- Carbonyl reduction of triadimefon by human and rodent 11β- hydroxysteroid dehydrogenase 1
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11β-Hydroxysteroid dehydrogenase 1 (11β-HSD1) catalyzes the conversion of inactive 11-oxo glucocorticoids (endogenous cortisone, 11-dehydrocorticosterone and synthetic prednisone) to their potent 11β-hydroxyl forms (cortisol, corticosterone and prednisolone). Besides, 11β-HSD1 accepts several other substrates. Using rodent liver microsomes and the unspecific inhibitor glycyrrhetinic acid, it has been proposed earlier that 11β-HSD1 catalyzes the reversible conversion of the fungicide triadimefon to triadimenol. In the present study, recombinant human, rat and mouse enzymes together with a highly selective 11β-HSD1 inhibitor were applied to assess the role of 11β-HSD1 in the reduction of triadimefon and to uncover species-specific differences. To further demonstrate the role of 11β-HSD1 in the carbonyl reduction of triadimefon, microsomes from liver-specific 11β-HSD1-deficient mice were employed. Molecular docking was applied to investigate substrate binding. The results revealed important species differences and demonstrated the irreversible 11β-HSD1-dependent reduction of triadimefon. Human liver microsomes showed 4 and 8 times higher activity than rat and mouse liver microsomes. The apparent Vmax/ Km of recombinant human 11β-HSD1 was 5 and 15 times higher than that of mouse and rat 11β-HSD1, respectively, indicating isoform-specific differences and different expression levels for the three species. Experiments using inhibitors and microsomes from 11β-HSD1-deficient mice indicated that 11β-HSD1 is the major if not only enzyme responsible for triadimenol formation. The IC50 values of triadimefon and triadimenol for cortisone reduction suggested that exposure to these xenobiotica unlikely impairs the 11β-HSD1-dependent glucocorticoid activation. However, elevated glucocorticoids during stress or upon pharmacological administration likely inhibit 11β-HSD1-dependent metabolism of triadimefon in humans.
- Meyer, Arne,Vuorinen, Anna,Zielinska, Agnieszka E.,Da Cunha, Thierry,Strajhar, Petra,Lavery, Gareth G.,Schuster, Daniela,Odermatt, Alex
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p. 1370 - 1378
(2013/08/25)
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- Synergistic Combinations Of Active Ingredients
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The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and A have the meanings given in the description and, secondly, at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.
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- Synergistic Active Compound Combinations Comprising Phenyltriazoles
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The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and R2 have the meanings given in the description. and at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.
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- Synergistic Fungidical Active Substance Combinations
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The present invention relates to novel active substance combinations which contain spiroxamine, which is known, a known azole and a known carboxamide and which are very suitable for controlling undesired phytopathogenic fungi.
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- Pyrazolyl benzyl ether derivatives containing a fluoromethoxyimino group and use thereof as pesticides
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The invention relates to novel pyrazolyl benzyl ethers, to a plurality of processes for their preparation and to their use for controlling harmful organisms.
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- Wood preservatives
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Wood preservatives having biocidal properties which include quaternary ammonium compounds of general formula (I): wherein R1 is a C8-18-alkyl group or an optionally substituted benzyl group, R2 is a C8-18-alkyl group, R3 is a C1-4-alkyl group or a group of the formula —[CH2—CH2—O]n—H, R4 is a C1-4-alkyl group, n is a number from 0.5 to 8, preferably from 1 to 5, and A?is the anion of an organic carboxylic acid which contains 2 to 12 C atoms and carries at least one hydroxyl, amino or sulfonic acid group. The wood preservatives also penetrate deeply into the wood without the use of pressure, and have only a mild corrosive action on metals. Furthermore, a process for treating timbers with these compositions, concentrates for the preparation thereof, the use of new and known quaternary ammonium compounds in wood preservatives and new quaternary ammonium compounds and their use as biocides.
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- Iminoacetic acid amides and their use as pest control agents
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PCT No. PCT/EP96/04345 Sec. 371 Date Apr. 15, 1998 Sec. 102(e) Date Apr. 15, 1998 PCT Filed Oct. 7, 1996 PCT Pub. No. WO97/14673 PCT Pub. Date Apr. 24, 1997Iminoacetamides of the formula (I) in which A represents a single bond or optionally substituted alkylene, Q represents oxygen or sulphur, R1 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R2 represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R3 represents hydrogen or respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl, R4 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclcyl a process for their preparation, pesticidal compositions containing them, and their use for controlling pests.
