Novel Fungicidal Pyridylamidines
20170313660 · 2017-11-02
Assignee
Inventors
Cpc classification
C07D213/75
CHEMISTRY; METALLURGY
International classification
Abstract
The invention relates to compounds of formula (I) wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are as defined in the claims. The invention further provides compositions which comprise these compounds and to their use in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.
##STR00001##
Claims
1. A compound of formula (I) ##STR00045## wherein R.sup.1 and R.sup.2 independently represent hydrogen, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4fluoroalkyl or C.sub.3-C.sub.6cycloalkyl; or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached form a three to six-membered saturated cyclic group which may optionally contain one oxygen or one sulphur atom; R.sup.3 represents fluorine, chlorine, bromine, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 alkenyl, C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.4 alkoxy or C.sub.3-C.sub.6 cycloalkyl; R.sup.4 represents hydrogen, halogen, cyano, hydroxy, formyl, carboxy, amino, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxy or C.sub.3-C.sub.6 cycloalkyl; R.sup.5 represents hydrogen, halogen, cyano, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy or C.sub.3-C.sub.6 cycloalkyl; R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently represent hydrogen or C.sub.1-C.sub.6 fluoroalkoxy; wherein at least one of R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 represent C.sub.1-C.sub.6 fluoroalkoxy; or a tautomer, isomer, enantiomer, salt or N-oxide thereof.
2. A compound of formula (I) according to claim 1 wherein R.sup.1 and R.sup.2 independently represent hydrogen, C.sub.1-C.sub.4alkyl or cyclopropyl; R.sup.3 represents fluorine, chlorine, methyl, ethyl, ethenyl, propyl, propenyl, isopropyl, isopropenyl, cyclopropanyl, methoxy, ethoxy or C.sub.1-C.sub.2 fluoroalkyl; R.sup.4 represents hydrogen, halogen or C.sub.1-C.sub.4 alkyl; R.sup.5 represents hydrogen, halogen, cyano, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl, ethynyl or C.sub.1-C.sub.4 alkoxy.
3. A compound of formula (I) according to claim 1 wherein R.sup.1 and R.sup.2 independently represent hydrogen, methyl, ethyl, isopropyl, propyl or cyclopropyl; R.sup.3 represents methyl, ethyl, methoxy, fluorine and chlorine; R.sup.4 represents hydrogen, halogen or C.sub.1-C.sub.4 alkyl; R.sup.5 represents hydrogen, bromine, iodine, chlorine, cyano methyl, difluoromethyl, cyclopropyl, ethynyl or methoxy.
4. A compound of formula (I) according to claim 1 wherein R.sup.1 and R.sup.2 independently represent hydrogen, methyl, ethyl, isopropyl, propyl or cyclopropyl; R.sup.3 represents methyl, methoxy, fluorine or chlorine; R.sup.4 represents hydrogen or C.sub.1-C.sub.4 alkyl; R.sup.5 represents hydrogen, bromine, iodine, chlorine, cyano, methyl or difluoromethyl.
5. A compound of formula (I) according to claim 1 wherein R.sup.1 represents methyl; R.sup.2 represents ethyl; R.sup.3 represents methyl, methoxy, fluorine or chlorine; R.sup.4 represents hydrogen; R.sup.5 represents hydrogen, bromine, cyano or methyl.
6. A compound of formula (I) according to claim 1 wherein R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently represent hydrogen or C.sub.1-C.sub.4 fluoroalkoxy; wherein at least one of R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 represent C.sub.1-C.sub.4 fluoroalkoxy.
7. A compound of formula (I) according to claim 1 wherein R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently represent hydrogen or C.sub.1-C.sub.2 fluoroalkoxy; wherein at least one of R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 represent C.sub.1-C.sub.2 fluoroalkoxy.
