July  1947  E-730 
 
 LIBRARY 
 STATE  P1'  ANT  BOARD  ^tti'*'e<i  States  Department  of  Agriculture 
 
 Agricultural  Research  Administration 
 Bureau  of  Entomology  and  Plant  Quarantine 
 
 DEVELOPMENTAL  TESTS  OF  SYNTHETIC  ORGANIC  COMPOUNDS 
 AS  INSECTICIDES.  PART  I 
 
 M.  C.  Swingle,  J.  B.  Gahan,  and  A.  M.  Phillips,  1/ 
 Division  of  Control  Investigations  2/ 
 
 In  two  previous  papers  (E-621,  1944.;  E-634,  1945)  the  authors  sum- 
 marized the  results  of  certain  preliminary  insecticide  tests  conducted 
 on  979  synthetic  organic  compounds.  The  tests  were  made  on  20  species 
 of  insects  at  the  insecticide-testing-  laboratory  of  the  Bureau  of 
 Entomology  and  Plant  Quarantine  at  Sanford,  Fla.  Those  tests  were  all 
 designed  to  furnish  preliminary  evidence  of  toxicity  in  new  samples  and 
 to  determine  which  insect  pests  were  susceptible.  Of  these  compounds 
 ZL3  were  found  sufficiently  effective  to  be  worthy  of  further  investi- 
 gation. These  compounds  were  therefore  subjected  to  additional  tests 
 in  the  laboratory  for  further  screening  to  select  materials  for  field 
 tests.  The  nonvolatile  materials  were  tested  in  screen  cages  to  deter- 
 mine their  value  as  possible  stomach  insecticides,  and  the  volatile 
 compounds  were  tested  for  their  fumigating  effect.  Inasmuch  as  a  pos- 
 itive test  as  a  stomach  poison  or  a  fumlgant  does  not  necessarily  pre- 
 clude the  possibility  of  contact  action,  all  the  compounds  that  were 
 effective  in  these  tests  were  scheduled  for  testing  as  contact  insecti- 
 cides. As  yet,  however,  only  a  few  compounds  have  been  tested,  and  the 
 method  has  not  been  perfected.  Most  of  the  methods  employed  have  been 
 described  by  Swingle,  Phillips,  and  Gahan  (8). 
 
 Since  the  establishing  of  evidence  of  stomach  or  contact  action 
 must  be  followed  by  tests  on  the  tolerance  of  plant  foliage  to  the 
 insecticides  before  any  decision  can  be  made  as  to  the  possibilities 
 of  the  new  materials,  phyto toxicity  tests  were  also  made  on  35  of  the 
 compounds. 
 
 Most  of  the  compounds  tested  and  reported  in  this  paper  were 
 received  from  the  Division  of  Insecticide  Investigations,  and  some  of 
 them  have  been  patented  as  insecticides  by  members  of  that  Division. 
 A  few  additional  compounds  were  purchased  by  the  Division  of  Control 
 Investigations.  More  often  than  not,  the  compounds  were  received  in 
 
 1/  M.  C.  Swingle  resigned  December  18,  1943,  J.  B.  Gahan  was 
 transferred  to  the  Division  of  Insects  Affecting  Man  and  Animals 
 February  1,  1943,  and  A.  M.  Phillips  was  transferred  to  the  Division 
 of  Fruit  Insect  Investigations  July  1,  1941. 
 
 UP  2  2  1947     2/  The  writers  acknowledge  the  assistance  of  members  of  the 
 
 Division  of  Insecticide  Investigations  who  supplied  most  of  the  com- 
 pounds tested. 
 
-2- 
 
 the  comparatively  coarse  condition  common  to  most  laboratory  chemicals, 
 and,  although  coarse  samples  were  always  ground  in  a  mortar  to  obtain 
 finer  particles,  the  materials  used  were  generally  much  coarser  than 
 commercial  insecticides.  This  is  important  in  judging  the  results 
 presented,  because  it  has  been  shown  that  particle  size  influences  the 
 effectiveness  of  insecticidal  materials  (2,  &) . 
 
 As  the  testing  proceeded,  the  few  outstanding  compounds  were  easily 
 recognized  and  were  singled  out  for  individual  investigation.  Four  of 
 these  compounds  have  been  investigated  in  some  detail  and  reports  pub- 
 lished on  this  work — phthalonitrile  (6),  l,4.-diphenylsemicarbazide  (1), 
 j^-aminoazobenzene  hydrochloride  Q) ,  and  pr-phenylazoaniline  (p.-amino- 
 azobenzene)  (X) . 
 
 INSECTS  TESTED 
 
 The  tests  described  in  the  present  paper  were  made  on  15  species  of 
 insects  which  are  listed  below.  Not  all  compounds  were  tested  on  all 
 insects  but,  in  general,  more  species  were  used  with  the  more  effective 
 "materials.  The  plant  or  foliage  used  with  the  various  insects  is  also 
 given,  because  this  factor  has  been  shown  to  influence  the  results  of 
 insecticide  tests  (jjj  • 
 
 Insect 
 
 Cabbage  aphid  (Brevlcoryne  brassicae  (L.)) 
 Colorado  potato  beetle  (Leptinotarsa 
 
 rjecftfijijiflftflfo  (Say)) 
 Cowpea  weevil  (flfrljo^obruchus  macula tus  (F.)) 
 Cross-striped  cabbageworm  (Evergestis 
 
 rimosalis  (Guen.)) 
 Diamondback  moth  ( BlgfcfiUfl  maculipennis 
 
 (Curt.)) 
 Spirea  aphid  (Aphis  spiraecola  (Patch) 
 Greenhouse  leaf  tier  (Phlyc taenia  rubjgalis 
 
 (Guen.)) 
 Hawaiian  beet  webworm  (Hymcnla  recurvali^  (F.)) 
 Imported  cabbageworm  (Ascia  rapae  (L.)) 
 Melonworm  (Diaphania  hyalinata  (L. ) ) 
 Pea  aphid  (Macrosjphum  pjsi  (Kltb.)) 
 Rice  weevil  (Sitophilus  orzya  (L.)) 
 Southern  armyworm  (Prodenia  erjcJanla  (Cram.)) 
 Southern  beet  webworm  (Pachyzancla 
 
 bipunctalis  (F.)) 
 Squash  bug  (Anasa  tristis  (Deg.)) 
 
