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) ##STR00446## R.sup.1 is H, fluorine, chlorine, bromine, cyano, nitro, unsubstituted or substituted C.sub.1-C.sub.4alkyl or unsubstituted or substituted C.sub.1-C.sub.4haloalkyl, unsubstituted or substituted C.sub.1-C.sub.4alkoxy, haloalkoxy; G=OR.sup.2, NR.sup.3R.sup.4 R.sup.2, R.sup.3 and R.sup.4 independently are H, unsubstituted or substituted C.sub.1-C.sub.6alkyl, haloalkyl, six to 10 membered aryl, 1,3-benzodioxole-(C.sub.0-C.sub.2), five to ten membered heteroaryl which may be mono or bicyclic containing 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, C.sub.3-C.sub.6cycloalkyl, unsubstituted or substituted heterocycloalkyl containing 3 to 10 ring members containing 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, unsubstituted or substituted C.sub.1-C.sub.6alkoxy, unsubstituted or substituted C.sub.1-C.sub.6haloalkoxy, unsubstituted or substituted C.sub.2-C.sub.6alkenyl, unsubstituted or substituted C.sub.2-C.sub.6alkynyl, or R.sup.3 and R.sup.4 form together with the nitrogen to which they are attached a 3 to 9 ring containing 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, and wherein the substituents for the substituted aryl, heteroaryl, cycloalkyl, heterocycloalkyl and alkyl can be independently mono- or polysubstituted by substituents selected from oxo, OH, CN, NO.sub.2, F, Cl, SH, SC.sub.1-4 alkyl, S(O).sub.2N heteroaryl, S(O).sub.2N-aryl, C.sub.1-4 alkyl 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 heteroaryl, unsubstituted or substituted C.sub.3-C.sub.7 cycloalkyl, and unsubstituted or substituted C.sub.3-C.sub.7 heterocycloalkyl, 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, SS(O).sub.2OH, S(O).sub.2OH, indolin, unsubstituted or substituted six- to ten-membered-aryl(alkylene).sub.(0-3) and unsubstituted or substituted six- to ten-membered-aryl(alkylene).sub.(0-3)oxy; wherein the heterocycloalkyl and heteroaryl containing 3 to 10 ring members containing 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 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, and or N-oxide thereof.

2. A compound of formula (I) ##STR00447## wherein R.sup.1 is H, fluorine, chlorine, bromine, cyano, nitro, unsubstituted or substituted C.sub.1-C.sub.4alkyl or unsubstituted or substituted C.sub.1-C.sub.4haloalkyl, unsubstituted or substituted C.sub.1-C.sub.4alkoxy, haloalkoxy; G=OR.sup.2, NR.sup.3R.sup.4 R.sup.2, R.sup.3 and R.sup.4 independently are H, unsubstituted or substituted C.sub.1-C.sub.6alkyl, haloalkyl, six to 10 membered aryl, 1,3-benzodioxole-(C.sub.0-C.sub.2)-, five to ten membered heteroaryl which may be mono or bicyclic containing 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, C.sub.3-C.sub.6cycloalkyl, unsubstituted or substituted heterocycloalkyl containing 3 to 10 ring members containing 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, unsubstituted or substituted C.sub.1-C.sub.6alkoxy, unsubstituted or substituted C.sub.1-C.sub.6haloalkoxy, unsubstituted or substituted C.sub.2-C.sub.6alkenyl, unsubstituted or substituted C.sub.2-C.sub.6alkynyl, or R.sup.3 and R.sup.4 form together with the nitrogen to which they are attached a 3 to 9 ring containing 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, and wherein the substituents for the substituted aryl, heteroaryl, cycloalkyl, heterocycloalkyl and alkyl can be independently mono- or polysubstituted by substituents selected from oxo, OH, CN, NO.sub.2, F, Cl, SH, SC.sub.1-4 alkyl, S(O).sub.2N heteroaryl, S(O).sub.2N-aryl, C.sub.1-4 alkyl 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 heteroaryl, unsubstituted or substituted C.sub.3-C.sub.7 cycloalkyl, and unsubstituted or substituted C.sub.3-C.sub.7 heterocycloalkyl, 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, SS(O).sub.2OH, S(O).sub.2OH, indolin, unsubstituted or substituted six- to ten-membered-aryl(alkylene).sub.(0-3) and unsubstituted or substituted six- to ten-membered-aryl(alkylene).sub.(0-3)oxy; wherein the heterocycloalkyl and heteroaryl containing 3 to 10 ring members containing 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 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 the compound of formula (I) is not 1,3-dihydro-1-hydroxy-2,1-Benzoxaborole-7-carboxylic acid methyl ester or 3-dihydro-1-hydroxy-2,1-Benzoxaborole-7-carboxylic acid or 1,3-dihydro-1-hydroxy-N-phenyl-2,1-Benzoxaborole-6-carboxamide or 4-[[(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)carbonyl]amino]-benzenesulfonic acid or 1,3-dihydro-1-hydroxy-2,1-Benzoxaborole-6-carboxylic acid.

3. A compound of formula (I) according to claim 1 wherein R.sup.1 is fluorine or chlorine; G is OR.sup.2 or NR.sup.3R.sup.4; R.sup.2 is a C.sub.1-C.sub.6alkyl or C.sub.1-C.sub.6haloalkyl; R.sup.3 and R.sup.4 independently are H, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, aryl, heteroaryl, C.sub.3-C.sub.6cycloalkyl, heterocycloalkyl, alkoxy, haloalkoxy, C.sub.2-C.sub.6alkenyl, or C.sub.2-C.sub.6alkynyl.

4. A compound of formula (I) according to claim 1 wherein R.sup.1 is fluorine or chlorine; G is OR.sup.2 or NR.sup.3R.sup.4; R.sup.2 is a C.sub.1-C.sub.6alkyl; and R.sup.3 and R.sup.4 independently are H, C.sub.1-C.sub.6alkyl, heterocycloalkyl, alkoxy or haloalkoxy.

5. A compound of formula (I) according to claim 1 wherein R.sup.1 fluorine or chlorine; G is OR.sup.2 or NR.sup.3R.sup.4; R.sup.2 is a C.sub.1-C.sub.6alkyl; R.sup.3 and R.sup.4 independently are H, methyl, methoxy, trifluoromethoxy, or heterocycloalkyl having a ring comprising from 2 to 6 carbon atoms and from 1 to 3 heteroatoms selected from N, O, S.

6. A compound of formula (I) according to claim 1 wherein G is NR.sup.3R.sup.4.

7. A compound of formula (I) according to claim 1 wherein G is OR.sup.2.

8. 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.

9. 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.

10. 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.

11. A composition as defined in claim 9 further comprising at least one additional active ingredient.

Description

PREPARATION EXAMPLES

Example P1

Preparation of 2-bromoterephthalic acid

[0161] ##STR00027##

[0162] To a solution of 2-bromo-1,4-dimethyl-benzene (20 g, 108.1 mmol) in water (400 ml) was added potassium permanganate (69 g, 432.3 mmol) in portions at ambient temperature. The reaction mass was heated at 70 C. for 12 h. The dark coloured reaction mass was cooled to room temperature and acidified to pH 2 using 2N HCl. Aqueous solution extracted with ethyl acetate (3100 ml). Combined organic layers were dried over sodium sulfate and evaporated under reduced pressure. The crude was subject to flash chromatography over silicagel with cyclohexane/ethyl acetate 85:15 to 50:50 as eluent to obtain 2-bromoterephthalic acid (13.5 g, 51% of theoretical yield) as a white solid.

[0163] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 7.80-7.84 (m, 2H) 7.98 (dd, J=7.91, 1.63 Hz, 2H) 8.14 (d, J=1.51 Hz, 2H) 13.62 (br. s., 2H)

[0164] MS [MH].sup.: 244.9 (rt 0.87-0.92 min)

Example P2

Preparation of 2-bromo-5-fluoro-terephthalic acid

[0165] ##STR00028##

[0166] To a solution of 1-bromo-4-fluoro-2,5-dimethyl-benzene (5 g, 23.8847 mmol) in water (150 ml) was added potassium permanganate (8.68 g, 54.934 mmol) in portions at ambient temperature. The reaction mass was heated at 70 C. for 16 h. The dark colored reaction mass was cooled to room temperature and filtered. The filtrate was acidified to pH 2 using 2N HCl. The white solid thus obtained was collected by filtration and washed with water (10 ml) and dried under vacuum to obtain 2-bromo-5-fluoro-terephthalic acid (1.8 g, 29% of theoretical yield) as a white solid.

[0167] MS [MH].sup.: 261.1/262.1 (rt 0.65-0.67 min)

Example P3

Preparation of dimethyl 2-bromobenzene-1,4-dicarboxylate

[0168] ##STR00029##

[0169] A solution of 2-bromoterephthalic acid (5.000 g, 20.41 mmol) in thionyl chloride (20.00 mL, 273 mmol) was heated at 100 C. for 5 h. The dark colored reaction mass was cooled to room temperature and solvent was evaporated off under reduced pressure. The residual mass was cooled to 0 C. and methanol (20 ml) and triethylamine (5 ml, 35.5 mmol) were added slowly under nitrogen. The reaction mixture was then stirred for 2 h at ambient temperature. The solution was evaporated to dryness under reduced pressure. The residual mass was dissolved in ethylacetate (100 ml) and washed with water (225 ml), followed by 2N HCl (225 ml) and finally with saturated sodium bicarbonate solution. Combined organic layers were dried over sodium sulfate and evaporated under reduced pressure to obtain dimethyl 2-bromobenzene-1,4-dicarboxylate (5.5 g, 99% of theoretical yield) as a white solid.

