Laboratory tests of toxicity of additional organic compounds to the European corn borer

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Material Information

Title:
Laboratory tests of toxicity of additional organic compounds to the European corn borer
Physical Description:
25 p. : ; 26 cm.
Language:
English
Creator:
Questel, D. D ( David Dewitt ), 1899-
Gertler, S. I
United States -- Bureau of Entomology and Plant Quarantine
Publisher:
United States Department of Agriculture, Agricultural Research Administration, Bureau of Entomology and Plant Quarantine
Place of Publication:
Washington, D.C
Publication Date:

Subjects

Subjects / Keywords:
European corn borer -- Biological control   ( lcsh )
Organic compounds -- Testing   ( lcsh )
Genre:
federal government publication   ( marcgt )
non-fiction   ( marcgt )

Notes

Additional Physical Form:
Also available in electronic format.
Statement of Responsibility:
by D.D. Questel and S.I. Gertler.
General Note:
Caption title.
General Note:
"E-707."
General Note:
"November 1946."

Record Information

Source Institution:
University of Florida
Rights Management:
All applicable rights reserved by the source institution and holding location.
Resource Identifier:
aleph - 030292613
oclc - 780067549
System ID:
AA00026076:00001

Full Text

6ovember 1946 E-707







I United States Department of Agriculture
Agricultural Research Administration
Bureau of Entomology and Plant Qiarantine

LABORATORY TESTS OF TOXICITY OF ADDITIONAL ORGANIC COMPOUNDS
TO THE EUROPEAN CORN BORER

By D. D. Questel, Division of Cereal end Forage Insect Investigations,
and S. I. Gertler, Division of Insecticide Investigations

This report contains the results of laboratory tests with
various organic compounds against newly hatched larvae of the
European corn borer (Pyrausta nubilalis (Hbn.)) at Toledo, Ohio,
during the period from 1938,to the present. Similar tests against
newly hatched corn borer larvae have been reported in publications
3-557, z-612, and z-620 of this Bureau. All the compounds were
supplied by the Division of Insecticide Investigations, and have
recently been decoded.

The care and handling of moths, eggs, and larvae for these
tests and the technique employed in conducting them are described
in E-557. Materials were tested as sprays on fresh, green cauli-
flower leaves at the rate of 4 pounds of the compound per 100
gallons of water containing 1/3 pound of Areskap (sodium monosul-
fonate of butylphenylphenol) as a wetting agent. Materials showing
high mortality with little or no feeding were retested at 2 pounds
and 1 pound per 100 gallons of water. Larvae in all tests were
given an opportunity to feed for 48 hours prior to taking mortality
readings. Results of these tests are given in tables 1, 2, and 3.

When tested at the rate of 4 pounds per 100 gallons of water,
12 compounds gave 100 percent kill. Of these compounds 9 continued
to show 100 percent mortality when tested at 2 pounds per 100
gallons of water. At the rate of 1 pound per 100 gallons 8 compounds
gave mortalities ranging from 90 to 100 percent.













NOV 2 7 1946





-2-


Table l.--Tests at 4 pounds per 100 gallons of water
Larvae Average percent
used in mortality Amount
treat- Not of
-.C- ound mentl/ Treated treated feeding
Bi s( 5-chloro-2-hydroxyphenyl)methane
(06H3C1(OH))2CK2 52 100.0 2.0 0-++
1 -Trichloro-2, 2-bis(3, 5-dichloro-
2-hydroxyphenyl) ethane
cl 3CCH(CH2Cl 01H) 2 6S 100.0 1.3 0
Chloromethyl-4-chlorophenyl sulfoneJ/
d04SO0 2CH201 61 100.0 1.0 0
2-I sobutyryl-l-phenylhydrazine
Og6HSKNHGOCHC( H )2 147 100.0 0.4 0
alpha, alpha, alpha, 2, 5-Penta-
chloroacetanilide
0621Cl2NHCOCC13 92 100.0 1.3 0
1-Pheny -2- sul finylh-ydrazine
gHRHN: SO 15g 100.0 0.7 0

1-Isovaleryl-2-phenyIlhydrazine
C6HSlNHOOCH2CH(CH3)2 129 100.0 0.9 0

1-I socaproyl-2-phenylhydrazine
C 6H 5" Ncc(cH2) 2CH( C3)2 122 100.0 0.9 0

l-Phenyl-2-valerylhydrazine
O g5NHNCOC(CH2)33 115 100.0 0.9 0

alpha, alpha, beta-
Trichlorobutyramide
CH3COC1CC120Q22 119 100.0 1.3 0

l-Dichloro-2, 2-b is(p-chlorophenyl )-
ethane
(C106H4) 2CCHC12 227 100.0 1.7 0

l-Phen1:l-2-phenyl sulfonylhydrazine
C6~iNHNHSO2C6H5 139 100.0 0.4 0

l-Phenyl-2-(p-tolylsulfonyl)-
bydrazine
C6HSNHx SCg6H4CH3 164 99.5 0.7 0



/ Approximately the sar.e nTunber of larvae were used in the non-
treated checks.
2 0, none; +, little; ++, moderate; +++, much.
/ These compounds had been mixed with equal parts of kaolin and
were tested at the rate of 8 pounds of the mixture or 4 pounds
of the compound per 100 gallons of water.





-3-

Table l.--(Continued)
Larvae Average percent
used in mortality Amount
treat7 Not of
Compound menti/ Treated treated feeding
2, 4-Trichloromethyl-s-trioxane
CC1iCHOCOH20H(0013)0 194 99.0 2.0 0-+

l-Trichloro-2-(p-chlorophenyl)-
2-phenylethane
(Cll6H5)(c6H5) 0Hcc3 187 98.9 1.0 0

N-(3,4-Methylenedioxythio-
benzoyl)morpholine
CHg2C6Hg3CSN(CHa2C2) 20 185 96.5 0.7 0-++

