PESTICIDAL COMPOUNDS AND THEIR USES

Abstract

The present invention concerns certain cyclic derivatives of guanidine compounds and their use in protecting plants, their use to control mosquitoes, and vector control management methods or control solutions comprising such a cyclic derivative of guanidine compounds, in particular the invention relates to a substrate, to a composition, comprising a cyclic derivative of guanidine compounds for controlling mosquitoes.

Claims

1. The use of one or more compounds of formula (I), for controlling mosquitoes ##STR00097## wherein A represents O or CH.sub.2; R1 is aryl; optionally substituted aryl; heteroaryl; optionally substituted heteroaryl; or cyclo-propyl; R2 is C1-C6-alkyl; optionally substituted C1-C6-alkyl; C2-C6-alkenyl; optionally substituted C2-C6-alkenyl; C3-C8-cycloalkyl; C1-C4-alkyl, C1-C4-haloalkyl, halogen or CN substituted C3-C8-cycloalkyl; C3-C8-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; optionally substituted C3-C8-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; aryl; optionally substituted aryl; arylalkyl; arylalkyl wherein the aryl is substituted by one to three substituents independently selected from C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, halogen and CN; C4-C8-cycloalkylalkyl; or C1-C4-alkyl, C1-C4-haloalkyl, halogen or CN substituted C4-C8-cycloalkylalkyl; R3 is C1-C8-alkyl; C1-C8-haloalkyl; C2-C8-alkenyl; C2-C8-alkynyl; C2-C8-haloalkenyl; C3-C10-cycloalkyl; C3-C10-halocycloalkyl; C3-C8-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; optionally substituted C3-C8-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; aryl; or haloaryl; R4 is H; C1-C6-alkyl; halogen or CN substituted C1-C6-alkyl; C2-C6-alkenyl; or C1-C6-alkoxy; R5 is H; C1-C6-alkyl; halogen or CN substituted C1-C6-alkyl; C2-C6-alkenyl; C1-C4-alkyl, C1-C4-haloalkyl, halogen or CN substituted C2-C6-alkenyl; C2-C6-alkynyl; or C1-C4-alkyl, C1-C4-haloalkyl, halogen or CN substituted C2-C6-alkynyl; or an agrochemically acceptable salt or N-oxide thereof.

2. The use according to claim 1 wherein A is O, R.sup.1 is aryl; aryl substituted by 1 to 3 substituents independently selected from C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-haloalkyl, halogen and CN; heteroaryl containing 1 to 3 heteroatoms independently selected from nitrogen, oxygen and sulfur; heteroaryl thereof substituted by 1 to 3 substituents independently selected from C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkyl, halogen and CN; or cyclo-propyl; R.sup.2 is C.sub.1-C.sub.6-alkyl; halogen or CN substituted C.sub.1-C.sub.6-alkyl; C.sub.2-C.sub.6-alkenyl; C.sub.1-C.sub.4-haloalkyl, halogen or CN substituted C.sub.2-C.sub.6-alkenyl; C.sub.3-C.sub.5-cycloalkyl; C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, halogen or CN substituted C.sub.3-C.sub.5-cycloalkyl; C.sub.3-C.sub.5-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, halogen or CN substituted C.sub.3-C.sub.5-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; aryl; aryl substituted by 1 to 3 substituents independently selected from C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkyl, halogen and CN; arylalkyl; arylalkyl wherein the aryl is substituted by one to three substituents independently selected from C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkyl, halogen and CN; C.sub.4-C.sub.8-cycloalkylalkyl; or C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, halogen or CN substituted C.sub.4-C.sub.8-cycloalkylalkyl; R.sup.3 is a branched C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.5-alkynyl; C.sub.3-C.sub.10-cycloalkyl; C.sub.3-C.sub.10-halocycloalkyl; C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, halogen or CN substituted C.sub.3-C.sub.5-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; aryl; or haloaryl; R.sup.4 is C.sub.1-C.sub.6-alkyl; halogen or CN substituted C.sub.1-C.sub.6-alkyl; or C.sub.2-C.sub.6-alkenyl; and R.sup.5 is H; C.sub.1-C.sub.6-alkyl; halogen or CN substituted C.sub.1-C.sub.6-alkyl; C.sub.2-C.sub.6-alkenyl; C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, halogen or CN substituted C.sub.2-C.sub.6-alkenyl; C.sub.2-C.sub.6-alkynyl; C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, halogen or CN substituted C.sub.2-C.sub.6-alkynyl; aryl; or C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, halogen or CN substituted aryl.

3. An integrated mosquito vector control management method or a vector control solution comprising one or more compounds as defined in claim 1.

4. The vector control solution according to claim 3, wherein the solution is a net incorporated with the one or more compounds.

5. The vector control solution according to claim 3, wherein the solution is a composition for coating a net, which composition comprises the one or more compounds.

6. The vector control solution according to claim 3, wherein the solution is a composition for spraying surfaces of a dwelling, which composition comprises the one or more compounds.

7. A compound of formula (I-A1), ##STR00098## wherein R.sup.1 is aryl; optionally substituted aryl; heteroaryl; optionally substituted heteroaryl; or cyclo-propyl; R.sup.2 is C1-C6-alkyl; optionally substituted C1-C6-alkyl; C2-C6-alkenyl; optionally substituted C2-C6-alkenyl; C3-C8-cycloalkyl; C1-C4-alkyl, C1-C4-haloalkyl, halogen or CN substituted C3-C8-cycloalkyl; C3-C8-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; optionally substituted C3-C8-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; aryl; optionally substituted aryl; arylalkyl arylalkyl wherein the aryl is substituted by one to three substituents independently selected from C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, halogen and CN; C4-C8-cycloalkylalkyl; or C1-C4-alkyl, C1-C4-haloalkyl, halogen or CN substituted C4-C8-cycloalkylalkyl; R.sup.4 is H; C1-C6-alkyl; halogen or CN substituted C1-C6-alkyl; C2-C6-alkenyl; or C1-C6-alkoxy; R.sup.5 is H; C1-C6-alkyl; halogen or CN substituted C1-C6-alkyl; C2-C6-alkenyl; C1-C4-alkyl, C1-C4-haloalkyl, halogen or CN substituted C2-C6-alkenyl; C2-C6-alkynyl; or C1-C4-alkyl, C1-C4-haloalkyl, halogen or CN substituted C2-C6-alkynyl; and R.sup.3 is selected from n-C.sub.1-C.sub.8-alkyl, C.sub.3-C.sub.5-fluoroalkyl, C.sub.2-C.sub.5-alkenyl, C.sub.2-C.sub.5-alkynyl, C.sub.2-C.sub.8-haloalkenyl, C.sub.3-C.sub.10-cycloalkyl, C.sub.3-C.sub.10-halocycloalkyl, C.sub.3-C.sub.10-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom, phenyl, and halophenyl; or R.sup.3 is C1-C8-alkyl; C1-C8-haloalkyl; C2-C8-alkenyl; C2-C8-alkynyl; C2-C8-haloalkenyl; C3-C10-cycloalkyl; C3-C10-halocycloalkyl; C3-C8-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; optionally substituted C3-C8-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; aryl; or haloaryl.

8. The compound of claim 7, wherein R.sup.3 is either C(C.sub.2H.sub.5).sub.3, or C(CH.sub.3).sub.2CH.sub.2C(CH.sub.3).sub.3.

9. The compound of claim 7, wherein R.sup.1 is substituted aryl, heteroaryl; optionally substituted heteroaryl; or cycclopropyl; and R.sup.3 is selected from CH(CH.sub.3).sub.2, C(CH.sub.3).sub.2(C.sub.2H.sub.5), C(CH.sub.3)(C.sub.2H.sub.5).sub.2, 1-methyl-cyclopropyl and CH.sub.2CF.sub.3.

10. The compound of claim 7, wherein R.sup.2 is selected from 3-methyl-oxetan-3-yl, CH.sub.2CF.sub.3 and n-pentyl.

11. The compound of claim 7, wherein R.sup.1 is substituted aryl; heteroaryl; optionally substituted heteroaryl; or cyclo-propyl and R.sup.2 is methyl, ethyl, n-propyl, n-hexyl, phenylethyl, and CF.sub.3.

12. The compound of claim 7, wherein R.sup.2 is selected from 3-methyl-oxetan-3-yl, CH.sub.2CF.sub.3, n-pentyl, methyl, ethyl, n-propyl, n-hexyl, phenylethyl, and CF.sub.3.

13. The compound of claim 7, wherein R.sup.1 is substituted aryl, heteroaryl, optionally substituted heteroaryl and (i) R.sup.2 is n-butyl with the proviso that the substituent on the aryl of R.sup.1 is not 4-chloro or not 4-OCF.sub.3; or (ii) R.sup.2 is cyclo-pentyl with the proviso that the substituent on the aryl of R.sup.1 is not 4-chloro.

