AU750562B2 - New benzoylphenylurea insecticides and methods of using certain benzoylphenylureas to control cockroaches, ants, fleas, and termites - Google Patents

Description

AUSTRALIA

Patents Act COMPLETE SPECIFICATION

(ORIGINAL)

Class Int. Class Application Number: Lodged: Complete Specification Lodged: Accepted: Published: Priority Related Art: Name of Applicant: Dow AgroSciences LLC Actual Inventor(s): Laura Karr, Jeff Edwards, Ronald Sbragia, Brian Schneider, George Johnson Address for Service: PHILLIPS ORMONDE FITZPATRICK Patent and Trade Mark Attorneys 367 Collins Street Melbourne 3000 AUSTRALIA Invention Title: NEW BENZOYLPHENYLUREA INSECTICIDES AND METHODS OF USING CERTAIN BENZOYLPHENYLUREAS TO CONTROL COCKROACHES, ANTS, FLEAS, AND TERMITES Our Ref: 631443 POF Code: 112152/112152 The following statement is a full description of this invention, including the best method of performing it known to applicant(s): -1la- NEW BENZOYLPHENYLUREA INSECTICIDES AND METHODS OF USING CERTAIN BENZOYLPHENYLUREAS TO CONTROL COCKROACHES, ANTS, FLEAS, AND TERMITES This is a divisional application of Australian Patent Application 49797/97 the entire content of which is herein incorporated by reference.

Background of the Invention This invention provides novel benzoylphenylurea insecticides and novel methods of inhibiting cockroaches, ants, fleas, and termites.

A broad class of benzoylphenylurea insecticides is disclosed in U.S. Patent No.

3,748,356. European Patent Application 263438 discloses that certain N-substituted phenyl-N'-substituted benzoyl-N-methylureas are highly safe to beneficial aquatic Crustacea while exhibiting equal or superior insecticidal activities to non-alkylated analogs. Hexaflumuron, a commercially significant benzoylphenylurea, is disclosed in U.S. Patent No. 4,468,405. Use of hexaflumuron in methods of controlling termites is disclosed in W093/24011. Use 20 of hexaflumuron to control cockroaches is disclosed in W094/03066. The compound N-[3,5-dichloro-2-fluoro-4-1,1,2,3,3,3-hexafluoropropoxy)phenyl]-N'- (2,6-difluorobenzoyl)urea is disclosed in DE 3827133 and European Patent .*Application A 243,790, but there was no disclosure of the unexpected activity of the compound against cockroaches, ants, fleas, and termites.

*We have discovered that certain benzoylphenylurea compounds, some of which are novel, have substantially greater activity against cockroaches, ants, fleas, and •termites than would have been expected based on comparison with the closest prior art, hexaflumuron. Another significant property of the novel compounds 30 of the invention is their surprisingly low toxicity to Daphnia.

The discussion of the background to the invention herein is included to explain the context of the invention. This is not to be taken as an admission that any of the material referred to was published, known or part of the common general knowledge in Australia as at the priority date of any of the claims.

ionaSpcies\Div of49797.doc -2- Throughout the description and claims of the specification the word "comprise" and variations of the word, such as "comprising" and "comprises", is not intended to exclude other additives, components, integers or steps.

Summary of the Invention The invention provides novel compounds of the formula (II) F Cl

-OCF

2

CHFCF

3

(II)

wherein R 1 and R 2 are H, methyl, or ethyl, provided that at least one of R 1 and

R

2 is methyl or ethyl.

These compounds are especially useful as components of cockroach, ant, or termite baits.

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555555 S. W:\fionaSpcics'div of49797.doc WO 98/19542 PCT/US97/18199 Detailed Description of the Invention Intermediate 1: 2,6-difluorobenzovl isocvanate CONH2

CONCO

A mixture of 0.52 g of 2,6-difluorobenzamide and 0.33 ml of oxalyl chloride was stirred under reflux in 15 ml 1,2-dichloroethane overnight. Solvent was removed under vacuum and 10 ml 1,2-dichloroethane was added. Solvent was removed under vacuum to leave the title intermediate, which could be used directly or dissolved in 1,2-dichloroethane and stored for future use.

Intermediate 2: 3.5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxv)aniline CI Cl :F CF .H2NP OH F CF 3

H

2

-OCF

2

CFHCF

3 CI CI X522838 To a solution of 2.0 g of 4-amino-2,6-dichlorophenol in 40 mL tetrahydrofuran at 15 room temperature was added 0.7 g of 87% potassium hydroxide. The mixture was warmed to 400 C. and stirred for 10 minutes, then chilled to 0° C.

