfa.te at 0.08 percent. If the water is hard or the weather is cool, the con- centration of the solutions should be increased by 0.01 to 0.02 percent. Liquid soap can be replaced "oy sulfonates derived from petroleum and, in certain cases, even by sodium carbon?.te. 1938" Sugak (151) in 1938 reioorted that aphids on lupin, of which Aphis medicaginis ICoch was the most common, were successfully controlled by spraying twice with soap solutions containing anabasine sulfate or nicotine sulfate. Fulton and Howard (26) in 1938 tested anabasine sulfate with and vrithout oils upon the squash bug, .Inasa tristis (Deg.), Tested upon the squash bug, anabasine sulfate (40 percent) at 1:200 killed only 8 percent after 72 hours at 80° F. and 70 percent relative humidity. Under similar conc.itions nicotine sulfate at 1:100 killed 19 percent. The addition of 1 percent of certain oils (teaseed, corn, peanut, olive, petrolatum, and tung) , emulsified with sodium lauryl sulfate, to anabasine sulfate or nicotine sulfate solutions greatly increased their toxicity to the squash bug. The mixtures of oil with nicotine sulfate 1:100 were more toxic than the mixtures with anabasine sulfate 1:200. ■ • . ._ . 1940 Yothers inc. Griffin (l60) in 1940 reported tests made vrith insecti- cides upon the r/ooll;^'- ijTole ap".:id, j ^riosom r. Irniger'jn (Hausm.;, and the green apple aphid, A-phis poai Leg., at "'eno'-tcliee , Wash., diaring 1931 to 1933. The results of these tests indicate the follov/ing conclusions: Ana- oasine sulfate and nico-cine sulfate cxe, at the greatest dilutions tested (l:4800), ahout equal in effectiveness against "both the rroolly and the green aphids. 3ach gave approximately 97 percent kill of the woolly aphid at the above dilution used with an all^^lated naphthalene sulfonate as a wetting agent, inclusive of 58 percent killed oy the latter alone. Somewhere "between a dilution oi 1:3200 and 1;4800 ooth analoasine sulfate and nicotine sulfate, even with the \;stting agent douhied, "begin to fall off from 100 percent kill of the woolly aphid. Gomenhfcre "between the same dilutions they also "begin to fall off from 100 percent kill of the green aphid, with sodium oleate as a wetter j "but with the wetter not in- creased at ti..e greater dr'luticr,, as is the case vrl th the- ;roolly aphid. Against the green apple ap'nid nicotine ond ana"bac'jne siilfate ^7ith acces- sory agents gave alinost complete mortality up to dilutions of 1:3200, and the anahasine gave 95 percent kill at 1:4800. PATEI^TTS ICatznel'son and Ka"bac"hnik (53) in P-ussian patent 39.108, issued Octo"ber 31, 19*54, d&scriue a prccest; of making a;:r*.noana"basine "oy heat- ing ana'basine wifh amides jf alkali metals in the presence of organic solvents. 3fimov (21) in ".ussian patent 40,355, issued December 31, 1934, descri"bes a process of m;?i.'.ng nicotir3 and ana'basine sulphites "by treat- ing the alka,loids with S!-.j.phurou3 a.ci d. Dashicevich (20) in Russian patent 47,865, issued July 31, 1936, de- scri"bes the preparation of salts of ana'basine for use as insecticides. Anabaslne is treated in a solution or directly with \7e£irr acids or their anh;'c"!j-ides, e.g., hydrogen sulphide or car'oon dioxide, and the salts formed are separated from the solution. Sokolov and Kretov (143) in Itussian patent 51,137, issued Hay 31, 1937, describe the preparation of anabasine fluosilicate ^oy treating a solu- tion of anabasine or its sulfate consecutively'- v/ith fluosilicic acid and ethyl alcohol or methyl alcohol. Smith (139) in United States patent 2,033,855, issued IXarch 10, 1936, applied for Julj- 5, 1934, claims the method of preparing organic base- bentonite compounds, which comprises bringing to^'efner, in the presence of water, bentonite and organic bases of sufficient alicalinity to be titrat-able with mineral acids. Anabasine is mentioned as a base thr.t reacts readily with bentonite. IIcGonnell (73), assignor to Tobacco By-rroducts and Chemical Corpora- tion, in United States patent 2,071,171, issued ? eoraBXi' 16, 1937, applied for June 15, 1935, claims a fiimigating package consisting of a "nermet- ically sealed metallic receptacle having its vertical side wall scored - 32 - to provide iaiock-outs, and ?. pjni-zfmt v;ithin end. only partly filling the receptacle, the fiinigont consisting of a com oust ible material, an oxygen- supplying material, and a parasiticide material rrhich -^Till evolve a para- si ticidal vapor during fumigation. There are a nurater of such parasiti- cides, such as, for exrxiple, nicotine, anabasine, pyrethrum, derris, naph- thalene, thiocyanates, and sulphur. A specific mixture contains about 67 percent of dry povrdered tobacco, 14 percent of ?Jihydrous nicotine of 98- percent purity, ^jid 19 percent of sodiuii nitrate. Marlcr/ood (74) in United States patent 2,123,248, issued July 12, 1938, applied for January 14, 1937, claims the substantially v;ater- insoluble re?.ction products of peat rrith organic bases of the group consisting of arecoline, anabasine, codeine, ethylene diamine, and piperidine. These products are made ^oy bringing together peat and the organic bases in the presence of vrater. E3VIEV:S AID PCPULA2 iiSTICLSS OS Al-TAEASIIGl Smith (133), in the United States Department of Agriculture's Year- book of Agriculture, 1928 (published in 1929), called attention to neonico- tine, a synthetic