Preliminary tests of synthetic organic compounds as insecticides

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Material Information

Title:
Preliminary tests of synthetic organic compounds as insecticides
Physical Description:
14 p. : ; 27 cm.
Language:
English
Creator:
Bottger, G. T
Yerington, Albert P., 1914-
United States -- Bureau of Entomology and Plant Quarantine
Publisher:
U.S. Department of Agriculture, Agricultural Research Administration, Bureau of Entomology and Plant Quarantine
Place of Publication:
Washington, D.C
Publication Date:

Subjects

Subjects / Keywords:
Insecticides -- Testing   ( lcsh )
Organic compounds -- Synthesis   ( lcsh )
Genre:
federal government publication   ( marcgt )
non-fiction   ( marcgt )

Notes

Statement of Responsibility:
by G.T. Bottger and A.P. Yerington.
General Note:
Caption title.
General Note:
"E-744."
General Note:
"March 1948."

Record Information

Source Institution:
University of Florida
Rights Management:
All applicable rights reserved by the source institution and holding location.
Resource Identifier:
aleph - 030297821
oclc - 780430028
System ID:
AA00025198:00001

Full Text


March 191&8


United States Department of Agrioulture
Agricultural Researoh Administration
Bureau of Entomology and Plant Quarantine


PRLTIIIjAr TESTS OF SYNTHETIC OHSANIC COMPOUNDS
AS INSECTICIDES. PART V*

By G. T. Bottger and A. P. Yerington
Division of Control Investigations

This is the fifth of a series of papers reporting preliminary tests
with synthetic organio compounds, which were started at the inseoticide-
testing laboratory of this Bureau at Sanford, Fla., and continued at Ana-
heim, Calif. In the previous papers (E-821, E-634, E-72% and E-738) tests
with more than 1,100 compounds are reported. This paper gives the results
obtained from 76 additional compounds received and tested during 1945 and
1948. The Division of Inseotioide Investigations J/ supplied all samples,
which they either prepared or purchased from coomeroial sources.

All compounds were tested against at least three species of insects;
some of the more toxic materials were tested against as many as seven.
The following species were used in the tests

Alder flea beetle (Altioa ambiens (Leo.))
Arzyworn (Cirphis unpuEota (Hawo))
California oakworm hryganidia oalifornica Paok.)
Celery leaf tier (Pr o a ialis Guen.))
Granary weevil (Sitophi ))
Large milkweed bug (oopeltus faoatus (Dall.))
Melonwom (aphani, h--I (Lo))
Southern anmywora I,- --a eridania (Cram.))
Spider mites (Tet"Pus pp*
Variegated outr (Perid ra margaritosa (Haw.))
Vegetable weevil (LiTro ureq ob uns Klug)
Yellow-striped aywozrm (Prodenia omithogalli Guen.)

All insects were reared in the laboratory, except the vegetable
weevil, the alder flea beetle (larvae), and the spider mites (all stages).
The last two were collected in the field. Equipment and certain methods
employed have been described by Swingle, Phillips, and Gahan. 2/


L/ The writers acknowledge the assistance of R. C. Roark, H. L.
Hailer, and other members of the Division of Inseoticide Investigations,
who supplied the compounds and furnished the foraulas given in this paper.

!/ Swingle, M. C., Phillips, A. Me, and (ahan, J. B. Lajboxubo
testing of natural and synthetic organic substances as inaeci,Alam.
Jour. Boon. But. S434s 95-99. 1941.


E-744










The exp.,ciL.... p2iL7 -. *- ..r:* aere the same as those followed in
Part III, with ch.-. :- on of the fumigation test. In this test 0.25
gram of samp"i. ;- -_ -.- 10 or more adult granary weevils con-
fined in the lc.-;r ?.' of a ,.Arl dish with a few grains of barley for
food*

When raoei -A for' the samples had been diluted to 25 per-
cent in pyr .. .y. were in good physical condition for
dusting. Preli.:',Wa... .-:.. agLinst leaf-feeding insects were made
on all samples I' f-' x'i to arae leaf sections that had been dusted with
the 25-percu.&t mate -_ust was applied in a settling chamber, de-
scribed by Sw'irngie, :... and Gahan, Y/ to both surfaces of the leaves,
and the amount 4oyLpo. .i *d :'.j tarmined by weighing an aluminum plate dust-
ed at the same tli-,. Th --,I.ed leaf sections were then placed in 9-cam.
petri dishes together with eiCh. fourthi-instar larvae. A total of 24 lar-
vae was used for .: L -u.. t.ninations were made after 3 days, and the
mortality and es+i,.L.".1, .",, u recorded.

atert :.. ;:., '...-It s of 75 percent or higher to one or more
species were te,- .s. ', .,. to indicate their relative effectiveness when
applied as spray ...t-ta to determine their toxicity to green foliage,
their volatility; -i r': I'.,r -f ctiveness as fumga t s; and to distinguish
between oont&ot" .-Cid ^iJ. -pnf--i'sona

