MICROBIOCIDAL DERIVATIVES

Abstract

Compounds of the formula (I), wherein the substituents are as defined in claim 1, useful as pesticides, and especially fungicides.

##STR00001##

Claims

1. A compound of formula (I): ##STR00227## wherein A is N or CH; R.sup.1 is hydrogen, cyano, formyl, C.sub.1-C.sub.6alkylcarbonyl, C.sub.1-C.sub.6alkoxycarbonyl, C.sub.1-C.sub.6haloalkylcarbonyl, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.6alkylcarbonyl, C.sub.3-C.sub.6cycloalkylcarbonyl, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.3alkoxycarbonyl, C.sub.1-C.sub.6alkoxyoxalyl, C.sub.1-C.sub.6alkoxycarbonylC.sub.1-C.sub.4alkylC.sub.1-C.sub.6alkoxycarbonyl, C.sub.2-C.sub.6alkenyloxycarbonyl, or C.sub.2-C.sub.6alkynyloxycarbonyl; R.sup.2 is hydrogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, halogen, hydroxy, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.3-C.sub.6cycloalkyloxy, C.sub.3-C.sub.6halocycloalkyloxy, C.sub.2-C.sub.6alkenyloxy, C.sub.2-C.sub.6haloalkenyloxy, C.sub.2-C.sub.6alkynyloxy, C.sub.2-C.sub.6haloalkynyloxy, C.sub.1-C.sub.6cyanoalkyloxy, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.2alkyl, C.sub.2-C.sub.6alkynyl, C.sub.2-C.sub.6haloalkynyl, or C.sub.3-C.sub.6cycloalkylC.sub.1-C.sub.2alkoxy; R.sup.3 is hydrogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, halogen, hydroxy, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.3-C.sub.6cycloalkyloxy, C.sub.3-C.sub.6halocycloalkyloxy, C.sub.2-C.sub.6alkenyloxy, C.sub.2-C.sub.6haloalkenyloxy, C.sub.2-C.sub.6alkynyloxy, C.sub.2-C.sub.6haloalkynyloxy, C.sub.1-C.sub.6cyanoalkyloxy, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.2alkyl, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.2alkylcarbonyloxy, C.sub.2-C.sub.6alkynyl, C.sub.2-C.sub.6haloalkynyl, or C.sub.3-C.sub.6cycloalkylC.sub.1-C.sub.2alkoxy; R.sup.4 is C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8haloalkyl, C.sub.1-C.sub.8alkoxy, C.sub.3-C.sub.8alkynyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.8cycloalkylC.sub.1-C.sub.2alkyl, phenyl, phenylC.sub.1-C.sub.3alkyl, phenoxyC.sub.1-C.sub.3alkyl, heteroaryl, heteroarylC.sub.1-C.sub.2alkyl, heteroarylC.sub.1-C.sub.2alkoxyiminoC.sub.1-C.sub.2alkyl, wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC.sub.1-C.sub.2alkyl, wherein the heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O, and S, and wherein the cycloalkyl, phenyl, heteroaryl or heterocyclyl moieties are each optionally substituted with 1 to 3 groups represented by R.sup.6 or 1 group represented by R.sup.7; and wherein when R.sup.4 is a substituted heterocyclyl, these cycles may contain a sulfonyl (S(O).sub.2) group; or R.sup.4 is a 6- to 10-membered annulated ring system optionally comprising 1, 2, or 3 heteroatoms individually selected from N, O and S, optionally substituted with 1 or 2 groups represented by R.sup.6, and optionally bonded to the rest of the molecule through a C.sub.1-C.sub.2alkylene linker; or R.sup.4 is a 5- to 10-membered non-aromatic spirocyclic carbobi- or carbotri-cyclyl ring system optionally comprising 1, 2, 3, 4 or 5 heteroatoms individually selected from N, O and S, optionally substituted with 1 to 3 groups represented by R.sup.6, and optionally bonded to the rest of the molecule through a C.sub.1-C.sub.2alkylene linker; R.sup.5 is C.sub.1-C.sub.8alkyl, hydroxyC.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.8cycloalkylC.sub.1-C.sub.2alkyl, phenyl, heteroaryl, wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, heterocyclyl, wherein the heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring or a 9- to 10-membered non-aromatic bicyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are each optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R.sup.9; R.sup.6 is halogen, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4haloalkyl, cyano, or C.sub.1-C.sub.4haloalkoxy; R.sup.7 is C.sub.1-C.sub.4alkylsulfonyl, C.sub.3-C.sub.8cycloalkyl, phenyl, benzyl, phenoxy, or pyridyl, wherein each cycloalkyl, phenyl or pyridyl group is optionally substituted by 1 group represented by R.sup.1; R.sup.8 is halogen or C.sub.1-C.sub.4haloalkyl; R.sup.9 is halogen, cyano, benzyl, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, or C.sub.1-C.sub.4haloalkyl; or a salt or an N-oxide thereof.

2. The compound according to claim 1, wherein R.sup.1 is hydrogen, cyano, C.sub.1-C.sub.6alkylcarbonyl, C.sub.1-C.sub.4alkoxycarbonyl, C.sub.1-C.sub.4haloalkylcarbonyl, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.3alkylcarbonyl, C.sub.3-C.sub.6cycloalkylcarbonyl, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.2alkoxycarbonyl, C.sub.2-C.sub.4alkenyloxycarbonyl, or C.sub.2-C.sub.4alkynyloxycarbonyl.

3. The compound according to claim 1, wherein R.sup.2 is hydrogen.

4. The compound according to claim 1, wherein R.sup.3 is hydrogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.4haloalkyl, halogen, hydroxy, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.3-C.sub.6cycloalkyloxy, C.sub.2-C.sub.6alkenyloxy, C.sub.2-C.sub.5haloalkenyloxy, C.sub.2-C.sub.6alkynyloxy, C.sub.2-C.sub.5haloalkynyloxy, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.2alkyl, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.2alkylcarbonyloxy, or C.sub.2-C.sub.5alkynyl.

5. The compound according to claim 1, wherein R.sup.4 is C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8alkynyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.8cycloalkylC.sub.1-C.sub.2alkyl, phenylC.sub.1-C.sub.3alkyl, phenoxyC.sub.1-C.sub.3alkyl, heteroaryl, heteroarylC.sub.1-C.sub.2alkyl, heteroarylC.sub.1-C.sub.2alkoxyiminoC.sub.1-C.sub.2alkyl, wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, or 3 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC.sub.1-C.sub.2alkyl, wherein the heterocyclyl is a 5- or 6-membered non-aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O, and S, and wherein the cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are each optionally substituted with 1 to 3 groups represented by R.sup.6 or 1 group represented by R.sup.7; and wherein when R.sup.4 is a substituted heterocyclyl, these cycles may contain a sulfonyl (S(O).sub.2) group; or R.sup.4 is a 7- to 10-membered annulated ring system optionally comprising 1, 2, or 3 heteroatoms individually selected from N, O and S, optionally substituted with 1 or 2 groups represented by R.sup.6, and optionally bonded to the rest of the molecule through a C.sub.1-C.sub.2alkylene linker; or R.sup.4 is a 6- to 10-membered non-aromatic spirocyclic carbobi- or carbotri-cyclyl ring system optionally comprising 1, 2, 3, 4 or 5 heteroatoms individually selected from N, O and S, optionally substituted with 1 to 3 groups represented by R.sup.6, and optionally bonded to the rest of the molecule through a C.sub.1-C.sub.2alkylene linker.

6. The compound according to claim 1, wherein R.sup.4 is t-butyl, isopentyl, 2,2-dimethylpropyl, 1,5-dimethylhexyl, 4,4-dimethylpent-2-ynyl, cyclopropyl optionally substituted with 1 group represented by R.sup.6 or 1 group represented by R.sup.7, cyclobutyl optionally substituted with 1 or 2 groups represented by R.sup.6 or 1 group represented by R.sup.7, cyclopropylmethyl optionally substituted with 1 group represented by R.sup.6 or 1 group represented by R.sup.7, phenylC.sub.1-C.sub.3alkyl optionally substituted with 1 or 2 groups represented by R.sup.6 or 1 group represented by R.sup.7, phenoxyC.sub.1-C.sub.3alkyl optionally substituted with 1 or 2 groups represented by R.sup.6, heteroarylC.sub.1-C.sub.2alkyl, heteroarylC.sub.1-C.sub.2alkoxyiminoC.sub.1-C.sub.2alkyl, wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1 or 2 heteroatoms individually selected from N and O, and wherein the heteroaryl moieties are optionally substituted with 1 or 2 groups represented by R.sup.6 or 1 group represented by R.sup.7, heterocyclyl wherein the heterocyclyl is a 5- or 6-membered non-aromatic monocyclic ring comprising a single heteroatom selected from N and O, heterocyclylC.sub.1-C.sub.2alkyl, wherein the heterocyclyl is a 5- or 6-membered non-aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N and O, and wherein the heterocyclyl moieties optionally substituted with 1 group represented by R.sup.6 or 1 group represented by R.sup.7; and wherein when R.sup.4 is a substituted heterocyclyl, these cycles may contain a sulfonyl (S(O).sub.2) group; or R.sup.4 is a 7- to 9-membered annulated ring system optionally comprising 1, 2, or 3 heteroatoms individually selected from N and O, optionally substituted with 1 or 2 groups represented by R.sup.6, and optionally bonded to the rest of the molecule through a C.sub.1-C.sub.2alkylene linker; or R.sup.4 is a 6- to 9-membered non-aromatic spirocyclic carbobicyclyl ring system optionally comprising 1, 2, or 3 heteroatoms individually selected from N and O, optionally substituted with 1 or 2 groups represented by R.sup.6, and optionally bonded to the rest of the molecule through a C.sub.1-C.sub.2alkylene linker.

7. The compound according to claim 1, wherein R.sup.4 is t-butyl, isopentyl, 2,2-dimethylpropyl, 1,1,2-trimethylpropyl, 1-methylcyclopropyl, 1-methylcyclobutyl, 1-ethylcyclobutyl, 1-isopropylcycobutyl, 1-tertbutylcyclobutyl, 1-cyclobutylcyclobutyl, 2,2-dimethylcyclobutyl, 1-methylcyclopentyl, or spiro[3.4]octan-3-yl.

8. The compound according to claim 1, wherein R.sup.6 is chloro, fluoro, methyl, cyano, difluoromethyl, or trifluoromethyl.

9. The compound according to claim 1, wherein R.sup.5 is C.sub.1-C.sub.6alkyl, hydroxyC.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkylC.sub.1-C.sub.2alkyl, phenyl, heteroaryl, wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, heterocyclyl, wherein the heterocyclyl is a 5- or 6-membered non-aromatic monocyclic ring or a 9- to 10-membered non-aromatic bicyclic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are each optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R.sup.9.

10. The compound according to claim 1, wherein R.sup.5 is C.sub.1-C.sub.6alkyl, 2,3-dihydroxypropyl, C.sub.3-C.sub.4cycloalkyl, cyclopropylmethyl, cyclobutylmethyl, phenyl, heteroaryl, wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1 or 2 heteroatoms individually selected from N and S, heterocyclyl, wherein the heterocyclyl is a 9- to 10-membered non-aromatic bicyclic ring comprising 1 or 2 oxygen atoms, and wherein the phenyl and heteroaryl moieties are each optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R.sup.9.

