Styrylsulfonamides as chemosterilants against house flies and boll weevils

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STYRYLSULFONAMIDES AS CHEMOSTERILANTS
AGAINST HOUSE FLIES AND BOLL WEEVILS

ARS-NE-84
JUNE 1977

AGRICULTURAL RESEARCH SERVICE e U.S. DEPARTMENT OF AGRICULTURE

CONTENTS

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TABLES

1. Chemosterilant activity and toxicity of 10 effective
Styrybyanalogs shed, tocadultybolleweevalisi cs <:sicic fis, cleie) ewalsrs «ars s6
2. Chemosterilant activity of 5 effective styryl analogs
fed to adult house flies

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Agricultural Research Service
UNITED STATES DEPARTMENT OF AGRICULTURE

in cooperation with
Mississippi State University Agricultural Experiment Station

STYRYLSULFONAMIDES AS CHEMOSTERILANTS
AGAINST HOUSE FLIES AND BOLL WEEVILS

il
Albert B. DeMilo, James E. opiceasse Richard L. Bue and Jack W. maonees
ABSTRACT

Eleven styrylsulfonamides were effective sterilants against boll weevils
and house flies when the compounds were added to the diet of adult insects.
In boll weevils, 10 compounds markedly inhibited oviposition in females but
high toxicity prevailed at most concentrations. Five sulfonamides tested in
house flies by feeding were effective sterilants. The most effective compounds
for flies were (E)-N-(2,4-dinitro-1l-naphthaleny1)-2-phenylethenesulfonamide
(AI13-62771) and (E)-N-(2, 4-dinitro-l-naphthalenyl) -2-(2-thienyl) ethenesulfon=
amide (AI3-62959). Structure-activity relationships were inconclusive for this
group of compounds.

INTRODUCTION

in V973nFy.en ee al. (5)? described the sterilizing activity of 2,5-di=
chloro-N-(2, 4-dinitro-l-naphthalenyl)benzenesulfonamide, I, R=2,5-(C1)
(AI3-52766) against house flies (see fig. 1). Subsequently, DeMilo etal.
(2,3) reported in detail on the structure-activity relationships of sulfon=
amides related to structures I and II, and in one study (2) the sterilizing
activity of N-(2,4-dinitro-l-naphthaleny1)-2-phenylethenesulfonamide, III,
R=phenyl (AI3-62771), against house flies was reported. Here we report for the
first time the sterilizing effects of 11 trans-styrylsulfonamides (structures
III and IV) and related compounds in adult house flies, Musca domestica L., and
adult boll weevils, Anthonomus grandis Boheman, when the compounds were added
to their diets.

1/ Research chemist, Insect Chemosterilants Laboratory, Agricultural
Environmental Quality Institute, Agricultural Research Service, U.S. Department
of Agriculture, Beltsville, Maryland 20705.

2/ Research chemist, Pesticide Degradation Laboratory, Agricultural
Environmental Quality Institute, Agricultural Research Service, U.S. Department
of Agriculture, Beltsville, Maryland 20/705.

3/ Agricultural research technician, Insects Affecting Man Research
Laboratory, Agricultural Research Service, U.S. Department of Agriculture,
Gainesville, Florida 32604.

4/ Research entomologist, Boll Weevil Research Laboratory, Agricultural
Research Service, U.S. Department of Agriculture, Mississippi State,
Mississippi 39762.

5/ Italic numbers in parentheses refer to items in "Literature Cited" at
the end of this publication.

; NO,
R R
W®)-50,NH O)-No, YO) SO,NH NO,

I I

NO,
ne. SO,NH ©) NO D ia 2Oy NO,
YA < H

ie IV

Figure 1.--Structures of sulfonamides.
MATERIALS AND METHODS

Chemicals.--Test compounds were synthesized by previous methods (7). Com-
pound purity was estimated from spectral and physical data to be approximately
95 percent.

Boll weevil screening tests.--The tests were conducted with an ebony strain
of the boll weevil (1). Candidate compounds were dissolved in acetone and for-
mulated into a previously described diet (6). The treated diet was cooled and
subdivided into pellets, and the pellets were coated with wax and stored at
approximately 5°C until used.

Sterility and mortality values were determined as follows: 25 (1-day-old)
adult weevils of one sex or 50 (l-day-old) adult weevils of both sexes were fed
chemosterilant-treated pellets for 3 days, after which time the treated diet
was removed and replaced with untreated pellets. Dead weevils were counted and
removed 7 and 14 days after treatment was initiated, and percent mortality was
assessed. When separate sexes were treated, the treated weevils were crossed
with 25 virgin untreated weevils. If female fecundity was noticeably unaffected,
100 eggs were collected (50 at day 7 and 50 at day 14). The egg samples were
divided in half; one half was held for hatch and the other was implanted in
larval plates (8) to determine adult F emergence.

House fly screening tests.--All of the materials were tested as additives

2

to the diet of adult house flies of both sexes by previously reported pro-
cedures (4). Briefly, each compound was added on a W/W basis to a diet of
granulated sucrose or regular fly food (a mixture of sugar, powdered nonfat dry
milk, and powdered egg yolk, 6:6:1). At 6 days posttreatment a random sample

of 100 eggs was collected and held to determine the number of pupae that formed.
However, when the compound was offered in sugar, untreated fly food was provided
after the 3d day for 4 days to provide protein for egg nourishment. Sterility
in house flies was assessed on the basis of the number of eggs that survived up
to the pupal stage of development.

