Preliminary tests of chlorinated benzamides as insecticides

MISSING IMAGE

Material Information

Title:
Preliminary tests of chlorinated benzamides as insecticides
Physical Description:
21 p. : ; 27 cm.
Language:
English
Creator:
Bottger, G. T
Yerington, Albert P., 1914-
Gertler, S. I
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 )
Insect pests -- Control   ( lcsh )
Genre:
federal government publication   ( marcgt )
bibliography   ( marcgt )
non-fiction   ( marcgt )

Notes

Bibliography:
Includes bibliographical references (p. 2).
Statement of Responsibility:
by G.T. Bottger and A.P. Yerington and S.I. Gertler.
General Note:
Caption title.
General Note:
"E-789."
General Note:
"November 1949."

Record Information

Source Institution:
University of Florida
Rights Management:
All applicable rights reserved by the source institution and holding location.
Resource Identifier:
aleph - 030337456
oclc - 780439391
System ID:
AA00025221:00001

Full Text

November 1949 E-719")


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 species 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 (Lec.))
Armyworm (Cirphis Zipunoita (Raw.))
Cabbage ap TBrevicorne rassicae (L.))
California oakwo Phryganidia calfornioa Pack.)
Celery leaf tier (P-lyotaenia rubIgalis (Guen.))
Citrus red mite (Paratetanhus citri (McG.))
Green dock beetle Gastro cya Melsh.)
Large milkweed bug (Onopneltus fasciatus (Dall.))
Pea aphid (Macrosihum pisi (Kltb.)
Two-spotted spider mite (Tetranychus bimaculatus Harvey)
Variegated cutworm (Peridroma margaritosa (Haw.))
Vegetable weevil (Listroderes oliquis 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 physical
condition for dusting,





- 2-


Materials casL "u alities of recentt or hi "!''rr as doiste
were allied as "rays to he leaveL r "" FL .nds ..
~~ q.. ttrn knd i..
to determine whether they would i.-iure .:'.r:&. foli<- e. -.e r.- E
contained .2 -: recentn t material ap lied at tre rate of c Hs :.z-r i."
;llon:i of water to ,;r'e:r. folia,-e of plants rri:.- under natural
ccr-ditionl.

'. results "' the tests with insecticides af kno mlue
-. ,inst certain incects, made for ,::. E ra ive -- arc !reren-
to L ... d r-a i~ ts s 4e -,ae-1 : -
ted in table i.
Dita on 27 'c.'n: oi. ds tnAt caused greater than 74 percent ao.-tm-l-
i'v to one or more _" ,.cieB of insects in dust tests ar ano in
table 2. C: these materials 2 were effective _: -inst the two-SBOt-
ted s3ider mite.

Or. the basis of the number of s;-cies affected, the four st
toxic -..-o-nds a:. f-ar to be ,--..,o-,- is--.-bernsdce, 3,4-
Sich.l oro-lN-dii sc:- r-^ c r benz- a ne, 3,4-dichlor"-_.',N- .:-, "'iybesa-.
eide, and 2-ahe:.ylhy.'arazid-o-chlo-obenzoio acid.

The first tlroc cc.o'ounds n&-ed re effective both s contAct
arnd as stomach poisons, but 2-phenylhy.ra:ide-o-chlorobenzoio acid
was not effective as a contact S :son a-,i.st the insects te te No
arpreciable inf .c-.. to foliage resulted from E: r-ay aplications of y
of the four D-:--.:.'E- Co.rounds reported in table 2 that did snow
moderate toxicity to green foliare of one or more kinds of plants we-r
.. .. --- .. r &i. c-an: 2,4-
.,-[..-':'l-3,4-dlchloro :enza~mide, 2, :: chloro .. t}.yIcensacie, ad24
di hloro- :,-d i p ro)-lben znaide,

Table 3 pFsents results -'' tests 1:-tinft various Lnrect- wi'h
29 '-. uouids tlAt -lve kills between 2- and 74 percent. Emever,
the only 'rv ".rnds that .u:d nortalities "'f -' percent or hi -).,r
're 3,4-dichlor -;.-3ezyloenrzai !e, o--C.lorc-'r.-7ec-7.,-.PIber.n-de,
2-, 'enyl? 'r<,: ide-3,4-1 chlorobenzoic acid, and *- -ichlerober:.-'. l-
piperidine R Rinst the two-o-,pct.v r'. ider mite, h~ an r7-ide--
ch orol'ezxoic acid *iainst the celer leaf tier, 2d 2',,4,5'-tetrt-
clorubenztnilide t "iinst the a- aphid.

