BENZOXABOROLE FUNGICIDES

Abstract

Compounds of formula (I) are as defined in the claims, and their use in compositions and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants and to processes for the preparation of these compounds.

##STR00001##

Claims

1. A method for controlling or preventing infestation of plants or plant propagation material and/or harvested food crops susceptible to microbial attack by treating plants or plant propagation material and/or harvested food crops with an effective amount of an oxaborole of general formula (I) ##STR00153## wherein R.sup.1 is H, fluorine, chlorine, bromine, cyano, nitro, unsubstituted or substituted C.sub.1-C.sub.4alkyl, unsubstituted or substituted C.sub.1-C.sub.4alkoxy, unsubstituted or substituted or C.sub.1-C.sub.4haloalkyl; R.sup.3 is selected from H, unsubstituted or substituted C.sub.1-C.sub.4alkyl, unsubstituted or substituted C.sub.1-C.sub.4haloalkyl, unsubstituted or substituted six- to ten-membered aryl, unsubstituted or substituted five- to six-membered heteroary, unsubstituted or substituted C.sub.3-C.sub.7 cycloalkyl, or unsubstituted or substituted C.sub.3-C.sub.7 heterocycloalkyl; R.sup.2 is O, NOR.sup.5, NNR.sup.6R.sup.7, NN(CO)R.sup.6, NNH(CO)NR.sup.8R.sup.9 or NNH(CS)NR.sup.8R.sup.9 R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are independently of each other hydrogen, unsubstituted or substituted C.sub.1-C.sub.10alkyl, unsubstituted or substituted C.sub.1-C.sub.10 haloalkyl, unsubstituted or substituted C.sub.1-C.sub.10alkoxy(C.sub.1-C.sub.10)alkyl, unsubstituted or substituted C.sub.2-C.sub.10alkenyl, unsubstituted or substituted C.sub.2-C.sub.10haloalkenyl, unsubstituted or substituted C.sub.2-C.sub.10alkynyl, unsubstituted or substituted C.sub.3-C.sub.7cycloalkyl(alkylene).sub.(0-2), unsubstituted or substituted six- to ten-membered-aryl(alkylene).sub.(0-2), or unsubstituted or substituted five- to ten-membered heteroaryl(alkylene).sub.(0-2); wherein the substituents for the substituted aryl, heteroaryl, cycloalkyl and heterocycloalkyl moieties can be independently mono- or polysubstituted by substituents selected from the group consisting of halogen, hydroxy, nitro, cyano, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkenyl, C.sub.1-C.sub.6haloalkenyl, C.sub.1-C.sub.6alkinyl, C.sub.1-C.sub.6haloalkinyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkenyloxy, C.sub.1-C.sub.6haloalkenyloxy, C.sub.1-C.sub.6alkinyloxy, C.sub.1-C.sub.6haloalkinyl, C.sub.1-C.sub.6alkoxy-C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkoximino, C.sub.1-C.sub.6alkylendioxy, C(O)(C.sub.1-4 alkyl), (C.sub.1-4 alkyl)-C(O)(C.sub.1-4 alkyl), C(O)OH, (C.sub.1-4 alkyl)-C(O)OH, unsubstituted or substituted six- to ten-membered-aryl(alkylene).sub.(0-1) and unsubstituted or substituted six- to ten-membered-aryl(alkylene).sub.(0-1)oxy; and wherein the substituents for the substituted cycloalkyl, heterocycloalkyl and alkyl can be independently mono- or polysubstituted by substituents selected from oxo, OH, CN, NO.sub.2, F, Cl, C.sub.1-4alkoxy, C(O)(C.sub.1-4 alkoxy), C(O)(C.sub.1-4 alkyl), C(O)NH(C.sub.1-4 alkyl), C(O)N(C.sub.1-4 alkyl).sub.2, C.sub.1-4alkylamino, unsubstituted or substituted five- to ten-membered aryl, unsubstituted or substituted five- to six-membered heteroary, unsubstituted or substituted C.sub.3-C.sub.7 cycloalkyl, and unsubstituted or substituted C.sub.3-C.sub.7 heterocycloalkyl; and wherein the heterocycloalkyl and the heteroaryl contain 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for the ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms; or an agronomically acceptable salt, stereoisomer, diastereoisomer, enantiomer, tautomer, atriopisomer or N-oxide thereof.

2. A compound of formula (I) ##STR00154## wherein R.sup.1 is H, fluorine, chlorine, bromine, cyano, nitro, unsubstituted or substituted C.sub.1-C.sub.4alkyl, unsubstituted or substituted C.sub.1-C.sub.4alkoxy, unsubstituted or substituted or C.sub.1-C.sub.4haloalkyl; R.sup.3 is selected from H, unsubstituted or substituted C.sub.1-C.sub.4alkyl, unsubstituted or substituted C.sub.1-C.sub.4haloalkyl, unsubstituted or substituted six- to ten-membered aryl, unsubstituted or substituted five- to six-membered heteroary, unsubstituted or substituted C.sub.3-C.sub.7 cycloalkyl, or unsubstituted or substituted C.sub.3-C.sub.7 heterocycloalkyl; R.sup.2 is O, NOR.sup.5, NNR.sup.6R.sup.7, NN(CO)R.sup.6, NNH(CO)NR.sup.8R.sup.9 or NNH(CS)NR.sup.8R.sup.9 R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are independently of each other hydrogen, unsubstituted or substituted C.sub.1-C.sub.10alkyl, unsubstituted or substituted C.sub.1-C.sub.10 haloalkyl, unsubstituted or substituted C.sub.1-C.sub.10alkoxy(C.sub.1-C.sub.10)alkyl, unsubstituted or substituted C.sub.2-C.sub.10alkenyl, unsubstituted or substituted C.sub.2-C.sub.10haloalkenyl, unsubstituted or substituted C.sub.2-C.sub.10alkynyl, unsubstituted or substituted C.sub.3-C.sub.7cycloalkyl(alkylene).sub.(0-2), unsubstituted or substituted six- to ten-membered-aryl(alkylene).sub.(0-2), or unsubstituted or substituted five- to ten-membered heteroaryl(alkylene).sub.(0-2); wherein the substituents for the substituted aryl, heteroaryl, cycloalkyl and heterocycloalkyl moieties can be independently mono- or polysubstituted by substituents selected from the group consisting of halogen, hydroxy, nitro, cyano, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkenyl, C.sub.1-C.sub.6haloalkenyl, C.sub.1-C.sub.6alkinyl, C.sub.1-C.sub.6haloalkinyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkenyloxy, C.sub.1-C.sub.6haloalkenyloxy, C.sub.1-C.sub.6alkinyloxy, C.sub.1-C.sub.6haloalkinyl, C.sub.1-C.sub.6alkoxy-C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkoximino, C.sub.1-C.sub.6alkylendioxy, C(O)(C.sub.1-4 alkyl), (C.sub.1-4 alkyl)-C(O)(C.sub.1-4 alkyl), C(O)OH, (C.sub.1-4 alkyl)-C(O)OH, unsubstituted or substituted six- to ten-membered-aryl(alkylene).sub.(0-1) and unsubstituted or substituted six- to ten-membered-aryl(alkylene).sub.(0-1)oxy; and wherein the substituents for the substituted cycloalkyl, heterocycloalkyl and alkyl can be independently mono- or polysubstituted by substituents selected from oxo, OH, CN, NO.sub.2, F, Cl, C.sub.1-4alkoxy, C(O)(C.sub.1-4 alkoxy), C(O)(C.sub.1-4 alkyl), C(O)NH(C.sub.1-4 alkyl), C(O)N(C.sub.1-4 alkyl).sub.2, C.sub.1-4alkylamino, unsubstituted or substituted five- to ten-membered aryl, unsubstituted or substituted five- to six-membered heteroary, unsubstituted or substituted C.sub.3-C.sub.7 cycloalkyl, and unsubstituted or substituted C.sub.3-C.sub.7 heterocycloalkyl; and wherein the heterocycloalkyl and the heteroaryl contain 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for the ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms; or an agronomically acceptable salt, stereoisomer, diastereoisomer, enantiomer, tautomer, atriopisomer or N-oxide thereof provided that if R.sup.1 is H then R.sup.5 is not methyl if R.sup.1 is H then R.sup.5 is not benzyl R.sup.1 and R.sup.3 are defined under formula I, provided that If R.sup.1 is H then C(O)R.sup.3 is not 6-CHO If R.sup.1 is H then C(O)R.sup.3 is not 4-CHO If R.sup.1 is 4-F then C(O)R.sup.3 is not 7-CHO If R.sup.1 is 4-OCH.sub.3 then C(O)R.sup.3 is not 7-CHO If R.sup.1 is H then C(O)R.sup.3 is not 5-CHO If R.sup.1 is H then C(O)R.sup.3 is not 7-CHO and if R.sup.1 is H then R.sup.3 is not butyl or phenyl.

3. A compound of formula (I) according to claim 1 wherein R.sup.2 is O, NOH, NOCH3-CHCHCl, NOCH.sub.3, NOCH.sub.2-Ph, NOCH.sub.2CH.sub.3, NOCH.sub.2CHCH, NOCH.sub.2CHC(CH.sub.3).sub.2, NOCH.sub.2CH(CH.sub.3).sub.2, NOCH.sub.2-4-NO.sub.2-Ph, NOCH.sub.2-4-Me-Ph, NOCH.sub.2-4-Cl-Ph, NOCH.sub.2-2-F-Ph, NOCH.sub.2-2-Cl-4-F-Ph, NOCH.sub.2-2,6-Cl-Ph, NOCH.sub.2-2,4-Cl-Ph, NOCH.sub.2-2,4,5-Cl-Ph, NOCH.sub.2-2,3,4,5,6-F-Ph, NOCH(CH.sub.3).sub.2, NOC(CH.sub.3).sub.3, NO-4-NO.sub.2-Ph, NO-4-CN-Ph, NO(CH.sub.2).sub.5CH.sub.3, NO(CH.sub.2).sub.3CH.sub.3, NO(CH.sub.2).sub.3C(O)OCH.sub.2CH.sub.3, NO(CH.sub.2).sub.2CH.sub.3, NO(CH.sub.2).sub.2CH.sub.2C(O)OH, NO(CH.sub.2).sub.11CH.sub.3, NNHCH.sub.2-Ph, NNHCH.sub.2OC(O)CH.sub.2CH.sub.3, NNHCH.sub.2C(O)OEt, NNHCH(CH.sub.3).sub.2, NNHC(S)NH-Ph, NNHC(S)NH-Me, NNHC(S)NHCH.sub.2-Ph, NNHC(S)NHCH.sub.2-Ph, NNHC(S)NHCH.sub.2CH.sub.3, NNHC(S)NHCH.sub.2CHCH.sub.2, NNHC(S)NH.sub.2, NNHC(O)OMe, NNHC(O)OEt, NNHC(O)NH-Ph, NNHC(O)NH-4-OMe-Ph, NNHC(O)NH-2,4-Ph, NNHC(O)-4-NO.sub.2-Ph, NNHC(O)-4-Cl-Ph, NNHC(O)-3-pyridyl, NNHC(O)-2-NO.sub.2-Ph, NNHC(O)-2,5-Cl-Ph, NNH-4-OCH.sub.3-Ph, NNH-4-Me-Ph, NNH-4-Cl-Ph, NNH-4-CF.sub.3-Ph, NNH-3-NO.sub.2-Ph, NNH-3,5-Cl-Ph, NNH-2-NO.sub.2-Ph, NNH-2,6-Cl-Ph, NNH-2,6-Cl-4-CF.sub.3-Ph, NNH-2,5-F-Ph, NNH-2,4-F-Ph, NNH-2,4-Cl-Ph, NNH.sub.2, NN(CH.sub.3)Ph, NN(CH.sub.3)CH.sub.2-Ph, NN(CH.sub.3)CH.sub.2CH.sub.3, NN(CH.sub.3)CH.sub.2CH(CH.sub.3).sub.2, NN(CH.sub.3)CH.sub.2C(CH.sub.3).sub.3, NN(CH.sub.3)CH.sub.2-4-F-Ph, NN(CH.sub.3)CH.sub.2-4-Cl-Ph, NN(CH.sub.3)CH.sub.2-3,5-F-Ph, NN(CH.sub.3)CH.sub.2-3,5-Cl-Ph, NN(CH.sub.3)CH.sub.2-2,6-F-Ph, NN(CH.sub.3)CH.sub.2-2,6-Cl-Ph, NN(CH.sub.3)CH.sub.2-2,5-F-Ph, NN(CH.sub.3)CH.sub.2-2,5-Cl-Ph, NN(CH.sub.3)CH.sub.2-2,4-F-Ph, NN(CH.sub.3)CH.sub.2-2,4-Cl-Ph, NN(CH.sub.3)CH.sub.2-2,4, 6-F-Ph, NN(CH.sub.3)CH.sub.2-2,4, 6-Cl-Ph, NN(CH.sub.3)CH(CH.sub.3).sub.2, NN(CH.sub.3)C(CH.sub.3).sub.3, NN(CH.sub.3)-4-F-Ph, NN(CH.sub.3)-4-Cl-Ph, NN(CH.sub.3)-2,4-F-Ph, NN(CH.sub.3)-2,4-Cl-Ph, NN(CH.sub.3).sub.2, NN(CH.sub.3)(CH.sub.2).sub.5CH.sub.3, NN(CH.sub.3)(CH.sub.2).sub.4CH.sub.3, NN(CH.sub.3)(CH.sub.2).sub.3CH.sub.3, NN(CH.sub.3)(CH.sub.2).sub.2CH.sub.3, ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161##

4. A compound of formula (I) according to claim 1 wherein R.sup.2 is selected from O, NOH, NOCH.sub.3, NOCH.sub.2CH.sub.3, NO(CH.sub.2).sub.2CH.sub.3, NO(CH.sub.2).sub.3CH.sub.3, NO(CH.sub.2).sub.4CH.sub.3, NO(CH.sub.2).sub.5CH.sub.3, NOCH(CH.sub.3).sub.2, NOC(CH.sub.3).sub.3, NOCH.sub.2CH(CH.sub.3).sub.2, NOCH.sub.2C(CH.sub.3).sub.3, NOPh, NO-4-F-Ph, NO-4-Cl-Ph, NO-2,4-F-Ph, NO-2,4-Cl-Ph, NOCH.sub.2-Ph, NOCH.sub.2-4-F-Ph, NOCH.sub.2-4-Cl-Ph, NOCH.sub.2-2,4-F-Ph, NOCH.sub.2-2,5-F-Ph, NOCH.sub.2-2,6-F-Ph, NOCH.sub.2-3,5-F-Ph, NOCH.sub.2-2,4, 6-F-Ph, NOCH.sub.2-2,4-Cl-Ph, NOCH.sub.2-2,5-Cl-Ph, NOCH.sub.2-2,6-Cl-Ph, NOCH.sub.2-3,5-Cl-Ph, NOCH.sub.2-2,4, 6-Cl-Ph, NOCH.sub.2-2-OMePh, NOCH.sub.2-3-OMePh, NOCH.sub.2-4-OMePh, NO-2-OMe-Ph, NO-3-OMePh, NO-4-OMePh, ##STR00162## ##STR00163##

5. A compound of formula (I) according to claim 1 wherein R.sup.2 is selected from ##STR00164## ##STR00165## ##STR00166##

6. A compound of formula (I) according to claim 1 wherein R.sup.2 is NOR.sup.5, NNR.sup.6R.sup.7, NNH(CO)NR.sup.8R.sup.9, NNH(CS)NR.sup.8R.sup.9.

7. A compound of formula (I) according to claim 1 wherein R.sup.1 is selected from F and Cl, and R.sup.3 is selected from H, C.sub.1-C.sub.4alkyl, aryl, heteroaryl or C.sub.1-C.sub.4haloalkyl, and C.sub.3-C.sub.7 cycloalkyl.

8. A compound of formula (II) ##STR00167## wherein R.sup.1 and R.sup.3 are defined under formula (I), provided that if R.sup.1 is H then C(O)R.sup.3 is not 6-CHO, if R.sup.1 is H then C(O)R.sup.3 is not 4-CHO, if R.sup.1 is 4-F then C(O)R.sup.3 is not 7-CHO, if R.sup.1 is 4-OCH.sub.3 then C(O)R.sup.3 is not 7-CHO if R.sup.1 is H then C(O)R.sup.3 is not 5-CHO, if R.sup.1 is H then C(O)R.sup.3 is not 7-CHO, and if R.sup.1 is H then R.sup.3 is not butyl or phenyl.