8. A compound of formula (I) according to claim 1 wherein R.sup.9 and R.sup.10 are hydrogen.
9. A compound of formula (I) according to claim 1 wherein R.sup.8, R.sup.9 and R.sup.10 are hydrogen.
10. A compound of formula (I) according to claim 1 wherein R.sup.6, R.sup.8, R.sup.9 and R.sup.10 are hydrogen.
11. A compound of formula (I) according to claim 1 wherein R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are hydrogen.
12. A composition comprising a fungicidally effective amount of a compound of formula (I) as defined in claim 1, optionally comprising at least one additional active ingredient.
13. A method of controlling or preventing phytopathogenic diseases on useful plants or on propagation material thereof, which comprises applying to the useful plants, the locus thereof or propagation material thereof a fungicidally effective amount of a compound of formula (I) as defined in claim 1.
Description
FORMULATION EXAMPLES
[0304]
TABLE-US-00002 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 (7-8 mol — 2% — 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.
TABLE-US-00003 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
[0305]
TABLE-US-00004 active ingredient [compound of formula (I)] 10% octylphenol polyethylene glycol ether (4-5 mol of ethylene 3% oxide) calcium dodecylbenzenesulfonate 3% castor oil polyglycol ether (35 mol of ethylene oxide) 4% 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.
TABLE-US-00005 Dusts a) b) c) Active ingredient [compound of formula (I)] 5% 6% 4% 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
[0306]
TABLE-US-00006 Active ingredient [compound of formula (I)] 15% 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
[0307]
TABLE-US-00007 Active ingredient [compound of formula (I)] 8% 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
[0308]
TABLE-US-00008 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%
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
[0309]
TABLE-US-00009 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 0.5%.sup. in water) monoazo-pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2%.sup. 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
[0310] 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.
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.
SYNTHETIC EXAMPLES
[0311] Using techniques described below and in WO 12/146125 (pp. 370-378) together with further techniques known to the person skilled in the art, for example as found in WO 08/101682 (pp. 22-33), compounds of formula (I) may be prepared
Preparation of 3-(difluoromethoxy)cyclohexanol
[0312] ##STR00027##
[0313] To a solution of cyclohexane-1,3-diol (2.30 g) in of CH.sub.3CN (50 mL), FSO.sub.2CF.sub.2COOH (1.2 equiv.) was added dropwise at 50° C. for 1 hour. After stirring for 10 min, the mixture was poured into water, extracted with CH.sub.2Cl.sub.2, dried over Na.sub.2SO.sub.4, evaporated to dryness and further purified by chromatography on silica gel to provide 1.2 g of the title compound in 36% yield.
[0314] H.sup.1 NMR (400 MHz, CDCl.sub.3): δ 6.65 (t, 0.5H), 6.64 (t, 0.5H), 4.60 (m, 1H), 4.35 (m, 0.5H), 3.80 (m, 0.5H), 3.70 (m, 0.5H), 3.45 (m, 0.5H), 2.10-0.85 (m, 8H).
[0315] F.sup.19 NMR (376.5 MHz, CDCl.sub.3): δ −66.7 (s), −66.6 (s).
Preparation of N′-[5-bromo-6-[3-(difluoromethoxy)cyclohexoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine
[0316] ##STR00028##
[0317] To a solution of 3-(difluoromethoxy)cyclohexanol (358 mg, 2.16 mmol), triphenylphosphine (1 equiv.) and N′-(5-bromo-6-hydroxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (0.9 equiv) in THF (50 mL), diisopropyl azodicarboxylate (1.3 equiv.) was added at 60° C. After stirring for 12 hours, the mixture was concentrated to dryness and purified by chromatography on silica gel to isolate the title compound separately as 110 mg of the cis-isomer (14% yield) and 130 mg of the trans-isomer (17% yield).
[0318] H.sup.1 NMR (400 MHz, CDCl.sub.3; cis-isomer): δ 7.40 (broad s, 1H), 7.21 (s, 1H), 6.23 (t, 1H), 5.41 (m, 1H), 4.52 (m, 1H), 3.31 (m, 2H), 2.98 (s, 3H), 2.83 (s, 3H), 2.14 (m, 1H), 1.92 (m, 1H), 1.82 (m, 2H), 1.68 (m, 4H), 1.21 (t, 3H).