 Foliage 
 
 Collards 
 Potato 
 
 Bean  (seed) 
 Collards 
 
 Collards 
 
 Oren6e 
 Collards 
 
 Swiss  chard 
 
 Collards 
 
 Pumpkin  and  squash 
 
 Pea 
 
 Corn  (seed) 
 
 Collards 
 
 Swiss  chard 
 
 Squash 
 
 TESTS  AS  STOMACH  INSECTICIDES 
 
 For  the  first  test  on  a  new  material  as  a  possible  stomach  insecti- 
 cide, a  concentration  of  1  percent  (8  pounds  per  ICO  gallons) was  used. 
 Lower  concentrations  were  used  in  subsequent  tests  on  the  effective 
 compounds.  Each  spray  was  applied  to  2  potted  plants  (6  to  8  inches 
 high)  by  means  of  a  compressed-air  spray  gun.  When  the  plants  were  dry, 
 
-3- 
 
 15  nearly  full  grown  larvae  were  confined  on  each  within  a  cylindrical 
 screen  cage,  which  was  placed  over  the  plant  and  gently  forced  into  the 
 soil  about  the  inside  upper  edge  of  the  pot.  The  cages  were  then 
 placed  out-of-doors  in  a  sheltered  location  and  examined  after  2,  U,   and 
 6  days  for  larval  mortality  and  to  estimate  the  feeding  on  the  plants. 
 
 In  these  spray  tests  L   compounds  were  used  as  conditioning  agents, 
 saponin  and  sodium  lauryl  sulfate  at  l/u   and  l/B  pound  per  100  gallons 
 of  spray,  sodium  mono  sulfonate  of  monobutyldiphenyl  at  1  or  2  pounds  per 
 100  gallons,  and  bentonite  at  8  pounds  per  100  gallons.  These  amounts 
 have  no  particular  significance,  however,  as  no  experiments  were  made  to 
 determine  the  most  satisfactory  concentration  of  these  agents,  other 
 than  that  of  saponin.  Preliminary  tests  with  this  agent  showed  that 
 l/S  pound  per  100  gallons  produced  a  satisfactory  spray  in  most  cases. 
 In  work  of  this  kind  probably  no  one  agent  can  be  selected  which  will 
 give  optimum  results  with  all  the  compounds  because  of  the  variation  of 
 the  physical  properties  of  each  agent.  Only  small  quantities  of  spray 
 were  made,  usually  by  grinding  the  compound  in  a  mortar  with  the  agent 
 and  gradually  diluting  with  water  to  the  required  concentration. 
 
 Table  1  reports  the  results  of  screen-cage  tests  on  97  of  the  niore 
 promising  compounds,  and  on  derris  and  lead  arsenate  as  standards  for  com- 
 parison. Although  the  status  of  a  few  compounds  is  somewhat  obscure  because 
 of  limited  testing,  only  U  materials  in  the  table  would  appear  to  be  equal 
 to,  or  better  than,  derris  or  lead  arsenate.  The  outstanding  compounds  are 
 l,4.-diphenylsemicarbazide  (1)  and  phthalonitrile  (6) .  Pentabromophenol  and 
 barium  antimonyl  tartrate  were  above  the  average  in  effectiveness.  It 
 should  be  added  that,  although  phenol  and  cresol  compounds  were  in  general 
 very  toxic,  their  tendency  to  cause  severe  injury  to  foliage  eliminates 
 most  of  them  from  consideration.  In  general,  of  the  compounds  in  table  1, 
 the  following  IS  compounds  were  sufficiently  effective  to  warrant  further 
 investigations  as  stomach  insecticides: 
 
 2-Acetamidofluorene 
 Acetone  semicarbazone 
 £-Aminoazobenzene 
 PT-Aminoazobenzene  hydrochloride 
 Antimonyl  pyrogallol 
 Barium  antimonyl  tartrate 
 £-Chlorobenzenesulfonamide 
 Diazoaminobenzene 
 2,4-Dinitrophenyl  acetate 
 
 1 , 4-Dinitrosopiperazine 
 
 1 ,  4vDiphenylsemlcarbazide 
 
 2-FLuorylamine 
 
 Hexachlorophenol 
 
 Pentabromophenol 
 
 Phenazine 
 
 Phthalonitrile 
 
 Tris  ( jfc-aminophenyl)  carbinol 
 
 Xanthydrol 
 
 Sixteen  others  were  very  effective  on  a  few  species,  but  this 
 specificity  greatly  limited  their  importance  as  insecticides. 
 
 Of  the  compounds  listed,  6  are  shown  in  table  6  to  be  very  injuri- 
 ous to  foliage,  and  are  thus  eliminated  from  further  investigation  as 
 stomach  insecticides.  These  are  2,4.-dinitrophenyl  acetate,  hexachloro- 
 phenol, pentabromophenol,  phenazine,  tris (jj-aminophenyl)  carbinol,  and 
 xanthydrol.  The  antimony  compounds  and  jB-chlorobenzenesulfonamide  were 
 not  tested  for  foliage  injury. 
 
-u- 
 
 The  53  compounds  that  were  found  to  be  relatively  ineffective  as 
 stomach  insecticides  are  shown  in  table  2. 
 
