AU427238B2 - Insecticidal composition - Google Patents

Description

28,232/71 This invention relates to an insecticidal compo- sition and more particularly relates to a synergistic in- secticidal composition comprisingaft. Insecticide and dl-

propargyl phenylphosphonate.

The insecticide industry is continually evaluat- ing compounds to improve the activity of insecticides.

These compounds are referred to as "synergists", and an insecticidal composition containing a synergist is refer- red to as a "synergistic insecticidal composition". The insecticidal activity of such a composition is greater than the sum of the activity of the insecticide and the synergist. (In general, synergists have essentially no insecticidal activity at the concentrations employed In the Insecticidal compositions.) However, for various rea- sons, the discovery of a synergist is not an easy task. Dipropargyl phenylphosphonate is an ester having a structural formula as follows;

0 -P OCH2 C CH) 2

Examples of the carbamate insecticides are 2 isopropoxyphenyl N methylcarbamate (sold by Chemagro under the trademark Baygon) and the carbamates described

in U.S. Patent 3,362,871.

28,232/7 This invention also encompasses the preparation

of a synergistic insecticidal composition wherein a

mixture of two or more of the above-described insecticides

is used and/or a second synergist is used in combina-

tion with dipropargyl phenylphosphonate. The second syner- gist may be one of the known synergists, examples of which are safrole (4 allyl 1,2 methylenedioxybenzene),

iso safrole (4 propenyl 1,2 methylenedioxybenzene),

dihydrqsafrole (4 n propyl 1,2 methylenedloxyben-

zene)o, piperonyl butoxide, and derivatives thereof. Synergistic insecticidal compositions are bb- talned in accordance with this invention wherein the weight ratio of the insecticide portion to the synergist portion is from about 1:1 to about 1:10. Minor amounts of other substances may be added to the compositions of this invention in order to attain particular functional or esthetic effects. Examples of such substances are perfumes, corrosion-inhibitors, buffer- ing agents, fillers, wetting agents, flame retardanta, antioxidants, emulsifiers, ultraviolet radiation ab- sorbers', and disinfectants. The synergistic Insecticidal compositions of

this invention may be formulated in a number of ways to

permit convenient application by the user. For example, they may preferably be made up as pressurized compositions in which the composition in the can is in the form of an oil-in-water emulsion, a water-in-oil emulsion, or a solu- tion. Such pressurized compositions may be prepared to give space sprays or surface sprays. Pressurization can

28,232/71 be accomplished with any of the propellants used in the art, including liquefiable hydrocarbons (such as propane, butane, and isobutane); liquefiable fluorinated alkanes (such as dichlorodlfluoromethane, difluoroethane, and tetrafluoroethane); and compressible inert gases (such as nitrous oxide, carbon dioxide, and nitrogen). Pressurized solvent formulations may be pre- pared by dissolving the insecticide and the synergist in a suitable solvent, such as ethanol, naphtha, or mineral spirits and pressurizing with one of the aforementioned propellants. Oil-ln-water formulations may be prepared by emulsifying the insecticide and any other hydrophobia components in water and pressurizing with one of the above-noted propellants. These compositions can also be formulated for use in hand sprayers, pump sprayers, foggers, and the like. These non-pressurized formulations can be in the form.of water-ln-oil emulsions, oil-in-water emulsions, or solutions. They are prepared similarly to the pres- surized compositions except for the emission of the pro- pellant. This invention will be further illustrated by the following examples of preferred embodiments. How-

ever, it will be understood that these examples are In- cluded for purposes of illustration and are not intended to.limit the scope of this invention. Preparation of Dipropargyl Phenylphosphonate. A 2000 ml. flask equipped with stirrer, condenser (drying tube), and additional funnel is charged with 28.0

28,232/7t g. (0.50 mole) propargyl alcohol, 50.6 g. (0.50 mole) triethylamine, and 1000 ml. diethyl ether. The solution is cooled in an ice-water bath, and 48.8 g. (0.25 mole) phenylphosphonic dichloride in 150 ml. ether is added slowly to the stirred, cooled solution (4 hours). The white solids are filtered from the reaction mixture and washed with ether. The ether solution was washed with water (2 x 100 saturated sodium bicarbonate (3 x 100 and dried over anhydrous magnesium sulfate, The ether is removed, and the crude ester is vac'uum- distilled. Theester has a boiling point of 141 to 142 0 C. (0.14 mm.) and nD2 2 1.5254. The structure of dipropargyl phenylphosphonate is confirmed by nuclear magnetic reso- nance and infrared spectra.

EXAMPLE 1 28.232/71 A synergistic insecticidal composition is

prepared by dissolving one part Baygon and four parts

dipropargyl phenylphosphonate in ethanol Bioassays that

establish the male German roach and female housefly

mortalities are conducted by applying 0.5 microliter of

the composition on the insect's ventral abdomen. Each

test is replicated twice with 25 male German roaches and

female houseflies that have been anesthetized with

carbon dioxide. Mortality readings are recorded 24 hours

after the initial treatment. The following results are

obtained:

LD 5 0 (Micrograms/Insect)

H.P. G.R.

Baygon alone 0.51 0.31 Baygon 4 DIPPP .026 0.082 Synergistic ratio 19.6 3.8

-6 427238

The lais dfinng The clims dfinin 298,2327f invention are as follows: 1. An insecticidal composition comprising:

ajsioipyEtr i insecticide and dipropargyj phenyiphosphonate, the weight ratio of insecticide to dipropargyl Phenylphosphon~a being from 1:1 to 1:.10.

Thopin of cam Wherein said carbamate insecticide is 2 -isopropoxyphenyl -N -methyl carbamate. $.An insecticidal composition as. defined in claim 1 substantially as herein defined.-

DATED this TENTH day of MAY, 1972 S. C. JOHNSON SON, INC.

Patent Attorneys for the Applicant SFRU SON FERGUSON

427 238t

28f23271