RESUMEN
The diamide insecticides act on the ryanodine receptor (RyR). The synthesis of various bicyclic anthranilic derivatives is reported. Their activity against the insect ryanodine receptor (RyR) and their insecticidal activity in the greenhouse is presented, as well as structure activity relationship considerations.
Asunto(s)
Diamida/farmacología , Insecticidas/química , Insecticidas/farmacología , Canal Liberador de Calcio Receptor de Rianodina/metabolismo , Spodoptera/efectos de los fármacos , ortoaminobenzoatos/farmacología , Animales , Áfidos , Diamida/síntesis química , Diamida/química , Relación Dosis-Respuesta a Droga , Insecticidas/síntesis química , Estructura Molecular , Spodoptera/metabolismo , Relación Estructura-Actividad , ortoaminobenzoatos/síntesis química , ortoaminobenzoatos/químicaRESUMEN
A novel class of experimental fungicides has been discovered, which consists of special quinolin-6-yloxyacetamides. They are highly active against important phytopathogens, such as Phytophthora infestans (potato and tomato late blight), Mycosphaerella graminicola (wheat leaf blotch) and Uncinula necator (grape powdery mildew). Their fungicidal activity is due to their ability to inhibit fungal tubulin polymerization, leading to microtubule destabilization. An efficient synthesis route has been worked out, which allows the diverse substitution of four identified key positions across the molecular scaffold.
Asunto(s)
Acetamidas/química , Antifúngicos/síntesis química , Moduladores de Tubulina/síntesis química , Acetamidas/síntesis química , Acetamidas/farmacología , Antifúngicos/química , Antifúngicos/farmacología , Phytophthora infestans/efectos de los fármacos , Quinolinas/química , Saccharomycetales/efectos de los fármacos , Relación Estructura-Actividad , Moduladores de Tubulina/química , Moduladores de Tubulina/farmacologíaRESUMEN
A novel class of experimental fungicides has been discovered, which consists of special tetrasubstituted imidazoles. They are highly active against important phytopathogens, such as Botrytis cinerea (grey mould), Uncinula necator (grape powdery mildew), Mycosphaerella graminicola (wheat leaf blotch) and Alternaria solani (potato and tomato early blight). Their fungicidal efficacy is due to their ability to promote fungal tubulin polymerization, which leads to a disruption of microtubule dynamics. These imidazoles are five-membered ring analogs of similar substituted triazolopyrimidines and pyridazines with the same mode of action. A concise four-step synthesis route has been used to prepare them from commercially available starting materials.
Asunto(s)
Fungicidas Industriales/química , Fungicidas Industriales/farmacología , Imidazoles/química , Imidazoles/farmacología , Enfermedades de las Plantas/microbiología , Moduladores de Tubulina/química , Moduladores de Tubulina/farmacología , Alternaria/efectos de los fármacos , Ascomicetos/efectos de los fármacos , Botrytis/efectos de los fármacos , Fungicidas Industriales/síntesis química , Imidazoles/síntesis química , Proteínas de Plantas/metabolismo , Plantas/metabolismo , Plantas/microbiología , Tubulina (Proteína)/metabolismo , Moduladores de Tubulina/síntesis químicaRESUMEN
Special tetrasubstituted pyridazines are potent fungicides by promoting the tubulin polymerisation, hereby disrupting the microtubule dynamics in the fungus. They are monocyclic analogs of similar substituted triazolopyrimidines and pyridopyrazines with the same mode of action. The fungicidal activity of these pyridazines was evaluated against the plant pathogens Botrytis cinerea (grey mould), Mycosphaerella graminicola (wheat leaf blotch) and Alternaria solani (potato and tomato early blight). Structure-activity relationship studies revealed the importance of a methyl and a chlorine substituent next to both ring nitrogen atoms and two aryl or heteroaryl groups in the other two pyridazine positions.
Asunto(s)
Antifúngicos/síntesis química , Antifúngicos/farmacología , Ascomicetos/efectos de los fármacos , Botrytis/efectos de los fármacos , Piridazinas/química , Piridazinas/farmacología , Moduladores de Tubulina/síntesis química , Animales , Antifúngicos/química , Piridazinas/síntesis química , Relación Estructura-Actividad , Porcinos , Moduladores de Tubulina/química , Moduladores de Tubulina/farmacologíaRESUMEN
Pro-pesticides of alpha-(2,6-dichloro-4-trifluoromethylphenylhydrazono)-4-nitrophenylacetonitrile have been prepared and tested against mite and insect pests. Variations in potency and spectrum were observed depending on the choice of cleavable pro-moiety. Cleavage of the pro-moiety was demonstrated in one case by measuring the rate of increase in the uncoupling activity using a mitochondrial preparation. Irradiation experiments have demonstrated a rapid isomerisation of the planar Z isomer to the E isomer, which is reversible.
Asunto(s)
Acetonitrilos/química , Hidrazonas/química , Insecticidas/síntesis química , Desacopladores/síntesis química , Acetonitrilos/farmacología , Animales , Áfidos/efectos de la radiación , Escarabajos/efectos de la radiación , Hidrazonas/farmacología , Estructura Molecular , Mariposas Nocturnas/efectos de la radiación , Profármacos/síntesis química , Profármacos/farmacología , Tetranychidae/efectos de la radiación , Desacopladores/farmacologíaRESUMEN
Substituted alpha-(phenylhydrazono)phenylacetonitrile derivatives have been discovered which constitute a series of potent uncouplers of oxidative phosphorylation. Systematic variation of substituents on both benzene rings has clearly demonstrated the importance of steric congestion around the ionisation site and delocalisation of negative charge in the anionic form. Replacement of the cyano group by other electron-withdrawing groups leads to a dramatic decrease in uncoupling activity. The sub-nanomolar levels of uncoupling activity found in certain members indicate that these compounds are the most potent uncouplers yet reported.