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- Microbicidal benzotriazoles
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Novel benzotriazoles of the formula STR1 in which R, X1, X2, X3, X4 and Y have the meanings given in the description, and their acid addition salts and metal salt complexes, a process for the preparation of these substances and their use as microbicides in crop protection and in material protection.
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- Halogen alkenyl azolyl microbicides
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Novel halogenoalkenyl-azolyl derivatives of the formula STR1 in which R1 represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, optionally substituted aryl or represents optionally substituted heteroaryl, R2 represents alkyl, halogenoalkyl, 1-hydroxyalkyl, 2-hydroxyalkyl, 1-hydroxyhalogenalkyl, 1-alkenyl or 2-alkenyl, X1 represents fluorine, chlorine, bromine or iodine, X2 represents fluorine, chlorine, bromine or iodine, and Y represents nitrogen or a CH group, and addition products thereof with acids or metal salts are very active as microbicides in plant protection and in the protection of materials.
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- Acylated 5-aminopyrazoles and the use thereof to combat animal parasites
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The present invention relates to new acylated 5-aminopyrazoles of the formula (I) STR1 in which R1, R2, R3, R4 and R5 have the meaning given in the description, to processes for their preparation and to their use as pesticides.
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- Substituted tetrahydro-5-nitro-pyrimidines
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The present invention relates to novel substituted in that one tetrahydro-5-nitro-pyrimidine of the formula (I), according to claim 1, STR1 in which n, R1, R2 have the meaning given in the description, to a process for its preparation and to its use for combating animal pests, especially insects, arachnids and nematodes, which are encountered in agricultural, in forestry, in the protection of stored products and of materials and, in the hygiene sector.
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- The effect on soil fertility of repeated applications of pesticides over 20 years
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Concern has been expressed that repeated use of pesticides may be leading to accumulation of residues in soil and to damaging effects on the environment. A long-term experiment, known as the Chemical Reference Plots, was started in 1974 on a silty clay loam soil at Rothamsted in which plots received applications of up to five pesticides (aldicarb, benomyl, chlorfenvinphos, glyphosate and chlorotoluron or triadimefon), each plot receiving the same treatment annually for up to 20 years. Spring barley was grown each year, and its yield was taken as an indicator of soil fertility. The glyphosate and triadimefon were applied to the autumn stubble prior to ploughing from growing seasons 1980 and 1982 respectively, chlorotoluron was sprayed pre-emergence (1974 and 1976 only) and the other compounds were incorporated into the soil in spring immediately before sowing (1974-1993 inclusive). No deleterious effects on crop productivity were observed from these pesticide applications, and no differences could be found in microbial processes in soils sampled in April 1992 save for a small increase in the amount of microbial-biomass carbon in plots receiving aldicarb. No pesticide residues could be detected in soil taken in August 1994, 17 months after the last experimental treatment. In laboratory incubations using these same soil samples, the degradation of aldicarb residues was greatly enhanced in plots that had received aldicarb for 20 years, whereas degradation rates of benomyl, chlorfenvinphos and triadimefon residues were not influenced by the treatment history.
- Bromilow,Evans,Nicholls,Todd,Briggs
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- Phototransformation of triadimefon on glass and soil surfaces
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Photodegradation of triadimefon has been studied on glass and soil surfaces. A number of photoproducts have been isolated and characterised by NMR, IR and MS. Photolysis resulted in considerable amounts of 1-(4- chlorophenoxymethyl)-1,2,4-triazole, 1-(4-chlorophenoxy)-2,2-dimethyl-1- (1,2,4-triazol-1-yl)propane, 1-(1,2,4-triazol-1-yl)-3,3-dimethylbutan-2-one and 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol. Rates of photodegradation on glass and soil surfaces under UV and sunlight followed first-order kinetics with a significant correlation coefficient. Photodegradation was greater on alluvial soil than on laterite soil.
- Nag,Dureja
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p. 247 - 252
(2007/10/03)
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- Diastereoselectivity in the Boranate Reduction of α-Triazolyl Ketones
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The influence of TiCl4 on the formation of diastereomers during the boranate reduction of α-triazolyl ketones 1 is investigated.Without TiCl4 the formation of diastereomer 3 with the hydroxy and triazole group syn to each other is preferred.However, in the presence of TiCl4 the diastereomer 2 with anti position of hydroxy and triazole group is formed with high selectivity.
