STATE PLANT BOARD November 1949 E-7^9 United States Department of Agriculture Agricultural Research Administration Bureau of Entomology and Plant Quarantine PRELIMINARY TESTS OF CHLORINATED BENZAMIDES AS INSECTICIDES By G. T. Bottger and A, P. Yerington, Division of Control Investigations, and S. I. Gertler, Division of Insecticide Investigations One hundred and twenty-eight chlorinated benzamides were tested as insecticides in the laboratory of this Bureau at Anaheim, Calif,, during the period from February 1946 to August 1948, The Division of Insecticide Investigations supplied all samples. All compounds were tested as dusts against at least three speoies of in- sects^ many of the more toxio materials were tested against six or seven species. The following species were used: Alder flea beetle (Altioa ambiens (Lee.)) Armyworm (Cirphis unipunota (Haw.) ) Cabbage aphid (Brevicoryne brassicae (L.)) California oakworm (Phryganidia californioa Pack.) Celery leaf tier (Phlyotaenia rubigalis (Guen.)) Citrus red mite (Paratetranychus citri (McG.)) Green dock beetle (Gastrophysa cyanea Melsh*) Large milkweed bug (Oncopeltus fasoiatus (Dall.)) Pea aphid (llacrosiphum pisi (Kltb.)) Two-spotted spider mite (Tetranyohus bimaculatus Harvey) Variegated cutworm (Peridroma margaritosa (Haw.)) Vegetable weevil (Listroderes obliquus Klug) The armyworm, the celery leaf tier, the large milkweed bug, the pea aphid, and the variegated cutworm were reared in the laboratory; all others were collected in the field. The equipment and methods employed were essentially the same as those described by Swingle, Phillips, and Gahan (1). In most of the tests with coleopterous or lepidopterous larvae 24 insects were used per test, a minimum of 20 milkweed bugs were used, and the number of aphids and mites ranged from around this min- imum to several times the number. The test period was usually 2 days. When received for testing, the samples had been diluted to 25, 10, or 5 percent in pyrophyllite and generally were in good physioal condition for dusting. - 2 - serial a causing mortalities of 75 percent or higher as duata wore applied as apraya to the leaves of five or nc re kinds of plant to determine whet:. tj would injure green foliage. The tpn • contained 25-perce:.t r-nterial applied at the rate of 6 pcunda per 100 gallons of water to green foliage of plants grow ier natural oonditions. The results of the testa with insecticides of known value :nst certain insectB, made for com* arc:*. ive : -rposes, are prer> ted in table 1. Data on 27 compounds that caused greater than 74 percent mortal- ity to one or more species of insects in dust tests are shown in table 2. Of these materials 20 were effective I e rwo-epc*- ted spider mite. On the basis of the number of species affected, the four mc toxic compounds appear to be j^-chlorc-N, N- :. isopro: ^ice, 3,4- dichloro-K,N-diisopropylbenramide, 3,4-dichloro-N, I - :a- mide, and 2-phenylhydrazide-o-chlorobenzoio acid. The first throo compounds named were effective both as contact and as stor.ach poisons, but 2-phe: .. razide-o-chlorober.zoic acid was not effective as a contact poison against the insects tested. appreciable injury to foliage resulted from spray applications of any of the four compounds. Compounds reported in table 2 that did shew moderate toxicity to green foliage of one or more kinds of plants « re N'-amyl-^,4-dichlorobenzamide, 2,4-dichloro-N-etLvlbenramide, and 2,4- dichloro-",N-dipropylbenzamide. Table 3 presents results of tests against varices inaectr 29 compounds that gave kills between 25 and 74 percent. However, the only compounds that caused mortalities of 60 :.t or higher were 3,4-dichlorc— N-benzylbenzami de, p-chloro-?.'