Hexafluoropropene was bubbled in for 5 minutes, and the mixture stirred at room temperature over night. It was then concentrated under vacuum to dryness. The residue was dissolved in 50 mL dichloromethane and washed with 20 mL brine 20 solution. The organic layer was separated and filtered through phase separation filter paper and then concentrated under vacuum to an oil. This was diluted with 50 mL dichloromethane and 50 mL heptane and re concentrated to give 3.05 g of dichloro-4-(1,1,2,3,3,3-hex-afluoropropoxy)aniline as a brown oil. Proton and 19

F

nmr spectra were consistent with the proposed structure.

WO 98/19542 PCT/US97/18199 Intermediate 3: 3,5-Dichloro-2-fluoro-4-(1,1,2.3,3,3-hexafluoropropoxv)aniline C F CI

SELECTFLUOR

H

2 N-O- OCFCFHCF 3 ECTO H 2 N--L OCFCFHCF, Cl CH 3 CN cI X522838 X549988 To a solution of 2.50 g 3,5-dichloro 4-(1,1,2,3,3,3-hexafluoropropoxy)aniline in mL acetonitrile under an atmosphere of nitrogen at room temperature there was added 2.57 g I -chloromethyl-4-fluoro-1 ,4-diazoniabicyclo[2.2.2] octane bis (tetrafluoroborate) SELECTFLUORTM (Air Products) portion wise over a minute period. The mixture was warmed to 700 C. over a one hour period, then cooled to room temperature and poured into 100 mL of saturated sodium bicarbonate solution. The product was extracted with 150 mL ethyl acetate. The organic layer was separated, washed with 50 mL of brine solution, separated, and dried over magnesium sulfate. The magnesium sulfate was removed by filtration, and the filtrate was concentrated under vacuum to give a dark oil 2.52 g. The product was chromatographed using a Michel-Miller low pressure silica gel column eluted with 6:1 heptane/ethyl acetate. Like fractions were pooled and concentrated under vacuum to a brown oil 1.19 g. The proton and 19 F nmr spectra were consistent with the proposed structure. Anal. calcd C9H4C2F7N10I: C, 31.24; H, 1.17; N, 4.05.

Found: C, 31.52; H, 1.15; N, 4.02.

Intermediate 4: 3.5-Dichloro-2-fluoro4-(1,1,2.3,3,.3-hexafluoropropoxy)-N- 20 ethyl aniline H2N OCF2CFHCFp OCF2CFHCF3 HOAc CI CI X549988 X572213 To a solution of 0.28 g 3,5-dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy) aniline in 8 mL glacial acetic acid at room temperature under an atmosphere of WO 98/19542 PCT/US97/18199 nitrogen was slowly added 0.31 g sodium borohydride. The addition was carried out over a 1.5 hour period through a solid addition funnel between 25-34° C. with ice water cooling. The mixture was stirred at room temperature over night. Then the reaction mixture was added to 80 mL water and the pH was carefully adjusted to 7 by adding solid sodium carbonate. The product was extracted with 80 mL ethyl acetate. The organic layer was separated, washed with brine solution, separated, and dried over magnesium sulfate. The magnesium sulfate was removed by filtration, and the filtrate was concentrated under vacuum to give a brown oil 0.29 g. The product was chromatographed using a Michel-Miller low pressure silica gel column eluted with 9:1 heptane/ethyl acetate. Like fractions were pooled and concentrated under vacuum to give 0.19 g of a tan oil. 1 H-NMR d 1.28 3H), 3.17 4H), 3.95 (bs, 1H), 4.94-5.21 (md, 1H), 6.59 1H). Anal. calcd C11H8Cl2F7N: C, 35.31; H, 2.16; N, 3.74. Found: C, 35.32; H, 2.14; N, 3.74.