 FUMIGATION  TESTS 
 
 Two  types  of  fumigation  tests  were  m*^e.  The  test  in  petri  dishes 
 was  conducted  by  placing  a  leaf  section  and  10  larvae  in  each  of  2  or  3 
 petri  dishes  together  with  a  quantity  of  the  sample,  into  the  top  of  each 
 dish.  This  permitted  volatilization  of  the  compound  within  the  dish,  but 
 prevented  contact  between  the  insects  and  the  solid  insecticide.  This 
 type  of  fumigation  test  was  used  only  against  leaf-eating  insects. 
 
 Compounds  found  to  be  toxic  in  petri  dishes  were  further  tested  as 
 fumigants  against  cowpea  weevil  and  rice  weevils  in  special  fumigation 
 jars.  The  standard  jar  was  a  half -pint  fruit  jar  with  a  screw  cap,  but 
 larger  jars  were  sometimes  used  with  the  more  toxic  materials.  Each 
 screw  cap  had  a  hole  fitted  with  a  sleeve  of  3/8-inch  brass  tubing 
 through  which  a  perforated  tube  containing  25  insects  could  be  inserted. 
 With  these  jars  the  fumigant  could  first  be  volatilized  by  heat  or 
 allowed  to  stand  until  evaporated,  and  the  insects  inserted  when  desired, 
 thus  eliminating  the  usual  loss  of  time  caused  by  a  gradual  build-up  in 
 the  concentration. 
 
 Table  3  gives  the  results  of  the  tests  on  51  compounds  that  were 
 found  to  have  appreciable  fumigating  action.  Of  these  compounds  17  were 
 effective  against  at  least  several  species  of  lepidopterous  larvae,  and 
 the  following  8  were  effective  against  most  of  the  species  on  which  they 
 were  tried: 
 
 £-Dibromobenzene  £-NItrochlorobenzene 
 
 2 , 5-Dichloroaniline  A-Ni trodiphenylamine 
 
 Indole  p^Thiocyanochlorobenzene 
 
 p_-Nitrochlorobenzene  2,6-Xylenol 
 
 Best  results  were  obtained  with  j^-thiocyanochlorobenzene,  which 
 appeared  to  be  somewhat  more  effective  than  the  standard  fumigant 
 jg-dichlorobenzenet  Most  of  the  other  materials  were  either  less  toxic 
 or  less  volatile  than  this  standard  insecticide  and  were  not  considered 
 promising  as  fumigants.  Many  organic  compounds  displaying  fumigating 
 action  under  these  conditions  are  unsuitable  for  commercial  use, 
 because  they  lack  the  volatility  for  a  rapid  build-up  to  the  desired 
 concentration.  Certain  of  these  compounds  may  be  effective  as  contact 
 insecticides,  however,  inasmuch  as  rapid  or  complete  volatility  is  not 
 essential  in  this  case. 
 
 Ninety  compounds  tested  as  fumigants  were  relatively  ineffective 
 against  all  species  of  insects  on  which  they  were  tested,  and  are  listed 
 alphabetically  in  table  4.. 
 
 CONTACT  TESTS 
 
 In  the  tests  to  determine  the  effectiveness  of  materials  as  contact 
 
-5- 
 
 insecticides,  they  were  applied  as  sprays  containing  8  or  U   pounds  of 
 the  compound  and  \  pound  of  saponin  per  100  gallons  of  water.  In  tests 
 against  aphids  the  sprays  were  applied  to  infested  plants,  but  in  other 
 cases  only  the  insects  were  treated.  For  the  pea  aphid,  small  potted 
 plants  infested  with  50  to  100  grown  nymphs  were  sprayed,  placed  in  glass 
 jars,  and  covered  with  cheesecloth  caps.  Field  infestations  on  collard 
 plants  were  used  for  the  tests  on  the  cabbage  aphid,  samples  of  100 
 aphids  being  counted  in  each  test.  For  the  spirea  aphid,  heavily  infested 
 orange  twigs  were  cut  and  sprayed  and  then  placed  in  flasks  of  water  in 
 glass  jars  for  observation,  100  aphids  being  used  in  each  test.  Squash 
 bugs,  20  per  test,  were  dipped  into  the  spray  suspension  and  then  trans- 
 ferred to  small  screen  cages  with  a  very  small  squash  as  food.  Tests  on 
 lepidopterous  insects  were  made  by  placing  15  larvae  on  a  sheet  of 
 absorbent  paper  and  spraying  thoroughly  with  a  compressed-air  gun.  The 
 larvae  were  then  transferred  to  foliage  in  a  ventilated  cage. 
 
 Contact  tests  were  made  on  22  compounds  (table  §),  including  those 
 showing  fumigating  action  in  the  tests  reported  in  table  3»     Of  the  8 
 effective  fumigants  only  U  were  tested  for  contact  action,  and  these 
 were  not  found  effective.  Nine  of  the  compounds  tested  were  effective 
 against  aphids,  and  alpha,  beta-dibromo-beta-nitroethylbenzene,  2,4- 
 dinitrophenyl  acetate,  and  g-nitroaniline  were  effective  against  the 
 pea  aphid  at  both  concentrations .  None  of  the  compounds  were  very  effec- 
 tive against  the  other  insects.  Nicotine  sulfate  was  much  more  toxic 
 than  any  of  the  other  compounds  tested. 
 
 PHTT0T0XICITY  TESTS 
 
 The  phytotoxicity  tests  were  made  on  small  field  plots  of  certain 
 truck  crops.  Sprays  prepared  at  concentrations  of  8  or  U  pounds  per  100 
 gallons  were  applied  to  U   to  20  plants  with  a  hand-type  air  sprayer. 
 Most  of  the  tests  reported  were  made  on  the  basis  of  a  single  application, 
 but  in  later  work  two  applications  at  10-day  intervals  were  used  as  a 
 standard  procedure  .  To  eliminate  the  possibility  that  rainfall  might 
 effect  the  results,  the  sprayed  plants  were  covered  at  night  and  during 
 showers. 
 
