. IV X STATE BOARD November 1951 E-826 United States Department of Agriculture Agricultural Research Administration Bureau of Entomology and Plant Quarantine PRELIMINARY TESTS OF SYNTHETIC ORGANIC COMPOUNDS AS INSECTICIDES. PART VII By G T. Bottger and A. P. Yerington, Division of Stored Product Insect Invest igationa^' and S. I Gertler, Division of Insecticide Investigations 1/ This paper reports a continuation of preliminary tests with miscel- laneous synthetic organic compounds as insecticides that were conducted at the Anaheim, Calif., laboratory of this Bureau. The results include those obtained from 95 compounds not previously reported, 86 of which were tested from March 19^9 to June 1950, 9 in 19^7, and 1 in 1948. The Division of Insecticide Investigations supplied all samples. Of these compounds 90 were tested as dusts and 5 as sprays or dips against at least 3 species of insects; many of the more toxic materials were tested against 8 species. The following species were used: Alder flea "beetle (Altica ambiens (Lee.)) Armyworm (Pseudaletia unipuncta (Haw. ) ) Celery leaf tier (Phlycteenia ruhigalis (Guen. )) Citrus red mite ( Paratetranychus citri (McG. )) Green dock beetle (Gastrophysa cyanea Melsh.) Large milkweed hug (Oncopeltus fasciatus (Dall. )) Mediterranean flour moth (Ephestia kuhniella Zell. ) Pea aphid ( Macros i phum pi si (Kith. )T~ Two-spotted spider mi te ( Tetranychus himaculatus Harvey) The alder flea beetle, the green dock beetle, and the two-spotted spider mite were collected in the field; all others were reared in the laboratory. The materials to be tested were dusted or sprayed on foliage and the foliage was placed in petri dishes with larvae of the coleopterous and lepidopterous insects. Aphids were dusted or sprayed either on or removed from the plant, and were confined during the test period on potted Windsor bean plants in cloth-capped glass battery Jars 7 inches in diameter. The two-spotted spider mites were always dusted while on castor bean leaves and were then kept in battery Jars. Both active and egg stages of the citrus mite were treated by dipping infested oranges into the insecticide. Milkweed bugs were dusted or sprayed while confined in 9-cm. crystallizing dishes in which they were retained during the test period. 1/ Formerly the Division of Control Investigation! -2- In the teste with coleopterous or lepidopterous insects 2k larvae were used per test; a minimum of 20 milkweed hugs were used, and the number of aphids and mites ranged from around this minimum to several times this number. The test period ranged from 1 to 3 days for the active stages of the insects and from 5 to 8 days for citrus mite eggs. When received for testing, 23 of the dust samples had "been diluted to 5 or 10 percent in pyrophyllite, and generally were in good physical condition for dusting. Compounds tested at lower concentrations were also diluted with pyrophyllite, except tetra-n- propyl dithiopyrophosphate, which was "both originally and further diluted with fuller's earth. Materials causing mortalities of 75 percent or higher were tested against the same insects at reduced concentrations and were also applied as sprays to leaves of five or more kinds of plants to determine their toxicity to green foliage. For comparative purposes tests were made with "benzene hexachlorlde; gamma, "benzene hexachlorlde; l,l,l-trichloro-2,2-bis(p_-chlorophenyl)ethane (DDT); bis (p_-chlorophenoxy)me thane; 4,6-dinitro-o-cresol; and 0,0-diethyl 0-p_-nitrophenyl thiophosphate (parathion). The results of the dust tests with these standards are shown in tahle 1. Data on 22 organic compounds that caused greater than 7^ percent mortality to one or more species of insects in dust tests are shown in table 2. Of these compounds 19 were effective against the two-spotted spider mite, 13 against the armyworm, and 7 against the green dock beetle. Not more than 2 compounds were effective against any of the other h species, tested. 