"u r s". ud tht caused less than .. rcnt ncrtal!' f e
srdcies '-ninst which they were toted ae listJd in table 4,

Literture Cited

(l) win xle, L..'., illits, A.I.., and *Ja an, J...
1 1'I. L'lborB s'r" test':.* of nature. ] an :'.tetic organic
jbst ce' ,5s insect' :. J;ur. Ec n. :.t.




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- 15 -


Table 4. - Chlorinated benzamides that were found to be practically nontoxic,
killing less than 25 percent of insects fed dusted foliage


Compound Insect Stage


Percent


Anthranilio acid, N-
(2,4-diohloro-
benzoyl)-



Benz=uide, 1-amyl-
o-ohloro-



Benzamide, N-amyl-
j-ohloro-


Benzamide, N-amyl-
2,4-dichloro-


Benzamide, N-benzyl-
-chloro-


Benzamide, N-benzyl-
2,4-dichloro-


Benzamide, N-sec-butyl-
o-chloro-


Benzamide, N-butyl-
2-chloro-


Benzamide, N-sec-butyl-
-chloro-


Benzamide, N-butyl-
2,4-dichloro-


A rmyworm
Celery leaf tier
Large milkweed bug
Pea aphid
Two-spotted spider mite

Armyworm
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
doe
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 -


"-. e 4. f1c-:.-: od)


om;-u md


Pe recent


Pea zwrft de, N-sec-butyl- 5
2 ,4-di chloro-



renzLamide, -c&1loro-N-2- 25
bicyclobhjexyl-



-.enzaai de, j-ohloro-N- 25
cy : lo heIyf-



.enz.amide, k-?. loo-)- 25
ae,)tyl-



Benza.-itde, p-'iloro-n- 25
propyl-



Benz-alde, NIN-dlibenzyl- 25
o-ohloro-



m-'zu.-nide, N,N- itben-yl- 25
-'-.rhlor.o-



',,ntSn : aoe, N,N-,i-benzvl- 25
3 4-'iic, c~l n-P -



.* n. ido, ';,N--It .ityl- b
T, 4 i- 1 o r --



.' : Lr. r1, ,4- i'hloro-N- 5
.f- .'.-loh4%xy.-



nnirai.dlo, ,i-1i "il. ri -N- 5
,'y -lih.exyl-




v .-. ., i -


Celery ~a.:'
Poa aphid
'^-o- s oo^te


Celery lea-f
Pea a :L d
?w5- rpott:edz


,C i-1 e.-ry 1" if

Pea ah. d
Tw O'. ott e -

, 8@le.-y 13"

Pea aprnid
Tw >-spo t'- ed

Celery ie l_
Pea a.n-i.ic,
T' o-8ep *,tei


Colervy 1""
Pea a- ':. l
Tw -.- "..i

I eler" lea'
Pea a.-, hi
F'w -potted

.'?< : r-." .et<
Pea a. -'.x
PO a- -. :I;


"-i .-Vy I PL


Tw .,-'- 8"- ct.' ,


t-er
s z'er mite










-3 C, r -A


t I'r


a -tdolr ute


a.:vr rite







r- : 9


S -.- ..


"," *K "'--,, ,,,*" ', r
Ci L ,' *
S*, .. .


.'* 11jury ^'t :'



9'; I' 4' .

*t^ *1 '


)ajrt2-. tnt.a-jr
-a r-.4 : -,a r
2 iay -o i -:/ 'n -
Jrru:r.s a.-.,: a.. a .a


L-3 f-ni,: rt.a-Lr
t.-a~y .>i: t::.Atu -
"r- -. a *-* a n -- rI- 'L



Sz'-- T t..-. tar
2--r- 7-.-. za- -t



* :-t : n var'. r
. s ",":-__ c L. xr .' :a
.- .'.- ..-. .--, si a,-. 1t

*-- r- iZ st.
2- 'tv.-? -: wrr n' -u
r2 ; m t:-2 a a',ita

*' ,_" .. r,-. 8..: -
S- ;ay- '. ."- --_ -B
, -,_~ --s 'r -*;':, e



.- j r. -.: *-

N;.-. -. 4.- * *'

.h". ": ." ? ".
- -,- -. .. r. ,J
-. -..'.$ t'." TJs 1 $


.. :. ..= >

-" ".- :'L. % -


s~e %-z:.