9. A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a compound of formula (I) as defined in claim 1 is applied to the plants, to parts thereof or the locus thereof.

10. A composition for controlling and protecting against phytopathogenic microorganisms, comprising a compound of formula (I) as defined in claim 1 and at least one auxiliary.

11. A method of controlling phytopathogenic diseases on useful plants or plant propagation material thereof, which comprises applying to said plant propagation material a fungicidally effective amount of a plant propagation material protecting composition comprising a compound of formula (I) as defined in claim 1, together with a suitable carrier therefor.

12. The composition of claim 10 further comprising at least one additional active ingredient.

Description

PREPARATION EXAMPLES

[0180] The following examples illustrate the above-described invention in greater detail without limiting it.

Example 1

Synthesis of 1-Bromo-2,5-bis-bromomethyl-4-fluoro-benzene

[0181] ##STR00043##

[0182] To a stirred solution of 1-Bromo-4-fluoro-2,5-dimethyl-benzene (35 g, 0.1723 mol) in acetonitrile (350 ml) was added N-Bromosuccinimide (64.42 g, 0.3619 mol) followed by AIBN (1.4 g, 0.0086 mol) at room temperature. Resulting mixture was heated to reflux at 90 C. for 4 h. Reaction mixture was cooled to ambient temperature and acetonitrile was evaporated completely under vacuum. Resulting residue obtained was partitioned between Ethyl acetate (500 mL) and water (500 mL). Organic layer was separated and the aqueous layer was extracted with ethyl acetate (2200 mL). Combined organic layer was washed with water (2250 mL) followed by brine (250 mL) and dried over Na.sub.2SO.sub.4, filtered and evaporated completely to give crude mass (62 g). This crude compound obtained was purified by flash chromatography using 2% ethyl acetate in hexane as eluent to afford pure 1-Bromo-2,5-bis-bromomethyl-4-fluoro-benzene (35 g, 56.23% of theoretical yield) as white solid.

[0183] .sup.1H NMR (400 MHz, CDCl.sub.3) ppm 4.42 (s, 2H), 4.50 (s, 2H) 7.2 (d, J=9.6 Hz, 1H), 7.6 (d, J=7 Hz, 1H)

[0184] LCMS M+H 361

Example 2

Synthesis of (5-Bromo-2-fluoro-4-hydroxymethyl-phenyl)-methanol

[0185] ##STR00044##

[0186] To a stirred suspension of 1-Bromo-2,5-bis-bromomethyl-4-fluoro-benzene (30 g, 0.08313 mol) in 1:1 mixture of 1,4-Dioxane (200 mL) and Water (200 mL) was added CaCO.sub.3 (24.96 g, 0.2494 mol) at ambient temperature. Resulting mixture was heated to reflux at 100 C. for 12 h. Reaction mixture was then cooled to 0 C. and pH 4 was adjusted with 6N HCl solution. It was then extracted with ethyl acetate (3250 mL). Combined organic layer was washed with brine solution (250 mL). Organic layer was dried over Na.sub.2SO.sub.4, filtered and evaporated completely to afford (5-Bromo-2-fluoro-4-hydroxymethyl-phenyl)-methanol (19 g, 97.43% of theoretical yield) as white solid.

[0187] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 4.46 (d, J=5.6 Hz, 2H), 4.51 (d, J=5.8 Hz, 2H), 4.51 (t, J=5.8 Hz, 1H), 5.57 (t, J=5.6 Hz, 1H), 7.245 (d, J=10.88 Hz, 1H), 7.6 (d, J=6.8 Hz, 1H)

[0188] LCMS M+H 235

Example 3

Synthesis of 2-[[2-bromo-5-fluoro-4-(tetrahydropyran-2-yloxymethyl)phenyl] methoxy]tetrahydropyran

[0189] ##STR00045##

[0190] To a stirred solution of (5-Bromo-2-fluoro-4-hydroxymethyl-phenyl)-methanol (20.0 g, 0.08508 mol) in dry DMF (160 mL) was added p-TSA (0.89 g, 0.004 mol) at ambient temperature. Resulting reaction mixture was cooled to 0 C. To this was added 3,4-dihydro-2H-pyran (28.6 g, 0.3403 mol) drop wise over a period of 30 min. Reaction mixture was stirred for 24 h at ambient temperature. After completion, monitored by TLC, reaction mixture was quenched with ice cold water (200 mL). Added saturated solution of NaHCO.sub.3 (50 mL) and then extracted with ethyl acetate (3200 mL). Combined organic layer was washed with water (3200 mL) followed by brine wash (200 mL). Organic layer was dried over Na.sub.2SO.sub.4, filtered and evaporated completely to give oily crude mass (35 g). This crude obtained was purified by flash chromatography using 8% ethyl acetate in hexane as eluent to afford 2-[[2-bromo-5-fluoro-4-(tetrahydropyran-2-yloxymethyl)phenyl] methoxy] tetrahydropyran (25 g, 73.27% of theoretical yield) as an oily compound.

[0191] .sup.1H NMR (400 MHz, CHLOROFORM-d) ppm 1.52-1.60 (m, 3H), 1.627-1.674 (m, 3H) 1.71-1.76 (m, 3H), 1.77-1.866, (m, 3H), 3.59 (br. s., 2H) 3.85-3.93 (m, 2H) 4.50-4.57 (m, 2H) 4.72-4.80 (m, 4H) 7.26 (s, 1H) 7.60 (d, J=6.64 Hz, 1H)

Example 4

Synthesis of 2-[4-fluoro-2,5-bis(tetrahydropyran-2-yloxymethyl)phenyl]-4,4,5,5-tetra methyl-1,3,2-dioxaborolane

[0192] ##STR00046##

[0193] To a stirred solution of 2-[[2-bromo-5-fluoro-4-(tetrahydropyran-2-yloxymethyl)phenyl]methoxy]tetrahydropyran (14.7 g, 36.4 mmol) in 1,4 dioxane (140 mL) was added fused potassium acetate (3 equiv., 109 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.5 equiv., 54.7 mmol) and finally [1,1-Bis(diphenylphosphino) ferrocene]-dichloropalladium(II) dichloromethane adduct (0.05 equiv., 1.82 mmol) under nitrogen. The reaction mixture was heated at 100 C. for 3 h. The reaction mixture was cooled to ambient temperature and diluted with water (100 mL) and then extracted with ethyl acetate (3200 mL). Combined organic layer was washed with water (3200 mL) followed by brine wash (200 mL). Organic layer was dried over Na.sub.2SO.sub.4, filtered and evaporated completely to give crude compound. This crude obtained was purified by flash chromatography using 10% ethyl acetate in hexane as eluent to afford desired compound 2-[4-fluoro-2,5-bis(tetrahydropyran-2-yloxymethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15 g, 33.30 mmol, 91.4% of theoretical yield).

[0194] .sup.1H NMR (400 MHz, CHLOROFORM-d) ppm 1.31 (s, 12H), 1.49-1.86 (m, 9H), 3.50-3.58 (m, 2H), 3.87-3.96 (m, 2H), 4.52 (d, J=11.54 Hz, 1H) 4.69-4.84 (m, 4H) 4.90-4.95 (m, 1H) 7.25 (d, J=11.71 Hz, 1H) 7.83 (d, J=8.28 Hz, 1H)

Example 5

Synthesis of (5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)methanol

[0195] ##STR00047##

[0196] Method A:

[0197] To a stirred solution of 2-[4-fluoro-2,5-bis(tetrahydropyran-2-yloxymethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (16 g, 35.52 mmol) in methanol (100 mL) was added 6N HCl (100 mL) in drops at 0 C. over a period of 5 min. Reaction mixture was then allowed to stir at ambient temperature for 12 h. The reaction mixture was diluted with water (100 mL) and then extracted with dichloromethane (3100 mL) Organic layer was dried over Na.sub.2SO.sub.4, filtered and evaporated completely to give crude compound as yellow oil. Crude mass was further purified by trituration with cyclohexane afforded (5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)methanol (4 g, 21.9831 mmol, 61.88% of theoretical yield) as a solid compound.

[0198] Method B:

[0199] To a stirred solution of 2-[[2-bromo-5-fluoro-4-(tetrahydropyran-2-yloxymethyl)phenyl] methoxy]tetrahydropyran (20.0 g, 0.04959 mol) in dry THF (200 mL) was added n-BuLi (2.5 M in n-Hexane) (27.7 mL, 4.44 g, 0.06942 mol) drop wise at 78 C. over a period of 30 min. Reaction mixture was stirred at 78 C. for 45 min. To this resulting reaction mixture was added Tri-isopropyl borate (13.99 g, 0.0743 mol) drop wise over a period of 15 min. Reaction mixture was allowed to come at ambient temperature and stirred for 12 h. Starting was consumed completely, confirmed by TLC. The reaction mixture was then cooled to 0 C., added 6N HCl solution (200 mL) drop wise and stirred at ambient temperature for 24 h. The resulting mixture was diluted with water (50 mL) and extracted with ethyl acetate (3100 mL). Combined organic layer was washed with water (200 mL) followed by brine wash (100 mL). Organic layer was dried over Na.sub.2SO.sub.4, filtered and evaporated completely to afford (5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)methanol (5 g, 55% of theoretical yield) as a semi solid.

[0200] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 4.52-4.59 (m, 2H), 4.96 (s, 2H), 5.28 (t, J=5.64 Hz, 1H), 7.2 (d, J=10.44 Hz, 1H) 7.84 (d, J=7.64 Hz, 1H), 9.21 (s., 1H)

[0201] LCMS M+H 182

Example 6

Synthesis of 5-Fluoro-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborole-6-carbaldehyde

[0202] ##STR00048##

[0203] To a stirred solution of compound (5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)methanol in DCM (150 mL) was added Pyridinium Chlorochromate (17.76 g, 0.08243 mol) and celite (20 g) at 0 C. lot wise. Reaction mixture was then stirred at ambient temperature for 6 h. starting was consumed completely as confirmed by TLC. Reaction mixture was then filtered through celite bed and bed was washed with DCM (50 mL). Filtrate was evaporated and crude obtained was purified by flash chromatography using 60% ethyl acetate in hexane as eluent to afford pure 5-Fluoro-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborole-6-carbaldehyde (1.8 g, 18.2% of theoretical yield).

[0204] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 5.06 (s, 2H) 7.47 (d, J=10.96 Hz, 1H) 8.23 (d, J=7.16 Hz, 1H) 9.47 (s, 1H) 10.24 (s, 1H)

[0205] LCMS M+H 181.1 (RT; 1.24)

Example 7

Synthesis of 1-bromo-2,5-bis(bromomethyl)-4-chloro-benzene

[0206] ##STR00049##

[0207] To a stirred solution of 1-Bromo-4-fluoro-2,5-dimethyl-benzene (20 g, 91.114 mmol) in acetonitrile (200 ml) was added N-Bromosuccinimide (34 g, 191.3318) followed by AIBN (0.748 g, 4.55 mmol) at ambient temperature. Resulting reaction mixture was heated to reflux at 90 C. for 4 h. starting was consumed completely, as confirmed by TLC. Reaction mixture was then cooled to ambient temperature and acetonitrile was evaporated completely under vacuum. Residue obtained was partitioned between Ethyl acetate (50 mL) and water (50 mL). Organic layer was separated and aqueous was extracted with ethyl acetate (220 mL). Combined organic layer was washed with water (220 mL) followed by brine (20 mL) and dried over Na.sub.2SO.sub.4, filtered and evaporated completely to afford crude mass (56 g). Crude mass was further purified by crystallisation using cyclohexane as the solvent to afford 1-bromo-2,5-bis(bromomethyl)-4-chloro-benzene (21 g, 61% of theoretical yield)

[0208] .sup.1H NMR (400 MHz, CDCl.sub.3) ppm 4.51 (d, J=5.02 Hz, 4H) 7.49 (s, 1H) 7.65 (s, 1H)

Example 8

Synthesis of [4-(acetoxymethyl)-2-bromo-5-chloro-phenyl]methyl acetate

[0209] ##STR00050##

[0210] To a stirred solution of 1-bromo-2,5-bis(bromomethyl)-4-chloro-benzene (17 g, 45.057 mmol) in DMF (50 ml) was added potassium acetate (22.79 g, 225.28 mmol) slowly at ambient temperature. Resulting reaction mixture was heated at 70 C. for 3 h. starting was consumed completely, as confirmed by TLC. Reaction mixture was then cooled to ambient temperature. The reaction mixture was diluted with water (100 mL) and extracted with dichloromethane (3100 mL). Organic layer was dried over Na.sub.2SO.sub.4, filtered and evaporated completely to afford [4-(acetoxymethyl)-2-bromo-5-chloro-phenyl]methyl acetate (14.5 g 93% of theoretical yield)

[0211] 1H NMR (400 MHz, DMSO-d6) ppm 2.11 (d, J=4.4 Hz, 6H) 5.12 (d, J=13.05 Hz, 4H) 7.61 (s, 1H), 7.79 (s, 1H)

Example 9

Synthesis of [4-(acetoxymethyl)-2-bromo-5-chloro-phenyl]methyl acetate

[0212] ##STR00051##

[0213] To a stirred solution of [4-(acetoxymethyl)-2-bromo-5-chloro-phenyl]methyl acetate (14.5 g, 43.2 mmol) in 1,4 dioxane (140 mL) was added fused potassium acetate (12.9 g, 130 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (16.5 g, 64.8 mmol) and finally [1,1-Bis(diphenylphosphino) ferrocene]-dichloropalladium(II) dichloromethane adduct (1.8 g, 2.16 mmol) under nitrogen. The reaction mixture was heated at 100 C. for 3 h. The reaction mixture was cooled to ambient temperature and diluted with water (100 mL) and then extracted with ethyl acetate (3200 mL). Combined organic layer was washed with water (3200 mL) followed by brine wash (200 mL). Organic layer was dried over Na.sub.2SO.sub.4, filtered and evaporated completely to give crude compound. This crude product obtained was purified by flash chromatography using 10% ethyl acetate in hexane as eluent to afford desired compound [4-(acetoxymethyl)-2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl acetate (14 g, 84.7% of theoretical yield).

[0214] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 1.30 (s, 12H) 2.06 (d, J=2.01 Hz, 6H) 5.15 (s, 2H) 5.24 (s, 2H) 7.53 (s, 1H) 7.79 (s, 1H)

Example 10

Synthesis of (5-chloro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)methanol

[0215] ##STR00052##

[0216] To a stirred solution of [4-(acetoxymethyl)-2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl acetate (14 g, 36.59 mmol) in methanol (100 mL) was added 6N HCl (100 mL) in drops at 0 C. over a period of 20 min. Reaction mixture was then allowed to stir at ambient temperature for 12 h. The reaction mixture was diluted with water (100 mL) and then extracted with dichloromethane (3100 mL). Organic layer was dried over Na.sub.2SO.sub.4, filtered and evaporated completely to afford (5-chloro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)methanol (5.4 g, 80% of theoretical yield) as a semi solid.

[0217] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 4.60 (d, J=4.4 Hz, 2H), 4.97 (s, 2H), 5.41 (t, J=5.6 Hz, 1H) 7.48 (s, 1H), 7.94 (s, 1H), 9.29 (s, 1H)

Example 11

Synthesis of 5-chloro-1-hydroxy-3H-2,1-benzoxaborole-6-carbaldehyde

[0218] ##STR00053##

[0219] To a stirred solution of compound (5-chloro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)methanol (1 g, 5.04 mmol) in DCM (150 mL) was added Pyridinium dichromate (4 g, 10.08 mmol) and celite (20 g) at 0 C. in portions. Reaction mixture was then stirred at ambient temperature for 6 h. starting was consumed completely and was confirmed by TLC. Reaction mixture was then filtered through celite bed and bed was washed with DCM (50 mL). Filtrate was evaporated and crude obtained was purified by flash chromatography using 60% ethyl acetate in hexane as eluent to afford pure 5-chloro-1-hydroxy-3H-2, 1-benzoxaborole-6-carbaldehyde (0.63 g, 63.64% of theoretical yield) as a white solid.

