GB2081096A - Composition for control of colonial insects - Google Patents

Abstract

The present invention is directed to a composition and method for use as an agent for the control of certain colonial insects, for example ants and termites, of a class of N-(2,2- difluoroalkanoyl) -o- phenylenediamines.

Description

SPECIFICATION Composition for control of colonial insects This invention is directed to a composition for use as an agent for the control of certain colonial insects, i.e., ants and termites, of a class of N - (2,2 - difluoroalkanoyl) -o - phenylenediamines. The present invention is also directed to methods of using a class of N - (2,2 - difluoroalkanoyl) - 0 - phenylenediamines for the control of certain colonial insects, especially the imported red fire ant (Solenopsis invicta).

In the prior art are U.S. Patents 4,011,341, 4,108,631, and Re. 29,508, which result from the same original filing. These patents are directed to a series of o-phenylenediamine compounds including some of those to be employed as active agent in the presently claimed method and composition. The reference o-phenylenediamine compounds are taught to be useful as insecticides; but none of the numerous insect species listed in these patents is a colonial insect.

U.S. Patent 3,989,840 is directed to the use of the same series ofo-phenylenediamines as ectoparasiticdes. The publications in the following three articles further describe the ectoparasiticidal activity of compounds of this series: Experientia 36, 189 (1980); Southwestern Entomolgist4(4), 311 (Dec. 1979); Insecticide andAcaricide Tests, 3 (The Entomological Society of America, 1978), entries 260,265,267, and 269. Also van Lier et al., in the Abstract of Society of Toxicology Meeting at Washington D.C., March 10, 1980, "Disposition of a New Ectoparasitic Agent in the Rat", describe the disposition of one of the compounds of this series in the rat.

Another class ofo-phenylenediamines, some of which also serve as active agent in the method of the present invention, is disclosed in U.S. Patent 3,557,211. The reference describes the compounds as exhibiting insecticidal activity against Mexican bean beetle, Southern armyworm, aphid, housefly, and two-spotted spider mite. None of these is a colonial insect.

The present invention is directed to a composition and method for eradicating a colonial insect colony comprised of insects of the orderHymenoptera, familyFormicidae, or the orderisoptera, family Termitidae, which comprises supplying to the colony an effective amount of an active agent, the active agent being one or more compounds of the class of N - (2,2 - difluoroalkanoyl) - o - phenylenediamines.

The present invention relates to an edible bait composition suitable for ingestion by insects of the orderHymenoptera, family Formicidae, which comprises (1) an oil or fat; (2) a carrier having an oil capacity of at least 15 percent; and (3) an active agent which is a compound of the general formula

wherein: R1 is halo, CF3, CF2H, or CF2Cl; one of R2 and R3 represents a 2,2 - difluoroalkanoyl radical of the formula

wherein R4 is H, Cl, F, difluoromethyl, or trifluoromethyl; and the other of R2 and R3 represents H, the same 2,2-difluoroalkanoyl radical represented by the first of R2 and R3, a radical of the formula

wherein R5 is C1-C4 alkyl or phenyl, CZ-Cs alkanoyl, benzoyl, or halogenated C,-C5 alkanoyl, subjected to the limitation that the alpha position bears at least one of the following substituents: H, Cl, Br, or l; subject to the further limitation that when R3 represents a 2,2-difluoroalkanoyl radical, R2 is a group other than H.

Also the present invention relates to a method for eradicating a colonial insect colony comprised of insects of the orderHymenoptera, family Formicidae, or the orderlsoptera, family Termitidae, which comprises supplying to the colony an effective amount of an active agent of a compound of formula I as above defined.

Preferred compounds to be employed in the composition and method of the present invention are those of the general formula

wherein R6 is chloro ortrifluoromethyl; R7 is a 2,2difluoroalkanoyl radical as above defined; and Ra is H or the same 2,2-difluoroalkanoyl radical represented by R7.