11. The compound according to claim 1, wherein, R.sup.5 is 2,3-dihydroxypropyl, cyclobutyl, cyclopropylmethyl, phenyl, 3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 3-methylphenyl, 4-methylphenyl, 3-ethylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dimethylphenyl, 3,5-dimethoxyphenyl, 3-fluoro-4-methylphenyl, 3-chloro-4-methylphenyl, 3-chloro-5-fluorophenyl, 4-chloro-3,5-difluorophenyl, 4-chloro-3-fluorophenyl, 4-chloro-3-methylphenyl, 3-cyano-5-methylphenyl, 3-cyano-5-fluorophenyl, 4-cyano-3-fluorophenyl, 3,4,5-trifluorophenyl, 4-trifluoromethylphenyl, 3-fluoro-4-(trifluoromethyl)phenyl, pyridin-4-yl, 2-fluoropyridin-4-yl, 2-chloropyridin-4-yl, 2,6-difluoropyridin-4-yl, 2,6-dichloropyridin-4-yl, pyridin-3-yl, 6-fluoropyridin-3-yl, 5-fluoropyridin-3-yl, 6-chloropyridin-3-yl, 5-chloropyridin-3-yl, 5-(trifluoromethyl)-pyridin-3-yl, 2,6-difluoro-3-iodopyridin-4-yl, isothiazol-4-yl, thiazol-2-yl, pyrimidin-5-yl, benzofuran-5-yl, 1-benzylindazol-6-yl, or 1,3-benzodioxol-5-yl.

12. An agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to claim 1.

13. The composition according to claim 12, further comprising at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.

14. A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) according to claim 1, is applied to the plants, to parts thereof or the locus thereof.

15. Use of a compound of formula (I) according to claim 1 as a fungicide.

16. The compound according to claim 2, wherein R.sup.2 is hydrogen.

17. A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) according to a composition according to claim 12, is applied to the plants, to parts thereof or the locus thereof.

Description

FORMULATION EXAMPLES

[0226]

TABLE-US-00003 Wettable powders a) b) c) active ingredient [compound of formula (I)] 25% 50% 75% sodium lignosulfonate  5%  5% — sodium lauryl sulfate  3% —  5% sodium diisobutylnaphthalenesulfonate —  6% 10% phenol polyethylene glycol ether —  2% — (7-8 mol of ethylene oxide) highly dispersed silicic acid  5% 10% 10% Kaolin 62% 27% —

[0227] The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.

TABLE-US-00004 Powders for dry seed treatment a) b) c) active ingredient [compound of formula (I)] 25% 50% 75% light mineral oil  5%  5%  5% highly dispersed silicic acid  5%  5% — Kaolin 65% 40% — Talcum — 20%

[0228] The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

TABLE-US-00005 Emulsifiable concentrate active ingredient [compound of formula (I)] 10% octylphenol polyethylene glycol ether  3% (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate  3% castor oil polyglycol ether (35 mol of ethylene oxide)  4% Cyclohexanone 30% xylene mixture 50%

[0229] Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

TABLE-US-00006 Dusts a) b) c) Active ingredient [compound of formula (I)]  5%  6%  4% talcum 95% — — Kaolin — 94% — mineral filler — — 96%

[0230] Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.

TABLE-US-00007 Extruder dranules Active ingredient [compound of formula (I)] 15% sodium lignosulfonate  2% carboxymethylcellulose  1% Kaolin 82%

[0231] The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

TABLE-US-00008 Coated granules Active ingredient [compound of formula (I)]  8% polyethylene glycol (mol. wt. 200)  3% Kaolin 89%

[0232] The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

TABLE-US-00009 Suspension concentrate active ingredient [compound of formula (I)] 40% propylene glycol 10% nonylphenol polyethylene glycol ether (15 mol of ethylene oxide)  6% Sodium lignosulfonate 10% carboxymethylcellulose  1% silicone oil (in the form of a 75% emulsion in water)  1% Water 32%

[0233] 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.

TABLE-US-00010 Flowable concentrate for seed treatment active ingredient [compound of formula (I)]   40% propylene glycol   5% copolymer butanol PO/EO   2% tristyrenephenole with 10-20 moles EO   2% 1,2-benzisothiazolin-3-one (in the form of a 20% solution in  0.5% water) monoazo-pigment calcium salt   5% Silicone oil (in the form of a 75% emulsion in water)  0.2% Water 45.3%

[0234] 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.

Slow Release Capsule Suspension

[0235] 28 parts of a combination of the compound of formula (I) are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed.

[0236] The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns.

[0237] The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

EXAMPLES

[0238] The Examples which follow serve to illustrate the invention. The compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.

[0239] Compounds of formula (I) may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile (including improved crop tolerance), improved physico-chemical properties, or increased biodegradability).

List of Abbreviations

[0240] ° C.=degrees Celsius, CDCl.sub.3=chloroform-d, d=doublet, DIPEA=N,N-diisopropylethylamine, DMF=dimethylformamide, HAUT=1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate, m=multiplet, MHz=mega hertz, N=normal, s=singlet

General

[0241] Throughout this description, temperatures are given in degrees Celsius (° C.) and “m.p.” means melting point. LC/MS means Liquid Chromatography Mass Spectrometry and the description of the apparatus and the method is:

[0242] Method A: ACQUITY UPLC from Waters, Waters UPLC HSS T3, 1.8 mm particle size, 30×2.1 mm column, 0.85 mL/min., 60° C., H2O/MeOH 95:5+0.05% HCOOH (90%)/CH3CN+0.05% HCOOH (10%)—1.2 min.—CH3CN+0.05% HCOOH (100%)—0.30 min., ACQUITY SQD Mass Spectrometer from Waters, ionization method: electrospray (ESI), Polarity: positive ions, Capillary (kV) 3.00, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (° C.) 150, Desolvation Temperature (° C.) 350, Cone Gas Flow (L/Hr) 0, Desolvation Gas Flow (L/Hr) 650).

[0243] Method B: ACQUITY UPLC from Waters, Waters UPLC HSS T3, 1.8 mm particle size, 30×2.1 mm column, 0.85 mL/min., 60° C., H2O/MeOH 95:5+0.05% HCOOH (90%)/CH3CN+0.05% HCOOH (10%)—2.7 min.—CH3CN+0.05% HCOOH (100%)—0.30 min., ACQUITY SQD Mass Spectrometer from Waters, ionization method: electrospray (ESI), Polarity: positive ions, Capillary (kV) 3.00, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (° C.) 150, Desolvation Temperature (° C.) 350, Cone Gas Flow (L/Hr) 0, Desolvation Gas Flow (L/Hr) 650).

[0244] Method C: ACQUITY Mass Spectrometer from Waters Corporations (SQD or SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.0 kV, Cone: 30V, Extractor: 3.00 V, Source Temperature: 150° C., Desolvation Temperature: 400° C., Cone Gas Flow: 60 L/hr, Desolvation Gas Flow: 700 L/hr, Mass range: 140 to 800 Da) and an ACQUITY UPLC from Waters Corporations with solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30×2.1 mm, Temp: 60° C., DAD Wavelength range (nm): 210 to 400, Solvent Gradient: A=Water/Methanol 9:1+0.1% formic acid, B=Acetonitrile+0.1% formic acid, gradient: 0-100% B in 2.5 min; Flow (ml/min) 0.75.).

Example 1: Preparation of 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-4-methoxy-pyridine-2-carboxamide (Table 3, Compound P-101)

[0245] ##STR00019##

Step A: Preparation of 6-chloro-N-(2,2-dimethylcyclobutyl)-4-methoxy-pyridine-2-carboxamide

[0246] ##STR00020##

[0247] 2,2-dimethylpropan-1-amine (1.1 equiv.), 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU, 1.1. equiv.) and N,N-diisopropylethylamine (2.6 equiv.) were added in sequence to a DMF solution (15.7 mL) of 6-chloro-4-methoxy-pyridine-2-carboxylic acid (300 mg, 1.57 mmol, 1 equiv.). The resulting solution was stirred at room temperature for 1 h until consumption of starting material (LCMS control). Then a saturated NaHCO.sub.3 solution was added to the mixture and the solution extracted three times with ethylacetate, the organic phases combined, dried over sodium sulphate and all the volatiles removed by rotatory evaporator. Purification by column chromatography on silica gel (eluent: mixtures of cyclohexane/ethylacetate) gave the desired product 6-chloro-N-(2,2-dimethylcyclobutyl)-4-methoxy-pyridine-2-carboxamide.

[0248] .sup.1H-NMR (400 MHz, CDCl.sub.3): □=1.13 (s, 3H), 1.22 (s, 3H), 1.60-1.65 (m, 2H), 1.90-2.00 (m, 1H), 2.28-2.35 (m, 1H), 3.93 (s, 3H), 4.27-4.35 (q, 1H), 6.93-6.97 (d, 1H), 7.66-7.70 (d, 1H), 7.90-7.94 (m, 1H).

Step B: Preparation of 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-4-methoxy-pyridine-2-carboxamide (Table 3, Compound P-101)

[0249] ##STR00021##

[0250] Under an argon atmosphere, BrettPhos-G3-palladacycle ([(2-Di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II)methanesulfonate (0.1 equiv.), and potassium tertbutoxide (2.5 equiv.) were added to a degassed, stirred mixture of 6-chloro-N-(2,2-dimethylcyclobutyl)-4-methoxy-pyridine-2-carboxamide (100 mg, 0.37 mmol, 1 equiv.) and 3,5-difluoro aniline (1.1 equiv.) in THE (1.5 mL). The reaction was heated to reflux and stirred for 1 hour, then the mixture was cooled to room temperature and ethylacetate was added to the mixture. The organic layer was washed with a saturated ammonium chloride aqueous solution, dried over anhydrous sodium sulphate and concentrated in vacuo. Purification by column chromatography on silica gel (eluent: mixtures cyclohexane ethylacetate) afforded the desired methyl 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-4-methoxy-pyridine-2-carboxamide.

[0251] .sup.1H-NMR (400 MHz, (CD.sub.3).sub.2SO): δ=1.08-1.13 (m, 6H), 1.45-1.60 (m, 2H), 1.86-2.00 (m, 1H), 2.10-2.20 (m, 1H), 3.07 (s, 3H), 4.10-4.20 (q, 1H), 6.46-6.49 (d, 1H), 6.65-6.75 (m, 1H), 7.03-7.07 (d, 1H), 7.30-7.40 (m, 2H), 7.97-8.05 (d, 1H), 9.65 (s, 1H).

Example 2: Preparation of 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (Table 3, Compound P-22)

[0252] ##STR00022##

Step A: Preparation of methyl 6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxylate

[0253] ##STR00023##

[0254] Under an argon atmosphere, BrettPhos-G3-palladacycle ([(2-Di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate, 0.1 equiv.) and cesium carbonate (2.5 equiv.) were added to a degassed, stirred mixture of methyl 6-bromo-3-methoxy-pyridine-2-carboxylate (700 mg, 2.84 mmol, 1 equiv.) and 3,5-difluoro aniline (1.1 equiv.) in THE (11.4 mL). The reaction was heated to 80° C. and stirred for 1 hour, then the mixture was cooled to room temperature. The volatiles were removed using a rotatory evaporator and the residue was dissolved in ethylacetate. The organic phase was washed twice with water, dried over anhydrous sodium sulphate and concentrated in vacuo. Purification by column chromatography on silica gel (eluent: mixtures cyclohexane ethylacetate) afforded the desired methyl 6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxylate.

[0255] .sup.1H-NMR (400 MHz, (CD.sub.3).sub.2SO): δ=3.80 (s, 3H), 3.85 (s, 3H), 6.55-6.63 (m, 1H), 7.07-7.12 (d, 1H), 7.42-7.50 (m, 2H), 7.65-7.72 (d, 1H).