[0170] .sup.1H NMR (400 MHz, CHLOROFORM-d) ppm 3.95 (d, J=1.25 Hz, 3H) 3.96 (d, J=1.25 Hz, 3H) 7.81 (dd, J=8.03, 1.25 Hz, 1H) 8.00 (d, J=8.03 Hz, 1H) 8.31 (s, 1H)

[0171] MS [MH].sup.: 272.9/273.9 (rt 1.90-1.97 min)

Example P4

Preparation of dimethyl 2-bromo-5-chloro-benzene-1,4-dicarboxylate

[0172] ##STR00030##

[0173] To a solution of 2-bromo-5-chloro-terephthalic (50 g, 178.91 mmol) in methanol (500 mL) was added concentrated sulfuric acid (50 ml) drop wise at 0 C. The reaction was refluxed for 6 h. The reaction mass was cooled to room temperature and solvent was evaporated off under reduced pressure. The residual mass was dissolved in ethylacetate (100 ml) and washed with water (225 ml) and finally with saturated sodium bicarbonate solution. Combined organic layers were dried over sodium sulfate and evaporated under reduced pressure to obtain dimethyl 2-bromo-5-chloro-benzene-1,4-dicarboxylate (48.5 g, 158 mmol, 88.2% of theoretical yield) as a white solid.

[0174] .sup.1H NMR (400 MHz, DMSO-d6) ppm 3.89 (s, 6H) 7.97 (s, 1H) 8.15 31 (s, 1H)

Example P5

Preparation of dimethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,4-dicarboxylate

[0175] ##STR00031##

[0176] To a stirred solution of dimethyl 2-bromobenzene-1,4-dicarboxylate (15.8 g, 57.9 mmol) in 1,4 dioxane (140 mL) was added fused potassium acetate (17.2 g, 174 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (19.1 g, 75.2 mmol) and finally [1,1-Bis(diphenylphosphino)ferrocene]-dichloropalladium(II) dichloromethane adduct (2.41 g, 2.89 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 sodium sulfate, 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 dimethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,4-dicarboxylate (15 g, 81% of theoretical yield).

[0177] .sup.1H NMR (400 MHz, CHLOROFORM-d) ppm 1.41-1.45 (m, 15H) 3.94 (s, 6H) 8.00 (s, 1H) 8.05-8.13 (m, 1H) 8.16 (s, 1H)

Example P6

Preparation of methyl 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylate

[0178] ##STR00032##

[0179] To a stirred solution of dimethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,4-dicarboxylate (17 g, 53.11 mmol) in methanol (170 mL) was added sodium borohydride (4.2 g, 106.2 mmol) in portions at 0 C. The reaction mixture was then allowed to stir at ambient temperature for 12 h. The reaction mixture was diluted with water (100 mL) and evaporated under reduced pressure. The residual mass was diluted with 2N HCl to pH 2 and stirred for 4 h. Precipitation of fine white solid occurred, which was collected by filtration and washed with water and dried under vacuum to afford methyl 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylate (9 g, 88% of theoretical yield) as a white solid.

[0180] .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 3.33 (s, 3H) 3.88 (s, 3H) 5.07 (s, 2H) 7.56 (dd, J=8.03, 0.75 Hz, 1H) 8.07 (d, J=8.13 Hz, 1H) 8.41 (s, 1H) 9.39 (s, 1H)

[0181] LC-MS-M+H 193 (RT; 1.40-1.42)

Example P7

Preparation of 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylic acid

[0182] ##STR00033##

[0183] To a stirred solution of methyl 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylate (5 g, 26.04 mmol) in water (10 mL) was added sodium hydroxide (2.6 g, 65.1 mmol) dissolved in 10 ml water. Reaction mass was stirred at 50 C. for 12 h. The reaction mixture was cooled to 10 C. and diluted with 2N HCl to pH 2. Precipitation of fine white solid occurred, which was collected by filtration and washed with water and dried under vacuum to afford 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylic acid (4.2 g, 91% of theoretical yield) as a white solid.

[0184] .sup.1H NMR (400 MHz, DMSO-d6) ppm 4.91-5.03 (m, 1H) 5.05 (s, 2H) 7.45-7.58 (m, 1H) 7.98-8.10 (m, 1H) 8.39-8.41 (m, 1H) 8.63-10.03 (m, 1H) 11.60-14.04 (m, 1H)

[0185] MS [MH].sup.: 177 (rt 1.07-1.10 min)

Example P8

Preparation of ethyl 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylate

[0186] ##STR00034##

[0187] To a stirred solution of 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylic acid (0.1 g, 26.04 mmol) in ethanol (2 mL) was added conc. Sulphuric acid (0.2 ml). Reaction mass was refluxed overnight. The reaction mixture was the cooled to ambient temperature and solvent was evaporated under reduced pressure. The residual mass thus obtained was dissolved in ethyl acetate (10 mL). Organic layer was washed with water (3200 mL) followed by brine wash (200 mL). Organic layer was then dried over sodium sulfate, filtered and evaporated completely to give crude compound. The crude obtained was purified by flash chromatography over silicagel with hexane/ethyl acetate 1:0 to 80:20 as eluent to afford desired compound ethyl 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylate (0.101 g, 90% of theoretical yield).

[0188] .sup.1H NMR (400 MHz, DMSO-d6) ppm 1.18-1.37 (m, 3H) 4.34 (q, J=7.03 Hz, 2H) 5.07 (s, 2H) 7.56 (d, J=7.91 Hz, 1H) 8.07 (dd, J=7.91, 1.63 Hz, 1H) 8.41 (dd, J=1.51, 0.75 Hz, 1H) 9.39 (s, 1H)

[0189] MS [M+H].sup.+: 207.1 (rt 1.56-1.60 min)

Example P9

Preparation of 3-thienyl methyl 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylate

[0190] ##STR00035##

[0191] To a stirred solution of 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylic acid (0.150 g, 0.843 mmol) in dichloromethane (10 mL/g, 23.4 mmol) were added 3-thienylmethanol (0.106 g, 0.927 mmol), 3-(ethyliminomethyleneamino)-N,N-dimethyl-propan-1-amine hydrochloride (0.178 g, 0.927 mmol) and DMAP (0.002 g, 0.0169 mmol) and the RM was stirred at ambient temperature for 5 h. Reaction mixture was diluted 10 ml water and then acidified with dil.HCl till pH-3. The aqueous layer was then extracted with dichloromethane (250 ml). The combined organic layer was washed with brine solution (210 ml) and then dried over anhydrous sodium sulfate, filtered and evaporated completely to give crude compound. The crude mass thus obtained was purified by flash chromatography over silica gel with hexane/ethyl acetate 1:0 to 70:30 as eluent to afford desired compound 3-thienylmethyl 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylate (0.120 g, 52% of theoretical yield).

[0192] .sup.1H NMR (400 MHz, DMSO-d6) ppm 1.17 (s, 1H) 1.22 (s, 1H) 2.50 (dt, J=3.70, 1.79 Hz, 3H) 3.34 (s, 1H) 5.06 (s, 2H) 5.54 (s, 2H) 7.06 (t, J=4.41 Hz, 1H) 7.28 (d, J=3.64 Hz, 1H) 7.54-7.62 (m, 2H) 8.06 (d, J=7.83 Hz, 1H) 8.40 (s, 1H) 9.42 (s, 1H)

Example P10

Preparation of N-[(4-chlorophenyl)methyl]-1-hydroxy-3H-2,1-benzoxaborole-6-carboxamide

[0193] ##STR00036##

[0194] To a stirred solution of 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylic acid (0.080 g, 0.4496 mmol) in dichloromethane (10 mL/g, 23.4 mmol) were added (4-chlorophenyl)methanamine (0.070 g 0.4945 mmol), HATU (0.188 g, 0.4945 mmol) and triethylamine (0.136 g, 1.349 mmol) and the RM was stirred at ambient temperature for 12 h. Reaction mixture was diluted 10 ml water. The aqueous layer was then extracted with dichloromethane (250 ml). The combined organic layer was washed with brine solution (210 ml) and then dried over anhydrous sodium sulfate, filtered and evaporated completely to give crude compound. The crude mass thus obtained was purified by flash chromatography over silica gel with hexane/ethyl acetate 1:0 to 70:30 as eluent to afford desired compound N-[(4-chlorophenyl)methyl]-1-hydroxy-3H-2,1-benzoxaborole-6-carboxamide (0.055 g, 40% of theoretical yield).

[0195] .sup.1H NMR (400 MHz, DMSO-d6) ppm 4.47 (d, J=6.02 Hz, 2H) 5.04 (s, 2H) 7.33-7.41 (m, 4H) 7.50 (d, J=7.78 Hz, 1H) 7.97 (dd, J=8.03, 1.76 Hz, 1H) 8.25 (s, 1H) 9.09 (t, J=6.10 Hz, 1H) 9.30 (s, 1H)

[0196] MS [M+H].sup.+: 302.1/303.1 (rt 1.66-168 min)

Example P11

Preparation of 1-hydroxy-N-methoxy-N-methyl-3H-2,1-benzoxaborole-6-carboxamide

[0197] ##STR00037##

[0198] To a stirred solution of 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylic acid (0.1 g, 0.562 mmol) in dichloromethane (10 mL) were added N,O-dimethylhydroxylamine (0.043 g 0.6743 mmol), Propylphosphonic anhydride (0.282 g, 0.843 mmol) and triethylamine (0.17 g, 1.686 mmol). The reaction mixture was stirred at ambient temperature for 3 h. Reaction mixture was diluted 10 ml water and aqueous layer was then extracted with dichloromethane (250 ml). The combined organic layer was washed with 2N HCl (110 ml), water (210 ml) finally with brine solution (210 ml). The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated completely to afford desired compound 1-hydroxy-N-methoxy-N-methyl-3H-2,1-benzoxaborole-6-carboxamide (0.050 g, 40% of theoretical yield).