[0319] F.sup.19 NMR (376.5 MHz, CDCl.sub.3): δ −68.5 (s).
[0320] H.sup.1 NMR (400 MHz, CDCl.sub.3; trans-isomer): δ 7.37 (broad s, 1H), 7.24 (s, 1H), 6.21 (t, 1H), 4.98 (m, 1H), 4.18 (m, 1H), 3.20 (m, 2H), 3.00 (s, 3H), 2.50 (m, 1H), 2.34 (s, 3H), 2.10 (m, 1H), 2.02 (m, 1H), 1.83 (m, 1H), 1.61 (m, 2H), 1.38 (m, 2H), 1.20 (t, 3H).
[0321] F.sup.19 NMR (376.5 MHz, CDCl.sub.3): δ −69.5 (s).
Preparation of 4-(difluoromethoxy)cyclohexanol
[0322] ##STR00029##
[0323] To the mixture of cyclohexane-1,4-diol (11.6 g, 0.1 mol) and Na.sub.2SO.sub.4 (7.1 g, 0.05 Mol) in CH.sub.3CN (120 mL), FSO.sub.2CF.sub.2COOH (21.36 g, 0.12 mol) in CH.sub.3CN (30 mL) was added dropwise over a period of 1 hour to maintain the temperature at 40 to 45° C. After addition, the liquid was poured into 200 mL of water, extracted with DCM (100 mL*3). The combined extracts was dried over Na.sub.2SO.sub.4, evaporated, and finally purified by flash column chromatography on silica to give 6.2 g of the titled compound in 37% yield. Note: 4-(difluoromethoxy)cyclohexanol is quite unstable. It is best to use this compound to the next step reaction immediately after simple purification.
[0324] H.sup.1 NMR (400 MHz, CDCl.sub.3): δ 6.21 (t, 0.5H), 6.19 (t, 0.5H), 4.23 (m, 1H), 3.73 (m, 1H), 1.95 (m, 2H), 1.70 (m, 2H), 1.60 (m, 2H), 1.40 (m, 2H).
[0325] F.sup.19 NMR (376.5 MHz, CDCl.sub.3): δ −80.9 (s), −80.8 (s).
Preparation of cis-N′-[5-bromo-6-[4-(difluoromethoxy)cyclohexoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methylformamidine and racemic N′-[5-bromo-6-[4-(difluoromethoxy)cyclohexoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methylformamidine
[0326] ##STR00030##
[0327] Solid KOH (3.92 g, 70 mmol) was added to a solution of N′-(5-bromo-6-fluoro-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (5.48 g, 20 mmol), 4-(difluoromethoxy)cyclohexanol (3.98 g, 24 mmol) and 18-crown-6 (1.05 g, 4 mmol) in 80 mL toluene. The mixture was heated at 90° C. for 18 hours under nitrogen atmosphere. The reaction was cooled to 25° C. then the reaction mixture was poured into 80 mL of ice water, extracted with EtOAc (50 mL*3). The combined extracts were dried over Na.sub.2SO.sub.4, concentrated at reduced pressure, and purified by column chromatography on silica to give 1.0 g of the titled compound and 1.0 g of the racemate mixture of N′-[5-bromo-6-[4-(difluoromethoxy)cyclohexoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methylformamidine in 12% yield.
[0328] H.sup.1 NMR (400 MHz, CDCl.sub.3): δ 7.37 (broad s, 1H), 7.21 (s, 1H), 6.21 (t, 1H), 5.11 (brs, 1H), 4.36 (m, 1H), 3.30 (m, 2H), 3.00 (s, 3H), 2.97 (s, 3H), 2.35 (s, 3H), 2.05 (m, 4H), 1.68 (m, 4H), 1.17 (t, 3H).