14. The compound of claim 7, wherein R.sup.1 is substituted aryl, heteroaryl, or optionally substituted heteroaryl and R.sup.2 is C.sub.3-C.sub.8-cycloalkyl with the proviso that the substituent on the aryl of R.sup.1 is 2-fluoro.

15. The compound of claim 7, wherein R.sup.2 is cyclo-propylmethyl with the proviso that the substituent on the aryl of R.sup.1 is not 4-chloro.

16. A compound of formula (I-2), ##STR00099## wherein R.sup.1 is aryl; optionally substituted aryl; heteroaryl; optionally substituted heteroaryl; or cyclo-propyl; R.sup.3 is C1-C8-alkyl; C1-C8-haloalkyl; C2-C8-alkenyl; C2-C8-alkynyl; C2-C8-haloalkenyl; C3-C10-cycloalkyl; C3-C10-halocycloalkyl; C3-C8-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; optionally substituted C3-C8-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; aryl; or haloaryl; R.sup.4 is H; C1-C6-alkyl; halogen or CN substituted C1-C6-alkyl; C2-C6-alkenyl; or C1-C6-alkoxy; R.sup.5 is H; C1-C6-alkyl; halogen or CN substituted C1-C6-alkyl; C2-C6-alkenyl; C1-C4-alkyl, C1-C4-haloalkyl, halogen or CN substituted C2-C6-alkenyl; C2-C6-alkynyl; or C1-C4-alkyl, C1-C4-haloalkyl, halogen or CN substituted C2-C6-alkynyl; and R2 is C1-C6-alkyl; halogen or CN substituted C1-C6-alkyl; C2-C6-alkenyl; optionally substituted C2-C6-alkenyl; C3-C8-cycloalkyl; C1-C4-alkyl, C1-C4-haloalkyl, halogen or CN substituted C3-C8-cycloalkyl; C3-C8-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; optionally substituted C3-C8-cycloalkyl in which the cycloalkyl ring contains 1 oxygen heteroatom; aryl; optionally substituted aryl; arylalkyl; arylalkyl wherein the aryl is substituted by one to three substituents independently selected from C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, halogen and CN; C4-C8-cycloalkylalkyl; or C1-C4-alkyl, C1-C4-haloalkyl, halogen or CN substituted C4-C8-cycloalkylalkyl.

17. A pesticidal composition comprising a compound defined in claim 7, one or more formulation additives and a carrier.

18. A combination of active ingredients comprising a compound defined in claim 7, and one or more further active ingredients.

19. A method of controlling insects, acarines, nematodes or molluscs which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of the compound or a composition containing the compound defined in claim 7, to a pest, a locus of pest, a plant, to a plant susceptible to attack by a pest or to plant propagation material thereof, such as a seed, provided if the control were on a human or animal body, then it is non-therapeutical.

20. A plant propagation material comprising by way of treatment or coating one or more compounds defined in claim 1, optionally also comprising a colour pigment.

Description

PREPARATION EXAMPLES

Example P1: N-tert-Butyl-5-cyclopropyl-2-methyl-5-phenyl-1,2,4-oxadiazol-3-amine (compound P1.17)

Step 1: 1-tert-Butyl-3-[cyclopropyl(phenyl)methyl]thiourea

[0434] ##STR00034##

[0435] Cyclopropyl(phenyl)methanamine (2.00 g) and triethylamine (1.53 g, 2.10 ml) were dissolved in THF (100 ml) and stirred under Argon. tert-Butyl isothiocyanate (3.16 g, 3.48 ml) was slowly added and the reaction mixture was stirred at 66 C. for 18 hours. The reaction mixture was concentrated and the residue was purified by Combiflash with cyclohexane/ethylacetate (0-20%). 3.34 g of 1-tert-butyl-3-[cyclopropyl(phenyl)methyl]thiourea were obtained as a pale beige solid; m.p. 104-107 C. .sup.1H-NMR [ppm] in CDCl.sub.3: 0.38-0.51 (m, 2H), 0.55-0.68 (m, 2H), 1.13-1.26 (m, 1H), 1.32 (s, 9H), 4.32 (bs, 1H), 5.58 (bs, 1H), 6.26 (bs, 1H); 7.27-7.40 (m, 5H).

Step 2: N-tert-Butyl-N-[cyclopropyl(phenyl)methyl]methanediimine

[0436] ##STR00035##

[0437] 1-tert-Butyl-3-[cyclopropyl(phenyl)methyl]thiourea (2.00 g), bis(2-pyridyloxy)methanethione (1.83 g) were dissolved in acetonitrile (80 ml) and 4-N,N-dimethylamino-pyridine (DMAP, 931 mg) was added. The reaction mixture was stirred under argon at 80 C. for 14 hours (orange solution). The reaction mixture was concentrated. The residue was purified by Combiflash with cyclohexane/ethylacetate. 326 mg of N-tert-butyl-N-[cyclopropyl(phenyl)methyl]methanediimine were isolated as a colourless liquid. .sup.1H-NMR [ppm] in CDCl.sub.3: 0.33-0.41 (m, 1H), 0.49-0.58 (m, 2H), 0.64-0.72 (m, 1H), 1.20 (s, 9H), 1.24-1.32 (m, 1H), 3.81 (d, 1H), 7.22-7.40 (m, 5H).

Step 3: 3-tert-Butyl-2-[cyclopropyl(phenyl)methyl]-1-hydroxy-1-methyl-guanidine hydrochloride

[0438] ##STR00036##

[0439] N-tert-Butyl-N-[cyclopropyl(phenyl)methyl]methanediimine (600 mg) and pyridine (252 mg, 0.258 ml) were dissolved in ethanol (30 ml) and stirred under argon. N-methylhydroxylamine hydrochloride (285 mg) was slowly added and the reaction mixture was stirred at 80 C. for 16 hours. The reaction mixture was concentrated. The residue was purified by Combiflash using dichloromethane/MeOH (0 to 10%) as eluents. 741 mg of 3-tert-butyl-2-[cyclopropyl-(phenyl)methyl]-1-hydroxy-1-methyl-guanidine hydrochloride were obtained as a colourless sticky solid.

Step 4: N-tert-Butyl-5-cyclopropyl-2-methyl-5-phenyl-1,2,4-oxadiazol-3-amine (compound P1.17)

[0440] ##STR00037##

[0441] 3-tert-Butyl-2-[cyclopropyl(phenyl)methyl]-1-hydroxy-1-methyl-guanidine hydrochloride (628 mg) was dissolved in dichloromethane (20 ml) and stirred at room temperature under Argon. Manganese dioxide (389 mg) was slowly added and the reaction mixture was stirred at room temperature for 17 hours. The reaction mixture was filtered on Celite and washed with dichloromethane. The filtrate was concentrated. The residue was purified by Combiflash with cyclohexane/ethylacetate (0 to 15%). 419 mg of N-tert-butyl-5-cyclopropyl-2-methyl-5-phenyl-1,2,4-oxadiazol-3-amine were isolated as a colourless sticky solid; m.p. 76-78 C. .sup.1H-NMR [ppm] in CDCl.sub.3: 0.40-0.59 (m, 3H), 0.60-0.67 (m, 1H), 1.34-1.43 (m, 1H), 1.38 (s, 9H), 2.83 (s, 3H), 3.51 (bs, 1H), 7.20-7.27 (m, 1H), 7.28-7.33 (m, 2H), 7.55-7.60 (m, 2H).

Example P2: N-tert-Butyl-5-cyclopropyl-N,2-dimethyl-5-phenyl-1,2,4-oxadiazol-3-amine (compound P1.18)

[0442] ##STR00038##

[0443] To a suspension of sodium hydride (44 mg) in N,N-dimethylformamide (4 ml) was added N-tert-butyl-5-cyclopropyl-2-methyl-5-phenyl-1,2,4-oxadiazol-3-amine (100 mg) in DMF (0.5 ml). The reaction mixture was stirred at room temperature under argon and iodomethane (156 mg, 0.0686 ml) in DMF (0.5 ml) was added dropwise. The reaction mixture was stirred at room temperature for 4.5 hours. The reaction mixture was poured into cold water (25 ml) and extracted with ethylacetate (2 times). The combined organic phases were washed with water, dried with Na.sub.2SO.sub.4, filtered and concentrated. The residue was purified by Combiflash with cyclohexane/ethylacetate (0 to 10%). 87 mg of N-tert-butyl-5-cyclopropyl-N,2-dimethyl-5-phenyl-1,2,4-oxadiazol-3-amine were isolated as a pale yellow sticky solid. .sup.1H-NMR [ppm] in CDCl.sub.3: 0.41-0.55 (m, 3H), 0.56-0.62 (m, 1H), 1.32-1.40 (m, 1H), 1.39 (s, 9H), 2.77 (s, 3H), 2.79 (s, 3H), 7.20-7.27 (m, 1H), 7.28-7.33 (m, 2H), 7.53-7.59 (m, 2H).