[0199] .sup.1H NMR (400 MHz, DMSO-d6) ppm 3.23-3.31 (m, 3H) 3.54 (s, 3H) 5.04 (s, 2H) 7.48 (d, J=8.03 Hz, 1H) 7.69 (d, J=7.53 Hz, 1H) 7.97 (s, 1H) 9.34 (s, 1H)

[0200] MS [M+H].sup.+: 220.7/221.7 (rt 1.27-1.36 min)

[0201] The following tables illustrate the invention:

##STR00038##

[0202] Table 1: This table discloses the 161 specific compounds of the formula A1-a, wherein R.sup.1 is Cl, G has the specific meaning given in the corresponding line appropriately selected from the 161 lines T2.001 to T2.161 of Table T2.

[0203] Table 2: This table discloses the 161 specific compounds of the formula A1-a, wherein R.sup.1 is F, G has the specific meaning given in the corresponding line appropriately selected from the 161 lines T2.001 to T2.161 of Table T2.

[0204] Table 3: This table discloses the 161 specific compounds of the formula A1-a, wherein R.sup.1 is H, G has the specific meaning given in the corresponding line appropriately selected from the 161 lines T2.001 to T2.161 of Table T2.

[0205] Table 4: This table discloses the 161 specific compounds of the formula A1-a, wherein R.sup.1 is OMe, G has the specific meaning given in the corresponding line appropriately selected from the 161 lines T2.001 to T2.161 of Table T2.

[0206] Table 5: This table discloses the 161 specific compounds of the formula A1-a, wherein R.sup.1 is CF3, and G has the specific meaning given in the corresponding line appropriately selected from the 161 lines T2.001 to T2.161 of Table T2.

[0207] Table 6: This table discloses the 161 specific compounds of the formula A1-a, wherein R.sup.1 is CN, G has the specific meaning given in the corresponding line appropriately selected from the 161 lines T2.001 to T2.161 of Table T2.

[0208] Table 7: This table discloses the 161 specific compounds of the formula A1-a, wherein R.sup.1 is Me, G has the specific meaning given in the corresponding line appropriately selected from the 161 lines T2.001 to T2.161 of Table T2.

TABLE-US-00001 TABLE T2 Cmpd No. G R2 R3 R4 T2.001 OR.sup.2 Ethyl T2.002 OR.sup.2 prop-2-ynyl T2.003 OR.sup.2 [00039] T2.004 OR.sup.2 Allyl T2.005 OR.sup.2 Isopropyl T2.006 OR.sup.2 2-F-ethyl T2.007 OR.sup.2 [00040] T2.008 OR.sup.2 but-3-ynyl T2.009 OR.sup.2 but-2-ynyl T2.010 OR.sup.2 [00041] T2.011 OR.sup.2 [00042] T2.012 OR.sup.2 tetrahydrofuran-2-ylmethyl T2.013 OR.sup.2 [00043] T2.014 OR.sup.2 trimethylsilylmethyl T2.015 OR.sup.2 3,3,3-trifluoropropyl T2.016 OR.sup.2 4-methoxy-4-oxo-but-2-ynyl T2.017 OR.sup.2 2-chloro-2,2-difluoro-ethyl T2.018 OR.sup.2 heptyl T2.019 OR.sup.2 2-methylsulfonylethyl T2.020 OR.sup.2 (3-fluorophenyl)methyl T2.021 OR.sup.2 3-trimethylsilylprop-2-ynyl T2.022 OR.sup.2 [00044] T2.023 OR.sup.2 1-methoxycarbonylbut-3-enyl T2.024 OR.sup.2 3-trimethylsilylallyl T2.025 OR.sup.2 1-phenylprop-2-ynyl T2.026 OR.sup.2 3-phenylprop-2-ynyl T2.027 OR.sup.2 tetrahydrothiopyran-4-ylmethyl T2.028 OR.sup.2 6-methoxytetrahydropyran-3-yl T2.029 OR.sup.2 3-trimethylsilylpropyl T2.030 OR.sup.2 2-butylsulfanylethyl T2.031 OR.sup.2 2-(4-chlorophenoxy)ethyl T2.032 OR.sup.2 2-ethoxycarbonylcyclohexyl T2.033 OR.sup.2 6-(trifluoromethyl)-3- pyridyl]methyl T2.034 OR.sup.2 (4-phenylphenyl)methyl T2.035 OR.sup.2 2-(2,6-dichlorophenyl)ethyl T2.036 OR.sup.2 2-(2,4-dichlorophenyl)ethyl T2.037 OR.sup.2 4-(2-naphthyl)butyl T2.038 OR.sup.2 [2-chloro-4- (trifluoromethyl)phenyl]methyl T2.039 OR.sup.2 [3-chloro-5- (trifluoromethyl)2- pyridyl]methyl T2.040 OR.sup.2 (4-oxo-4-pyrrolidin-1-yl-butyl) T2.041 OR.sup.2 1-naphthylmethyl T2.042 OR.sup.2 2-[2-(2- methoxyethoxy)ethoxy]ethyl T2.043 OR.sup.2 (2-methoxy-2-oxo-1-phenyl- ethyl) T2.044 OR.sup.2 2-(4-methoxyphenoxy)ethyl T2.045 OR.sup.2 benzenesulfonylmethyl T2.046 OR.sup.2 phenacyl T2.047 OR.sup.2 cyclobutylmethyl T2.048 OR.sup.2 2-dimethylaminoethyl T2.049 OR.sup.2 thietan-3-yl T2.050 OR.sup.2 [2-fluoro-1- (fluoromethyl)ethyl] T2.051 OR.sup.2 3-(1-methylpyrazol-4- yl)propyl T2.052 OR.sup.2 (2-chlorothiazol-5-yl)methyl T2.053 OR.sup.2 2-dimethoxyphosphorylethyl T2.054 OR.sup.2 1-[ethoxy(methyl) phosphoryl]ethyl T2.055 OR.sup.2 (1-methyl-2-morpholino- ethyl) T2.056 NR.sup.3R.sup.4 ethyl- H T2.057 NR.sup.3R.sup.4 butyl- H T2.058 NR.sup.3R.sup.4 but-2-yl- H T2.059 NR.sup.3R.sup.4 Allyl H T2.060 NR.sup.3R.sup.4 benzyl H T2.061 NR.sup.3R.sup.4 phenyl H T2.062 NR.sup.3R.sup.4 methyl methoxy T2.063 NR.sup.3R.sup.4 methyl H T2.064 NR.sup.3R.sup.4 methyl methyl T2.065 NR.sup.3R.sup.4 (1-methyl-1H-imidazol-4-yl)- H methyl- T2.066 NR.sup.3R.sup.4 (1H-benzimidazol-2-yl)-methyl- H T2.067 NR.sup.3R.sup.4 3-bromo-propyl- H T2.068 NR.sup.3R.sup.4 3,3,3-trifluoro-propyl- H T2.069 NR.sup.3R.sup.4 (1-hydroxycyclohexyl)methyl H T2.070 NR.sup.3R.sup.4 2-oxotetrahydrothiophen-3-yl H T2.071 NR.sup.3R.sup.4 6-ethoxycarbonylcyclohex-3-en-1-yl H T2.072 NR.sup.3R.sup.4 [2-hydroxy-2-(4- H hydroxyphenyl)ethyl] T2.073 NR.sup.3R.sup.4 2-(1,3-benzodioxol-5-yl)ethyl H T2.074 NR.sup.3R.sup.4 2-benzylsulfanylethyl H T2.075 NR.sup.3R.sup.4 4-Methenesulfonyl-benzyl H T2.076 NR.sup.3R.sup.4 N,N-dimethylaminoethyl H T2.077 NR.sup.3R.sup.4 sec-Butyl H T2.078 NR.sup.3R.sup.4 Butan-1-ol-2-yl H T2.079 NR.sup.3R.sup.4 1-methoxy-prop-2-yl- H T2.080 NR.sup.3R.sup.4 2,2-Difluoro-ethyl H T2.081 NR.sup.3R.sup.4 Ethynyl-cyclohexyl H T2.082 NR.sup.3R.sup.4 2-([1,3]dioxolan-2-yl)-eth-1-yl- H T2.083 NR.sup.3R.sup.4 tetrahydrofuran-2-ylmeth-yl- H T2.084 NR.sup.3R.sup.4 2-methyl-cyclohex-1-yl- H T2.085 NR.sup.3R.sup.4 2-Morpholin-4-yl-ethyl H T2.086 NR.sup.3R.sup.4 3-pyrrolidin-1-ylpropyl H T2.087 NR.sup.3R.sup.4 2-sulfosulfanylethyl H T2.088 NR.sup.3R.sup.4 (pyrid-3-yl)-methyl- H T2.089 NR.sup.3R.sup.4 3-(1-piperidyl)propyl H T2.090 NR.sup.3R.sup.4 Benzyl H T2.091 NR.sup.3R.sup.4 3-(4-chlorophenyl)isoxazol-5-ylmethyl H T2.092 NR.sup.3R.sup.4 2-fluoro-phenyl-meth-yl- H T2.093 NR.sup.3R.sup.4 1-phenyl-eth-1-yl- H T2.094 NR.sup.3R.sup.4 2-phenyl-eth-1-yl- H T2.095 NR.sup.3R.sup.4 (1,2,2,6,6-pentamethyl-4-piperidyl H T2.096 NR.sup.3R.sup.4 2-(thiophen-2-yl)-eth-1-yl- H T2.097 NR.sup.3R.sup.4 2-Phenoxy-ethyl H T2.098 NR.sup.3R.sup.4 (3-chloro-phenyl)-methyl- H T2.099 NR.sup.3R.sup.4 (2,3-dihydro-benzo[1,4]dioxin-6-yl)- H methyl- T2.100 NR.sup.3R.sup.4 2-Acetylamino-ethyl H T2.101 NR.sup.3R.sup.4 (4-methoxy-phenyl)-methyl- H T2.102 NR.sup.3R.sup.4 4-Pyrazol-1-yl-benzyl H T2.103 NR.sup.3R.sup.4 (2-trifluoromethoxy-phenyl)-methyl- H T2.104 NR.sup.3R.sup.4 2-(indol-3-yl)-eth-1-yl- H T2.105 NR.sup.3R.sup.4 2-trifluoromethyl-benzyl- H T2.106 NR.sup.3R.sup.4 2-Methylsulfanyl-ethyl H T2.107 NR.sup.3R.sup.4 2-Piperidin-1-yl-benzyl H T2.108 NR.sup.3R.sup.4 4-Phenoxy-benzyl H T2.109 NR.sup.3R.sup.4 (6-Chloro-pyridin-3-yl)-methyl H T2.110 NR.sup.3R.sup.4 1-Benzyl-pyrrolidin-3-yl H T2.111 NR.sup.3R.sup.4 2-Piperidin-1-yl-benzyl H T2.112 NR.sup.3R.sup.4 Furan-2-yl-methyl H T2.113 NR.sup.3R.sup.4 2-chloro-phenyl- H T2.114 NR.sup.3R.sup.4 4-methoxycarbonylphenyl H T2.115 NR.sup.3R.sup.4 4-isopropylphenyl H T2.116 NR.sup.3R.sup.4 2-methyl-phenyl- H T2.117 NR.sup.3R.sup.4 2-chloro-6-methyl-phenyl- H T2.118 NR.sup.3R.sup.4 quinolin-5-yl- H T2.119 NR.sup.3R.sup.4 2,4-dimethoxy-phenyl- H T2.120 NR.sup.3R.sup.4 3-fluoro-phenyl- H T2.121 NR.sup.3R.sup.4 1H-Indazol-5-yl H T2.122 NR.sup.3R.sup.4 3-phenylphenyl H T2.123 NR.sup.3R.sup.4 4-pyrrol-1-ylphenyl H T2.124 NR.sup.3R.sup.4 4-Piperidin-1-yl-phenyl H T2.125 NR.sup.3R.sup.4 (2-benzoylphenyl) H T2.126 NR.sup.3R.sup.4 2-methoxycarbonylbenzothiophen-5-yl H T2.127 NR.sup.3R.sup.4 2-methoxy-5-phenyl-phenyl H T2.128 NR.sup.3R.sup.4 2-methylsulfanylphenyl H T2.129 NR.sup.3R.sup.4 1,3-benzothiazol-6-yl H T2.130 NR.sup.3R.sup.4 2-morpholino-5- H (trifluoromethyl)phenyl T2.131 NR.sup.3R.sup.4 2-(1H-indol-2-yl)phenyl H T2.132 NR.sup.3R.sup.4 2-morpholinophenyl H T2.133 NR.sup.3R.sup.4 4-Methyl-2-oxo-2H-chromen-7-yl H T2.134 NR.sup.3R.sup.4 4-(dimethylsulfamoyl)phenyl H T2.135 NR.sup.3R.sup.4 4-(2-pyridylsulfamoyl)phenyl H T2.136 NR.sup.3R.sup.4 1,3-dimethyl-1H-pyrazol-5-yl- H T2.137 NR.sup.3R.sup.4 4-methylthiazol-2-yl H T2.138 NR.sup.3R.sup.4 5-methylsulfanyl-1H-[1,2,4]-triazol-3-yl H T2.139 NR.sup.3R.sup.4 3-methyl-2-pyridyl H T2.140 NR.sup.3R.sup.4 4-methyl-6-methylsulfanyl-1,3,5- H triazin-2-yl T2.141 NR.sup.3R.sup.4 4-hydroxy-6-methyl-pyrimidin-2-yl H T2.142 NR.sup.3R.sup.4 5-methoxycarbonyl-2-pyridyl H T2.143 NR.sup.3R.sup.4 Quinolin-2-yl H T2.144 NR.sup.3R.sup.4 5-methyl-3-phenyl-isoxazol-4-yl H T2.145 NR.sup.3R.sup.4 9H-Purin-6-yl H T2.146 NR.sup.3R.sup.4 5-acetyl-4-methyl-thiazol-2-yl H T2.147 NR.sup.3R.sup.4 5-phenyl-1H-pyrazol-3-yl H T2.148 NR.sup.3R.sup.4 4-methyl-1,3-benzothiazol-2-yl H T2.149 NR.sup.3R.sup.4 5-methyl-1,3,4-thiadiazol-2-yl H T2.150 NR.sup.3R.sup.4 4-(4-chlorophenyl)thiadiazol-5-yl H T2.151 NR.sup.3R.sup.4 6-phenoxy-3-pyridyl H T2.152 NR.sup.3R.sup.4 3-cyano-5-phenyl-2-furyl H T2.153 NR.sup.3R.sup.4 4-cyano-2-phenyl-pyrazol-3-yl H T2.154 NR.sup.3R.sup.4 3-ethoxycarbonyl-4,5,6,7- H tetrahydrobenzothiophen-2-yl T2.155 NR.sup.3R.sup.4 2-methoxycarbonyl-3-thienyl H T2.156 NR.sup.3R.sup.4 4-methyl-6-(2-thienyl)pyrimidin-2-yl H T2.157 NR.sup.3R.sup.4 4,6-dimethyl-2H-pyrazolo[3,4- H b]pyridin-3-yl T2.158 NR.sup.3R.sup.4 4-(p-tolyl)thiazol-2-yl H T2.159 NR.sup.3R.sup.4 5-phenyl-2-pyridyl H T2.160 NR.sup.3R.sup.4 CH2CH2OCH2CH2 T2.161 NR.sup.3R.sup.4 CH2CH2NHCH2CH2