compotmd v,'hich is equivalent to nicotine in toxicity to certain insects. The Oil, Paint and Drug Heporter (134) in April, 1930, called atten- tion to Snith' s paper on neonicotine Tzhich v/as presented at the Atlanta meeting of the American Chemical Society. The Eevien of Applied Ento- mology, Series A (134), abstracted this report and called neonicotine a po'rrerful ne\7 insecticide equal and perhaps superior to nicotine itself. Smith's paper rras later published in the Jo'jjrnal of the American Chemical Society (134). Eomanovich (117) in 1932 reviexred the literature on nicotine, neo- nicotine, and anabasine. The toxicity of Anabasis aphylla L, v;as laiotm among the inhabitants of Central Asia many years before this property attracted the attention of the investiga.tors at the LIoscot; Institute of Chemico-Pharmaceutical Investigations, The active principle, anabasine, in some specimens of the plant reaches 2 percent. The insecticidal properties of anabasine were investigated in 1930 at the All-Union Institute of Plant Protection. A, II. Illinsky at Leningrad and Z, I^T. Shirokova at Hoscor;, both specialists of this Institute, shor/ed that the toxic properties of anabasine are not inferior to those of nicotine, and, consequently, it may be used T/ith success as a contact insecticide. An anonynous (l) \7riter in June 1932 reported in the Pharmazeutische Uonatshefte of Vienna that anabasine is an alkaloid obtained from Anabasis aphylla gro^jring rrild in Turkestan. It is used as an insecticide and is sold by the Amtor;; liiight (61) in 1933 v/rote that the utilization of fruits and vege- tables had been aided Vj chemical discoveries. Prom pyridine, a consti- tuent of coal tar, a substitute of nicotine has been synthesized. This product, called neonicotine, has recently been found in a Russian rzeed and has become commercially available. - 3.3 - HoPTk (114) at the Fifth rr.cific Science Congi'ess, Canada, 1933, re- ported on recent develcpaents in insecticide research. For mony years efforts have teen made to s^.Trithesize a cocpound that rould have insecti- cidal properties sinilar to those of nicotine. The most promising of these is neonicotiiie, fo'JLnd ty Smith, Kichardson, fjnd Shepard to compare fa.voraoly vzith nicotine in killing the bean aphid, Aphi s rionicis . Recently Russian investigators h-ave fo'and neonicotine (called anahasine "by them) in a r:eed of the sugar -"beet family knom as Anahasis aphylla . This plant contains ahout 2 percent total alka-loids, including ana'oasine, methyl anahasine , and lupinine. An extract of the Anabasis plant has recently been placed on the n?j:ket under the n-yne of anabasine sulphate. In 1934 an anonymous (2) v/riter in Science Service called attention to anabasine as an insecticide. "Anabasine is a double discover^--. American chemists, striving to make something stronger than nicotine, synthesized a compound vhich they called 'neonicotine.' At the same time, Hussirn chemists extracted a most efficient insect poison from a common vreed bearing the classic Greek name Ar abasis , rxid cr21ed in anabasine. A com- parison of the synthetic 3X.C. the natural compounds shorred them to be chemi cally i dent i cal . " Anabasis is a -jenus of dry-land vreeds common in North Africa, Asia Minor pjid parts of Russia. There are about fifty species, of r/hich only one, anabasis aphyllum , ha.s been investigated as a source of insect poison. The plant is related to such common American •"eeds as lamb's quarter, tumbletreed and greasevrood. 'Chile chemists and entomologists are looking into its useful- ness as a source of aphid poison, botanists of the United States Deprxtment of Agriculture are undertpJcing tests to find tvhether it can be gro77n rzith profit in some of the w.arm, dry lands of the Southnest, V7hich are similar to its native habitat." The United States Deprxtraent of ^Agriculture, Bureau of Cher.iistry and Soils' (155), in its annual report for 1934 referred to the ^ork of Nelson in determining the physical properties of anabasine. The United States Department of Agriculture, Bureau of 3ntomolngy and Plant Ouoxojitine (156), in its anivoal report for 1935 called attention to Smith's isolation of anabasine from I'icotiana .?;lauca grov7ing in the Scut h'-e stern States. Robinson (llS) in 1935 published a review; of the literatvire for 1933- 34 dealing v/ith the chemical constitution of anabasine, and other alka- loids. Orekhov (94) in 1936 reviev/ed recent alkaloidal investigations. The production of anabasine is organized at the Chimkentsky plant located at ICazalcstpji, U. S. S. H. , v/here the rav/ material is fo\ind in great abundance. - 34- Ann-basine not only replaces nicotine for many purposes, "but in some re- spects it is regarded as a "better insecticide thari nicotine. Contrary to expectations, the experimental v;orl: indicp-ted that the introduction of a methyl group caused a sharp decline in the toxicity of ana"basine. Martin (75) in 1936 discussed compounds structurally related to nicotine, including anatasine, and speculated upon the reasons for their high insecticidal efficiency. I^oark (115) in 1936 revieT^ed vrork on anabasine published during 1934 and 1935 "by Smith, Nelson, G-insburg et al., and G-arman. An anonymous (3) rrriter in 1937 reported a talk before the Vegetable Growers Association of America by T. H. Parks of Ohio on nevr