For oc.'iw.,,-.' ., "', ,s 'ere made with benzene hexaohlorides the
gamma isomee c'. b._ -... ,,':_. orded DDZ and o-diohlorobenzene-inseotioides
of known effecti7::t.n. .21t. certain of thes' insects. Results of these
tests are shown in e.-. 1e

Data on 1' cL ,'-i,., is that caused greater than 75 percent
mortality to one o.-: sM.ror .' ' of insects in dust tests are shown in
table 2, Four f ti. ....Lpv::i.--ohloroethyl 4-ohlorophenyl sulfone,
ohloromethyl phi., u. ..-.j, methyl-4-ohlorophenyl sulfone, and l,1,l-
triohloro-2,2-'.f(3 .-i"- .,::- 2-hydroxyphenyl)ethane--oaused 90 to 100
percent mortality 1of :.Li, .- or more species. In further tests it was found
that the fii-ast to. i-,i as bo'-it omach and contact poisons, and the last
two only as et., :.h ,-:. ... Th-ilo of these materials are sulfones and
therefore ',.j/ .*' i.- .. cally. Slight to moderate feeding occurred
in all teats, Chl`4-,. L- i 4,-,hlorophenyl sulfone. and ohloromethyl phenyl
sulfone vold . ,. ..-',,t of 62 and 48 percent, respectively. Both
compounds were i-.l..7.%.ive dhe'-i tested as fumigant against the granary
weevil,

Of all tho ,,.&,ralB li.'tod in table 2, only one-2-(diethylamino)-
ethyl p'bntaehh, ;,;7-;. ei.or,, caused more than slight injury to any green
foliage tea+;d. Wc. sp Dzrs c:to young plants this compound caused severe
injury to 3orn r.d :3 r', f-,- i.orlerate injury to lima bean, pumpkin, and


The loo.,s-.' ..;. -..t ?:,i..- loa than 75 percent mortality of the species
agldr.t whiol, t'.j'y "' .".. .T.:, p.re listed in table 3.







- s -


SUMUA

The results of tests of 76 oompounds are included in this paper,
which is the fifth of a series reporting preliminary laboratory tests to
determine the inseotioidal value of synthetic organic compounds (3-621,
3-634, E-729# and 3-738) Eighteen compounds gave greater than 75 per-
cent mortality against one or more species of insects, and four-chloro-
methyl 4-ohlorophenyl sulfone, ohoromethyl phenyl sulfone, methyli4-
ohiorophenyl sulfone, and 1,ll-trlchloro-2,2-bis(3,6-diohloro-2-hydrozy-
phenyl) ethane -- were very toxio against three or more species. Only
one of the 18 toxio materials caused more than slight foliage injury.

Volatile materials were ineffective when testedd as fumigants
against the granary weevil.







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TaIe 35. -- Compounds causing less than 75 pereeht mortality of all species
against which they were tested


Compound


Insect j/


Acetic avoid, alpha-(trichloromethyl)benzyl ester
CH3COOCH(CCl3)C6H5


N-Butyl-p-nitrobenzamnide
O2C 6H4CO'RC4E9


N-seo-Butyl-r-nitrobenzamide
NO2CH4CONHCH(CH3) CO5


o-Chlorobenzamide
C IC6H4CONH2


-Chlorobenzamide
ClC6H4CONH2


3-Chloro-alpha-(pentachlorophenoxy)acetanilide
CC 15OCH2CONHC6H4Cl


j-Chloro-N, N-dimethylbenzemide
ClC H4CON(CH3 )2


o-Chloro-N-ethylbenzamide
C lC6ICH4CONHC 5


o-Chlo ro-N-methylbenzamide
ClC 6U4CONECH


Alder flea beetle 2/
Celery leaf tier
Melonworm
Southern armyworm
Variegated outworn

Alder flea beetle
Anayworm
Celery leaf tier
Variegated cutworm

Alder flea beetle
Aznywon
Celery leaf tier
Variegated cutworm

Amnyworm
Celery leaf tier
Variegated cutworm

Armyworm
Celery leaf tier
Variegated cutworm

Armyworm
Celery leaf tier
Peach aphid
Variegated cutworm

Armywomn
Celery leaf tier
Variegated cutworm

Armyworm
Celery leaf tier
Variegated cutworm

Arnyworm
Celery leaf tier
Variegated cutworm


I/ Peach aphid specimens were nymphs and adults; all others were fourth
instars except where indicated otherwise.


2/ Mature larvae.