The compounds serving as active agent in accordance with the present invention are prepared by known procedures; see the teachings of U.S. Patent 3,557,211 and U.S. Reissue Patent 29,508. In general the compounds are prepared by acylation of an o-phenylenediamine of the formula

where R' is defined as in formula I above. Where R2 is a 2,2-difluoroalkanoyl radical and R3 is H, or where both R2 and R3 are the same 2,2-difluoroalkanoyl radical in formula I, the acylating agent is suitably a 2,2-difluoroalkanoyl halide or 2,2-difluoroalkanoic an hydride. Where one of R2 and R3 is a 2,2difluoroalkanoyl radical and the other is a group other than H or the same 2,2-difluoroalkanoyl radical, the two groups are introduced by sequential acylation reactions. The various acylation reactions are conducted in conventional procedures.

The orderHymenoptera, family Formicidae includes the numerous species of ants. The order Isoptera, family Termitidae includes the various species oftermites. Representative species are the following: Ants (order Hymenoptera, family Formicidae) Argentine ant-lridomyrmexhumilis Pharaoh ant-Monomorium pharaonis Little black ant-Monomorium minimum Odorous house ant- Tapinoma sessile Thief ant-Solenopsis molesta Cornfield ant -Lasius alienus Pavement ant - Tetramorium caespitum Large yellow ant -Acanthomyops interjectus Small yellow ant -Acanthomyops claviger Black carpenter ant - Camponotus pennsylvanicus Red carpenter ant - Camponotus ferrugineus Florida carpenter ant - Camponotus abdominalis flo ridan us Brown carpenter ant - Camponotus casteneus Texas leaf-cutting ant-Atta texana Imported fire ant-Solenopsis geminata Black imported fire ant-Solenopsis richteri Red imported fire ant-Solenopsis invicta Southern fire ant -Solenopsis xyloni Leaf cutter ant -Atta cephalotex Leaf cutter ant -Atta sexdens (no common name) -Acromyrmex sp.

Big-headed ant-Pheidole megacephala Termites (orderlsoptera, family Termitidae) Eastern subterranean termite -Reticulitermes flavipes Arid-land subterranean termite -Reticulitermes tibialis Western subterranean termite -Reticulitermes hesperus Common dry-wood termite -Kalotermes minor Southern dry-wood termite -Kalotermes hubbardi Southeastern dry-wood termite -Kalotermes snyderi Dry-wood termite -Kalotermes schwartzi Pacific damp-wood termite -Zootermopsis an use tico llis Western dry-wood termite -Incisitermes minor Dam p-wood termiteParaneotermes simplicornis Formosan subterranean termite - Coptotermes formosanus Dry-wood termite -Criptotermes brevis Dry-wood termite - Criptotermes rospigliosi Subterranean termite -Heterotermes tenuis Subterranean termite - Coptotermes testaceous Subterranean termite -Rhinotermes nasutus Tree termite -Nasutitermes sp.

(no common name) -Ancistrotermes carithorax (no common name) -Microtermes subhyalinus The active agent offormula I in accordance with the present invention is employed for the control of ants and termites in manners conventional for the particular species.

In the case of ants, the present active agent of formula I exhibits the desirable attribute of delayed toxicity following ingestion; therefore, workers carry the active agent back to the hive and share it with other ants, a process known as trophallaxis. Accordingly, the present active agent is supplied in an edible, preferably attractant bait positioned nearthe colony or colonies. For ant species which infest pastureland or cropland, an edible bait containing the present active agent can be distributed uniformly on the infested land.

The amount of the present active agent of formula I which is effective to eradicate an ant colony will vary with factors such as the identity of the ant; the size and number of the colonies; the mode of application; and other factors. For application to pastureland and cropland, good results are generally obtained by application of from 0.002 to 0.25 kg/hectare (1 to 100 grams/acre) and preferably from 0.002 to 0.025 kg/hectare (1 to 10 gramstacre); such amounts are readily supplied by applying from 0.056 to 11.2 kg/hectare (0.05 to 10.00 Ibs/acre), preferably 1.12 to 5.6 kg/hectare (1.0 to 5.0 Ibs.lacre), of a bait comprising 0.05 to 3.00 weight percent, and preferably 0.1 to 1.0 weight percent, of the present active agent.For eradication of isolated colonies, good results are generally achieved with baits containing the present active agent at concentrations of 0.01 to 1.00 weight percent. In general, it is desirable to use a minimum effective amount, to minimize exposure to non-target species. The optimal use for control of fire ants on pastureland and cropland appears to be about 1.12 kg/hectare of a 0.75 weight percent formulation, to supply about 2 to 4 gramsiacre.