insect control measures. Reference is made to rotenone, pyrethrum, nicotine, and anabasine. Shepard (129) in 1939 reviewed information on anabasine and compared its insecticidal action v;ith that of nicotine, nornicotine, and related compounds. SUl^MAHY Tests to determine the insecticidal efficacy of anabasine and its salts have in most cases been carried out under such conditions that it is difficult to assign a quantitative value to the results. ?or that reason the compiler has not indicated the effectiveness of anabasine against each species of insect tested but has only listed the species with references to the publications describing the results of the tests. In general, the published reports indicate the following: Anabasine closely resembles nicotine in its physical, chemicp.l, and insecticidal properties, but there are some important differences. Ana- basine is less volatile than nicotine and, as might be ezzpected., is less effective as a ftimigant. As a contact insecticid-3, anabasine is eo_ual to or even superior to nicotine, especially against a.phids.. Sore experimen- ters have reported that anabasine is five times as toxic as nico-.-ine when spra.yed upon the bean a,phid ( Aphis rumici s L.). As a stomach p':'l'^:n to insects, anabasine appears distinctly inferior to nicotine in tcr -r, -i:pon the larvae of the oriental fruit moth, red-legged grasshopper, I.le./.can bean beetle, Japanese beetle, honeybee, and the silkworm. Anabasine appeejrs valueless against the eggs of insects. It would seem, therefore, that anabasine is a valuable contract in- secticide, especially for use against aphids; but that little can be ex- pected from it as a fumigant, an ovicide, or a stoma.ch poison. However, tests of anabasine as an insecticide have been limited, and new uses for it may be found. It seems well worth while to test its suitability for the control of the pea aphid and other insects now combated with nicotine. - 3-5 - LII3RAT'U53 CI ED 1. MOITYIIOUS 1932. [Anabasin.] ?hann. Ilonatshefte. 13: 137. J\ine 1932. 2. MOITTMOUS 1934. Anabasine as an insecticide. Science 79: 2049. Sci. Sup. p. 10. 3 . AiTONYIiOUS 1937. Anabasine, nevr insecticide. Ilarket Gro^'ers Jo-or. 60: 102. February 15, 1937. 4. ii:iCHKOV, S. V. 1935. L'anabasine , poison ganglionnaire. Arch. Internatl. de Pharciacodyn. et de ?her. 51: 357-380. [Abstract in Chen. Abs. 30: 6451. 1936.] 1937. The action of cytisine, coniine and other poisons on the carotid sinus. Arch. Internatl. de Pharmacodyn. et de Ther. 55: 61-75. [Abstract in Cher:. Abs. 31: 5435. 1937.] ?jid PL3:SCHZITZ3P.. A. 1935. Das Anabasin als ganglionares Gift. Trav. Acad. "lilitaire Med. Armee Rouge URSS 4: 261-263. 7. AUSTIN, M. D., JAEY, S. G. , and IIARTIN, H. 1932. Some nevr insecticides and possible insecticide-fungicide combinations. Hort, 3d, Assoc. Yearbook 1: 85-92. [Ab- stracts in Chem. Abs. 27: 5454. 1933; Rev. Appl. 3nt. (A) 21: 90. 1933.] 8. AWA^IUIIOV, ¥.. 1935. Feues uber die Bekanpfung der Zuckerruben'vanze. Soviet Sugaj: 1935. Ho 4: 23-26. 9. BAEUISHi:iKOV, I. A. 1935. Action of anabesine sulfate on the animal organism. I. Joar. Physiol. (U. S. S. R. ) 20: 79-86. [In Russian. Abstract in Chem. Abs. 30: 6050. 1936.] - 36 - 10. B^L'SKII, B. I. 195S. On the technique of catching injurious noctuids \7ith molas- ses. iMauch. Zap. Sakh. Proraysh. 12: 99-107. [In r.ussian. Abstract in Rev, Appl. 3nt . (A) 24: 643-644. 1935.] 11. BIBBY, F. I., and HIGDOH, 17. D. 1940. Notes on Nicotiana glauca in the lo^er Rio C-rande valley 01 Texas and Llexico. Typev^ritten report, 6 pp. 4 figs. 12. BOCBAEOYA, S. 1935. Das Anatasin und seine Anrrendving zrx Bekampftmg der land- wirtsch?.ft lichen Schadlinge. Ajiaa-Ata u Iloskau: Ilas- Icraiogis 1935 (32 S.) 25 Hop. 13. BOGrAi'iOY-KAT" ::ov , IT. u. 1933. Ana'oasine and its application. L'oskva, Vses. G-os. Ob'ed. BorlDe Vred. Bol.'Sel. Lesn. Ilho:. 12 pp. (All-Un. St. Ass. Contr. Pests Bis. Agric. For.) [In Bussian. Ao- stract in Be v. Appl. Ent. (A) 21: 579-580. 1933.] 14. B0L0'3'i:C0V, S. M. and BABAi-Sl^IO , S. E. 1936. Uber die Bestinmung der Alkaloide in Anaoasins-'olfat. Phar- maz. J. 9, No. 1: 22-26. 1936. 15. BUMAT, S. 1937. Simplified determination of alkaloids in commercial anaba- sine sulphate. Farm. Zhur. 1937, I^o. 4: 228-234. [in BussieJi. Abstract in Chem. Abs. 52: 5905. 1938.] 16. CAIIPBELL, P. L., Sl-LLIYAN, T7. 1'., and SI.'ITE, G. P. 1933. The relative toxicity of nicotine, anabasine, methyl anaba- sine, ?.nd lupinine for culicine mosquito larvae. Jotir. llcon. 3nt. 26: 500-509. 17. CLAYTON, 3. E., and POSTER, H. H. 1940. Disease resistance in the genus Nicotiana . Phytopathology 30 (1): 4. January 1940. 18. CRAIG, L. C, and RICPIARDSON, C. K. 1933. Insecticidcil action in the nitrogen heterocyclic compounds. Ic^a State Coll. Jour. Sci. 7: 477-485. - 37- 19 ♦ riANl3L, D. M., and COX, J. A. 1935. Oriental fruit moth control in quince plantings. IJew York State Agr. ixpt. Sta, Bull. 569. 15 -px>'t illus. 20. riA^EIffiVICE, 2. ¥.. 1936. Ana"basi"-e for insecticidP-s. Ivussi^n patent 47,365, J'oly 31, 1C36._ [In Kussiaa. A^stro.ct in Chen. A"bs. 33: 3515. 1J3S.] 21. z?n.:ov, V. M. 1934. i^cotin^ snc'i ansljaeine sulphites. I^uss'^an patent 40,355, rsco-j'Der 31, 193i. [Ahdtract in Chen. Ahs, 30: 3948. 1936.] 22. SHiuIL* 513111, II. 1931. Zur Kenntris der Alkaloic'e des Tahaks. Arch, der Fhaxm. £59: 6:.r-Co'-\ [Abvitract in Gh3n. Abs. 26: 1386. 