RESULTS AND DISCUSSION

Ten variously substituted styrylsulfonaphthylides (III) and styrylsulfon-
anilides (IV) caused complete or partial inhibition of egg production when the
compounds were fed for 3 days to adult weevils of both sexes or adult female
weevils (table 1). Since most compounds were highly toxic to the weevils it is
reasonable to assume that the reduction in fecundity was primarily caused by
the toxic effects imparted by the compounds. Eggs that were collected appeared
to develop normally, as hatch and emergence indices did not vary significantly
from those of the controls. The most effective chemosterilants for boll weevils
were AI3-62904 and AI3-62961, both causing 100 percent sterility at 0.05 percent
concentration in the diet.

Of five styrylsulfonaphthylides and eight styrylsulfonanilides fed to adult
house flies of both sexes, only five compounds were effective sterilants
(table 2). Reduced fecundity was also observed in house flies treated with
AI3-62904, AI3-62986, and AI3-62987. However, compounds AI3-62771 and
AI3-62959 induced complete sterility in flies at 0.5 and 0.1 percent concentra-
tions, respectively, with no apparent effect on oviposition. “A. ipriori, we
might have expected a direct structure-activity relationship between the styryl
derivatives (III and IV) and their corresponding nonvinylic analogs (I and II),
but this was not always the case. For example, in previous studies with house
flies (2), 2 sulfonaphthylides, I, (R=4-(CH,) and I, R=4-(CH,0), gave 100 per-
cent sterility at a concentration of 0.01 percent in food. owever, in our fly
tests, the corresponding styryl analogs (AI3-62963 and AI3-62962) were virtually
ineffective at a concentration of 1 percent. Conversely, compound AI3-62959
was highly effective against house flies, but its corresponding nonvinylic
analog was ineffective at 1 percent (2).

Similar discrepancies were also apparent in the styrylsulfonanilide group.
For example, although sterility levels (in house flies) of two active styryl
derivatives A1l3-62987 and AI3-62986 roughly paralleled those of their corre-
sponding nonvinylic analogs, the nonvinylic analogs of three inactive styryl
compounds (AI3-62966, -62961, and -63102) caused 100 percent sterility in flies
at dietary concentrations of 0.1, 0.5, and 0.5 percent, respectively (3).

The effectiveness of these compounds in male insects was not extensively
investigated. However, AI3-62771 induced 46 percent sterility in male flies
at a 1 percent concentration. Interestingly, the sterilizing activities in
flies were uniformly greater when the compounds were added to regular diets
rather than to sugar diets.

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TABLE 2.--Chemosterilant activity of 5 effective styryl analogs
fed to adult house flies

Percent sterility 1/

AI3-No. Concentration ingder Tor
percent Sugar Fly food ;
6277 i 0 30 100
150) soe ay 46
$2) ses 100
2) =o 86
5 Alo) Sa 29
62904 0 0 3.4/1 99
5 = 3/100
25 == 65
62959 2! 1.0 0 100
5) ——— 100
25 = 100
25 aS ay 10
i === 100
05 == 28
62986 GO) 228/190 =
5 TAL 2 ene
25 === aloe
il = 86
62987 0 3/100 354/499
16 78

1/ Based on number of eggs that developed pupae. Sterility
of controls approximately 10 percent.

2/ Treated males crossed with untreated virgin females.

3/ No oviposition.

4/ Adult mortality >75 percent.

5/ Structure Met eR=2-thienyal~

In summary, 11 styrylsulfonamides were effective sterilants against boll
weevils and house flies. Because of their extremely high toxicity to weevils
and because of their low sterilizing effectiveness against house flies
(relative to their nonvinylic analogs), the practical utility of these
sterilants for reproductively controlling these insects remains doubtful.

LITERATURE CITED

Ge Bantlketre Hani e967, Genetic markers) ainwthe. bola weevil.) J.) Hered.
58:159-163.

@2) aDeMdtliog VA By. bomkoviec. Avi (B.. sand nyecuRw bei 1974.) insect chemo—
Ssterilants. Sulfonamides. J. Agr. Food Chem. 22:197-199.

(3) ,eborkovec,, “Aw Be, and Hye, Ra Lb. 19772. Insect, chemosterilanets ;
Analogues of 2,5-dichloro-N-(2,4-dinitrophenyl)benzenesulfonamides.
J. Agr. Food Chem. 25:81-83.

C4) mabye OOR. (ls. LaBrecque,, iG. Ga.vand Gouck, H. KK. (1966.4, Screening, tests
of chemicals for sterilization of adult house flies. J. Econ. Entomol.

59: 485-486.

(5) SS WOOdsS ChmWeeme BOnKOVICGs An (Bos, ands herrye. Ps Hee | LO7Sce. Cheno—
sterilants for the house fly: Further screening tests. J. Econ. Entomol.
66: 38-44.

CO) wiGasG. Rey he wanduDavich),. iB. h966e5) Bold weevalisna in iC. Ny oma th
Cedi), Insect Colonization and Mass Production, ch. 27. Academic Press,
New York.

CHP Oltiver. Ji.) E.j7and DeMilos Aw Be. 1975.0 A Knoevenagel type synthesis: of
styrene-w-sulfonamides. Synthesis (5):321-322.

8) @aWianderzants Her so.-and Davaichs fe 1B. 95G-. jLaboratony rearing, or nehie
boll weevil. A satisfactory larval diet and oviposition studies. J.
Econ. Entomol. 51:288-291.

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