Baits containing the present active agent can be prepared in a conventional manner. Typically the active agent is dissolved in an oil or fat. The oil or fat can be a vegetable oil such as soybean oii, sesame seed oil, coconut oil, cottonseed oil, safflower oil, peanut oil, corn oil, or synthetic oil such as ethylolate or high boiling petroleum distillates such as mineral oil; or an animal fat such as lard or tallow. Because of its low cost and ready availability, soybean oil is generally preferred. The solution can be supplied as such even at a low volume application rate of a lipophilic solution, but is preferably distributed on a carrier such as puffed corn, corncob grits, starch, or the like. In general, any adsorbent material with ader quate oil capacity, such as 15 percent or greater, which is not offensive to ants, is acceptable. Pregelled defatted corn grits has been found to be preferable because of its higher oil capacity.

The bait can also include an attractant, such as lecithin or any nutritive substance with particular appeal to the ant species.

In the case of termites, repellency is a more important mode of control, although as shown by the data below, the present active agent of formula I exhibits both toxicant and repellent modes of action. Termite control typically takes the form of treating soil sur rounding houses and other buildings sought to be protected against termites, although other conventional methods of application can also be employed with the present active agent.

For termite control, the present active agent of formula I is formulated in conventional manners.

The agent can be dissolved in a solvent orformulated as a water emulsion, for application to soil. For example, the present active agent can be formulated as a wettable powder, e.g., Ingredient Weight Percent 3-nitro-5-(trifluoromethyl)-N1 - 50% (pentafluoropropionyl)-o-phenylene- diamine Stepanol ME (Stepan Chemical Co. 5% brand of sodium lauryl sulfate) Polyfon O (an anionic surfactant 5% sold by Westvaco Corporation Polychemicals Dept. and comprising a sodium lignosulfonate) Zeolex 7 (a sodium silicoaluminate 5% sold by J. M.HuberCorp.) Bardens clay 35% or as an emulsifiable concentrate, e.g., Ingredient Weight Percent 3-nitro-5-(trifluoromethyl)-N'- 25% (pentafluoropropionyl) < i-phenylene- diamine acetophenone 63% Sponto 1003 (a surfactantsold 12% byWhitco Chemical, comprising a blend of oil-soluble metal sulfonates and polyoxyethylene ethers) The wettable powder or emulsifiable concentrate can then be dispersed in water to constitute a soiltreating formulation. Similarly, the present active agent of formula I can be dissolved in a solvent, including aromatics such as xylene, toluene, and aromatic naphthas; alcohols; esters; and acetonitrile, to constitute a soil-treating formulation.The present active agent generally gives effective termite control when employed in formulations comprising From 0.05 to 1.0% of active agent, applied at standard termite control application rates such as 3.78 liters per 4.6-9.29 m2 (1 gallon per 5-10 sq. ft.) and 3.78 liters per 0.76-1.52 m. (1 gallon per2 1/2 - 5 lineal ft.).

The present active agent of formula I is believed to undergo a chemical conversion in warm-blooded animals, illustrated belowforthe single active agent 3 - nitro -5- (trifluoromethyl) - N1 - (2,2,3,3 - tetraf- luoropropionyl) - 0 - phenylenediamine:

See the Abstract of Society of Toxicology Meeting at Washington, D.C., March 10, 1980, "Disposition of a New Ectoparasitic Agent in the Rat", van Lier et al.

The resulting benzimidazole compound, again in warm-blooded animals, is believed to be more toxic. See Experientia, 36(1980), 189 et seq., "Systemic Animal External Parasiticidal Activity of Perfluoroalkylbenzimidazoles and Their Aminoanilide Precursors", by Boisvenue et al.