1932.] 23. — i and jIAP.^TGP.^iF, I. 1934. tJber die l^r.trl/tische Lehjdrierun^ cyclischer 5asen. II. 2er. iJuut. Jhen. G^sch. 6?: 465-491. 24. riLOSOFOV, I.!. S, 1935. 3fiet des alcaloides sur la levore. 5ull. Assoc. Chim. 53: 787-791. [ADstract in Chen. Acs. 50: 8512. 1935.] 25. rLSliniG, W. 2., and BAISR, F. S. 1934. The effectiven?ss of rtomrxh-poison insecticides on the vTap-^neGe "beetle. Jour. Agr. Res. 49: 39-44. 25. FUIICK, R. A., and HOTTARB, 1^\ F. 1938. Effect of addition of oil on the toxicity to plant bugs of derris and other insecticides. Jour. Scon. Snt. 31: 405-410. 27. GARIJill, P. 1933. Notes on the comparative toxicity of anabasine sulphate and nicotine sulphate for aphids and leafhoppers. Conn. Agr. Expt. Sta. Bull. 349: 433-434. 28. 1934. Studies on control of the nhite appld leafhopper in Connecticut. Jnur, 3con. Snt. 27; 361-564. ;9. 30. - 3B - 1934. Study of aphicides. Comprrison of ten commercial products. Conn. S.tate "^rt. Ann. P.ept. 33, Conn. At. 3xpt. Sta. . Bull. 3G0:. 46C-451. 1935. Torcicity of pure ,ana"basine and pure nicotine for Aphis ruiaicis . Conn^ State 3nt. Ann. Hept. 34, Conn, Agr. Sxpt. Sta. Bull. 355: 238-239. 31 1935. Control experi^nents against the vihite apple leaf hopper. Conn. State Snt. An::. Eept. 34, Corji. Agr. Zxpt. Sta. Bull. 368: 239-241. 32. and T0^.1>TSEiG, J. P. 1933. Seasonal life history of the rrhite 3.pple leafhopper "nd • experiments in its control. Conn. A-^ . -Ixpt. Sta. Bull. 349: 429-432. 33. and TCVJHSEHD, J. ?. 1935. Control of the white apple leafhopper. Conn. Agr. Hxpt. ■ - Sta. Circ. Ill: 37-47. 34. gsilSecejf , ::. A. 1933. A comparison of the toxicity of nicotine a-nd anabasine. •J car. Ar.er. Chem. Soc. 55: 2945. 35. GBTSBUHC-, J. ::. , SCHIIITT, J. B. , and CPJlilSTT, P. 1935. Comparative toxicity of anG.Dasine er.6. nicotine sulphates to insects. Jo or. Agr. lies. 51: 349-354. 35. GOEBACHSV, S. V. 1934. Vapor pressures of ana'basine and nicotine.. Jo-'Jir'. Appl. Chem. (U. S. S. R.) 7: 388-391. [In itussian. Abstract in Chem. Ats. 29: 2045-2046. ' 1955.] 37. GOPIAILIOV, A. A. 1932. Preparation of an insecticide. Russian p-tent 31,185. August 30, 1932, granted July 31, 1933. - 39 - 38. XP.yAINOVA, N. S. , ar.d ::03L0''A, F. V. 1935. ArlDeiten uoer Pflpxizsngifte. Irarxs. Inst. Fertil. ilo. 123: 235-249. Leningrn-d. ('"itli a s-uuiaary in German, p. 290). [In Hussian. A'Dscracts in Eev. .ipr>l. 3nt. (A) 24: 351- 352. 19 o6; Chem. Abs. 30: 5575. 1936.] 39. GOZYAIKOVA, N. S. 1931. Verschiedene Methoden der 5estiminiins das Anabasins. 3ul. ^"^iss. CheiP . -PheiTni . ?orsch.-Inst . [mss.J 1931: 211-213. 40. HAAG, H. B. 1933. The pharnacology of anabasine. Jour. Pharmacol. 43: 95-104. 41. KAFIAI^T, S. 17. 1934. Codling CO th control experiments durin.3 1933. Joiir. 3con. 3nt. 27: 222-225. 42. E0:7A2D, l\ . P., EEAi:NOi: , L. I?., and I.tASOiT, H. C. 1935. Derris and other insec-^.icides for the control of the I.Iexi- ccn bean beetle. Jo^^r. Econ. Ent. 28: 444-446. 43. ILYO, M. M. 1938. The study of Anabasis aph^lla T7ith a vie-.v of its economic exploitation. Eot, Inst. Acad. Sci. U. S. S. R. 1938, Ser. V, fasc. 1, 401-416. [In Hussian. Title in Imp. Inst. ^uart. JBibl. Insecticide Llaterials Veg. Origin. No. 5. October-Iecember 183o.] 44. IVAMOYA, H. A., and iiELaEITSICI , B. G. 1937. The estimation of ineecticides for quarantine treatment of living plants against scale-insects by submersion in toxic solutions. Plant Frot. fasc. 12: 129-136, 8 refs. (vrith a summary in English). Leningrad. [In Russian. Abstract in Rev. Appl. Ent. (A) 25: 660-661. 1937.] 45. IYAI\iOVA, P. G. 1937. The permeability of the integument of insects with regard to anabasine. Izv. l..urs. Prild. Zool. 1936, ^6, No. 3: 25-32, 10 refs. Leningrad. fin Russian. Abstract in Rev. Appl. Ent. (A) 25: 799-800. 1937.] 46. K-L, G. 1937. La nicouline. Prog. A:,t. et Vitic. 54 (14): 321-324. April. - 40- 47. KAmCHNIK, 11. I., and KATZI^'EL' SON, 11. I;I. 1934. Aminr.tion of alkr.loids t/ith sodiiim and potassi'Jm amides. II. alpha- and alpha '-aninoano-lDasines. Compt . Rend. Acad. Sci. U. S. S. P.. 4: 44-47. (in German, 47-50.) [Acstract in Chem. ATds . 29: 2171. 1935.] 48. and ICATZLE:L ' SON , M. M. 1935. Striictui'e of the isomeric chloroanatasines. Eer. Deut. Chem. G-esch. 68B: 399-402. [in German. Abstract in Chen. Ats. 29: 3344-3345. 1935.] 49. and KATZiffiL'SON, 11 . M. 1935. Amination of alkaloids with sodium and potassiim amides. II. aJpha-aminoanata-sine. Bull. Soc. Chim. l5] 2: 57S-582. [In Trench. Abstract in Chem. Ahs. 29: 4758. 1935.] 50. and IvATZlIEL' SON, M. U. 1935. Amination of alka,loids \7ith sodium and potassium amides. Ill The structure of chloroajialDasine isomers. Compt. r.end. Acad. Sci. U. R. S. S. 2: 35-39. (In English, 39-41.) [Abstract in Chem. Ahs. 28: 5847. 1935.] 51. ICAGAI^OVa-KHARNSKAYA, - 1936. Test of insectofungicides and determination of dosages for the control of pests and disea,ses of vegetables, pp. 153- 154. Sumnaxies of reports of the Scientific Research Institute of Plant Protection for the year 1935. Plant Prot. fasc. 11: 149-157. Leningrad. [In Russian. Ab- stract in Rev. Appl. Ent. (A) 25: 580. 1937.] 52. KATZ, S. A. 1937. Eine Unterscheidraigsreaktion z^7ischen Anabasinsulfat vmd Nicotinsulfat. Ztschr. f. Analyt. Chem. 108: 408. 