TABLE-US-00002 TABLE T1 Table of selected examples The compounds in Table T1 the flowing formula: [00045] and the substituents have the meaning as follows: Cpd.No. G R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 m.p. ( C.) 1 OR.sup.2 H H 2 NR.sup.2R.sup.3 Cl H 4-ClPh 201-203 3 OR.sup.2 Cl CH.sub.3CH.sub.2 129-131 4 OR.sup.2 F H 216-218 5 OR.sup.2 F CH.sub.3CH.sub.2 149-151 6 NR.sup.2R.sup.3 F H 4-ClPh 207-209 7 NR.sup.2R.sup.3 F H 4-ClCH.sub.2Ph 179-181 8 NR.sup.2R.sup.3 F H 4-CNCH.sub.2Ph 187-189 9 NR.sup.2R.sup.3 H H 4-CNCH.sub.2Ph 136-138 10 NR.sup.2R.sup.3 H H 4-ClCH.sub.2Ph 198-200 11 OR2 Cl H 220-222 12 NR.sup.2R.sup.3 Cl H 4-FCH.sub.2Ph 13 NR.sup.2R.sup.3 F H 4-FPh 182-184 14 NR.sup.2R.sup.3 F H 4-FCH.sub.2Ph 179-181 15 NR.sup.2R.sup.3 Cl H 4-FPh 16 OR.sup.2 H CH.sub.3 167-169 17 OR.sup.2 H CH.sub.3CH.sub.2 150-152 18 OR.sup.2 H CF.sub.3CH.sub.2 120-122 19 OR.sup.2 Cl CF.sub.3CH.sub.2 123-125 20 OR.sup.2 F CF.sub.3CH.sub.2 124-126 21 OR.sup.2 Cl CH.sub.3 162-164 22 NR.sup.2R.sup.3 Cl CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 206-208 23 OR.sup.2 F CH.sub.3 168-170 24 NR.sup.2R.sup.3 Cl H CH.sub.2CHCH.sub.2 138-140 25 NR.sup.2R.sup.3 Cl CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2 26 NR.sup.2R.sup.3 F H 4-CF.sub.3Ph 183-188 27 NR.sup.2R.sup.3 F H 2,4-FPh 165-171 28 NR.sup.2R.sup.3 H CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 144-146 29 NR.sup.2R.sup.3 H H 4-ClPh 216-218 30 NR.sup.2R.sup.3 H H 4-FPh 210-212 31 NR.sup.2R.sup.3 H H 2,4-FPh 32 NR.sup.2R.sup.3 H CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2 33 NR.sup.2R.sup.3 Cl H CH.sub.3 34 NR.sup.2R.sup.3 H H CH.sub.3 35 NR.sup.2R.sup.3 H CH.sub.3 CH.sub.3O 169-171 36 NR.sup.2R.sup.3 H CH.sub.3 CH.sub.3O 136-138 37 OR.sup.2 Cl CH.sub.3CH.sub.2CH.sub.2 38 NR.sup.2R.sup.3 H H CH.sub.3O 39 OR.sup.2 H CH.sub.3CH.sub.2CH.sub.2 98-100 40 OR.sup.2 Cl (CH.sub.3).sub.2CH 108-110 41 OR.sup.2 Cl (CH.sub.3).sub.2CH 116-118 MS LCMS Cpd.No. [M + H].sup.+ R.sub.t (min) method 1H-NMR data: ppm (multiplicity/number of Hs) 1 177 1.07-1.10 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.91- 5.03 (m, 1H) 5.05 (s, 2H) 7.45-7.58 (m, 1H) 7.98-8.10 (m, 1H) 8.39-8.41 (m, 1H) 8.63-10.03 (m, 1H) 11.60-14.04 (m, 1H) 2 321.9 1.82-1.82 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.05 (s, 2H) 7.36-7.49 (m, 2H) 7.67 (s, 1H) 7.71-7.80 (m, 2H) 7.88 (s, 1H) 9.44 (br. s., 1H) 10.66 (s, 1H) 3 241.1 1.68-1.73 M2 1H NMR (400 MHz, DMSO-d6) ppm 1.33 (t, J = 7.03 Hz, 3H) 4.34 (q, J = 7.03 Hz, 2H) 5.03 (s, 2H) 7.67 (s, 1H) 8.16 (s, 1H) 9.46 (s, 1H) 4 195 1.08-1.11 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.02 (s, 2H) 7.37 (d, J = 11.29 Hz, 1H) 8.29 (d, J = 7.53 Hz, 1H) 9.38 (s, 1H) 13.17 (br. s., 1H) 5 225.1 1.57-1.60 M2 1H NMR (400 MHz, DMSO-d6) ppm 1.32 (t, J = 7.03 Hz, 3H) 4.33 (q, J = 7.19 Hz, 2H) 5.03 (s, 2H) 7.41 (d, J = 11.29 Hz, 1H) 8.30 (d, J = 7.53 Hz, 1H) 9.42 (s, 1H) 6 306 1.79-1.81 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.05 (s, 2H) 7.40-7.45 (m, 3H) 7.76 (d, J = 7.99 Hz, 2H) 8.01 (d, J = 7.03 Hz, 1H) 9.39 (s, 1H) 10.57 (s, 1H) 7 320 1.73-1.75 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.46 (d, J = 6.02 Hz, 2H) 5.02 (s, 2H) 7.34-7.43 (m, 5H) 8.00 (d, J = 7.28 Hz, 1H) 8.92 (t, J = 6.17 Hz, 1H) 9.35 (s, 1H) 8 311 1.50-1.53 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.56 (d, J = 6.02 Hz, 2H) 5.02 (s, 2H) 7.38 (d, J = 10.79 Hz, 1H) 7.53 (m, J = 8.28 Hz, 2H) 7.77-7.89 (m, 2H) 8.03 (d, J = 7.28 Hz, 1H) 9.00 (t, J = 6.00 Hz, 1H) 9.35 (br. s., 1H) 9 293.1 1.44-1.48 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.52 (d, J = 6.02 Hz, 3H) 5.01 (s, 2H) 7.48 (d, J = 7.63 Hz, 4H) 7.71-7.78 (m, 3H) 7.95 (dd, J = 8.03, 1.76 Hz, 1H) 8.23 (d, J = 0.75 Hz, 1H) 9.14 (t, J = 5.87 Hz, 1H) 9.27 (s, 1H) 10 302.1 1.66-1.68 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.47 (d, J = 6.02 Hz, 2H) 5.04 (s, 2H) 7.33-7.41 (m, 4H) 7.50 (d, J = 7.78 Hz, 1H) 7.97 (dd, J = 8.03, 1.76 Hz, 1H) 8.25 (s, 1H) 9.09 (t, J = 6.10 Hz, 1H) 9.30 (s, 1H) 11 211 1.16-1.22 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.02 (s, 2H) 7.63 (s, 1H) 8.16 (s, 1H) 9.42 (s, 1H) 13.29 (br. s., 1H) 12 320 1.64-1.67 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.44 (d, J = 6.02 Hz, 2H) 5.01 (s, 2H) 7.15-7.26 (m, 2H) 7.37-7.45 (m, 2H) 7.59 (s, 1H) 7.77 (s, 1H) 9.00 (t, J = 5.98 Hz, 1H) 9.38 (s, 1H) 13 290.1 1.65-1.69 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.00- 5.10 (m, 2H) 7.20 (t, J = 8.36 Hz, 2H) 7.42 (d, J = 10.54 Hz, 1H) 7.70-7.80 (m, 2H) 8.01 (d, J = 7.03 Hz, 1H) 9.39 (br. s., 1H) 10.48 (s, 