[0329] F.sup.19 NMR (376.5 MHz, CDCl.sub.3 δ ppm): −76.3.5 (s).
Preparation of trans-N′-[5-bromo-6-[4-(difluoromethoxy)cyclohexoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methylformamidine
[0330] ##STR00031##
[0331] To a solution of 4-(difluoromethoxy)cyclohexanol (680 mg), triphenylphosphine (1.3 equiv) and N′-(5-bromo-hydroxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (1 equiv.) in THF (30 mL) was added at diisopropyl azodicarboxylate (1.3 equiv.) at 65° C. After stirring for 18 h, the mixture was cooled 25° C. and concentrated to dryness. The resulting crude residue was purified by column chromatography on silica gel to provide 400 mg of the title compound in 25% yield.
[0332] H.sup.1 NMR (400 MHz, CDCl.sub.3): δ 7.40 (broad s, 1H), 7.23 (s, 1H), 6.26 (t, 1H), 5.16 (m, 1H), 4.22 (m, 1H), 3.35 (m, 2H), 2.98 (s, 3H), 2.34 (s, 3H), 1.98 (m, 4H), 1.76 (m, 2H), 1.67 (m, 2H), 1.18 (m, 3H).
[0333] F.sup.19 NMR (376.5 MHz, CDCl.sub.3): δ −80.6 (s).
Preparation of N′-(5-cyano-6-hydroxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine
[0334] ##STR00032##
[0335] N′-(5-bromo-6-hydroxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (10.00 g) was dissolved in dry DMF (33 mL) to give a yellow/orange solution which was degassed for 5 min by bubbling argon. Zn(CN).sub.2 (1.1 equiv.) and Pd(PPh).sub.4 (0.20 equiv.) were introduced and the orange mixture was stirred at 120° C. overnight. The reaction mixture was cooled to 25° C., diluted with CH.sub.2Cl.sub.2 and washed with saturated NaHCO.sub.3 aqueous solution, water, dried over Na.sub.2SO.sub.4, filtered and concentrated to dryness. The crude residue was taken up in warm diethyl ether and then cooling slowly to −10° C. The brown suspension was filtered, washed with cold diethyl ether, and dried to provide 7.1 g of the title compound as a yellow solid in 88% yield.
[0336] H.sup.1 NMR (400 MHz, CDCl.sub.3): δ 13.80 (brs, 1H), 7.55 (s, 1H), 7.45 (m, 1H), 3.50 (m, 1H), 3.35 (m, 1H), 3.03 (s, 3H), 2.51 (s, 3H), 1.22 (m, 3H).
Preparation of trans N′-[5-cyano-6-[4-(difluoromethoxy)cyclohexoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine
[0337] ##STR00033##
[0338] To a solution of N′-(5-cyano-hydroxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (436 mg, 2 mmol), triphenylphosphine (786 mg, 3 mmol) and 4-(difluoromethoxy)cyclohexanol (664 mg, 4 mmol) in THF (20 mL), diisopropylazodicarboxylate (606 mg, 35 mmol) was added 60° C. After stirring for 12 h, the mixture was cooled to 25° C., concentrated to dryness, and the crude residue was purified by chromatography on silica gel to give 120 mg of the title compound in 16% yield.
[0339] H.sup.1 NMR (400 MHz, CDCl.sub.3): δ 7.43 (brs, 1H), 7.20 (s, 1H), 5.21 (m, 1H), 4.29 (m, 1H), 3.50 (brs, 1H), 3.35 (brs, 1H), 3.02 (s, 3H), 2.45 (s, 3H), 2.11 (m, 4H), 1.73 (m, 4H), 1.21 (m, 3H).
