May 1953 E-859 LIBRARY STATE PLANT ^AR(5?ited States Department of Agriculture Agricultural Research Administration Bureau of Entomology and Plant Quarantine PRELIMINARY TESTS OF SOME ESTERS OF ACETIC ACID AS INSECTICIDES By G. T. Bottger, A. P. Yerington, and S. I. Gertler, Division of Insecticide Investigations Eighty-five esters of aoetic acid were tested as insecticides in the laboratory of this Bureau at Anaheim, Calif,, from July 1950 through January 1952. All the compounds were acetic aoid esters of phenols, of compounds having a phenolic group besides other significant groups, or of aromatic or oycloaliphatic alcohols. Most of them were prepared by reacting the phenol or alcohol with acetio anhydride, under suitable con- ditions. The compounds were all purified by distillation or crystalli- zation, depending on their physical condition. The samples were prepared at the Beltsville, Md., laboratory, either as 10-percent dusts in pyrophyl- lite or as pure materials. All compounds were tested against three or more species of insects and one spider mite. The following species were usedi Alder flea beetle (Altica ambiens (Leo.)) Armyworm (Pseudaletia unipuncta (Haw.)) Celery leaf tier (Phlyc taenia rubigalis (Guen.)) Citrus red mite (Paratetranychus citri (McG,)) Large milkweed bug (Oncopeltus fasoiatus (Dall.)) Pea aphid (Macrosiphum pisi (Harris)) Two- spotted spider mite (Tetranychus bimaculatus Harvey) The armyworm, the celery leaf tier, the large milkweed bug, and the pea aphid were reared in the laboratory; all others were collected in the field. Dustable materials were applied either in a settling chamber or by means of a vacuum-type duster. For each test made with the settling cham- ber, a sample of the deposit was weighed and recorded as micrograms per square centimeter of surface dusted. In tests made with the vacuum chamber 1 gram of each sample to be tested was dispersed by atmospheric pressure. Materials prepared as 10-percent dusts, but which were not dustable because of their physical condition, were made into water sprays or dips. The pure materials were tested in acetone sprays or dips. In dust tests against the alder flea beetle, the armyworm, and the celery leaf tier, the materials were applied to both surfaces of leaves, or sections of leaves, of their respective food plants. In spray tests the leaves were thoroughly sprayed, allowed to dry, and then cut into sec- tions, if necessary. In both tests the treated leaves were fed to third- or f ourth-instar larvae in petri dishes. Mortality counts were made ap- - 2 - innately 46 hours aft' . Third" Of .tur I of the large milkweed bu^ were placed in glass orystalliting dishes and a; rayed or dusted until the dorsal surface was t ccver< treated food and water were supplied a 2-day test period. Adult aphide reared on Windsor bean plants were dipped, s: raj I dusted while on a leaf removed frost the infected pla:.t. A treat- ment the leaves wort LftOWd on uninfected potted Windsor bea: Mortality counts were usually made approximately 24 hcurs after treatee: . ; th active stapes and eggs of the citrus mite were treated while on oranges and were left tc feed or develop on the fruit dur ■ 2- and 5-day test periods of their respective stages. The two-spotted spider mites were sprayed or dusted whi'e c bean leaves. The 3 terns of these leaves were kept in water and the mi-es allowed to remain on them during a 2- to 3-day test peri In the tests with coleopterous or lepidopterous larvae 24 to 30 were used per te6t; 20 milkweed bugs were used; the number of aphids averar?" 38, the citrus mite adults 29 and eggs 51, and the two-spotted mite 90. Acetates causing mo;* :es of 7C percent or as dusts, r cr dips were applied as water sprays to the leaves of ^e of t. following plants: I Ley, bean, beets, oi rd, ccllard, c<. oats, peas, pepper, pumpkin, and tomatc . he exoeptio:. chlorophenyl aoetate, which was tested as a concentre- of on. percent, the sprays contained 1 fercent of the active in^redie: I were . i ed until there was run-off to foliage of plants growing under nat - ral conditions. The results of tests with insecticides of lenowr. value against cer- D insects, made for comparative let, are presented in tables 1 2. Da' | n-.tatos that caused BOrtalitiei of I .er of one or more species of insects in s 5 a-e shown '. e 3. Of these materials 16 were found to be effective against the armywonc, 3 against thn citrus mite, 8 against the larrc Bilk weed bu. . t the pea aphid, and 43 ara;nst the two- 3 acetates were tested against the oi t rus mite anc * ir r. All acetates were tested a tlnit the • larpe milkweed bur, the pea aphid, and the tw - • t.ed m: On the basis of mortalities to the rem wa* • rays c: * •t.ates are as follows! - 3 - o-Cresol, 4-tert-butyl- Cyclohexanol, 2-phenyl- Phenol, 2-bromo-4-tert-butyl- o-cyclohexyl- p_-i sop ropy 1- 4-tert-butyl-2-chloro- x,x-di-tert-amyl- 3,4-Xylenol The most effective miticides appearing in table 3 are pentachloro- phenyl aoetate and 2-cyclohexyl-4,6-dinitrophenyl acetate. On the basis of types of insects used, i.e., chewing or sucking, 25 of the 27 acetates that caused greater than 74 percent mortality acted as contact insecticides. 2-tert-Butyl-6-isopropylphenyl acetate and 6-amyl- m-tolyl acetate acted only as stomach poisons. A 1-percent spray of pen- tachlorophenyl acetate caused severe injury to chard foliage. The same spray caused moderate injury to barley, beets, and peas. On the basis of mortalities to the greatest number of species re- sulting from acetone sprays of 5-percent concentration or lower, the most promising materials are 4-cyclohexylcyclohexyl acetate and 2-cyclohexyl- oyclohexyl acetate. Data on 20 acetates that caused more than 74 percent mortality of one or more species of insects in dust tests are shown in table 4. Of these materials 1 was found to be effective against the armywonn, 1 against the pea aphid, and all of them against the two-spotted spider mite. On the basis of greatest number of species killed, the most promising materials found in this table are 2,3,4,6-tetrachlorophenyl acetate and 2,4-dichlorophenyl acetate. The most effective miticides in table 4 are 2-cyclohexyl-4,6-dinitro- phenyl acetate, pentachlorophenyl acetate, and pentabromophenyl acetate. Compounds in table 4 that oaused plant injury include pentachloro- phenyl acetate, already reported in table 3. 4-Biphenylyl acetate and alpha-phenyl-p-tolyl acetate caused slight foliage injury to collard and peas. o_-Cyclohexylphenyl acetate caused severe foliage injury to collard and moderate injury to peas. Pea foliage also suffered severe injury from a 1-percent 2,3,4,6-tetrachlorophenyl acetate spray. Table 5 presents results of tests with 24 dusts that killed less than 75 percent of the insects. The highest mortalities were caused by p_-bromophenyl acetate, p-chlorophenyl acetate, eugenol acetate, o-hydroxy- propiophenone acetate, and 2-naphthyl acetate. Results of tests with 4 sprays that killed less than 75 percent of the insects are shown in table 6. 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