1H) 14 304.1 1.63-1.65 M2 1H NMR (400 MHz, DMSO-d6) ppm 4.40- 4.50 (m, 3H) 5.02 (s, 2H) 7.09-7.26 (m, 3H) 7.33-7.41 (m, 4H) 7.99 (d, J = 7.28 Hz, 1H) 8.90 (t, J = 5.95 Hz, 1H) 9.34 (br. s., 1H) 15 306 1.68-1.72 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.05 (s, 2H) 7.20 (t, J = 8.02 Hz, 2H) 7.66 (s, 1H) 7.74 (t, J = 6.31 Hz, 3H) 7.87 (s, 1H) 9.45 (s, 1H) 10.57 (s, 1H) 16 193.1 1.38-1.42 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.84- 3.92 (m, 3H) 5.07 (s, 2H) 7.56 (d, J = 8.03 Hz, 1H) 8.02-8.12 (m, 1H) 8.41 (s, 1H) 9.39 (s, 1H) 17 207.1 1.56-1.60 M2 1H NMR (400 MHz, DMSO-d6) ppm 1.18- 1.37 (m, 3H) 4.34 (q, J = 7.03 Hz, 2H) 5.07 (s, 2H) 7.56 (d, J = 7.91 Hz, 1H) 8.07 (dd, J = 7.91, 1.63 Hz, 1H) 8.41 (dd, J = 1.51, 0.75 Hz, 1H) 9.39 (s, 1H) 18 261.1 1.76-1.78 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.00- 5.11 (m, 4H) 7.62 (d, J = 7.85 Hz, 1H) 8.10 (dd, J = 8.03, 1.51 Hz, 1H) 8.45 (d, J = 1.00 Hz, 1H) 9.47 (s, 1H) 19 294.9 1.82-1.88 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.01- 5.10 (m, 4H) 7.74 (s, 1H) 8.28 (s, 1H) 9.57 (s, 1H) 20 277 1.73-1.78 M2 1H NMR (400 MHz, CHLOROFORM-d) ppm 5.04-5.13 (m, 4H) 7.52 (s, 1H) 7.55 (s, 1H) 8.42 (d, J = 7.53 Hz, 1H) 9.57 (s, 1H) 21 227 1.54-1.60 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.88 (s, 3H) 5.03 (s, 2H) 7.67 (s, 1H) 8.18 (s, 1H) 9.46 (s, 1H) 22 206-208 281.9 1.20-1.27 M2 23 210.9 1.35-1.39 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.87 (s, 3H) 5.04 (s, 2H) 7.43 (d, J = 11.04 Hz, 1H) 8.32 (d, J = 7.53 Hz, 1H) 9.43 (s, 1H) 24 252 1.27-1.30 M2 1H NMR (400 MHz, CHLOROFORM-d) ppm 3.90-3.97 (m, 2H) 5.07 (s, 2H) 5.15- 5.21 (m, 1H) 5.28-5.36 (m, 1H) 5.90- 6.00 (m, 1H) 7.64 (s, 1H) 7.82 (s, 1H) 8.68 (t, J = 5.77 Hz, 1H) 9.44 (s, 1H) 25 280 1.51-1.55 M2 26 339.9 1.83-1.87 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.06 (s, 2H) 7.45 (d, J = 10.29 Hz, 1H) 7.74 (m, J = 8.53 Hz, 2H) 7.95 (m, J = 8.53 Hz, 2H) 8.04 (d, J = 8.22 Hz, 1H) 9.41 (s, 1H) 10.81 (s, 1H) 27 308 1.63-1.67 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.06 (s, 2H) 7.09-7.25 (m, 1H) 7.25-7.47 (m, 3H) 7.76 (d, J = 6.53 Hz, 2H) 8.09 (d, J = 7.28 Hz, 1H) 9.39 (s, 1H) 10.16 (s, 1H) 28 144-146 248 1.00-1.06 M2 29 287.9 1.70-1.75 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.08 (s, 2H) 7.38-7.46 (m, 2H) 7.57 (d, J = 8.03 Hz, 1H) 7.81-7.87 (m, 2H) 8.05 (d, J = 8.14 Hz, 1H) 8.31-8.34 (m, 1H) 9.37 (br. s., 1H) 10.44 (s, 1H) 30 272 1.55-1.59 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.08 (s, 2H) 6.57-6.63 (m, 1H) 6.87 (t, J = 8.18 Hz, 1H) 7.04-7.24 (m, 3H) 7.56 (d, J = 8.03 Hz, 1H) 7.72-7.90 (m, 2H) 8.04 (dd, J = 8.03, 1.76 Hz, 1H) 8.32 (s, 1H) 10.37 (s, 1H) 31 290 1.52-1.58 M2 1H NMR (400 MHz, DMSO-d6) ppm 5.08 (s, 2H) 7.10-7.15 (m, 1H) 7.33-7.37 (m, 1H) 7.55-7.64 (m, 3H) 8.06 (dd, J = 7.91, 1.63 Hz, 1H) 8.34 (s, 1H) 9.36 (br. s., 1H) 10.17 (s, 1H) 32 246 1.37-1.45 M2 33 225.9 0.96-0.99 M2 1H NMR (400 MHz, DMSO-d6) ppm 2.55- 2.62 (m, 4H) 4.81-4.85 (m, 2H) 7.40 (s, 1H) 7.55 (s, 1H) 8.17 (d, J = 4.77 Hz, 1H) 9.21 (br. s., 1H) 34 192 0.74-0.79 M2 1H NMR (400 MHz, DMSO-d6) ppm 2.79 (d, J = 4.52 Hz, 3H) 5.01-5.06 (m, 2H) 7.47 (d, J = 8.03 Hz, 1H) 7.91 (dd, J = 7.91, 1.63 Hz, 1H) 8.21 (s, 1H) 8.44 (d, J = 6.03 Hz, 1H) 9.29 (s, 1H) 35 2559.9 1.27-1.48 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.30 (br. s., 3H) 3.36 (br. s., 1H) 3.42 (br. s., 3H) 5.03 (s, 2H) 7.61 (s, 1H) 7.71 (s, 1H) 9.39 (br. s., 1H) 36 221.7 1.27-1.36 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.23- 3.31 (m, 3H) 3.54 (s, 3H) 5.04 (s, 2H) 7.48 (d, J = 8.03 Hz, 1H) 7.69 (d, J = 7.53 Hz, 1H) 7.97 (s, 1H) 9.34 (br. 37 254.8 1.96-1.98 M2 1H NMR (400 MHz, DMSO-d6) ppm 0.78- 0.92 (m, 1H) 0.99 (t, J = 7.40 Hz, 3H) 1.74 (sxt, J = 7.08 Hz, 2H) 4.27 (t, J = 6.53 Hz, 2H) 5.04 (s, 2H) 7.67 (s, 1H) 8.17 (s, 1H) 9.49 (br. s., 1H) 38 207.8 0.46-0.5 M2 1H NMR (400 MHz, DMSO-d6) ppm 3.67- 3.75 (m, 3H) 5.04 (s, 2H) 7.50 (d, J = 8.03 Hz, 1H) 7.83 (d, J = 7.78 Hz, 1H) 8.14 (s, 1H) 9.33 (br. s., 1H) 11.74 (br. s., 1H) 39 220.9 1.83-2.1 M2 1H NMR (400 MHz, DMSO-d6) ppm 1.00 (t, J = 7.40 Hz, 4H) 1.70-1.79 (m, 2H) 4.25 (t, J = 6.53 Hz, 2H) 5.07 (s, 2H) 7.56 (d, J = 8.03 Hz, 1H) 8.07 (d, J = 7.74 Hz, 1H) 8.41 (s, 1H) 9.41 (s, 1H) 40 220.9 1.81-2.1 M2 1H NMR (400 MHz, DMSO-d6) ppm 1.36- 1.44 (m, 8H) 5.12 (s, 2H) 5.17-5.27 (m, 1H) 7.61 (d, J = 8.28 Hz, 1H) 8.11 (dd, J = 8.03, 1.51 Hz, 1H) 8.44 (s, 1H) 9.45 (s, 1H) 41 254.9 1.90-2.1 M2 1H NMR (400 MHz, DMSO-d6) ppm 1.35 (d, J = 6.27 Hz, 6H) 4.94-5.08 (m, 2H) 5.11-5.27 (m, 1H) 7.59-7.83 (m, 1H) 8.01-8.27 (m, 1H) 9.47 (s, 1