Step B: Preparation of 6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxylic acid

[0256] ##STR00024##

[0257] Lithium hydroxide monohydrate (4 equiv.) was added to a solution of methyl 6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxylate (930 mg, 3.16 mmol) in a mixture of tetrahydrofuran (14 mL) and water (5 mL). The reaction mixture was stirred 4 h at room temperature, then the solvents were removed in vacuo. The residue was diluted with ethyl acetate and water, then 2 N hydrochloric acid was slowly added until a pH of 3-4 was reached. The phases were separated and the aqueous layer was extracted three times with ethylacetate. Then the combined organic phases were dried over sodium sulphate and all the volatiles evaporated using a rotatory evaporator. The obtained 6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxylic acid was directly used in the next step without further purification.

Step C: Preparation of 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (Table 3, Compound P-22)

[0258] ##STR00025##

[0259] 2,2-dimethylpropan-1-amine (1.1 equiv.), 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU, 1.1. equiv.) and N,N-diisopropylethylamine (2.6 equiv.) were added in sequence to a DMF solution (3.6 mL) of 6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxylic acid (100 mg, 0.36 mmol, 1 equiv.). The resulting solution was stirred at room temperature for 1 h until consumption of starting material (LCMS control). Then a saturated NaHCO.sub.3 solution was added to the mixture and the solution extracted three times with ethylacetate, the organic phases combined, dried over sodium sulphate and all the volatiles removed by rotatory evaporator. Purification by column chromatography on silica gel (eluent: mixtures of cyclohexane/ethylacetate) gave the desired product 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamide.

[0260] .sup.1H-NMR (400 MHz, CDCl.sub.3): δ=1.00 (s, 9H), 3.28 (d, 2H), 3.97 (s, 3H), 6.40-6.50 (m, 1H), 6.75-6.90 (m, 3H), 7.05-7.10 (d, 1H), 7.40-7.45 (d, 1H), 7.80-7.85 (m, 1H).

Example 3: Preparation of 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-prop-2-ynoxy-pyridine-2-carboxamide (Table 3, Compound P-86)

[0261] ##STR00026##

Step A: Preparation of 6-(3,5-difluoroanilino)-3-hydroxy-pyridine-2-carboxylic acid

[0262] ##STR00027##

[0263] In a vial, under an argon atmosphere, 6-bromo-3-hydroxy-pyridine-2-carboxylic acid (CAS: 321596-58-1, 0.8 g, 3.66 mmol) was dissolved in tert-butanol (18 mL). To this solution, cesium carbonate (2.39 g, 7.33 mmol) was added followed by 3,5-difluoroaniline (CAS: 372-39-4, 0.71 g, 5.50 mmol). The suspension obtained was flushed with argon, ROCKPHOS Pd G3 (0.31 g, 0.36 mmol) was added and the resulting brown suspension was heated to 75° C. and stirred at this temperature overnight. The reaction mixture was cooled down at room temperature and poured on water and ethyl acetate. The aqueous layer was washed with ethylacetate. Then the pH of aqueous layer was adjusted to pH 7 and the phase was extracted two times with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated to afford 6-(3,5-difluoroanilino)-3-hydroxy-pyridine-2-carboxylic acid.

[0264] 1H NMR (400 MHz, DMSO) δ ppm 6.44-6.56 (m, 1H) 6.90 (d, J=8.80 Hz, 1H) 7.14 (d, J=8.80 Hz, 1H) 7.48 (dd, J=11.00, 2.20 Hz, 2H) 9.18 (s, 1H) 14.21-16.05 (m, 1H)

[0265] LC-MS (method A): 267 [M+H], Rt: 0.77 min

Step B: Preparation of 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-hydroxy-pyridine-2-carboxamide

[0266] ##STR00028##

[0267] To a solution of 6-(3,5-difluoroanilino)-3-hydroxy-pyridine-2-carboxylic acid (0.557 g, 2.09 mmol) in N,N-dimethylformamide (21 mL) was added 2,2-dimethylcyclobutanamine; hydrochloride (0.312 g, 2.30 mmol). Then N,N-diisopropylethylamine (0.547 mL, 3.14 mmol) and HATU (1.19 g, 3.14 mmol) were added slowly. The reaction mixture was stirred at room temperature for 3 hours and then HATU (0.398 g, 1.05 mmol) was added again and the resulting mixture was stirred at room temperature for 1 more hour. The reaction mixture was quenched with sodium bicarbonate sat. aq. and diluted with water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude was purified by chromatography over silica gel to afford 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-hydroxy-pyridine-2-carboxamide.

[0268] 1H NMR (400 MHz, Chloroform) 6 ppm 1.17-1.23 (m, 6H) 1.58-1.69 (m, 2H) 1.94 (dd, J=11.19, 9.72 Hz, 1H) 2.28-2.40 (m, 1H) 4.29 (q, J=8.93 Hz, 1H) 6.41-6.52 (m, 2H) 6.88-6.92 (m, 1H) 6.93-7.00 (m, 2H) 7.29-7.33 (m, 1H) 7.80-7.91 (m, 1H) 11.87 (s, 1H)

[0269] LC-MS (method A): 348 [M+H], Rt: 1.27 min

Step C: Preparation of 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-prop-2-ynoxy-pyridine-2-carboxamide (Table 3, Compound P-86)

[0270] ##STR00029##

[0271] To a solution of 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-hydroxy-pyridine-2-carboxamide (0.080 g, 0.23 mmol) in N,N-dimethylformamide (1.2 mL, 15 mmol) were added 3-bromoprop-1-yne (80% in xylene) (0.028 mL, 0.25 mmol) and potassium carbonate (0.035 g, 0.25 mmol). The resulting mixture was stirred at room temperature for 1 hour. LCMS analysis showed full conversion. The reaction mixture was quenched with water and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude was purified by chromatography over silica gel to afford 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-prop-2-ynoxy-pyridine-2-carboxamide.

[0272] 1H NMR (400 MHz, Chloroform) δ ppm 1.14 (s, 3H) 1.21 (s, 3H) 1.55-1.70 (m, 2H) 1.88 (dd, J=11.37, 9.54 Hz, 1H) 2.27-2.39 (m, 1H) 2.55 (t, J=2.38 Hz, 1H) 4.34 (q, J=8.93 Hz, 1H) 4.84-4.88 (m, 2H) 6.48 (tt, J=8.99, 2.20 Hz, 1H) 6.61 (s, 1H) 6.94-7.04 (m, 3H) 7.57 (d, J=8.80 Hz, 1H) 7.72 (br d, J=8.44 Hz, 1H)

[0273] LC-MS (method A): 386 [M+H], Rt: 1.13 min

Example 4: Preparation of 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylpropyl)-3-hydroxy-pyridine-2-carboxamide (Table 3, Compound P-100)

[0274] ##STR00030##

[0275] A mixture of 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (0.580 g, 1.66 mmol) and pyridine hydrochloride (0.976 g, 8.28 mmol) was heated to 150° C. to give a light brown solution. This solution was stirred for 16 hours at 150° C. After cooling down at room temperature, the reaction mixture was diluted with dichloromethane and loaded on Isolute. This crude was purified by chromatography over silica gel to afford 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylpropyl)-3-hydroxy-pyridine-2-carboxamide.

[0276] 1H NMR (400 MHz, DMSO d6) δ ppm 0.94-0.98 (s, 9H) 3.16-3.22 (d, 2H) 7.09-7.13 (s, 2H) 7.14-7.19 (d, 1H) 7.42-7.54 (d, 1H) 8.24-8.42 (m, 1H) 10.11-10.26 (s, 1H) 12.04-12.19 (s, 1H)

[0277] LC-MS (method A): 337[M+H], Rt: 1.15 min

Example 5: Preparation of 6-(N-cyano-3,5-difluoro-anilino)-N-(2,2-dimethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide (Table 3, Compound P-20)

[0278] ##STR00031##

[0279] 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide prepared as described above for compound P-86 (0.0600 g, 0.166 mmol) was dissolved in tetrahydrofuran (0.830 mL) under an argon atmosphere and the solution obtained was cooled down to −78° C. Then N-butyllithium 1.6 M in hexane (0.13 mL, 0.214 mmol) was added carefully and drop wise by syringe. The resulting mixture was stirred for 30 min at −78° C. and cyanogen bromide (0.0370 g, 0.332 mmol) was added carefully. The mixture was stirred for 30 min at −78° C. then warmed up to room temperature and stirred for 2 hours. The reaction mixture was quenched with NaHCO.sub.3 sat. solution (20 mL) at −10° C. The aqueous phase was extracted three times with ethyl acetate (15 mL). The organic phases were combined, washed with water (2×10 mL) and brine (1×10 mL), dried over sodium sulfate and evaporated. The crude was purified by chromatography over silica gel to afford 6-(N-cyano-3,5-difluoro-anilino)-N-(2,2-dimethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide.

[0280] 1H NMR (400 MHz, Chloroform) δ ppm 1.03 (s, 3H) 1.18 (s, 3H) 1.52-1.68 (m, 2H) 1.79 (dd, J=11.00, 9.54 Hz, 1H) 2.22-2.33 (m, 1H) 4.00 (s, 3H) 4.27 (q, J=8.68 Hz, 1H) 6.85 (s, 1H) 7.01 (dd, J=7.70, 2.20 Hz, 2H) 7.37 (d, J=8.80 Hz, 1H) 7.55 (d, J=8.80 Hz, 2H)

[0281] LC-MS (method A): 387[M+H], Rt: 1.07 min

Example 6: Preparation of [6-(3,5-difluoro-N-(2-methoxyacetyl)anilino)-2-[(2,2-dimethylcyclobutyl) carbamoyl]-3-pyridyl] 2-methoxyacetate. (Table 3, Compound P-24)

[0282] ##STR00032##

[0283] 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide (0.0370 g, 0.102 mmol) was suspended in methoxyacetyl chloride (0.410 mL, 4.48 mmol) under an argon atmosphere. The reaction mixture was heated stirred for 20 hours at 90° C. and then 6 hours at 100° C. The reaction mixture was quenched carefully by drop wise addition of NaHCO.sub.3 (20 mL). The aqueous phase was extracted with ethyl acetate (3×15 mL). The organic phases were combined, washed with water (2×10 mL), and brine (1×10 mL), dried and evaporated under reduced pressure. The crude was purified by chromatography over silica gel to afford [6-(3,5-difluoro-N-(2-methoxyacetyl)anilino)-2-[(2,2-dimethylcyclobutyl)carbamoyl]-3-pyridyl] 2-methoxyacetate.

[0284] 1H NMR (400 MHz, Chloroform) δ ppm 0.88 (s, 3H) 1.09 (s, 3H) 1.48-1.68 (m, 3H) 2.15-2.26 (m, 1H) 3.43 (s, 3H) 3.57 (s, 3H) 4.03 (s, 2H) 4.13 (m, 1H) 4.44 (d, J=0.73 Hz, 2H) 6.93 (dd, J=6.79, 2.38 Hz, 2H) 6.95-7.03 (m, 1H) 7.30-7.36 (m, 1H) 7.59 (d, J=8.80 Hz, 1H) 8.08-8.14 (m, 1H)

[0285] LC-MS (method A): 492 [M+H], Rt: 1.07 min

Example 7: N-tert-butyl-6-(3,5-difluoroanilino)-3-methoxy-1-oxido-pyridin-1-ium-2-carboxamide (Table 3. Compound P-117)

[0286] ##STR00033##

[0287] A solution of N-tert-butyl-6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (0.100 g, 0.298 mmol, compound P-93, Table 3) in dichloromethane (3 mL) was cooled to 0° C. under argon and treated with urea hydrogen peroxide (0.0309 g, 0.328 mmol) to give a pale brown cloudy solution. To this was added dropwise, trifluoroacetic anhydride (0.127 g, 0.0838 mL, 0.596 mmol) and the resulting light brown solution allowed to warm to room temperature, and stirred for 17 hours where LCMS showed reaction completion. The reaction mixture was quenched with aqueous Na.sub.2SO.sub.3 and poured into a 0.5M HCl aqueous solution. Extraction with dichloromethane, followed by washing of the organic layer with aqueous NaHCO.sub.3, and then drying over anhydrous Na.sub.2SO.sub.4, and concentration in vacuo gave the crude product. This was purified Flash chromatography eluting with methanol/dichloromethane to give the title compound as a yellow powder.