 Of  the  35  compounds  tested  (table  6),  approximately  17  were  found 
 unsafe  for  use  on  foliage,  causing  moderate  to  severe  injury  on  two  or 
 more  of  the  plants  used.  It  is  possible  that  certain  compounds  nontoxic 
 to  the  plants  tested  might  be  toxic  to  other  host  plants.  Different 
 results  may  also  be  expected  from  the  same  host  plants  under  other 
 environmental  conditions. 
 
 Of  the  18  compounds  found  to  be  most  effective  as  stomach  insecti- 
 cides (table  1),  15  were  tested  for  foliage  Injury.  Of  these  compounds 
 6  were  too  injurious  to  foliage  for  further  investigations. 
 
-6- 
 
 sumiarx 
 
 Results  of  subsequent  testing  of  213  synthetic  organic  compounds 
 found  promising  as  insecticides  in  preliminary  tests  are  presented. 
 Ninety-seven  out  of  150  compounds  were  effective  when  applied  as  sprays 
 to  potted  plants,  which  were  then  fed  to  certain  leaf -eating  insects 
 in  screen  cages.  In  these  tests  the  following  18  compounds  were  shown 
 to  be  worthy  of  further  investigation  as  stomach  insecticides: 
 
 2-Acetamidofluorence 
 
 Acetone  semicarbazone 
 
 X>-Aminoazobenzene 
 
 g-Aminoazobenzene  hydrochloride 
 
 Antimonyl  pyrogallol 
 
 Barium  antimonyl  tartrate 
 
 £-Chloro  benzene  sulfonamide 
 
 Diazoaminobenz  ene 
 
 2,A-Dinitrophenyl  acetate 
 
 1 , 4-Dini  tro  sopiperazine 
 
 1 , 4-Diphenylsemi  carbazide 
 
 2-Fluorylamine 
 
 Hexachlorophenol 
 
 Pentabromophenol 
 
 Phenazine 
 
 Phthalonitrile 
 
 Tris(a-amino  phenyl)  carbinol 
 
 Xanthydrol 
 
 Results  are  also  presented  on  fumigation  tests  of  141  compounds. 
 Eight  of  these  were  found  to  be  toxic  to  most  of  the  insects  used,  but 
 only  £-thiocyanochlorobenzene  was  more  effective  than  jh-dichlorobenzene. 
 
 Twenty-two  compounds  were  applied  to  insects  as  contact  sprays,  but 
 no  outstanding  insecticides  were  found.  Nine  of  the  compounds  were 
 effective  against  aphids,  but  only  three  were  sufficiently  toxic  to  kill 
 the  pea  aphid  at  spray  concentrations  of  U   and  8  pounds  per  100  gallons, 
 which  are  considerably  stronger  than  an  effective  nicotine  spray. 
 
 Of  35  compounds  tested  for  toxicity  to  plant  foliage,  approximately 
 half  severely  injured  certain  tender  truck  crops  and  were  "tons  unsuit- 
 able for  use  as  stomach  insecticides  on  foliage. 
 
-7- 
 
 LITERATURE  CITED 
 
 (1)  Gahan,  J.  B.,  Swingle,  M.  C.,  and  Phillips,  A.  II. 
 
 1941.  1,4-Diphenylsemicarbazide  as  an  insecticide.  U.  S. 
 
 Bur.  Ent.  and  Plant  Quar.  E-549,  11  pp.  (Processed.) 
 
 (2)  McGovran,  E.  R. ,  Cassil,  C.  C,  and  Mayer,  E.  L. 
 
 194-0.  Particle  size  of  paris  green  as  related  to  toxicity 
 and  repellency  to  the  Mexican  bean  beetle.  Jour. 
 Econ.  Ent.  33:  525-531. 
 
 (3)  Phillips,  A.  M.,  Swingle,  M.  C,  Gahan,  J.  B.,  and  McGovran,  E.  R. 
 
 1941.  £-Aminoazobenzene  hydrochloride  as  an  insecticide.  U.  S. 
 Bur.  Ent.  and  Plant  Quar.  E-55O,  8  pp.  (Processed.) 
 
 (4)  Siegler,  E.  H.,  and  Goodhue,  Lyle  D. 
 
 1939*  Effect  of  particle  size  of  some  insecticides  on  their 
 toxicity  to  the  codling  moth  larvae.  Jour.  Econ. 
 Ent.  32:  199-203. 
 
 (5)  Swingle,  M.  C. 
 
 1939.  The  effect  of  previous  diet  on  the  toxic  action  of  lead 
 arsenate  to  a  leaf-feeding  insect.  Jour.  Econ.  Ent. 
 32:  884. 
 
 (6)  _ ,  Gahan,  J.  B.,  and  Phillips,  A.  M. 
 
 1941.  Phthalonitrile  as  an  insecticide.  U.  S.  Bur.  Ent.  and 
 
 Plant  Quar.  E-548,  12  pp.  (Processed.) 
 
 (7) ,  Gahan,  J.  B.,  and  Phillips,  A.  M. 
 
 1942.  £-Phenylazoaniline  as  an  insecticide.  U.  S%  Bur.  Ent. 
 
 and  Plant  Quar.  E-565,  9  pp.  (Processed.) 
 
 (8)  .  Phillips,  A.  M.,  and  Gahan,  J.  B. 
 
 1941.  Laboratory  testing  of  natural  and  synthetic  organic 
 substances  as  insecticides.  Jour.  Econ.  Ent.  34: 
 95-99. 
 