Preparation of Products Compound 1: N-f3,5-Dichloro-2-fluoro-4-(1,1,2,33,3hexafluoropropoxy)phenyll-N'-(2,6-difluorobenzoyl)urea o

H

2

/.OCF

2

CFHCF

3 2,6-difluorobenzoyl isocyanate OCF 2

FHCF

3 HNOFH3 2-DCE H 0 A CI1,2-DCE F CI X549988 X550007 To a solution of 1.31 g 3,5-dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy) aniline in 5 mL 1,2-dichloroethane under an atmosphere of nitrogen at room temperature was added 0.87 g 2,6-difluorobenzoyl isocyanate dissolved in 10 mL :dichloroethane dropwise over a 10 minute period. The mixture was stirred, warmed to 400 C. for a one hour period, then concentrated under vacuum to a brown solid g. The mixture was chromatographed using a Michel-Miller low pressure silica gel column eluted with 4:1 dichloromethane/heptane. Like fractions were pooled and concentrated under vacuum to give 1.67 g of a light tan solid, mp 156-7° C. Proton WO 98/19542 PCT/US97/18199 -and 19 F nmr spectra were consistent with the proposed structure. Anal. calcd C17H7C2F9N203: C, 38.58; H, 1.33; N, 5.29. Found: C, 38.64; H, 1.40; N, 5.44.

Compound 2: N-f3,5-Dichloro-2-fluoro-4-(1,1,2,3,3hexafluoropropoxv)phenvll-N'-(2,6-difluorobenzov)-N-ethylurea F F CI H 0) S OCFCFHCF3 2.6-difluorobenzoyl isocyanate- OCF 2

CFHCF

3 CI 1.2-DCE F CI X572213 X570143 To a solution of 1.00 g 3,5-dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)-Nethyl aniline in 2 mL 1,2-dichloroethane under an atmosphere of nitrogen at room temperature there was added 0.54 g 2,6-difluorobenzoyl isocyanate dissolved in 6 mL dichloroethane dropwise over a 10 minute period. The mixture was stirred and warmed to 400 C. for a 1.5 hour period. Analysis by thin layer chromatography silica gel 4:1 heptane/ethyl acetate indicated incomplete reaction. To the mixture was added 0.13 g 2,6-difluorobenzoyl isocyanate in 1.5 mL 1,2-dichloroethane, and a the mixture was warmed at 400 C. for 2.5 hour. Analysis by TLC indicated complete reaction. The reaction mixture was concentrated under vacuum to give an oil 1.64 g, which was chromatographed using a Michel-Miller low pressure silica gel column eluted with 4:1 heptane/ethyl acetate. Like fractions were pooled and concentrated under vacuum to give a white solid 0.87 g, mp 106-14' C. Proton nmr and mass spectra were consistent with the proposed structure. Anal. calcd C19H11C2F9N203: C, 40.95; H, 1.99; N, 5.03. Found: C, 40.89; H, 1.92; N, 5.03.

Compound 3: N-13.5-Dichloro-2-fluoro-4-(1,1,2,33,3hexafluoropropoxy)phenvll-N'-(2.6-difluorobenzovl)-N'-ethvl urea F F C1C- I-CHCH3 KOH F90 c

OCF

2 CFHCF3 C-CH 2

CH

3 KO- OCF2CFHCF3 CNCN C- N OCF 2

CFHC

.i H H F ci DMF F CI X550007 X574158 Dissolve 1.65 g N-[3,5-dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]- N'-(2,6-difluorobenzoyl) urea in 10 mL N,N-dimethylformamide and add 0.22 g 87% WO 98/19542 PCT/US97/18199 potassium hydroxide. Chill to 0° C. and add 0.97 g iodoethane. Stir at 0° C. for a 7 hour period. Store in freezer at 0° C. over night. Analysis by thin layer chromatography silica gel dichloromethane shows product forming with starting urea remaining. The reaction was treated as above at 0° C. for the next two days.

Additional amounts of iodoethane, 1.94 g, and 0.10 g 87% potassium hydroxide were added. Pour reaction mixture into 50 mL brine solution and extract with 80 mL ethyl acetate. Separate organic layer and dry over magnesium sulfate. Filter drying agent and concentrate the filtrate under vacuum to a red oil 2.63 g. Chromatograph using a Michel-Miller low pressure silica gel column and elute with 2:1 heptane/dichloromethane. Pool like fractions and concentrate under vacuum to 0.18 g of a pink solid, mp 105-060 C. Proton nmr and mass spectra were consistent with the proposed structure. Anal. calcd Cl9H11C12F9N203: C, 40.95; H, 1.99; N, 5.03.

Found: C, 40.99; H, 1.85; N, 4.98.