[0288] .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm 1.50-1.54 (s, 9H) 3.88-3.91 (s, 3H) 6.55-6.61 (m, 1H) 6.66-6.70 (m, 1H) 6.70-6.77 (m, 2H) 7.02-7.06 (d, 1H) 7.19-7.23 (d, 1H) 8.50-8.58 (s, 1H).

[0289] LCMS (Method A); 352 [M+H], Rt: 0.85 min

[0290] Table 3 below illustrates exemplified individual compounds of formula (I) according to the invention.

TABLE-US-00011 Table 3 Melting point and LC/MS data (R.sub.t = Retention time) for selected compounds of Table 1 and Table 2. Compound Mp No. Name Structure (° C.) LC/MS P-1 6-[(2,6-difluoro-4- pyridyl)amino]-N-(2,2- dimethylcyclobutyl)-3- hydroxy-pyridine-2- carboxamide [00034] 147- 151.8 R.sub.t = 1.17 min (A); MS: m/z = 349.3 (M + 1) P-2 6-(3,5-difluoroanilino)- N-(2,2- dimethylcyclobutyl)-3- hydroxy-pyridine-2- carboxamide [00035] 160.1- 161.2 R.sub.t = 1.27 min (A); MS: M/z = 348.5 (M + 1) P-3 6-[(2,6-difluoro-4- pyridyl)amino]-3- hydroxy-N- spiro[3.4]octan-3-yl- pyridine-2- carboxamide [00036] 165.8- 168.6 R.sub.t = 1.24 min (A); MS: m/z = 375.4 (M + 1) P-4 6-[(2,6-difluoro-4- pyridyl)amino]-N-(2,2- dimethylcyclobutyl)-3- methoxy-pyridine-2- carboxamide [00037] 154- 156 R.sub.t = 0.99 min (A); MS: m/z = 363.5 (M + 1) P-5 N-(2,2- dimethylcyclobutyl)-3- methoxy-6-(thiazol-2- ylamino)pyridine-2- carboxamide [00038] R.sub.t = 1.04 min (A); MS: m/z = 333.4 (M + 1) P-6 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N- spiro[3.4]octan-3-yl- pyridine-2- carboxamide [00039] 76.2- 90.1 R.sub.t= 1.06 min (A); MS: m/z = 389.5 (M + 1) P-7 6-(3,5-difluoroanilino)- N-(2,2- dimethylcyclobutyl)-3- methoxy-pyridine-2- carboxamide [00040] R.sub.t = 1.09 min (A); MS: m/z = 362.4 (M + 1) P-8 2-(3,5-difluoroanilino)- N-isopentyl-5- methoxy-pyrimidine-4- carboxamide [00041] 130-132 P-9 2-[(2,6-difluoro-4- pyridyl)amino]-N- isopentyl-5-methoxy- pyrimidine-4- carboxamide [00042] 71-73 P-10 2-(3,5-difluoroanilino)- N-(2,2- dimethylcyclobutyl)-5- methoxy-pyrimidine-4- carboxamide [00043] 192-194 P-11 2-[(2,6-difluoro-4- pyridyl)amino]-N-(2,2- dimethylcyclobutyl)-5- methoxy-pyrimidine-4- carboxamide [00044] .sup.1H NMR data: See footnote P-12 N-(2 2- dimethylcyclobutyl)-6- [(5-fluoro-3- pyridyl)amino]-3- hydroxy-pyridine-2- carboxamide [00045] R.sub.t = 1.71 mi n (C); MS: m/z = 331.15 (M + 1) P-13 N-(2,2- dimethylcyclobutyl)-6- [(6-fluoro-3- pyridyl)amino]-3- hydroxy-pyridine-2- carboxamide [00046] R.sub.t =1.73 min (C); MS: m/z = 331.15 (M + 1) P-14 6-[(2-chloro-4- pyridyl)amino]-N-(2,2- dimethylcyclobutyl)-3- hydroxy-pyridine-2- carboxamide [00047] R.sub.t = 1.74 mi (C); MS: m/z = 347.13 (M + 1) P-15 N-(2,2- dimethylcyclobutyl)-3- hydroxy-6-(pyrimidin- 5-ylamino)pyridine-2- carboxamide [00048] R.sub.t = 1.44 min (C); MS: m/z = 314.15 (M + 1) P-16 6-anilino-N-(2,2- dimethylcyclobutyl)-3- hydroxy-pyridine-2- carboxamide [00049] R.sub.t = 1.95 mi (C); MS: m/z = 312.18 (M + 1) P-17 6-(1,3-benzodioxo1-5- ylamino)-N-(2,2- dimethylcyclobutyl)-3- hydroxy-pyridine-2- carboxamide [00050] R.sub.t = 1.86 min (C); MS: m/z = 356.17 (M + 1) P-18 N-(2,2- dimethylcyclobutyl)-6- [(2-fluoro-4- pyridyl)amino]-3- hydroxy-pyridine-2- carboxamide [00051] R.sub.t = 1.68 (C); MS: m/z = 331.17 (M + 1) P-19 N-(2,2- dimethylcyclobutyl)-3- hydroxy-6-(isothiazol- 4-ylamino)pyridine-2- carboxamide [00052] R.sub.t = 1.70 min (C); MS: m/z = 319.12 (M + 1) P-20 6-(N-cyano-3,5- difluoro-anilino)-N- (2,2- dimethylcyclobutyl)-3- methoxy-pyridine-2- carboxamide [00053] 122-124 R.sub.t = 1.07 min (A); MS: m/z = 387 (M + 1) P-21 6-[cyano-(2,6-difluoro- 4-pyridyl)amino]-N- (2,2- dimethylcyclobutyl)-3- methoxy-pyridine-2- carboxamide [00054] 141-142 R.sub.t = 1.02 min (A); MS: m/z = 388 (M + 1) P-22 6-(3,5-difluoroanilino)- N-(2,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00055] 47-55 R.sub.t = 1.05 min (A); MS: m/z = 350 (M + 1) P-23 6-(3,5-difluoroanilino)- 3-methoxy-N-(2- phenylpropyl)pyridine- 2-carboxamide [00056] 60-69 R.sub.t = 1.09 min (A); MS: m/z = 398 (M + 1) P-24 [6-(3,5-difluoro-N-(2- methoxyacetyl)anilino)- 2-[(2,2- dimethylcyclobutyl) carbamoyl]-3-pyridyl]2- methoxyacetate [00057] 100-102 R.sub.t = 1.07 min (A); MS: m/z = 492 (M + 1) P-25 N-benzyl-6-(3,5- difluoroanilino)-3- methoxy-pyridine-2- carboxamide [00058] R.sub.t = 1.02 min (A); MS: m/z = 370 (M + 1) P-26 6-(3,5-difluoroanilino)- N-[(3,5- difluorophenyl)methyl]- 3-methoxy-pyridine- 2-carboxamide [00059] 82-90 R.sub.t = 1.04 min (A); MS: m/z = 406 (M + 1) P-27 6-(3,5-difluoroanilino)- N-[2-(4- fluorophenoxy)ethyl]- 3-methoxy-pyridine-2- carboxamide [00060] R.sub.t = 1.05 min (A); MS: m/z = 418 (M + 1) P-28 6-(3,5-difluoroanilino)- N-(4,4-dimethylpent-2- ynyl)-3-methoxy- pyridine-2- carboxamide [00061] 54-63 R.sub.t = 1.10 min (A); MS: m/z = 374 (M + 1) P-29 6-[(2,6-difluoro-4- pyridyl)amino]-N- isopentyl-3-methoxy- pyridine-2- carboxamide [00062] 150-156 R.sub.t = 0.97 min (A); MS: m/z = 351 (M + 1) P-30 6-[(2,6-difluoro-4- pyridyl)amino]-N-(2,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00063] 50-60 R.sub.t = 0.96 min (A); MS: m/z = 351 (M + 1) P-31 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-(2- phenylethyl)pyridine- 2-carboxamide [00064] 45-52 R.sub.t = 0.96 min (A); MS: m/z =385 (M + 1) P-32 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-(2- phenylpropyl)pyridine- 2-carboxamide [00065] R.sub.t = 1.00 min (A); MS: m/z = 398 (M + 1) P-33 6-(isothiazol-4- ylamino)-3-methoxy- N-spiro[3.4]octan-3-yl- pyridine-2- carboxamide [00066] 125-128 R.sub.t = 0.97 min (A); MS: m/z = 359 (M + 1) P-34 N-(4,4-dimethylpent-2- ynyl)-6-(isothiazol-4- ylamino)-3-methoxy- pyridine-2- carboxamide [00067] 153-155 R.sub.t = 1.01 min (A); MS: m/z = 345 (M + 1) P-35 6-[(2,6-difluoro-4- pyridyl)amino]-N-(4,4- dimethylpent-2-ynyl)- 3-methoxy-pyridine-2- carboxamide [00068] 178-182 R.sub.t = 1.01 min (A); MS: m/z = 375 (M + 1) P-36 N-(1,5-dimethylhexyl)- 6-(isothiazol-4- ylamino)-3-methoxy- pyridine-2- carboxamide [00069] 84-86 R.sub.t = 1.07 min (A); MS: m/z = 363 (M + 1) P-37 N-[(4- chlorophenyl)methyl]- 6-(isothiazol-4- ylamino)-3-methoxy- pyridine-2- carboxamide [00070] 165-167 R.sub.t = 0.93 min (A); MS: m/z = 375 (M + 1) P-38 N-[2-(3,5- difluorophenoxy)-1- methyl-ethyl]-6- (isothiazol-4-ylamino)- 3-methoxy-pyridine-2- carboxamide [00071] 64-65 R.sub.t = 0.99 min (A); MS: m/z = 421 (M + 1) P-39 N-[2-(2,4- dichlorophenoxy)ethyl]- 6-(isothiazol-4- ylamino)-3-methoxy- pyridine-2- carboxamide [00072] 166-167 R.sub.t = 1.01 min (A); MS: m/z = 439 (M + 1) P-40 6- (cyclopropylmethyl- amino)-N-(2,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00073] R.sub.t = 0.81 min (A); MS: M/Z = 292 (M + 1) P-41 6-(cyclobutylamino)- N-(2,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00074] R.sub.t = 0.82 min (A); MS: m/z = 292 (M + 1) P-42 6-(2,3- dihydroxypropyl- amino)-N-(2,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00075] R.sub.t = 0.63 min (A); MS: m/z = 312 (M + 1) P-43 N-(2 2- dimethylpropyl)-6- (2,2- dimethylpropylamino)- 3-methoxy-pyridine-2- carboxamide [00076] R.sub.t = 0.89 min (A); MS: m/z = 308 (M + 1) P-44 6-(3,5-difluoroanilino)- N-(2,2- dimethylcyclobutyl)-3- ethoxy-pyridine-2- carboxamide [00077] 152-157 R.sub.t = 1.15 min (A); MS: m/z = 376 (M + 1) P-45 6-(3,5-difluoroanilino)- N-[2-(4- fluorophenoxy) cyclobutyl]- 3-methoxy- pyridine-2- carboxamide [00078] R.sub.t = 1.61 mi (C); MS: m/z = 444 (M + 1) P-46 6-(3,5-difluoroanilino)- 3-(difluoromethoxy)-N- (2,2- dimethylcyclobutyl) pyridine-2- carboxamide [00079] 158-161 R.sub.t = 1.19 min (A); MS: m/z = 398 (M + 1) P-47 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-[5- (trifluoromethyl)indan- 1-yl]pyridine-2- carboxamide [00080] R.sub.t = min 1.85 (C); MS: m/z = 465 (M + 1) P-48 N-[(3-benzylimidazol- 4-yl)methyl]-6-[(2,6- difluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00081] R.sub.t = 0.97 min (C); MS: m/z = 451 (M + 1) P-49 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-[[1- (trifluoromethyl) cyclopropyl]methyl] pyridine- 2-carboxamide [00082] R.sub.t = 1.56 min (C); MS: m/z = 403 (M + 1) P-50 N-(5- cyclopropyltetrahydro- furan-3-yl)-6-[(2,6- difluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00083] R.sub.t = 1.37 min (C); MS: m/z = 391 (M + 1) P-51 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-[(1- methylpyrazolo[3,4- b]pyridin-3- yl)methyl]pyridine-2- carboxamide [00084] R.sub.t = 1.27 min (C); MS: m/z = 426 (M + 1) P-52 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-[(8-methyl- 5-oxaspiro[3.5]nonan- 8-yl)methyl]pyridine-2- carboxamide [00085] R.sub.t = 1.59 min (C); MS: m/z = 433 (M + 1) P-53 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-[(3- methyltetrahydrofuran- 3-yl)methyl]pyridine- 2-carboxamide [00086] R.sub.t = 1.27 min (C); MS: m/z = 379 (M + 1) P-54 6-[(2,6-difluoro-4- pyridyl)amino]-N-(7,7- dimethyl-2- oxabicyclo[3.2.0]heptan- 6-yl)-3-methoxy- pyridine-2- carboxamide [00087] R.sub.t = 1.45 min (C); MS: m/z = 405 (M + 1) P-55 6-(3,5-difluoroanilino)- 3-methoxy-N-[5- (trifluoromethyl)indan- 1-yl]pyridine-2- carboxamide [00088] R.sub.t = 2.02 min (C); MS: m/z = 464 (M + 1) P-56 6-(3,5-difluoroanilino)- 3-methoxy-N-[6- (trifluoromethyl)indan- 1-yl]pyridine-2- carboxamide [00089] R.sub.t = 1.98 min (C); MS: m/z = 464 (M + 1) P-57 6-(3,5-difluoroanilino)- 3-methoxy-N-[(4- phenoxyphenyl)methyl] pyridine-2- carboxamide [00090] R.sub.t = 1.98 min (C); MS: m/z = 462 (M + 1) P-58 6-(3,5-difluoroanilino)- N-[(2,2-difluoro-1,3- benzodioxo1-4- yl)methyl]-3-methoxy- pyridine-2- carboxamide [00091] R.sub.t = 1.88 min (C); MS: m/z = 450 (M + 1) P-59 6-(3,5-difluoroanilino)- 3-methoxy-N-(2- oxabicyclo[3.2.0]heptan- 7-yl)pyridine-2- carboxamide [00092] R.sub.t = 1.55 mi n (C); MS: m/z = 375 (M + 1) P-60 6-(3,5-difluoroanilino)- N-(2,3- dihydrobenzofuran-3- ylmethyl)-3-methoxy- pyridine-2- carboxamide [00093] R.sub.t = 1.72 min (C); MS: m/z = 412 (M + 1) P-61 6-(3,5-difluoroanilino)- 3-methoxy-N-(1- tetrahydropyran-4- ylethyl)pyridine-2- carboxamide [00094] R.sub.t = 1.54 min (C); MS: m/z = 392 (M + 1) P-62 6-(3,5-difluoroanilino)- 