- 10-


Table 3, -- (Continued)


Insect I/


Chloromethyl j-tolyl sulfono
CH3C6H4SO02CH2C1


4,4*-, A-:lohexylidene-bis(2,6-dichlorophenol)
C 6)o0(C6H0oYCl2)2


N-Cyol oha xl-bis- (p-ohlo rophenyl) acetamide
(c H 4C 1) CHCOmVTc6H 1)
6 4 2 6 11

2. (Dibenzylamine)ethyl pentaohlorophenyl ether
C6 Cl OH2CH2N(CH 2CH 5) 2



N,N'-Dibenzyl-'- (2,5-dichlo rphenyl)-
ethylenediamine
C 6H3Cl 2NHCH 2CH 2N(CH2C H5) 2


3,4-Dichloro- i-ethylbenzamidde
C 6H 3Cl2 CONHC H5


l-( 2,5-Dichl o rophenyl)urea
C 12C 63NHCONH 2



N,N-Diethyl-p-nitrobenzamide
NO2CH4CO(C 2H5)


N, N-Dimethyl-p-nitrobenzamide
C 4(Nod)CON(CHZ)2



N- ( 2- ( 2,4-Dinit rophenoxy) ethyl) dibenzylamine
(Ce5c^ d NCH 2CH2OC63 (No 2)2


Armyworm
Celery leaf tier
Variegated outworm

Armyworm
Celery leaf tier
Variegated cutworm

Arnywom
Celery leaf tier
Variegated cutworm

Alder flea beetle
Armnyworm
Celery leaf tier
Variegated cutworm

Anmywom
Celery leaf tier
Peach aphid
Variegated cutworm

Arnyworm
Celery leaf tier
Variegated cutworm

A rmywonm
Celeryr leaf tier
Peant irJ..d
VariesAted o-itwcrm

Ariyorm
Alder flea beetle 2/
Celery leaf tier
Variegated outworm

Alder flea beetle 2/
Armyworm
Celery leaf tier
Variegated cutworm

Armyworm
Celery leaf tier
Peach aphid
Varieg'ed cu' -


Compound






W" 4WL


Table 3. -- (Continued)


Compound


NN-Dipropyl-p-nitrobenzami do
NO 2COCON( CsH^J



N-Ethyl-2-nitrobenzamide
NO2C 8H4CONHC 211



N-I sobutyl-g-nitrobenzamide
NO2 C HCOHCH CH(OYH)



N-I sop ropyl-2-nit robenzamide
O 2c 6H4cOHCH (CH) )



N-Methyl-2-nitrobenzamide
N02C H4CONHCH3



2, 2-Methylenebis(4-chlorophenol)diaoetate
CH2(CH3COOCRHCl)2



1,1-Methylene-di-2-naphthol
CH2 (C10HO6H)2



2-Nitrobenzoio acid, benzyl ester
No C6H4CO0CH2C-5


2-Nitrobenzoio acid, p-bromophenyl ester
NT2C 6H4COOOC04Br


Alder flea beetle 2/
Armywo m
Celery leaf tier
Variegated outworn

Alder flea beetle -/
Armyworm
Celery leaf tier
Variegated cutworm

Alder flea beetle
Armyworm
Celery leaf tier
Variegated outworn

Alder flea beetle 2/
A naywo m
Celery leaf tier
Variegated outworn

Alder flea beetle
Anyworm
Celery leaf tier
Variegated outworn

Alder flea beetle
Armiyworm
Celery leaf tier
Variegated cutworm

Alder flea beetle
Armywozm
Celery leaf tier
Variegated outworn

Alder flea beetle
Armnuywomn
Celery leaf tier
Variegated cutworm

Armyworm
Celery leaf tier
Variegated outworn


Insect 1/










Table 3. -- (Continued)


Insect I/


p-Nitrobenzoic acid, p-chloroethyl ester
N02C6H4COOC6H4Cl


p-Nitrobenzoio acid, o-chlorophenyl ester
o02c64COOC 6H4Cl


Z-Nitrobenzoio acid, oyolohexyl ester
N02C H4C0oC e6


2-Nitrobenzoic acid, 2,4-dinitrophezyl ester
NO2C6H4CooCH3(o0 2


p-Nitrobenzoic acid, ethyl ester
NO2C 6H4CoC 5



-Nitrobeazoio acid, methyl ester
NO2C6H400CCH3



r-Nitrobenzoio acid, 2-naphthyl ester
NO2C6H40COOCoH7


j-Nitrobenzoic acid, o-nitrophenyl ester
N02C 6H4C00C6H4N02


p-Nitrobenzoio- acid, phenyl ester
N 02c6H4OOCGH5


j-Nitrobenzoio acid, propyl ester
N02C 6H4COOC3H7



Z-Nitrobenzoic acid,2-(2-pyridyl) ethyl ester
NO2C 6H4C00 C2CH2C5H4N


Armnyworm
Celery leaf tier
Variegated cutworm

Armnyworn
Celery leaf tier
Variegated cutworm

A rmyworm
Celery leaf tier
Variegated cutworm

Armyworm
Celery leaf tier
Variegated cutwornm

Alder flea beetle 2/
A rnyworm
Celery leaf tier
Variegated cutworm

Alder flea beetle 2/
Anayworn
Celery leaf tier
Variegated cutworm

Armywom
Celery leaf tier
Variegated cutworm

Armywonm
Celery leaf tier
Variegated cutworm

Anrywormn
Celery leaf tier
Variegated cutworm

Alder flea beetle 2
Armyworm
Celery leaf tier
Variegated cutworm

A nrmyworn
Celery lIcf tia
Variegated cutworm


Compound






- 13 -


Table 3. (Continued)