Chloromethylphenyl sulfoneX
O6HSS02CH2Cl 48 95.8 1.0 +

1-Acetyl-2-phenylhydrazine
O6H4iCiHOOCH3 206 95.4 0.9 0-+
l-Butyryl-2-phenylhydrazine
06H5 MNHC0C3H7 187 95.3 0.9 0-+
l-Cimnamoyl-2-phenyllhydrazine
C6H5NMHHCOOH=aHC6H5 113 94.5 0.9 0-+
p-Chloro-N-propylbenzene-
sulfonami e
lC6H4SO2i1O3H7 220 94.4 1.5 0-+
N-Thiobenzoylmo'rpholine
0gH0cS( CN(H I12)20 l 93.9 0.7 0-+
5-(3-Methylbenzylidene)-2-
thio-4-thi azolidone
cH3C6H40H=Cso(S))NHOO 187 93.6 0.7 0-+

l-Trichloro-2,2-bis(5-chloro-2-
hydroxyphenyl) ethane
0130CH(C6Hs5H0C)2 56 92.2 1.3 0

alpha, alpha, alpha, 2,4-
Pentachlorotoluene
06H3012(0013) 156 92.5 2.0 0-+




-4-


Table 1.--(Continied)
Larj Average -perces:t
used in m ortalit' Amount
trent- NTot of
Compound met/ ed treaed eedi

p-Bromo-N, N-dimetllyber.nzene-
sulfonanide
BrC6H4SOi( CH3 2 233 91.9 1.5 0-++

Ben zylphenylnitro soamine
C6{ON(NO)CH2C6H5 351 90.5 0.7 0-

l-Phenyl-2-phenylac ety lhy dr azine
C 6H .2nn1ocCH26H 5 60 90.4 1.3 0

EI-Anil inc-ilpha-tolunm id.e
c 6H5CCH2on2CH 65 152 S8.6 i.4 0-+

5-Is obutyl-l-phenyl senlox;mnazide
c H5:'ImCOCCcmCH2CHH(CE3)2 94 F7.3 1.1

alpha-( 1-Pip crid yl)-p 7pha-
tilu, itt rile
CH 5ICH( 0C)C04ll 22 74.5 1.0 0-o-++

s;?mn-Di-a;-tol 2t ionrea
(CYH 3C^GaH)2S 220 b7.4 O.S 0-

9-1itro-2,4-bi (t ri chl o ronme th'l)-
1, 3-ben zodioxane
gH(oc2)oH(c )C2CR(CCl3) 260 67.0 1.2 0-

p-Nitrc-enzoic acid, etiyl epter
S2 "CO' .C.. 1)12 66.8 1.4 0-.*


15c fS *. 1."2, +++

-.,i':C HQ l4"i 58.6 0.6 0-++

,J*( t I'tler- dio:yth Aiobenzoyl)-
Swoeridine
002C6H3( 5H10o 153 54.7 07 0

N-Ethylphthalimride
U61140) i 0H5 1i2 49.2 1. 0-+-,+





-5-


Table l.--(0ontinued)
Larvae Average percent
used in mortality Amount
treat- Not of
Compound mentl/ Treated treated feeding
p-Nitrobenzoic acid, propyl esterl
NO20640000CH 132 49.1 1.4 -+++
4-Chloro-2-nitroani sole
06H3(OCH3)0lO2 95 46.9 1.9 +++
3-Nitrobenzan 1 ide
C6H4(No2)CONHoH5 109 41.o 0.4 +-+++
2.4-Bia(trichloromethyl) -
nitro-1, 3-benzodioxjaneW
O2Cg6H30CH( CC13 )OH(CC13) 77 39.5 0.0 +++
N-Anilinophthalamic acid
c6H4(co0H) commq6H5 111 35.8 0.7 +++
N-Anilinocinnamamide
CgHr5CGsHCOmHHC6H5 133 34.6 1.4 +-+++

N-Anilinophthalimide
06H4( ) )2mHc605 142 34.5 o.7 +++

l-(p-Nitrophenyl)piperidine
0 510NC 6HO2 250 34.4 i.0 0-+++
2-t hoxalyl-l-phenylhydrazine
C6Hj~E ORcOCoOC H5 135 33.7 .3 ++-+++
2,2-Thio-bi b(4-chlorophenol)3'
(06H30o012) 2S 135 31.0 J.6 ++++
1, l-Cyclohexane-4, 4-bi ( 2,6-
dichlorophenol)Ij
C6Hlo(C6H 2HCl2)2 102 29.8 0.8 ++
N-(3, 4-Dimethoxythiobenzoyl) -
morpholine
(caHo) 2c630cs(CH2gCH2) 130 27.6 0.5 ++

1-Dichloro-2,2-bia(p-chlorophenyl) -
ethylene
(Cl06H4)2C=0Cl2 123 27.1 1.9 +++






-6-



Larvae Average percent
used in mortality Amount
treat- Not of
morpound mentl/ Treated treatedI feeiin
2J;pa-(p-Bromoanilino)al; .l-
tolnitrile
3rCII: IiGH(cH)O6H5 167 24.5 1.0 +-

Bi s( 4-chlo ro-3-n.i trophenrl)-
ualfone
((0630c'02) 2302 79 23.9 1.8 +++

N-PXropylTphthalimi de
c6O4(0o) 2c37 109 23.0 1.9 ++-+++

14-(o-Hydroxybenzyl) morpholine
CgH4(OH) c ( CHO2) 2CH2H2 87 22.9 1.8 +++

2-(p-Ni t robenzoyl)-l-phenylhydrazine
Cs6N coc~6 i 2 37 22.7 0.4. ++

p-Nitrob nzoic acid, isopropyl
ester-3
NO2C6H40OOCH(C {3)2 135 18.8 1.4 +++
l-Trib romo-2, 2-bis(p-bromophenyl) -
ethane
(BrOC;H) 2CHCBr3 55 16.3 1.8 ++

N-Aml1-i-n-itrobenzami de
cGO4(Nog2) ooM H511 107 15.0 0.4 +-+++

N-sec-Butyl-m-nitrob enzamide
c6H1(NO2) CGOHCH( CH3) 2H5 118 14.9 1.8 +++
2,4-Dichlorooxanilic acid,
ethyl ester
12C63liCOCOOC 2 5 103 14.4 2.1 +++

Bis(2,4,6-trichloro-3-
hrdroxyphenyl) methane
CH2(CHOHC13)2 43 14.1 1.3 +++

Acetic acid,alpha-(trichloromethyl)-
benzyl ester
06H5GH( COl3)0000H3 55 13.4 1.3 ++





-7-

Table l.--(Continued)
Larvae Average percent
used in mortality Amount
treat Not of
Compound mentI- Treated treated feeding2/
3,4-Dichlorobenzoic acid
06H3CI2000H 66 10.0 1.8 +++

