Insecticidal Efficiency of Petroleum Fractions and Synthetic Isoparaffins G . W. PEARCE and P. J. C H A P M A N
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New York State Agricultural Experiment Station, Geneva, Ν. Y.
Two series of petroleum fractions and a series of syn thetic isoparaffins prepared by the New York State Agricul tural Experiment Station are described briefly. Their in secticidal efficiency on three unrelated pests—oriental fruit moth, European red mite, and cottony peach scale— is reported.
T h e relation of the constitution of saturated petroleum fractions to their insecticidal efficiency was shown i n the case of a single insect species i n a previous paper (9). T o ex tend this study the Citrus Experiment Station of the University of California, the Shell Oil Co., and the N e w Y o r k State Agricultural Experiment Station cooperated to include other species and to examine the insecticidal properties of various hydrocarbon composi tions derived directly or indirectly from petroleum as well as synthetic hydrocarbons of known constitution. Part of the program planned for the N e w Y o r k Station consisted of: The preparation of suitable quantities of narrow boiling petroleum fractions for insec ticidal and phytotoxicity evaluation at cooperating laboratories. The preparation of sufficient quantities of individual hydrocarbons of known structure i n the range of Cie to C M for biological evaluation. T w o series of petroleum fractions and a series of synthetic isoparaffins which were prepared are described briefly i n this paper together with a report of their insecticidal ef ficiency on three unrelated pest species. T h e materials were tested on the eggs of the oriental fruit moth, GrapholÛha molesta (Busck), the winter eggs of the European red mite, Paratetranychus pilosns ( C . & F . ) , and the newly hatched nymphs of the cottony peach scale, Pulvinaria amygdali (Ckll.). R i e h l and L a D u e (11) axe reporting results on the evaluation of the two series of petroleum fractions against California red scale and citrus red mite.
Isoparaffins Eleven isoparaffins having 16 to 34 carbon atoms per molecule were prepared i n quantities of 600 to 1000 grams. Table I presents a brief description of the compounds. Details of the methods used i n their synthesis and additional important physical properties w i l l be presented elsewhere (10). T h e purity of a l l compounds is estimated to be 95 mole % or better.
Petroleum Fractions The quantities of individual petroleum fractions necessary for the planned biological testing required the construction of a special vacuum fractionating column. A column of suitable size and efficiency was built and utilized i n the fractionation of two waterwhite 12
AGRICULTURAL APPLICATIONS OF PETROLEUM PRODUCTS Advances in Chemistry; American Chemical Society: Washington, DC, 1952.
13
PEARCE AND CHAPMAN—PETROLEUM FRACTIONS AND SYNTHETIC ISOPARAFFINS
Table I.
Description of Isoparaffins Viscosity at 100° F . Saybolt Kinematic cs seconde 6
Empirical Formula
Designation
Name
PI P2a P3 P4 P5 P27 P22 P6 P7 P8 P9
7n-Propyltridecane 7n-Hexyltridecane 8n-Hexylpentadecane 9 n- Hexylne pta decane 9n-Octylheptadecane 1 In-Amy 1 he ne ic osa ne 6,1 l-Di-n-amylhex&decane 9n-Octyleicosane 9n-Octyldocoeane 9n-Octyltetracosane 9 n-Octylhexacosane
Theor. M.W.»
4
M
m
w
35.0 40.7 44.9 49.7 55.2 59.1 65.2 66.0 75.7 87.5 101.9
2.69 4.50 5.82 7.31 8.93 10.08 11.80 12.03 14.61 17.68 21.04
226.4 268.5 296.6 324.6 352.7 366.7 366.7 394.7 422.8 450.8 478.9
CieH»4 C19H40 C«H 4 CsiHa C„H C HU CMHM CtsHa C He> CisHe« C|4H70
• Calcd. using C - 12.01; H - 1.008. Values will vary slightly from final values of Pearce and Schiessler (10). 6
oils representing a paraffinic type and a naphthenic type. The paraffinic oil was the same as that employed b y Pearce et al. (9) except that it was from a different year's manufac ture and is designated as 46-M20. The naphthenic oil, supplied b y the Shell O i l Co., consisted of an exhaustively refined California spray oil blending stock. T h e two oils were separated into 1 0 % fractions b y vacuum fractional distillation; corresponding frac tions obtained i n replicated distillations were combined as composite fractions. These composite fractions were used for a l l physical property data and biological tests to be re ported. Figures 1 and 2 show the Engler boiling point characteristics at 1 m m . of mercury of the two oils and their fractions. A summary of the boiling point data is presented i n Table I I . These data were obtained i n a specially designed vacuum Engler distillation appara tus at pressures ranging from 0.2 to 2.0 m m . of mercury; a l l values were extrapolated to 1 m m . b y means of a Brown-Coats chart (1). A summary of important physical and other characteristics of the parent oils and their fractions is presented i n Table I I I . The molecular weights were estimated from the viscosity correlations of Hirschler (6, 7) and b y direct determination with a modified Menzies-Wright apparatus (8). The other data were obtained essentially b y the same methods used b y Pearce et al. (9).
Insecticidal Evaluation O r i e n t a l F r u i t M o t h Tests. I n general the methods utilized i n previous studies (9) were employed for the insecticidal evaluation of the materials. T h e results have Table II.
Summary of Boiling Point Data on Oils 46-S1 and 46-M20 and Their Fractions Cumulative % of Original Oil
46-81 Fract.
1 2 3 4 5 6 7 8 9 Residue 10
46-M20 Fract.
1 2 3 4 5 6 7 8 9 Residue 10
%
10%
Distilled 90% 50% B . P . at 1 mm., ° F .
B . P . Range 10-90%, ο
50% B . P . 760 M m . ο
Jj^
•C
Ï0 20 30 40 50 60 70 80 90 100
263 210 246 258 274 287 302 314 326 340 361
315 235 261 276 289 302 312 324 336 350 381
367 251 275 290 304 316 324 335 348 362 423
104 41 29 32 30 29 22 21 22 22 62
660 560 590 610 625 640 655 670 685 700 740
349 293 810 321 329 338 346 354 363 371 393
Ï0 20 30 40 50 60 70 80 90 100
289 220 271 290 310 328 346 360 378 404 429
353 254 286 308 325 342 362 376 395 420 454
435 270 299 321 339 356 374 388 406 436 483
146 50 28 31 29 28 28 28 28 32 54
705 580 620 650 670 690 715 735 755 785 830
374 304 327 343 354 366 379 391 402 418 443
AGRICULTURAL APPLICATIONS OF PETROLEUM PRODUCTS Advances in Chemistry; American Chemical Society: Washington, DC, 1952.
ADVANCES IN CHEMISTRY SERIES
fc^c
been expressed i n terms of the m i n i m u m dosage per unit of leaf surface area required t o produce a k i l l or control efficiency of 9 5 % of the eggs of the oriental fruit m o t h o n that β>Ο *h.^«0*0^·^CCtO CO*«CO*«0"