[0220] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 5.06 (s, 2H), 7.71 (s, 1H), 8.26 (s, 1H), 9.53 (s, 1H), 10.39 (s, 1H)

Example 12

Synthesis of 1-(5-chloro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)-N-methoxy-methanimine

[0221] ##STR00054##

[0222] 5-chloro-1-hydroxy-3H-2,1-benzoxaborole-6-carbaldehyde (250 mg, 1.3 mmol) was mixed with O-methylhydroxylamine hydrochloride (450 mg, 5.1 mmol) and sodium acetate (420 mg, 5.1 mmol) in ethanol (8 ml). The reaction mixture was refluxed for 3 h. The solvent was removed under reduced pressure and the residue was diluted with ethyl acetate (50 ml). The organic phase was washed with water (120 ml), dried over magnesium sulphate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography using 5% Methanol in dichloromenthane as eluent to give 1-(5-chloro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)-N-methoxy-methanimine (270 mg, 94% of theoretical yield).

[0223] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 3.96 (d, J=2.51 Hz, 3H) 5.01 (s, 2H) 7.62 (s, 1H) 8.24 (s, 1H) 8.48 (s, 1H) 9.43 (s, 1H)

[0224] LCMS M+H 226.1 (RT; 1.75-1.82)

Example 13

Synthesis of 1-[(5-chloro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)methyleneamino]-3-methyl-thiourea

[0225] ##STR00055##

[0226] 5-chloro-1-hydroxy-3H-2,1-benzoxaborole-6-carbaldehyde (80 mg, 0.4 mmol) was mixed with 1-amino-3-methyl-thiourea (50 mg, 0.4 mmol) in methanol (4 ml). The reaction mixture was stirred at ambient temperature for 1 h. The solvent was removed under reduced pressure and the residue was diluted with ethyl acetate (50 ml). The organic phase was filtered to get 1-(5-chloro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)-N-methoxy-methanimine as white solid (80 mg, 70% of theoretical yield).

[0227] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 3.03 (d, J=4.52 Hz, 3H) 5.01 (s, 2H) 7.58 (s, 1H) 8.49 (s, 1H) 8.53 (s, J=9.40, 9.40 Hz, 2H) 9.33 (s, 1H) 11.67 (s, 1H)

[0228] LCMS M+H 284 (RT; 1.56-1.58)

Example 14

Synthesis of 1-(1-hydroxy-3H-2,1-benzoxaborol-7-yl)-N-methoxy-methanimine

[0229] ##STR00056##

[0230] 1-hydroxy-3H-2,1-benzoxaborole-7-carbaldehyde (100 mg, 0.6 mmol) was mixed with O-methylhydroxylamine hydrochloride (100 mg, 2 mmol) and sodium acetate (100 mg, 2 mmol) in methanol (10 ml). The reaction mixture was reflux overnight. The solvent was removed under reduced pressure and the residue was diluted with ethyl acetate (50 ml). The organic phase was washed with water (120 ml), dried over magnesium sulphate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography using 5% Methanol in dichloromenthane as eluent to give 1-(5-chloro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)-N-methoxy-methanimine (100 mg, 80% of theoretical yield).

[0231] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 3.93 (s, 3H) 5.04 (s, 2H) 7.45-7.56 (m, 2H) 7.69 (d, J=6.77 Hz, 1H) 8.53 (s, 1H) 9.12 (s, 1H)

[0232] LCMS M+H 191.9 (RT; 1.74-1.77)

Example 15

Synthesis of 1-[(1-hydroxy-3H-2,1-benzoxaborol-7-yl)methyleneamino]-3-methyl-thiourea

[0233] ##STR00057##

[0234] 1-hydroxy-3H-2,1-benzoxaborole-7-carbaldehyde (70 mg, 0.4322 mmol) was mixed with 1-amino-3-methyl-thiourea (45.5 mg, 0.4322 mmol) in methanol (4 ml). The reaction mixture was stirred at ambient temperature for 1 h. The precipitate formed during reaction was collected by filtration and washed with cyclohexane to afford 1-[(1-hydroxy-3H-2,1-benzoxaborol-7-yl)methyleneamino]-3-methyl-thiourea (107 mg, 83% of theoretical yield).

[0235] obtain white solid The solvent was removed under reduced pressure and the residue was diluted with ethyl acetate (50 ml). The organic phase was washed with water (120 ml), dried over magnesium sulphate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography using 5% Methanol in dichloromenthane as eluent to give 1-(5-chloro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)-N-methoxy-methanimine (100 mg, 80% of theoretical yield).

[0236] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 3.01 (d, J=4.52 Hz, 3H), 5.02 (s, 2H), 7.41 (d, J=7.53 Hz, 1H), 7.51 (t, J=7.65 Hz, 1H), 8.03 (d, J=7.53 Hz, 1H), 8.46 (s, 1H), 8.67 (m, 1H), 9.28 (s, 1H) 11.61 (s, 1H)

[0237] LCMS M+H 250 (RT; 1.47-1.51)

Example 16

Synthesis of 1-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)-N-methoxy-methanimine

[0238] ##STR00058##

[0239] 1-hydroxy-3H-2,1-benzoxaborole-5-carbaldehyde (100 mg, 0.62 mmol) was mixed with O-methylhydroxylamine hydrochloride (220 mg, 2.5 mmol) and sodium acetate (200 mg, 2.5 mmol) in ethanol (10 ml). The reaction mixture was reflux for 3 h. The solvent was removed under reduced pressure and the residue was diluted with ethyl acetate (50 ml). The organic phase was washed with water (120 ml), dried over sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography using 5% Methanol in dichloromenthane as eluent to afford 1-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)-N-methoxy-methanimine (60 mg, 50% of theoretical yield).

[0240] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 3.91 (s, 3H) 5.01 (s, 2H) 7.59 (s, 1H) 7.54-7.54 (m, 1H) 7.61-7.67 (m, 1H) 7.75 (d, J=7.53 Hz, 1H) 8.29 (s, 1H) 9.27 (s, 1H)

[0241] LCMS M+H 192 (RT; 1.52-1.59)

Example 17

Synthesis of 1-(1-hydroxy-3H-2,1-benzoxaborol-4-yl)-N-methoxy-methanimine

[0242] ##STR00059##

[0243] 1-hydroxy-3H-2,1-benzoxaborole-4-carbaldehyde (80 mg, 0.5 mmol) was mixed with O-methylhydroxylamine hydrochloride (200 mg, 2 mmol) and sodium acetate (200 mg, 2 mmol) in ethanol (8 ml). The reaction mixture was reflux for 3 h. The solvent was removed under reduced pressure and the residue was diluted with ethyl acetate (50 ml). The organic phase was washed with water (120 ml), dried over sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography using 50% ethyl acetate in hexane as eluent to afford 1-(1-hydroxy-3H-2,1-benzoxaborol-4-yl)-N-methoxy-methanimine (70 mg, 70% of theoretical yield).

[0244] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 3.92 (s, 3H) 5.08 (s, 2H) 7.45 (t, J=7.42 Hz, 1H) 7.64 (d, J=7.35 Hz, 1H) 7.79 (dd, J=7.28, 1.00 Hz, 1H) 8.33 (s, 1H) 9.26 (s, 1H)

[0245] LCMS M+H 192.1 (RT; 1.58-1.64)

[0246] The following tables illustrate the invention:

[0247] The A1 to A4 have the meaning as follows:

##STR00060##

TABLE-US-00001 TABLE T2 R2.001 [00061] embedded image R2.002 [00062] R2.003 NNHC(S)NHPh R2.004 NNHC(S)NHCH.sub.2Ph R2.005 [00063] R2.006 NNHCH.sub.2C(O)OEt R2.007 NNHC(O)-4-ClPh R2.008 NNHC(O)-4-NO.sub.2Ph R2.009 [00064] R2.010 NNHC(O)NHPh R2.011 NNHC(O)-3-pyridyl R2.012 NNHC(O)-2,5-ClPh R2.013 [00065] R2.014 NNHC(O)-2-NO.sub.2Ph R2.015 NNH-2,4-ClPh R2.016 NNH-4-MePh R2.017 NNH-2,4-FPh R2.018 [00066] embedded image R2.019 NNHC(O)OEt R2.020 NNHC(O)NH-2,4-Ph R2.021 [00067] R2.022 NNHC(O)NH-4-OMePh R2.023 NNH-2,5-FPh R2.024 NNH-2-NO.sub.2Ph R2.025 [00068] R2.026 NNH-3,5-ClPh R2.027 [00069] R2.028 [00070] R2.029 [00071] R2.030 [00072] R2.031 NNHCH(CH.sub.3).sub.2 R2.032 [00073] R2.033 NNH-2,6-Cl-4-CF.sub.3Ph R2.034 [00074] embedded image R2.035 [00075] R2.036 NNH-4-ClPh R2.037 NNH-3-NO.sub.2Ph R2.038 NNH-4-CF.sub.3Ph R2.039 NNH-2,6-ClPh R2.040 [00076] R2.041 NNHC(S)NHCH.sub.2Ph R2.042 [00077] R2.043 [00078] R2.044 [00079] R2.045 NNHCH.sub.2Ph R2.046 NNHCH.sub.2OC(O)CH.sub.2CH.sub.3 R2.047 NNH-4-OCH.sub.3Ph R2.048 [00080] embedded image R2.049 NNHC(S)NHCH.sub.2CH.sub.3 R2.051 [00081] R2.052 NNHC(S)NH.sub.2 R2.053 NNHC(S)NHMe R2.054 NOCH.sub.3CHCHCl R2.055 NNHC(S)NHCH.sub.2CHCH.sub.2 R2.056 NOC(CH.sub.3).sub.3 R2.057 [00082] R2.058 NOCH.sub.2-4-ClPh R2.059 NOCH.sub.2-2-FPh R2.060 NOCH.sub.2-4-NO.sub.2Ph R2.061 NO(CH.sub.2).sub.5CH.sub.3 R2.062 NO(CH.sub.2).sub.3CH.sub.3 R2.063 [00083] embedded image R2.064 [00084] R2.065 [00085] R2.066 NOCH.sub.2CHC(CH.sub.3).sub.2 R2.067 [00086] R2.068 NOCH.sub.2-2,6-ClPh R2.069 [00087] R2.070 NOCH.sub.2-2,3,4,5,6-FPh R2.071 NOCH(CH.sub.3).sub.2 R2.072 NOCH.sub.2CH.sub.3 R2.073 NOCH.sub.2CHCH R2.074 [00088] R2.075 [00089] R2.076 NO(CH.sub.2).sub.2CH.sub.3 R2.077 NO(CH.sub.2).sub.2CH.sub.2C(O)OH R2.078 NO-4-CNPh R2.079 NOCH.sub.2-2,4-ClPh R2.080 NOCH.sub.2-4-MePh R2.081 NOCH.sub.2-2-Cl-4-FPh R2.082 [00090] embedded image R2.083 [00091] R2.084 [00092] R2.085 [00093] R2.086 NOCH.sub.2CH(CH.sub.3).sub.2 R2.087 NO-4-NO.sub.2Ph R2.088 [00094] R2.089 NO(CH.sub.2).sub.11CH.sub.3 R2.090 NOCH.sub.2-2,4,5-ClPh R2.091 NO(CH.sub.2).sub.3C(O)OCH.sub.2CH.sub.3 R2.092 [00095] R2.093 NOH R2.094 NNH.sub.2 R2.095 [00096] embedded image R2.096 [00097] R2.097 [00098] R2.098 [00099] R2.099 [00100] R2.100 [00101] R2.101 [00102] R2.102 [00103] R2.103 [00104] R2.104 [00105] R2.105 [00106] R2.106 [00107] R2.107 [00108] R2.108 [00109] R2.109 [00110] R2.110 [00111] R2.111 [00112] R2.112 [00113] R2.113 [00114] R2.114 NN(CH.sub.3).sub.2 R2.115 NN(CH.sub.3)CH.sub.2CH.sub.3 R2.116 NN(CH.sub.3)(CH.sub.2).sub.2CH.sub.3 R2.117 NN(CH.sub.3)(CH.sub.2).sub.3CH.sub.3 R2.118 NN(CH.sub.3)(CH.sub.2).sub.4CH.sub.3 R2.119 NN(CH.sub.3)(CH.sub.2).sub.5CH.sub.3 R2.120 NN(CH.sub.3)CH(CH.sub.3).sub.2 R2.121 NN(CH.sub.3)C(CH.sub.3).sub.3 R2.122 NN(CH.sub.3)CH.sub.2CH(CH.sub.3).sub.2 R2.123 NN(CH.sub.3)CH.sub.2C(CH.sub.3).sub.3 R2.124 NN(CH.sub.3)Ph R2.125 NN(CH.sub.3)-4-FPh R2.126 NN(CH.sub.3)-4-ClPh R2.127 NN(CH.sub.3)-2,4-FPh R2.128 NN(CH.sub.3)-2,4-ClPh R2.129 NN(CH.sub.3)CH.sub.2Ph R2.130 NN(CH.sub.3)CH.sub.2-4-FPh R2.131 NN(CH.sub.3)CH.sub.2-4-ClPh R2.132 NN(CH.sub.3)CH.sub.2-2,4-FPh R2.133 NN(CH.sub.3)CH.sub.2-2,5-FPh R2.134 NN(CH.sub.3)CH.sub.2-2,6-FPh R2.135 NN(CH.sub.3)CH.sub.2-3,5-FPh R2.136 NN(CH.sub.3)CH.sub.2-2,4,6-FPh R2.137 NN(CH.sub.3)CH.sub.2-2,4-ClPh R2.138 NN(CH.sub.3)CH.sub.2-2,5-ClPh R2.139 NN(CH.sub.3)CH.sub.2-2,6-ClPh R2.140 NN(CH.sub.3)CH.sub.2-3,5-ClPh R2.141 NN(CH.sub.3)CH.sub.2-2,4,6-ClPh R2.142 [00115] embedded image R2.143 [00116] R2.144 [00117] R2.145 [00118] R2.146 [00119] R2.147 [00120] R2.148 [00121] R2.149 [00122] R2.150 [00123] R2.151 [00124] R2.152 [00125] R2.153 [00126] R2.154 [00127] R2.155 [00128] R2.156 [00129] R2.157 [00130] R2.158 [00131] R2.159 [00132] R2.160 [00133] R2.161 [00134] R2.162 [00135] embedded image R2.163 [00136] R2.164 [00137] R2.165 [00138] R2.166 [00139] R2.167 [00140] R2.168 [00141] R2.169 [00142] R2.170 [00143] R2.171 [00144] R2.172 [00145] R2.173 [00146] R2.174 [00147] R2.175 [00148] R2.176 [00149] R2.177 [00150] R2.178 [00151] R2.179 [00152] R2.180 NOCH.sub.2Ph R2.181 NOCH.sub.3 R2.182 O R2.183 NNHC(O)OMe

TABLE-US-00002 TABLE T4 No. R.sup.3 1 Me 2 4-ClPh 3 4-FPh 4 2,4-ClPh 5 4-OMePh 6 4-MePh 7 acetylene 8 cyclopropyl 9 vinyl 10 Allyl 11 Ph 12 H

[0248] Table 1: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Me, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0249] Table 2: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Me, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 and R2.0183 of Table T2.