53. KATZMEL'SOis H. H. , and ICABACia^IIC, I.I. I. 1934. Aminoanabasine. Russian patent 39,108, October 31, 1934. [Abstract in Chem. Abs. 30: 3446. 1936.] 54. and KAEACMIIv, l.I. I. 1934. Amina.tion of alkaAoids v/ith sodium ajid potassium amides. I. alpha-aminoancabasine . Compt. Rend. Acad. Sci. U. R. S. S. [N. S.] 1: 406-409. (In German, 409-411.) [Abstract in Chem. Abs. 28: 4059. 1934.] - 41 55. and ZAEACHl-'IK, M, I 1935. Agination 'b^'- ir.eriis of socJ.un and potassium amide in the allcaloid series; alpha- and alpha'- amino ana-tasines. IV. i'itrs,tion- of alpha' -aminoajia-tasine. Compt. 5.end. Acad. Sci. U. ?-. S. S'. (1935) 3: 159-172. Also Ber. Deut . Ohi C-esch. 68B: 1247-1251. [in German.' A'ostract in Chem. Ahs. 28: 6238. 1935.] 55. and KA3ACHNII IvI. I 1935. Introduction of the amino group into compounds of the alka- loid series "by the action of sodium and pota.ssium amides. I. Aminoanatasine. Bull. Soc. Chim. [5] 2: 521-525. [In French. Ahstract in Chem. A^s. 29: 4013. 1935.] 57. KHLIURA, M. 1937, Commercial products obtained from N icotian ca glauca . Tahak S. S. S. E. , ITo. 2, 55. [Abstract in Chem. Abs. 31: 5942, 1737.1 58 1838. The alkaloid of Njcotiana g (U. S. S. P..) 11: 105-108 B-ussian. Abstra.ct in ca. Jo^or. Applied Chem. (In English," 109.) 1938. hem. Abs. 32: 4282. 1938.] [In 59. ICLYACHKIImA, B. A., SXUGATZ::iI, lA. K., and ZILBSHG, F. D. 1931. Kolelcul^xzustand der Silicor:olframalkaloide. Verbindung mit Silico'7olframsa"are. Bull. ITiss. Chem. rhajrm. Forsch. Inst. [?.uss.] 1931: 203-208. 60. laOKOV, 3. V. 1935. About the system of nea.sures in hessian fly control. Bull. Ulcrain. Sc. E.es. Inst. Grain Cult. Dept. 3nt. No. 2: 64-177, 7 graphs, 121 refs. Kiev-Kharkov. ('.Tith a summary in English.) [In Ukrainiaji. Abstract in Eev. Appl. 3nt. (A) 25: 269-270- 1937.1 61. IffilGHT, H. G. 1933. Utilization of fruits and vegetables aided by chemical discoveries. U. S. Dept. Agr. Yerxbook of Agr. 1933: 359- 364. 62. COSTOFF, DOITTCHO 1939. Nicotine and citric J.c, field lacora^ 1935; 1101. 193S. Conparative studies of the effect of certain ganglionic poisons on respiration. J. ?h"siol. ('J. S. S. ?..) 24: £01-17. (In Trench, cl7.; [in T.-O-ssisn. Abstract in Ohen. Acs. 33: 2993. 1939.] 7c. 1!Z1'3HIZCV, S. , es.t 3-r.I>I?.I"I9H, A. A. 1335. All-calcids cf Ar.?.c?.sis a~hvlla . XII. Zxperineats rn the s--nthesis of anacasine and contributions to the chexis- tr;.' of alpha, "beta-cipyridyl. Ser. Deut. Chpn. &esch. 593: 495-499. [Abstract in The-. Acs. 30: 4171. 1936.] 79. , S?.IG-0:--C7ICH, A. , and CIZIIHCT, A. ?. 1934. Alkaloids cf An-ib-^.sis aph:.- 11a . VII, A.nination of anaba- sine and ir-neth"l?nabasine with sodaz:ide. 3er. Deut. Ohen. vJesch. 573: 259-292. [Abstract in Ch^c. Abs. 28: 2358. 1934.] - 44 - eo. aSIGOP.OVICH. A., and 0E3.2I0V, A. P. 1934. Alkaloids of An ?;cas-:s aphylla. IX. Oxidation of methj^l- ?jid benz-o^lan oasine inethiodide. 3er. Seut . Chem. Gesch. 57S: 1393-1402. [Atstract in Cksn. Ats. 28: 6719-6720. 1934.] 81. LOSIX, I., and CHEIfHOV, A. ?. 1934. Alkaloids of Anaoasis aph,ylla. VIII, Sons oxidation produces of anaoasine. 3er. Deut. CheE. C-esch. 673: 1157-1x58. [Abstract in Chen. Afcs. 28: 5826. 1934.] 82. LOSIIC, I., and CHSIIHOY, A. ?. 1934. Oxidation of "benzoylaiia-basine Tith potassiijin permanganate. iiiiai. Jarni. Prom. ITo. 6; 7-3. [Abstract in Chen. Abs. 30: 2196. 1936.] 83. MIZEF.OYA, A. M. 1935. Chenicr.l control of the apple sucker. Plant Prot. fasc. 3: 117. Leningrad. [in P-ussian. Abstract in Pev. Appl. 3nt. (A) 23: S17. 1935.] 84. NAGSL, U. 1931. Dipyr idyls z-or Schadlingsbek.2r/pfuns. Anz. Schad. 7: 137-139. 85. N3LS01], 0. A. 1934- Some physical constants of anabasine. Joirr. Araer. Chem. Soc. 55: 1989-1990. [Abstract in Chem. Abs. 28: 5720. 1934.] 86. l^SVSKII, V. P., USP3i:SKAYA, N. V., and SHAPOSB-IiZCVA, 3. 1937, 3laboration of a control program for the codling moth, G--dia pononella L. (pp. 393-399). Stimmary of the Scientific Eesearch TJork of the Institute of Plant Protection for the Year 1936- Part II. Pests and 3isea.ses of Industrial and Pruit Crops. T:oy. 6vo, pp. 253-444, 18 graphs, 13 diagr., 22 figs., 4 rsfs. Leningrad, Lenin Acad. Agr. Sci. iln F.ussian. Ab- stract in Hev. Appl. Snt . (A) 26: 479. 1958.] 87. ^IST7 J3PS3Y STA'TE AGEICULTUSAL. 3X?3PJ:.3H-T STATION 1935. L^-abasine sulphate.] N. J, 5ta.te Agr. Expt . Sta. Ann. Eept. (1935) 55: 44. - 46 - 83. ITOEimiA, S. S., 1IA5XUZIS7, T., and C32ZH0Y, A. P. 1937. Alkaloids of Anr."basi s a phylla . XIII. The specific rotation of anatasine, depending upon tae liiethods of its isolation iroa the plant, the na.t^ire of the solvent and the concen- tration. Joior. Gen. Chsn. (U. S. S. E.) 7: 951-955. [In Russian. Aostract in Chem. Ahs. 31: 657C. 1937.] 89. O'BITITE, inCEAZL 3DV.APJ:, SIS^SJR 1933. The infra-red adsorption spectra- of certain alkaloids. Jour. Cptica.1 Soc. America 23: 92-100. [Abstract in Chem. Ahs. 27: 2880. 1933.] 90. OIGZHOV, A. ?. 1929. The alkaloids of Anaoasis aphylla . Compt. Eend. 189: 945. [Abstract in Chem. Abs. 24: 1385. 1930.] 91. :.i-^— .£^ 1930. Russian flora a source of new alkaloids. Sull. Kauch.- Issledovs-tel. Khim.-Faria. Inst., 3-4. [Abstract in Chem. Abs. 26: 5599-5700. 1932.] 92, 93. 94. 95. 1934. Investigrtion of certain drug and poisonous plpjits of the U. S. S, E. ^ith respect to their alkaloidal content. Arch. Phr-m-. 272: 673-5-1. [Abstract in Chem. Abs. 28: 5596. 1934.] 