r %. a


3St a- e


U -


I '. ,*








Table. 4 - (Continued)


Compound


Percent


Benzamide, 2,4-diohloro-
N-isobutyl-


Benzamide, 3,4-dichloro-N-
isobutyl-


Benzanilide, 4'-benzoyl-4-
ohioro-


Benzanilide, 2'-braumo-
2,4-dichloro-


Benzanilide, 4'-broBmo-
2-chloro-


Benzanilide, 41-bromo-
4-chloro-


Benzanilide, 4' -bromio-
2,4-dichloro-


Benzanilide, 4'-bromo-
3,4-diohloro-


Benzanilide, 2-chloro-



Benzanilide, 2-chloro-2'-
nitro-


Benzanilide, 4-chloro-



Benzanilide, 4-chloro-2'-
nitro-


5 Celery leaf tier
Pea aphid
Two-spott-ed sp- ir mite


Celery 9+7 .
Two e pofC i_6 r ad. te


25 Celery --., tier4
Pea ,:: d
Two-snotttd cpier ialte

5 Celery leaf tier
Pea aphid
Two-spotted spider wite

25 Celry laf tier
Pea aSahI
Two-spotted -- -.

25 Celer" 'I tier
Pea aphid
Two-spotted spi.-r mii.

5 Celery ler" tier
Pe
T' '_,- .t spider mi+e

5 Celer .-ier
Pea ahd
Two- ~. tt- ider mite

25 Celery lea t
Pea aph.;
TIvo- ,.:tted .. dr mite


Celer- leaf tier
Pea .ic.
Two-spotted spider mite

Celery leaf tier
Pea aphid
Tr,-spotted _:ider mite


25 Celer3 i; tier
Pea aphid
Two-spotted spider mite


Fourth inztar
2-ddy-old nymphs
i i,_-^&n'2 ,adults

Lo*
-ioirh Lu tar
;lhb and adults

F outh ia" tar
.-:.~y-old nymphs
Nay1-1 and adults

Third instar
2-day-old nympha
Saphe and adults

'-'*.iS tar

.* ,s and adults

-. -th instar
2- lay-old nymphs
.1 stages

'. i.-d instar
adult


S--th instar
2 -old n.ymfi-hs
. and adults



*. ii-1641a r
_. "ix. Sa



Fourth irbte-r

,m;'.s and adults

Fourth inBtar
2-day-old nymphs
.;,:.. -. and adults

. ouAh instar
2-day-old nymphs
'A',, '-, *n. ,' adults


Inseot


- 17 -







S18B -


P ~. - ( ~~1~~11.AeGJ


;' recent


'-nit ro-


:enzanillide,
4'-nitro-



benzani ] ide,
dichloro-


,* :-zsaji] ide,
dichloro-




" : :~i1lide,
dicaloro-



Senzainilide,
cli chi ro -


4-ch2oro-




4- chloro-


e1~ry P~ar
~j. a:r.:Q
**jg-r* ~q* t1Lr~

Th>r. I~.*
'~
* ..z-'~ ofe~i


tier

S ider -ite




spider *it~e


-*!r -"* le,-' tier
Pea aphid
-'-zvotted pider At


2,Z-


2' 4-


CeIey le,.f tier
Pea a'.h-
-'Wc 0. otted spid


CeTry Ie.: tier
r: aphid
twc--.; '. ted : icer mite


2,4-


Celery leaf" tier
Green dock boetl
La r -f n I ke-




i,1., a .h

-. c-ot"od F i

C. le"" l f tier
?'' *i a~hid


1 '*r \ -rrot I' .


r'-e o. '- i r : *
'" -' ".





.. .. ".. ,
S ',- *., ,
S "% ".
Nf "' * ' '
Hi A
"U _


.en zuilide, 2,4-
dichlorc-2'-niitro-




4-ditro o



4'-i-ntro



*r0 i i 1 i'it, 2,4-;i 1 clorc-
P'.- .,'nyl &to-


e


Fourth inB'tar
2-dfty-old :'.v-_= :'.B




2-day-old -v'.2
; "._....F d adults
*F ad&_L.t

>-:rd it t ar






N'.":h-;:B md a iultu


F-orth ir-star
2-d :. -old "-,-- hs

&a.. dultS

":.-rd i-s ta r
do.
Fou rth :.L-tar
.... i- *dinst~r ay phs*
: .; cl(d z'/.' 2 .,
., .*-. A;s id adult ;*