2-Methovy-6-nitrobenzoni trile
a0H3C6H3(N02)ON 194 9.7 2.4 +++
N, N-Dii sopropyl-p-nitrobenzamide2/
N0206H400N( H(CH3) 2)2 162 9.7 0.6 0-+
N, N-Dipropyl-p-ni trob enzari del
MP26HsaO(03 47)2 128 9.3 0.6 ++-*+
o-Hrdroxy-alpha-(l-piperidyl)-
alpha-tolunitrile
S5H10oNH(CN)C640H 107 9.0 1.6 +++

l-Tribromo-2, 2-bi s(p-chlo ropheny ) -
ethane
(clO614) 2CHBr 69 8.9 1.8 +++
N-Phenylglycinonitrile
06H5 HH2NON 103 8.1 1.6 ++4
l-Dibromo-2, 2-bi s(p-chlorophenyl)-
ethane
(C1C6H4)2CHGHBr2 91 7.1 1.8 +++
p-Chlorooxanilic acid, eth'1 ester
C10CH4NHoCOOOO25 98 6.9 2.1 +++
3, 4-Di ohio ro-N-met hylb en zami d
c6H3O12OONHCH3 95 6.4 0.0 +++
3,4, 6-Trichloro-alpha-(2,3,5-
trichloro-6-methoxyphenyl)-
o-cresol11
OgH01 ol3 H2O2 013OCH3 106 6.4 1.0 +++
alpha, alpha'-Hexachlo ro-o-xylene
c6H4(c013)2 271 6.1 2.4 ++
2, 2-3 s(p-acetoxyphenyl)-l, 1,1-
trichloroethane
(CH00006H4) 20HCC13 101 5.7 2.5 +++





--.


Table 1.--(Continued)
Larvae Average percent
used in mortality Amount
treat- Not of
Compound_ ment/ Treated treated feeding
alpha, alpa'-Hexachloro-p-
xylene.
C6H4(0013)2 107 5.6 1.8 +++
p-Ni trob en zyhydrazide
1o 20 6H4C0NH 2 259 5.0 2.7 +++
N-sec-Butyl-p-nitrob en zamide~/
NO C6H0CONHCH( CH5)CH3 99 5.0 1.2 +++
alpha, alpha, alpha, 3 4-
Pentachlorotoluene2/
C6H3C12(0013) 162 4.8 1.8 +++
2,3-Dihydro-3-phenyl-1,4-
phthalazinedione
G04H4C()NN(11 H5)co 156 4.7 0.7 +++
2, 2-Sulfonyl-bis(4-chlorophenl)) /
(06H30HCI)2so2 87 4.7 0.0 +++
Benzenesulfonic acid, m-
nitrophenyl ester
C6H5SC 3C6H402 94 4.6 0.8 +++
m-Ni tro-N-propylb enzai de
0 H NO 2) CONHCh 104 4.6 1.8 +++

1-Phenyl-5-propylsereioxamazide
Cg6HNHNHCOONH3H7 107 4.5 1.1 +++

N(2,5-Dichlorophenyl)phthalimide
C6H(0) 2N06301 104 4.4 1.6 +++
2-Anthroic acid
06H4:(OH) 2: C6H3OOH 66 4.4 1.8 +++
N-Methyl-2-naphthalene sulfonamide
010oH7SO2NHCH3 104 4.3 2.1 +++
2,4-Dinitro-4 '-methoxystilbene
G6H3(NO 2) 2CH:=H0 6H40CH3 105 4.2 1.5 +++

1,1-Methyl ene-di-2-naphthol12
CH2(C1OH60H)2 100 4.2 1.0 +++





-9-

Table l.--(Continued)
Larvae Average percent
used in mortality Amount
treat- Not of
Compound menti/ Treated treated feeding
N-(m-Nitrophenyl)phthalimi de
06H4(00)) 2C06R402 93 4.1 1.0 +++
N-(2-Naphthyl)phthalimide
C6H4(cO) 2NC107 113 4.0 0.7 +++
N-I sobutyl-m-nit rob enzami de
OgH4(NO2) CONHCH2OH(CH3)2 77 4.0 1.8 +++
Gentralite
(C 6EN(OH5)) 20 113 3.9 1.5 +++
5-3utyl-l-phenylsemioxamazide
C6H5NHHCOCONHC4H9 100 3.8 1.1 +++
Bis(3,5-dichloro-2-hydroxyphenyl)-
methane
(Q6H2012(OH)) 2 2 79 3.8 2.5 +++
alpha, alpha, alpha, 4-
TetrachlorotolueneaI
c016H4CC13 123 3.6 1.5 +++
1-(2, 5-Dichlorophen;l)urea
C6H31 2NHCONH2 114 3.6 0.8 +++
p-Toluenesulfonic acid,
o-nitrophonyl ester
OH3C6H4SO206H4NO2 140 3.4 1.5 +++
alpha,alpha-Dichloropropionamide
CH3c01 CONH2 142 3.4 1.3 +++
2,2-Bis(p-hydroxyphenyl)propane
(06H40H) 20(C3)2 110 3.3 1.8 +++
N-I sobutyl-p-nitrobenzamidelZ
NO2C6H4CONHH20H(CH3)2 102 3.3 1.2 +++
p-Oy clohexylsul famylacetanilide
CH3OO ~ 00 4S0NHCH(OH2)4 H2 95 3,2 1.2 ++

alph&-alpha-alpha, 2-
Tetrachlorotoluene
OlC6H4OC13 99 3.2 1.5 ++





-10-




SLarvae Average percent
used in mortalit;y Amount
treat N'ot of
C__ r1ment4 Treated treated i feedin
o-Chloro-N-meth1ylbenzamid
C6H4CICC!,ICH3 96 3.1 0.8 +++
N-Propylcinnamamide
C6H5OHC1COcHOc3H7 99 2.9 1.2 +++
N-Met'l,-p-ni trobenza-nide
C 4(NOg2) COHCH3 135 2.9 1.2 4-+
alpha- (Trichloromethyl )benzyl
alcohol
C6H5CHOHCC13 s8 2.8 1.3 +++
p-Toluenesulfdnic acid,
m-nitrophenyl ester
CH3060CSO 2oc6HO2 152 2.8 1.5 +++
2,2-31s(p-tert-butylphenyl>-
1-trichloroethane
((ca3) 3CC6H4) 2CHCCl3 149 2.7 1.1 +.H
p-Nitrob nzoic acid, isobutyl
ester-2
NO2C6H4COOCH2CH(CH3)2 159 2.7 1.4 +++