TABLE-US-00003 TABLE T1-A Table of further selected examples Entry STRUCTURE RT (min) [M + H] (measured) Method MP C. 50 [00046] 130-132 51 [00047] 144-146 52 [00048] 53 [00049] 150-152 54 [00050] 55 [00051] 56 [00052] 57 [00053] 58 [00054] 59 [00055] 60 [00056] 61 [00057] 62 [00058] 63 [00059] 64 [00060] 65 [00061] 66 [00062] 67 [00063] 68 [00064] 69 [00065] 70 [00066] 71 [00067] 72 [00068] 73 [00069] 74 [00070] 75 [00071] 76 [00072] 77 [00073] 78 [00074] 79 [00075] 80 [00076] 81 [00077] 82 [00078] 83 [00079] 84 [00080] 85 [00081] 263-265 86 [00082] 87 [00083] 88 [00084] 89 [00085] 90 [00086] 91 [00087] 92 [00088] 93 [00089] 94 [00090] 95 [00091] 96 [00092] 97 [00093] 98 [00094] 99 [00095] 100 [00096] 101 [00097] 102 [00098] 103 [00099] 104 [00100] 105 [00101] 106 [00102] 107 [00103] 175-177 108 [00104] 109 [00105] 110 [00106] 111 [00107] 112 [00108] 113 [00109] 114 [00110] 115 [00111] 116 [00112] 117 [00113] 118 [00114] 119 [00115] 120 [00116] 121 [00117] 122 [00118] 123 [00119] 124 [00120] 125 [00121] 126 [00122] 127 [00123] 128 [00124] 129 [00125] 130 [00126] 131 [00127] 132 [00128] 133 [00129] 134 [00130] 135 [00131] 136 [00132] 178-180 137 [00133] 138 [00134] 139 [00135] 140 [00136] 141 [00137] 142 [00138] 143 [00139] 144 [00140] 158-160 145 [00141] 146 [00142] 184-186 147 [00143] 148 [00144] 149 [00145] 150 [00146] 212-214 151 [00147] 152 [00148] 153 [00149] 154 [00150] 155 [00151] 156 [00152] 157 [00153] 158 [00154] 159 [00155] 160 [00156] 161 [00157] 162 [00158] 163 [00159] 164 [00160] 165 [00161] 166 [00162] 167 [00163] 168 [00164] 169 [00165] 267-269 170 [00166] 171 [00167] 172 [00168] 173 [00169] 174 [00170] 175 [00171] 176 [00172] 177 [00173] 178 [00174] 179 [00175] 180 [00176] 181 [00177] 182 [00178] 183 [00179] 184 [00180] 185 [00181] 186 [00182] 302-304 187 [00183] 188 [00184] 189 [00185] 190 [00186] 191 [00187] 192 [00188] 193 [00189] 194 [00190] 195 [00191] 196 [00192] 197 [00193] 198 [00194] 199 [00195] 200 [00196] 201 [00197] 202 [00198] 203 [00199] 204 [00200] 205 [00201] 206 [00202] 207 [00203] 208 [00204] 209 [00205] 210 [00206] 211 [00207] 212 [00208] 213 [00209] 214 [00210] 215 [00211] 216 [00212] 217 [00213] 218 [00214] 219 [00215] 220 [00216] 221 [00217] 222 [00218] 223 [00219] 224 [00220] 225 [00221] 115-117 226 [00222] 227 [00223] 228 [00224] 229 [00225] 230 [00226] 231 [00227] 232 [00228] 233 [00229] 234 [00230] 235 [00231] 236 [00232] 237 [00233] 238 [00234] 239 [00235] 240 [00236] 241 [00237] 242 [00238] 148-150 243 [00239] 274-276 244 [00240] 122-124 245 [00241] 246 [00242] 247 [00243] 248 [00244] 249 [00245] 250 [00246] 251 [00247] 252 [00248] 253 [00249] 254 [00250] 255 [00251] 256 [00252] 257 [00253] 258 [00254] 259 [00255] 260 [00256] 261 [00257] 262 [00258] 263 [00259] 264 [00260] 265 [00261] 266 [00262] 267 [00263] 268 [00264] 269 [00265] 270 [00266] 271 [00267] 272 [00268] 273 [00269] 274 [00270] 275 [00271] 276 [00272] 277 [00273] 278 [00274] 279 [00275] 280 [00276] 281 [00277] 282 [00278] 283 [00279] 284 [00280] 285 [00281] 286 [00282] 287 [00283] 288 [00284] 289 [00285] 290 [00286] 291 [00287] 292 [00288] 293 [00289] 294 [00290] 295 [00291] 296 [00292] 297 [00293] 298 [00294] 299 [00295] 300 [00296] 301 [00297] 302 [00298] 303 [00299] 304 [00300] 305 [00301] 306 [00302] 307 [00303] 308 [00304] 309 [00305] 310 [00306] 311 [00307] 312 [00308] 313 [00309] 314 [00310] 315 [00311] 316 [00312] 317 [00313] 318 [00314] 319 [00315] 320 [00316] 321 [00317] 322 [00318] 323 [00319] 154-155 324 [00320] 325 [00321] 326 [00322] 327 [00323] 328 [00324] 329 [00325] 330 [00326] 331 [00327] 332 [00328] 333 [00329] 334 [00330] 335 [00331] 336 [00332] 337 [00333] 338 [00334] 339 [00335] 340 [00336] 341 [00337] 342 [00338] 343 [00339] 344 [00340] 345 [00341] 346 [00342] 347 [00343] 348 [00344] 349 [00345] 350 [00346] 351 [00347] 352 [00348] 122-124 353 [00349] 354 [00350] 355 [00351] 356 [00352] 357 [00353] 358 [00354] 359 [00355] 360 [00356] 361 [00357] 362 [00358] 363 [00359] 364 [00360] 365 [00361] 366 [00362] 367 [00363] 368 [00364] 369 [00365] 370 [00366] 371 [00367] 372 [00368] 373 [00369] 374 [00370] 375 [00371] 125-127 376 [00372] 377 [00373] 378 [00374] 379 [00375] 380 [00376] 381 [00377] 382 [00378] 383 [00379] 384 [00380] 385 [00381] 386 [00382] 387 [00383] 388 [00384] 389 [00385] 107-109 390 [00386] 391 [00387] 392 [00388] 393 [00389] 394 [00390] 395 [00391] 396 [00392] 397 [00393] 398 [00394] 399 [00395] 400 [00396] 401 [00397] 402 [00398] 403 [00399] 404 [00400] 405 [00401] 406 [00402] 407 [00403] 408 [00404] 409 [00405] 410 [00406] 411 [00407] 412 [00408] 413 [00409] 414 [00410] 415 [00411] 416 [00412] 417 [00413] 418 [00414] 419 [00415] 112-114 420 [00416] 421 [00417] 422 [00418] 423 [00419] 424 [00420] 112-114 425 [00421] 426 [00422] 427 [00423] 428 [00424] 429 [00425] 122-124 430 [00426] 431 [00427] 432 [00428] 433 [00429] 434 [00430] 435 [00431] 150-152 436 [00432] 216-218 439 [00433] 440 [00434] 270-272 441 [00435] 128-130 442 [00436] 213-215 443 [00437] 110-112 444 [00438] 109-111 445 [00439] 108-110 446 [00440] 136-138 447 [00441] 110-112 448 [00442] 122-124 449 [00443] 122-124 450 [00444] 134-136 451 [00445] 102-104