Example P3: 5-Cyclopropyl-5-(4-fluorophenyl)-2-methyl-N-(2,2,2-trifluoro-1,1-dimethyl-ethyl)-1,2,4-oxadiazol-3-amine (compound P1.88)

Step 1: 1-[cyclopropyl-(4-fluorophenyl)methyl]-3-(2,2,2-trifluoro-1,1-dimethyl-ethyl)thiourea

[0444] ##STR00039##

[0445] To a stirred solution of cyclopropyl-(4-fluorophenyl)methanamine (5.00 g) in chloroform (25 ml) was added triethylamine (10.5 ml) followed by the addition of thiophosgene (2.44 g) at 0 C. After the addition the temperature of the reaction mixture was slowly raised to room temperature and stirring was continued for 2 hours. Then 1,1,1-trifluoro-2-methyl-propan-2-amine (3.5 ml) was added at room temperature and stirring was continued for 24 hours. The reaction mixture was purified directly by silica-gel column chromatography using ethyl acetate/hexane as an eluent to give 1.5 g of 1-[cyclopropyl-(4-fluorophenyl)methyl]-3-(2,2,2-trifluoro-1,1-dimethyl-ethyl)thiourea. .sup.1H-NMR [ppm] in CDCl.sub.3: 0.36-0.48 (m, 2H), 0.55-0.68 (m, 2H), 1.10-1.21 (m, 1H), 1.58 (s, 3H), 1.65 (s, 1H); 4.49 (bs, 1H), 5.72 (bs, 1H), 6.54 (bs, 1H), 7.01-7.08 (m, 2H), 7.28-7.37 (m, 2H).

Step 2: N-[Cyclopropyl-(4-fluorophenyl)methyl]-N-(2,2,2-trifluoro-1,1-dimethyl-ethyl)methane-diimine

[0446] ##STR00040##

[0447] To a stirred solution of 1-[cyclopropyl-(4-fluorophenyl)methyl]-3-(2,2,2-trifluoro-1,1-dimethyl-ethyl)thiourea (8.3 g) in dichloromethane (90 ml) at 0 C. were added triethylamine (15.1 ml) and 2-chloro-1,3-dimethyl-4,5-dihydroimidazol-1-ium chloride (6.87 g). After addition the temperature of the reaction mixture was slowly raised to room temperature and stirring was continued for 2 hours. After completion of the reaction the mixture was concentrated under reduce pressure. The residue was purified by silica gel column chromatography using 3% ethyl acetate-hexane as an eluent to give 3.87 g of N-[cyclopropyl-(4-fluorophenyl)methyl]-N-(2,2,2-trifluoro-1,1-dimethyl-ethyl)methane-diimine as a colorless liquid. .sup.1H-NMR [ppm] in CDCl.sub.3: 0.31-0.42 (m, 1H), 0.46-0.62 (m, 2H), 0.65-0.76 (m, 1H), 1.19-1.29 (m, 1H), 1.37 (s, 6H), 3.87 (d, 1H), 7.96-7.08 (m, 2H), 7.28-7.40 (m, 2H).

Step 3: [[[Cyclopropyl-(4-fluorophenyl)methyl]amino]-[(2,2,2-trifluoro-1,1-dimethyl-ethyl)amino]-methylene]-hydroxy-methyl-ammonium chloride

[0448] ##STR00041##

[0449] To a stirred solution of N-[cyclopropyl-(4-fluorophenyl)methyl]-N-(2,2,2-trifluoro-1,1-dimethyl-ethyl)methane-diimine (0.8 g) in ethanol (8 ml) was added at room temperature N-methylhydroxylamine hydrochloride (0.29 g) and stirring was continued for 16 hours. After completion of the reaction the reaction mixture was concentrated under reduce pressure to give 830 mg of crude material of [[[cyclopropyl-(4-fluorophenyl)methyl]amino]-[(2,2,2-trifluoro-1,1-dimethyl-ethyl)amino]-methylene]-hydroxy-methyl-ammonium chloride. The crude material was used for the next step without further purification.

Step 4: 5-Cyclopropyl-5-(4-fluorophenyl)-2-methyl-N-(2,2,2-trifluoro-1,1-dimethyl-ethyl)-1,2,4-oxadiazol-3-amine (compound P1.88)

[0450] ##STR00042##

[0451] To a stirred solution of crude material of [[[cyclopropyl-(4-fluorophenyl)methyl]amino]-[(2,2,2-trifluoro-1,1-dimethyl-ethyl)amino]-methylene]-hydroxy-methyl-ammonium chloride (2.4 g) in THF (25 ml) was added MnO.sub.2 (3.18 g) at room temperature and stirring was continued for 4 h. After completion of the reaction the reaction mixture was passed through a celite-bed and the collected solvent was concentrated under reduced pressure to give the crude compound. The crude compound was purified by silica gel column chromatography using hexane-ethyl acetate (2-20%) as an eluent to give 41 mg of 5-cyclopropyl-5-(4-fluorophenyl)-2-methyl-N-(2,2,2-trifluoro-1,1-dimethyl-ethyl)-1,2,4-oxadiazol-3-amine as an off-white solid; 76-78 C. .sup.1H-NMR [ppm] in CDCl.sub.3: 0.42-0.61 (m, 4H), 1.29-1.38 (m, 1H), 1.62 (s, 3H), 1.63 (s, 3H), 2.86 (s, 3H), 3.74 (bs, 1H), 7.95-7.05 (m, 2H), 7.44-7.55 (m, 2H).

Example P4: N-tert-Butyl-5-ethyl-2-methyl-5-phenyl-1,2,4-oxadiazol-3-amine (compound P1.94)

Step 1: 1-Phenylpropylidenecyanamide

[0452] ##STR00043##

[0453] To a stirring solution of 1-phenylpropan-1-one (4 g) in dichloromethane (30 ml) was added TiCl.sub.4 (1M in dichloromethane, 74.5 ml) at 0 C. After addition the temperature of the reaction mixture was slowly raised to room temperature and stirring was continued for 1 hour. The reaction mixture was cooled again and a solution of N,N-bis(trimethylsilyl)methanediimine (12.2 g) in dichloromethane was added. Then the temperature of the reaction was slowly raised to room temperature and stirring was continued for 1 hour. After completion of the reaction the mixture was quenched with water and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to give 4.5 g of crude material of 1-phenylpropylidenecyanamide. This material was used for the next step without further purification.

Step 2: 5-Ethyl-2-methyl-5-phenyl-1,2,4-oxadiazol-3-amine

[0454] ##STR00044##

[0455] To a stirred solution of crude 1-phenylpropylidenecyanamide (950 mg) in dry THF (8 ml) were added triethylamine (1.76 ml) and molecular sieves. The reaction mixture was stirred for 30 minutes at room temperature. Then a solution of hydroxylamine hydrochloride (2 g) in THF was added to the reaction mixture at room temperature and stirring was continued for 1 hour. The solid was filtered off and the solvent was evaporated to dryness. A sticky mass was obtained which was triturated with pentane. The solvent was decanted and the process was repeated twice. The combined solid was dried under vacuum to give 1.9 g of 5-ethyl-2-methyl-5-phenyl-1,2,4-oxadiazol-3-amine. .sup.1H-NMR [ppm] in d.sub.6-DMSO: 0.77 (t, 3H), 1.71-1.83 (m, 2H), 2.85 (s, 3H), 3.32 (bs, 1H), 6.05 (s, 2H), 7.21 (t, 1H), 7.29 (t, 2H), 7.40 (d, 2H).

Step 3: N-tert-butyl-5-ethyl-2-methyl-5-phenyl-1,2,4-oxadiazol-3-amine (compound P1.94)

[0456] ##STR00045##

[0457] To a stirred solution of 5-ethyl-2-methyl-5-phenyl-1,2,4-oxadiazol-3-amine (250 mg) and tert-butyl 2,2,2-trichloroethanimidate (0.87 ml) in THF:n-hexane (1:1, 3 ml) was added BF.sub.3-Et.sub.2O at 0 C. After addition the temperature of the reaction was slowly raised to room temperature and stirring was continued for 16 hours. The reaction was quenched with saturated aqueous NaHCO.sub.3-solution and extracted with ethyl acetate (3 times). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using hexane-ethyl acetate (20%) to give 23 mg of N-tert-butyl-5-ethyl-2-methyl-5-phenyl-1,2,4-oxadiazol-3-amine as a solid; 48-50 C. .sup.1H-NMR [ppm] in CDCl.sub.3: 0.90 (t, 3H), 1.42 (s, 9H), 1.93 (q, 2H), 2.80 (s, 3H), 3.49 (bs, 1H), 7.12-7.32 (m, 3H), 7.44-7.55 (m, 2H).