p-Nitrobenzoic acid,
2-chloroethyl esteriU
N02C6H41COOcCH2CH2 97 2.7 1.2 +++

3,4-Dichlo rotoluene
C6H3(CH3) 012 10 2.7 1.8 +++
1-Naphthyl phenyl ketone
C0lH7COC6H5 69 2.7 1.8 +++
Hydroquinone dibenzenesulfonate
Cg65S03c6H03Sc6H5 91 2.6 0.0 +++
alpha-Anilino-alpha-tolunitrile
C6H5NHH(CN)c6H5 121 2.6 1.6 ++
2,4-Dinitro-3',4'-
methylenedioxystilbene
C6H3(NO2)2CH=GH" 6H3(02CH2) 123 2.4 2.1 +++
N-Isopropylcinnamamide
cGH5cHHCONHCOi(CH3)2 84 2.4 1.2 +++





-11-


Table 1.--(Continued)
Larvae Average percent
used in mortality Amount
treat- Not of
Compound mentl/ Treated treated feeding/
2,6-Bis(trichloromethyl)-1,3,5,7-
tetroxocyclooctane
C1, H OC200GH(CC1 )OCH20 82 2.2 2.5 +++

Benzenesulfonic acid,o-nitrophenyl
ester
C6H5so3C6HO2 94 2.2 0.8 +++
N-(Hydroynmethyl )benzamide
og5HONHCO20H 85 2.2 1.8 +++
Benzenesulfonic acid,p-
nitrophenyl ester
06H5SO3C6H4N02 96 2.2 0.8 +--

Benzeneaulfonic acid, 2,4,6-
trichlorophenyl ester
06H530306H2013 95 2.2 0.8 +++
3,4-Di chloro-N-ethylbenzamide/
C6H3Cl2O0NHC2H5 136 2.2 0.0 +++
N-Propyl-p-ni trobenzamidel/
NO20cg H4COM C3H7 97 2.2 1.0 +++
N-Octylphthal Imide
C6H4( CO) 2 OH17 94 2.1 1.0 +++
N,N '-Bis-(p-chlorophenyl) oxamide
C1C6HQHOOCONHO6HC01 106 2.1 2.1 +++
N-Amylcinnamamide
6 CgH5CoHCONiC5H11 102 2.1 1.8 +4
2 '-hloro-3-nitrobenzanilide
O6H4(NO2)COITO6H4C1 105 2.1 0.8 +++
p-Methoxy-beta-nitrostyrene
C6H4(OOH3)CH=H0IMO2 91 2.0 1.5 +++
1-(o-Nitrophenyl)piperidine
C HloNCGHWo2 103 2.0 1.6 +++
N,N-Dicyclohexyl-m-nitrobenzamide
6H4(NO2)CON(06H11)2 110 2.0 0.8 +++






-12-


Table l.--(Continued)
Larvae Average percent
used in mortality Amount
treat- Not of
Compound mentl/ Treated treated feeding&/
N-Cycl ohe ql-m-ni trob enzami de
C6H4(NO2) CONH6H11 106 2.0 0.8 +++
N-sec-Butylcinnamamide
C6H5C0H=CCOCNHC(CH)CH02H 94 2.0 0.8 +++
p-Propylsulfamylacetanilide
CH CONHC 614SO2NHC 3H 103 2.0 1.2 +++
N-Ethyl-2-naphthalenesulfonamide
Co H7SO 2NHC2 5 s 1.9 0.5 +++
Sulfonal
(C 3)220(so202H5)2 143 1.9 1.7 +++
1-Dibrono-2, 2-bis(p-bromophenyl) -
ethane
(rrCO6H) 2CHCHBr2 102 1.9 1.8 +++
2-Trichloro-l-(2,4-
dihydroxyphenyl) ethanol1/
C6H3(OH) 2CH(CC13)OH 111 1.9 0.0 +++
alpha,beta-Dibromosuccinic acid
HOOCCHBrCHBrCOOH 106 1.9 1.1 +++

2-(Diethylamino) ethyl
pentachlorophenyl ether1/
C6C150CH2CH2N(2H5)2 111 1.3 0.6 ++
3,4-Dichlorobenzamide2l
C6H3C1 2CONH2 09 1.9 0.0 +++
N-(2-(2, -Dinit ;phenoxy)ethyl)
dibenzyl aninedJ
CH3(NO2)20CH2CH2N(H2CC6H )2 102 1.9 0.8 +++
6-Chloro-2, -dihydroxynicotino-
nitrile
NC5HC1(OH)2CN 125 1.8 1.8 +++
2,4-Dinitro-N-isopropylaniline
(NO2) 2 6H3NHCH(3)2 117 1.8 1.9 +++
Benzenesulfonic acid, 4-tert-
butyl-2-chlorophenyl ester
C6H SO3C6 I3CC(CH3 ) 112 1.8 0.0 +++





-13-

Tsble l.--(Continued)
Larvae Average percent
used in mortality Amount
treat- Not of
Compound ment.1/ Treated treated feeding&/
2, -Dini tro-4 '-hydroxy-3-
methocystilbene
C063(N02) 2CHCHC6H3(OCH3)(OH) 124 1.7 1.5 ++
l-(l-Hydroxy-2-trichloroethyl)-2-
thio-3-(2-trichloroethylidene)urea
(CC13CHOH)n nC(S)N=CHCl13 92 1.7 1.2 +++
Benzenesulfonic acid, m-tolyl ester
C6H5So3C6j4CH3 101 1.7 0.8 +++
p-Nitrobenzoic acid, methyl esterl/
NO2C6H4COOCH3 103 1.7 1.2 +++
1, 3-Bis(l-hydroxy-2-
trichloroethyl)urea
C0(YHCHOHCC13)2 126 1.6 1.2 +++
p-Aminobenzophenone oxime (anti)
Cg5bC(NOH)C6H4NQO2 150 1.6 3.1 *++