Characterising Data:

[0209] Table 2 shows all the prepared examples with selected melting point and selected NMR data for prepared compounds. CDCl.sub.3/D.sub.2O and DMSO are used as solvents for NMR 400 MHz measurements. No attempt is made to list all characterising data in all cases.

[0210] In Table 2 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:

TABLE-US-00004 m.p. = melting point b.p. = boiling point. S = Singlet br = broad d = Doublet dd = doublet of doublets t = Triplet q = quartet m = Multiplet ppm = parts per million

[0211] The following LC-MS methods were used to characterize the compounds:

MethodM 1

[0212] ACQUITY SQD Mass Spectrometer from Waters (Single quadrupole mass spectrometer)
Ionisation method: Electrospray
Polarity: positive ions

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

[0213] Mass range: 100 to 800 Da
DAD Wavelength range (nm): 210 to 400
Method Waters ACQUITY UPLC with the following HPLC gradient conditions
(Solvent A: Water/Methanol 9:1, 0.1% formic acid and Solvent B: Acetonitrile, 0.1% formic acid)

TABLE-US-00005 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

[0214] 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.

[0215] 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 3.

MethodM2

Instrumentation:

[0216] Mass Spectrometer: 6410 Triple quadrupole Mass Spectrometer from Agilent Technologies

HPLC: Agilent 1200 Series HPLC

Optimized Mass Parameter:

[0217] Ionisation method: Electrospray (ESI)
Polarity: positive and Negative Polarity Switch

Scan Type: MS2 Scan

Capillary (kV): 4.00

Fragmentor (V): 100.00

Gas Temperature ( C.): 350

Gas Flow (L/min): 11

[0218] Nebulizer Gas (psi): 35
Mass range: 110 to 1000 Da
DAD Wavelength range (nm): 190 to 400
Optimized Chromatographic parameter
Gradient conditions
(Solvent A: Water, 0.1% formic acid and Solvent B: Acetonitrile, 0.1% formic acid)

TABLE-US-00006 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

[0219] 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.

[0220] Table 5 shows selected melting point and selected NMR data for compounds of Table 1. CDCl.sub.3/D.sub.2O and DMSO are used as solvents for NMR 400 MHz measurements. No attempt is made to list all characterising data in all cases.

[0221] Table 5 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:

TABLE-US-00007 m.p. = melting point b.p. = boiling point. S = Singlet br = broad d = Doublet dd = doublet of doublets t = Triplet q = quartet m = Multiplet ppm = parts per million

[0222] The following LC-MS methode was used to characterize the compounds:

ACQUITY SQD Mass Spectrometer from Waters (Single quadrupole mass spectrometer)
Ionisation method: Electrospray
Polarity: positive ions

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

[0223] Mass range: 100 to 800 Da
DAD Wavelength range (nm): 210 to 400
Method Waters ACQUITY UPLC with the following HPLC gradient conditions
(Solvent A: Water/Methanol 9:1, 0.1% ic acid and Solvent B: Acetonitrile, 0.1% ic acid)

TABLE-US-00008 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

[0224] 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.

[0225] 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 T1.

[0226] Formulation examples for compounds of formula (I):

Example F-1.1 to F-1.2

Emulsifiable Concentrates

[0227]

TABLE-US-00009 Components F-2.1 F-2.2 A compound selected from the Table T1, 25% 50% T1-A or from the Tables 1 to 7 calciumdodecylbenzenesulfonate 5% 6% castoroilpolyethyleneglycolether (36 molethylenoxyunits) 5% tributylphenolpolyethyleneglycolether (30 molethylenoxyunits) cyclohexanone 20% xylenemixture 65% 20%

[0228] Emulsions of any desired concentration can be prepared by diluting such concentrates with water.

Example F-2

Emulsifiable Concentrate

[0229]

TABLE-US-00010 Components F-2 A compound selected from the Table T1, 10% T1-A or from the Tables 1 to 7 octylphenolpolyethyleneglycolether 3% (4 to 5 mol ethylenoxy units) Calcium dodecylbenzenesulfonate 3% Castoroilpolyglycolether 4% (36 mol ethylenoxy units) cyclohexanone 30% xylenemixture 50%

[0230] Emulsions of any desired concentration can be prepared by diluting such concentrates with water.

Examples F-3.1 to F-3.4

Solutions

[0231]

TABLE-US-00011 Components F-3.1 F-3.2 F-3.3 F-3.4 A compound selected from the Table T1, 80% 10% 5% 95% T1-A or from the Tables 1 to 7 propylene glycol monomethyl ether 20% polyethylene glycol 70% (relative 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

[0232]

TABLE-US-00012 Components F-4.1 F-4.2 F-4.3 F-4.4 A compound selected from the Table T1, 5% 10% 8% 21% T1-A or from the Tables 1 to 7 Kaolin 94% 79% 54% highly dispersed silicic acid 1% 13% 7% Attapulgite 90% 18%

[0233] 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

[0234]

TABLE-US-00013 Components F-5.1 F-5.2 A compound selected from the Table T1, 2% 5% T1-A or from the Tables 1 to 7 highly dispersed silicic acid 1% 5% Talcum 97% Kaolin 90%

[0235] Ready for use dusts are obtained by intimately mixing all components.

Examples F-6.1 to F-6.3

Wettable Powders

[0236]

TABLE-US-00014 Components F-6.1 F-6.2 F-6.3 A compound selected from the Table T1, 25% 50% 75% T1-A or from the Tables 1 to 7 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%

[0237] 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

[0238]

TABLE-US-00015 Components F-7 A compound selected from the Table 40% T1, T1-A or from the Tables 1 to 7 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%

[0239] 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

[0240] 1. Phytophthora infestans/Tomato/Leaf Disc Preventative (Late Blight)

[0241] 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 (5-7 days after application). The compounds 16, 21, 23, 27, 59, 78, 84, 85, 87, 90, 94, 107, 114, 119, 121, 124, 128, 129, 132, 138, 150, 163, 181, 182, 186, 193, 202, 206, 207, 208, 211, 217, 231, 236 and 323 (from table T1 and T1-A) 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.

[0242] 2. Plasmopara viticola/Grape/Leaf Disc Preventative (Late Blight)

[0243] 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). The compounds 6, 7, 10, 16, 21, 23, 26, 43, 45, 50, 73, 84, 85, 95, 103, 107, 109, 114, 119, 121, 124, 132, 143, 144, 155, 161, 169, 170, 174, 179, 182, 184, 185, 186, 188, 192, 196, 201, 208, 211, 213, 223, 226, 230, 232, 238, 240, 261, 262, 268, 271, 273, 279, 283, 285, 289, 292, 298, 306, 308, 311, 314, 317, 318, 320, 323, 324, 327, 328, 329, 330, 332, 334, 335, 336, 337, 338, 339, 340, 341, 342, 343, 344, 345, 348, 349, 351, 355, 356, 357, 359, 360, 361, 364, 365, 366, 367, 368, 373, 374, 376, 379, 380, 381, 382, 388, 390, 392, 393, 394, 395, 396, 397, 398, 399, 400, 401, 403, 409, 410, 411, 412, 417, 418, 419, 420, 423, 424, 425, 429, 430, 433, 434, 439, 441, 450 and 451 (from table T1 and T1-A) 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.

[0244] 3. Puccinia recondita f. sp. tritici/Wheat/Leaf Disc Preventative (Brown Rust):

[0245] Wheat leaf segments cultivated variety (cv) Kanzler were placed on agar in 24-well plates 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 1 day after application. The inoculated leaf segments were incubated at 19 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 segments (7-9 days after application).) The compounds 6, 7, 16, 21, 23, 26, 50, 161, 169, 188, 207, 225, 312, 317, 331, 349, 356, 367, 370, 380, 391, 419 and 441 (from table T1 and T1-A) 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.

[0246] 4. Puccinia recondita f. sp. tritici/Wheat/Leaf Disc Curative (Brown Rust)

[0247] 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. The Compounds 21, 23, 40, 230, 233, 339, 348, 351, 355, 356, 365, 393, 401, 402, 418, and 419 (from table T1 and T1-A) 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.

[0248] 5. Phaeosphaeria nodorum (Septoria nodorum)/Wheat/Leaf Disc Preventative (Glume Blotch):

[0249] 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). The Compounds 16, 21, 23, 110, 161, 202, 208, 232, 233, 318, 351 and 446 (from table T1 and T1-A) 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.

[0250] 6. Magnaporthe grisea (Pyricularia oryzae)/Rice/Leaf Disc Preventative (Rice Blast):

[0251] 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). The Compound 21 (from table T1 and T1-A) 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.

[0252] 7. Pyrenophora teres/Barley/Leaf Disc Preventative (Net Blotch):

[0253] 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). The Compounds (from table T1 and T1-A) 16 and 23 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.

[0254] 8. Alternaria solani/Tomato/Leaf Disc (Early Blight)

[0255] Tomato leaf disks cultivated variety (cv.) Baby were placed on 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 2 days after application. The inoculated leaf disks were incubated at 23 C./21 C. (day/night) 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 on untreated check disk leaf disks (5-7 days after application). The Compounds (from table T1 and T1-A) 21 and 23 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.