3-methoxy-N-[[1- (trifluoromethyl) cyclopropyl] methyl]pyridine- 2-carboxamide [00095] R.sub.t = 1.76 min (C); MS: m/z = 402 (M + 1) P-63 6-(3,5-difluoroanilino)- N-[[4-(difluoromethyl)- 1-methyl-pyrazol-3- yl]methyl]-3-methoxy- pyridine-2- carboxamide [00096] R.sub.t = 1.48 min (C); MS: m/z = 424 (M + 1) P-64 6-(3,5-difluoroanilino)- 3-methoxy-N-(2- oxaspiro[3.3]heptan-6- yl)pyridine-2- carboxamide [00097] R.sub.t = 1.38 min (C); MS: m/z = 376 (M + 1) P-65 N-(5- cyclopropyltetrahydro- furan-3-yl)-6-(3,5- difluoroanilino)-3- methoxy-pyridine-2- carboxamide [00098] R.sub.t =1.59 min (C); MS: m/z = 390 (M + 1) P-66 N-[(3,5-dichloro-4- pyridyl)methyl]-6-(3,5- difluoroanilino)-3- methoxy-pyridine-2- carboxamide [00099] R.sub.t = 1.68 min (C); MS: m/z = 439 (M + 1) P-67 6-(3,5-difluoroanilino)- 3-methoxy-N-[(8- methyl-5- oxaspiro[3.5]nonan-8- yl)methyl]pyridine-2- carboxamide [00100] R.sub.t = 1.80 min (C); MS: m/z = 432 (M + 1) P-68 6-(3,5-difluoroanilino)- 3-methoxy-N-[(3- methyltetrahydrofuran- 3-yl)methyl]pyridine- 2-carboxamide [00101] R.sub.t = 1.49 min (C); MS: m/z = 378 (M + 1) P-69 6-(3,5-difluoroanilino)- 3-methoxy-N-[(2- methyltriazol-4- yl)methyl]pyridine-2- carboxamide [00102] R.sub.t = 1.34 min (C); MS: m/z = 375 (M + 1) P-70 6-(3,5-difluoroanilino)- 3-methoxy-N-(4- oxaspiro[2.4]heptan-6- yl)pyridine-2- carboxamide [00103] R.sub.t = 1.54 min (C) MS: m/z = 376 (M + 1) P-71 6-(3,5-difluoroanilino)- 3-methoxy-N-[1-(5- methyloxazol-2- yl)ethyl]pyridine-2- carboxamide [00104] R.sub.t = 1.55 min (C); MS: m/z = 389 (M + 1) P-72 6-(3,5-difluoroanilino)- 3-methoxy-N-[[1-[5- (trifluoromethyl)-2- pyridyl]cyclopropyl] methyl]pyridine-2- carboxamide [00105] R.sub.t = 1.93 min (C); MS: m/z = 479 (M + 1) P-73 N-[[1-(6-chloro-3- pyridyl)cyclopropyl] methyl]-6-(3,5- difluoroanilino)-3- methoxy-pyridine-2- carboxamide [00106] R.sub.t = 1.73 min (C); MS: m/z = 445 (M + 1) P-74 6-(3,5-difluoroanilino)- 3-methoxy-N-[2-[4- (trifluoromethoxy) phenyl]ethyl]pyridine-2- carboxamide [00107] R.sub.t = 1.98 min (C); MS: m/z = 468 M + 1) P-75 N-[2-(3,5-dichloro-2- pyridyl)-2- ethoxyimino-ethyl]-6- (3,5-difluoroanilino)-3- methoxy-pyridine-2- carboxamide [00108] R.sub.t = 1.99 min (C); MS: m/z = 510 (M + 1) P-76 6-(3,5-difluoroanilino)- N-(7,7-dimethyl-2- oxabicyclo[3.2.0]heptan- n-6-yl)-3-methoxy- pyridine-2- carboxamide [00109] R.sub.t = 1.66 min (C); MS: m/z = 404 (M + 1) P-77 6-(3,5-difluoroanilino)- N-(1-isopropylsulfonyl- 4-piperidyl)-3- methoxy-pyridine-2- carboxamide [00110] R.sub.t = 1.56 min (C); MS: m/z = 469 (M + 1) P-78 6-(3,5-difluoroanilino)- N-(1,1-dioxothian-4- yl)-3-methoxy- pyridine-2- carboxamide [00111] R.sub.t = 1.26 min (C); MS: m/z = 412 (M + 1) P-79 6-(isothiazol-4- ylamino)-3-methoxy- N-[5- (trifluoromethyl)indan- 1-yl]pyridine-2- carboxamide [00112] R.sub.t = 1.72 min (C); MS: m/z = 435 (M + 1) P-80 6-(isothiazol-4- ylamino)-3-methoxy- N-[[2- (trifluoromethyl) pyrimidin-5- yl]methyl]pyridine-2- carboxamide [00113] R.sub.t = 1.26 min (C); MS: m/z = 411 (M + 1) P-81 6-(isothiazol-4- ylamino)-3-methoxy- N-[(4- phenoxyphenyl)methyl] pyridine-2- carboxamide [00114] R.sub.t = min 1.70 (C); MS: m/z = 433 (M + 1) P-82 N-[(2,2-difluoro-1,3- benzodioxo1-4- yl)methyl]-6- (isothiazol-4-ylamino)- 3-methoxy-pyridine-2- carboxamide [00115] R.sub.t = 1.57 min (C); MS: m/z = 421 (M + 1) P-83 6-(isothiazol-4- ylamino)-3-methoxy- N-[[1- (trifluoromethyl) cyclopropyl] methyl]pyridine- 2-carboxamide [00116] R.sub.t = 1.41 min (C); MS: m/z = 373 (M + 1) P-84 6-(isothiazol-4- ylamino)-3-methoxy- N-[(8-methyl-5- oxaspiro[3.5]nonan-8- yl)methyl]pyridine-2- carboxamide [00117] R.sub.t = 1.44 min (C); MS: m/z = 403 (M + 1) P-85 6-(isothiazol-4- ylamino)-3-methoxy- N-[2-[4- (trifluoromethoxy) phenyl]ethyl] pyridine-2- carboxamide [00118] R.sub.t = 1.68 min (C); MS: M/Z = 439 (M + 1) P-86 6-(3,5-difluoroanilino)- N-(2,2- dimethylcyclobutyl)-3- prop-2-ynoxy-pyridine- 2-carboxamide [00119] R.sub.t = 1.13 min (A); MS: m/z = 386 (M + 1) P-87 6-(3,5-difluoroanilino)- N-(2,2- dimethylcyclobutyl)-3- isopropoxy-pyridine-2- carboxamide [00120] 174-177 R.sub.t = 1.19 min (A); MS: m/z = 390 (M + 1) P-88 N-(1- cyclohexylcyclopropyl)- 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00121] 185-187 R.sub.t = 1.09 min (A); MS: m/z = 403 (M + 1) P-89 6-[(2,6-difluoro-4- pyridyl)amino]-N-[1-(4- fluorophenyl) cyclopropyl]-3-methoxy- pyridine-2- carboxamide [00122] 221-223 R.sub.t = 0.99 min (A); MS: m/z = 415 (M + 1) P-90 N-[1-[(4- chlorophenyl)methyl] cyclopropyl]-6-[(2,6- difluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00123] R.sub.t = 1.06 mi (A); MS: m/z = 445 (M + 1) P-91 N-tert-butyl-6-[(2,6- difluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00124] 153-155 R.sub.t = 0.96 min (A); MS: m/z = 337 (M + 1) P-92 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-(1- methylcyclopropyl) pyridine-2-carboxamide [00125] 195-197 R.sub.t = 0.88 min (A); MS: m/z = 335 (M + 1) P-93 N-tert-butyl-6-(3,5- difluoroanilino)-3- methoxy-pyridine-2- carboxamide [00126] 182-185 R.sub.t 1.05 min (A); MS: m/z = 336 (M + 1) P-94 N-tert-butyl-6-(3,5- difluoroanilino)-3- ethoxy-pyridine-2- carboxamide [00127] 201-203 R.sub.t = 1.10 mi (A); MS: m/z = 350 (M + 1) P-95 N-tert-butyl-6-[(2,6- difluoro-4- pyridyl)amino]-3- ethoxy-pyridine-2- carboxamide [00128] R.sub.t = 1.01 min (A); MS: m/z = 351 (M + 1) P-96 N-tert-butyl-6-(3,5- difluoroanilino)-3- prop-2-ynoxy-pyridine- 2-carboxamide [00129] R.sub.t = 1.09 min (A); MS: m/z = 360 (M + 1) P-97 N-tert-butyl-6-(3,5- difluoroanilino)-3- isopropoxy-pyridine-2- carboxamide [00130] 182-186 R.sub.t = 1.14 min (A); MS: m/z = 364 (M + 1) P-98 N-tert-butyl-6-[(2,6- difluoro-4- pyridyl)amino]-3-prop- 2-ynoxy-pyridine-2- carboxamide [00131] R.sub.t = 0.99 min (A); MS: m/z = 361 (M + 1) P-99 N-tert-butyl-6-[(2,6- difluoro-4- pyridyl)amino]-3- isopropoxy-pyridine-2- carboxamide [00132] 202-205 R.sub.t = 1.06 min (A); MS: m/z = 365 (M + 1) P-100 6-[(2,6-difluoro-4- pyridyl)amino]-N-(2,2- dimethylpropyl)-3- hydroxy-pyridine-2- carboxamide [00133] R.sub.t = 1.15 mi n (A); MS: m/z = 337 (M + 1) P-101 6-(3,5-difluoroanilino)- N-(2,2- dimethylcyclobutyl)-4- methoxy-pyridine-2- carboxamide [00134] 147-152 R.sub.t = 1.20 min (A); MS: m/z = 351 (M + 1) P-102 6-[(2,6-difluoro-4- pyridyl)amino]-N-(1,5- dimethylhexyl)-3- methoxy-pyridine-2- carboxamide [00135] 74-76 R.sub.t = 1.13 min (A); MS: m/z = 393 (M + 1) P-103 N-tert-butyl-6-[(5- fluoro-3- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00136] R.sub.t = 0.86 min (A); MS: m/z = 319 (M + 1) P-104 N-(2,2- dimethylcyclobutyl)-6- [(5-fluoro-3- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00137] R.sub.t = 0.92 min (A); MS: m/z = 345 (M + 1) P-105 N-(2,2- dimethylpropyl)-6-[(5- fluoro-3- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00138] 182-187 R.sub.t = 0.88 min (A); MS: m/z = 333 (M + 1) P-106 6-[(2,6-difluoro-3-iodo- 4-pyridyl)amino]-N- (2,2-dimethylpropyl)- 3-hydroxy-pyridine-2- carboxamide [00139] R.sub.t = 1.25 min (A); MS: m/z = 463 (M + 1) P-107 6-(3,5-difluoroanilino)- 3-methoxy-N-(1- methylcyclopentyl) pyridine-2- carboxamide [00140] 188-190 R.sub.t = 1.11 min (A); MS: m/z = 362 (M + 1) P-108 6-(3,5-difluoroanilino)- 3-methoxy-N-(1- methylcyclohexyl) pyridine-2- carboxamide [00141] 188-190 R.sub.t = 1.15 min (A); MS: m/z = 376 (M + 1) P-109 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-(1- methylcyclopentyl) pyridine-2-carboxamide [00142] R.sub.t = 1.01 min (A); MS: m/z = 363 (M + 1) P-110 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-(1- methylcyclohexyl) pyridine-2- carboxamide [00143] 162-164 R.sub.t = 1.06 min (A); MS: m/z = 377 (M + 1) P-111 6-(3,5-difluoroanilino)- N-(2,2- dimethylpropyl) pyridine-2- carboxamide [00144] 162-164 R.sub.t = 1.13 min (A); MS: m/z = 320 (M + 1) P-112 N-tert-butyl-6-(3,5- difluoroanilino)pyridine- 2-carboxamide [00145] 166-167 R.sub.t =1.12 min (A); MS: m/z = 306 (M + 1) P-113 6-[(2,6-difluoro-4- pyridyl)amino]-N-(2,2- dimethylpropyl) pyridine-2- carboxamide [00146] 174-177 R.sub.t = 1.04 min (A); MS: m/z = 321 (M + 1) P-114 N-tert-butyl-6-[(2,6- difluoro-4- pyridyl)amino]pyridine- 2-carboxamide [00147] 195-197 R.sub.t = 1.03 min (A); MS: m/z = 307 (M + 1) P-115 N-[[3,5- bis(trifluoromethyl) phenyl]methyl]-6-(3,5- difluoroanilino)-3- methoxy-pyridine-2- carboxamide [00148] 169-170 R.sub.t = 1.16 min (A); MS: m/z = 306 (M + 1) P-116 N-tert-butyl-6-(3,5- difluoroanilino)-4- methoxy-pyridine-2- carboxamide [00149] 155-156 R.sub.t = 1.15 min (A); MS: m/z = 336 (M + 1) P-117 N-tert-butyl-6-(3,5- difluoroanilino)-3- methoxy-1-oxido- pyridin-1-ium-2- carboxamide [00150] R.sub.t = 0.85 min (A); MS: m/z = 352 (M + 1) P-118 6-(3,5-difluoroanilino)- 3-methoxy-N-(1- methylcyclobutyl) pyridine-2- carboxamide [00151] 80-82 R.sub.t = 1.06 min (A); MS: m/z = 348 (M + 1) P-119 6-(3,5-difluoroanilino)- N-(1- methylcyclopentyl) pyridine-2- carboxamide [00152] 157-159 R.sub.t = 1.18 min (A); MS: m/z = 332 (M + 1) P-120 6-[(2,6-difluoro-4- pyridyl)amino]-N-(1- methylcyclopentyl) pyridine-2- carboxamide [00153] 153-155 R.sub.t = 1.09 min (A); MS: m/z = 333 (M + 1) P-121 N-(3-cyanothietan-3- yl)-6-(3,5- difluoroanilino)-3- methoxy-pyridine-2- carboxamide [00154] 184-188 P-122 6-(3,5-difluoroanilino)- 3-methoxy-N-(3- methyltetrahydrofuran- 3-yl)pyridine-2- carboxamide [00155] 133-134 R.sub.t = 0.93 min (A); MS: m/z =364 (M + 1) P-123 N-(1- cyanocyclopentyl)-6- (3,5-difluoroanilino)-3- methoxy-pyridine-2- carboxamide [00156] 79-80 R.sub.t = 1.00 min (A); MS: m/z = 373 (M + 1) P-124 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-(3- methyltetrahydrofuran- 3-yl)pyridine-2- carboxamide [00157] 160-161 R.sub.t = 0.83 min (A); MS: m/z = 365 (M + 1) P-125 N-(1- cyanocyclopentyl)-6- [(2,6-difluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00158] 183-184 R.sub.t = 0.91 min (A); MS: m/z = 374 (M + 1) P-126 N-(1-cyanocyclobutyl)- 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00159] 197-198 R.sub.t = 0.87 min (A); MS: m/z = 360 (M + 1) P-127 