-£ec-r.exyl: • :», 2-phonylhydrazide-3,4-dichlorobenzoic acid, and ^hlorc 1- piperidine a,;ainst the two-spotted spider mite, 2-phen -s.zide-r- chlorober. zoic acid against the celery leaf tier, and 2' -etra- chlorobenzanilide Against the pea aphid. The compounds that oaused less than I -ent mortality of the species against which they were tested are listed in table 4. Literature Cited (l) , .:., Phillips, a.v.., and Jahan, J... 1941. Laboratory test:: natural ■ -".hetio organ: .:. * . a g - 3 - r-l rH , 5? 0 In 1 1 1 1 1 1 • » IO CO l> t- OK) IO O Oi o» ! CO I> f- CO •H I T3 © r-l ^ U 0H n O i © © -P hOOH. 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CM a © ... © ~ i o 1 » i •J r-t - i ■ -i E i 3 i rH • X e> 1 c - - 1 1 • '• •r« - 15 - Table 4* - - Chlorinated benzamides that were found to be practioally nontoxic, killing less than 25 percent of insects fed dusted foliage Compound Inseot Stage Percent Anthranilio aoid, N- (2,4-diohloro- benzoyl)- Benzandde, S-amyl- 25 o-chloro- Benzamide, N-amyl- 25 £-chloro- Benzamide, N-amyl« 2,4-dichloro- Benzamide, N-benzyl- 25 jj>-chloro- Benzamide, N-benzyl- 2,4-dichloro- Benzamide, N- sec-butyl- 25 o-chloro- Benzamide, N-butyl- 25 p-chloro— Benzamide, N- sec-butyl- 25 jj>-chloro- Benzamide, N-butyl- 2,4-dichloro- Armyworm Celery leaf tier Large milkweed bug Pea aphid Two-spotted spider mite Arraywora Celery leaf tier Large milkweed bug Two-spotted spider mite Celery leaf tier Pea aphid Two-spotted spider mite Celery leaf tier Pea aphid Two-spotted spider mite Celery leaf tier Pea aphid Two-spotted spider mite Celery leaf tier Pea aphid Two-spotted spider mite Armyworm Celery leaf tier Variegated cutworm Celery leaf tier Pea aphid Two-spotted spider mite Celery leaf tier Pea aphid Two-spotted spider mite Celery leaf tier Pea aphid Two-spotted spider mite Third instar do* Third-instar nymphs 2-day-old nymphs Nymphs and adults Fourth instar do. Third-instar nymphs Nymphs and adults Third instar nymphs 2-day-old nymphs Nymphs and adults Fourth instar 2-day old nymphs Nymphs and adults Fourth instar 2-day-old nymphs Nymphs and adults Fourth instar 2-day-old nymphs Nymphs and adults Fourth instar do* do* Fourth instar 2-day-old nymphs Nymphs and adults Fourth instar 2-day-old nymphs Nymphs and adults Fourth instar 2-day-old nymphs Nymphs and adults - 16 - Table 4. - - (Continued) lampoond Du ■ o t Sta^e Percent Benzamide, N-sec-butyl- 2,4-dichloro- Benzamide, p_-chloro-N-2- 25 bicyclohexyl- Benzamide, p-ohloro-N- 25 cyolohexyl- Benzamide, p-chloro— N- 25 heptyl- Benzamide, p_-ohloro-N- 25 propyl- Benzamide, N,N-dibenzyl- 25 o-ohloro- Benzamide, N,N-dibenzyl- 25 p_-ohloro- Benzamide, N,N-dibenzyl- 25 3,4-dichloro- Henzaniide, N,N-dibutyl- 2,4-dichloro- Benzamide, 2,4-dlohloro-N- Benzaaide, 2,4-diohlon - N- oyoloheiTl- lanido, .' ,4-d ichloro-N- oyclo-hoxyl- Celery leaf Poa aphid Two- spotted Celery leaf Pea aphid Two-spotted Celery leaf Pea aphid Two-epotted Celery leaf Pea aphid Two-spotted Celery leaf Pea aphid Two-spotted Celery leaf Pea aphid Two-spotted Celery leaf Pea aphid Two-epotted Celery lea: Pea aphid Two-spotted Celery leaf Pea aphid Two-spotted Celery loaf Pea aphid Two-spotted Celery leaf Pea aphid Two-spot' ery leaf Pea aphid Two-s tier spider mite tier spider