Microbiocidal quinoline (thio)carboxamide derivatives

Abstract

Compounds of the formula (I) wherein the substituents are as defined in Claim 1. Furthermore, the present invention relates to agrochemical compositions which comprise compounds of formula (I), to preparation of these compositions, and to the use of the compounds or compositions in agriculture or horticulture for combating, preventing or controlling infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi. ##STR00001##

Claims

1. A compound of formula (I) ##STR00018## wherein X is O or S; R.sub.1 is hydrogen, halogen, methyl or cyano; R.sub.2 is hydrogen, methyl or halogen; R.sub.3 and R.sub.4 are each independently selected from hydrogen, halogen and methyl; R.sub.5 is C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl or C.sub.3-C.sub.6 cycloalkyl, wherein the alkyl, alkenyl and cycloalkyl may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3 alkoxy and C.sub.1-C.sub.3 alkylthio; R.sub.6 is hydrogen, fluoro, chloro, cyano or C.sub.1-C.sub.4 alkyl; R.sub.7 is C.sub.4-C.sub.10 saturated or partially unsaturated heterocycle or heteroaryl, wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and is connected via a carbon or a nitrogen atom, and may be optionally substituted with one or more substituents independently selected from halogen, cyano, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 haloalkylthio and C.sub.3-C.sub.5 cycloalkyl; or a salt, enantiomer or N-oxide thereof.

2. A compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R.sub.1 is hydrogen, fluoro, chloro, methyl or cyano.

3. A compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R.sub.2 is hydrogen, methyl, chloro or fluoro.

4. A compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R.sub.3 and R.sub.4 are each independently selected from hydrogen and methyl.

5. A compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R.sub.5 is C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl or C.sub.3-C.sub.6 cycloalkyl, wherein the alkyl, alkenyl and cycloalkyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro and C.sub.1-C.sub.3 alkyl.

6. A compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R.sub.6 is hydrogen, fluoro, chloro or C.sub.1-C.sub.3 alkyl.

7. A compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R.sub.7 is thienyl, azetidinyl, pyrazolyl oxazolyl, 1,2,4-oxadiazolyl, thiazolyl, pyrrolidinyl, piperidyl (wherein one of the ring-member methylene groups may optionally represent C═O, C═CH.sub.2 or C=CF.sub.2), pyridazinyl, oxazinanyl, thiomorpholinyl, morpholinyl, indazolyl, 4,5-dihydro-3H-pyridazinyl or pyridinyl, wherein the thienyl, azetidinyl, pyrazolyl, oxazolyl, 1, 2, 4-oxadiazolyl, thiazolyl, pyrrolidinyl, piperidyl, pyridazinyl, oxazinanyl, thiomorpholinyl, morpholinyl, indazolyl, 4,5-dihydro-3H-pyridazinyl and pyridinyl may be optionally substituted with one or more substituents independently selected from fluoro, chloro cyano, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl and C.sub.3-C.sub.4 cycloalkyl.

8. A compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R.sub.1 is hydrogen, fluoro, chloro or methyl; R.sub.2 is hydrogen, chloro or fluoro; R.sub.3 is methyl and R.sub.4 is hydrogen; or R.sub.3 is hydrogen and R.sub.4 is methyl; or R.sub.3 is hydrogen and R.sub.4 is hydrogen; R.sub.5 is C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.3 alkenyl, cyclopropyl or cyclobutyl, wherein the alkyl, alkenyl, cyclopropyl and cyclobutyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro and chloro or one methyl group; and R.sub.6 is hydrogen, fluoro, chloro or methyl.

9. A compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R.sub.7 is thienyl, azetidinyl, pyrazolyl, oxazolyl, 1,2,4-oxadiazolyl, thiazolyl, pyrrolidinyl, piperidyl (wherein one of the ring-member methylene groups may optionally represent C=CF.sub.2), oxazinanyl, thiomorpholinyl, morpholinyl, indazolyl, 4,5-dihydro-3H-pyridazinyl or pyridinyl, wherein the thienyl, azetidinyl, pyrazolyl, oxazolyl, 1,2,4-oxadiazolyl, thiazolyl, pyrrolidinyl, piperidyl, oxazinanyl, thiomorpholinyl, morpholinyl, indazolyl, 4,5-dihydro-3H-pyridazinyl and pyridinyl may be optionally substituted with one or two substituents independently selected from fluoro, chloro, methyl, trifluoromethyl and cyclopropyl.