1934. Constitution of anaba.sine. Remarks on the conmunica.tion of A. 'Jenusch and P., Scholler: Constitution of anaba- sine. Ber. Pe-it. Chem. C-esch. 67B: 1606. [Abstract in Chem. Abs. 2S: 7258. 1934.] 1936. Recent alkaloidal invesoigations. Bull. Acad. Sci. U. R. S. S. Classe Sci. Math. Nat. Ser. Chim., No. 6: 935-954. (In French, 954-955). [Abstract in Chem. Abs. 31: 5365-. 1937.] 1937. The alkaloids of Anabasis aphylla . XIV. The struct\ire of aphylline and aphyllidine. Jour. Gen. Chem. (U. S. S. R.) 7: 2048-2062. [In Russian. Abstract in Chem. Abs. 32: 572. 1938.] - 45 - 95. and BP.ODSKII, D. A. 1933. The alfeloids of Analjasis aphylla . VI. Hyclxo-en^.tion of ar.aoasine. Jicr. Deut . Chem. Gesch. 5cB: 455-468. [Ab- stract in Chem. Ats. 27: 3217. 1933.] 97. and BHODSKII , D. A. 1933. Hydration of anatasine. Khin. Farm. Pron. 188-190. [At- stract in Chem. Ads. 28: 574^575. 1934.] 98. and I'EWSHIKCY, G. 1931. The alkaloids of Ana."basis aphylla L. I. Ber. Deut. Chen. Gesch. 64B: 265-274. [Abstract in Chem. Ahs. 25: 3347. 1931.] 99. and I£3KSHIK0V, G. 1931. Alkaloids of Anaba-sis aphylla . II. Constitu-tion of ana- basine. Ber. Deut. Gheni. Gesch. 55B: 232-234. [Abstract in Chen. Abs. 26: 2742. 1932.] 100. and IS17SHIK0V, G. 1931. tJber die Alkaloide ron Anabasis aphylla . III. Dber die hochsiedenden Basen. i_Sta,a,tl. Cheniscb-pharinazeut. For sch. -Inst . IIoscott. December 1931.] Ber. Deut. Chem. Gesch. 54: 255. 1931. 101. and ITOFjrn^A, S. S. 1932. Alkaloids of Anabasis aphylla . IV. iJ-ailcyl derivatives of ana.basine , and the alleged occurrence of methylana- basine in' Ana-basis aphylla . Ber. Deut . Chem. Gesch. 55B: 724r-729. [Abstract in Chem. Abs. 25: 3799. 1932.] 102. and NOFuKIKA, S. S. 1932. Alkaloids of Anabasis aphylla L. V. N-arainoanabasine and racemic anabasine. Ber. Deut. Chem. Gesch. 65B; 1126-1130. [Abstract in Chem. Abs. 26: 5097. 1932.] 103. and KOEIOlviA, S. S. 1932. Alkyl derivatives of anabasine from A nabasis aphylla . Khim. Farm. Prom. 1932: 407-411. [Abstract in Chem. Abs. 27: 3477. 1933.] 104. and KOF-KIIIA, S. S. 1933. Aliialoids from Anabasis aphylla. Khim. Farm. Prom. 1933: 109-113. [Abstract in Chem. Abs. 28: 478. 1934.] - 47 - 105. , V.OFZIMA, S. S., and Il^-SIi:C7A, T. 1934. Alkaloids of An:."b q.si s a-ohylla. X. Pteduction of aphvlli- dine. 3sr. ^eut. Oheia. G-esch. 673: 1845-1849. [Abstract in Ch3n. Ats. 29: 1093- 1935. J 106. NOEKirA, S. S., ajid rA-ICSIIIOVA, T. 1934. Alkaloids of Anaoasi s aDnylla . XI. The Hermann degrada.- tion of a-phjxlidine. Ber, Deut. Chein. Gesch. 673: 1974- 1979. [Aostract in Clia:i. Aos. Z3: 1835. 1935.] 107. PA.YLOV, I. F. 1935. Test of carriers of local importaiice in the manufacture of anatadusts. Pl?jat Prot., fasc. 3: 98-102. Lenin- grad. [In 3r.ssian. Atstract in Hev. Appl. 3nt. (A) 23: 614-515. 1935. " 108, 1937. Chemical methods of controlling the i^ea aphid in 1935. Plant Prot. iv'o. 14: 113-115. Leningrad. [In Pussian. Abstract in Pev. Appl. Ent. (A) 26: 355. 1938.] 109. PIYOVAP.OY, V. IvI. , and GUTZSIIAK, 3. 1.1. 1937. L'emploi r'o I'anaoadust dans la, lutte contre les mous- tiques "ilherr-ants. [in P-ussian.J Med. Farasitol. 5 (3): 424-432. rios cor'. ("Tith a summary in i'rench.) [Abstract in Pev. Appl. 3nt . (3) 26: 169.] 110. POTAPAYA (FATAPAYA), Sh. 1936. Study of the species of scales, determination of the area of their distribution in the tea regions and their control, pp. 150-151. Summaries of reports of the Scientific P.esearch Institutes of Plant Protection for the year 1935. Plant Prot., fasc. 11: 149-157. Leningrad. [In Russian. Abstract in Hev. Appl. -int. (A) 25: 580-531. 1937.] 111. PEEIN, N. G. 1938. On the alkaloids in different species of Anabasis. Sovet. Bot. 1933, ^o. S: 114-6. [Inst, of Insecto- fungicides and Fertilizers, IIoscof.] [Abstracted in Herbage ^bs. , vol. 9, Ho. 2: 169. June 1939.] 112. EICHAPDSOH, 0. E. , CBAIG, L. C, pnd i£AI-i S33IlRY , T. P. 1936. Toxic action of nicotines, nornicotines and anabasine upon Aphis rumicis . Jour. Econ. Ent. 29: 850-855. - 48 - 113. D^ONIHR, C. Ci ?iid Sllll^IQ^ai^I , 17. A. 1937. The toxicity of certain insecticides to the chinch "bug. Jour, A^rr. Res. 54: 59-78. [Abstract in P-ev. Appl. 3nt. (A) 25: 456-467.] 114. HOARK, R, C. 1934. Recent developments in insecticide research. Proceed- ings of the ^'ifth R.^xiific Science Congress, Canada, (1933) 5: 3405-3410. 115, 1936. Insecticides and fun^'icides. Ann. Survey Amer. Chem. 10 (1935): 253-279. Hew York. 116. ROEIHSOn, R. 1935. The alfeloids. Ann. Rev. Biochen. 4: 497-518. 117. ROI.LAllOVICH, I. K. 1932. Hicotine, neonicotine and anabasine. (A summary of the literature.) [In Russian,] Plant Prot, No. 1: 51-55. Leningra,d. 118. R0SEi;C-ART-FAI,3L, Y. 1937, 3tude hotanique, chemique et pharmacodjTLaraique de diverges espsces des genres Ana cr.sis et Halor.ylon . Trav. Lat. Hat. I.Ied. Paris, (1937) 28 (3): 125. 119. ROTI.IA}^ M. N. 1957. The effect of ?na,basine on the gaseous exchange in insects. Izv. Kurs. -Prikl. Zool., 1935, 6 (3): 2-14. Leningrad. [in Russian. Abstract in Rev. Appl. Snt. (A) 25: 799. 1937.] 120. RUlXAilTZIlV , LI. 1937. Tests of chemical control measures against the hemp flea "beetle, ^v. 188-189. Notes on and siommaries of the reports of the Scientific Research Institutes of PloJit Protection for the Year 1935. Plant Prot. fasc. 12: 187-191. Leningrad. [In Russir:'Ji. Abstract in Rev. Appl. 3nt. (A) 25: 663. 