l-Trichloro-2 2-bis(3,5-dichloro-
4-methoxyphenyl) ethane/
C13CCH(C6H2C120CH3)2 77 1.6 0.0 +++
N,N'-Dibenzyl-N'-(2, 5-diclloro-
phenyl ) ethyl enediamineJ/
O6H3Cl 2RCH2CH2N(CH2C65) 2 129 1.6 0.8 +++
N-I sopropyl-m-nitrobenzai de
6gH14(NO2)CONHCH(CH3)2 85 1.5 1.8 +++
N-Ethyl-p-nitrobenzamide./
C H4(O2) CO~HC025 135 1.5 1.2 +++
3,4-Methylenedioxy-beta-
nitrostyrene
(CH20 2)C6H3CIHCEHO 110 1.5 2.1 +++
N-(5-Nitro-o-tolyl)phthalimide
C6H4(Co)2NC6H3(NO2) j3 133 1.5 1.0 +++
Dime thox'b enzoni trile
(CH30)2C6H3CN 200 1.5 2.4 +++






-14-


Table 1.--(Continued)
Larvae Average percent
used in mortality Amount
treat- 1ot of
Comound ____ menti/ Treated treated feeding,
p-Toluenesulfonic acid,
o-nitrophenyl ester
H3C 6"4S 3C6H4N02 136 1.5 0.7 +H+
Pyrocatechol diacetate
c6T( ccocC3)2 75 1.4 0.0 +++
alpha-(p-To.luino)-alpha-t oluni trile
CH30 % 6H1CH(CN)c6H5 78 1.3 1.6 +++

2,4-Sulfonyldiphenol/l
(C6H4OH)22C2 83 1.3 1.2 +++
Tetrachloroquinone
C:C6C140 160 1.3 0.7 +++
Benzenesulfonic acid,
p-bromophenyl ester
C6HSSO3C6H4Br 92 1.3 0.0 +++

alpha- (1-Naphthyl m ino) -alpha-
tolunitrile
ClH7OTHCH(CN) CH5 78 1.2 1.6 +++
l-Trichloro-2,2-bis(3,4-dimethoxyphenyl)-
ethanel/
cl3CCEH( C63(OCH3) 2)2 73 1.2 0.0 +++

m-Nitrobenzoic acid, 2-(2-pyridyl)-
ethyl esteri/
NO 2CG6HCOO2CHH2C5H4N 98 1.2 0.8 +++
N-Isopropyl-p-nitrobenzami del
N02C6H4CCONHCH( CH3)2 81 1.2 1.0 +++

N, N' -Dibenzoylmethanediamine
(c 5CONH)2 H2 124 1.2 1.8 +++

N-(m-Chlorophenyl)phthalimide
c6Hi(co), c6gHCl 87 1.1 0.7 +++
N-1-Naphthylphthalimide
cgh4(CO) 2NCooH7 94 1.1 0.7 +++
N-Benzylphthalimide
C6H4(C0) 2NCH2C6H5 105 1.1 1.0 +++





-15-


Table 1.--(Continued)
Larvae Average percent
used in mortality Amount
trea7 Ntot of
Compound_ ment-_ Treated treated feeding2/
4-(3-Chloro-2-hydroxybenzyl)
morpholine
C063(Cl)(OH)CH2N(CH2)20CH2CH2 75 1.1 1.8 +++
o-Cyanobenzamide
6Hi4(CN) COH2 206 1.1 0.0 +++
N-(4-Hydroxy-3-methoxythio -
benzoyl)morpholine
(CHO) (HO) O6H3CS ( CH2C2) 2 112 1.1 0.8 +++
l-Trichloromethyl-4,4'-met lene-
bis-(2 6-dichlorophenol).7
CC03cH CCH20HC12)2 108 1.1 0.0 +++
Trithianel/
SOCSH 2SC H2 98 1.1 0.0 +++
p-Nitrobenzoic acid, phenyl esterf/
NO20~400OC60 105 1.1 0.8 +++
N,N-Dimethyl-2-naphthalene-
sulfonamide
0107S02N(CH3)2 108 1.1 0.8 +++
2,4-Dinitrostilbene
C063(No2) 20H=HC6H5 94 1.1 1.5 +++
alpha-( o-Ani sidino)-alpha-
tolunitrile
CH306H4NHOOCNC06H5 126 1.0 1.2 +++
N-(o-Arnisyl)glycinonitrile
CH3oc6H4OHCH2gC 94 1.0 1.2 +++
4-( 5-Chloro-2-hydroxybenzyl)
morpholine
C6H3(C1)(OH)CH~N(CH2) 20CHH2 75 1.0 1.8 +++
N-Butylcinnamamide
CO 5CH-CHOOH04H9 118 1.0 1.2 +++
Benzenesulfonic acid, p-tert-
butyl-phenyl ester
06H5SOC6H140(COH3)3 109 1.0 0.0 +H






-161


Table 1.--(Continued)
Larvae Average percent
used in mortality Amount
treat7 Not of
Compound ment-/ Treated treated feeding/
p-Bromobenzenesulfonic acid,
p-nitrophenyl ester
NO2C6H4SO20C6H4Br 125 1.0 1.5 +++
Trional
CH3C( SOC202H5) 2C2 171 1.0 1.7 -++

p-Toluenesulfonic acid,
p-nitrophenyl ester
CH 30640S 200C64NO2 209 1.0 1.5 +++

Benzoic acid, 4-chlorophenyl ester
C65COOC6H4C1 181 1.0 0.7 +++
Benzenesulfonic acid, 2,4-dinitro-
phenyl ester
C6H5S3C6H3(T02) 2 94 1.0 0.0 +++
alpha-Tri chlorotoluene3/
C6H5CCl3 103 1.0 1.8 +++
5-Carbethoxy-6-methyl-4-phenyl-2-thio-
1,2,3 4-t etrahydropyrimidine
NHC(S)NHCH( Cg5)( C02C 5)C(CH3) 117 1.0 0.9 +++
N-p-Tolylglycinoni trile
C6H4(CH3)NHCH2CN 94 1.0 1.6 +++
2-(Dibenzylamin9)ethyl pentachloro-
phenyl etherX2
C6C15qCH2CHN(C6H5CH2)2 90 1.0 0.6 +++
p-Nitrobenzoic acid, benzyl esterS./
Ni02C6H14C00 2C6H 5 102 1.0 1.2 +++
o-Chloroben zamide./
C6H4c10ONH2 118 1.0 0.8 +++
2,2-Methylene-bis(4-chlorophenol)
diacetat 2J
CH2(CH3COOC6H3C1)2 101 1.0 1.0 ++-+++
N-(2-Hydroxyethyl )phthalimide
C6H4(CO)2NCH2CH20H 125 0.9 0.7 ++
4-(m-Nitrobenzoyl)morpholine
CH2CH2( CH2) COCGH402 114 0.9 0.8 ++