While no data is available to indicate the fate of the present active agent in ants, it is believed preferable to formulate the present active agent in a manner two minimize conversion to the benzimidazole, since a delayed effect is desired in the control of ants. For example, the formulation should ideally be neutral or slightly acidic.

The practice of the present invention is illustrated by the following examples. These examples are not to be construed as limitating as other compounds of formula I could be used. All percentages given are by weight.

EXAMPLE 1 3- Nitro -5- (trifluoromethyl) - N' - (2,2,3,3- tetraf- luoropropionyl) - o - phenylenediamine was evaluated for the control of the red imported fire ant (Sol- enopsis invicta, variety Buren). Four separate tests were conducted, each under laboratory conditions, with worker ants.

Each test was conducted in 30 ml. disposable plastic medicine cups (40 mm internal dimension at the top, tapering to 32 mm internal dimension at the botton, 38 mm high). A hole (6 m diam.) was drilled through the bottom of each cup and a layer of plaster of Paris and builders' cement 9:1 ratio) was poured over the bottom. The plaster mixture covered the hole and acted as a wick to draw up water when the cup was placed on a wet peat moss bed. (Moisture is necessary to keep the humidity in the cups high and thereby prevent desiccation of the ants. The cement is added to make a hard mixture through which the ants cannot tunnel and escape).

Twenty worker ants from field-collected colonies were placed in each test chamber about 24 hours preceding start of the test. This pretreatment holding period allowed time for recovery of the ants from handling and for orientation to the containers.

The candidate compound was dissolved directly in the food material, soybean oil. The toxic solution was offered to the ants on cotton swabs saturated with the material and placed in the test chamber in small vial caps.

The ants were allowed to feed as desired on the toxic bait for 24 hours. Afterthis exposure period, the toxicant was removed from the chamber and the ants remained without food for an additional 24 hours. At the end of this time new vial caps containing cotton swabs saturated with soybean oil were placed in the chamber and left for the remainder of the test period. Knockdown and mortality counts were made at intervals of 1,2,3,6,8, 10, 13 and 14 days following initial exposure. Each test consists of three replications. Room temperature was maintained at 26.6 + 1.1 C.

Results were as reported in the following table.

TABLE I Concn. of compound in Average percent knockdown and kill No. of soybean oil after indicated no. ofdays Treatment tests al food 1 2 3 6 8 10 14 3 - Nitro - 5 - (trifluoro- 4 0.01 1 1 1 1 7 16 29 methyl)- N1- (2,2,3,3- .1 1 6 19 64 82 89 95 tetrafluoropropionyl) - 1.0 22 55 86 100 o-phenylenediamine 4 .01 0 1 1 7 19 34 58 Mirex (standard) 1 1 2 17 66 84 92 100 1.0 0 57 90 100 Soybean oil 4 0 2 3 7 9 11 16 (check) a/ Each test consisted of 3 replicates at each concentration, with 20 worker ants per replicate.

EXAMPLES 2- 11 A number of the o - phenylenediamines to be employed in accordance with the present invention were also evaluated for activity against the red imported fire ant (Solenopsis invicta, variety Buren). The tests were conducted in essentially the same procedures described in the preceding example, with the following minor differences: the peat moss bed was replaced by a saturated 6.4 mm (1/4 in. thick) foam pad, and the cups were placed in a tray and covered with a sheet of clean plexiglass to prevent rapid evaporation of the water from the foam pad.

The results were as reported in the following table.