- Thieme, Peter C.,Sauter, Hubert,Reissenweber, Gernot
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p. 1059 - 1062
(2007/10/02)
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- A Facile Synthesis of Ketene O,N-Acetals and Ketene O,O-Acetals by Tosylate Elimination
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Reaction of the alcohols 4 and 5 with p-toluensulfonyl chloride leads to the sulfonic esters 6 and 7, respectively, which on treatment with potassium tert-butylate easily react to give the ketene O,N-acetals 8 and O,O-acetals 9, respectively.The (E/Z) isomers 8 arising from the elimination reaction of 7 were identified by their 1H-NMR data after X-ray analysis of one of the isomers of 8e.On one example it is shown that the elimination reaction proceeds stereoselectively "anti".
- Reuther, Wolfgang,Ruland, Alfred,Baus, Ulf
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p. 235 - 240
(2007/10/02)
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- Process and intermediates for the synthesis of diastereomeric compounds
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A new process for the controlled synthesis of the two diasteromeric forms of triazolyl-O,N-acetals of the formula STR1 in which R represents optionally substituted phenyl, optionally substituted phenoxy, optionally substituted alkoxy, optionally substituted alkoxy, optionally substituted alkylthio, alkylcarbonyl, nitro or halogen and n represents an integer from 0 to 5, with the proviso that R can represent identical or different radicals, if n represents an integer from 2 to 5. New trans-substituted oxiranes and their use as intermediates for the synthesis of compounds of the formula (I).
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- DIASTEREOSPECIFIC SYNTHESIS OF FUNGICIDAL THREO- AND ERYTHRO-α-HYDROXY AMINALS
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Sequential reactions of 2-chloro- or 2-bromo-3-tert-butyloxirane with p-chlorophenolate and then with sodium triazolate lead in two stereocontrolled steps to threo-Triadimenol; by inverse addition of the two nucleophiles the erythro-isomer is obtained.
- Gasteiger, Johann,Kaufmann, Karlheinz
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p. 4341 - 4344
(2007/10/02)
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- Preparation of 1-azolyl-3,3-dimethyl-1-phenoxybutan-2-ols
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A process for the preparation of a 1-azolyl-3,3-dimethyl-1-phenoxybutan-2-ol of the formula STR1 in which X is a nitrogen atom or the CH group, Y is halogen, alkyl, alkoxycarbonyl, nitro or optionally substituted phenyl, and n is 0,1,2 or 3. comprising reacting a 1-azolyl-3,3-dimethyl-1-phenoxybutan-2-one of the formula STR2 with a secondary alcoholate under pressure in the presence of a diluent. Advantageously the reaction is carried out at a temperature about 20° to 40° C. above the boiling point of the diluent which is a secondary alcohol, the alcoholate is aluminum isopropylate and is present in about 0.35 to 0.4 mol per mol of ketone, and the reaction is carried out under an excess pressure of about 1.5 to 5 bar.
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- Preparation of 1-azolyl-3,3-dimethyl-1-phenoxy-butan-2-ols
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A process for the preparation of a 1-azolyl-3,3-dimethyl-1-phenoxy-butan-2-ol of the formula STR1 in which X is a nitrogen atom or a CH group, Y each independently is halogen, phenyl, phenoxy, nitro, alkyl, alkoxy or cycloalkyl, and n is 0, 1, 2 or 3, comprising reacting a 1-azolyl-3,3-dimethyl-1-phenoxy-butan-2-one of the formula STR2 with formic acid/triethylamine in the form of a 5:2 addition compound of the formula The product is a known fungicide.
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- Combating fungi with 1-azol-1-yl-1-phenoxy-2-alkane ethers
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Azolyl ether derivatives of the formula STR1 in which A is CH or a nitrogen atom, R is alkyl, alkenyl, alkynyl, phenyl, benzyl or substituted phenyl or benzyl, X is halogen, alkyl, alkoxy, alkylthio, alkylsulphonyl, halogenoalkyl, alkoxycarbonyl, nitro, cyano, phenyl, phenoxy, phenylthio, or substituted phenyl, phenoxy of phenylthio, Y is alkyl, phenyl, or substituted alkyl or phenyl and n is 0, 1, 2, 3, 4 or 5, which possess fungicidal properties.
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- Antimicrobial agents and their use
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The invention involves the provision of compositions containing a 3,3-dialkyl- or 3-aryl-phenoxy-1-(1,2,4-triazol-1-yl)- and (imidazol-1-yl-alkan-2-ol) ethers which are particularly effective as antimicrobial especially antimycotic, agents. The invention also includes use of said compositions for providing antimicrobial, particularly antimycotic effect.
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- Compositions containing O,N-acetal and method of using same
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Pharmaceutical compositions comprising a triazolyl-O,N-acetal as the active ingredient and method of using same. The said compositions are useful as antimicrobials and are especially useful as antimycotic agents.
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