....rd :.:.; -r
->;.,.--old :..*'" hs
rc.j .d l


:hird : 'tar
2-d .-. Id ....- ':.
*r r 'te '. h- a.nd &dul

r..- :. -.- -


: ;.. ,.r



'.. :.. r

-'A
e .:': ,' t "n


I r~n ~ ct


Stae -






- 19 -


Table 4. - (Continued)


C compound Insect Stage


Percent


Benzanilide, 3',4-
diohloro-


Benzanilide, 4,4'-
dichloro-


Benzanilide, 3,4-
diohloro-4' -nit re-


Benzanilide, 2,4-dichloro-
2 '-phenyl-





Benzanilide, 2,2',4,50-
tetrachloro-


Benzanilide, 2,2't,4-
triohloro-


Benzanilide, 2,2',5'-
trichloro-


Benzanilide, 2',1,4-
triohloro-


Benzanilide, 2,:3,4-
trlaohloro-


Benzanilide, 2,4,4'-
trichloro-


Benzanilide, 2',4,5'-
trichloro-


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

Annrmyworm
Celery leaf tier
Green dock beetle
Large milkweed bug
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

Fourth instar
2-day-old nymphs
Nymphs and adults

Fourth instar
2-day-old nymphs
Nymphs and adults

Third instar
do.
Fourth instar
Third-ins tar nymphs
2-day-old nymphs
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-ins tar
2-day-old nymphs
Nymphs and adults

Third instar
2-day-old nymphs
Nymphs and adults

Fourth instar
2-day-old nymphs
Nymphs and adults






- 20 -


' -.c 4. - ( C' innaed)


Percent


tri chloro-


o-.ernzxji side, 2-:hlorc-



* -BenzAidide, 2-ahloro-




-BenaLLrAide, 4-chloro-


o-. -nzaniaide,
dichloro-


taniaide,
dihloro-


Celery le.f tier
P?. a 7dd
Twc-5,:tteJ sFidder zte

Celery le'" tier
Pea a: -id
Tw'-spctted e:ider Mite

Celery le' tier
Pea &a-hLd
Two-cplotted s: ider e

Celery leaf tier
Pea a. hid
Two-Lcotted s5ider kite
V&rie-at-4 ouao twm

Celery lea tier
Pea aphid
Tw-et'ct ted ider aite

Celery l-~ tier
Pea a:-!d
Twc-sroetod s. ider mite


2,4-


3,4-


"r o-, -phenylhylra-


.- !' Aolcluide, 2-chloro-

'-rKr~oto uie, -rchl o ro-





m-- n~ot luide, 4-chloro-




.- ; c i,.) d,, 4- :vilor




-"e.?.-*olu~l ; ** .0cro~


Celery le.,: tier
Pea a"h1 d
wo-', ted U rider ii.e

Cetler' leaf tier
Pea .: hid
Two---" ,-t-ed spkider mt

Celer," 1eI'" tier
' a .d
..o- otted ier me

7' l T I '7 ier

"1 -: ,.tj ,- id r mite



-w ., ,o td d rm t


2-dan 4-Oc tz .,- t :
''S::. ird a lt

rF-t.--h nectar
2-dAy-old nm:: hs
r."-.^f s d adults

Fourth inse. &r

yNL:--. &nd a&ujlt*

Fourth in.ut r
- :,y-cd idt phr
-t~=7'n. a&=c adults
%-.^Lrd inzarA

N o.
Aduatu

r.n tadulto
~rth l? r
2- i'y-old ::imF-i







'^ s a.-.dU a--l st



fourh i..tr
,2,- I. -.: a t



N.". hs m:: adults

Fourth :" t. r
2- -. .5-a'. .h
'.',. h 'n 'r. a.-ults








N}.<'r anA a h~ta

'_. an r~.L "tS
NVm.' -. h :-d idul


II


Celery leaf tier

.-,e- tted spid,






- 21 -


Table 4. - (Continued)


C compound Insect Stage


Percent


m-Benzotoluide,
2,4-dichloro-


j-Benzotoluide, 2,4-
dichloro-


Morpholine, 4-
(p-chlorobenzoyl)-


Morpholine, 2,4-
dichlorobenzoyl-


Morpholine, 5,4-
dichlorobenzoyl-


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


Third instar
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-day-old nymphs
Nymphs and adults




It Hill i III
3 1262 09227 900





I]










." 1