Example P5: N-tert-Butyl-5,5-bis(4-fluorophenyl)-3-methyl-4H-imidazol-2-amine (compound P2.1)

Step 1: 5,5-Bis(4-fluorophenyl)-3-methyl-2-thioxo-imidazolidin-4-one

[0458] ##STR00046##

[0459] 1,2-Bis(4-fluorophenyl)ethane-1,2-dione (2.00 g) and methylthiourea (3.30 g) were dissolved in ethanol (40 ml) and 1,4-dioxane (40 mL). The reaction mixture was stirred at room temperature and sodium carbonate (3.87 g) in water (20 ml) was added dropwise. The reaction mixture was then stirred at 85 C. for 5 hours. Then the reaction mixture was concentrated and diluted with ethylacetate (100 ml) and washed with brine (20 ml). The organic phase was washed with brine, dried with magnesium sulfate, filtered and concentrated. The residue was purified by Combiflash with cyclohexane/ethylacetate (0 to 20%) to give 2.38 g of 5,5-bis(4-fluorophenyl)-3-methyl-2-thioxo-imidazolidin-4-one as a solid; m.p. 161-163 C. .sup.1H-NMR [ppm] in CDCl.sub.3: 3.30 (s, 3H), 7.01-7.09 (m, 4H), 7.25-7.32 (m, 4H), 8.56 (bs, 1H).

Step 2: 5,5-Bis(4-fluorophenyl)-3-methyl-2-methylsulfanyl-imidazol-4-one

[0460] ##STR00047##

[0461] 5,5-Bis(4-fluorophenyl)-3-methyl-2-thioxo-imidazolidin-4-one (400 mg) was dissolved in acetonitrile (13 ml). Potassium carbonate (194 mg) was added and the reaction mixture was stirred at room temperature. Iodomethane (268 mg, 0.117 m) was then added dropwise under argon. The reaction mixture was then stirred at 60 C. for 20 hours. The reaction mixture was concentrated then suspended in dichloromethane. The insoluble salt was filtered off and the filtrate was concentrated. 277 mg of 5,5-bis(4-fluorophenyl)-3-methyl-2-methylsulfanyl-imidazol-4-one were obtained as a solid; m.p. 135-137 C. .sup.1H-NMR [ppm] in CDCl.sub.3: 2.68 (s, 3H), 3.08 (s, 3H), 6.94-7.02 (m, 4H), 7.46-7.55 (m, 4H).

Step 3: 2-(tert-Butylamino)-5,5-bis(4-fluorophenyl)-3-methyl-imidazol-4-one

[0462] ##STR00048##

[0463] 5,5-Bis(4-fluorophenyl)-3-methyl-2-methylsulfanyl-imidazol-4-one (989 mg) was dissolved in dichloromethane (30 ml) and cooled down to 0 C. Sulfuryl chloride (1.406 g) was slowly added and the reaction mixture was stirred at room temperature for 19 hours. The reaction mixture was concentrated. tert-Butylamine (6.25 ml), silver nitrate (505 mg) and sodium carbonate (473 mg) were was added to the residue. The reaction mixture was stirred under microwave conditions at 135 C. for 5 hours. The reaction mixture was concentrated, dissolved in tert-butyl methyl ether, and then filtrated trough Celite. The filtrate was concentrated and purified by Combiflash with cyclohexane/EtOAc as eluents (0 to 20%). The fractions containing the desired product were concentrated and further purified by reversed phase preparative HPLC to give 234 mg of 2-(tert-butylamino)-5,5-bis(4-fluorophenyl)-3-methyl-imidazol-4-one as a solid; m.p. 149-150 C. .sup.1H-NMR [ppm] in CDCl.sub.3: 1.56 (s, 9H), 2.98 (s, 3H), 3.84 (bs, 1H), 6.91-6.98 (m, 4H), 7.58-7.67 (m, 4H).

Step 4: N-tert-Butyl-5,5-bis(4-fluorophenyl)-3-methyl-4H-imidazol-2-amine (compound P2.1)

[0464] ##STR00049##

[0465] To a suspension of lithium aluminium hydride (16 mg) in diethylether (0.42 ml) was added a solution of trichloroalumane (56 mg) in diethylether (0.42 ml). The mixture was stirred at room temperature and 2-(tert-butylamino)-5,5-bis(4-fluorophenyl)-3-methyl-imidazol-4-one (50 mg) in diethylether (0.42 ml) and THF (0.46 ml) was slowly added. After 3 hours the reaction was stopped. A saturated solution of sodium carbonate was added and the inorganic residue was filtered. The filtrate was washed with water and concentrated. The residue was purified by Combiflash with hexane/ethylacetate (0-60%) to give 48 mg of N-tert-butyl-5,5-bis(4-fluorophenyl)-3-methyl-4H-imidazol-2-amine as a solid; m.p. 99-102 C. .sup.1H-NMR [ppm] in CDCl.sub.3: 1.47 (s, 9H), 2.69 (s, 3H), 3.70 (s, 2H), 4.5-4.9 (bs, 1H) 6.90-6.99 (m, 4H), 7.40-7.46 (m, 2H).

Example P6: 4-[3-(tert-butylamino)-5-cyclopropyl-2-methyl-1,2,4-oxadiazol-5-yl]benzonitrile (compound P1.136)

[0466] ##STR00050##

[0467] 5-(4-bromophenyl)-N-tert-butyl-5-cyclopropyl-2-methyl-1,2,4-oxadiazol-3-amine (150 mg) which was prepared analogously as described above was dissolved in degassed N,N-dimethylformamide (2.73 ml). Dicyanozinc (55 mg) and tetrakis(triphenylphosphine)-palladium (49 mg) were added. The mixture was stirred at 100 C. for 17 hours. The solution was diluted with ethyl acetate and washed with water, dried and concentrated. The residue was purified by Combiflash with Cyclohexane/Ethylacetate (0 to 15%) to give 104 mg of 4-[3-(tert-butylamino)-5-cyclopropyl-2-methyl-1,2,4-oxadiazol-5-yl]benzonitrile as a gum. .sup.1H-NMR [ppm] in CDCl.sub.3: 0.44-0.56 (m, 3H), 0.60-0.66 (m, 1H), 1.28-1.33 (m, 1H), 1.38 (s, 9H), 2.85 (s, 3H), 3.56 (bs, 1H), 7.56-7.63 (m, 2H), 7.65-7.68 (m, 2H).

Example P7: N-tert-butyl-5-cyclopropyl-5-[4-(4-fluorophenyl)phenyl]-2-methyl-1,2,4-oxadiazol-3-amine (compound P1.137)

[0468] ##STR00051##

[0469] 5-(4-bromophenyl)-N-tert-butyl-5-cyclopropyl-2-methyl-1,2,4-oxadiazol-3-amine (160 mg) which was prepared analogously as described above was dissolved in 1,2-dimethoxyethane (2.82 ml). Then (4-fluorophenyl)boronic acid (66.7 mg), disodium carbonate (5.00 eq) in water and tetrakis (triphenylphosphine)-palladium (21.1 mg) were added. The mixture was stirred at 85 C. for 8 hours. The reaction mixture was poured into water and extracted with ethylacetate. The organic phases were washed with brine, dried and concentrated. The residue was purified by Combiflash with Cyclohexane/Ethylacetate (0 to 15%) to give 134 mg of N-tert-butyl-5-cyclopropyl-5-[4-(4-fluorophenyl)phenyl]-2-methyl-1,2,4-oxadiazol-3-amine as a gum. .sup.1H-NMR [ppm] in CDCl.sub.3: 0.45-0.58 (m, 3H), 0.62-0.68 (m, 1H), 1.39-1.48 (m, 1H), 1.41 (s, 9H), 2.87 (s, 3H), 3.57 (bs, 1H), 7.09 (t, 2H), 7.47-7.56 (m, 4H), 7.63 (d, 2H).

[0470] The compounds in Table P1 and P2 were prepared as described in the examples above or similar methodology.

TABLE-US-00004 TABLE P1 Compounds of formula (I-1) [00052] (I-1)

[0471] The compounds in Table P1 can be prepared as described in the examples above or similar methodology. The following abbreviations are used in the table below: Me=methyl, Et=ethyl, Pr=propyl, Bu=butyl, Ph=phenyl, Bn=benzyl, LQ=liquid, GM=gum.