Kite tier spider rite tier spider mite tier spider Kite tier spider mite tier spider mite tier spider mite tier spider mite tier 1st mite tier «r mite ■ Fourth instar 2-day-old nym lymphs and ad Fourth instar 2-day-old nymphs lymphs and *d Fourth instar 2-day-old nymphs Symphs and ac Fourth instar 2-day— old nymphs Nymphs and adults Fourth instar 2- day— old nymphs Nymphs ana adults Fourth instar 2-day-old nymphs Nymphs and adults Fourth instar 2-day-old nytr Nymphs and adults -d instar 2-day-old nym: sm Nymphs Had adults Fourth instar 2-day— old nyr Nymphs and adults Third instar Ltl Nymp - instar - Nymphs and * Fa *r 2-dft - Nymphs and ad - 17 - Table* 4 - - (Continued) Compound Inseot Stage Peroent Benz amide, 2,4-dichloro- 5 N-isobutyl- Benzamide, 3,4-dichloro-N- 25 isobutyl- Benzanilide, 4,-benzoyl-4- 25 chloro- Benzanilide, 2,-bramo- 2,4-dichloro- Benzanilide, 4,-bromo- 2-ohloro- Benzanilide, 2-chloro- Benzanilide, 4-chloro- 25 Benzanilide, 4,-bromo- 25 4-chloro- Benzanilide, 4'-bromO' 2,4-dichloro- Benzanilide, 4f-bromo- 3,4-dichloro- 25 Benzanilide, 2-chloro-2t- 25 nitro- 25 Benzanilide, 4-chloro-2t- 25 nitro- Celery leaf tier Pea aphid Two-spotted spider mite Cabbage aphid Celery leaf tier Two-spotted spider mite Celery leaf tier Pea aphid Two-spotted spider mite Celery leaf tier Pea aphid Two- spotted spider mite Celery leaf tier Pea aphid Two- spotted spider mite Celery leaf tier Pea aphid Two-spotted spider mite Celery leaf tier Pea aphid Two -spotted spider mite Celery leaf tier Pea aphid Two-spotted spider mite Celery leaf tier Pea aphid Two-spotted spider mite Celery leaf tier Pea aphid Two-spotted spider mite Celery leaf tier Pea aphid Two-spotted spider mite Celery leaf tier Pea aphid Two-spotted spider mite Fourth instar 2-day- old nymphs Nymphs and adults do. Fourth instar Nymphs and adults Fourth instar 2- day-old nymphs Nymphs and adults Third instar 2-day-old nymphs Nymphs and adults Fourth instar Nymphs Nymphs and adults Fourth instar 2-day-old nymphs All stages Third instar Adult Nymphs Fourth instar 2-day-old nymphs Nymphs and adults Third instar Nymphs Nymphs and adults Fourth instar Nymphs Nymphs and adults Fourth instar 2-day-old nymphs Nymphs and adults Fourth instar 2-day-old nymphs Nymphs and adults - 18 - L< ■ . - - Btinued] Percent Benranilide, -i-chloro- 25 S'-nitro- r.enranilide, 4-chloro- 25 4'-nitro- 3enzani3ide, 2,2f- dichloro- Benzanilide, 2,3- cichloro- .-anilide, 2',' dichlorc— Benzanilide, 2,4- dichloro- 25 25 25 Eenranilide, 2,4- dichloro-2'-nitro- Benzanilide, 2,4- di chin ro-3' -nit ro- Bemeuilide, 2,4-dichloro- 4'-uitro- benzanilide, : ,4-'ichlorc— '-phpayUio- Celery leaf tier Pea Two-«pctted spider Celery leaf tier Pea aphid ■j-spotted spider mite Celery leaf ti» Pea apt Two- Grotted 6pider mite Celery leaf ti« Pea aphid Two- cpotred spider mite Celery leaf tier Pea aphic TwD-cpotted spider mite AnnyTwonL Celery leaf ti. Green dock beetle Large milkwe«d bug Pea aphid Two- s^-ottod 8pider mite Celery- leal' ti» aphid Two-cpottod spider mite Celery leu Two-spot r mite Celery leaf tier Two-s; .der mita Araryworii "n lie tie Large milkweed I Pea der m Pc . r 2-d'.. - . Kymxhs and adults Fourth 2-day-old nyi and adults Third ir-star Hyupha I and adults rth in star pha V.~phs and adults Fourth inetar 2-daY-cld ::yr Nymp.'