TABLE IT Percent knockdown and mortality Treatment Concn. after indicated number days ( /0) 1 2 3 6 8 10 14 3 - Nitro - 5 - (trifluoro- 0.01 0 0 0 2 2 2 7 methyl) - N' - (penta- 0.1 0 2 3 27 35 43 48 fluoropropionyl)-o- 1.0 20 57 73 92 93 98 100 phenylenediamine 3 - Nitro - 5 - (trifluoro- 0.01 0 0 0 0 0 0 7 methyl)-N1,N2-bis(tri- 0.1 3 5 12 37 38 42 53 fluoroacetyl)-o- 1.0 7 23 43 67 73 78 83 phenylenediamine 3-Nitro-5-(trifluoro- 0.01 2 3 3 3 7 7 10 methyl)-N-acetyl- 0.1 0 0 0 5 5 5 18 N2-(trifluoroacetyl)- 1.0 0 2 2 7 8 12 20 o - phenylenediamine 3-Nitro-5-chloro- N',N2- 0.01 3 5 5 5 7 10 17 bis(trifluoroacetyl) -o - 0.1 3 17 33 60 60 63 75 phenylenediamine 1.0 22 72 85 95 95 98 100 4 3-Nitro-5- (trifluoro- 0.01 2 2 2 2 3 5 7 methyl)-N1-(trichloro- 0.1 0 0 2 5 8 10 22 acetyl) - N2- (trifluoro- 1.0 2 25 30 43 45 50 57 acetyl) -o - phenylenediamine 3-Nitro-5-(trifluoro- 0.01 2 2 2 2 5 10 33 methyl)-N,N-bis- 0.1 5 27 33 53 55 55 72 (2,2,3,3- tetrafluoro- 1.0 45 73 77 88 88 93 98 propionyl) -o -phenylene- diamine TABLE II cont Percent knockdown and mortality Treatment Concn. afterindicatednumber ofdays (%) 1 2 3 6 8 10 14 N 3 - Nitro - 5 - (trifluoro- 0.01 2 2 2 3 3 5 5 methyl)- N' -(methoxy- 0.1 2 2 3 15 20 22 38 carbonyl)-N2--(difiuorn- 1.0 2 23 33 42 42 43 45 acetyl) - 0 - phenylene diamine 3-Nitro-5-chloro- N',N2- 0.01 5 5 7 8 8 8 8 bis(2,2,3,3-tetrafluoro- 0.1 0 2 5 15 15 17 17 propionyl) -o - phenylene- 1.0 15 45 55 63 67 67 73 diamine 3 - Nitro - 5 - (trifluoro- 0.01 3 7 7 12 17 20 23 methyl)-N1-acetyl-N2- 0.1 2 3 7 8 13 23 23 (2,2,3,3 -tetrafluoro- 1.0 0 8 28 65 67 72 78 propionyl) -o - phenylene diamine 3 - Nitro - 5 - (trifluoro- 0.01 5 5 5 10 12 17 27 methyl)-N-(2,2,3,3- 0.1 0 0 2 3 5 8 15 tetrafluoropropionyl)- 1.0 5 8 10 10 10 12 25 N2- acetyl -o - phenylene diamine Mirex 0.01 2 2 3 3 8 18 42 (standard) 0.1 0 0 3 50 67 68 92 1.0 0 25 60 100 Soybean Oil - 1 1 2 2 4 12 15 (check) EXAMPLE 12 3 - Nitro -5- (trifluoromethyl) - N' - (2,2,3,3 tetraf- luoropropionyl) - o - phenylenediamine was evaluated against laboratory colonies of the red imported fire ant (Solenopsis invicta, variety Buron).

The candidate toxicant was formulated at concentrations of 1.0,2.5, and 5.0% in soybean oil and the resulting formulations were then used to prepare baits containing 30% of one of the respective formulations and 70% pregetled defatted corn grits (on a weight by weight basis). Normal colonies of ants, which had been starved for 5 days, were exposed to the baits for 24-96 hours and then the baits were replaced with the standard laboratory diet. Mortality counts and general observations on the condition of the colonies were recorded weekly. A test waster- minated when the queen, brood, and 90% of the workers were dead. Duplicate tests were conducted with each concentration of the candidate toxica nt.

The results are shown in the following table.

TABLE III Concentration Percent mortality in colony at indicated ofcompound weeks after initial exposure to bait * in soybean oil 1 2 3 4 8 1.0 95 97 98 99 D 1.0 99 D 2.5 99 99 99 D 2.5 99 D 5.0 D 5.0 D Check O 0 0 1 5 * D = Death of colony; ants were maintained on the standard laboratory diet following the 24-96 hour exposure to the tre ated bait.