-17-


Table 1.--(Continued)
Larvae Average percent
used in mortality Amount
treati Not of
Compound __mentit Treated treated feeding
N-Methyl-alpha-toluamide
CgH0CH2CONHCH3 104 0.9 0.0 +++
N-Methyl-m-nitrobenzamide
OgH4(NO2) CONHCH3 192 0.9 0.7 +++
p-Chlorobenzamidel/
O6H4C 1CONE2 95 0.3 0.8 +++
p-Nitrobenzoic acid,2-(2-puridyl)-
ethyl ester J
o 20 6HC00 H2CH 2C51'4l 120 0.9 0.8 +++

N-(n-Propyl)-2-naphthalene-
sulfonamide
10oH7SO2NHC3H7 107 0.9 0.8 +++
Benzenesulfonic acid,1-naphthyl ester
Cg0RS03coH7 112 0.9 0.0 +++
l-Trichloro-2,2-b is(p-hydroxyphenyl)-
ethane
(HOC46H) 2CHCC1 108 0.8 0.8 +++
p-Metho y-alpha-(1-piperidyl)-
alpha-tolunitrile
C5HloNCH(ON)C6H40CHE3 97 O.8 1.6 +++
p, pTMethylenedianiline
(N2C6H4) 202 119 0.8 1.0 +++
1-(l-Hydroxy-2-trichloroethyl)urea
cc13 COHNHC(0)NH2 119 0.8 1.2 +++

3-Chloro-alph$(pentachlorophenoxy)
acetanilide21
Cl 50CH2COoN6HCl 123 0.8 0.8 +++
l-Trichloro-2, 2-bis(3,5-d chloro-
2-methoxyphenyl) ethane-/
o13CCH(C6H20120CH3)2 102 0.8 0.0 +++
N-(o-Chlorophenyl)phthalimide
H4(CO)2Nc6H401 122 0. 0.7 +++






-18-


Table 1.--(Continued)
Larvae Average percent
used in mortality Amount
treat Not of
omound_ ment/ I Treated treated feedi
N-(m-Tolyl)phthalimide
C6H4(CO) 2NC H4CH3 120 0.8 1.0 +++
N-Cyclohexylphthnliride
CGH4(C0)2NC6H11 118 0.3 0.7 +++
Benzenesulfonic acid, p-tolyl ester
CgH5o3C6H CH3 119 0.8 0.8 +++
p-Toluenesulfonic acid,
m-notrophenyl ester
CH3C6H4SO 306H4NO2 110 0.8 0.7 +++
p-Toluenesulfonic acid,m-tolyl ester
GHC6H4SO3C6H4CH3 154 0.7 0.7 +++

N, N-Dimethyl-p-nitrobenzamidel/
C06H4(O2) 0ON(CH3)2 139 0.7 1.2 +++
o-Chloro-N-ethylb enzamide-/
C6H4C1CONHC2H5 108 0.7 0.8 +++

1,Trichloro-2, 2-bis(5-chl9ro-
2-methoxyphenyl) ethane-
C13CCH(C6H3oCH3Cl)2 150 0.7 1.2 +++
2, 2-Dithiobisbenzothiazole
(SC6H4N:0C)2 124 0.7 1.1 +++
p-Toluenesulfonic acid,
2-naphthyl ester
CHJ3C6SO 3Co1H7 125 0.7 0.7 +++
p-Diethylsulfamylaceta.nilide
CH3CONH06g4SO2N(C2H5)2 137 0.7 0.8 +++

N, N-Diethyl-2-naphthalenesulfonamide
C10TOH2N(C 25) 2 107 0.7 0.8 +++
4, 4-ulfonyldiphenol-l
(C6H40H)2S02 95 0.6 1.2 ++-
1-(m-Nitrobenzoyl)piperidine
CH2(CH2)4NCO0C6H4N02 102 0.5 1.8 +++
i, 2-Dihydro.-l, 4,6-trimethyl-2-
oxonicotinonitrile
(CH 3)2C5HT(CH3)(o)CN 180 0.4 0.0 +++






-19-


Table 1.--(Continued)
Larvae Average percent
used in mortality Amount
treat- Not of
Compound menti/ Treated treated feeding2
9,10,11,15-Tetrahydro-9,10-( ', 4)-
furano anthracene-12 14-dione
cg6 H4HCHCHCGCHC(O)OC(O) 191 0 0.7 +++
N, N-Dimethyl-m-nitrobenzamide
COH4(NO2)CON(CH3)2 117 0.4 0.7 +++
4-Cyano-2,4-dihydro-2-(o-hydroaxphenyl)-
3-phenyl-l, 3-benzisoxazine
C6H4CH( CN)N( C6g) CE( C_6H40H)O 98 0.0 0.0 +++
N-Butyl-m-nitrobenzamide
C64(NO2)O) HCo4H9 85 0.0 0.8 +++
p-Chloro-N, N-dimethylbenzamidel/
6H4ClccN( CH3) 2 108 0.0 0.0 +++
p-Chloro-N-methylbenzamidel/
C6H4ClCONHCH3- 89 0.0 0.8 +++
p-Nitrobenzoic ai d, tetrahydro-
furfuryl esterJ
NOO26H4COOCCHGH2CH2C2OH2 103 0.0 0.8 +++
N, N-Diethyl-p-nitrobenzamideL/
020C4QCON02 )2 82 0.0 1.0 +++
p-Nitro nzoic acid, cyclohery1
ester-l
NO 20 640OO00611 103 0.0 0.8 +++
1-Trichloro-2,2- is( 2,5-dimethoxy-
phenyl) ethane2/
13CCH( CH3(OCH3)2)2 118 0.0 1.2 +++
l-Trichloro-2-phe~y1l-2-
b iphenylethane2/
CgH5CH( CC3) C6H406H5 72 0.0 0.0 +++
N-(2-Trichl9yo-1-hydroxyethyl)
benzamide.
C6H5CO0HCHOHCC13 78 0.0 0.0 ++
N-(p-Tolyl)phthalimide
CGH4(C0)2NC6H4CH3 77 0.0 1.0 +++
N-(o-Nitrophenyl)phthalimide
CO6H4( )2NC6H4NO2 97 0.0 1.0 +++