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-(1- methylcyclobutyl) pyridine-2- carboxamide [00160] 91-102 R.sub.t = 0.96 min (A); MS: m/z = 349 (M + 1) P-128 6-(3,5-difluoroanilino)- 3-methoxy-N-(3- methyloxetan-3- yl)pyridine-2- carboxamide [00161] 187-188 R.sub.t = 0.88 min (A); MS: m/z = 350 (M + 1) P-129 N-(1-cyanocyclobutyl)- 6-(3,5-difluoroanilino)- 3-methoxy-pyridine-2- carboxamide [00162] 217-222 R.sub.t = 0.96 min (A); MS: m/z = 359 (M + 1) P-130 6-(3,5-dichloroanilino)- N-(2,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00163] R.sub.t = 1.86 min (C); MS: m/z = 382 (M + 1) P-131 6-(3,4-dichloroanilino)- N-(2,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00164] R.sub.t = 1.79 min (C); MS: m/z = 382 (M + 1) P-132 6-(3-chloro-4-methyl- anilino)-N-(2,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00165] R.sub.t = 1.78 min (C); MS: m/z = 362 (M + 1) P-133 N-(2,2- dimethylpropyl)-6-(4- fluoroanilino)-3- methoxy-pyridine-2- carboxamide [00166] R.sub.t = 1.51 min (C); MS: m/z = 332 (M + 1) P-134 6-(3-chloro-5-fluoro- anilino)-N-(2,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00167] R.sub.t = 1.75 min (C); MS: m/z = 366 (M + 1) P-135 6-(4-chloro-3,5- difluoro-anilino)-N- (2,2-dimethylpropyl)- 3-methoxy-pyridine-2- carboxamide [00168] R.sub.t = 1.77 min (C); MS: m/z = 384 (M + 1) P-136 N-(2,2- dimethylpropyl)-6-[(2- fluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00169] R.sub.t = 1.23 min (C); MS: m/z = 333 (M + 1) P-137 N-(2,2- dimethylpropyl)-6-(3- ethylanilino)-3- methoxy-pyridine-2- carboxamide [00170] R.sub.t = 1.69 min (C); MS: m/z = 342 (M + 1) P-138 6-(4-chloro-3-methyl- anilino)-N-(2,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00171] R.sub.t = 1.77 min (C); MS: m/z = 362 (M + 1) P-139 N-(2,2- dimethylpropyl)-6-(3- fluoroanilino)-3- methoxy-pyridine-2- carboxamide [00172] R.sub.t = 1.56 min (C); MS: m/z = 332 (M + 1) P-140 N-(2,2- dimethylpropyl)-3- methoxy-6-(3- methylanilino)pyridine- 2-carboxamide [00173] R.sub.t = 1.58 min (C); MS: m/z = 328 (M + 1) P-141 N-(2,2- dimethylpropyl)-3- methoxy-6-(4- methylanilino)pyridine- 2-carboxamide [00174] R.sub.t = 1.56 min (C); MS: m/z = 328 (M + 1) P-142 N-(2,2- dimethylpropyl)-6-(3- fluoro-4-methyl- anilino)-3-methoxy- pyridine-2- carboxamide [00175] R.sub.t = 1.66 min (C); MS: m/z = 346 (M + 1) P-143 6-(3-cyano-5-methyl- anilino)-N-(2,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00176] R.sub.t = 1.53 min (C); MS: m/z = 353 (M + 1) P-144 6-(4-chloro-3-fluoro- anilino)-N-(2,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00177] R.sub.t = 1.71 min (C); MS: m/z = 366 (M + 1) P-145 N-(2,2- dimethylpropyl)-3- methoxy-6-(3,4,5- trifluoroanilino) pyridine-2- carboxamide [00178] R.sub.t = 1.69 min (C); MS: m/z = 368 (M + 1) P-146 N-tert-butyl-6-(3- cyanoanilino)-3- methoxy-pyridine-2- carboxamide [00179] R.sub.t = 1.39 min (C); MS: M/Z = 325 (M + 1) P-147 N-tert-butyl-6-(3- cyano-5-fluoro- anilino)-3-methoxy- pyridine-2- carboxamide [00180] R.sub.t = 1.51 min (C); MS: m/z = 343 (M + 1) P-148 N-tert-butyl-6-(3,5- dichloroanilino)-3- methoxy-pyridine-2- carboxamide [00181] R.sub.t = 1.85 min (C); MS: m/z = 368 (M + 1) P-149 N-tert-butyl-6-(3,4- dichloroanilino)-3- methoxy-pyridine-2- carboxamide [00182] R.sub.t = 1.77 min (C); MS: m/z = 368 (M + 1) P-150 N-tert-butyl-3- methoxy-6-[4- (trifluoromethyl)anilino] pyridine-2- carboxamide [00183] R.sub.t = 1.69 min (C); MS: m/z = 368 (M + 1) P-151 N-tert-butyl-6-(3- chloro-4-methyl- anilino)-3-methoxy- pyridine-2- carboxamide [00184] R.sub.t = 1.74 min (C); MS: m/z = 348 (M + 1) P-152 N-tert-butyl-6-(3- chloro-5-fluoro- anilino)-3-methoxy- pyridine-2- carboxamide [00185] R.sub.t = 1.73 min (C); MS: m/z = 352 (M + 1) P-153 N-tert-butyl-6-(4- chloro-3,5-difluoro- anilino)-3-methoxy- pyridine-2- carboxamide [00186] R.sub.t = 1.76 min (C); MS: m/z = 370 (M + 1) P-154 N-tert-butyl-6-[3- fluoro-4- (trifluoromethyl)anilino]- 3-methoxy-pyridine- 2-carboxamide [00187] R.sub.t = 1.74 min (C); MS: m/z = 386 (M + 1) P-155 N-tert-butyl-6-(3- chloroanilino)-3- methoxy-pyridine-2- carboxamide [00188] R.sub.t = 1.64 min (C); MS: m/z = 334 (M + 1) P-156 N-tert-butyl-6-[(2- fluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00189] R.sub.t = 1.17 min (C); MS: m/z = 319 (M + 1) P-157 6-(benzofuran-5- ylamino)-N-tert-butyl- 3-methoxy-pyridine-2- carboxamide [00190] R.sub.t = 1.38 min (C); MS: m/z = 340 (M + 1) P-158 N-tert-butyl-6-(4- chloro-3-methyl- anilino)-3-methoxy- pyridine-2- carboxamide [00191] R.sub.t = 1.72 min (C); MS: m/z = 348 (M + 1) P-159 6-(1,3-benzodioxo1-5- ylamino)-N-tert-butyl- 3-methoxy-pyridine-2- carboxamide [00192] R.sub.t = 1.29 mi (C); MS: m/z = 344 (M + 1) P-160 N-tert-butyl-6-(3- fluoroanilino)-3- methoxy-pyridine-2- carboxamide [00193] R.sub.t = 1.52 min (C); MS: m/z = 318 (M + 1) P-161 N-tert-butyl-3- methoxy-6-(4- methylanilino)pyridine- 2-carboxamide [00194] R.sub.t = 1.48 min (C); MS: m/z = 314 (M + 1) P-162 N-tert-butyl-3- methoxy-6-(3,4,5- trifluoroanilino) pyridine-2- carboxamide [00195] R.sub.t = 1.66 min (C); MS: m/z = 354 (M + 1) P-163 N-tert-butyl-3- methoxy-6-[[5- (trifluoromethyl)-3- pyridyl]amino]pyridine- 2-carboxamide [00196] R.sub.t = 1.40 min (C); MS: M/Z = 369 (M + 1) P-164 N-tert-butyl-6-(4- cyano-3-fluoro- anilino)-3-methoxy- pyridine-2- carboxamide [00197] R.sub.t = 1.44 min (C); MS: m/z = 343 (M + 1) P-165 6-[(1-benzylindazol-6- yl)amino]-N-tert-butyl- 3-methoxy-pyridine-2- carboxamide [00198] R.sub.t = 1.47 min (C); MS: m/z = 430 (M + 1) P-166 N-tert-butyl-3- methoxy-6-(pyrimidin- 5-ylamino)pyridine-2- carboxamide [00199] R.sub.t = 0.95 min (C); MS: m/z = 302 (M + 1) P-167 6-[(2,6-difluoro-4- pyridyl)amino]-N-(1,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00200] R.sub.t = 0.97 min (A); MS: m/z = 351 (M + 1) P-168 6-(3,5-difluoroanilino)- N-(1,2- dimethylpropyl)-3- methoxy-pyridine-2- carboxamide [00201] R.sub.t = 1.06 min (A); MS: m/z = 350 (M + 1) P-169 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-(1,2,2- trimethylpropyl) pyridine-2- carboxamide [00202] R.sub.t = 1.01 min (A); MS: m/z = 365 (M + 1) P-170 6-(3,5-difluoroanilino)- 3-methoxy-N-(1,2,2- trimethylpropyl) pyridine-2- carboxamide [00203] R.sub.t = 1.10 min (A); MS: m/z = 364 (M + 1) P-171 6-(3,5-difluoroanilino)- 3-methoxy-N-(1,1,2,2- tetramethylpropyl) pyridine-2- carboxamide [00204] 213-216 R.sub.t = 1.14 min (A); MS: m/z = 378 (M + 1) P-172 6-(3,5-difluoroanilino)- 3-methoxy-N-(1,1,2- trimethylpropyl) pyridine-2- carboxamide [00205] 193-196 R.sub.t = 1.11 min (A); MS: m/z = 364 (M + 1) P-173 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-(1,1,2- trimethylpropyl) pyridine-2- carboxamide [00206] R.sub.t = 1.01 min (A); MS: m/z = 365 (M + 1) P-174 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-N-(1,1,2,2- tetramethylpropyl) pyridine-2- carboxamide [00207] 207-209 R.sub.t = 1.05 min (A); MS: m/z = 379 (M + 1) P-175 6-(3,5-difluoroanilino)- N-(2,2- dimethylcyclobutyl)-3- methyl-pyridine-2- carboxamide [00208] 156-158 R.sub.t = 1.21 mi (A); MS: m/z = 346 (M + 1) P-176 N-(1- cyclobutylcyclobutyl)- 6-(3,5-difluoroanilino)- 3-methoxy-pyridine-2- carboxamide [00209] 169-170 R.sub.t = 1.17 min (A); MS: m/z = 388 (M + 1) P-177 N-[1-(6-chloro-2- pyridyl)cyclobutyl]-6- (3,5-difluoroanilino)-3- methoxy-pyridine-2- carboxamide [00210] 80-81 R.sub.t = 1.10 min (A); MS: m/z = 445 (M + 1) P-178 6-(3,5-difluoroanilino)- N-(1-ethylcyclobutyl)- 3-methoxy-pyridine-2- carboxamide [00211] 163-164 R.sub.t = 1.07 min (A); MS: m/z = 362 (M + 1) P-179 6-(3,5-difluoroanilino)- N-(1- isopropylcyclobutyl)-3- methoxy-pyridine-2- carboxamide [00212] 189-190 R.sub.t = 1.12 min (A); MS: m/z = 376 (M + 1) P-180 N-(1-tert- butylcyclobutyl)-6- (3,5-difluoroanilino)-3- methoxy-pyridine-2- carboxamide [00213] 209-210 R.sub.t = 1.16 min (A); MS: m/z = 390 (M + 1) P-181 6-[(2,6-difluoro-4- pyridyl)amino]-N-(1- isopropylcyclobutyl)-3- methoxy-pyridine-2- carboxamide [00214] 80-81 R.sub.t = 1.03 min (A); MS: m/z = 377 (M + 1) P-182 N-(1- cyclobutylcyclobutyl)- 6-[(2,6-difluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00215] 85-86 R.sub.t = 1.05 min (Q); MS: m/z = 389 (M + 1) P-183 6-[(2,6-difluoro-4- pyridyl)amino]-N-(1- ethylcyclobutyl)-3- methoxy-pyridine-2- carboxamide [00216] 95-97 R.sub.t = 0.98 min (A); MS: m/z = 363 (M + 1) P-184 N-[1-(6-chloro-2- pyridyl)cyclobutyl]-6- [(2,6-difluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00217] R.sub.t = 1.02 min (A); MS: m/z = 446 (M + 1) P-185 N-(1-tert- butylcyclobutyl)-6- [(2,6-difluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00218] R.sub.t = 1.07 mi (A); MS: m/z = 391 (M + 1) P-186 N-[1-(6-chloro-3- pyridyl)cyclobutyl]-6- [(2,6-difluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00219] 120-121 R.sub.t = 0.95 min (A); MS: m/z = 446 (M + 1) P-187 N-[3-(4- chlorophenyl) cyclobutyl]-6-(3,S- difluoroanilino)-3- methoxy-pyridine-2- carboxamide [00220] 152-155 R.sub.t = 1.15 min (A); MS: m/z = 444 (M + 1) P-188 chlorophenyl) cyclobutyl]-6- [(2,6-difluoro-4- pyridyl)amino]-3- methoxy-pyridine-2- carboxamide [00221] 174-175 R.sub.t = 1.07 min (A); MS: m/z = 445 (M + 1) P-189 6-(N-acetyl-3,5- difluoro-anilino)-N- (2,2- dimethylcyclobutyl)-3- methoxy-pyridine-2- carboxamide [00222] 49-52 P-190 N-tert-butyl-6-(2- chloro-3,5-difluoro- anilino)-3-methoxy- pyridine-2- carboxamide [00223] R.sub.t = 1.09 min (A); MS: m/z = 370 (M + 1) P-191 methyl N-(3,5- difluorophenyl)-N-[6- [(2,2- dimethylcyclobutyl) carbamoyl]-5- methoxy-2- pyridyl]carbamate [00224] 98-100 P-192 6-[acetyl-(2,6-difluoro- 4-pyridyl)amino]-N- (2,2- dimethylcyclobutyl)-3- methoxy-pyridine-2- carboxamide [00225] 56-59 P-193 N-[1-(6-chloro-3- pyridyl)cyclobutyl]-6- (3,5-difluoroanilino)-3- methoxy-pyridine-2- carboxamide [00226] 182-184 R.sub.t = 1.04 min (A); MS: m/z = 445 (M + 1) Note : .sup.1H NMR Data for compound P-11: (400 MHz, DMSO-d.sub.6) δ 10.74 (s, 1H), 8.63-8.56 (m, 2H), 7.35 (s, 2H), 4.08 (d, J = 8.5 Hz, 1H), 3.87 (s, 3H), 2.08-2.05 (m, 1H), 1.96-1.88 (m, 1H), 1.50 (dd, J = 16.3, 8.0 Hz, 2H), 1.07 (d, J = 29.6 Hz, 6H).