The foregoing results indicate that the 5.0% concentration killed the colonies within a week. The 2.5% concentration killed 99% of the ants within a week and resulted in the death of 1 colony within 2 weeks and the other colony within 4 weeks. The 1.0% concentration was 95-99% effective within a week and resulted in the death of 1 colony within 2 weeks and the other colony within 8 weeks.

EXAMPLE 13 3 - Nitro - 5 - (trifluoromethyl) - N' - (2,2,3,3 -tetra- fluoropropionyl) - o - phenylenediamine was formulated in two baits suitable for supplying the compound to ants.

The compound was dissolved in acetone and then in refined soybean oil and the solution was mixed with pregelled defatted corn grits. The acetone was evaporated (a small portion of the 3 - nitro - 5 - (tri- 4 fluoromethyl) - N' - (2,2,3,3 - tetrafluoropropionyl) o - phenylenediamine crystallized out).

The composition of the resulting baits was as follows: Bait #1 =a75% Amount %oftotal bait 3-nitro-5-(trifluoro- 510 grams 0.75% methyl)-N' -(2,2,3,3tetrafluoropropionyl)o-phenylenediamine refined soybean oil 18.5 kilograms 27.25% pregelled defatted 49 kilograms 72% corn grits Bait &num;2 = 1.5% Amount %oftotal bait 3-nitro-5-(trifluoro- 1020 grams 1.5% methyl)-N1-(2,2,3,3- tetrafluoropropionyl)o-phenylenediamine refined soybean oil 18 kilograms 26.5% pregelled defatted 49 kilograms 72% corn grits EXAMPLE 14 3 - Nitro - 5 - (trifluoromethyl) - N1 - (2,2,3,3 -tetra- fluoropropionyl) -o - phenylenediamine was also 25 formulated in a 1% bait The compound was dissolved in methylene chloride (6 kilograms) and then in refined soybean oil; the solution was added to textured corn grits and the methylene chloride allowed to evaporate prior to use.

The composition of the resulting bait was as follows: Amount %oftotal bait 3-nitro-5-(triflouro- 0.3 kilogram 1% methyl)-N' -(2,2,3,3tetrafluoropropionyl)o-phenylenediamine refined soybean oil 9 kilograms 30% textured corn grits 20.7 kilograms 69% EXAMPLE 15 3- Nitro -5- (trifluoromethyl) - N' - (2,2,3,3- tetra- fluoropropionyl) -o - phenylenediamine was evaluated against the red imported fire ant (Solenopsis invicta) under field conditions. The tests were conducted at three separate locations in Georgia, two with fire ant mounds in coastal variety bermudagrass and the third with fire ant mounts in Pensacola variety Bahiagrass. For all three of the tests, the candid ate compound was formulated as described in Example 14. In each test, bait was supplied to five mounds.Visual observation at the time of supplying the bait indicated that the ants accepted the bait immediately. Observations were made on three dates after supplying the bait.

Results were recorded in terms of percent control.

The results were as reported in the following tables.

TABLE IV Trial 1 (coastal Bermuda grass)

Days Percent Control After Treatment Adult Eggs Larvae 12 50 - - 47 80 80 80 74 100 100 100 Trial 2 (coastal Bermudagrass)

Days Percent Control After Treatment Adult Eggs Larvae 13 50 - - 44 80 both eggs and larvae = 80 73 100 100 | 100 Trial 3 (Pensacola Bahiagrass)

Days Percent Control After Treatment Adult Eggs Larvae 25 80 - - 41 40 60 60 70 50 50 50 EXAMPLE 16 3 - Nitro - 5 - (trifluoromethyl) - N' - (2,2,3,3 -tetrafluoropropionyl) -o - phenylenediamine was evaluated further for the control of the red imported fire ant (Solenopsis invicta) under field conditions. The tests were conducted in three different locations in Georgia, and the compound (as a 1%granularfor- mulation prepared as described in Example 14) was applied at each location by a cyclone applicator to an infested plot 210' x 210' - at a rate of 0.028 kg/hectare (0.025 Ibs./acre).Three readings were made at each test site, and the results were as follows: TABLE V Trial 1 (coastal Berm uda grass)

