C - Chemistry – Metallurgy – 07 – F
Patent
C - Chemistry, Metallurgy
07
F
C07F 7/08 (2006.01) A01N 43/10 (2006.01) A01N 55/10 (2006.01) A01P 3/00 (2006.01) C07D 333/38 (2006.01)
Patent
CA 2334221
The fungicidal compound 4,5-dimethyl-N-2-propenyl-2-(trimethylsilyl)-3- thiophenecarboxamide (Formula (I)) has shown superior and unexpected control of the growth of the soil-borne fungus Gaeumannomyces graminis (Gg). The present invention provides a novel compound for synthesizing the compound of Formula (I) which uses the compound 4-hydroxy-4,5-dimethyl-2-trimethylsilanyl-dihydrothiophene-3-carboxylic acid allylamide (Formula (II)) as well as novel compounds of synthesizing the allylamide. In addition, Formula (H) itself has unexpectedly been found to provide control of Gg. Therefore, the compounds having Formula (III) or an agronomic salts and compositions thereof are expected to provide such control as well; wherein Q is -NH, S, or O; W is O, or S; X is -OH, -OAc, -OR, where R is lower alkyl; Y is S, O, or -NH; Z is -Si(R)3, -C(R)3, where R is lower alkyl; R1 is a lower alkyl, allyl, or propargyl; R2 is a lower alkyl or aryl; and R3 and R4 are independently chosen from hydrogen, a lower alkyl and aryl; optionally, R2 and R3 together form a 5- or 6-membered ring.
On a constaté avec surprise que la composition fongicide 4,5diméthyl-N-2-propényl-2(triméthylsilyl)-3-thiophène carboxamide (formule I) permettait de combattre efficacement le champignon terricole Gaeumannomyces graminis (Gg). La présente invention concerne un nouveau composé permettant la synthèse du composé de formule (I) et faisant intervenir le composé 4-hydroxy-4,5-diméthyl-2-triméthylsilanyl-dihydrothiopène-3-acide carboxylique allyamide (formule (II)) ainsi que des composés permettant la synthèse de l'allyamide. De plus, il est apparu contre toute attente que le composé de formule (II) lui-même permettait de combattre Gg. On peut donc escompter des résultats analogues de composés de formule (III) ou de sels et compositions de ces composés utilisés en agronomie dans lesquels: Q est -NH, S ou O; W est O ou S; X est -OH, -OAc, -OR, dans lequel R représente un alkyle inférieur; Y est S, O, ou -NH; Z est -Si(R)3, -C(R)3, dans lequel R est un alkyle inférieur; R1 est un alkyle inférieur, un allyle ou un propargyle; R2 est un alkyle ou un aryle inférieur; et R3 et R4 sont pris indépendamment dans le groupe constitué par hydrogène, alkyle ou aryle inférieur; éventuellement, R2 et R3 forment ensemble un noyau à 5 ou 6 éléments.
Fevig Thomas L.
Ma Chun
Mao Michael K.
Phillips Wendell G.
Mcfadden Fincham
Monsanto Company
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