TABLE-US-00005 Cmpd No. R1 R2 R3 R4 R5 Melting Point P1.1 4-FPh Ph t-Bu Me Me 85-87 C. P1.2 4-FPh 4-FPh t-Bu Me H 100-102 C. P1.3 4-ClPh c-Pr t-Bu Me H 72-73 C. P1.4 Ph Ph t-Bu Me H 131-132 C. P1.5 4-FPh Ph t-Bu Me H 112-114 C. P1.6 3-FPh Ph t-Bu Me Et LQ P1.7 4-FPh Ph t-Bu Me Et LQ P1.8 4-FPh Me t-Bu Me H 84-90 C. P1.9 3-ClPh c-Pr t-Bu Me H 63-66 C. P1.10 3-ClPh c-Pr t-Bu Me Me LQ P1.11 3-ClPh c-Pr t-Bu Me Et LQ P1.12 3-CF.sub.3Ph Ph t-Bu Me H 133-136 C. P1.13 4-FPh c-Pr t-Bu Me H 70-72 C. P1.14 4-MeOPh c-Pr t-Bu Me H LQ P1.15 4-FPh c-Pr t-Bu Me Me LQ P1.16 4-CF.sub.3Ph Ph t-Bu Me Et LQ P1.17 Ph c-Pr t-Bu Me H 76-78 C. P1.18 Ph c-Pr t-Bu Me Me LQ P1.19 Ph c-Pr t-Bu Me Et LQ P1.20 4-MeOPh c-Pr t-Bu Me Me LQ P1.21 4-MeOPh c-Pr t-Bu Me Et LQ P1.22 4-CF.sub.3OPh Ph t-Bu Me H LQ P1.23 4-CF.sub.3OPh Ph t-Bu Me Me LQ P1.24 4-CF.sub.3OPh Ph t-Bu Me Et LQ P1.25 4-FPh 4-FPh t-Bu Et Me 92-96 C. P1.26 [00053] Me t-Bu Me H LQ P1.27 [00054] Me t-Bu Me Me LQ P1.28 3-FPh c-Pr t-Bu Me H GM P1.29 4-CF.sub.3OPh c-Pr t-Bu Me H GM P1.30 3-FPh c-Pr t-Bu Me Me LQ P1.31 4-CF.sub.3OPh c-Pr t-Bu Me Me LQ P1.32 4-CF.sub.3Ph c-Pr t-Bu Me H GM P1.33 4-CF.sub.3Ph c-Pr t-Bu Me Me GM P1.34 3,4-Cl.sub.2Ph c-Pr t-Bu Me H 96-98 C. P1.35 3,4-F.sub.2Ph c-Pr t-Bu Me H 55-57 C. P1.36 3,5-Cl.sub.2Ph c-Pr t-Bu Me H 126-129 C. P1.37 3,4-Cl.sub.2Ph c-Pr t-Bu Me Me LQ P1.38 3,4-F.sub.2Ph c-Pr t-Bu Me Me LQ P1.39 3,5-Cl.sub.2Ph c-Pr t-Bu Me Me LQ P1.40 4-FPh H t-Bu Me H GM P1.41 [00055] Me t-Bu Me Me 58-60 C. P1.42 2-FPh c-Pr t-Bu Me H SO P1.43 4-t-BuPh c-Pr t-Bu Me H 110-112 C. P1.44 2-FPh c-Pr t-Bu Me Me 62-63 C. P1.45 4-t-BuPh c-Pr t-Bu Me Me GM P1.46 4-FPh i-Pr t-Bu Me H 98-100 C. P1.47 4-FPh PhCH.sub.2CH.sub.2 t-Bu Me H GM P1.48 4-FPh c-Pentyl t-Bu Me H 88-91 C. P1.49 [00056] c-Pr t-Bu Me Me LQ P1.50 3-CF.sub.3Ph Ph t-Bu Me H 95-96 C. P1.51 3-CF.sub.3Ph Ph t-Bu Me Me 92-93 C. P1.52 4-BrPh c-Pr t-Bu Me H GM P1.53 4-BrPh c-Pr t-Bu Me Me LQ P1.54 4-c-PrPh c-Pr t-Bu Me H LQ P1.55 3-CF.sub.3Ph c-Pr t-Bu Me H 51-52 C. P1.56 2-ClPh c-Pr t-Bu Me H 96-98 C. P1.57 3-CF.sub.3Ph c-Pr t-Bu Me Me GM P1.58 2-ClPh c-Pr t-Bu Me Me 68-70 C. P1.59 2,4-Cl.sub.2Ph c-Pr t-Bu Me H LQ P1.60 2,4-F.sub.2Ph c-Pr t-Bu Me H LQ P1.61 2,3-Cl.sub.2Ph c-Pr t-Bu Me H 96-98 C. P1.62 2,4-Cl.sub.2Ph c-Pr t-Bu Me Me LQ P1.63 2,4-F.sub.2Ph c-Pr t-Bu Me Me LQ P1.64 2,3-Cl.sub.2Ph c-Pr t-Bu Me Me GM P1.65 2,3-F.sub.2Ph c-Pr t-Bu Me H 78-80 C. P1.66 2,3-F.sub.2Ph c-Pr t-Bu Me Me GM P1.67 2,6-F.sub.2Ph c-Pr t-Bu Me H GM P1.68 [00057] c-Pr t-Bu Me Me 80-82 C. P1.69 [00058] c-Pr t-Bu Me Me LQ P1.70 4-FPh c-PrCH.sub.2 t-Bu Me H LQ P1.71 4-FPh c-PrCH.sub.2 t-Bu Me Et 112-114 C. P1.72 3-BrPh c-Pr t-Bu Me H 76-78 C. P1.73 3-CNPh c-Pr t-Bu Me H GM P1.74 3-c-PrPh c-Pr t-Bu Me H GM P1.75 3-BrPh c-Pr t-Bu Me Me GM P1.76 [00059] c-Pr t-Bu Me H 116-118 C. P1.77 4-FPh c-Pr [00060] Me H 40-42 C. P1.78 [00061] c-Pr t-Bu Me H 58-60 C. P1.79 4-FPh c-Pr [00062] Me Me 59-61 C. P1.80 4-FPh c-Pr CMe.sub.2Et Me H 42-44 C. P1.81 4-FPh c-Pr CMe.sub.2Et Me Me LQ P1.82 2,4,6-F.sub.3Ph c-Pr t-Bu Me H GM P1.83 [00063] c-Pr t-Bu Me Me GM P1.84 4-FPh c-Bu t-Bu Me H 70-72 C. P1.85 4-FPh c-Bu t-Bu Me Me 42-44 C. P1.86 Ph c-Bu t-Bu Me H GM P1.87 Ph c-Bu t-Bu Me Me GM P1.88 4-FPh c-Pr [00064] Me H 76-78 C. P1.89 4-FPh c-Pr [00065] Me Me LQ P1.90 4-FPh c-Pr [00066] Me H 88-90 C. P1.91 4-FPh c-Pr [00067] Me Me LQ P1.92 4-FPh c-Pr [00068] Me H LQ P1.93 4-FPh c-Pr [00069] Me Me 42-44 C. P1.94 Ph Et t-Bu Me H 48-50 C. P1.95 Ph Et t-Bu Me Me LQ P1.96 4-FPh c-Pr CF.sub.3CH.sub.2 Me H 80-84C. P1.97 4-FPh c-Pr CF.sub.3CH.sub.2 Me Me LQ P1.98 Ph n-Pr t-Bu Me H 62-64 C. P1.99 4-FPh Et t-Bu Me H 58-60 C. P1.100 4-FPh n-Pr t-Bu Me H 38-40 C. P1.101 4-FPh n-Pr t-Bu Me Me LQ P1.102 Ph [00070] t-Bu Me H 124-126 C. P1.103 4-FPh [00071] t-Bu Me Me GM P1.104 4-FPh c-Pr CEt.sub.3 Me H 68-70 C. P1.105 4-FPh c-Pr CEt.sub.3 Me Me 41-43 C. P1.106 4-FPh c-Pr CMeEt.sub.2 Me H 40-42 C. P1.107 4-FPh c-Pr CMeEt.sub.2 Me Me LQ P1.108 4-FPh c-Pr [00072] Me H 68-70 C. P1.109 4-ClPh 4-ClPh t-Bu Me Et LQ P1.110 4-ClPh 4-ClPh t-Bu Me Me LQ P1.111 Bn Ph t-Bu Me Me LQ P1.112 4-FPh Me t-Bu Me Me LQ P1.113 4-FPh c-Pr t-Bu Me Et LQ P1.114 4-FPh 4-FPh t-Bu Allyl H 80-83 C. P1.115 3-FPh 3-FPh t-Bu Me Me GM P1.116 4-ClPh CF.sub.3 t-Bu Me H GM P1.117 4-FPh 4-FPh t-Bu Et H 78-81 C. P1.118 4-FPh 4-FPh t-Bu Et Et 72-76 C. P1.119 3,5-Cl.sub.2Ph CF.sub.3 t-Bu Me H GM P1.120 1-Naphtyl 4-FPh t-Bu Me H 68-70 C. P1.121 1-Naphtyl 4-FPh t-Bu Me Me 108-110 C. P1.122 1-Naphtyl 4-FPh t-Bu Me Et GM P1.123 2-Naphtyl 4-FPh t-Bu Me Et LQ P1.124 4-ClPh Ph t-Bu Me Me 75-77 C. P1.125 3-ClPh Ph t-Bu Me Me 85-87 C. P1.126 4-FPh [00073] t-Bu Me Me 70-72 C. P1.127 4-FPh 4-FPh Allyl Me H 78-80 C. P1.128 2-Naphtyl 4-FPh t-Bu Me H GM P1.129 2-Naphtyl 4-FPh t-Bu Me Me GM P1.130 [00074] c-Pr t-Bu Me H 72-74 C. P1.131 [00075] Ph t-Bu Me Me 