10. A compound according to claim 1 wherein X is O or S; R.sub.1 is hydrogen, fluoro, chloro or methyl; R.sub.2 is hydrogen, chloro or fluoro; R.sub.3 is methyl and R.sub.4 is hydrogen; or R.sub.3 is hydrogen and R.sub.4 is methyl; or R.sub.3 is hydrogen and R.sub.4 is hydrogen; R.sub.5 is C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.3 alkenyl, cyclopropyl or cyclobutyl, wherein the alkyl, alkenyl, cyclopropyl and cyclobutyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro and chloro or one methyl group; R.sub.6 is hydrogen, fluoro, chloro or methyl; R.sub.7 is thienyl, azetidinyl, pyrazolyl, oxazolyl, 1,2,4-oxadiazolyl, thiazolyl, pyrrolidinyl, piperidyl (wherein one of the ring-member methylene groups may optionally represent C=CF.sub.2), oxazinanyl, thiomorpholinyl, morpholinyl, indazolyl, 4,5-dihydro-3H-pyridazinyl or pyridinyl, wherein the thienyl, azetidinyl, pyrazolyl, oxazolyl, 1,2,4-oxadiazolyl, thiazolyl, pyrrolidinyl, piperidyl, oxazinanyl, thiomorpholinyl, morpholinyl, indazolyl, 4,5-dihydro-3H-pyridazinyl and pyridinyl may be optionally substituted with one or two substituents independently selected from fluoro, chloro, methyl, trifluoromethyl and cyclopropyl; or a salt, enantiomer or N-oxide thereof.

11. A compound according to claim 1 wherein X is O or S; R.sub.1 is fluoro, chloro or methyl; R.sub.2 is hydrogen or fluoro; R.sub.3 and R.sub.4 are both hydrogen; R.sub.5 is trifluoromethyl, ethyl, isopropyl, tert-butyl, C.sub.2-alkenyl or cyclopropyl, wherein the ethyl, isopropyl, alkenyl and cyclopropyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro and chloro or one methyl group; R.sub.6 is methyl; R.sub.7 is thienyl, azetidinyl, thiazolyl, pyrrolidinyl, piperidyl (wherein one of the ring-member methylene groups may optionally represent C=CF.sub.2) or pyridinyl, wherein the thienyl, azetidinyl, thiazolyl, pyrrolidinyl, piperidyl, and pyridinyl may be optionally substituted with one or two substituents independently selected from fluoro, chloro, methyl or trifluoromethyl; or a salt, enantiomer or N-oxide thereof.

12. A compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein X is O.

13. A composition comprising a fungicidally effective amount of a compound of formula (I) as defined claim 1.

14. A composition according to claim 13, wherein the composition further comprises at least one additional active ingredient and/or a diluent.

15. A method of combating, preventing or controlling phytopathogenic fungi which comprises applying to phytopathogenic fungi, to the locus of phytopathogenic fungi, or to a plant susceptible to attack by phytopathogenic fungi, or to propagation material thereof, a fungicidally effective amount of a compound of formula (I) as defined in claim 1 or a composition comprising a fungicidally effective amount of the compound of formula (I).

16. A compound selected from: ##STR00019##

Description

EXAMPLES

(1) The Examples which follow serve to illustrate the invention. Certain 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.

(2) Throughout this description, temperatures are given in degrees Celsius and “m.p.” means melting point. LC/MS means Liquid Chromatography Mass Spectroscopy and the description of the apparatus and the methods are:

(3) Method G:

(4) Spectra were recorded on a Mass Spectrometer (ACQUITY UPLC) from Waters (SQD, SQDII or ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature: 150° C., Desolvation Temperature: 350° C., Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. 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 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH, gradient: 10-100% B in 1.2 min; Flow (ml/min) 0.85

(5) Method H:

(6) Spectra were recorded on a Mass Spectrometer (ACQUITY UPLC) from Waters (SQD, SQDII or ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature: 150° C., Desolvation Temperature: 350° C., Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. 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 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH, gradient: 10-100% B in 2.7 min; Flow (ml/min) 0.85

(7) Method I:

(8) Spectra were recorded on a Mass Spectrometer (ACQUITY UPLC) from Waters (SQD, SQDII or ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary (kV) 3.5, Cone (V) 30.00, Extractor (V) 3.00, Source Temperature (° C.) 150, Desolvation Temperature (° C.) 400, Cone Gas Flow (L/Hr) 60, Desolvation Gas Flow (L/Hr) 700, Mass range: 140 to 800 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. 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., DAD Wavelength range (nm): 210 to 400. Solvent Gradient A: Water/Methanol 9:1, 0.1% formic acid and Solvent B: Acetonitrile, 0.1% formic acid

(9) TABLE-US-00002 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

Formulation Examples

(10) 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% —
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.

(11) 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%
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.
Emulsifiable Concentrate

(12) TABLE-US-00005 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  4% ethylene oxide) Cyclohexanone 30% xylene mixture 50%
Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

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

(14) TABLE-US-00007 Active ingredient [compound of 15% formula (I)] sodium lignosulfonate  2% carboxymethylcellulose  1% Kaolin 82%
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.
Coated Granules

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

(16) TABLE-US-00009 Active ingredient [compound of 40% formula (I)] propylene glycol 10% nonylphenol polyethylene glycol ether  6% (15 mol of ethylene oxide) Sodium lignosulfonate 10% carboxymethylcellulose  1% silicone oil (in the form of a 75%  1% emulsion in water) Water 32%
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.
Flowable Concentrate for Seed Treatment

(17) TABLE-US-00010 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 0.5%  (in the form of a 20% solution in water) monoazo-pigment calcium salt  5% Silicone oil (in the form of a 75% 0.2%  emulsion in water) Water 45.3%  
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

(18) 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 polyvinylalcohol, 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.

