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AssigneeBayer Aktiengesellschaft
InventorsKlaus-Helmut Müller, Ernst Rudolf F. Gesing, Mark Wilhelm Drewes, Johannes Rudolf Jansen, Rolf Kirsten, Joachim Kluth, Klaus König
Estimating the term…
The invention relates to novel thienylsulphonylamino(thio)carbonyl compounds of the formula (I), in which Q represents oxygen or sulphur, R1 represents cyano, halogen or in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, R2 represents cyano, halogen or in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and R3 represents in each case optionally substituted heterocyclyl having 5 ring members, at least one of which represents oxygen, sulphur or nitrogen and one to three others may represent nitrogen, and salts of compounds of the formula (I), to processes and novel intermediates for preparing the novel compounds and to their use as herbicides.
A compound of the Formula (XX)
Dependencies are inferred from the claim text.
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From the US filing history. Foreign family members aren’t listed.
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
Having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms: five-membered rings with one nitrogen atom and either one oxygen…
Having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms: five-membered rings with three ring hetero atoms
Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<: containing the group >N—CO—N< where at least one nitrogen atom is part of a…
Term ended 1 Jun 2019 (estimated)
The invention relates to novel thienylsulphonylamino(thio)carbonyl compounds, to a plurality of processes and novel intermediates for their preparation and to their use as herbicides.
It is already known that certain sulphonylaminocarbonyl compounds have herbicidal properties (cf. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266, DE 4029753). However, the activity of these compounds is not in all respects satisfactory.
This invention, accordingly, provides the novel thienylsulphonylamino(thio)carbonyl compounds of the general formula (I),
(Process (a))
1.3 g (6.8 mmol) of 2,4-dimethyl-thiophene-3-sulphonamide and 1.1 g (7 mmol) of 1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) are added successively to a solution of 1.6 g (6.4 mmol) of 5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 30 ml of acetonitrile. The reaction mixture is stirred at room temperature (about 20° C.) for approximately 15 hours and subsequently concentrated under waterpump vacuum. The residue is then taken up in methylene chloride and washed with 1N hydrochloric acid and then with water. The organic phase is dried with magnesium sulphate and filtered. The filtrate is concentrated under waterpump vacuum and the residue is recrystallized from isopropanol.
This gives 1.1 g (50% of theory) of 5-ethoxy-4-methyl-2-(2,4-dimethyl-thien-3-yl-sulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 158° C.