108-110 C. P1.132 [00076] Ph t-Bu Me Me 86-88 C. P1.133 [00077] Ph t-Bu Me H 112-114 C. P1.134 4-FPh PhCH.sub.2CH.sub.2 t-Bu Me Et LQ P1.135 4-MeSPh c-Pr t-Bu Me H GM P1.136 4-CNPh c-Pr t-Bu Me H GM P1.137 [00078] c-Pr t-Bu Me H LQ P1.138 4-FPh 4-FPh 4-ClPh Me H 112-114 C. P1.139 [00079] 4-FPh t-Bu Me H 100-102 C. P1.140 [00080] 4-FPh t-Bu Me Me 64-66 C. P1.141 [00081] c-Pr t-Bu Me H 102-104 C. P1.142 [00082] c-Pr t-Bu Me Me LQ P1.143 2,6-F.sub.2Ph c-Pr t-Bu Me Me GM P1.144 [00083] c-Pr t-Bu Me H GM P1.145 4-FPh c-Pr 1-adamantyl Me H 108-114 C. P1.146 [00084] c-Pr t-Bu Me Me 48-52 C. P1.147 4-FPh c-Pr Ph Me H 128-130 C. P1.148 Ph CF.sub.3CH.sub.2 t-Bu Me H 61-63 C. P1.149 Ph CF.sub.3CH.sub.2 t-Bu Me Me LQ P1.150 4-FPh Et t-Bu Me Me LQ P1.151 4-FPh c-Pr c-Pr Me H 104-108 C. P1.152 4-FPh c-Pr [00085] Me H GM P1.153 4-FPh c-Pr [00086] Me Me LQ P1.154 2-FPh Et t-Bu Me Me LQ P1.155 2-FPh Et t-Bu Me H LQ P1.156 4-FPh c-Pr t-Bu Et H LQ P1.157 c-Pr c-Pr t-Bu Me H 88-90 C. P1.158 3-ClPh Et t-Bu Me H LQ P1.159 3-ClPh Et t-Bu Me Me LQ P1.160 4-FPh c-Pr Et Me H LQ P1.161 4-FPh c-Pr i-Pr Me H 42-44 C. P1.162 Ph n-Bu t-Bu Me Me LQ P1.163 4-FPh n-Bu t-Bu Me Me LQ P1.164 4-FPh n-Bu t-Bu Me H LQ P1.165 2-ClPh n-Pr t-Bu Me H SO P1.166 3-FPh n-Pr t-Bu Me Me LQ P1.167 3-FPh n-Pr t-Bu Me H 38-40 C. P1.168 2-FPh n-Pr t-Bu Me Me LQ P1.169 2-FPh n-Pr t-Bu Me H LQ P1.170 3-ClPh n-Pr t-Bu Me Me 39-40 C. P1.171 3-ClPh n-Pr t-Bu Me H 50-52 C. P1.172 4-ClPh Et t-Bu Me Me 37-38 C. P1.173 4-ClPh Et t-Bu Me H 80-82 C. P1.174 2,3-F.sub.2Ph Et t-Bu Me H 66-68 C. P1.175 2,3-F.sub.2Ph Et t-Bu Me Me LQ P1.176 3-FPh Et t-Bu Me H LQ P1.177 3-FPh Et t-Bu Me Me LQ P1.178 2,3-F.sub.2Ph n-Pr t-Bu Me Me LQ P1.179 4-ClPh n-Pr t-Bu Me Me 38-40 C. P1.180 4-ClPh n-Pr t-Bu Me H 50-52 C. P1.181 2,3-F.sub.2Ph n-Pr t-Bu Me H LQ P1.182 4-OMePh n-Pr t-Bu Me H LQ P1.183 4-OMePh n-Pr t-Bu Me Me LQ P1.184 2-ClPh Et t-Bu Me H 76-78 C. P1.185 2-ClPh Et t-Bu Me Me LQ P1.186 Ph n-pentyl t-Bu Me H LQ P1.187 Ph Me CMe.sub.2Et Me H LQ P1.188 4-FPh n-pentyl t-Bu Me H LQ P1.189 4-FPh n-pentyl t-Bu Me Me LQ P1.190 2-MePh n-Pr t-Bu Me H 71-72 C. P1.191 4-MePh n-Pr t-Bu Me H LQ P1.192 Ph n-Pr CMe.sub.2Et Me H 58-60 C. P1.193 Ph n-pentyl t-Bu Me Me LQ P1.194 3-MePh n-Pr t-Bu Me H LQ P1.195 4-MePh n-Pr t-Bu Me Me LQ P1.196 3-OMePh n-Pr t-Bu Me Me LQ P1.197 3-OMePh n-Pr t-Bu Me H Gum P1.198 2-OMePh n-Pr t-Bu Me Me Gum P1.199 2-OMePh n-Pr t-Bu Me H 64-66 C. P1.200 Ph n-Pr [00087] Me H LQ P1.201 Ph n-Bu [00088] Me H LQ P1.202 Ph Me [00089] Me H 82-84 C. P1.203 Ph 4-FPh t-Bu Me H LQ CH.sub.2CH.sub.2 P1.204 3-MePh n-Pr t-Bu Me H LQ P1.205 Ph Et CMe.sub.2Et Me H 48-50 C. P1.206 Ph n-Bu t-Bu Me H 44-46 C. P1.207 Ph n-Bu CMe.sub.2Et Me H LQ P1.208 4-BrPh n-Bu t-Bu Me H 48-50 C. P1.209 Ph allyl t-Bu Me H LQ P1.210 4-OMePh n-Bu t-Bu Me H LQ P1.211 4-FPh allyl t-Bu Me H LQ P1.212 4-FPh Me [00090] Me H 80-82 C. P1.213 4-FPh Me CMe.sub.2Et Me H 60-62 C. P1.214 4-MePh n-Bu t-Bu Me H Gum P1.215 4-FPh Et CMe.sub.2Et Me H 48-50 C. P1.216 4-FPh Et [00091] Me H 96-97 C. P1.217 Ph n-Hex t-Bu Me H LQ P1.218 4-FPh n-Pr t-Bu Et H LQ P1.219 Ph 4-ClPh t-Bu Me H LQ CH.sub.2CH.sub.2 P1.220 4-FPh n-Bu [00092] Me H LQ P1.221 4-FPh n-Bu t-Bu Et H LQ P1.222 Ph n-Bu t-Bu Et H LQ P1.223 4-ClPh n-Bu t-Bu Me H LQ P1.224 4-FPh n-Pr [00093] Me H LQ P1.225 4-FPh Me t-Bu Et H 51-53 C. P1.226 Ph Et t-Bu n-Bu H LQ P1.227 4-FPh Et t-Bu Et H 70-72 C. P1.228 Ph n-Pr t-Bu Et H 65-67 C. P1.229 Ph n-Pr t-Bu n-Pr H LQ P1.230 4-FPh n-Hex t-Bu Me H LQ P1.231 4-FPh Me t-Bu n-Pr H 66-68 C. P1.232 4-FPh n-Pr CMe.sub.2Et Me H 56-58 C. P1.233 4-FPh Me t-Bu n-Bu H Gum P1.234 4-FPh n-Bu t-Bu n-Bu H LQ P1.235 Ph Me t-Bu n-Bu H LQ P1.236 Ph Me t-Bu n-Pr H LQ P1.237 4-FPh n-Bu t-Bu n-Pr H LQ P1.238 Ph n-Bu t-Bu n-Pr H LQ P1.239 3-ClPh Et t-Bu Et H 58-60 C. P1.240 3-ClPh n-Bu t-Bu Et H LQ P1.241 4-FPh n-Pr t-Bu n-Pr H LQ P1.242 4-FPh n-Bu CMe.sub.2Et Me H LQ P1.243 Ph n-Pr t-Bu n-Bu H 46-48 C. P1.244 4-FPh Et t-Bu n-Bu H LQ P1.245 4-ClPh Me t-Bu Et H Gum P1.246 4-ClPh n-Bu t-Bu Et H LQ P1.247 3-ClPh Me t-Bu Et H LQ P1.248 4-FPh n-Pr t-Bu n-Bu H Gum P1.249 2-FPh n-Pr t-Bu Et H 66-68 C. P1.250 3-FPh n-Bu t-Bu Et H 46-48 C. P1.251 2-FPh Me t-Bu Et H LQ P1.252 3-FPh Me t-Bu Et H LQ P1.253 3-FPh n-Pr t-Bu Et H 64-66 C. P1.254 3-ClPh n-Pr t-Bu Et H LQ P1.255 4-ClPh n-Pr t-Bu Et H 48-50 C. P1.256 2-FPh n-Bu t-Bu Et H 72-74 C. P1.257 4-MePh Me t-Bu Et H Gum P1.258 4-MePh Et t-Bu Et H Gum P1.259 Ph Et [00094] Me H Gum P1.260 4-MePh n-Pr t-Bu Et H Gum P1.261 4-MePh n-Bu t-Bu Et H Gum P1.262 3-OMePh n-Pr t-Bu Et H Gum P1.263 3-MePh n-Pr t-Bu Et H Gum P1.264 3-MePh n-Bu t-Bu Et H Gum 4 P1.265 4-OMePh n-Pr t-Bu Et H 60-62 8 P1.266 3-MePh Et t-Bu Et H 62-64 P1.267 3-OMePh n-Bu t-Bu Et H Gum 12 P1.268 3-OMePh Me t-Bu Et H Gum 16 P1.269 3-OMePh Et t-Bu Et H Gum P1.270 4-OMePh n-Bu t-Bu Et H Gum 20