2,5-Di-tert-butyl-p_-quinone (No. 19)2-' was effective against 5 of the 6 species against which it was tested. It is noteworthy that this compound was effective against k orders of insects and 1 spider mite . No injury resulted when green foliage of bean, collard, corn, pumpkin, and tomato was sprayed with a suspension of this material. 2-Cyclohexyl-4,6-dlnitrophenyl 2,4-dlnitrophenyl ether (No. 11) was effective against the armyworm, the celery leaf tier, the green dock beetle, and the two-spotted spider mite, but caused severe injury to green foliage of beans, chard, and corn, and moderate injury to collard, pepper, pumpkin, and tomato. 2-Chloro-U,6-dlnitrophenol (No. 17) was effective against the pea aphid and the two-spotted spider mite, and 2,l+-dinltrophenyl ^-methylcyclohexyl ether (No. 8) was effective against the armyworm, the green dock beetle, and the two-spotted spider mite. The last compound caused only slight injury to collard and corn plants and moderate injury to beans. It did not injury chard, pepper, pumpkin, and tomato plants. £/ Compounds may be found in the tables by number. -3- Results with 5 new compounds and parathlon tested as sprays or dips are reported in table 3. The ethyl ester of alpha- (die thy lphosphory)- ■cetoacetic acid (No.l) was the most toxic and cyclohexyl diethyl ester of phosphoric add (No 5) the second most tox'c to the insects tested. Although dibutyl jD-nitrotoluenephosphonic acid (No. 6) was toxic to the smallest number of species, it was effective against active stages of the citrue mite and late nymphal stages of the pea aphid. None of these com- pounds caused injury to green foliage when applied at a concentration of 0.2 percent. These new materials did not compare favorably with parathlon. The 65 compounds that caused less than 75-P©**cent mortality of the species tested are listed In table h. 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Fifth instar 2-day-old nymphs Nymphs and adults -20- Table 4. — (Continued) Number Compound Insect Stage (35) (36) (37) (38) (39) (40) (41) (42) Ether, 2, 4-dichloro phenyl Armyworm Third ins tar 2,4-dinitrophenyl Celery leaf tier do. Pea aphid 2-day-old nymphs Two- spotted spider mite Nymphs and adults Ether, p-( alpha, alpha- dimethylbenzyl) phenyl 2, 4-dinitrophenyl Ether, 2,4-dinitro- phenyl 1-naphthyl Ether, 2,4-dinitro- phenyl 2-naphthyl Ether, 2,4-dinitro- phenyl m-nitrophenyl Ether, 2,4-dinitro- phenyl o-nitrophenyl Ether, 2,4-dinitro- phenyl p-nitrophenyl Ether, 2,4-dinitro- phenyl phenyl Armyworm Third ins tar Celery leaf tier do. Mediterranean flour moth Fifth instar Pea aphid 2-day-old nymphs Two-spotted spider mite Nymphs and adults Armyworm Third instar Celery leaf tier do. Pea aphid 2-day-old nymphs Two- spotted spider mite Nymphs and adults Armyworm Celery leaf tier Pea aphid Two-spotted spider mite Third instar do. 2-day-old nymphs Nymphs and adults Armyworm Third instar Celery leaf tier do. Pea aphid 2-day-old nymphs Two-spotted spider mite Nymphs and adults Armyworm Third instar Celery leaf tier do. Pea aphid 2-day-old nymphs Tro-spotted spider mite Nymphs and adults Armyworm Third instar Celery leaf tier do. Mediterranean flour iroth Fifth instar Pea aphid 2-day-old nymphs Two-spotted spider mite Nymphs and adults Armyworm !£hird instar Celery leaf tier do. Pea aphid 2-day-old nymphs Two-spotted spider mite Nymphs and adults Table 4.