Biological Activity German cockroach 2nd instars (Blattella germanica) Continuous, low-dose ingestion exposure (treated cornmeal) Rates: 0.19, 0.78, 3.12, 12.5, 50, 200 ppm LCso (ppm) Compound 21 days 42 days Compound 1 2.2 <0.78 Compound 2 0.35 0.26 Compound 3 8.0 hexaflumuron 200 200 Under continuous exposure, Compounds1, 2, and 3 were far more active than hexaflumuron.

WO 98/19542 PCT/US97/18199 German cockroach 2nd instars (Blattella germanica) Limited ingestion exposure (48 hr) to treated cornmeal Rates: 1, 10, 100, 1000, 10000 ppm LCso (ppm) Compound 21 days 42 days Compound 1 22.2 9.1 Compound 2 21.1 12.8 hexaflumuron 10,000 10,000 Under limited exposure, Compounds 1 and 2 were more potent than hexaflumuron at both 21 and 42 days after exposure.

Cat Flea (Ctenocephalides felis) Continuous exposure of larvae to treated media, impact on subsequent adult emergence Rates: 0.1, 1.0, 10, 100, 1000 ppm 9 .9 Compound LCso (ppm) LCo (ppm) Compound 1 2.8 22 Compound 2 12.7 18.6 hexaflumuron 65.7 333.5 lI Su compounds I and 2 were both tar more efficacious than hexaflumuron against cat fleas.

Subterranean Termite (Reticulitermes flavioes) Continuous exposure (56 days) to treated paper Rates: 0.78, 3.12, 12.5, 50, 200 ppm

-L

LCso (ppm) LT 50 (days) for Compound 35 days 56 days 200 ppm trt Compound 1 31.2 0.78 27.6 Compound 2 <0.78 <0.78 not calc.

hexaflumuron 200 1.3 33.8 WO 98/19542 PCTIUS97/18199 Under continuous exposure, Compounds 1 and 2 were more potent and quicker acting than hexaflumuron.

Subterranean Termite (Reticulitermes flavipes) Limited exposure (7 days) with mortality determined at 14, 28, 42, and 56 days33399 Compound LTs (days) for 10000 ppm treatment Compound 1 23.7 hexaflumuron 32.9 Under limited exposure, a high rate of Compound 1 induced more mortality earlier than did hexaflumuron.

Ant Studies Laboratory ant bait studies were carried out with Red Imported Fire Ant (RIFA) (Solenopsis invicta) and Pharaoh Ant (Monomorium pharaonis). Chitin synthesis inhibitors, such as the compounds of the invention, control ants by killing the molting larvae and/or pupae and potentially preventing the hatching of eggs.

Because adult workers are not affected, control is measured by effects on the brood.

The studies involved 3-4 day exposure to bait. These limited exposure studies more 15 accurately represent real world bait availability than continuous exposure.

S

S

*5

S

S.

Compound Concentration Species Time to Time to tested Achieve Achieve Brood Brood Reduction Reduction* Compound 1 RIFA 2 wks 3 wks 0.1% Pharaoh 4 wks NA (70% 13 wks) Hexaflumuron 0.1% RIFA NA NA 0.25% RIFA 4 wks 10 wks 0.1% Pharaoh NA NA Only concentration tested. NA did not achieve specified percent brood reduction.

Percent brood reduction achieved at end of study listed in parenthesis.

WO 98/19542 PCT/US97/18199 Compound 1 is significantly more potent than hexaflumuron based on a short exposure study with RIFA.

Activity against Daphnia 48 hr exposure to treated water Compound LC 50 (ppb) in water Compound 1 Compound 2 100 Compound 3 100 Hexaflumuron 68.1 Compounds 2 and 3, the alkylated derivatives of Compound 1, were much less active against Daphnia than were Compound 1 and hexaflumuron; this is surprising since the activities of Compound 1, 2, and 3 in cockroaches are quite similar.

Formulations In order to facilitate the application of the compounds of formula to the desired locus, or to facilitate storage, transport or handling, the compound is normally formulated with a carrier and/or a surface-active agent.

A carrier in the present context is any material with which the compound of formula 15 (active ingredient) is formulated to facilitate application to the locus, or storage, transport or handling. A carrier may be a solid or a liquid, including a material which is normally gaseous but which has been compressed to form a liquid. Any of the carriers normally used or known to be usable in formulating insecticidal compositions may be used.

20 Compositions according to the invention contain 0.0001 to 99.9% by weight active ingredient. Preferably, compositions according to the invention contain 0.001 to 10.0% by weight of active ingredient though proportions as low as 0.0001% may be useful in some circumstances.

