SUBSTITUTED FIVE-MEMBERED HETEROCYCLIC COMPOUNDS, FUNGICIDAL COMPOSITIONS CONTAINING THEM AND METHODS OF MAKING THEREOF

• Main Authors: PHILLIPS WENDELL G, MAO MICHAEL K, MA CHUN, FEVIG THOMAS
• Format: Patent
• Language: English; Polish
• Published: 29.08.2008
• Subjects: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; AGRICULTURE; ANIMAL HUSBANDRY; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; CHEMISTRY; FISHING; FORESTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HUNTING; METALLURGY; ORGANIC CHEMISTRY; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS; PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTSTHEREOF; TRAPPING

The fungicidal compound 4,5-dimethyl-N-2-propenyl-2-(trimethylsilyl)-3-thiophenecarboxamide (Formula (I) 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 (II) 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.