Compound


m-Nitrobenzoio aoid, 2-(2-pyridyl)ethyl
ester
NO2C 6H4COOOCH2CH2C5H4N

-rNitrobenzoio acid, tetrahydrofurfuryl
ester
NOgC gH4COOCHCH2CH"CH CIE
S4coo2 Hc2 2 22.


alpha,alpha, alpha, 2,5-Pentaohloro-
acetanilide
C13CONHC 6H2C2


N-Propyl-y-nit robenzamide
NO2C H4COKC3o17



4,4-Sul fonyldiphenol
(c6H4oH) 2so2



2, 2' -Sulfonylbis(4-ohlorophenol)
(%C6a130W- 1)t 23 02

2,4-Sul fonyldiphenol
(C6O4H) 2S02



3,3',5,5'-Tetraohloro-2,2' stilbenediol
C 6H20HC 12CH CHC eOHC 12


2,2 '-Thiobis(4-chlorophenol)
(c so0HC 2) 2S



alpha-(Triohloromethyl)benzyl alcohol
C 6H CHOHCC1
65 3


Armnyworm
Celery leaf tier
Variegated outworn

Armyworm
Celery leaf tier
Variegated outworn


Alder flea beetle 2/
Celery leaf tier
Melonworm
Southern anryworm

Alder flea beetle 2/
Armyworm
Celery leaf tier
Variegated cutworm

Alder flea beetle 2/
Armyworm
Celery leaf tier
Variegated outworm

Armyworm
Celery leaf tier
Variegated outworm

Alder flea beetle 2
Arnmyworm
Celery leaf tier
Variegated outworn

Amywom
Celery leaf tier
Variegated cutworm

Alder flea beetle
Armyworm
Celery leaf tier
Variegated cutworm

Alder flea beetle 2/
Celery leaf tier
Melonwornm
Southern a nnywon


Insect /





UNIVERSITY OF FLORIDA

3 1262 09239 2199


Tble 3* -- (Continued)


Insect 2/


l-T i-iohloromnethyl-4,4 '-methylenebis
(2, 6-diohlorophenol)
GlCH (C 6O2OHCl2) 2

1,l l -Triohloro-2,2-bis(5-ohloro-2-methoxyphenyl)-
C.-thane
Cl 3CCH(CAOCHCl)2


ll, I -Triohloro-2,2-bis(3 ,5-diohloro-2 iethoxyphenyl)-
St,-ha28
L cCH (C 6iCl 2OCH3) 2


l, llj1--r i'.hloro-2,2-bis(2,5-dimethoxyphenyl) ethane
ci 3ca(c 6H (oC ) 2)2


1,14 1-- r"d. loro-2,2-bis(3,4-dimethoxyphenyl)ethane
Cl. .CCHfC (ocH) 2)



2,2, 2-T 1 loro-1-(2,4-dihydroxyphenyl)ethanol
C63 (CH) 2CH(C013)0H



S- 2-Triohlo ro-l-hydroxyethyl) benzamide
C _.H.CiMCBOHfC~l.
rONHbQ 1


li,1,l-Trio1 ore-2-phenyl 2-biphenylethane
C63% `m "C614Ch1


S : ..(llor 1 :-.-(2,3,5-tridhloro-6-
mb .:.pneivl)-o-o resol
C6HCl3(OH)GCHC6gHl. 3.n


Anyworm
Celery leaf tier
Variegated outworn

Alder flea beetle 2/
Aryworm
Celery leaf tier
Variegated outworn

Alder flea beetle 2/
Armiywo nm
Celery leaf tier
Variegated outworn

Arnqworm
Celery leaf tier
Variegated outworn

Alder flea beetle 2/
Arnyworm
Celery leaf tier
Variegated cutworm

Alder f.e&a beetle 2
Anrnyworm
Celery leaf tier
Vartegated outworm

Alder flea beetle 2
A rnnyworm
Celery leaf tier
Variegated outworn

Alder flea beetle /
Amnnywom
Celery leaf tier
Variegated outworn

Alder flea beetle
Armyworm
Celery leaf tier
Variegated outworn


- 14-


Compound -