BIOLOGICAL EXAMPLES

Example B1: Alternaria solani/Tomato/Leaf Disc (Early Blight)

[0291] Tomato leaf disks cv. Baby are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks are inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf disks are incubated at 23° C./21° C. (day/night) and 80% rh under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound is 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 following compounds gave at least 80% control of Alternaria solani at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-4, P-6, P-7, P-10, P-22, P-44, P-45, P-55, P-56, P-60, P-62, P-65, P-66, P-67, P-68, P-70, P-74, P-76, P-78, P-83, P-86, P-87, P-91, P-93, P-94, P-107, P-109, P-110, P-112, P-118, P-125, P-127, P-139, P-145, P-146, P-147, P-148, P-152, P-160, P-162, P-170, P-171, P-172, P-173, P-176, P-178, P-179, P-180, P-185.

Example B2: Botryotinia fuckeliana (Botrytis cinerea)/Liquid Culture (Gray Mould)

[0292] Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (Vogels broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24° C. and the inhibition of growth is determined photometrically 3-4 days after application. The following compounds gave at least 80% control of Botryotinia fuckeliana at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-7, P-42, P-93, P-112, P-116, P-118, P-119, P-120, P-132, P-134, P-139, P-142, P-145, P-151, P-152, P-155, P-160, P-162, P-168, P-170, P-171, P-172, P-173, P-175, P-176, P-178, P-179, P-189, P-190.