1937.] 121. SARG-JIN3, K. D. 1933. Pharmacoloa^ of anabasine. IChim. Farm. Prom. 1933: 136- 138. [Abstract in Chem. Abs. 28: 531. 1934.] 122 49 )34. The pharin.'\co3-Og3r of anatasine. Rev. de Phannacol. 3: 32-37: 5er. iiber die G-esam. Phj'-siol. u. "^xpt. Pharmakol. 88; 155. [Abstract in Chen. Ats. 31: 8025. 1937.] 123. SAVC1^:IK0, E. F. 1937. Chief conclusions of the scientific research r'ork of the All-Union Scientific Eese.^xch Institute of Sugar Indus- try for the Year 1935. [Super-P.oy. Bvo , 235 Vl?'^ 6 graphs, 39 figs. Kiev.] Deternination of effective doss^es of anatadusts for the control of "beet aphids, pp. 125-127. [In Russian. Abstract in liev. Appl. Snt . (A) 25: 235. 1958.] 124. 1S35. use of nicotine sulfate and of rjaa":asine sulfate against beet flies. Soviet Sugar 14 (8): 9-11; Ghioie & industrie 39: 752. [Abstract in Chem. Abs. 32: 5148. 1938.] 125. and DZSVALTOVSrIAYA , N. &. 1937. Results of conpara-tive tests on new activators for ajiaba- sine sulpha^te in corabating the beet aphid. Nauch. Zap. Saklia-m. Prom. 14 (3): 34-42, 14 refs. Kiev, [in Russian, Abstract in Rev. Appl. Snt. (A) 26: 237-238. 1938.] 125. and I.:0I3lZHITZIvAYA, 3. H. 1935. The insecticidal properties of nicotine sulphite in com- parison with some other nicotine preparations. Sborn. Rab. Ent. Otd. VIITa [Coll. Horks Ent. Sect. All-Union Inst. I.Iaichorka Industry] pp. 6-30. Kiev. ('.Tith a summar:/ in German.) [In Russian. Abstract in Rev. Appl. Ent. (A) 24: 50-51. 1936.] 127. and RATiTER, Yu. B. 1935. The applica.tion of different preparations of anabasine and lupinine for the control of beet aphids. Kauch. Zap. Saldiarn. Prom. 12 (5-6): 141-157. Kiev. [In Russian. Abstract in Rev. Appl. Snt. (A) 24: 760-761. 1936.] 128. SCHI7JCK:, A. A. 1937. Chemical composition of alkaloids in inter-species hybridi- zation of plants of genus r'icotiana . Bulletin de I'Aca- demie des Sciences de I'U. R. S. S. Classe des Sciences Ilathenatiques et Katurelles. pp. 1693-1708. CTrai;slated from Russian. ) - 50 - 129. S'lBFAIJj, H. H. 1939. The c.ieraistry and toxicology of insecticides, ■.'inneapolis. 3&3 pp. (Anab^isine, p. 262-254.) 130. SIK^L'NIXOVA, Z. S. 1936. Inv9stii;;ation on the chenical control raeasiires for suraner generations of vrooll;'- apple aphid, pp. 284-285. Sumnary of the Scientific Keseajrch "ork of the Institute of Plant Protection for the Year 1935. Roy. 8vo 596 pp. illus. Leningrad, Lenin Acad. Agr. Sci. [In Eussian. Abstract in Piev. Appl. Snt. (A) 25: 151.- 1937.] 131. SKALOY, Yu. Yu. 1934. The applic?,tion of analoasine sv.lfate as insecticide for tolDacco plants. Tabaciina.2'"a Prom. r'o. 6: 23-25. [Aostract in Chem. Acs. 29: 3101. 1935.] 132. SKALOVA, A. &. . and ISlLSBBitl'Ii'SIIII , B. A. 1936. 3xtr?.cts from the reports of the section of tobacco protec- tion of the A. I. llikoyan Crimean Branch of the All-Union Institute of Tcho,cco and Llakhorka Industry for the Years 1930-1935. I. Entomology. Pla^t Prot., fasc. 10: 125-140. Leningrad. L^n Hussian. Abstract in Rev. Appl. 3nt. (A) 25: 401-402. 1937.] 133. Si:iTK, C. R. 1929. Insecticide research develops a promising substitute for nicotine. U. S. Sept. Agr. Yearbook of Agriculture 1928: 388-389. 134. 135. 136. 137, 1931. Feonicotine and isomeric pyridj'-lpiperi dines. Jour. Ajiier. Chem. Soc. 53: 277-283. [Oil, Faint and Drug Reporter 117 (16): 38-c. 1930; Rev. Appl. Ent. (A) 18: 648.' 1930.] 1931. Neonicotine recently found as an alkaloid in Anaba.sis aphylla L. Jour. Scon. 3nt. 24: 1108. 1932. Identity of neonicotine and the a.lkaJLoid anabasine. Jour. Amer. Chem. Soc. 54: 397-399. 1934. Base exchange reactions of bentonite and salts of organic bases. Jo-or. Acier. Chem. Soc. 56: 1561-1563. 138. 132 5i 1935. Occurrence of analDasine in l icotigna glauca G-rah. (Sola- nB.ceae). Jour. Amer . Ghe-n. Soc. 57: 959-960. 1956. Compounds of bentonite vrith organic "bases and process of producing ssune. U. S. Patent 2,033,656 (l.Iarch 10, 1936; appl. July 5, 1934). 14,0. RICHABDSOI'I, C. H. . and 3?3?AFJ), H. H. . • ■ 1930. r^eonicotine and certain other deriv?,tives of the dipyri- dyls as insecticides. Jour. 3con. 3nt. 23: 563-867. 141. :S0K0L0V, A. G. 1935. The fluosilicate nethod for sepai'aticn of anabasine. Xhim. Farm. Prom. 1935, In'o. 3: 152. 142. 1937. Comparative microscopic tests cf anabasine and some plij'sical constpjats. Milrrochenie 23: 147-148. 1937. (Cf. Zerbey, Orinick and VJillard, Cliem. Abs. 31: 4054-4055. 1937.) [in Russian. Abstract in Chera. Abs. 32: 1383. 1938.] 143. and IIRSTOY, A. 3. 1937, Anabasine fluosilicate. Russian patent 51,137, Fay 31, 1937. [In Russian. Abstract in Chem. Abs. 33: 4743. 1939.] 144. SOROGOZHSICAYA, - 1935. Tests of poisons in the control of the cherry sarfly. Plant Prot., fasc. 3: 118. Leningrad. [In Russian. abstract in Rev. Appl. Ent. (A) 23: 618. 1935.] 145. SPlTH, S.. and OSZTIER, F. 1937. Tobacco aJicaloids. X. Synthesis of 1-anabasine and d-anabasine. Ber. Deut. Chein. Oesch. 70B: 70-72. ^Abstract in Chem. Abs. 31: 2605. 1937.] 146. and /3SZTLER, F. 1937. 1-Anatabin, ein neues Tabakalkaloid. XI, Uber Tabalc- Basen. Ber. Dei-.t. Chem. Gesch. 70: 239-243. - 52 - 147. and :'-3SZTL3H, I. 1937. Totacco alkaloids* XI I. OcJbtLrrence of dl-nornicotine , dl-anatabine aixd l-alia'ba^.ine in totacco. Ber. Deut. Chem. Gescli. 70P; 704-709. [Atstract in Chem. Ats. 31: 4330-4331. 