WO 98/19542 PCT/US97/18199 Suitable solid carriers include natural and synthetic clays and silicates, for example natural silicas such as diatomaceous earths; magnesium silicates, for example talcs; magnesium aluminium silicates, for example attapulgites and vermiculites; aluminium silicates, for example kaolinites, montmorillonites and micas; calcium carbonate; calcium sulphate; ammonium sulphate; synthetic hydrated silicon oxides and synthetic calcium or aluminium silicates; elements, for example carbon and sulfur; natural and synthetic resins, for example coumaronne resins, polyvinyl chloride, and styrene polymers and copolymers; solid polychlorophenols; bitumen; waxes; agar; and solid fertilizers, for example superphosphates. Cellulose based materials, for example wood, sawdust, agar, paper products, cotton linter, or Methocel®, as well as the other solid carriers that are themselves attractive to or at least non-repellant to termites are particularly suitable and preferable. Mixtures of different solids are often suitable. For example, a mixture of wood flour and agar formulated as a moisture containing solid would be preferable.

Suitable liquid carriers include water; alcohols, for example isopropanol and glycols; ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone; ethers; aromatic or aliphatic hydrocarbons, for example benzene, toluene and xylene; petroleum fractions, for example kerosene and light mineral oils; chlorinated hydrocarbons, for example carbon tetrachloride, 20 perchloroethylene and trichloroethane; polar organic liquids, such as dimethyl formamide, dimethyl acetamide, dimethyl sulfoxide and N-methylpyrrolidone; oils derived from plants, such as corn oil and peanut oil. Mixtures of different liquids are often suitable, for example a mixture of isophorone with a polar organic solvent such S as N-methylpyrrolidone, as are mixtures of solid and liquid carriers.

Pesticidal compositions are often formulated and transported in a concentrated form which is subsequently diluted by the user before application. The presence of small amounts of a carrier which is a surface-active agent facilitates this process of dilution. Thus it is suitable to use at least one carrier in such a composition which is a surfaceactive agent. For example, the composition may contain at least two 30 carriers, at least one of which is a surface-active agent.

A surface-active agent may be an emulsifying agent, a dispersing agent or a wetting agent; it may be nonionic or ionic. Examples of suitable surface-active agents WO 98/19542 PCT/US97/18199 include the sodium or calcium salts ofpolyacrylic acids and lignin sufonic acids; the condensation of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitol, sucrose or pentaerythritol; condensates of these with ethylene oxide and/or propylene oxide; condensates of these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohol or alkyl phenols, for example p-octylphenol or p-octylcresol, with ethylene oxide and/or propylene oxide; sulfates or sulfonates of these condensation products; alkali or alkaline earth metal salts, preferably sodium salts, or sulfuric or sulfonic acid esters containing at least carbon atoms in the molecule, for example sodium lauryl sulphate, sodium secondary alkyl sulfates, sodium salts of sulfinated castor oil, and sodium alkylaryl sulfonates such as dodecylbenzene sulfonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.

Pesticidal compositions may for example be formulated as wettable powders, dusts, granules, baits, solutions, emulsifiable concentrates, emulsions, suspension concentrates and aerosols.

Wettable powders usually contain 25, 50 or 75% weight of active ingredient and .usually contain in addition to solid inert carrier, 3-10% weight of a dispersing agent and, where necessary, 0-10% weight of stabilizer(s) and/or other additives such as penetrants or stickers.

i Dusts are usually formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant, and are diluted in the field with further solid carrier to give a composition usually containing 0.5-10% weight of active ingredient.

25 Granules are usually prepared to have a size between 10 and 100 BS mesh (1.676- 0.152 mm), and may be manufactured by, for example, agglomeration or impregnation techniques. Generally, granules will contain 0.01-75% weight active ingredient and 0-10% weight of additives such as stabilizers, surfactants, slow release modifiers and binding agents. The so-called "dry flowable powders" consist of relatively small granules having a relatively high concentration of active ingredient. Of particular interest in current practice are the water dispersible granular formulations. These are in the form of dry, hard granules that are essentially WO 98/19542 WO 8/1542PCTIUS97/18199 dust-free, and are resistant to attrition on handling, thus minimizing the formation of dust. On contact with water, the granules readily disintegrate to form stable suspensions of the particles of active material. Such formulation contain 90% or more by weight of finely divided active material, 3-7% by weight of a blend of surfactants, which act as wetting dispersing, suspending and binding agents, and 1 3% by weight of a finely divided carrier, which acts as a resuspending agent.