TABLE-US-00006 TABLE P2 Compounds of formula (I-2) [00095] (I-2)

[0472] The compounds in Table P2 can be prepared as described in the examples above or similar methodology.

TABLE-US-00007 Compound Melting No. R1 R2 R3 R4 R5 Point P2.1 4-FPh 4-FPh t-Bu Me H 99-102 C. P2.2 4-FPh c-Pr t-Bu Me H LQ

TABLE-US-00008 TABLE P3 Compounds of formula (I-3) [00096] (I-3)

[0473] The compounds in Table P3 can be prepared in the presence of an acid.

TABLE-US-00009 Compound Melting No. R1 R2 R3 R4 R5 Point P3.1 4-FPh n-propyl t-Bu Me H 142-144 C.

BIOLOGICAL EXAMPLES

Example B1: Diabrotica balteata (Corn Root Worm)

[0474] Maize sprouts placed onto an agar layer in 24-well microtiter plates were treated with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions by spraying. After drying, the plates were infested with L2 larvae (6 to 10 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 4 days after infestation.

[0475] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm:

[0476] P1.1, P1.5, P1.6, P1.7, P1.8, P1.9, P1.10, P1.11, P1.12, P1.13, P1.15, P1.17, P1.18, P1.19, P1.20, P1.21, P1.22, P1.23, P1.28, P1.29, P1.30, P1.32, P1.33, P1.34, P1.35, P1.36, P1.37, P1.38, P1.42, P1.43, P1.44, P1.46, P1.47, P1.48, P1.49, P1.50, P1.51, P1.52, P1.53, P1.54, P1.55, P1.56, P1.57, P1.58, P1.59, P1.60, P1.61, P1.62, P1.63, P1.64, P1.65, P1.66, P1.67, P1.70, P1.71, P1.72, P1.74, P1.75, P1.77, P1.80, P1.81, P1.82, P1.84, P1.85, P1.86, P1.87, P1.88, P1.89, P1.9 P1.4, P1.95, P1.98, P1.99, P1.100, P1.102, P1.104, P1.105, P1.106, P1.107, P1.108, P1.110, P1.111, P1.112, P1.113, P1.114, P1.116, P1.117, P1.120, P1.121, P1.122, P1.123, P1.124, P1.125, P1.126, P1.127, P1.128, P1.129, P1.130, P1.131, P1.132, P1.133, P1.134, P1.135, P1.136, P1.137, P1.139, P1.140, P1. 141, P1.142, P1.143, P1.145, P1.146, P1.147, P1.148, P1.149, P1.150, P1.153, P1.154, P1.155, P1.158, P1.159, P1.170, P1.171, P1.172, P1.173, P1.174, P1.175, P1.176, P1.177, P1.178, P1.179, P1.180, P1.182, P1.183, P1.184, P1.185, P1.186, P1.187, P1.188, P1.190, P1.191, P1.192, P1.194, P1.195, P1.196, P1.197, P1.200, P1.201, P1.202, P1.203, P1.204, P1.205, P1.206, P1.207, P1.208, P1.210, P1.211, P1.212, P1.213, P1.215, P1.216, P1.219, P1.220, P1.223, P1.224, P1.232, P1.241, P1.242, P1.244, P1-259.

Example B2: Euschistus heros (Neotropical Brown Stink Bug)

[0477] Soybean leaves on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions. After drying the leaves were infested with N2 nymphs. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.

[0478] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm:

[0479] P1.22, P1.23, P1.29, P1.77, P1.87, P1.88, P1.89, P1.119, P1.188, P1.200, P1.216, P1.232, P1.242, P1.248.

Example B3: Myzus persicae (Green Peach Aphid): Feeding/Contact Activity

[0480] Sunflower leaf discs were placed onto agar in a 24-well microtiter plate and sprayed with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions. After drying, the leaf discs were infested with an aphid population of mixed ages. The samples were assessed for mortality 6 days after infestation.

[0481] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: P1.138.

Example B4: Myzus persicae (Green Peach Aphid): Intrinsic Activity

[0482] Test compounds prepared from 10,000 ppm DMSO stock solutions were applied by pipette into 24-well microtiter plates and mixed with sucrose solution. The plates were closed with a stretched Parafilm. A plastic stencil with 24 holes was placed onto the plate and infested pea seedlings were placed directly on the Parafilm. The infested plate was closed with a gel blotting paper and another plastic stencil and then turned upside down. The samples were assessed for mortality 5 days after infestation.

[0483] The following compounds resulted in at least 80% mortality at a test rate of 12 ppm:

[0484] P1.9, P1.17, P1.42, P1.44, P1.55, P1.60, P1.65, P1.70, P1.88, P1.98, P1.100, P1.152, P1.169, P1.171, P1.190, P1.201, P1.207, P1.259.

Example B4: Plutella xylostella (Diamond Back Moth)

[0485] 24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions by pipetting. After drying, the plates were infested with L2 larvae (10 to 15 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.

[0486] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm:

[0487] P1.1, P1.2, P1.4, P1.5, P1.6, P1.7, P1.12, P1.13, P1.17, P1.22, P1.23, P1.24, P1.34, P1.36, P1.37, P1.39, P1.46, P1.47, P1.50, P1.51, P1.52, P1.55, P1.57, P1.59, P1.62, P1.63, P1.70, P1.71, P1.72, P1.73, P1.74, P1.77, P1.80, P1.86, P1.87, P1.88, P1.89, P1.91, P1.98, P1.100, P1.104, P1.106, P1.108, P1.109, P1.110, P1.115, P1.119, P1.120, P1.122, P1.124, P1.125, P1.144, P1.162, P1.163, P1.164, P1.166, P1.167, P1.168, P1.169, P1.170, P1.171, P1.172, P1.178, P1.188, P1.190, P1.192, P1.194, P1.200, P1.201, P1.203, P1.204, P1.207, P1.208, P1.210, P1.216, P1.219, P1.220, P1.223, P1.224, P1.232, P1.242, P1.253.

Example B5: Spodoptera littoralis (Egyptian Cotton Leaf Worm)

[0488] Cotton leaf discs were placed onto agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions. After drying the leaf discs were infested with five L1 larvae. The samples were assessed for mortality, anti-feeding effect, and growth inhibition in comparison to untreated samples 3 days after infestation. Control of Spodoptera littoralis by a test sample is given when at least one of the categories mortality, anti-feedant effect, and growth inhibition is higher than the untreated sample.

[0489] The following compounds resulted in at least 80% control at an application rate of 200 ppm: P1.1, P1.2, P1.3, P1.4, P1.5, P1.6, P1.9, P1.13, P1.14, P1.17, P1.22, P1.23, P1.24, P1.25, P1.28, P1.29, P1.32, P1.34, P1.35, P1.36, P1.42, P1.44, P1.47, P1.50, P1.51, P1.52, P1.54, P1.55, P1.56, P1.59, P1.60, P1.61, P1.63, P1.64, P1.65, P1.66, P1.70, P1.72, P1.74, P1.75, P1.77, P1.88, P1.89, P1.93, P1.98, P1.100, P1.104, P1.106, P1.108, P1.115, P1.117, P1.118, P1.120, P1.122, P1.124, P1.125, P1.128, P1.129, P1.144, P1.158, P1.163, P1.164, P1.166, P1.167, P1.169, P1.170, P1.171, P1.173, P1.179, P1.180, P1.182, P1.184, P1.186, P1.188, P1.189, P1.190, P1.191, P1.192, P1.197, P1.201, P1.206, P1.207, P1.208, P1.210, P1.216, P1.219, P1.220, P1.223, P1.224, P1.229, P1.230, P1.232, P1.242, P1.255.

Example B6: Spodoptera littoralis (Egyptian Cotton Leaf Worm)

[0490] Test compounds were applied by pipette from 10,000 ppm DMSO stock solutions into 24-well plates and mixed with agar. Lettuce seeds were placed onto the agar and the multi well plate was closed by another plate which contained also agar. After 7 days the compound was absorbed by the roots and the lettuce grew into the lid plate. The lettuce leaves were then cut off into the lid plate. Spodoptera eggs were pipetted through a plastic stencil onto a humid gel blotting paper and the lid plate was closed with it. The samples were assessed for mortality, anti-feedant effect and growth inhibition in comparison to untreated samples 6 days after infestation.

[0491] The following compounds gave an effect of at least 80% in at least one of the three categories (mortality, anti-feeding, or growth inhibition) at a test rate of 12.5 ppm:

[0492] P1.55, P1.88, P1.89, P1.100, P1.119, P1.126, P1.164, P1.179, P1.180, P1.201, P1.207, P1.220, P1.222, P1.224, P1.232, P1.242.