[0256] 9. Pythium ultimum/Liquid Culture (Seedling Damping Off)

[0257] 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. The Compounds 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 12, 13, 14, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 44, 50, 51, 52, 53, 54, 55, 58, 59, 62, 64, 70, 71, 72, 73, 74, 75, 76, 78, 81, 82, 83, 84, 85, 86, 87, 90, 91, 92, 93, 94, 97, 99, 101, 103, 104, 105, 107, 108, 109, 111, 115, 117, 118, 119, 120, 121, 124, 125, 126, 128, 129, 130, 132, 134, 135, 136, 138, 139, 143, 144, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 163, 164, 166, 170, 172, 173, 174, 175, 176, 177, 178, 179, 180, 181, 182, 184, 185, 186, 189, 192, 193, 196, 197, 198, 201, 202, 203, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 228, 229, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 240, 241, 242, 243, 244, 246, 247, 248, 249, 254, 255, 256, 259, 261, 262, 263, 267, 268, 269, 271, 272, 273, 274, 275, 276, 278, 279, 280, 281, 283, 285, 287, 288, 289, 292, 293, 295, 296, 298, 299, 300, 301, 302, 303, 305, 306, 309, 311, 314, 315, 316, 317, 318, 319, 320, 321, 322, 323, 324, 327, 328, 329, 330, 331, 332, 333, 334, 335, 336, 337, 338, 339, 340, 341, 342, 343, 344, 345, 346, 347, 348, 349, 350, 351, 352, 355, 356, 357, 358, 359, 360, 361, 362, 363, 364, 365, 366, 367, 368, 369, 370, 371, 372, 374, 375, 376, 377, 378, 379, 380, 381, 382, 383, 384, 386, 387, 388, 389, 390, 391, 392, 393, 394, 395, 396, 397, 398, 399, 400, 401, 402, 403, 404, 405, 406, 407, 408, 409, 410, 411, 412, 413, 414, 416, 417, 418, 419, 420, 421, 422, 423, 424, 425, 426, 427, 428, 429, 430, 431, 432, 434, 436, 438, 439, 440, 441, 442, 443, 444, 445, 446, 447, 448, 449, 450 and 451 (from table T1 and T1-A) 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.

[0258] 10. Botryotinia fuckeliana (Botrytis cinerea)/Liquid Culture (Gray Mould):

[0259] 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. The Compounds 16, 21, 23, 27, 49, 194, 201, 202, 216, 225, 317, 318, 323, 359, 361, 373, 375, 419, 422, 424, and 434 (from table T1 and T1-A) 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.

[0260] 11. Glomerella lagenarium (Colletotrichum lagenarium)/Liquid Culture (Anthracnose):

[0261] 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. The Compounds 3, 5, 16, 17, 21, 23, 37, 39, 41, 43, 44, 49, 50, 107, 112, 114, 132, 136, 144, 146, 147, 150, 158, 169, 189, 191, 192, 194, 195, 196, 197, 198, 199, 201, 202, 203, 205, 208, 209, 211, 214, 215, 217, 218, 221, 223, 224, 225, 226, 227, 229, 230, 232, 233, 236, 237, 238, 240, 241, 280, 314, 317, 320, 325, 326, 327, 328, 334, 336, 339, 340, 341, 343, 344, 345, 348, 349, 351, 355, 356, 360, 361, 367, 369, 375, 378, 379, 380, 381, 382, 384, 385, 386, 387, 388, 389, 390, 392, 394, 395, 403, 404, 406, 407, 409, 411, 412, 414, 419, 424, 427, 429, 434, 439, 441, 446 and 449 (from table T1 and T1-A) 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.

[0262] 12. Mycosphaerella arachidis (Cercospora arachidicola)/Liquid Culture (Early Leaf Spot):

[0263] 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. The Compounds 3, 5, 6, 7, 13, 14, 16, 17, 18, 19, 21, 23, 37, 39, 43, 44, 50, 104, 136, 144, 147, 194, 195, 197, 198, 202, 203, 205, 214, 215, 216, 218, 225, 226, 229, 230, 232, 233, 240, 241, 261, 267, 271, 298, 302, 311, 314, 317, 318, 319, 320, 323, 324, 325, 328, 329, 330, 331, 332, 333, 334, 336, 337, 339, 340, 341, 342, 343, 344, 345, 347, 348, 350, 351, 352, 353, 355, 356, 359, 360, 361, 362, 365, 366, 371, 375, 377, 378, 379, 380, 382, 384, 385, 386, 388, 389, 391, 392, 394, 395, 396, 398, 402, 403, 404, 405, 406, 407, 412, 414, 415, 418, 419, 422, 423, 424, 430, 434, 439, 441, 446, 449 and 451 (from table T1 and T1-A) 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.

[0264] 13. Mycosphaerella graminicola (Septoria tritici)/Liquid Culture (Septoria Blotch):

[0265] 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. The Compounds 3, 5, 6, 16, 17, 18, 19, 20, 21, 23, 26, 27, 32, 37, 39, 40, 41, 50, 110, 114, 129, 136, 144, 146, 154, 161, 169, 179, 191, 192, 194, 195, 196, 197, 198, 199, 201, 202, 203, 205, 208, 211, 214, 215, 216, 218, 225, 226, 227, 229, 230, 232, 233, 236, 238, 240, 241, 314, 317, 318, 319, 320, 321, 323, 324, 325, 328, 329, 331, 332, 333, 334, 336, 339, 340, 341, 342, 343, 344, 351, 352, 355, 359, 361, 362, 367, 370, 373, 374, 375, 377, 378, 379, 381, 382, 384, 385, 387, 388, 389, 392, 394, 397, 399, 402, 403, 404, 406, 411, 413, 414, 417, 418, 419, 422, 423, 424, 429, 430, 434, 439, 441, 446, 449 and 451 (from table T1 and T1-A) 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.

[0266] 14. Gaeumannomyces graminis/Liquid Culture (Take-all of Cereals):

[0267] 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. The Compounds 3, 5, 6, 13, 16, 17, 19, 21, 23, 26, 50, 78, 85, 97, 103, 125, 129, 132, 139, 144, 157, 179, 189, 190, 191, 192, 194, 195, 196, 199, 200, 201, 202, 203, 205, 207, 208, 209, 210, 214, 215, 216, 217, 218, 221, 224, 225, 226, 229, 230, 232, 233, 236, 238, 240, 241, 291, 292, 312, 314, 316, 317, 318, 320, 321, 323, 324, 325, 326, 327, 328, 329, 330, 334, 336, 339, 340, 341, 342, 343, 344, 345, 347, 349, 351, 352, 353, 355, 356, 359, 361, 362, 365, 367, 369, 370, 373, 374, 375, 377, 378, 379, 381, 382, 385, 386, 387, 388, 389, 390, 391, 393, 394, 395, 399, 402, 403, 404, 406, 409, 410, 411, 413, 414, 415, 417, 418, 419, 422, 423, 424, 425, 429, 430, 431, 433, 434, 437, 439, 446, 447, 449, 450 and 451 (from table T1 and T1-A) 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.

[0268] 15. Monographella nivalis (Microdochium nivale)/Liquid Culture (Foot Rot Cereals):

[0269] 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. The Compounds 2, 3, 5, 6, 16, 17, 18, 19, 20, 21, 23, 26, 27, 32, 37, 39, 40, 41, 43, 44, 49, 50, 90, 95, 99, 103, 110, 114, 129, 132, 136, 144, 146, 147, 150, 161, 169, 179, 181, 186, 188, 189, 190, 191, 192, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 205, 207, 208, 209, 211, 214, 215, 216, 217, 218, 221, 222, 223, 224, 225, 226, 227, 229, 230, 232, 233, 236, 237, 238, 240, 241, 244, 279, 308, 311, 312, 314, 316, 317, 318, 319, 320, 321, 323, 324, 325, 326, 328, 329, 330, 332, 333, 334, 336, 337, 339, 340, 342, 343, 344, 349, 350, 351, 352, 355, 356, 359, 361, 362, 367, 368, 369, 370, 372, 373, 374, 375, 377, 378, 379, 380, 381, 382, 384, 385, 386, 387, 388, 389, 390, 392, 394, 395, 396, 397, 398, 399, 402, 403, 404, 405, 406, 409, 410, 411, 412, 413, 414, 415, 417, 418, 419, 422, 423, 424, 427, 429, 431, 433, 434, 439, 441, 442, 446, 447, 448, 449 and 451 (from table T1 and T1-A) 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.

[0270] 16. Fusarium culmorum/Liquid Culture (Head Blight):

[0271] 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. The Compounds 3, 16, 21, 23, 37, 39, 50, 114, 146, 150, 197, 202, 203, 205, 215, 226, 229, 230, 232, 233, 318, 323, 329, 332, 334, 336, 344, 351, 359, 361, 362, 373, 375, 379, 381, 389, 413, 419, 422, 424, 429, 430, 433, 441, 446 and 449 (from table T1 and T1-A) 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.

[0272] 17. Thanatephorus cucumeris (Rhizoctonia solani)/Liquid Culture (Foot Rot, Damping-Off):

[0273] 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 96-well microtiter plate at an application rate of 200 ppm, 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. The Compounds 3, 5, 13, 16, 17, 18, 19, 20, 21, 23, 27, 37, 39, 40, 41, 50, 148, 192, 195, 197, 198, 202, 203, 205, 206, 209, 210, 211, 214, 215, 218, 222, 225, 226, 227, 229, 230, 232, 238, 240, 241, 311, 314, 315, 316, 317, 318, 319, 320, 321, 323, 324, 327, 328, 329, 330, 331, 332, 334, 335, 336, 337, 338, 339, 340, 341, 342, 343, 344, 345, 348, 350, 351, 352, 355, 356, 359, 360, 361, 362, 364, 366, 367, 368, 369, 370, 374, 375, 377, 378, 379, 380, 381, 382, 384, 385, 386, 387, 388, 389, 390, 391, 392, 393, 394, 395, 396, 397, 398, 399, 400, 402, 403, 404, 405, 406, 407, 409, 410, 412, 413, 414, 415, 417, 418, 419, 422, 423, 424, 427, 429, 430, 431, 433, 434, 439, 441, 442 and 446 (from table T1 and T1-A) 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.

[0274] 18. Sclerotinia sclerotiorum/Liquid Culture (Cottony Rot):

[0275] 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 visually 3-4 days after application. The Compounds 16, 21, 23, 27, 37, 147, 202, 215, 230, 359, 361, 375, 379, 389, 410, 418, 419, 424, 446 and 449 (from table T1 and T1-A) 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.