Example B3: Glomerella lagenarium (Colletotrichum lagenarium)/Liquid Culture (Anthracnose)

[0293] Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24° C. and the inhibition of growth is measured photometrically 3-4 days after application. The following compounds gave at least 80% control of Glomerella lagenarium at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-1, P-2, P-3, P-4, P-6, P-7, P-8, P-10, P-13, P-14, P-16, P-18, P-19, P-20, P-22, P-23, P-24, P-25, P-26, P-27, P-29, P-30, P-33, P-36, P-37, P-39, P-42, P-44, P-45, P-46, P-47, P-52, P-55, P-56, P-57, P-58, P-59, P-60, P-61, P-62, P-65, P-66, P-67, P-68, P-70, P-71, P-72, P-73, P-74, P-75, P-76, P-77, P-79, P-81, P-82, P-83, P-84, P-85, P-86, P-87, P-88, P-90, P-91, P-93, P-94, P-95, P-100, P-101, P-102, P-104, P-107, P-108, P-109, P-110, P-111, P-112, P-113, P-114, P-116, P-117, P-118, P-119, P-120, P-121, P-122, P-123, P-127, P-128, P-129, P-130, P-131, P-132, P-133, P-134, P-136, P-137, P-138, P-139, P-140, P-141, P-142, P-144, P-145, P-146, P-147, P-148, P-149, P-150, P-151, P-152, P-153, P-154, P-155, P-156, P-157, P-158, P-160, P-161, P-162, P-163, P-165, P-168, P-170, P-171, P-172, P-173, P-175, P-176, P-177, P-178, P-179, P-180, P-187, P-189, P-190, P-191.

Example B4: Blumeria graminis f. sp. tritici (Erysiphe graminis f. sp. tritici)/Wheat/Leaf Disc Preventative (Powdery Mildew on Wheat)

[0294] Wheat leaf segments cv. Kanzler are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks are inoculated by shaking powdery mildew infected plants above the test plates 1 day after application. The inoculated leaf disks are incubated at 20° C. and 60% rh under a light regime of 24 h darkness followed by 12 h light/12 h darkness in a climate chamber and the activity of a compound is 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). The following compounds gave at least 80% control of Blumeria graminis f. sp. tritici at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-4, P-6, P-7, P-9, P-10, P-11, P-20, P-21, P-22, P-25, P-26, P-29, P-30, P-44, P-45, P-48, P-50, P-51, P-52, P-53, P-54, P-57, P-59, P-61, P-62, P-64, P-65, P-67, P-68, P-70, P-74, P-76, P-83, P-91, P-92, P-93, P-94, P-95, P-103, P-104, P-105, P-107, P-108, P-109, P-110, P-112, P-113, P-114, P-117, P-118, P-121, P-122, P-123, P-124, P-125, P-127, P-128, P-134, P-139, P-145, P-147, P-152, P-153, P-156, P-160, P-162, P-164, P-166, P-167, P-168, P-169, P-170, P-171, P-172, P-173, P-176, P-177, P-178, P-179, P-180, P-181, P-182, P-183, P-185, P-189, P-192.

Example B5: Fusarium culmorum/Liquid Culture (Head Blight)

[0295] Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24° C. and the inhibition of growth is determined photometrically 3-4 days after application. The following compounds gave at least 80% control of Fusarium culmorum at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-7, P-107, P-108, P-168, P-176, P-178, P-179.

Example B6: Phaeosphaeria nodorum (Septoria nodorum)/Wheat/Leaf Disc Preventative (Glume Blotch)

[0296] Wheat leaf segments cv. Kanzler are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks are inoculated with a spore suspension of the fungus 2 days after application. The inoculated test leaf disks are incubated at 20° 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 is 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 following compounds gave at least 80% control of Phaeosphaeria nodorum at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-4, P-7, P-22, P-25, P-26, P-27, P-44, P-45, P-46, P-55, P-56, P-57, P-62, P-93, P-94, P-107, P-112, P-116, P-118, P-139, P-145, P-146, P-152, P-160, P-171, P-172, P-176, P-178, P-179, P-180, P-189, P-190.

Example B7: Monographella nivalis (Microdochium nivale)/Liquid Culture (Foot Rot Cereals)

[0297] Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24° C. and the inhibition of growth is determined photometrically 4-5 days after application. The following compounds gave at least 80% control of Monographella nivalis at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-1, P-2, P-3, P-4, P-5, P-6, P-7, P-8, P-10, P-12, P-13, P-14, P-15, P-16, P-17, P-18, P-19, P-22, P-23, P-25, P-26, P-27, P-29, P-33, P-36, P-37, P-38, P-39, P-40, P-43, P-44, P-45, P-46, P-47, P-55, P-56, P-57, P-60, P-62, P-65, P-66, P-67, P-68, P-70, P-73, P-74, P-75, P-76, P-79, P-81, P-82, P-83, P-86, P-87, P-91, P-93, P-94, P-95, P-96, P-102, P-104, P-106, P-107, P-108, P-109, P-110, P-111, P-112, P-113, P-114, P-117, P-118, P-119, P-120, P-121, P-122, P-123, P-127, P-131, P-132, P-133, P-134, P-138, P-139, P-140, P-144, P-145, P-146, P-147, P-148, P-150, P-151, P-152, P-153, P-155, P-157, P-160, P-162, P-168, P-170, P-171, P-172, P-173, P-175, P-176, P-177, P-178, P-179, P-180, P-181, P-183, P-185, P-187, P-189, P-190.

Example B8: Mycosphaerella arachidis (Cercospora arachidicola)/Liquid Culture (Early Leaf Spot)

[0298] Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24° C. and the inhibition of growth is determined photometrically 4-5 days after application. The following compounds gave at least 80% control of Mycosphaerella arachidis at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-7, P-19, P-22, P-23, P-26, P-27, P-36, P-44, P-45, P-46, P-55, P-56, P-57, P-62, P-67, P-74, P-79, P-93, P-94, P-102, P-107, P-108, P-118, P-139, P-145, P-152, P-160, P-162, P-168, P-171, P-172, P-176, P-178, P-179, P-180.

Example B9: Phakopsora pachyrhizi/Soybean/Preventative (Soybean Rust)

[0299] Soybean leaf disks are placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. One day after application leaf discs are inoculated by spraying a spore suspension on the lower leaf surface. After an incubation period in a climate cabinet of 24-36 hours in darkness at 20° C. and 75% rh leaf disc are kept at 20° C. with 12 h light/day and 75% rh. The activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (12-14 days after application). The following compounds gave at least 80% control of Phakopsora pachyrhizi at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-4, P-7, P-107, P-109, P-118, P-178, P-179.

Example B10: Puccinia recondita f. sp. tritici/Wheat/Leaf Disc Curative (Brown Rust)

[0300] Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format). The leaf segments are inoculated with a spore suspension of the fungus. Plates are stored in darkness at 19° C. and 75% rh. The formulated test compound diluted in water is applied 1 day after inoculation. The leaf segments are 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 is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (6-8 days after application). The following compounds gave at least 80% control of Puccinia recondita f. sp. tritici at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-4, P-91, P-93, P-107, P-109, P-118, P-127, P-156, P-160, P-162, P-178, P-185.

Example B11: Puccinia recondita f. sp. tritici/Wheat/Leaf Disc Preventative (Brown Rust)

[0301] Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks are inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments are 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 is 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 following compounds gave at least 80% control of Puccinia recondita f. sp. tritici at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-1, P-4, P-6, P-7, P-21, P-22, P-23, P-25, P-26, P-27, P-29, P-30, P-31, P-45, P-47, P-55, P-56, P-57, P-62, P-70, P-76, P-79, P-80, P-88, P-91, P-92, P-93, P-102, P-105, P-107, P-108, P-109, P-110, P-112, P-114, P-117, P-118, P-119, P-120, P-123, P-125, P-127, P-136, P-137, P-139, P-143, P-145, P-146, P-147, P-148, P-152, P-155, P-156, P-160, P-162, P-167, P-168, P-169, P-171, P-172, P-173, P-174, P-176, P-177, P-178, P-179, P-180, P-181, P-182, P-183, P-184, P-185, P-187, P-188, P-190.

Example B12: Magnaporthe grisea (Pyricularia oryzae)/Rice/Leaf Disc Preventative (Rice Blast)

[0302] Rice leaf segments cv. Ballila are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf segments are inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf segments are incubated at 22° C. and 80% rh under a light regime of 24 h darkness followed by 12 h light/12 h darkness in a climate cabinet and the activity of a compound is 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 following compounds gave at least 80% control of Magnaporthe grisea at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-4, P-6, P-7, P-10, P-20, P-21, P-22, P-23, P-25, P-26, P-27, P-29, P-30, P-32, P-33, P-35, P-44, P-45, P-46, P-47, P-49, P-52, P-55, P-57, P-60, P-61, P-62, P-65, P-66, P-67, P-68, P-69, P-70, P-71, P-74, P-76, P-87, P-88, P-89, P-90, P-91, P-93, P-94, P-95, P-102, P-103, P-104, P-105, P-107, P-108, P-109, P-110, P-111, P-112, P-113, P-117, P-118, P-119, P-120, P-122, P-123, P-125, P-126, P-127, P-128, P-129, P-139, P-144, P-145, P-146, P-147, P-148, P-151, P-152, P-153, P-155, P-156, P-159, P-160, P-162, P-164, P-177, P-180, P-185, P-189, P-192.

Example B13: Pyrenophora teres/Barley/Leaf Disc Preventative (Net Blotch)

[0303] Barley leaf segments cv. Hasso are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf segments are inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf segments are 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 is 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 following compounds gave at least 80% control of Pyrenophora teres at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-4, P-6, P-7, P-10, P-22, P-26, P-29, P-44, P-45, P-57, P-62, P-76, P-93, P-94, P-102, P-107, P-108, P-109, P-116, P-118, P-127, P-134, P-139, P-145, P-147, P-152, P-155, P-160, P-162, P-168, P-171, P-176, P-178, P-179, P-180, P-185.

Example B14: Sclerotinia sclerotiorum/Liquid Culture (Cottony Rot)

[0304] Mycelia fragments of a newly grown liquid culture of the fungus are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format) the nutrient broth containing the fungal material is added. The test plates are incubated at 24° C. and the inhibition of growth is determined photometrically 3-4 days after application. The following compounds gave at least 80% control of Sclerotinia sclerotiorum at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development P-4, P-10, P-19, P-44, P-67, P-74, P-107, P-108, P-109, P-122, P-123, P-139, P-145, P-147, P-152, P-157, P-160, P-162, P-180.

Example B15: Mycosphaerella graminicola (Septoria tritici)/Liquid Culture (Septoria Blotch)

[0305] Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24° C. and the inhibition of growth is determined photometrically 4-5 days after application. The following compounds gave at least 80% control of Mycosphaerella graminicola at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-1, P-2, P-3, P-4, P-6, P-7, P-8, P-10, P-16, P-18, P-19, P-20, P-22, P-23, P-25, P-26, P-27, P-28, P-29, P-30, P-32, P-33, P-34, P-35, P-36, P-37, P-38, P-39, P-40, P-41, P-43, P-44, P-45, P-46, P-47, P-55, P-56, P-57, P-58, P-59, P-60, P-62, P-65, P-66, P-67, P-68, P-70, P-71, P-73, P-74, P-75, P-76, P-79, P-83, P-91, P-93, P-94, P-96, P-102, P-104, P-107, P-108, P-109, P-110, P-111, P-112, P-113, P-114, P-115, P-117, P-118, P-119, P-120, P-121, P-122, P-123, P-127, P-128, P-129, P-130, P-132, P-133, P-134, P-135, P-139, P-140, P-144, P-145, P-146, P-147, P-148, P-151, P-152, P-153, P-155, P-157, P-160, P-162, P-168, P-170, P-171, P-172, P-173, P-174, P-175, P-176, P-177, P-178, P-179, P-180, P-181, P-183, P-185, P-187, P-189, P-190, P-191.