[0250] Table 3: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Me, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0251] Table 4: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Me, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0252] Table 5: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Me, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0253] Table 6: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Me, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0254] Table 7: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Me, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0255] Table 8: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Me, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0256] Table 9: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Me, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0257] Table 10: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Me, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0258] Table 11: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Me, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0259] Table 12: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Me, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0260] Table 13: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0261] Table 14: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0262] Table 15: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0263] Table 16: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0264] Table 17: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0265] Table 18: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0266] Table 19: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0267] Table 20: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0268] Table 21: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0269] Table 22: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0270] Table 23: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0271] Table 24: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0272] Table 25: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is F, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0273] Table 26: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is F, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0274] Table 27: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is F, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0275] Table 28: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is F, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0276] Table 29: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is F, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0277] Table 30: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is F, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0278] Table 31: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is F, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0279] Table 32: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is F, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0280] Table 33: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is F, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0281] Table 34: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is F, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0282] Table 35: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is F, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0283] Table 36: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is F, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0284] Table 37: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0285] Table 38: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0286] Table 39: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0287] Table 40: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0288] Table 41: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0289] Table 42: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0290] Table 43: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0291] Table 44: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0292] Table 45: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0293] Table 46: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0294] Table 47: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0295] Table 48: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0296] Table 49: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0297] Table 50: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0298] Table 51: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0299] Table 52: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0300] Table 53: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0301] Table 54: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0302] Table 55: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0303] Table 56: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0304] Table 57: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0305] Table 58: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0306] Table 59: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0307] Table 60: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0308] Table 61: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CN, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0309] Table 62: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CN, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0310] Table 63: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CN, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0311] Table 64: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CN, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0312] Table 65: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CN, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0313] Table 66: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CN, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0314] Table 67: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CN, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0315] Table 68: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CN, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0316] Table 69: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CN, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0317] Table 70: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CN, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0318] Table 71: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CN, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0319] Table 72: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is CN, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0320] Table 73: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0321] Table 74: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0322] Table 75: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0323] Table 76: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0324] Table 77: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0325] Table 78: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0326] Table 79: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0327] Table 80: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0328] Table 81: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0329] Table 82: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0330] Table 83: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0331] Table 84: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0332] Table 85: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is H, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0333] Table 86: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is H, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0334] Table 87: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is H, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0335] Table 88: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is H, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0336] Table 89: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is H, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0337] Table 90: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is H, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0338] Table 91: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is H, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0339] Table 92: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is H, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0340] Table 93: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is H, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0341] Table 94: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is H, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0342] Table 95: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is H, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0343] Table 96: This table discloses the 183 specific compounds of the formula A1 wherein R.sup.1 is H, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0344] Table 97: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Me, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0345] Table 98: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Me, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0346] Table 99: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Me, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0347] Table 100: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Me, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0348] Table 101: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Me, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0349] Table 102: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Me, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0350] Table 103: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Me, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0351] Table 104: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Me, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0352] Table 105: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Me, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0353] Table 106: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Me, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0354] Table 107: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Me, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0355] Table 108: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Me, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0356] Table 109: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0357] Table 110: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0358] Table 111: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0359] Table 112: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0360] Table 113: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0361] Table 114: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0362] Table 115: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0363] Table 116: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0364] Table 117: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0365] Table 118: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0366] Table 119: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0367] Table 120: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0368] Table 121: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is F, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0369] Table 122: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is F, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0370] Table 123: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is F, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0371] Table 124: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is F, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0372] Table 125: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is F, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0373] Table 126: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is F, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0374] Table 127: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is F, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0375] Table 128: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is F, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0376] Table 129: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is F, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0377] Table 130: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is F, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0378] Table 131: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is F, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0379] Table 132: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is F, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0380] Table 133: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0381] Table 134: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0382] Table 135: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0383] Table 136: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0384] Table 137: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0385] Table 138: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0386] Table 139: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0387] Table 140: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0388] Table 141: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0389] Table 142: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0390] Table 143: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0391] Table 144: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0392] Table 145: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0393] Table 146: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0394] Table 147: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0395] Table 148: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0396] Table 149: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0397] Table 150: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0398] Table 151: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0399] Table 152: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0400] Table 153: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0401] Table 154: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0402] Table 155: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0403] Table 156: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0404] Table 157: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CN, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0405] Table 158: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CN, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0406] Table 159: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CN, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0407] Table 160: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CN, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0408] Table 161: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CN, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0409] Table 162: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CN, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0410] Table 163: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CN, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0411] Table 164: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CN, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0412] Table 165: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CN, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0413] Table 166: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CN, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0414] Table 167: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CN, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0415] Table 168: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is CN, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0416] Table 169: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0417] Table 170: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0418] Table 171: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0419] Table 172: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0420] Table 173: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0421] Table 174: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0422] Table 175: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0423] Table 176: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0424] Table 177: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0425] Table 178: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0426] Table 179: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0427] Table 180: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0428] Table 181: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is H, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0429] Table 182: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is H, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0430] Table 183: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is H, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0431] Table 184: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is H, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0432] Table 185: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is H, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0433] Table 186: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is H, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0434] Table 187: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is H, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0435] Table 188: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is H, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0436] Table 189: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is H, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0437] Table 190: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is H, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0438] Table 191: This table discloses the 183 specific compounds of the formula A2 wherein R.sup.1 is H, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0439] Table 192: This table discloses the 179 specific compounds of the formula A2 wherein R.sup.1 is H, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 179 lines R2.001 to R2.0179 of Table T2.

[0440] Table 193: This table discloses the 183 specific compounds of the formula A3 wherein R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0441] Table 194: This table discloses the 183 specific compounds of the formula A3 wherein R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0442] Table 195: This table discloses the 183 specific compounds of the formula A3 wherein R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0443] Table 196: This table discloses the 183 specific compounds of the formula A3 wherein R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0444] Table 197: This table discloses the 183 specific compounds of the formula A3 wherein R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0445] Table 198: This table discloses the 183 specific compounds of the formula A3 wherein R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0446] Table 199: This table discloses the 183 specific compounds of the formula A3 wherein R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0447] Table 200: This table discloses the 183 specific compounds of the formula A3 wherein R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0448] Table 201: This table discloses the 183 specific compounds of the formula A3 wherein R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0449] Table 202: This table discloses the 183 specific compounds of the formula A3 wherein R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0450] Table 203: This table discloses the 183 specific compounds of the formula A3 wherein R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0451] Table 204: This table discloses the 183 specific compounds of the formula A3 wherein R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0452] Table 205: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Me, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0453] Table 206: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Me, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0454] Table 207: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Me, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0455] Table 208: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Me, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0456] Table 209: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Me, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0457] Table 210: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Me, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0458] Table 211: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Me, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0459] Table 212: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Me, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0460] Table 213: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Me, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0461] Table 214: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Me, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0462] Table 215: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Me, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0463] Table 216: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Me, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0464] Table 217: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0465] Table 218: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0466] Table 219: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0467] Table 220: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0468] Table 221: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0469] Table 222: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0470] Table 223: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0471] Table 224: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0472] Table 225: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0473] Table 226: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0474] Table 227: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0475] Table 228: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CF3, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0476] Table 229: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is F, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0477] Table 230: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is F, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0478] Table 231: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is F, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0479] Table 232: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is F, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0480] Table 233: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is F, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0481] Table 234: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is F, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0482] Table 235: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is F, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0483] Table 236: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is F, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0484] Table 237: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is F, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0485] Table 238: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is F, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0486] Table 239: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is F, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0487] Table 240: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is F, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0488] Table 241: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0489] Table 242: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0490] Table 243: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0491] Table 244: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0492] Table 245: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0493] Table 246: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0494] Table 247: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0495] Table 248: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0496] Table 249: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0497] Table 250: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0498] Table 251: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0499] Table 252: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Cl, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0500] Table 253: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0501] Table 254: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0502] Table 255: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0503] Table 256: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0504] Table 257: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0505] Table 258: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0506] Table 259: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0507] Table 260: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0508] Table 261: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0509] Table 262: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0510] Table 263: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0511] Table 264: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is Nitro, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0512] Table 265: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CN, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0513] Table 266: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CN, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0514] Table 267: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CN, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0515] Table 268: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CN, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0516] Table 269: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CN, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0517] Table 270: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CN, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0518] Table 271: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CN, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0519] Table 272: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CN, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0520] Table 273: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CN, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0521] Table 274: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CN, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0522] Table 275: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CN, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0523] Table 276: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is CN, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0524] Table 277: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0525] Table 278: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0526] Table 279: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0527] Table 280: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0528] Table 281: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0529] Table 282: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0530] Table 283: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0531] Table 284: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0532] Table 285: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0533] Table 286: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0534] Table 287: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0535] Table 288: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is OMe, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0536] Table 289: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is H, R.sup.3 is as defined in line 1 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0537] Table 290: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is H, R.sup.3 is as defined in line 2 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0538] Table 291: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is H, R.sup.3 is as defined in line 3 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0539] Table 292: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is H, R.sup.3 is as defined in line 4 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0540] Table 293: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is H, R.sup.3 is as defined in line 5 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0541] Table 294: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is H, R.sup.3 is as defined in line 6 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0542] Table 295: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is H, R.sup.3 is as defined in line 7 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0543] Table 296: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is H, R.sup.3 is as defined in line 8 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0544] Table 297: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is H, R.sup.3 is as defined in line 9 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0545] Table 298: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is H, R.sup.3 is as defined in line 10 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0546] Table 299: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is H, R.sup.3 is as defined in line 11 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line appropriately selected from the 183 lines R2.001 to R2.0183 of Table T2.

[0547] Table 300: This table discloses the 183 specific compounds of the formula A4 wherein R.sup.1 is H, R.sup.3 is as defined in line 12 of Table T4 and R.sup.2 has the specific meaning given in the corresponding line