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-25- 
 Table  2. — Compounds  found  relatively  ineffective  as  stomach  insecticides 
 
 Compound 
 
 Insect 
 
 Aminodiphenylamine  hydrochloride 
 C^cNHC^NH^Cl 
 
 alpha-Ani  saldoxime 
 CH3OC6H^CHNOH 
 
 ,4-BenzoylJiiorpholine 
 
 o-Bromoacetanilide 
 CH3COMHC6H,Br 
 
 p_-Bromohydrazobenzene 
 BrC6H,NHNHC6H5 
 
 2-Butanone  semicarbazone 
 C2H5C(NNHC0M12)CH3 
 
 N-n-Butyl-p-toluenesulfonamide 
 CH3C6H^S02NHC^H9 
 
 3-Chloroacenaphthene 
 
 C,J  (CH  )  CI 
 10  5   2  2 
 
 alpha , beta-Dibromo  e thylbenzene 
 
 C^CHBrCiyr 
 
 alpha, beta-Dibromo-beta- 
 nitroethylbenz  ene 
 C6H.CHBrGH(Br)N02 
 
 Di-" Cello solve"  xanthogen 
 
 Lc/W 
 
 u 
 
 Di  e thylxanthogen 
 
 Greenhouse  leaf  tier 
 
 do* 
 
 Southern  armyworm 
 
 Greenhouse  leaf  tier 
 
 Cross-striped  cabbageworm 
 
 Melonworm 
 
 Southern  armyworm 
 
 Melonworm 
 
 Southern  beet  webworm 
 
 Cross-striped  cabbageworm 
 Southern  armyworm 
 
 do. 
 
 do. 
 
 Cross-striped  cabbageworm 
 Greenhouse  leaf  tier 
 Hawaiian  beet  webworm 
 Melonworm 
 Southern  armyworm 
 Southern  beet  webworm 
 
 Imported  cabbageworm 
 Melonworm 
 Southern  armyworm 
 
 Imported  cabbageworm 
 Melonworm 
 Southern  armyworm 
 
Table  2. — (Continued) 
 
 -2(>- 
 
 Compound 
 
 Insect 
 
 3, 5-Diiodo salicylic  acid 
 I2C6H2(0H)C00H 
 
 Diisoamylxanthogen 
 
 °12?260rS 
 
 Dimethylacantho  gen 
 
 W2S4 
 
 2 , 4-Dinitroanisole 
 CH30C6H3(N02)2 
 
 m-Dinitrobenzene 
 C6H4(H02)2 
 
 Southern  armyworm 
 Southern  beet  webworm 
 
 Southern  armyworm 
 
 do. 
 
 Southern  beet  webworm 
 
 Hawaiian  beet  webworm 
 Melonworm 
 Southern  armyworm 
 Southern  beet  webworm 
 
 Diphenyl  ester  of  carbonic  acid 
 (C6H50)2CO 
 
 Cross-striped  cabbageworm 
 
 Melonworm 
 Southern  armyworm 
 
 Dixanthogen  of  monomethyl  ether  of 
 ethylene  glycol 
 
 Ethyl  ester  of  cyanoacetic  acid 
 CNCH  COOC  H 
 
 N-( 2-FLuoryl) palmitamide 
 
 Heptadecyl  xylyl  ketone 
 °26V 
 
 l-Hydroxy-2-acetonaphthone 
 C10H6(OH)COCH3 
 
 2 , 2-Bi  s ( hydroxyme thyl ) -1-butanol 
 (CH20i53CC2H5 
 
 o-Iodoacetanilide 
 "  CH3CONHC6H^I 
 
 p-Iodoaniline 
 -  IC6H4HH2 
 
 do. 
 
 do. 
 
 Greenhouse  leaf  tier 
 
 Southern  armyworm 
 
 Greenhouse  leaf  tier 
 Southern  armyworm 
 
 do. 
 
 Melonworm 
 
 do. 
 Southern  armyworm 
 
-27- 
 
 Table  2. — (Continued) 
 
 Compound 
 
 Insect 
 
 N-Methyl-m-acetotoluide 
 
 ch3conTch3) c6h^ch3 
 
 Methyl  3-methoxy-2-naphthoate 
 C10H6(OCH3)COOCH3 
 
 Cross-striped  cabbageworm 
 
 Southern  armyworm 
 
 Methyl-2-naphthyl  ether 
 
 Cross-striped  cabbageworm 
 
 1-Naphthol 
 
 Hawaiian  beet  webworm 
 
 Melonworm 
 
 Southern  beet  webworm 
 
 1-Naphthonitrile 
 C10H7CN 
 
 Southern  armyworm 
 
 o-Mitroaniline 
 
 Greenhouse  leaf  tier 
 Hawaiian  beet  webworm 
 Melonworm 
 Southern  armyworm 
 Southern  beet  webworm 
 
 Pj-Nitrobenzyl  chloride 
 (M02)C6H4CH2C1 
 
 o-Hi  trophenyliodo  chloride 
 (H02)C6H^IC12 
 
 2-Nitroresorcinol 
 (N02)C6H3(OH)2 
 
 1-Phenylbenzoxazole 
 C6H4HC(C6Hs)0 
 
 Piperazine  (Hydrate) 
 IB(0H2)2HH(0H2)2.6iy) 
 
 Hawaiian  beet  webworm 
 Melonworm 
 Southern  armyworm 
 Southern  beet  webworm 
 
 Greenhouse  leaf  tier 
 
 do. 
 Southern  armyworm 
 Southern  beet  webworm 
 
 Hawaiian  beet  webworm 
 Southern  armyworm 
 
 do. 
 
 p_-Propiono  toluide 
 
 C  H  CONHC,H,CH_ 
 2  5  6  A    3 
 
 Greenhouse  leaf  tier 
 Southern  armyworm 
 
 Quinaldine 
 
 CJTCHCHC(CHjM 
 |o  4  3  , 
 
 do. 
 