Days Percent Control After Treatment Adult Eggs Larvae 12 70 47 60 80 80 74 95 100 Base colonies = 61/A Trial 2 (coastal Bemudagrass)

Days Percent Control After Treatment Adult Eggs Larvae 13 80 44 80 both eggs and larvae = 100 73 95 95 1 95 Base colonies = 25/A Trial 3 (Pensacola Bahiagrass)

Days Percent Control After Treatment Adult Eggs Larvae 25 80 - - 41 75 90 90 70 100 100 100 Base colonies = 34/A EXAMPLES 17-21 Various of the N - (2,2 - difluoroalkanoyl) - o phenylenediamines serving as the present active agent were evaluated as termiticides. The procedure employed was that described by Virgil K. Smith in the Journal of Economic Entomology, Vol. 72, No. 6 (December, 1979), page 877 et seq., for a soil toxicity test and a repellency test. Results are reported herein as hours required to control 97% of the termites for the soil toxicity test, and as repellent or not repellent in the repellency test. As reported in the reference, a compound was considered repellent if 21 or more of 30 termites were observed on the untreated soil at all 3 observation times. The results on both tests were as reported in the following table.

TABLE Vl Soil Toxicity Repellency Test Test

Hours reguired to Repellent ("rep") Conc. of control 97% of or no repellency Compound Compd in ppm test termites ("no rep" propionyl)-o-phenylenediamine 500 > 8 " 250 > 8 100 > 8 50 > 8 25 > 8 10 > 8 5 > 8 3-Nitro-5-(trifluoromethyl)-N' - 1000 8 rep (2,2,3,3-tetrafluoropropionyl)- 750 8 N2-acetyl-o-phenylenediamine 500 > 8 250 > 8 100 > 8 no rep 50 > 8 25 > 8 rep 10 > 8 5 > 8 no rep 3-Nitro-5-(trifluoromethyl)-N' ,N2- 1000 3 Rep bis-(2,2,3,3-tetrafluoropropionyl)- 750 3.5 o-phenylenediamine 500 4.5 250 8 100 > 8 no rep 50 > 8 25 > 8 10 > 8 5 > 8 3-Nitro-5-(trifluoromethyl-N1- 1000 2 rep (2,2,3,3-tetrafluoropropionyl)-o- 750 2.5 phenylenediamine 500 2.5 no rep 250 4.5 rep 3-Nitro-5-(trifluoromethyl)-N' - 100 > 8 rep (2,2,3,3-tetrafluoropropionyl)-o- 50 > 8 no rep phenylenediamine (cont.) 25 > 8 rep 10 > 8 rep 5 > 8 no rep 3-Nitro-5-(trifluoromethyl)-N1 - 1000 1 rep (pentafluoropropionyl)-o- 750 1 phenylenediamine 500 1 250 1.5 100 2 50 3 no rep 25 4.5 10 > 8 rep 5 > 8 no rep

Claims (19)

1. An edible bait composition suitable for ingestion by insects of the orderHymenoptera, family Formicidae, which comprises (1) an oil or fat; (2) a carrier having an oil capacity of at least 15 percent; and (3) an active agent which is a compound of the general formula

wherein R' is halo, CF3, CF2H,or CF2Cl; one of R2 and R3 represents a 2,2 - difluoroalkanoyl radical of the formula

wherein R4 is H, Cl, F, difluoromethyl, or trifluoromethyl; and other of R2 and R3 represents H, the same 2,2 - difluoroalkanoyl radical represented by the first of R2 and R3, a radical of the formula

wherein RS is C,-C4 alkyl or phenyl, C2-Cs alkanoyl, benzoyl, or halogenated C2-Cs alkanoyl, subject to the limitation that the alpha position bears at least one of the following substituents: H, Cl, Br, orl; subject to the further limitation that when R3 represents a 2,2 - difluoroalkanoyl radical, R2 is a group other than H.