TABLE-US-00003 Table of selected examples: Table T1 Cpd. CN MS Rt M.P No. A R.sup.1 R.sup.2 R.sup.3 Geometry [M + H].sup.+ (min) LCMSmethod ( C.) 1H-NMR data: ppm (multiplicity/number of Hs) 1 A1 Cl R2.007 H E or Z 348.94 1.34 M1 2 A1 Cl R2.008 H E or Z 359.96 1.22 M1 3 A1 Cl R2.009 H E or Z 365.98 1.48 M1 4 A1 Cl R2.010 H E or Z 329.96 1.26 M1 5 A1 Cl R2.011 H E or Z 315.93 0.89 M1 6 A1 Cl R2.012 H E or Z 382.87 1.35 M1 7 A1 Cl R2.013 H E or Z 321.93 1.48 M1 8 A1 Cl R2.014 H E or Z 359.97 1.1 M1 9 A1 Cl R2.015 H E or Z 354.9 1.87 M1 10 A1 Cl R2.016 H E or Z 300.98 1.6 M1 11 A1 Cl R2.017 H E or Z 322.98 1.61 M1 12 A1 Cl R2.018 H E or Z 327.94 1.29 M1 13 A1 Cl R2.019 H E or Z 282.96 1.07 M1 14 A1 Cl R2.020 H E or Z 350.94 1.24 M1 15 A1 Cl R2.021 H E or Z 281.95 0.79 M1 16 A1 Cl R2.022 H E or Z 344.96 1.22 M1 17 A1 Cl R2.023 H E or Z 322.94 1.61 M1 18 A1 Cl R2.024 H E or Z 321.9 1.64 M1 19 A1 Cl R2.025 H E or Z 349.93 1.14 M1 20 A1 Cl R2.026 H E or Z 354.9 1.82 M1 21 A1 Cl R2.027 H E or Z 323.92 1.13 M1 22 A1 Cl R2.028 H E or Z 278.96 1 M1 23 A1 Cl R2.029 H E or Z 372.96 1.72 M1 24 A1 Cl R2.030 H E or Z 321.91 1.18 M1 25 A1 Cl R2.031 H E or Z 252.99 1.24 M1 26 A1 Cl R2.032 H E or Z 383.87 1.37 M1 27 A1 Cl R2.033 H E or Z 422.87 1.93 M1 28 A1 Cl R2.034 H E or Z 389.91 1.58 M1 29 A1 Cl R2.035 H E or Z 421.9 1.46 M1 30 A1 Cl R2.036 H E or Z 320.91 1.63 M1 31 A1 Cl R2.037 H E or Z 332.1 1.53 M1 32 A1 Cl R2.038 H E or Z 354.97 1.7 M1 33 A1 Cl R2.039 H E or Z 354.9 1.67 M1 34 A1 Cl R2.040 H E or Z 386.95 1.15 M1 35 A1 Cl R2.003 H E or Z 345 1.83-1.89 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.02 (s, 2 H) 5.11 (s, 1 H) 7.19-7.26 (m, 1 H) 7.33-7.43 (m, 2 H) 7.50-7.65 (m, 3 H) 8.60-8.70 (m, 2 H) 9.32 (s, 1 H) 10.18 (s, 1 H) 10.32 (s, 1 H) 11.94-12.07 (m, 1 H) 36 A1 Cl R2.055 H E or Z 310 1.71-1.73 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.10 (d, J = 5.27 Hz, 1 H) 5.01 (s, 2 H) 5.05-5.22 (m, 2 H) 5.83-6.00 (m, 1 H) 7.58 (s, 1 H) 8.49 (s, 1 H) 8.54-8.57 (m, 1 H) 8.72 (t, J = 5.90 Hz, 1 H) 9.35 (s, 1 H) 11.71 (s, 1 H) 37 A1 Cl R2.041 H E or Z 373.99 1.51 M1 38 A1 Cl R2.042 H E or Z 352 1.53 M1 39 A1 Cl R2.054 H E 285.92 1.58 M1 40 A1 Cl R2.180 H E or Z 302.02 1.67 M1 41 A1 Cl R2.056 H E or Z 268.06 1.7 M1 42 A1 Cl R2.057 H E or Z 295.97 1.49 M1 43 A1 Cl R2.058 H E or Z 335.92 1.8 M1 44 A1 Cl R2.059 H E or Z 319.98 1.68 M1 45 A1 Cl R2.060 H E or Z 346.98 1.64 M1 46 A1 Cl R2.061 H E or Z 296 1.97 M1 47 A1 Cl R2.062 H E or Z 268.02 1.72 M1 48 A1 Cl R2.063 H E or Z 286 1.57 M1 49 A1 Cl R2.064 H E 299.94 1.7 M1 50 A1 Cl R2.065 H E or Z 319.73 1.75 M1 51 A1 Cl R2.066 H E or Z 280.07 1.7 M1 52 A1 Cl R2.067 H E or Z 311.98 1.46 M1 53 A1 Cl R2.068 H E or Z 369.89 1.86 M1 54 A1 Cl R2.069 H E or Z 374.01 1.66 M1 55 A1 Cl R2.070 H E or Z 391.79 1.83 M1 56 A1 Cl R2.071 H E or Z 254.01 1.56 M1 57 A1 Cl R2.072 H E or Z 240.01 1.41 M1 58 A1 Cl R2.073 H E or Z 252.01 1.47 M1 59 A1 Cl R2.075 H E or Z 373.98 1.38 M1 60 A1 Cl R2.074 H E or Z 359.96 1.6 M1 61 A1 Cl R2.076 H E or Z 254.03 1.58 M1 62 A1 Cl R2.077 H E or Z 297.95 1.16 M1 63 A1 Cl R2.078 H E or Z 312.99 1.62 M1 64 A1 Cl R2.079 H E or Z 369.98 1.97 M1 65 A1 Cl R2.080 H E or Z 316 1.78 M1 66 A1 Cl R2.081 H E or Z 353.87 1.83 M1 67 A1 Cl R2.082 H E or Z 383.85 2.06 M1 68 A1 Cl R2.083 H E or Z 384.25 2.02 M1 69 A1 Cl R2.084 H Z 372.18 1.97 M1 70 A1 Cl R2.006 H E or Z 297 1.66-1.69 M2 1H NMR (400 MHz, DMSO-d6) ppm 1.20 (t, J = 7.03 Hz, 4 H) 4.02 (d, J = 5.27 Hz, 2 H) 4.96 (s, 2 H) 7.49 (s, 1 H) 7.99 (s, 1 H) 7.99-8.02 (m, 1 H) 8.19 (s, 1 H) 9.33 (s, 1 H) 71 A1 Cl R2.181 H E or Z 225.9 1.72-1.79 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.95 (s, 3 H) 5.01 (s, 2 H) 7.62 (s, 1 H) 8.24 (s, 1 H) 8.48 (s, 1 H) 9.42 (s, 1 H) 72 A1 Cl R2.053 H E or Z 284 1.56-1.58 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.03 (d, J = 4.52 Hz, 3 H) 5.01 (s, 2 H) 7.58 (s, 1 H) 8.47-8.59 (m, 3 H) 9.33 (s, 1 H) 11.67 (s, 1 H) 73 A1 Cl R2.004 H E or Z 360 1.88-1.91 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.86 (d, J = 6.02 Hz, 2 H) 5.01 (s, 2 H) 7.22-7.37 (m, 5 H) 7.58 (s, 1 H) 8.49 (s, 1 H) 8.59 (s, 1 H) 9.15 (t, J = 6.18 Hz, 1 H) 9.32 (s, 1 H) 11.78 (s, 1 H) 74 A1 Cl R2.093 H E or Z 211.9 1.44-1.49 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.00 (s, 2 H) 7.60 (s, 1 H) 8.22 (s, 1 H) 8.41 (s, 1 H) 9.42 (s, 1 H) 11.63 (s, 1 H) 75 A1 Cl R2.005 H E or Z 308 1.47-1.49 M2 1H NMR (400 MHz, DMSO-d6) ppm) 5.02 (s, 3 H) 6.60 (s, 2 H) 7.61 (s, 1 H) 8.35 (s, 1 H) 8.61 (s, 1 H) 76 A1 Cl R2.052 H E or Z 270 1.41-1.43 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.01 (s, 2 H) 7.57 (s, 1 H) 7.95 (br. s., 1 H) 8.34 (br. s., 1 H) 8.49 (s, 1 H) 8.53 (s, 1 H) 9.29 (s, 1 H) 11.64 (s, 1 H) 77 A1 F R2.007 H E or Z 332.95 1.23 M1 78 A1 F R2.008 H E or Z 343.96 1.12 M1 79 A1 F R2.009 H E or Z 349.97 1.37 M1 80 A1 F R2.010 H E or Z 314.02 1.17 M1 81 A1 F R2.011 H E or Z 299.94 0.78 M1 82 A1 F R2.043 H E or Z 397 1.83 M1 83 A1 F R2.012 H E or Z 366.9 1.25 M1 84 A1 F R2.044 H E or Z 411 1.81 M1 85 A1 F R2.013 H E or Z 305.95 1.38 M1 86 A1 F R2.014 H E or Z 343.97 1 M1 87 A1 F R2.015 H E or Z 338.93 1.77 M1 88 A1 F R2.016 H E or Z 285.02 1.5 M1 89 A1 F R2.017 H E or Z 306.98 1.5 M1 90 A1 F R2.018 H E or Z 311.96 1.19 M1 91 A1 F R2.019 H E or Z 266.98 0.94 M1 92 A1 F R2.020 H E or Z 334.94 1.13 M1 93 A1 F R2.021 H E or Z 266 0.68 M1 94 A1 F R2.045 H E or Z 284.98 1.35 M1 95 A1 F R2.022 H E or Z 328.95 1.11 M1 96 A1 F R2.023 H E or Z 306.97 1.51 M1 97 A1 F R2.024 H E or Z 316.1 1.53 M1 98 A1 F R2.025 H E or Z 333.94 1.03 M1 99 A1 F R2.026 H E or Z 338.96 1.74 M1 100 A1 F R2.027 H E or Z 307.95 1.03 M1 101 A1 F R2.028 H E or Z 262.98 0.89 M1 102 A1 F R2.029 H E or Z 356.97 1.63 M1 103 A1 F R2.030 H E or Z 305.89 1.06 M1 104 A1 F R2.046 H E or Z 280.98 1.03 M1 105 A1 F R2.031 H E or Z 236.99 1.05 M1 106 A1 F R2.032 H E or Z 367.9 1.26 M1 107 A1 F R2.047 H E or Z 301.04 1.35 M1 108 A1 F R2.033 H E or Z 406.89 1.83 M1 109 A1 F R2.048 H E or Z 388.93 1.5 M1 110 A1 F R2.034 H E or Z 373.9 1.48 M1 111 A1 F R2.035 H E or Z 405.94 1.36 M1 112 A1 F R2.036 H E or Z 304.98 1.54 M1 113 A1 F R2.037 H E or Z 315.87 1.43 M1 114 A1 F R2.038 H E or Z 338.98 1.61 M1 115 A1 F R2.039 H E or Z 338.91 1.56 M1 116 A1 F R2.040 H E or Z 370.95 1.05 M1 117 A1 F R2.003 H E or Z 330 1.77-1.81 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.02 (s, 2 H) 7.17-7.27 (m, 1 H) 7.33-7.42 (m, 3 H) 7.57 (d, J = 7.76 Hz, 2 H) 8.43 (s, 1 H) 8.58 (d, J = 7.53 Hz, 1 H) 9.25 (s, 1 H) 10.16 (s, 1 H) 11.94 (s, 1 H) 118 A1 F R2.055 H E or Z 293.98 1.12 M1 119 A1 F R2.041 H E or Z 358 1.43 M1 120 A1 F R2.042 H E or Z 336 1.44 M1 121 A1 F R2.056 H E or Z 251.82 1.04 M1 122 A1 F R2.057 H E or Z 280.09 1.34 M1 123 A1 F R2.058 H E or Z 319.96 1.68 M1 124 A1 F R2.059 H E or Z 304.02 1.55 M1 125 A1 F R2.060 H E or Z 331.01 1.51 M1 126 A1 F R2.061 H E or Z 280.09 1.84 M1 127 A1 F R2.062 H E or Z 252.08 1.58 M1 128 A1 F R2.063 H E or Z 269.99 1.44 M1 129 A1 F R2.085 H E or Z 268.07 0.98 M1 130 A1 F R2.064 H E 283.98 1.56 M1 131 A1 F R2.065 H E or Z 303.79 1.61 M1 132 A1 F R2.054 H Z 270.01 1.44 M1 133 A1 F R2.067 H E or Z 296.08 1.33 M1 134 A1 F R2.068 H E or Z 353.98 1.74 M1 135 A1 F R2.069 H E or Z 358.06 1.55 M1 136 A1 F R2.086 H E or Z 252.08 1.58 M1 137 A1 F R2.070 H E or Z 376.02 1.72 M1 138 A1 F R2.071 H E or Z 238.06 1.42 M1 139 A1 F R2.072 H E or Z 224.04 1.26 M1 140 A1 F R2.181 H E or Z 210.03 1.09 M1 141 A1 F R2.073 H E or Z 236.05 1.32 M1 142 A1 F R2.180 H E or Z 286.03 1.54 M1 143 A1 F R2.074 H E or Z 358.06 1.49 M1 144 A1 F R2.076 H E or Z 238.03 1.43 M1 145 A1 F R2.077 H E or Z 282.04 1.03 M1 146 A1 F R2.087 H E or Z 316.94 1.57 M1 147 A1 F R2.078 H E or Z 297.04 1.48 M1 148 A1 F R2.079 H E or Z 354.03 1.76 M1 149 A1 F R2.080 H E or Z 300.05 1.66 M1 150 A1 F R2.081 H E or Z 337.93 1.71 M1 151 A1 F R2.082 H E or Z 367.88 1.94 M1 152 A1 F R2.083 H E or Z 367.98 1.9 M1 153 A1 F R2.084 H Z 355.99 1.85 M1 154 A1 F R2.088 H E or Z 370.03 1.48 M1 155 A1 F R2.053 H E or Z 268 1.45-1.48 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.01 (s, 1 H) 5.10 (s, 1 H) 7.31 (s, 1 H) 7.34 (s, J = 11.52 Hz, 1 H) 8.30 (d, J = 6.65 Hz, 1 H) 8.31 (s, 1 H) 8.45 (d, J = 7.53 Hz, 2 H) 9.25 (s, 1 H) 11.59 (d, J = 4.03 Hz, 1 H) 11.59 (s, 1 H) 156 A1 F R2.052 H E or Z 254 1.31-1.33 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.01 (s, 2 H) 5.09 (s, 1 H) 7.31 (s, 1 H) 7.34 (s, J = 10.45 Hz, 1 H) 7.93 (br. s., 1 H) 8.22-8.35 (m, 2 H) 8.45 (d, J = 7.53 Hz, 1 H) 9.21 (s, 1 H) 11.57 (s, 1 H) 157 A2 Cl R2.007 H E or Z 348.9 1.51 M1 158 A2 Cl R2.009 H E or Z 366 1.65 M1 159 A2 Cl R2.051 H E or Z 371.89 1.06 M1 160 A2 Cl R2.011 H E or Z 315.92 1.08 M1 161 A2 Cl R2.012 H E or Z 382.89 1.53 M1 162 A2 Cl R2.013 H E or Z 321.92 1.57 M1 163 A2 Cl R2.014 H E or Z 359.95 1.27 M1 164 A2 Cl R2.015 H E or Z 354.89 2.02 M1 165 A2 Cl R2.017 H E or Z 322.96 1.76 M1 166 A2 Cl R2.018 H E or Z 328 1.48 M1 167 A2 Cl R2.019 H E or Z 282.97 1.26 M1 168 A2 Cl R2.020 H E or Z 350.95 1.42 M1 169 A2 Cl R2.045 H E or Z 300.96 1.56 M1 170 A2 Cl R2.022 H E or Z 344.97 1.39 M1 171 A2 Cl R2.023 H E or Z 322.97 1.77 M1 172 A2 Cl R2.024 H E or Z 332 1.81 M1 173 A2 Cl R2.026 H E or Z 354.9 2.03 M1 174 A2 Cl R2.028 H E or Z 278.99 1.15 M1 175 A2 Cl R2.029 H E or Z 372.96 1.9 M1 176 A2 Cl R2.030 H E or Z 321.88 1.42 M1 177 A2 Cl R2.046 H E or Z 296.96 1.28 M1 178 A2 Cl R2.031 H E or Z 252.97 1.47 M1 179 A2 Cl R2.047 H E or Z 316.96 1.42 M1 180 A2 Cl R2.033 H E or Z 422.87 1.84 M1 181 A2 Cl R2.034 H E or Z 389.91 1.81 M1 182 A2 Cl R2.035 H E or Z 421.89 1.63 M1 183 A2 Cl R2.036 H E or Z 320.9 1.83 M1 184 A2 Cl R2.037 H E or Z 332 1 M1 185 A2 Cl R2.038 H E or Z 354.96 1.89 M1 186 A2 Cl R2.003 H E or Z 345.9 1.97-2.01 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.03 (s, 2 H) 7.14-7.30 (m, 1 H) 7.32-7.44 (m, 2 H) 7.47-7.61 (m, 3 H) 8.29 (s, 1 H) 8.54 (s, 1 H) 9.42 (s, 1 H) 10.35 (s, 1 H) 12.03 (s, 1 H) 187 A2 Cl R2.055 H E or Z 309.97 1.38 M1 188 A2 Cl R2.041 H E or Z 373.99 1.66 M1 189 A2 Cl R2.054 H E 285.95 1.71 M1 190 A2 Cl R2.180 H E or Z 302.01 1.8 M1 191 A2 Cl R2.056 H E or Z 268.04 1.85 M1 192 A2 Cl R2.058 H E or Z 336 1.93 M1 193 A2 Cl R2.059 H E or Z 319.97 1.81 M1 194 A2 Cl R2.060 H E or Z 347.05 1.74 M1 195 A2 Cl R2.061 H E or Z 296.03 2.13 M1 196 A2 Cl R2.062 H E or Z 268.02 1.88 M1 197 A2 Cl R2.063 H E or Z 285.96 1.69 M1 198 A2 Cl R2.064 H E 299.97 1.84 M1 199 A2 Cl R2.065 H E or Z 319.49 1.65 M1 200 A2 Cl R2.066 H E or Z 280.01 1.87 M1 201 A2 Cl R2.067 H E or Z 312 1.61 M1 202 A2 Cl R2.068 H E or Z 369.88 2 M1 203 A2 Cl R2.069 H E or Z 374.01 1.79 M1 204 A2 Cl R2.086 H E or Z 268.04 1.88 M1 205 A2 Cl R2.070 H E or Z 392.08 1.93 M1 206 A2 Cl R2.071 H E or Z 254.04 1.73 M1 207 A2 Cl R2.072 H E or Z 240.02 1.59 M1 208 A2 Cl R2.181 H E or Z 225.99 1.43 M1 209 A2 Cl R2.073 H E or Z 252.01 1.62 M1 210 A2 Cl R2.075 H E or Z 374.02 1.73 M1 211 A2 Cl R2.076 H E or Z 254.04 1.74 M1 212 A2 Cl R2.077 H E or Z 298.05 1.28 M1 213 A2 Cl R2.078 H E or Z 312.89 1.69 M1 214 A2 Cl R2.079 H E or Z 369.96 2.08 M1 215 A2 Cl R2.080 H E or Z 315.99 1.92 M1 216 A2 Cl R2.082 H E or Z 383.86 2.15 M1 217 A2 Cl R2.083 H E or Z 383.95 2.12 M1 218 A2 Cl R2.084 H Z 372.02 2.08 M1 219 A2 Cl R2.088 H E or Z 386.01 1.73 M1 220 A2 Cl R2.092 H E or Z 414 1.93 M1 221 A2 Cl R2.050 H E or Z 364.9 1.95-2.0 M2 1H NMR (400 MHz, DMSO-d6) ppm 2.36 (s, 3 H) 5.01 (s, 2 H) 7.42 (d, J = 8.03 Hz, 2 H) 7.54 (s, 1 H) 7.60 (d, J = 1.51 Hz, 1 H) 7.75 (d, J = 7.80 Hz, 2 H) 8.20 (s, 1 H) 9.01 (s, 1 H) 11.90 (s, 1 H) 222 A2 Cl R2.093 H E or Z 211.8 1.39-1.44 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.92 (s, 3 H) 5.02-5.06 (m, 2 H) 7.54-7.67 (m, 4 H) 7.75 (d, J = 2.01 Hz, 1 H) 7.84 (s, 1 H) 8.41 (s, 1 H) 8.56 (s, 1 H) 8.63 (s, 1 H) 9.21 (s, 1 H) 9.52 (br. s., 1 H) 11.77 (s, 1 H) 223 A2 Cl R2.004 H E or Z 359.9 2.01-2.05 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.86 (d, J = 6.27 Hz, 2 H) 5.01 (s, 2 H) 7.25 (d, J = 6.27 Hz, 1 H) 7.31-7.37 (m, 4 H) 7.49 (s, 1 H) 8.19 (d, J = 1.25 Hz, 1 H) 8.50 (s, 1 H) 9.33 (t, J = 6.13 Hz, 1 H) 9.39 (s, 1 H) 11.81 (s, 1 H) 224 A2 Cl R2.053 H E or Z 283.9 1.71-1.74 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.03 (d, J = 4.52 Hz, 3 H) 5.01 (s, 2 H) 7.48 (s, 1 H) 8.19 (d, J = 1.26 Hz, 1 H) 8.45 (s, 1 H) 8.74 (d, J = 4.52 Hz, 1 H) 9.36 (s, 1 H) 11.69 (s, 1 H) 225 A2 Cl R2.052 H E or Z 270 1.5-1.57 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.00 (s, 2 H) 7.48 (s, 1 H) 8.24 (br. s., 3 H) 8.45 (s, 1 H) 9.33 (s, 1 H) 11.62 (s, 1 H) 226 A2 Cl R2.005 H E or Z 307.9 1.80-1.82 M2 1H NMR (400 MHz, DMSO-d) ppm 3.17 (s, 3 H) 5.02 (s, 2 H) 7.47 (d, J = 1.51 Hz, 1 H) 7.72 (s, 1 H) 8.38 (s, 1 H) 9.34 (s, 1 H) 12.09 (d, J = 15.81 Hz, 1 H) 227 A2 Cl R2.049 H E or Z 297.9 1.80-1.85 M2 1H NMR (400 MHz, DMSO-d6) ppm 1.16 (t, J = 7.03 Hz, 3H) 3.56-3.65 (m, 2 H) 5.01 (s, 2 H) 7.49 (d, J = 1.76 Hz, 1 H) 8.15 (d, J = 1.51 Hz, 1 H) 8.43 (s, 1 H) 8.81 (t, J = 6.08 Hz, 1 H) 9.37 (s, 1 H) 11.62 (s, 1 H) 228 A2 Cl R2.006 H E or Z 297 1.77-1.81 M2 1H NMR (400 MHz, DMSO-d6) ppm 1.21 (t, J = 7.03 Hz, 1 H) 4.13 (q, J = 7.03 Hz, 1 H) 4.60-4.67 (m, 1 H) 4.89 (d, J = 4.27 Hz, 1 H) 6.43 (br. s., 1 H) 7.68 (d, J = 2.01 Hz, 1 H) 7.80 (d, J = 2.01 Hz, 1 H) 8.01 (s, 1 H) 8.90-9.00 (m, 1 H) 229 A2 Cl R2.094 H E or Z 210 1.52-1.54 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.94 (s, 2 H) 5.50-6.22 (m, 1 H) 7.67 (s, 1 H) 7.73 (d, J = 2.01 Hz, 1 H) 7.99 (s, 1 H) 8.26 (s, 1 H) 9.76 (s, 1 H) 230 A2 F R2.007 H E or Z 332.95 1.39 M1 231 A2 F R2.009 H E or Z 350 1.53 M1 232 A2 F R2.010 H E or Z 314.02 1.27 M1 233 A2 F R2.051 H E or Z 355.94 1.02 M1 234 A2 F R2.011 H E or Z 299.94 0.94 M1 235 A2 F R2.043 H E or Z 397 1.98 M1 236 A2 F R2.012 H E or Z 366.9 1.4 M1 237 A2 F R2.044 H E or Z 411.01 1.95 M1 238 A2 F R2.013 H E or Z 305.95 1.44 M1 239 A2 F R2.014 H E or Z 343.97 1.14 M1 240 A2 F R2.015 H E or Z 338.9 1.9 M1 241 A2 F R2.016 H E or Z 285.05 1.65 M1 242 A2 F R2.018 H E or Z 311.94 1.35 M1 243 A2 F R2.019 H E or Z 267.02 1.12 M1 244 A2 F R2.017 H E or Z 306.99 1.63 M1 245 A2 F R2.020 H E or Z 334.97 1.29 M1 246 A2 F R2.045 H E or Z 284.97 1.42 M1 247 A2 F R2.022 H E or Z 329.03 1.26 M1 248 A2 F R2.023 H E or Z 306.99 1.65 M1 249 A2 F R2.024 H E or Z 315.98 1.68 M1 250 A2 F R2.025 H E or Z 333.96 1.19 M1 251 A2 F R2.026 H E or Z 338.9 1.92 M1 252 A2 F R2.027 H E or Z 307.97 1.13 M1 253 A2 F R2.028 H E or Z 263.01 1.01 M1 254 A2 F R2.029 H E or Z 356.96 1.79 M1 255 A2 F R2.030 H E or Z 305.93 1.28 M1 256 A2 F R2.006 H E or Z 281 1.65-1.68 M2 1H NMR (400 MHz, DMSO-d6) ppm 1.21 (t, J = 7.03 Hz, 3 H) 4.14 (q, J = 7.19 Hz, 2 H) 4.63 (s, 2 H) 4.90 (s, 2 H) 7.49 (s, 1 H) 7.51-7.52 (m, 1 H) 8.00 (s, 1 H) 8.88 (s, 1 H) 257 A2 F R2.031 H E or Z 236.98 1.31 M1 258 A2 F R2.047 H E or Z 301.04 1.51 M1 259 A2 F R2.033 H E or Z 406.87 1.91 M1 260 A2 F R2.034 H E or Z 373.91 1.69 M1 261 A2 F R2.035 H E or Z 405.94 1.51 M1 262 A2 F R2.036 H E or Z 304.96 1.7 M1 263 A2 F R2.037 H E or Z 316.01 1.58 M1 264 A2 F R2.038 H E or Z 338.99 1.77 M1 265 A2 F R2.039 H E or Z 338.9 1.4 M1 266 A2 F R2.040 H E or Z 370.98 1.2 M1 267 A2 F R2.003 H E and Z 330 1.89-1.93 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.03 (s, 2 H) 5.11 (s, 1 H) 7.20-7.32 (m, 3 H) 7.35-7.42 (m, 3 H) 7.52-7.58 (m, 3 H) 8.12 (d, J = 10.66 Hz, 1 H) 8.53-8.57 (m, 1 H) 9.35 (s, 1 H) 10.25 (s, 1 H) 10.32 (s, 1 H) 12.03 (s, 1 H) 12.09 (s, 1 H) 268 A2 F R2.055 H E and Z 294 1.76-1.82 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.09 (q, J = 5.27 Hz, 2 H) 5.01 (s, 4 H) 5.08-5.15 (m, 6 H) 5.18 (d, J = 1.76 Hz, 2 H) 5.87-5.97 (m, 3 H) 7.26 (dd, J = 8.91, 2.13 Hz, 3 H) 7.99 (d, J = 2.01 Hz, 1 H) 8.02 (d, J = 4.76 Hz, 1 H) 8.43 (d, J = 1.76 Hz, 1 H) 8.48 (d, J = 1.76 Hz, 2 H) 8.93 (s, 3 H) 9.29 (s, 2 H) 11.74 (s, 2 H) 11.80 (s, 1 H) 269 A2 F R2.041 H E or Z 358 1.56 M1 270 A2 F R2.042 H E or Z 335.99 1.58 M1 271 A2 F R2.054 H E 270.07 1.56 M1 272 A2 F R2.180 H E or Z 286.02 1.66 M1 273 A2 F R2.058 H E or Z 319.98 1.8 M1 274 A2 F R2.059 H E or Z 304.01 1.67 M1 275 A2 F R2.060 H E or Z 330.87 1.61 M1 276 A2 F R2.061 H E or Z 280.04 1.99 M1 277 A2 F R2.063 H E or Z 270 1.54 M1 278 A2 F R2.085 H E or Z 268.03 1.09 M1 279 A2 F R2.064 H E 284.01 1.7 M1 280 A2 F R2.065 H E or Z 304.11 1.53 M1 281 A2 F R2.067 H E or Z 296.02 1.47 M1 282 A2 F R2.068 H E or Z 353.95 1.88 M1 283 A2 F R2.069 H E or Z 358.05 1.67 M1 284 A2 F R2.089 H E or Z 364.16 2.57 M1 285 A2 F R2.070 H E or Z 375.98 1.81 M1 286 A2 F R2.090 H E or Z 388.17 2.06 M1 287 A2 F R2.075 H E or Z 358.05 1.6 M1 288 A2 F R2.091 H E or Z 309.99 1.54 M1 289 A2 F R2.087 H E or Z 317.13 1.67 M1 290 A2 F R2.079 H E or Z 353.82 1.95 M1 291 A2 F R2.080 H E or Z 300 1.79 M1 292 A2 F R2.081 H E or Z 337.97 1.82 M1 293 A2 F R2.082 H E or Z 367.97 2.03 M1 294 A2 F R2.083 H E or Z 367.94 1.99 M1 295 A2 F R2.084 H Z 355.95 1.96 M1 296 A2 F R2.088 H E or Z 370.04 1.61 M1 297 A2 F R2.092 H E or Z 398.07 1.82 M1 298 A2 F R2.053 H E and Z 268 1.59-1.63 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.01-3.04 (m, 4 H) 5.01 (s, 2 H) 5.09 (s, 1 H) 7.25 (dd, J = 8.91, 1.88 Hz, 1 H) 7.97 (d, J = 2.01 Hz, 1 H) 8.00 (s, 1 H) 8.01 (d, J = 5.87 Hz, 1 H) 8.42 (d, J = 2.01 Hz, 1 H) 8.46 (d, J = 1.51 Hz, 1 H) 8.72 (d, J = 4.52 Hz, 1 H) 9.29 (s, 1 H) 11.70 (s, 1 H) 11.75 (s, 1 H) 299 A2 F R2.050 H E or Z 349 1.84-1.91 M2 1H NMR (400 MHz, DMSO-d6) ppm 0.00 (s, 1 H) 2.36 (s, 3 H) 5.01 (s, 2 H) 7.29-7.44 (m, 4 H) 7.76 (d, J = 7.80 Hz, 2 H) 8.20 (s, 1 H) 8.97 (s, 1 H) 11.86 (s, 1 H) 300 A2 F R2.094 H E or Z 194.9 1.35-1.37 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.95 (s, 2 H) 5.16-6.04 (m, 1 H) 7.42 (d, J = 9.56 Hz, 1 H) 7.48 (d, J = 10.60 Hz, 1 H) 7.98 (s, 1 H) 8.18 (br. s., 1 H) 9.70 (s, 1 H) 301 A2 F R2.093 H E or Z 195.8 1.20-1.25 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.93 (s, 2 H) 7.48 (dd, J = 8.91, 2.64 Hz, 2 H) 7.64 (d, J = 10.71 Hz, 1 H) 8.63 (s, 1 H) 9.45 (s, 1 H) 11.40-11.92 (m, 1 H) 302 A2 H R2.007 H E or Z 314.96 1.32 M1 303 A2 H R2.009 H E or Z 332.02 1.46 M1 304 A2 H R2.010 H E or Z 296.03 1.19 M1 305 A2 H R2.011 H E or Z 281.95 0.86 M1 306 A2 H R2.013 H E or Z 287.97 1.36 M1 307 A2 H R2.014 H E or Z 325.98 1.06 M1 308 A2 H R2.015 H E or Z 320.95 1.84 M1 309 A2 H R2.016 H E or Z 267.03 1.58 M1 310 A2 H R2.017 H E or Z 289 1.56 M1 311 A2 H R2.019 H E or Z 248.98 1.04 M1 312 A2 H R2.020 H E or Z 316.92 1.22 M1 313 A2 H R2.045 H E or Z 2 1.33 M1 314 A2 H R2.022 H E or Z 310.98 1.19 M1 315 A2 H R2.033 H E or Z 388.88 1.65 M1 316 A2 H R2.034 H E or Z 355.92 1.63 M1 317 A2 H R2.035 H E or Z 387.94 1.45 M1 318 A2 H R2.037 H E or Z 297.99 1.51 M1 319 A2 H R2.038 H E or Z 321.01 1.71 M1 320 A2 H R2.039 H E or Z 320.89 1.31 M1 321 A2 H R2.003 H E or Z 311.9 1.79-1.85 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.04 (s, 2 H) 7.20 (t, J = 7.24 Hz, 1 H) 7.33-7.46 (m, 3 H) 7.53 (t, J = 7.56 Hz, 1 H) 7.62 (d, J = 8.03 Hz, 2 H) 8.05 (d, J = 7.28 Hz, 1 H) 8.52 (s, 1 H) 9.36 (s, 1 H) 10.33 (s, 1 H) 11.96 (s, 1 H) 322 A2 H R2.055 H E or Z 275.97 1.16 M1 323 A2 H R2.041 H E or Z 340.01 1.48 M1 324 A2 H R2.042 H E or Z 318.01 1.5 M1 325 A2 H R2.054 H E 251.97 1.5 M1 326 A2 H R2.056 H E or Z 234.07 1.63 M1 327 A2 H R2.058 H E or Z 301.97 1.75 M1 328 A2 H R2.059 H E or Z 286 1.61 M1 329 A2 H R2.060 H E or Z 313.01 1.56 M1 330 A2 H R2.061 H E or Z 262.06 1.95 M1 331 A2 H R2.062 H E or Z 234.03 1.68 M1 332 A2 H R2.063 H E or Z 251.99 1.48 M1 333 A2 H R2.064 H E 265.99 1.63 M1 334 A2 H R2.065 H E or Z 285.91 1.66 M1 335 A2 H R2.066 H E or Z 246.05 1.67 M1 336 A2 H R2.054 H Z 251.96 1.49 M1 337 A2 H R2.067 H E or Z 278.01 1.4 M1 338 A2 H R2.068 H E or Z 335.95 1.82 M1 339 A2 H R2.069 H E or Z 340.02 1.62 M1 340 A2 H R2.089 H E or Z 346.14 2.56 M1 341 A2 H R2.070 H E or Z 357.95 1.77 M1 342 A2 H R2.090 H E or Z 369.91 2.02 M1 343 A2 H R2.075 H E or Z 340.02 1.51 M1 344 A2 H R2.077 H E or Z 264.06 1.08 M1 345 A2 H R2.087 H E or Z 298.96 1.61 M1 346 A2 H R2.078 H E or Z 279.06 1.51 M1 347 A2 H R2.079 H E or Z 335.98 1.91 M1 348 A2 H R2.080 H E or Z 282.04 1.73 M1 349 A2 H R2.081 H E or Z 319.95 1.77 M1 350 A2 H R2.082 H E or Z 349.97 1.99 M1 351 A2 H R2.083 H E or Z 349.96 1.95 M1 352 A2 H R2.084 H Z 338.01 1.62 M1 353 A2 H R2.088 H E or Z 352.06 1.55 M1 354 A2 H R2.053 H E or Z 250 1.47-1.51 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.01 (d, J = 4.52 Hz, 3 H) 5.02 (s, 2 H) 7.41 (d, J = 7.53 Hz, 1 H) 7.51 (t, J = 7.65 Hz, 1 H) 8.03 (d, J = 7.53 Hz, 1 H) 8.46 (s, 1 H) 8.67 (d, J = 6.15 Hz, 1 H) 9.28 (s, 1 H) 11.61 (s, 1 H) 355 A2 H R2.050 H E or Z 330.9 1.80-1.83 M2 1H NMR (400 MHz, DMSO-d6) ppm 2.35 (s, 3 H) 5.03 (s, 2 H) 7.39-7.57 (m, 5 H) 7.75 (d, J = 7.76 Hz, 2 H) 8.19 (s, 1 H) 8.90 (s, 1 H) 11.74 (br. s., 1 H) 356 A2 H R2.049 H E or Z 264 1.58-1.65 M2 1H NMR (400 MHz, DMSO-d6) ppm 1.16 (t, J = 7.15 Hz, 3H) 3.59 (quin, J = 6.78 Hz, 2 H) 5.02 (s, 2 H) 7.41 (d, J = 7.53 Hz, 1 H) 7.52 (t, J = 7.65 Hz, 1 H) 7.98 (d, J = 7.78 Hz, 1 H) 8.44 (s, 1 H) 8.71 (t, J = 5.65 Hz, 1 H) 9.26 (s, 1 H) 11.53 (s, 1 H) 357 A2 H R2.052 H E or Z 236 1.29-1.35 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.02 (s, 2 H) 7.41 (d, J = 6.78 Hz, 1 H) 7.49 (t, J = 7.53 Hz, 1 H) 8.05 (d, J = 8.28 Hz, 3 H) 8.48 (s, 1 H) 9.22 (s, 1 H) 11.56 (s, 1 H) 358 A2 H R2.004 H E or Z 326 1.87-1.89 M2 1H NMR (400 MHz, DMSO-d6) ppm 2.09 (s, 1 H) 4.84 (d, J = 6.27 Hz, 2 H) 5.02 (s, 2 H) 7.21-7.42 (m, 6 H) 7.50 (t, J = 7.28 Hz, 1 H) 8.04 (d, J = 7.53 Hz, 1 H) 8.50 (s, 1 H) 9.23 (t, J = 6.45 Hz, 1 H) 9.28 (s, 1 H) 11.71 (s, 1 H) 359 A2 H R2.072 H E or Z 206 1.89-1.92 M2 1H NMR (400 MHz, DMSO-d6) ppm 1.27 (t, J = 7.15 Hz, 3 H) 4.19 (q, J = 7.03 Hz, 2 H) 5.04 (s, 2 H) 7.44-7.55 (m, 2 H) 7.69 (d, J = 7.53 Hz, 1 H) 8.52 (s, 1 H) 9.14 (s, 1 H) 360 A3 R2.007 H E or Z 314.96 1.1 M1 361 A3 R2.008 H E or Z 326 1.01 M1 362 A3 R2.009 H E or Z 331.97 1.24 M1 363 A3 R2.051 H E or Z 337.92 0.86 M1 364 A3 R2.011 H E or Z 281.96 0.67 M1 365 A3 R2.012 H E or Z 348.93 1.17 M1 366 A3 R2.013 H E or Z 287.94 1.33 M1 367 A3 R2.014 H E or Z 325.97 0.92 M1 368 A3 R2.015 H E or Z 320.9 1.73 M1 369 A3 R2.017 H E or Z 289 1.45 M1 370 A3 R2.018 H E or Z 293.94 1.11 M1 371 A3 R2.019 H E or Z 249 0.82 M1 372 A3 R2.020 H E or Z 316.94 1.02 M1 373 A3 R2.021 H E or Z 248.04 0.57 M1 374 A3 R2.022 H E or Z 311 0.98 M1 375 A3 R2.023 H E or Z 289 1.45 M1 376 A3 R2.024 H E or Z 297.7 1.48 M1 377 A3 R2.025 H E or Z 315.99 0.92 M1 378 A3 R2.026 H E or Z 320.9 1.71 M1 379 A3 R2.028 H E or Z 245.03 0.79 M1 380 A3 R2.029 H E or Z 339 1.59 M1 381 A3 R2.030 H E or Z 288 0.97 M1 382 A3 R2.033 H E or Z 388.86 1.8 M1 383 A3 R2.034 H E or Z 355.9 1.38 M1 384 A3 R2.035 H E or Z 387.94 1.26 M1 385 A3 R2.036 H E or Z 286.97 1.5 M1 386 A3 R2.037 H E or Z 298 1.37 M1 387 A3 R2.038 H E or Z 321 1.57 M1 388 A3 R2.039 H E or Z 320.93 1.51 M1 389 A3 R2.003 H E or Z 311.98 1.21 M1 390 A3 R2.055 H E or Z 275.99 1.05 M1 391 A3 R2.041 H E or Z 340.01 1.36 M1 392 A3 R2.042 H E or Z 318.03 1.39 M1 393 A3 R2.054 H E 251.84 1.04 M1 394 A3 R2.180 H E or Z 268 1.94-1.97 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.00 (s, 2 H) 5.09 (s, 1 H) 5.19 (s, 2 H) 7.30-7.47 (m, 5 H) 7.54-7.67 (m, 2 H) 7.75 (d, J = 7.53 Hz, 2 H) 8.37 (s, 1 H) 9.27 (s, 1 H) 395 A3 R2.056 H E or Z 234.02 1.91 M1 396 A3 R2.057 H E or Z 262.06 1.23 M1 397 A3 R2.058 H E or Z 301.96 1.62 M1 398 A3 R2.059 H E or Z 286.03 1.49 M1 399 A3 R2.060 H E or Z 312.88 1.43 M1 400 A3 R2.061 H E or Z 262.12 1.79 M1 401 A3 R2.062 H E or Z 234.06 1.51 M1 402 A3 R2.063 H E or Z 252.14 0.95 M1 403 A3 R2.085 H E or Z 250.04 0.87 M1 404 A3 R2.064 H E 266.02 1.5 M1 405 A3 R2.065 H E or Z 285.92 1.55 M1 406 A3 R2.067 H E or Z 278.05 1.2 M1 407 A3 R2.068 H E or Z 335.93 1.69 M1 408 A3 R2.069 H E or Z 340.06 1.48 M1 409 A3 R2.086 H E or Z 234.06 1.51 M1 410 A3 R2.070 H E or Z 357.97 1.65 M1 411 A3 R2.090 H E or Z 371.83 1.92 M1 412 A3 R2.071 H E or Z 220.08 1.34 M1 413 A3 R2.072 H E or Z 206.03 1.17 M1 414 A3 R2.181 H E or Z 192 1.55-1.59 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.91 (s, 3 H) 5.01 (s, 2 H) 7.58 (d, J = 7.45 Hz, 1 H) 7.63 (s, 1 H) 7.75 (d, J = 7.53 Hz, 1 H) 8.29 (s, 1 H) 9.27 (s, 1 H) 415 A3 R2.073 H E or Z 218.22 1.24 M1 416 A3 R2.074 H E or Z 326 1.18 M1 417 A3 R2.075 H E or Z 340.06 1.41 M1 418 A3 R2.076 H E or Z 220.08 1.35 M1 419 A3 R2.077 H E or Z 264.04 0.92 M1 420 A3 R2.087 H E or Z 298.95 1.48 M1 421 A3 R2.078 H E or Z 279.01 1.38 M1 422 A3 R2.079 H E or Z 335.91 1.79 M1 423 A3 R2.080 H E or Z 282.21 1.6 M1 424 A3 R2.081 H E or Z 319.89 1.65 M1 425 A3 R2.082 H E or Z 349.99 1.79 M1 426 A3 R2.083 H E or Z 349.94 1.88 M1 427 A3 R2.084 H Z 338.02 1.79 M1 428 A3 R2.088 H E or Z 352.07 1.41 M1 429 A3 R2.092 H E or Z 380.08 1.63 M1 430 A3 R2.027 H E or Z 289.98 0.94 M1 431 A3 R2.032 H E or Z 349.93 1.17 M1 432 A4 H R2.072 H E or Z 206 1.74-1.77 M2 1H NMR (400 MHz, DMSO-d6) ppm 1.34 (t, J = 7.03 Hz, 3 H) 2.56 (dt, J = 3.58, 1.85 Hz, 7 H) 3.38 (s, 2 H) 4.24 (q, J = 7.03 Hz, 2 H) 5.13 (s, 2 H) 7.51 (t, J = 7.42 Hz, 1 H) 7.70 (dd, J = 7.65, 0.88 Hz, 1 H) 7.84 (dd, J = 7.28, 0.75 Hz, 1 H) 8.39 (s, 1 H) 9.31 (s, 1 H) 433 A4 H R2.181 H E or Z 192.1 1.58-1.64 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.92 (s, 3 H) 5.08 (s, 2 H) 7.45 (t, J = 7.42 Hz, 1 H) 7.64 (d, J = 7.35 Hz, 1 H) 7.79 (dd, J = 7.28, 1.00 Hz, 1 H) 8.33 (s, 1 H) 9.26 (s, 1 H) 434 A2 H R2.180 H E or Z 268.1 2.097-2.162. M2 1H NMR (400 MHz, DMSO-d6) ppm 5.03 (s, 2 H) 5.21 (s, 2 H) 7.33 (s, 1 H) 7.36-7.47 (m, 5 H) 7.52 (t, J = 7.60 Hz, 1 H) 7.67 (d, J = 7.53 Hz, 1 H) 8.59 (s, 1 H) 9.08 (s, 1 H) 435 A2 H R2.181 H E or Z 191.9 1.74-1.77 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.93 (s, 3 H) 5.04 (s, 2 H) 7.48 (d, J = 7.69 Hz, 1 H) 7.53 (t, J = 7.47 Hz, 1 H) 8.53 (s, 1 H) 9.12 (s, 1 H) 447 A2 Me R2.062 H 248 2.27 M2 448 A2 Me R2.181 H 75-80 449 A2 Me R2.059 H 112-117 450 A2 Me R2.072 H 75-78 451 A2 Me R2.180 H 102-107 452 A2 Me R2.023 H 211-215 453 A1 Cl R2.183 H 152-159 454 A1 F R2.183 H 185-190