SATEL P^LAW OA-D





-20-


Table l.--(Continued)
Larvae Average percent
used in mortality Amount
treat7 Not of
Compound_ menti Treated treated feeding-
N-(o-Hydroxyphenyl)phthalimide
C64(CO) 2NC6H40H 87 0.0 1.6 +++
N-(p-Nitrophenyl)phthalimide
64(o(0)NCO) 2P N02 95 0.0 0.7 +++
Benzenesulfonic acid,
2-naphthyl ester
C065so3ClH07 92 0.0 0.0 +++
Benzoic acid, 4-tert-butylphenyl ester
C6H5QOOC 634C(CH3)3 136 0.0 0.0 +++
Benzenesulfonic acid, xenyl ester
C615so03C6gq 6H5 122 0.0 0.0 ++
Benzenesulfonic acid, o-chlorophenyl
ester
CgH5SO3C6H401 100 0.0 0.8 +++
p-Toluenemulfonic acid,
p-nitrophenyl ester
CH3C6i4so03 6HO2 115 0.0 0.7 +++
p-Toluenesulfonic acid, p-tolyl ester
CH3C64SO 3C640H3 123 0.0 0.7 +++
alpha, alpha', alpha"-
Nonachloromesitylene
C6H3(CC13)3 87 0.0 1.5 +++
N-Anilinomaleimide
,cCHoCHCCMHC6kH5 105 0.0 0.0 +++
Maleanilic acid
C6H5NHCOCH=CHCOOH 82 0.0 0.0 +++
N, N-Diisopropyl-m-nitrobenzamide
C6H4(N02)C0N(C(CH3) 2)2 86 0.0 0.0 ++
3 -Chloro-3-nitrobenzanilide
C0H4(N02)coHc6H401 88 0.0 0.5 +++
1-Phenyl-2-stearoylhydrazine
0.6H CgENO(CH2)16CH3 128 0.0 0.7 +++
(2-Trichloro-l-hydroxyethyl)carbamic
acid, ethyl ester
Ocl 3CHOHNHC( o0)C25 81 0.0 1.0 +++





-21-


Table 2.--Tests at 2 pounds per 100 gallons of water
Larvae Average percent
used in mortl itAj- Aaount
treaJ7 I-ot of
Compound ___ ment J Treated treated fee d6ln 2
1-Isovaleryl-2-phenylhydrazine
C6OI5KTCOOCHC2H(CH3)2 39 100.0 0.9 0
1-Trichloro-2,2-bie(3,5-dichloro-
2-hydroxyphenyl) ethane
C13coC(C062Cl20H)2 95 100.0 1.3 0
Chloromethyl-4-chlorophenyl sulfonel/
C016H4SO2H2C1 83 100.0 1.0 0
2-I sobutyryl-1-phenylhydrazine
C6H5N~HHcocH(CH-3)2 153 100.0 0.4 0
alpha, alpha, alpha, 2, 5-enta-
chloroacetanilide
C6H2C12 HCo0 13 92 100.0 1.3 0
l-Isocaproyl-2-phenylhydrazine
c6HfSNScO(CH2) 2c( C03)2 56 100.0 0.9 0
1-Phenyl-2-valerylhydrazine
C 6H 5Nh1iC( c2) 30C3 51 100.0 0.9 0
1-Dichloro-2,2-bis(p-chlorophenyl)-
ethane
(010cc6)2CHCHC12 37 100.0 1.7 0
1-Fhenyl-2- phenylsulfonylhydrazine
Cg6H5smso5g02 5 100.0 0.4 0
N-(3,4-Methylenedioxythiobenzoyl)-
morpholine
CH202CGH3CSTN(CH22) 20 134 99.3 0.7 0

l-Cinnamoyl-2-phenylhydrazine
C6g H HCOCH-CHg6H5 56 98.0 0.9 +

Bis(5-chloro-2-hydroxyphenyl) methane
(C6H3Cl0(OH))20C2 151 97.2 2.0 ++
2,4-Trichloromethyl-s-trioxane
CC13CHOCHOCOCH(CC1 )O 176 96.9 2.0 0-+

l-Phenyl-2-(p-tolylsulfonyl)hydrazine
C6H5NHNHS02C6H4CH3 135 96.5 0.7 0






-22-


Table 2.--(Continued)
Larvae Average percent
used in mortality Amount
treat- Not of
Compound ment_ Treated treatedme feedin
l-Phenyl-2-sulfinylhydrazine
C6HHS:EtSO' 171 92.9 0.7 +
N-Anilino-alpha-toluamide
C6H5CH2CONHNHC6H5 117 s8.6 1.4 0-+
alTh i, Plpha, alpha, 2, 4-
t chlorot oluene
SH 12( 01 C3) 155 84.2 2.0 ++
5-(3-Methylbenzylidene)-2-thio-
4-thiazolidone
CH C0H4CH=CSC(S)NHGO 119 80.2 0.7 +

Chloromethylphenyl sulfonell
C6gHSO2CHg2C 66 65.0 1.0 +
N-Thib enzoylmorphol ine
c65CSN(c02CH2) 20 89 63.8 0.7 ++
l-Butyryl-2 -phenylhydrazine
CgHo5 N COC3H7 150 60.1 0.9 +
1-Phenyl-2-phenylacetylhydrazine
CgH5NHINCOCH2C6H5 s8 59.4 1.3 +
p-Bromo-N,N-dimethylbenzenesulfonamide
BrC6H4SO0N( CH3)2 93 58.2 1.5 +++
N,N '-Dianilinooxamide
(C6H5MNRHCO)2 87 48.4 1.2 +++
l-Trichloro-2, 2-bis(5-chloro-2-
hydroxyphenyl)ethane
Cl CCH( C6H5HC1)2 80 43.8 1.3 ++-
N-( 3,-Methylenedioxythiobenzoyl)
piperidine
CH202g6H3CSNC5H10 114 43.1 0.7 +++
Benzylphenylnitrosoamine
C6H5N(NO) CH2C6H 79 36.7 0.7 +
f-Trichloro-2-(p-chlorophenyl)-
2-phenylethane
(C16gH5)(C6H5) CHCC3 114 34.4 1.0 +-++