19 37. J 148. and KESZTI^IE, I. 1937. TolDacco alltaloids. XIII. Few totiacco "bases. Ber. Deut. CheE. Gesch. 70B: 245C-2454. 1937. [in German. Abstract in Chem. Abs. 32: 1275. 1938.] 149. and I.L^IOLI, L. ' 1936. Tobacco alkaloids. VII. A ner s^mthesis of dl-anabasine . Ber. Deut. Chein. Gesch. 69B: 1G82-10G5. [Abstract in Chem. Abs. 30: 5230. 1936.] 150. STAilDLSY, PAUL C. 1924. Trees and shrubs of Mexico. Contrib. U. S. Nat. Herb. 23 (4): 1278. 151. SUGAK, A. 1938. On the study of pests attacking non-alkaloid lupin. Plant Pro. 16: 96-99. [Abstract in Eev. Appl. Ent. (A) 27: 150-151. .1939.] 152. TJmASOVA, E. L. 1937. The effect of anabasine on the activit^^ of the heart in insects. Izv. ICurs. Prikl. Zool. (1936) 6 (3): 15-24. Leningrad. [in Eussian. Abstract in Eev. Appl. Ent. (A) 25: 799. 1937.] 153. T3M0VSSY, 1.1. P., ICH.HRA, I.I. I . , and ZUlvOV, N. I. 1937. Inheritance of nicotine and anabasine in interspecific hybrids with ITicotiana glauca Grah. Gompt, Rend. Acad. Sci. U. E. S. S. (1937) 17 Tl-2) : 43-45. 154. TOM, 0. 1932. Anabasin wird als Sulfat zur Insekten-vertilgung in der Handel gebracht. Pharmaz. Mh. 13: 137-159. September 1932. 155. miTED STATES DEPARTIISFT OP AGEICULTUPE , BUEEAU OP CHEI.IISTRY AMD SOILS 1934. [Anabasine.] Eeport of the Chief of the Bureau of Chemistry and Soils. U. S. Dept. Agr., Bvor . Chem. and Soils Ann. Eept. 1934, p. 27. - 5S - 156. miTSD STATSS DEPART! S*I? 07 ASRIOIJLTUEG , BuHZAU 0? ZI'TOI'OLCCT ^'D PLAICT 1935. Insecticide invest i-^at ions. Leport cf the Chief of tlie Bijireau of Sntomologj and Plant O.'osj'antine. 'J. S. Dept . Agr., Bur. Snt. and PI. Qroar. Ann. Hept . 1935, p. 63. 157. VA7IL0V, I. F., and IXTOIITDBTOVA, S, I.l. 1935. Silt sti tut ion of lime for soap in solutions of anatasine sulphate. Social Grain Pag. 5 (4): 96-101. Saratov, (-"ith a sunmarv in English.) [In Russian. Aostract in Pev. Appl. Ent. (A) 24: 19-20. 1S36.] 158. I::E1.tuSCH, a., and BILOTITSXI, Ct. 1934. Determination of anal»asine. Eiochem. Ztschr. 270: 15-16. [Ab- stract in Chen. A"bs. 23: 4837. 1934.] 159. and SCHCLLEH, R. 1934. Constitution of anabasine, 3er. Deut. Chen. Oesch, 67E: 1344-1345. [Abstract in Chen. Abs. 23: 5720. 1934.] 160. YOTEEF^, M. A., and aP.IPPIiv, S. '7. 1940. Tests of rotenone, anabasine, nicotine, and other insecticides against the v/ooll;'- apple aphid and the apple aphid. Jour. Econ. Snt. 33 (5): 800-803. 161. ZALKIi^D, M. D. 1932. The effect of anabasine s^alphate upon the beet louse. Aphis fabae. Hauch. Zapiski Tz'olcrovoi Pron. 21-22, 185-189. [Abstract in Chen. Abs. 27: 555. 1933.] 162. ZEEESy, :.I. S., ORrflCK, 1.1. T., and UILIARD, 1,1. L. 1937. Comparative tests of anabasine and its related compounds, its piorification and sone phj-sical constants. Milo-ochenie 21: 171-179. [Abstract in Chen. Abs. 31: 4054-4055. 1937.] 163. ZUK07, II. I. 1939. Inheritance of nicotine and anabasine in interspecific hybrids I^Hcotiana rustica L. x N. glauca Grah. 'Compt. Hend. Acad. Sci. U. P. S. S. (N. S7r22 (3): 115-118. - 54 - I1TD3X TO Il-ISSGTS AGAINST TKIOH AixABASIlME iLf.S ESillT 'lES-KD Species of insect F.efqr ence n u^te: Anasa tristis (Deg.) Anopheles sp. Ar.uraphis roseus (Baker) Apbids Apanteles glomeratus L, Aphis fa'cae Scop. Aphis goss:;pii Glov. Aphis medicaginis ICoch Aphis po3ii Deg. Aphis rvanicis L. 18, 21, 27, ^S, 50, 35, 112, 140 Aphis sair."buci L. Aphis spiraecola Patch Aphis me Hi f era L. Aspidiotus destructor Aspidiotus perniciosus Const. Aulacariim pelargi Beet aphid Beet flies Blatta orientalis L. Blissus leiicopterus (Say) BomlDjoc mori L. Brevicoryne "brassicae (L.) Caliroa limacina F.etz. Carpocapsa pomonella (Tj, ) Ceutorhynchus macul^.-aloa Htst. Chinch ^ougs Chrysoraphalus dictyospermi I.Iorg. Coccids Culex pipiens L. » Culex quincuefasciatus Sa^?- Culex territans Culex sp. Cydia, pomonella (L.). See Carpocapsa pcmoneila (L.) 3phestia kuehniella Zell. 3pilachna varivestis I.Iuls. ^riosoma lanigerum (Hausm.) Suxoa segetura Schiff. G-rapholitha raolesta (Busck) H^rpononieuta padellus malinelir.s Zell. See Hyponomeuta malinellus Zell. Hj'ponomeuta malinellus Zell. Lepidosaphes gloverii (Pack) llacrosiphuE onobrychis Boy. Macro sip hum rosae (L.) 26. 76 109 29 38, 39 152 126, 137, 161 51 151 35, 107. 160 le. 21, 27, 29, 50, 35, 112, 126 27 55 ilO 69. 110 38 123, 125 124 152 113 35 51, 64, 107, 108 144 41, 63, 86 71 113 44 44 16 16 16 109, 127 84 42 130, 160 10 19. 29 107 126 44 108 35 liiiiiiil - 55 - 3 1262 09224 7369 Sp ecies of insect Reference nu EJer Macro siph.-uiii (i.lacrcsiphcGiella) sanocrni (Gill.) See I-'acrosiphum sanbomi (G-ill.) ilacrosiphun sanborni G-il] . 35 Mayetiola destriictcr (Say) See Phytothaga destriiCvOr (Say) uelanophus femvLT-rulDrTim (Deg.) 35 I-Iosquitoes S5, 66 Myzus (Myzoides) persicae (Sulz.)- See Myzus persicae (Suir.) Myzus persicae (Sulz.) 27, 2S , 125, 127, 131, 157 Phlelaotonus spp. 66 Phorodon hunuli (Schr.) 7 Phytophaga destructor (Say) 60 Pieris brassicae L. 45, 119, 152 Pletonus ribesii Scop. -52 Pletonus river si i Scop 119 Popillia japonica lleTTm. 25 Pseudococcus adonidxan (L.) 44 Pseudococcus gahani Green 44 Pseudococcus mar it imus (3hrh..) 44 Psylla mali (Sclim.) 83 Psylliodes attenuata Koch 120 Pteronus ribesii Scop. 45 Pyrrhocoris apterus (L.) 126 Rhopalosiphua rufonaculatum Uilson 35 Stenocarus fuliginosus Mshl. 71 Thrips t abaci Lind. 132 Tjrphlocyba pomaria Mc-Uee 27, 28, 31, 32, 33