Example B7: Tetranychus urticae (Two-Spotted Spider Mite): Feeding/Contact Activity

[0493] Bean leaf discs on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions. After drying the leaf discs were infested with a mite population of mixed ages. The samples were assessed for mortality on mixed population (mobile stages) 8 days after infestation.

[0494] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

[0495] P1.1, P1.3, P1.4, P1.5, P1.9, P1.13, P1.35, P1.50, P1.52, P1.54, P1.59, P1.60, P1.61, P1.65, P1.72, P1.84, P1.85, P1.86, P1.88, P1.94, P1.142, P1.145, P1.151, P1.158, P1.167, P1.170, P1.171, P1.184, P1.201, P1.203, P1.208, P1.219, P1.224, P1.238, P1.250, P1.253, P1.257.

Example B8: Thrips tabaci (Onion Thrips): Feeding/Contact Activity

[0496] Sunflower leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions. After drying the leaf discs were infested with a thrips population of mixed ages. The samples were assessed for mortality 6 days after infestation.

[0497] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

[0498] P1.2, P1.4, P1.5, P1.7, P1.9, P1.36, P1.42, P1.56, P1.59, P1.61, P1.74, P1.90, P1.91, P1.219.

Example B9: Aedes aegypti (Yellow Fever Mosquito)

[0499] Test solutions, at an application rate of 200 ppm in ethanol, were applied to 12 well tissue culture plates. Once the deposits were dry, five, two to five day old adult female Aedes aegypti were added to each well, and sustained with a 10% sucrose solution in a cotton wool plug. Assessment of knockdown was made one hour after introduction, and mortality was assessed at 24 and 48 hours after introduction.

[0500] The following compounds gave at least 80% control of Aedes aegypti after 48 h and/or 24 h:

[0501] P1.1, P1.2, P1.3, P1.4, P1.5, P1.6, P1.7, P1.8, P1.9, P1.10, P1.11, P1.12, P1.13, P1.14, P1.15, P1.16, P1.17, P1.18, P1.19, P1.20, P1.21, P1.22, P1.23, P1.24, P1.25, P1.26, P1.27, P1.28, P1.29, P1.30, P1.31, P1.32, P1.33, P1.34, P1.35, P1.36, P1.37, P1.38, P1.39, P1.40, P1.41, P1.42, P1.43, P1.44, P1.45, P1.46, P1.47, P1.48, P1.49, P1.50, P1.51, P1.52, P1.53, P1.54, P1.55, P1.56, P1.57, P1.58, P1.59, P1.60, 6 P1.1, P1.62, P1.63, P1.64, P1.65, P1.66, P1.67, P1.69, P1.70, P1.71, P1.72, P1.73, P1.74, P1.75, P1.76, P1.77, P1.78, P1.79, P1.80, P1.81, P1.82, P1.83, P1.84, P1.85, P1.86, P1.87, P1.88, P1.89, P1.90, P1.91, P1.92, P1.93, P1.94, P1.95, P1.96, P1.97, P1.98, P1.99, P1.100, P1.101, P1.102, P1.103, P1.104, P1.105, P1.106, P1.107, P1.108, P1.154, P1.155, P1.156, P1.157, P1.158, P1.159, P1.160, P1.161, P1.162, P1.163, P1.164, P1.165, P1.166, P1.167, P1.168, P1.169, P1.170, P1.171, P1.172, P1.173, P1.174, P1.175, P1.176, P1.177, P1.178, P1.179, P1.180, P1.181, P1.182, P1.183, P1.184, P1.185, P1.186, P1.187, P1.188, P1.189, P1.190, P1.191, P1.192, P1.193, P1.194, P1.195, P1.196, P1.197, P1.198, P1.199, P1.200, P1.201, P1.202, P1.204, P1.205, P1.206, P1.207, P1.208, P1.210, P1.211, P1.213, P1.214, P1.215, P1.216, P1.217, P1.218, P1.221, P1.223, P1.228, P1.229, P1.230, P1.232, P1.235, P1.237, P1.238, P1.240, P1.242, P1.245, P1.248, P1.250, P1.254, P1.255, P1.256, P1.259, P2.1, P2.2.

Example B10: Anopheles stephensi (Indian Malaria Mosquito)

[0502] Test solutions, at an application rate of 200 ppm in ethanol, were applied to 12 well tissue culture plates. Once the deposits were dry, five, two to five day old adult female Anopheles stephensi were added to each well, and sustained with a 10% sucrose solution in a cotton wool plug. Assessment of knockdown was made one hour after introduction, and mortality was assessed at 24 and 48 hours after introduction.

[0503] The following compounds gave at least 80% control of Anopheles stephensi after 48 h and/or 24 h:

[0504] P1.2, P1.3, P1.4, P1.5, P1.6, P1.7, P1.8, P1.9, P1.10, P1.11, P1.12, P1.13, P1.15, P1.16, P1.17, P1.18, P1.19, P1.20, P1.21, P1.22, P1.28, P1.29, P1.34, P1.35, P1.36, P1.37, P1.38, P1.39, P1.40, P1.41, P1.42, P1.43, P1.44, P1.46, P1.47, P1.48, P1.50, P1.51, P1.52, P1.53, P1.54, P1.55, P1.56, P1.58, P1.59, P1.60, P1.61, P1.62, P1.63, P1.64, P1.65, P1.66, P1.67, P1.69, P1.70, P1.71, P1.72, P1.73, P1.74, P1.75, P1.77, P1.79, P1.80, P1.81, P1.82, P1.84, P1.85, P1.86, P1.87, P1.88, P1.89, P1.90, P1.91, P1.92, P1.93, P1.94, P1.96, P1.98, P1.99, P1.100, P1.101, P1.104, P1.105, P1.106, P1.107, P1.108, P1.154, P1.155, P1.156, P1.158, P1.159, P1.160, P1.161, P.1.162, P1.163, P1.164, P1.165, P1.166, P1.167, P1.168, P1.169, P1.170, P1.171, P1.172, P1.173, P1.174, P1.175, P1.176, P1.178, P1.179, P1.180, P1.181, P1.182, P1.183, P1.184, P1.185, P1.186, P1.187, P1.188, P1.189, P1.190, P1.191, P1.192, P1.193, P1.194, P1.195, P1.196, P1.197, P1.198, P1.199, P1.200, P1.201, P1.202, P1.203, P1.204, P1.205, P1.206, P1.207, P1.208, P1.210, P1.213, P1.214, P1.215, P1.216, P1.217, P1.218, P1.220, P1.221, P1.222, P1.223, P1.224, P1.225, P1.226, P1.227, P1.228, P1.229, P1.230, P1.231, P1.232, P1.233, P1.234, P1.235, P1.236, P1.237, P1.238, P1.239, P1.242, P1.243, P1.244, P1.245, P1.246, P1.247, P1.248, P1.250, P1.254, P1.256, P2.1, P2.2.

Example B11: Evaluation of Insecticide Impregnated Polymer Surfaces

[0505] Preparation of polymeric sheets: Compound P1.17 was impregnated into LDPE (low density polyethylene) by mixing the respective polymer with the compound at high temperatures and the resultant polymeric material was then mould into thin discs or plaques.

[0506] Twenty four hours prior to the relevant assessment intervals, three to five day old non-blood fed adult mosquitoes were taken from the culture and lightly anaesthetised with carbon dioxide. Ten females were selected and placed in a 250 ml plastic cup, retained with a net lid, provided with a 10% sucrose solution soaked in a cotton wool bung and held under culturing environmental conditions.

[0507] After twenty four hours, impregnated polymer sheets (measuring about 150 mm in diameter and about 0.1 mm in thickness) were removed from storage and wrapped around the glazed side of an 11 cm ceramic tile and held in place with an elastic band. The age of the polymer sheets used were either 1-2 weeks or 10 weeks old. A cup of the pre-selected mosquitoes were again lightly anaesthetised with carbon dioxide and transferred from the holding cup to the base of a 9 cm plastic Petri dish. The relevant impregnated polymer sheet was placed over the Petri dish and held in place with an elastic band. Once the mosquitoes had recovered from the anaesthetic, ca. 1 minute, the impregnated polymer sheet was placed on a holding rack, such that treated side was at an angle of 60 to the horizontal.

[0508] After one hour an assessment of mosquito knockdown was made. A mosquito was said to be knocked down if it was unable to right itself once it had fallen over. The mosquitoes were lightly anaesthetised again, and removed from the Petri dish exposure chamber and returned to the holding cups. The mosquitoes were supplied with a 10% sucrose solution soaked in a cotton wool bung and held under culturing environmental conditions. An assessment of mortality was made 24 hours and 48 hours after exposure. A mosquito was said to be dead if it is unable to right itself once it had fallen over.

[0509] Compound P1.17 showed at least 80% control of Aedes Aegypti and Anopheles stephensi after 48 h and/or 24 h at a concentration of 2% of active ingredient in LDPE sheetsafter 1 week, after 2 weeks and after 10 weeks.