Table T3: Characterising Data:

[0548] Table T1 shows all the prepared examples with selected melting point and selected NMR data for prepared compounds. CDCl.sub.3/D.sub.20 and DMSO are used as solvents for NMR 400 MHz measurements. No attempt is made to list all characterising data in all cases.

[0549] In Table T1 and throughout the description that follows, temperatures are given in degrees Celsius; NMR means nuclear magnetic resonance spectrum; MS stands for mass spectrum; % is percent by weight, unless corresponding concentrations are indicated in other units. The following abbreviations are used throughout this description: [0550] m.p.=melting point b.p.=boiling point. [0551] S=singlet br=broad [0552] d=doublet dd=doublet of doublets [0553] t=triplet q=quartet [0554] m=multiplet ppm=parts per million

[0555] The following LC-MS methods were used to characterize the compounds:

[0556] MethodM 1

[0557] ACQUITY SQD Mass Spectrometer from Waters (Single quadrupole mass spectrometer)

[0558] Ionisation method: Electrospray

[0559] Polarity: positive ions

[0560] Capillary (kV) 3.00, Cone (V) 20.00, Extractor (V) 3.00, Source Temperature ( C.) 150, Desolvation Temperature ( C.) 400, Cone Gas Flow (L/Hr) 60, Desolvation Gas Flow (L/Hr) 700

[0561] Mass range: 100 to 800 Da

[0562] DAD Wavelength range (nm): 210 to 400

[0563] Method Waters ACQUITY UPLC with the following HPLC gradient conditions

[0564] (Solvent A: Water/Methanol 9:1, 0.1% formic acid and Solvent B: Acetonitrile, 0.1% formic acid)

TABLE-US-00004 Time (minutes) A (%) B (%) Flow rate (ml/min) 0 100 0 0.75 2.5 0 100 0.75 2.8 0 100 0.75 3.0 100 0 0.75

[0565] Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron; Temperature: 60 C.

[0566] The characteristic values obtained for each compound were the retention time (R.sub.t, recorded in minutes) and the molecular ion as listed in Table 1.

[0567] MethodM2

[0568] Instrumentation:

[0569] Mass Spectrometer: 6410 Triple quadrupole Mass Spectrometer from Agilent Technologies

[0570] HPLC: Agilent 1200 Series HPLC

[0571] Optimized Mass Parameter:

[0572] Ionisation method: Electrospray (ESI)

[0573] Polarity: positive and Negative Polarity Switch

[0574] Scan Type: MS2 Scan

[0575] Capillary (kV): 4.00

[0576] Fragmentor (V): 100.00

[0577] Gas Temperature ( C.): 350

[0578] Gas Flow (L/min): 11

[0579] Nebulizer Gas (psi): 35

[0580] Mass range: 110 to 1000 Da

[0581] DAD Wavelength range (nm): 190 to 400

[0582] Optimized Chromatographic Parameter:

[0583] Gradient Conditions

[0584] (Solvent A: Water, 0.1% formic acid and Solvent B: Acetonitrile, 0.1% formic acid)

TABLE-US-00005 Time (minutes) A (%) B (%) Flow rate (ml/min) 0 90 10 1.8 2.0 0 100 1.8 3.0 0 100 1.8 3.2 90 10 1.8 4.0 90 10 1.8

[0585] Type of column: Waters Xterra MS C18; Column length: 30 mm; Internal diameter of column: 4.6 mm; Particle Size: 3.5; Temperature: 30 C.

[0586] Formulation examples for compounds of formula (I):

Example F-1.1 to F-1.2

Emulsifiable Concentrates

[0587]

TABLE-US-00006 Components F-2.1 F-2.2 A compound selected from the Table T1 25% 50% calciumdodecylbenzenesulfonate 5% 6% castoroilpolyethyleneglycolether (36 mol ethylenoxy units) 5% tributylphenolpolyethyleneglycolether (30 mol ethylenoxy units) cyclohexanone 20% xylenemixture 65% 20%

[0588] Emulsions of any desired concentration can be prepared by diluting such concentrates with water.

Example F-2

Emulsifiable Concentrate

[0589]

TABLE-US-00007 Components F-2 A compound selected from the Table T1 and the tables 1 to 300 10% octylphenolpolyethyleneglycolether 3% (4 to 5 mol ethylenoxy units) Calcium dodecylbenzenesulfonate 3% Castoroilpolyglycolether 4% (36 mol ethylenoxy units) cyclohexanone 30% xylenemixture 50%

[0590] Emulsions of any desired concentration can be prepared by diluting such concentrates with water.

Examples F-3.1 to F-3.4

Solutions

[0591]

TABLE-US-00008 Components F-3.1 F-3.2 F-3.3 F-3.4 A compound selected from the Table T1 and 80% 10% 5% 95% the tables 1 to 300 propylene glycol monomethyl ether 20% polyethylene glycol (relative 70% molecular mass: 400 atomic mass units) N-methylpyrrolid-2-one 20% epoxidised coconut oil 1% 5% benzin (boiling range: 160-190) 94% The solutions are suitable for use in the form of microdrops.

Examples F-4.1 to F-4.4

Granulates

[0592]

TABLE-US-00009 Components F-4.1 F-4.2 F-4.3 F-4.4 A compound selected from the Table T1 and 5% 10% 8% 21% the tables 1 to 300 Kaolin 94% 79% 54% highly dispersed silicic acid 1% 13% 7% Attapulgite 90% 18%

[0593] The novel compound is dissolved in dichloromethane, the solution is sprayed onto the carrier and the solvent is then removed by distillation under vacuum.

Examples F-5.1 and F-5.2

Dusts

[0594]

TABLE-US-00010 Components F-5.1 F-5.2 A compound selected from the Table T1 and 2% 5% the tables 1 to 300 highly dispersed silicic acid 1% 5% Talcum 97% Kaolin 90%

[0595] Ready for use dusts are obtained by intimately mixing all components.

Examples F-6.1 to F-6.3

Wettable Powders

[0596]

TABLE-US-00011 Components F-6.1 F-6.2 F-6.3 A compound selected from the Table T1 and the 25% 50% 75% tables 1 to 300 sodium lignin sulfonate 5% 5% sodium lauryl sulphate 3% 5% sodium diisobutylnaphthalene sulfonate 6% 10% octylphenolpolyethylene glycol ether 2% (7 to 8 mol ethylenoxy units) highly dispersed silicic acid 5% 10% 10% Kaolin 62% 27%

[0597] All components are mixed and the mixture is thoroughly ground in a suitable mill to give wettable powders which can be diluted with water to suspensions of any desired concentration.

Example F7

Flowable Concentrate for Seed Treatment

[0598]

TABLE-US-00012 Components F-7 A compound selected from the Table T1 and 40% the tables 1 to 300 propylene glycol 5% copolymer butanol PO/EO 2% tristyrenephenole with 10-20 moles EO 2% 1,2-benzisothiazolin-3-one 0.5% (in the form of a 20% solution in water) monoazo-pigment calcium salt 5% Silicone oil 0.2% (in the form of a 75% emulsion in water) Water 45.3%

[0599] The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

BIOLOGICAL EXAMPLES

Fungicidal Action

[0600] The compounds which gave >80% disease control at 200 ppm in various tests when compared to untreated control under the same conditions, which show extensive disease development are specified below

[0601] These examples illustrate the fungicidal properties of the compounds described in table T1.

Biological Example 1

Fungicidal Activity Against Blumeria graminis f. sp. Tritici (Erysiphe graminis f. Sp. Tritici)/Wheat/Leaf Disc Preventative (Powdery Mildew on Wheat)

[0602] Wheat leaf segments cv. Kanzler were placed on agar in a 24-well plate and sprayed with the formulated test compound diluted in water at an application rate of 200 ppm. The leaf disks were inoculated by shaking powdery mildew infected plants above the test plates 1 day after application. The inoculated leaf disks were incubated at 20 C. and 60% relative humidity under a light regime of 24 h darkness followed by 12 h/12 h (dark/light) in a climate chamber and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check leaf segments (6-8 days after application). Compounds (from table T1) 76 and 240 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 2

Fungicidal Activity Against Giberella zeae (Fusarium graminearum)/Wheat/Spikelet

[0603] Fusarium graminearum, syn. Gibberella zeae, (Head blight): Wheat spikelets are placed on agar in in a 24-well plate and sprayed with test solutions. After drying, the spikelets are inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound is assessed 6 dpi (days after inoculation) as preventative fungicidal activity. Compound (from table T1) 59 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 3

Fungicidal Activity Against Phaeosphaeria nodorum (Septoria nodorum)/Wheat/Leaf Disc Preventative (Glume Blotch)

[0604] Wheat leaf segments cv Kanzler were placed on agar in a 24-well plate and sprayed with formulated test compound diluted in water at an application rate of 200 ppm. The leaf disks were inoculated with a spore suspension of the fungus 2 days after application. The inoculated test leaf disks were incubated at 20 C. and 75% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (5-7 days after application). Compounds (from table T1) 40, 41, 42, 44, 47, 56, 123, 131, 132, 142, 149 and 189 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 4

Fungicidal Activity Against Phytophthora infestans/Tomato/Leaf Disc Preventative (Late Blight)

[0605] Tomato leaf disks were placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water at an application rate of 200 ppm. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf disks were incubated at 16 C. and 75% relative humidity under a light regime of 24 h darkness followed by 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks. Compound (from table T1) 224 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 5

Fungicidal Activity Against Plasmopara viticola/Grape/Leaf Disc Preventative (Late Blight)

[0606] Grape vine leaf disks were placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf disks were incubated at 19 C. and 80% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (6-8 days after application). Compounds (from table T1) 4, 13, 16, 35, 36, 47, 48, 50, 51, 71, 77, 79, 80, 83, 89, 90, 91, 92, 95, 96, 99, 105, 107, 111, 113, 115, 117, 119, 120, 124, 131, 132, 142, 171, 178, 222, 315, 378, 389, 395, 397, 398, 400, 405, 408 and 423 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 6

Fungicidal Activity Against Puccinia recondita f. sp. Tritici/Wheat/Leaf Disc Curative (Brown Rust)

[0607] Wheat leaf segments are placed on agar in multiwell plates (24-well format). The leaf disks are then inoculated with a spore suspension of the fungus. One day after inoculation the test solution is applied. After appropriate incubation the activity of a compound is assessed 8 dpi (days after inoculation) as curative fungicidal activity. Dose range: 200-22 ppm. Compounds (from table T1) 76, 91 and 122 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 7

Fungicidal Activity Against Puccinia recondita f. sp. Tritici/Wheat/Leaf Disc Preventative (Brown Rust)

[0608] Wheat leaf segments cv. Kanzler were placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments were incubated at 19 C. and 75% rh under a light regime of 12 h light/12 h darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7-9 days after application).