— (Continued) -21- Number Compound Insect Stage (43) (44) (45) (46) (47) (48) (49) (50) Ether, 2,4-dinitro- phenyl o-tolyl Ether, 2,4-dinitro- phenyl p-tolyl Ether, 2,4-dinitrophenyl 2,4, 6-tri chlor ophenyl Ether, 4-tert-butyl- 2-chlorophenyl 2,4-dinitrophenyl 0-Ethyl 0, 0-bi s (p_-nit ro- phenyl) thiophosphate Glycine, N-(2,4- di nit r ophenyl ) - Hydroquinone, 2,5-di- tert-butyl- Naphthalene, 1,5-bis- ( 2 , 4-dinitrophenoxy) ■ (51) 1,5-Naphthalenediol Armyworm Third ins tar Celery leaf tier do. Green dock beetle Fourth instar Pea aphid 2-day-old nymphs Two-spotted spider mite Nymphs and adults Armyworm Third instar Celery leaf tier do. Pea aphid 2-day-old nymphs Two- spotted spider mite Nymphs and adults Armyworm Third instar Celery leaf tier do. Pea aphid 2-day-old nymphs Two-spotted spider mite Nymphs and adult a Armyworm Fourth instar Celery leaf tier Third instar Pea aphid 2-day-old nymphs Two-spotted spider mite Nymphs and adults Armyworm Fourth instar Celery leaf tier Third instar Pea aphid 2-day-old nymphs Two-spotted spider mite Nymphs and adults Armyworm Third instar Pea aphid 3-day-old nymphs Two-spotted spider mite Nymphs and adults Armyworm Third and fourth instar s Celery leaf tier Third instar Pea aphid 2-day-dd nymphs Two- spotted spider mite Nymphs and adults Armyworm Third instar Celery leaf tier do. Pea aphid 8-day-old nymphs Two-spotted spider mite Nymphs and adults Armyworm Third and fourth instars Celery leaf tier Third instar Pea aphid 2-day-old nymphs Two-spotted spider mite Nymphs and adults Table 4. — (Continued) -22- Number Compound I ns e ct Stage (52) p-Nitrophenyl phosphate 2/ (53) Phenol, o-(anisylidene- amino)- (54) Phenol, o-benzylidene- amino- (55) Phenol, p-butylamino- (56) Phenol, o-(o-chloro- benzylideneamino)- (57) Phenol, o-(p-chloro- benzylideneamino) ■ (58) Phenol, o-(2,4-dinitro- anilino)- (59) Phenol, jp-(2,4-dinitro- anilino)- (60) Phenol, p-methoxy- Celery leaf tier Pea aphid Two- spotted spider Armyworm Celery leaf tier Pea aphid Two-spotted spider Armywo im Celery leaf tier Pea aphid Two-spotted spider Armyworm Celery leaf tier Pea aphid Two-spotted spider Armyworm Celery leaf tier Pea aphid Two-spotted spider Armyworm Celery leaf tier Pea aphid Two-spotted spider Armyworm Celery leaf tier Pea aphid Two-spotted spider Armyworm Celery leaf tier Pea aphid Two-spotted spider Armyworm Celery leaf tier Pea aphid Two-spotted spider Fourth instar 2-day-old nymphs mite Nymphs and adults Third instar do. 3-day-old nymphs mite Nymphs and adults Third instar do. 3-day-old nymphs mite Nymphs and adults Third instar do. 3-day-old nymphs mite Nymphs and adults Third instar do* 3-day-old nymphs mitesNymphs and adults Third instar do. 3-day-old nymphs mite Nymphs and adults Third instar do. 3-day-old nymphs mite Nymphs and adults Third instar do. 3-day-old nymphs mite Nymphs and adults Third instar do. 2-day-old nymphs mite Nymphs and adults l/ Strength 5 percent. Table 4, — (Continued) -2 3- Uumber C ompound Insect Stage (61) p-Quinone, 2,3,5-tri* chloro-6-phenyl- (62) p-Toluenesulfonic acid, o-cyclohexyl-4, 6-dini* trophenyl ester 1/ (63) p-Toluene sulfonic acid, 4, 6-dinit ro-o-tolyl ester \J (64) p-Toluene sulfonic acid, 2,4-dinitrophenyl ester \J (65) m-Toluic acid, 2-(2,4- dinitrophenoxy) - Armyworm Third instar Celery leaf tier do. Pea aphid 3-day-old nymphs Two-spotted spider mite Nymphs and adults Celery leaf tier Fourth instar Pea aphid 2- day-old nymphs Two- spotted spider mite Nymphs and adults Celery leaf tier Fourth instar Pea aphid 2-day-old nymphs Two-spotted spider mite Nymphs and adults Celery leaf tier Fourth instar Pea aphid 2-day-old nymphs Two- spotted spider mite Nymphs and adults Armyworm Third instar Celery leaf tier do» Pea aphid 3-day-old nymphs Two- spotted spider mite Nymphs and adults \J Strength 5 percent. 3 1262 09239 6091