2. A composition of Claim 1 wherein the active agent is a compound of the general formula

wherein R6 is chloro or trifluoromethyl; R7 is a 2,2 difluoroalkanoyl radical as defined in Claim 1; and RB is H or the same 2,2 - difluoroalkanoyl radical represented by R7.

3. The composition of Claim 1 or 2 wherein the oil or fat is a vegetable oil.

4. The composition of Claim 3 wherein the vegetable oil is soybean oil.

5. The composition of Claim 3 wherein the carrier is pregelled defatted corn grits.

6. The composition of Claim 1 or 5 wherein the active agent is 3 - nitro - 5 - (trifluoromethyl) - N' (2,2,3,3 - tetrafluoropropionyl) - o - phenylenediamine.

7. The composition of Claim 1 wherein the active agent is 3 - nitro - 5 - (trifluoromethyl) - N - (pentaf luoropropionyl) - o - phenylenediamine.

8. The composition of Claim 1 wherein the active agent is 3 - nitro - 5 - (trifluoromethyl) - N1,N2 - bis(trifluoroacetyl) -o - phenylenediamine.

9. The composition of Claim 1 wherein the active agent is 3 - nitro - 5 - chloro - N',N2 - bis(trifluoroacetyl) -o - phenylenediamine.

10. The composition of Claim 1 wherein the active agent is 3 - nitro - 5 - (trifluoromethyl) - N1,N2 bis - (2,2,3,3- tetrafluoropropionyl) - o - phenylenediamine.

11. A method for eradicating a colonial insect colony comprised of insects of the order Hymenopt- era, family Formicidae, or the orderlsoptera, family Termitidae, which comprises supplying to the colony an effective amount of an active agent of the general of the formula

wherein R' is halo, CF3, CF3H, or CF3CI; one of R2 and R3 represents a 2,2 - difluoroalkanoyl radical of the formula

wherein R4 is H, Cl, F, difluoromethyl, or trifluoromethyl; and the other of R2 and R3 represents H, the same 2,2 - difluoroalkanoyl radical represented by the first of R2 and R3, a radical of the formula

wherein R5 is C1-C4 alkyl or phenyl, C2-Cs alkanoyl, benzoyl, or halogenated C2-Cs alkanoyl, subject to the limitation that the alpha position bears at least one of the following substituents: H, Cl, Br, or I; subject to the further limitation that when R3 represents a 2,2 - difluoroalkanoyl radical, R2 is a group other than H.

12. A method of Claim 11 wherein the active agent is a compound of the general formula

wherein Rs is chloro ortrifluoromethyl; R7 is a 2,2 difluoroalkanoyl radical as defined in Claim 11; and R3 is H or the same 2,2 - difluoroalkanoyl radical represented by R7.

13. The method of Claim 11 wherein the active agent is 3 - nitro - 5 - (trifluoromethyl) - N' - (2,2,3,3 tetrafluoropropionyl) -o - phenylenediamine.

14. The method of Claim 11 wherein the active agent is 3 - nitro - 5 (trifluoromethyl) - N' - (pentaf luoropropionyl) - 0 - phenylenediamine.

15. The method of Claim 11 wherein the active agent is 3 - nitro - 5 - (trifluoromethyl) - N',N2 bis(trifluoroacetyl) -o - phenylenediamine.

16. The method of Claim 11 wherein the active agent is 3 - nitro - 5 - chloro - N',N2 - bis(trif luoroacetyl) - o - phenlenediamine.

17. The method of Claim 11 wherein the active agent is 3 - nitro - 5 - (trifluoromethyl) - N',N2 bis(2,2,3,3 tetrafluoropropionyl) -o - phenylenediamine.

18. The edible bait composition as defined in Claim 1, substantially as hereinbefore described with particular reference to the Examples.

19. The method as defined in Claim 11, substantially as hereinbefore described.