(19) 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. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

Preparation Examples

Example 1: This example illustrates the preparation of 2-[(5-chloro-2-thienyl)methyl]-N-(8-fluoro-3-quinolyl)-2,4-dimethyl-pentanamide

Step 1: Preparation of ethyl 2-[(5-chloro-2-thienyl)methyl]-2,4-dimethyl-pentanoate

(20) To a solution of ethyl 2,4-dimethylpentanoate (0.36 g, 2.28 mmol) in tetrahydrofuran (0.25 M, 9.1 mL) at −70° C. was added a solution of lithium diisopropylamide (2 M in THF, 1.3 equiv., 1.5 mL, 2.96 mmol). The solution was stirred at −70° C. for 1 h. 2-chloro-5-(chloromethyl)thiophene (1.3 equiv., 0.37 mL, 2.96 mmol) was then added and the orange solution was allowed to warmup to rt and stirred at this temperature for 16 h. The reaction mixture was quenched with a saturated aqueous solution of NH.sub.4Cl. The two phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated. Purification of the residue by flash chromatography gave ethyl 2-[(5-chloro-2-thienyl)methyl]-2,4-dimethyl-pentanoate (0.25 g, 38% yield) as a yellow liquid: LC-MS (Method G), Rt=1.35 min;

(21) .sup.1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.91 (d, 6H) 1.15 (s, 3H) 1.28 (t, 3H) 1.45 (m, 1H) 1.68-1.75 (m, 2H) 2.71 (d, 1H) 3.19 (d, 1H) 4.14 (q, 2H) 6.52 (d, 1H) 6.70 (d, 1H).

Step 2: Preparation of 2-[(5-chloro-2-thienyl)methyl]-N-(8-fluoro-3-quinolyl)-2,4-dimethyl-pentanamide

(22) To a solution of ethyl 2-[(5-chloro-2-thienyl)methyl]-2,4-dimethyl-pentanoate (0.075 g, 0.26 mmol, 1.05 equiv.) in toluene (0.22 M, 1.2 mL) was added 8-fluoroquinolin-3-amine (1.0 equiv., 0.040 g, 0.25 mmol) followed by a solution of trimethyl aluminium (2 M in toluene) (1.3 equiv., 0.16 mL, 0.32 mmol) dropwise. The brown solution was stirred at 90° C. for 16 h. The reaction mixture was quenched by the addition of an aqueous sodium hydroxide solution (1 M). The two phases were separated and the aqueous phase was extracted with dichloromethane. The organic phase was washed with brine, dried over Na.sub.2SO.sub.4, filtered and concentrated. Purification of the residue by flash chromatography gave 2-[(5-chloro-2-thienyl)methyl]-N-(8-fluoro-3-quinolyl)-2,4-dimethyl-pentanamide (0.038 g, 38% yield) as a beige solid: mp=142-145° C.; LC-MS (Method G), Rt=1.22 min;

(23) .sup.1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.87 (d, 3H) 0.93 (d, 3H) 1.35 (s, 3H) 1.48 (dd, 1H) 1.78 (m, 1H) 1.90 (dd, 1H) 2.73 (d, 1H) 3.34 (d, 1H) 6.52 (d, 1H) 6.65 (d, 1H) 7.29 (t, 1H) 7.44 (m, 1H) 7.55 (d, 1H) 7.63 (s, 1H, NH) 8.62 (s, 1H) 8.80 (s, 1H).

(24) TABLE-US-00011 TABLE E Physical data of compounds of formula (I) RT [M + H] MP Entry STRUCTURE (min) (measured) Method ° C. E1 1.22 407 G 142- 145

Biological Examples

(25) Botryotinia fuckeliana (Botrytis cinerea)/Liquid Culture (Gray Mould)

(26) 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.

(27) 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:

(28) E1.

(29) Glomerella Lagenarium (Colletotrichum lagenarium)/Liquid Culture (Anthracnose)

(30) 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.

(31) 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:

(32) E1.

(33) Fusarium culmorum/Liquid Culture (Head Blight)

(34) 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.

(35) 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:

(36) E1.

(37) Gaeumannomyces graminis/Liquid Culture (Take-all of Cereals)

(38) 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 microtiter plate (96-well format), the nutrient broth containing the fungal spores iss added. The test plates are incubated at 24° C. and the inhibition of growth is determined photometrically 4-5 days after application.

(39) The following compounds gave at least 80% control of Gaeumannomyces graminis at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

(40) E1.

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

(42) 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.

(43) The following compounds gave at least 80% control of Monographella nivalis at 20 ppm when compared to untreated control under thb same conditions, which showed extensive disease development:

(44) E1.

(45) Magnaporthe grisea (Pyricularia oryzae)/Liquid Culture (Rice Blast)

(46) 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.

(47) The following compounds gave at least 80% control of Magnaporthe grisea at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

(48) E1.