-23-


Table 2.--(Continued)
Larvae Average percent
used in mortality Amount
treat- Not of
Compound mentL/ Treated treated feeding
5-Isobutyl-l-phenyl semioxamazide
C65NH5NHCOCONHCoH2CH(CH 3) 46 30.4 1.1 ++
alpha, alpha, beta-Trichlorobutyramide
CH3CHClCC12CONH2 106 29.6 1.3 +-++
N-Anilinophthalamic acid
06H4(COOH)CONHNHCgH5 46 26.1 0.7 +++
N-Anilinocinnamamide
C6H5CH=CHCONNHCg6H5 115 21.4 1.4 ++
l-Acetyl-2-phenylhydrazine
C6H5 cMHCOCH3 133 20.8 0.9 +++
sym-Di-o-tolylthiourea
( C3C gH4N) 2CS 137 20.0 0.8 +++

3-Nitrobenzanilide
gH4(NO2)CONHO6H5 78 11.4 0.4 +++
N-Amyl-m-nitrobenzamide
C6H4(N02)CONHCH11 64 11.0 0.4 ++
6-Nitro-2,4-bi s(trichloromethyl)-
1,3-benzodioxane
C6H3(NO2) OCH( C13)OCH(CC13) l14 10.5 1.2 +++
p-Chloro-N-propylbenzenesulfonamide
ClC6gH4so2HC3H7 102 3.7 1.5 +++
alpha-(l-Piperidyl)alpha-tolunitrile
C5H10NCH(CN)C6H5 143 3.1 1.0 +++
l-(p-Nitrophenyl)piperidine
H10NC6H4NO2 161 2.3 1.0 +++
alpha-(p-Bromoanilino)alpha-
tolunitrile
BrC6H4NHCH(CN) C6H5 155 0.6 1.0 ++









-b3le 3.--Tests at 1 po'unli per 200 ngllous of water
SLarvae Average percent
usied in mortality Amcunt
treat- Tot of
SCopound en /.... ___ me_ I Treated treated feedin_
l-Dichloro-2,2-bis(p-chlorophenyl)-
ethane
(Cic6H)2CCHCH,2 l16 100.0 1.7 0

1-Trichloro-2, 2-bi s(3, 5-dichloro-
2-hydroxyphenyl) ethane
l3 CCH(C6H2C20H)2 S5 100.0 1.3 0

Chloromethyl-4-chlorophenyl
sulfoneji
CIC6H4S02CH2C1 80 100.0 1,0 0

1-Phenyl-2-phenylsulfonylhycdrazine
Cg&HNimSo2C65 156 99.4 0.4 +
2-I sobia tyry -1 -ph e nyltIdrF zine
C6H 5NNHCOCK(CH3)2 146 99.3 0,4 0-+

1-Isovaleryl-2-phenyvlhydrazine
C6H5NO COCH2CH(CH3)2 120 97.9 0.9 +

1-Isocaproyl-2-phenylhydrazine
C6H5emco(cw2) 2H(CH 3)2 146 91.0 0.9 +
N-(3,4-Methylenedioxy thiobenzoyl)-
iorpholine
CH202C6HGC CS (CH2CH2 20) 5 90.2 0.7 0

Bis(5-chloro-2-hydroxyphenyl)methane
(C6H3Cl(OH)) 2CH2 0 77.2 2.0 ++
1-Cinnamoyl-2-phenylhy drazine
C6H5Nfi1iCOCH=CHC6H5 146 65.0 0.9 ++
1-Then yl-2-(p-tolyl sulfonyl ) ydrazin e
C6H 5NHNHSO2C 6H4CH3 95 60.1 0.7 +
alpha, iph, alp,lpha, 2, 4-
Pentachlorotoluene
C6H3C12(C013) 97 56.0 2.0 ++
l-Phenyl-2-valerylhydrazine
C6H5NINHCO(CH2) 3CH3 110 44.3 0.9 +++

2,4-Trichloromethyl-s-trioxane
CC13CHOOH{OCH(CC1 )0 105 33.- 2.0 +++


C C 3 ICH-c





-25-


Table 3.--(Continued)
Larvae re ng. g percent
used. i; r.: o rtality Amount
tratI HNot of
Compound ment Treated treated feedinE
N-Thiobenzoylmorpholine
C6O CSN( I2CH2) 20 74 18.1 0.7 ++
l-Phenyl-2-sulfinylhydrazine
C6H5NN: SO 91. 17.7 0.7 +++
5-(3-Methylbenzylidene)-2-thio-
4-thiazolidone
CH3C6H4CH=CSC( S)NHCO 88 17.0 0.7 ++
5-Isobutyl-1-phenyl semioxamazide
C6H5NHCOCONHCH2CH(CH3) 72 12.5 1.1 ++
Chloromethylphenyl sulfonea
C6H5S02CH2C1 84 10.7 1.0 +

l-Phenyl-2-phenylacetylhydrazine
C6H5NNHHCOCH2C6H5 89 10.2 1.3 +++
sym-Di-o-tolylthiourea
(CH 3CGH4 ) 2CS 66 7.6 0. +++
N-Anilino-alpha-toluamide
C6H5CH2coNHMnc6H5 110 7.3 1.4 ++H
p-Bromo-N,N-dimethylbenzenesulfonamide
BrC6H4SO2N(CH3)2 107 5.7 1.5 +++
6-Nitro-2,4-bi s(trichloromethyl)-
1,3-benzodioxane
6"R3(o2)OCH(CC13)0o( c13) 4 4.7 1.2 +++
alpha, alpha,beta-Trichlorobutyramide
CH CHC1CC12CON2 105 3.8 1.3 +++
N-Anilinocinnamamide
C6H5CRCHCCONHNHC6H5 100 3.4 1.4 +++
l-Acetyl-2-phenylhydrazine
c6gH5NmCOCH3 34 2.9 0.9 +++
l-Butyryl-2-phenylhydrazine
cgBNHCOC3H7 43 2.3 0.9 +++




UNIVERSITY OF FLORIDA
3 1262 09238 7538







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