Baits are prepared by, for example, combining a mixture of a suitable food source, such as sawdust for termites or grain or meal for cockroaches, with an amount of active ingredient sufficient to provide the desired result; for example, from about 0.001% to about 20% weight active ingredient and forming the mixture into a paste by the addition of about 1% to 5% of a water based binder such as agar. The paste-like mixture may be applied as is or may be packed into a housing such as a hollowed out wooden dowel or a plastic tube or bait station. In other embodiments, sheets of paper or cardboard can be sprayed with or dipped in a diluted formulation containing the active ingredient. Baits are a preferable embodiment of the present invention.

Emulsifiable concentrates usually contain, in addition to a solvent and, when necessary, co-solvent, 10-50% weight per volume active ingredient, 2-20% weight per volume emulsifiers and 0-20% weight per volume of other additives such as stabilizers, penetrants and corrosion inhibitors.

Suspension concentrates are usually compounded so as to obtain a stable, non-sedimenting fiowable product and usually contain 10-75% weight active ingredient, 0.5-15% weight of dispersing agents, 0.1-10% weight of suspending.

agents such as protective colloids and thixotropic agents, 0-10% weight of other additives such as defoamers, corrosion inhibitors, stabilizers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially insoluble; certain organic solids or inorganic salts may be present dissolved in the formulation to assist in preventing sedimentation or as anti-freeze agents for water.

Aqueous dispersions and emulsions are compositions which may be obtained by diluting a wettable powder or a concentrate with water. The said emulsions may be of the water-in-oil or of the oil-in-water type, and may have a thick 'mayonnaise'-like consistency.

WO 98/19542 PCT/US97/18199 The method of applying a compound of Formula to combat termites comprises applying the compound, conveniently in a composition comprising the compound of Formula and a carrier as described above, to a locus or area to be treated for the termites, such as soil or timber, already subject to infestation or attack by termites or intended to be protected from infestation by termites. The active ingredient is, of course, applied in an amount sufficient to effect the desired action of combatting termite infestation. This dosage is dependent upon many factors, including the carrier employed, the method and conditions of the application, whether the formulation is present at the locus in the form of a film, or as discrete particles or as a bait, the thickness of film or size of particles, the degree of termite infestation, and the like.

Proper consideration and resolution of these factors to provide the necessary dosage of the active ingredient at the locus to be protected are within the skill of those versed in the art. In general, however, the effective dosage of the compound of the invention at the locus to be protected--i.e., the dosage to which the termite has access-is of the order of 0.001 to 1.0% based on the total weight of the composition, though under some circumstances the effective concentration may be as little as 0.0001% or as much as on the same basis.

When used to control cockroaches, it is preferred to use the active ingredient in a 20 treated bait or as a surface treatment.

.°oo.i When used to control ants, it is preferred to use the active ingredient in a liquid bait or granular bait.

25 When used to control termites, it is preferred to use the active ingredient in a cellulose based bait.

When used to control fleas, it is preferred to use the active ingredient on a treated substrate.

WO 98/19542 PCTIUS97/18199 *Suitable formulations include granular, paste, or dust cockroach bait, SP or MP cockroach and/or flea sprayables, cellulose-based termite baits, liquid or granular ant baits, feed-through or topical animal treatment for fleas.

&feet S S. S .s* 9 S. S

*S

5 S. S S S S 55

Claims (6)

1. A compound of the formula (II) F F CI O O 11 II -N-C-N OCF 2 CHFCF 3 I V I2 R R F CI (I) wherein R 1 and R 2 are H, methyl, or ethyl, provided that at least one of R 1 and R 2 is methyl or ethyl.

2. A pesticide composition which comprises an effective amount of a compound of claim 1 in combination with a carrier.

3. A cockroach bait comprising a compound of claim 1 in a conventional bait.

4. An ant bait comprising a compound of claim 1 in combination with a 15 conventional bait.

A termite bait comprising a compound of claim 1 in combination with a conventional bait.

6. A compound according to claim 1 substantially as hereinbefore described with reference to any of the examples. DATED: 21 November, 2000 S. S *0 0 0e S OSO S 09 0@SS S S. S SO S 0@ S. PHILLIPS ORMONDE FITZPATRICK Attorneys for: DOW AGROSCIENCES LLC oprhaa;~J3ild W:\lionaSpecis\div of 49797.doc