-28- 
 
 Table  2. — (Continued) 
 
 Compound 
 
 Insect 
 
 Bhodanine 
 
 gC(fc)NHCOCH2 
 
 Salicyl aldehyde  semicarbazone 
 H0C6H,CHMHMHCONH2 
 
 Sulf-glycerides  of  corn  oil 
 
 Sulfoleic  acid 
 
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 p-Tolylmethenyl-p , p f -bis- 
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 CH3C6Hi!,CH(C6H^(CH3)2>2 
 
 Greenhouse  leaf  tier 
 Melonworm 
 Southern  armyworm 
 
 Southern  beet  webworm 
 
 Imported  cabbageworm 
 Melonworm 
 Southern  armyworm 
 
 Imported  cabbageworm 
 Melonworm 
 Soutliern  armyworm 
 
 do. 
 
 do. 
 
 do. 
 do. 
 
 1,3, 5-Tribromobenz  ene 
 C6H3Br3 
 
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 C,H.CHoC,H.0 
 
 Xanthone 
 
 C^COC^O 
 
 Zinc  n-amylxanthate 
 
 Zinc  isoamylxanthate 
 Zn(C5HuOCS2)2 
 
 Melonworm 
 
 Southern  armyworm 
 
 Melonworm 
 Southern  armyworm 
 
 do. 
 
 do. 
 
 do. 
 
-29- 
 
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-38- 
 
 Table  U  —  Compounds  found  relatirely  lnef feet ire  as  fumigants 
 
 Compound 
 
 Insect 
 
 Stage  1/ 
 
 Acetone  semicarbazone 
 (0H3)2CHHHC0,,H2 
 
 3-»Acetoxy--2-naphthoic  acid 
 CH,COOC10HgCX)OH 
 
 Diamondback  moth 
 Greenhouse  leaf  tier 
 
 Southern  armyvorm 
 
 Arsenic  ethyl  xanthate 
 AsCC^OCS^ 
 
 Barium  antlmonyl  tartrate 
 BatCSDOjC^B^Ogjg 
 
 BenzsHazine 
 
 CgH-CHNNCHCgH- 
 
 fourth 
 fifth 
 
 first 
 
 p-Aalnoazobenzene 
 
 Cross-striped  cabbagevorm 
 
 Melonvorm 
 
 Southern  armyvorm 
 
 fourth 
 do. 
 do. 
 
 p-Amlnoasobensene  hydrochloride 
 ~    CgB^HgCgB^HBg.HCl 
 
 Qrose-striped  cabbagevorm 
 Southern  armyvorm 
 
 do. 
 do. 
 
 3-Aalnodlbenzofuran 
 ?6%°?6H3IH2 
 
 Greenhouse  leaf  tier 
 Southern  armyvorm 
 
 Greenhouse  leaf  tier 
 Southern  armyvorm 
 
 Tifth 
 Sixth 
 
 U-Aminoblphenyl 
 C6H5C6H^IIH2 
 
 fifth 
 fourth 
 
 Amlnodiphenylamlne 
 
 Greenhouse  leaf  tier 
 
 fifth 
 
 hydrochloride 
 (CgH^^.HCl 
 
 alpha-Anisaldoxime 
 CH,OCgH^CHHOH 
 
 Cross-striped  cabbagevorm 
 Southern  armyvorm 
 
 'ourth 
 Jirst 
 
 Antlmonyl  pyrogallol 
 HOCgH-O?  SdOH)0 
 
 Melonvorm 
 
 fourth 
 
 Southern  armyvorm  First 
 
 Melonvorm  fourth 
 
 Cross-striped  cabbagevorm       Third 
 Melonvorm  fourth 
 
 Southern  armyvorm  do. 
 
 1/  Number  refers  to  lnstar. 
 
-39- 
 
 Table  4— (Continued) 
 
 Compound 
 
 Insect 
 
 Stage  1/ 
 
 Benzoplnaeol 
 
 (  CgHj)^  OH)C(  0H)(  C6H5)2 
 
 Southern  armyworm 
 
 Firet 
 
 £-Br  omobenz  ene  sulfonamide 
 BrCgH^SOgHHg 
 
 do. 
 
 Sixth 
 
 p~Br omobenzenesulf onanil ide 
 "  BrCgH^SOgMHCgH^ 
 
 Colorado  potato  beetle 
 
 Fourth 
 
 p-Bromohydrazobenzene 
 -  BrCgH^HHNHCgHc 
 
 Southern  armyworm 
 
 do. 
 
 N-(  p_-Bromophenylsulf  onyl ) 
 
 Colorado  potato  beetle 
 
 do. 
 
 morpholine 
 BrCgH^SOgNC  CHgCHg)  20 
 
 o-Chlor oacet anil ide 
 
 Melonworm 
 
 do. 
 
 CHjCONHCgH^Cl 
 
 p~Chloroacetanillde 
 CH-COJJHCgH^Cl 
 
 Southern  armyworm 
 
 do. 
 
 p-Chlor obenzene sul f onam ide 
 
 do. 
 
 do. 
 
 —  ClCgH^SOgHHg 
 
 Cupferron 
 
 Greenhouse  leaf  tier 
 
 Fifth 
 
 CgHJJdJCOOHB^ 
 
 Cyclohexanone  semiearbazone 
 CgB^QNNHCOHHg 
 
 N-Cyclohexylpyromucamide 
 ( C^E.0)  COHHCgHj^ 
 
 alpha, bet a-Dibromo-beta- 
 nitroethylbenzene 
 C6H_CHBrCH(Br)HO 
 
 3 ( U-D  i  chl or oacet ophenone 
 
 Hawaiian  beet  webworm         do. 
 
 Melonworm  Fourth 
 
 Cross-striped  cabbageworm      do. 
 Southern  armyworm  do. 
 
 Melonworm  do. 
 