.s and adults Third inatar do. rth ins tar Thi rd-inel ■ r nymphs 2-du; . Lta :nfitar - and adults ar 2-dayc I ta Thir ter . - 'Id nymph* I and adults rd instar . tax apba - Nymphs and adult« - 19 - Table 4. - - (Continued) Compound Insect Stage Benzanilide, 3*,4- dichloro- Benzanilide, 4,4*- dichloro- Benzanilide, 3,4- dichloro-41 -nitre- Percent 25 25 5 Benzanilide, 2,4-dichloro- 5 2,-phenyl- Benzanilide, 2,2*,4,5*« tetrachloro- Bonzanilide, 2,2»,4- triohloro- Benzanilide, 2,2*, 5«- 25 trlchloro- Benzanilide, 2» ,3,4- 25 triohloro- Benzanilide, 2,3»,4- trioixloro- Benzanilide, 2,4,4'- trichlorc— Benzanilide, 2,J,4,5t- 25 trichloro- 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 Celery leaf tier Green dock beetle Large milkweed bug Pea aphid Two-spotted spider mite Celery leaf Pea aphid Two-spotted Celery leaf Pea aphid Two- spotted Celery leaf Pea aphid Two-spotted Celery leaf S'ea aphid Two-spotted Celery leaf Pea aphid Two- spotted tier spider mite tier spider mite tier spider mite tier spider mite tier spider mite Third instar do. Fourth instar Third-instar nymphs 2-day-old nymph6 Nymphs and adults Third instar 2-day-old nymphs Nymphs and adults Third instar 2-day-old nymphs Nymphs and adults Fourth instar Nymphs Nymphs and adults Third instar 2-day-old nymphs Nymphs and adults Third-instar 2-day-old nymphs Nymphs and adults Celery leaf tier Third 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 kbit 4. - - (CoriMnaedj - 20 - Compound Inaect Stage Percent Benzanilide, 3,3',4- trichloro- 25 o-Eenraniaide, 2-chloro- 25 r-Benxar.iaide, 2-chloro- 25 ;.— Benzaniaide, 4-chloro— 25 o-Benzaniside, 2,4- dichloro— D-Eenzaniaide, 3,4- dichloro- Benzoic acid, 2,4- 5 dichloro-, 2-phenylhydra- de o-Benzotoluide, 2-chloro- 25 p-Benzotoluide, 2-chloro- 25 m-Benzotoluide, 4-chloro- 25 zototuide, 4-chloro 25 Celery leaf tier Pea apnid Two-spotted ap icier mite Celery leaf tier Pea aphid Two-apotted apider mite Celery leaf tier Pea aphid Two-epotted spider mite Celery leaf tier Pea aphid Two-erotted spider mite Variegated cutworm Celery leaf tier Pea aphid Two-apotted apider mite Celery leaf tier Pea aphid Two-apottod apider mite Celery leaf tier Pea aphid Two-apotted apider mite Celery leaf tier Pea aphid Two-apotted apider mite Celery leaf ti' Pea aphid Two-Bpotted apider mite Celery leaf tier Pee aphid Two-Bpotted -r mite Celery leaf tier Pea aphid > ec ider mite Third ir.fftar 2 -day—ola nymph* Nympha and adulti Fourth inatar 2-day-old nym I • Ifympha and adulti Fourth inatar lympha tfymphe and adulti Fourth inrtar 2-day-old nymphi Hyaphs and adulta Third inatar do. Adulta Vympha and adulta Fourth inatar 2-day-old nympha Kympha and adulta Fourth inatar 2-day-old nyr. I and a iulta Fourth inatar Nympha I and adulti Fourth inatar Nymphi Hympha end adulti Fourth in? tar 2 -day -old nye; Hyarha and adulta irth ir.star 2- dr. Nymphs and adulta o, 4-chlt : 25 loaf tier Pea aphid Two-r. ;-der mite h imtar 18 and ar. - 21 - Table 4. - - (Continued) Compound Insect Stage m-Benzotoluide, " 2,4-dichloro- p_-Benzotoluidet 2,4- dichloro- Morpholine, 4- (pj-chlorobenzoyl)- Morpholine, 2,4- dichlorobenzoyl- Morpholine, 3,4- dichlorobenzoyl- Peroent 25 25 Celery leaf Pea aphid Two- spotted Celery leaf Pea aphid Two-spotted Celery leaf Pea aphid Tmo-spotted Celery leaf Pea aphid Two-spotted Celery leaf Pea aphid Two- spotted tier spider mite tier spider mite tier spider mite tier spider mite tier spider mite Third ins tar Adults Nymphs and adults Third instar Adults Nymphs and adults Fourth instar Nymphs Nymphs and adults Fourth instar 2 -day- old nymphs Nymphs and adults Third instar 2-d ay-old nymphs Nymphs and adults 3 1262 09227 9800