[0340] This table gives analytical data for compounds of formula (I) prepared using techniques described below and in WO 12/146125 (pp. 370-378) together with further techniques known to the person skilled in the art, for example as found in WO 08/101682 (pp. 22-33)
TABLE-US-00010 TABLE 55 R.sub.t (min); Compound MS-ESI No. Name Structure (m/z; (M + H).sup.+) 55.001 cis-N′-[5-bromo-6-[4- (difluoromethoxy)cycloh exoxy]-2-methyl-3- pyridyl]-N-ethyl-N- methyl-formamidine
Analytical Methods Used (Method a and Method B):
[0341] Mass spectra were recorded on a Mass Spectrometer from Shimadzu (SQD or ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 1.5 kV, Cone range: unknown, Extractor: 5.00 V, Source Temperature: 200° C., Desolvation Temperature: 250° C., Cone Gas Flow: 90 L/Hr, Desolvation Gas Flow: 90 L/Hr, Mass range: 50 to 900 Da) and an SPD-20A from LC from Shimadzu: Solvent degasser, binary pump, heated column compartment and ultraviolet detector. Column: Diamonsil C18 (2) 5 u 150*4.6 mm, Temp: 40° C., SPD-20A Wavelength range (nm): 210 to 500, Solvent Gradient: A=water+0.1% F.sub.3CCOOH, B=Acetonitrile+0.1% F.sub.3CCOOH; Gradient: 0 min 10% B, 90% A; 15 min 100% B; Flow 1.00 (ml/min)
BIOLOGICAL EXAMPLES
[0342] Blumeria graminis f. s. tritici (Erysiphe graminis f. sp. tritici)/Wheat/Leaf Disc Preventative (Powdery Mildew on Wheat)
[0343] Wheat leaf segments cv. Kanzler were placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks were inoculated by shaking powdery mildew infected plants above the test plates 1 day after application. The inoculated leaf disks were incubated at 20° C. and 60% 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 was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check leaf segments (6-8 days after application).
[0344] The following compounds gave at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development:
[0345] 55.001, 55.002, 55.003, 55.004, 55.005, 55.006, 55.007, 55.008, 55.009, 55.010, 55.011
[0346] Puccinia recondita f. sp. tritici/Wheat/Leaf Disc Preventative (Brown Rust)
[0347] Wheat leaf segments cv. Kanzler were placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments were incubated at 19° C. and 75% rh under a light regime of 12 h light/12 h darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7-9 days after application).
[0348] The following compounds gave at 200 ppm gave at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development:
[0349] 55.001, 55.002, 55.003, 55.004, 55.005, 55.006, 55.007, 55.008, 55.009, 55.010, 55.011
[0350] Puccinia recondita f. sp. tritici/Wheat/Leaf Disc Curative (Brown Rust)
[0351] 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 were stored in darkness at 19° C. and 75% rh. The formulated test compound diluted in water was applied 1 day after inoculation. The leaf segments were incubated at 19° C. and 75% rh under a light regime of 12 h light/12 h darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (6-8 days after application).
[0352] The following compounds gave at 200 ppm gave at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development:
[0353] 55.001, 55.002, 55.003, 55.004, 55.005, 55.006, 55.007, 55.008, 55.009, 55.010, 55.011
[0354] Phakopsora pachyrhizi/Soybean/Leaf Disk Preventative (Soybean Rust)
[0355] Four-week old soybean plants are sprayed in a spray chamber with the formulated test compound diluted in water. Leaf disks are cut from treated plants and placed on agar into 24-well plates one day after application. Leaf disks are inoculated by spraying them with a spore suspension on their lower leaf surface. After an incubation period in a climate cabinet of 24-36 hours in darkness at 20° C. and 75% rh, the leaf disks are then kept at 20° C. with 12 h light/day and 75% rh. The percentage leaf disk area covered by disease is assessed when an appropriate level of disease appears on untreated check plants (12-14 days after application).
[0356] The following compounds gave at 200 ppm gave at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development:
[0357] 55.001, 55.002, 55.003, 55.004, 55.005, 55.006, 55.007, 55.008, 55.009, 55.010, 55.011