 Cl2C6H3 
 
 COCH, 
 
Table  l  -— ( Continued) 
 
 -40- 
 
 Compound 
 
 Insect 
 
 Stage  1/ 
 
 2 , 7-^lchlorof  luorene 
 OlC^CHgO^Cl 
 
 Dickioraraine-T 
 
 CEjC^scysrcig 
 
 2, 6«Dlchloro-U-nltrophenol 
 C12C6H2(N02)0H 
 
 U, 6-Dlnitro-o-cresol 
 (N02)2C6H2(CH_)OH 
 
 4,6-J)initro«o«cregyl  acetate 
 (NO^CgH^CH^OCOCHj 
 
 B  lni  t  r  o~o-cycl  ohexylphenol 
 
 1 ,  S~Dinltronaphthalene 
 
 N02C10H6H02 
 
 2 ,  ^l-Dlni  trophenol 
 
 U02)2C6H3OH 
 
 2,4-Dinitrophenyl  acetate 
 CH,C02CgEj(B02)2 
 
 2 , U-D lni t  r 0-6-phenylphenol 
 °6H506H2(H02)2OH 
 
 1,4-1)  initrosopiperazine 
 
 K-yinitrosopiper 
 O^CHgCHgJgHNO 
 
 2,U-Dinitrotoluene 
 
 Southern  armyvorm 
 
 do. 
 
 CH,C 
 
 sty10^ 
 
 Southern  armyvorm 
 
 do* 
 
 Oiamondhack  moth 
 Greenhouse  leaf  tier 
 Southern  armyvorm 
 
 do. 
 
 do. 
 
 Colorado  potato  beetle 
 Greenhouse  leaf  tier 
 
 Colorado  potato  beetle 
 
 First 
 
 do. 
 
 Greenhouse  leaf  tier 
 Southern  armyvorm 
 Southern  beet  vebworm 
 
 Fifth 
 Fourth 
 do. 
 
 Colorado  potato  beetle 
 Dlamondbacfc  moth 
 Greenhouse  leaf  tier 
 Melonworm 
 Southern  armyvorm 
 
 do. 
 
 do. 
 Fifth 
 fourth 
 Sixth 
 
 Hawaiian  beet  vebvorm 
 
 Melonvorm 
 
 Southern  beet  vebvorm 
 
 Fifth 
 fourth 
 do. 
 
 Sixth 
 
 First 
 
 Fourth 
 
 Fifth 
 
 First 
 
 Fourth 
 
 Sixth 
 
 Fourth 
 Fifth 
 
 Fourth 
 
-41- 
 
 lable  U   — (Continued) 
 
 Compound 
 
 Insect 
 
 Stage  1/ 
 
 1  t4~Diphenylsemicarbazide 
 CgHlNHMHCOHHCgH. 
 
 Disulfurons  acid, 
 
 ?entaerythritol ,  ester  of 
 0S(0CH2)2]2C 
 
 Dithiooxamide 
 
 m2c($)c{s)}m2 
 
 Fluor one 
 
 4-Jluorobiphenyl 
 C6H5C6V 
 
 2-Fluorylamine 
 C6%CH296H3MH2 
 
 N-(  2-Fluoryl)palmltamide 
 C15H31C0NHC13H9 
 
 p-Formo  t  oluide 
 "  HCOHHCgH^CH, 
 
 ( 
 
 C^H30) 
 
 CHNHHCOHH, 
 
 2-^ur anacr ylam  ide 
 
 (C^O) 
 
 CONH, 
 
 2-Heptanone  semlcarbazone 
 CRy  CH2)^C(  CH-)NMC0NH2 
 
 l-Hydroiy-2-acetonaphthone 
 C10H6(OH)COCH3 
 
 Greenhouse  leaf  tier 
 Imported  cabbageworm 
 Melonworm 
 Southern  armyworm 
 Southern  beet  webworm 
 
 Colorado  potato  beetle 
 
 do. 
 
 Southern  army-worm 
 
 do* 
 
 do. 
 
 Greenhouse  leaf  tier 
 
 Greenhouse  leaf  tier 
 Southern  armyworm 
 
 2-Sur aldehyde  semlcarbazone    Melonworm 
 
 do. 
 
 Hawaiian  beet  webworm 
 
 Greenhouse  leaf  tier 
 Southern  armyworm 
 
 Fifth 
 do. 
 
 Fourth 
 do. 
 
 Fifth 
 
 Fourth 
 
 do. 
 
 Sixth 
 
 Fourth 
 
 do. 
 
 Fifth 
 
 do. 
 
 Fourth 
 
 do. 
 
 do. 
 
 Fifth 
 
 do. 
 
 Fourth 
 
-42- 
 
 Table  4  —(Continued) 
 
 Compound 
 
 Insect 
 
 Stage  1/ 
 
 3-Hydroxy-2~naphthoic  acid 
 C1()Hg(OH)COOH 
 
 o-Iodoacetanilide 
 CH,COSHCgH^I 
 
 2-Iodofluorene 
 Cg^CHgCgHjX 
 
 U«Methoxyacridone 
 CgH^COCgH,(  OCH,  )HH 
 
 H-Methyl-a-acetotoluide 
 CEjCOHCCH,  )  CgH^CH, 
 
 Methyl-2«naphthyl  ether 
 Ci  rfLfOGiB.'i 
 
 1-Napht hyl i  so  t hio cyanat  e 
 
 HCS 
 
 LO1^ 
 
 p-Nitrobenzyl  bromide 
 (NOgJCgH^CHgBr 
 
 p~Si  t  ro  io  do  sobenz  ene 
 ~  (K02)C6H^IO 
 
 p~Hitrolodosobenzene  acetate 
 "  (H02)C6H^I(000CH3)2 
 
 1-Nit re naphthalene 
 
 1-N  J  t ro-2-napht hyl am ine 
 C^UO^ffiL, 
 
 BLSitrosodibenzylamine 
 CgH^CH^NOCHgC^ 
 
 Cross-striped  cabbage worm 
 Southern  armyvorm 
 
 Colorado  potato  beetle 
 
 Southern  armyvorm 
 
 TJ 
 
 do. 
 