[0609] Compounds (from table T1) 42, 48, 57, 71, 76, 128, 130, 131, 132, 142, 222, 284, 449 and 453 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 8

Fungicidal Activity Against Magnaporthe grisea (Pyricularia oryzae)/Rice/Leaf Disc Preventative (Rice Blast)

[0610] Rice leaf segments cv. Ballila were placed on agar in multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water at an application rate of 200 ppm. The leaf segments were inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf segments were incubated at 22 C. and 80% rh under a light regime of 24 h darkness followed by 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (5-7 days after application). Compounds (from table T1) 131 and 149 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 9

Fungicidal Activity Against Pyrenophora teres/Barley/Leaf Disc Preventative (Net Blotch)

[0611] Barley leaf segments cv. Hasso were placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf segments were inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf segments were incubated at 20 C. and 65% rh under a light regime of 12 h light/12 h darkness in a climate cabinet and the activity of a compound was assessed as disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (5-7 days after application). Compounds (from table T1) 44 and 149 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 10

Fungicidal Activity Against Botrvotinia fuckeliana (Botrytis cinerea)/Liquid Culture (Gray Mould)

[0612] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (Vogels broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200 ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24 C. and the inhibition of growth was determined photometrically 3-4 days after application.

[0613] Compounds (from table T1) 11, 30, 76, 82, 89, 114, 123, 124, 126, 128, 130, 131, 132, 135, 139, 140, 141, 142, 149, 248, 263, 299, 369, 375, 378, 385, 387, 388, 405, 416, 448 and 450 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 11

Fungicidal Activity Against Glomerella lagenarium (Colletotrichum lagenarium)/Liquid Culture (Anthracnose)

[0614] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200 ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24 C. and the inhibition of growth was measured photometrically 3-4 days after application. Compounds (from table T1) 2, 3, 4, 5, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 30, 31, 32, 33, 34, 35, 36, 37, 38, 40, 41, 42, 44, 46, 47, 48, 49, 50, 51, 52, 53, 54, 56, 57, 58, 59, 60, 61, 62, 68, 69, 71, 72, 73, 75, 76, 77, 78, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 91, 92, 93, 94, 95, 96, 98, 99, 100, 101, 102, 104, 105, 108, 112, 113, 114, 115, 116, 121, 122, 123, 124, 126, 127, 128, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 146, 147, 149, 151, 152, 153, 154, 160, 163, 165, 167, 171, 174, 175, 176, 180, 183, 184, 189, 190, 191, 192, 193, 195, 196, 197, 198, 199, 200, 201, 204, 206, 207, 208, 209, 210, 211, 212, 215, 221, 224, 225, 226, 227, 228, 235, 244, 248, 254, 255, 256, 257, 262, 263, 268, 271, 272, 273, 276, 277, 278, 279, 280, 281, 285, 287, 288, 289, 290, 291, 292, 293, 294, 297, 298, 299, 301, 305, 309, 310, 318, 319, 322, 325, 327, 328, 332, 333, 334, 335, 336, 337, 338, 339, 341, 343, 344, 345, 347, 348, 349, 353, 354, 356, 357, 359, 366, 368, 369, 375, 378, 380, 382, 385, 387, 388, 393, 394, 395, 397, 398, 400, 401, 402, 404, 405, 409, 412, 413, 414, 415, 417, 418, 420, 422, 423, 424, 425, 426, 427, 428, 429, 434, 435, 447, 448, 452 and 453 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 12

Fungicidal Activity Against Fusarium culmorum/Liquid Culture (Head Blight)

[0615] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format), the nutrient broth containing the fungal spores was added. The test plates were incubated at 24 C. and the inhibition of growth was determined visually 3-4 days after application. Compounds (from table T1) 48, 57, 58, 59, 61, 71, 124, 127, 128, 130, 131, 132, 135, 139, 140, 141, 142, 143, 144, 197, 206, 207, 208, 209, 271, 279, 280, 378, 387, 393, 394, 395, 398, 401, 402, 404, 405, 412, 413, 415 and 418 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 13

Fungicidal Activity Against Gaeumannomyces graminis/Liquid Culture (Take-all of Cereals)

[0616] Mycelial fragments of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200 ppm, the nutrient broth Cp.33, containing the fungal spores is added. The test plates were incubated at 24 C. and the inhibition of growth was determined photometrically 4-5 days after application. Compounds (from table T1) 9, 11, 13, 21, 27, 30, 32, 33, 40, 41, 42, 44, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 61, 67, 68, 70, 71, 74, 82, 83, 88, 89, 90, 92, 96, 99, 102, 112, 114, 119, 121, 122, 123, 124, 125, 126, 127, 128, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 144, 149, 150, 151, 152, 153, 154, 165,169, 171,176, 180, 184,185,189, 190, 191, 192, 193, 195, 196, 197, 198, 199, 200, 201, 204, 206, 207, 208, 209, 210, 211, 212, 215, 217, 218, 220, 222, 235, 248, 254, 259, 263, 271, 272, 273, 274, 276, 277, 279, 280, 281, 283, 285, 286, 287, 288, 289, 290, 291, 292, 293, 294, 295, 297, 308, 310, 315, 318, 325, 326, 327, 328, 330, 331, 332, 333, 334, 335, 336, 337, 341, 343, 344, 345, 347, 348, 349, 350, 351, 352, 353, 362, 368, 369, 375, 376, 378, 380, 382, 385, 386, 387, 393, 394, 395, 396, 397, 398, 401, 402, 404, 405, 409, 410, 412, 413, 415, 416, 418, 420, 421, 422, 423, 424, 425, 426, 427, 428, 429, 449 and 450 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 14

Fungicidal Activity Monographella nivalis (Microdochium nivale)/Liquid Culture (Foot Rot Cereals)

[0617] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200 ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24 C. and the inhibition of growth was determined photometrically 4-5 days after application. Compounds (from table T1) 11, 13, 21, 27, 30, 32, 33, 40, 41, 42, 44, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 61, 67, 68, 69, 70, 71, 74, 76, 82, 84, 88, 89, 96, 99, 102, 112, 114, 115, 121, 122, 123, 124, 125, 126, 127, 128, 130, 131, 132, 133, 134, 135, 136, 138, 139, 140, 141, 142, 143, 144, 149, 151, 152, 153, 154, 171, 175, 176, 178, 180, 183, 185, 189, 190, 191, 193, 195, 196, 197, 198, 199, 200, 201, 204, 205, 206, 207, 208, 209, 210, 211, 212, 215, 216, 217, 221, 222, 224, 225, 226, 227, 228, 229, 248, 257, 259, 271, 272, 273, 276, 277, 279, 280, 281, 285, 287, 290, 291, 292, 293, 294, 295, 299, 315, 325, 327, 328, 331, 332, 333, 334, 335, 336, 337, 339, 341, 343, 345, 348, 349, 350, 352, 353, 354, 356, 357, 359, 362, 366, 369, 375, 378, 380, 382, 385, 387, 388, 392, 393, 394, 395, 396, 397, 398, 400, 401, 402, 404, 405, 408, 409, 410, 412, 413, 414, 415, 416, 417, 418, 420, 421, 422, 423, 424, 425, 426, 427, 428, 429, 432, 433, 434, 435, 447, 448, 449, 450, 451 and 453 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 15

Fungicidal Activity Against Mycosphaerella arachidis (Cercospora arachidicola)/Liquid Culture (Early Leaf Spot)

[0618] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200 ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24 C. and the inhibition of growth was determined photometrically 4-5 days after application. Compounds (from table T1) 41, 46, 47, 48, 51, 52, 54, 56, 57, 58, 59, 61, 67, 68, 70, 71, 76, 89, 114, 115, 123, 124, 125, 126, 127, 128, 130, 131, 132, 133, 134, 135, 136, 139, 140, 141, 142, 143, 144, 147, 149, 151, 153, 154, 160, 167, 174, 176, 178, 190, 197, 201, 204, 206, 207, 208, 209, 211, 212, 221, 222, 224, 225, 227, 257, 299, 301, 359, 369, 378, 380, 387, 388, 393, 402, 405, 413, 415, 416, 425, 434 and 448 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 16

Fungicidal Activity Against Pythium ultimum/Liquid Culture (Seedling Damping Off)

[0619] Mycelia fragments and oospores of a newly grown liquid culture of the fungus were directly mixed into nutrient broth (potato dextrose broth). After placing a DMSO solution of test compound into a 96-well format microtiter plate at an application rate of 200 ppm, the nutrient broth containing the fungal mycelia/spore mixture was added. The test plates were incubated at 24 C. and the inhibition of growth was determined photometrically 2-3 days after application. Compounds (from table T1) 2, 3, 4, 5, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 30, 31, 32, 33, 34, 35, 36, 38, 41, 42, 47, 48, 52, 56, 57, 58, 60, 61, 62, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 110, 111, 112, 114, 115, 116, 117, 118, 119, 120, 121, 122, 127, 128, 129, 130, 131, 132, 133, 135, 138, 139, 140, 141, 142, 143, 144, 145, 146, 151, 155, 156, 157, 158, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 179, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 193, 195, 196, 197, 198, 199, 200, 201, 204, 206, 207, 208, 209, 210, 211, 212, 215, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 236, 237, 239, 240, 241, 242, 243, 244, 245, 246, 247, 248, 250, 252, 253, 254, 255, 256, 257, 258, 259, 261, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 276, 277, 278, 279, 280, 281, 283, 285, 287, 288, 291, 295, 296, 297, 298, 299, 300, 301, 302, 303, 304, 305, 306, 307, 309, 310, 311, 312, 313, 314, 315, 317, 318, 320, 321, 322, 325, 326, 327, 328, 330, 331, 332, 333, 334, 335, 336, 337, 339, 341, 343, 344, 345, 348, 349, 352, 353, 354, 355, 356, 357, 358, 359, 360, 362, 370, 371, 372, 374, 383, 384, 387, 388, 389, 390, 393, 394, 395, 396, 402, 409, 412, 413, 414, 415, 416, 418, 419, 420, 421, 430, 432, 433, 434, 435, 447, 448, 449, 450, 453 and 454 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 17

Fungicidal Activity Against Thanatephorus cucumeris (Rhizoctonia solani)/Liquid Culture (Foot Rot, Damping-Off)

[0620] Mycelia fragments of a newly grown liquid culture of the fungus were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format), the nutrient broth containing the fungal material was added. The test plates were incubated at 24 C. and the inhibition of growth was determined photometrically 3-4 days after application. Compounds (from table T1) 11, 30, 33, 41, 47, 48, 56, 57, 58, 61, 71, 75, 76, 85, 89, 96, 114, 131, 165, 171, 190, 197, 248, 255, 263, 280, 310, 334, 369, 378, 380, 387, 393, 405 and 425 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 18

Fungicidal Activity Against Sclerotinia sclerotiorum/Liquid Culture (White Mold, Etc.)

[0621] Mycelial fragments of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24 C and the inhibition of growth was determined photometrically after 72 hrs at 620 nm.

[0622] Compounds (from table T1) 76, 101, 102, 114, 139, 140, 141, 142, 149, 176, 387, 388, 413 and 454 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 19

Fungicidal Activity Against Mycosphaerella graminicola (Septoria tritici)/Liquid Culture (Septoria Blotch)

[0623] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200 ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24 C. and the inhibition of growth was determined photometrically 4-5 days after application. Compounds (from table T1) 30, 40, 41, 46, 47, 48, 49, 50, 51, 54, 56, 57, 58, 61, 67, 68, 71, 76, 82, 84, 88, 89, 114, 121, 123, 124, 126, 127, 128, 130, 131, 132, 135, 136, 138, 139, 140, 141, 142, 144, 149, 151, 152, 154, 189, 190, 193, 196, 197, 198, 199, 200, 201, 204, 206, 207, 208, 209, 210, 211, 212, 222, 271, 272, 276, 277, 279, 280, 281, 287, 325, 327, 332, 334, 336, 343, 348, 352, 369, 378, 380, 385, 387, 388, 393, 394, 395, 397, 398, 400, 401, 402, 404, 405, 408, 409, 412, 413, 414, 415, 416, 418, 420, 425, 426, 427, 428, 429, 432, 433, 448 and 450 at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

Biological Example 20

Fungicidal Activity Against Gaumannomyces graminis/Wheat

[0624] A defined amount of mycelium of G. graminis is mixed with water. The formulated test compounds are added to the mycelium suspension. The mixture is applied into a pouch which was previously equipped with a filter paper. After the application wheat seeds cv. Arina are sown into the upper fault of the filter paper. The prepared pouches are then incubated for 14 days at 18 C./16 C. (day/night) and a rel. humidity of 80% with a photo period of 14 h. The evaluation is made by assessing the degree of root browning.

[0625] Compounds (from table T1) 224 and 405 at 20 ppm give at least 80% disease control in this test compared to an untreated control, which shows extensive disease development.

Biological Example 21

Fungicidal Activity Against Monographella nivale (Microdochium nivale)/Wheat

[0626] Formulated test compound is applied into a pouch which was previously equipped with a filter paper. After the application wheat seeds cv. Arina infected with M. nivale are sown into the upper fault of the filter paper. The pouches are then incubated for 7 days in the dark at 7 C./5 C. (day/night) and 80% r. h. After 1 week light is supplied at the same temperature cycle. Another two weeks later plants were transferred to 17 C./16 C. (day/night) and 80% r. H. The disease incidence is assessed 4 weeks after sowing. Compound (from table T1) 70 at 60 ppm give at least 80% disease control in this test compared to an untreated control, which shows extensive disease development.

Biological Example 22

Fungicidal Activity Against Pythium ultimum/Cotton

[0627] A defined amount of mycelium of P. ultimum is mixed with water. The formulated test compound is added to the mycelium suspension. The mixture is applied into a pouch which was previously equipped with a filter paper. After the application cotton seeds cv. Sure Grow 747 are sown into the upper fault of the filter paper. The prepared pouches are then incubated for 7 days at 18 C. followed by 3 days at 24 C. and a rel. humidity of 100% with a photo period of 14 h. The evaluation is made by assessing the emergence and the degree of disease on the roots. Compound (from table T1) 224 and 225 at 20 ppm give at least 80% disease control in this test compared to an untreated control, which shows extensive disease development.

Biological Example 23

Fungicidal Activity Against Puccinia recondita/Wheat

[0628] 1 week old wheat plants cv. Arina were treated with the formulated test compound in a spray chamber. Two days after application wheat plants were inoculated by spraying a spore suspension (1105 uredospores/ml) on the test plants. After an incubation period of 1 day at 200 C and 95% r. h. plants were kept for 9 days at 200 C and 60% r.h. in a greenhouse. The disease incidence was assessed 10 days after inoculation.

[0629] Compound (from table T1) 50 at 20 ppm give at least 80% disease control in this test compared to an untreated control, which shows extensive disease development.

BENZOXABOROLE FUNGICIDES

Assignee

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Cpc classification

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C07F5/027

CHEMISTRY; METALLURGY

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A01N25/04

HUMAN NECESSITIES

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A23B2/771

HUMAN NECESSITIES

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A01N55/08

HUMAN NECESSITIES

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C07F5/025

CHEMISTRY; METALLURGY

International classification

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A01N55/08

HUMAN NECESSITIES

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A01N25/04

HUMAN NECESSITIES

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C07F5/02

CHEMISTRY; METALLURGY

Abstract

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Description