 Colorado  potato  beetle 
 
 do. 
 Cross-striped  cabbagevorm 
 
 Colorado  potato  beetle 
 
 Greenhouse  leaf  tier 
 Southern  armyvorm 
 
 do. 
 
 Melonvorm 
 
 Cross-striped  cabbagevorm 
 Southern  armyvorm 
 
 Southern  armyvorm 
 
 Colorado  potato  beetle 
 
 fourth 
 Jirat 
 
 fourth 
 
 *irst 
 
 do. 
 
 fourth 
 
 do. 
 
 do. 
 
 do. 
 
 fifth 
 fourth 
 
 do. 
 
 do. 
 
 do. 
 Sixth 
 
 Fourth 
 
 do. 
 
-43- 
 
 fable  4  —(Continued) 
 
 Compound 
 
 Insect 
 
 Stage  1/ 
 
 N-N 1 1 to  so  diphenylam ine 
 (C^Hc)2M0 
 
 N-Hitroao-N-phenylbeazjlamine 
 CgH^UOCHgCgH- 
 
 Cross-striped  cabbageworm    fourth 
 Southern  armyworm  do* 
 
 Colorado  potato  beetle        do. 
 
 beta~Nitrosostyrene 
 
 C^HcCHCHNO 
 
 Southern  arayvorm 
 
 Sixth 
 
 Pent  abromophenol 
 Br5C6OH 
 
 Cross-striped  cabbageworm 
 Melonworm 
 
 fourth 
 do. 
 
 Pentachlorophenol 
 Cl5C6OH 
 
 Diamondbaem  moth 
 Greenhouse  leaf  tier 
 Hawaiian  beet  webworm 
 Southern  armyworm 
 Southern  beet  webworm 
 
 do. 
 *ifth 
 
 do. 
 Sixth 
 
 fourth 
 
 Phenazine 
 
 Cross-striped  cabbageworm 
 
 do. 
 
 Phenoxa&hUn 
 
 Southern  armyworm 
 
 Sixth 
 
 Phenoxazine 
 
 do. 
 
 fourth 
 
 Phthalonltrile 
 C6%(CH)2 
 
 Hawaiian  beet  webworm 
 
 Melonworm 
 
 Southern  beet  webworm 
 
 fifth 
 fourth 
 do. 
 
 p-Propionotoluide 
 "  CgHeCOMHCg^CH- 
 
 Greenhouse  leaf  tier 
 Southern  armyworm 
 
 fifth 
 fourth 
 
 Propyl  ester  of  p-hydroxy- 
 benzoic  acid 
 HOCgH^COOC^H, 
 
 Bhodanine 
 
 SC(S)NHCOCH2 
 
 Colorado  potato  beetle        do. 
 
 Greenhouse  leaf  tier        fifth 
 Southern  armyworm  fourth 
 
-u- 
 
 Table  A  —  (Continued) 
 
 Compound 
 
 Insect 
 
 Stage  1/ 
 
 T©t  re.br  omo-o-cresol 
 Brj^OHTCHj 
 
 2, 2, 6 , 6 ,  -Tetramethyl-1- 
 nitroeo-^+wpiperldone 
 (CH3)2CCEkCOC^C(^i)^H0 
 
 Th&llous  aalonate 
 CH2(C00Tl)2 
 
 Thloaeetanilide 
 CgB^HHCSCH^ 
 
 Thlocouaarin 
 C6^CHCHC(S)0 
 
 p-Thiocyano  iodoben*ene 
 ""  ICgH^SCK 
 
 alpha^Th  io  t  oluam  ide 
 C6H5CH2CSNH2 
 
 N-p-Tolyl-p-tcluenesvlfonamide 
 CHTCgH^OgHHCgH^CH, 
 
 2,U,6-Triiodophenol 
 I3C6H2OH 
 
 2 , k , 6-Tr  in  i t ro-m-creeol 
 (N02)3C6H(CH3)(OH) 
 
 Ble(  2,  U,  6~trlnitrophenyl)  amine 
 [(HOg^HgJgHH 
 
 1.1. 3-^r  iphenylguanidine 
 HHCCHHCgH^NfCgHjg 
 
 Hawaiian  beet  vebvora 
 Southern  arayvora 
 Southern  beet  vebvora 
 
 Colorado  potato  beetle 
 
 Southern  arayvorm 
 
 do. 
 
 Diamondback  moth 
 Greenhouse  leaf  tier 
 Southern  armyvora 
 
 Cross-striped  cabbagevora 
 Diaaondback  aoth 
 Greenhouse  leaf  tier 
 Southern  armyvora 
 
 do. 
 
 Colorado  potato  beetle 
 
 do. 
 Cross-striped  cabbagevora 
 
 Diaaondback  aoth 
 Greenhouse  leaf  tier 
 
 Colorado  potato  beetle 
 Cross-striped  cabbagevora 
 
 Colorado  potato  beetle 
 
 *ifth 
 'ourth 
 do. 
 
 do. 
 
 Sixth 
 
 do. 
 
 fourth 
 
 fifth 
 
 Sixth 
 
 fourth 
 
 do. 
 fifth 
 fourth 
 
 Sixth 
 
 fourth 
 
 do. 
 do. 
 
 do. 
 fifth 
 
 fourth 
 do. 
 
 do. 
 
-45- 
 
 Table  4-  —(Continued) 
 
 Compound 
 
 Insect 
 
 Stage  1/ 
 
 Trig(p~afflinophenyl)cerbinol   Greenhouse  leaf  tier 
 (KSgCgH^COH 
 
 Xanthone 
 
 96%ooc6%9 
 
 Southern  arnyvorn 
 
 Fifth 
 
 Fourth 
 
 Xanthydrol 
 
 C6^CH(OH)C6H1|0 
 
 H-(  2 , 6~Xylyl)  f ormaaide 
 HC0NHCgH,(CH,)2 
 
 do, 
 
 Melon-worm 
 
 do. 
 
 do. 
 
-46- 
 
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