Isothiazolo-based bicycles, processes for their preparation and their use as herbicides and/or plant growth regulators

Patent metadata

Field	Value
Publication number	US-10842152-B2
Application number	US-201816627983-A
Country	US
Kind code	B2
Filing date	Jun 28, 2018
Priority date	Jul 3, 2017
Publication date	Nov 24, 2020
Grant date	Nov 24, 2020

Abstract

The invention relates to the technical field of the herbicides and/or plant growth regulators. Specifically, the invention primarily relates to novel substituted isothiazolopyridones, and compositions comprising said novel substituted isothiazolopyridones. Further, the present invention relates to processes for the preparation said novel substituted isothiazolopyridones and their use as herbicides and/or plant growth regulators.

First claim

The invention claimed is:

1. A Compound of the formulae (G1) and (G2) and/or salt thereof

in which
A is CR 6 R 7 ,
x is 0, 1 or 2,
R 1 is hydrogen, (C 1 -C 8 )-alkyl, (C 2 -C 8 )-alkenyl, (C 2 -C 8 )-alkynyl, (C 1 -C 8 )-alkoxy, (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkylthio, (C 3 -C 8 )-cycloalkyl, (C 3 -C 8 )-cycloalkenyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkoxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkoxy, aryl, aryl-(C 1 -C 8 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 8 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 8 )-alkyl, aryloxy, heteroaryloxy, heterocyclyloxy, wherein all these residues are unsubstituted or substituted by one or more residues from the group consisting of halogen, nitro, hydroxyl, cyano, NR 13 R 14 , (C 1 -C 8 )-alkyl, (C 1 -C 8 )-haloalkyl, (C 1 -C 8 )-alkoxy, (C 1 -C 8 )-haloalkoxy, (C 1 -C 8 )-alkylthio, (C 1 -C 8 )-alkylsulphinyl, (C 1 -C 8 )-alkylsulphonyl, (C 1 -C 8 )-haloalkylthio, (C 1 -C 8 )-haloalkylsulphinyl, (C 1 -C 8 )-haloalkylsulphonyl, (C 1 -C 8 )-alkoxycarbonyl, (C 1 -C 8 )-haloalkoxycarbonyl, (C 1 -C 8 )-alkylcarboxy, (C 3 -C 8 )-cycloalkyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkoxycarbonyl-(C 1 -C 8 )-alkyl, hydroxycarbonyl, hydroxycarbonyl-(C 1 -C 8 )-alkyl, R 13 R 14 N-carbonyl, and wherein heterocyclyl has q oxo groups, and wherein each of the aforementioned heterocyclic residues, in addition to the carbon atoms, has in each case p ring members from the group consisting of N(R 12 ) m , O and S(O) n ,
R 2 , R 3 are each independently hydrogen, (C 1 -C 8 )-alkyl, (C 2 -C 8 )-alkenyl, (C 2 -C 8 )-alkynyl, (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkoxyphenyl, (C 1 -C 8 )-alkoxyphenyl-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkylcarbonyl, (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkylcarbonyl, (C 1 -C 8 )-alkoxycarbonyl, (C 2 -C 8 )-alkenyloxycarbonyl, (C 2 -C 8 )-alkynyloxycarbonyl, (C 1 -C 8 )-alkylcarbonyl, (C 2 -C 8 )-alkenylcarbonyl, (C 2 -C 8 )-alkynylcarbonyl, R 13 R 14 N-carbonyl, (C 1 -C 8 )-alkylthio, (C 1 -C 8 )-alkylthiocarbonyl, (C 1 -C 8 )-alkylsulphinyl, (C 1 -C 8 )-alkylsulphonyl, (C 1 -C 8 )-alkylthio-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkylsulphinyl-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkylsulphonyl-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkylthio-(C 1 -C 8 )-alkylcarbonyl, (C 1 -C 8 )-alkylsulphinyl-(C 1 -C 8 )-alkylcarbonyl, (C 1 -C 8 )-alkylsulphonyl-(C 1 -C 8 )-alkylcarbonyl, (C 1 -C 8 )-alkoxycarbonyl-(C 1 -C 8 )-alkylcarbonyl, (C 3 -C 8 )-cycloalkyl, (C 3 -C 8 )-cycloalkenyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkylcarbonyl, (C 3 -C 8 )-cycloalkenylcarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkylcarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 8 )-alkylcarbonyl, aryl, aryl-(C 1 -C 8 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 8 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 8 )-alkyl, arylcarbonyl, aryl-(C 1 -C 8 )-alkylcarbonyl, heteroarylcarbonyl, heteroaryl-(C 1 -C 8 )-alkylcarbonyl, heterocyclylcarbonyl, or heterocyclyl-(C 1 -C 8 )-alkylcarbonyl, wherein all these residues are unsubstituted or substituted by one or more residues from the group consisting of halogen, nitro, hydroxyl, cyano, NR 13 R 14 , (C 1 -C 8 )-haloalkyl, (C 1 -C 8 )-alkoxy, (C 1 -C 8 )-haloalkoxy, (C 1 -C 8 )-alkylthio, (C 1 -C 8 )-alkylsulphinyl, (C 1 -C 8 )-alkylsulphonyl, (C 1 -C 8 )-haloalkylthio, (C 1 -C 8 )-haloalkylsulphinyl, (C 1 -C 8 )-haloalkylsulphonyl, (C 1 -C 8 )-alkoxycarbonyl, (C 1 -C 8 )-haloalkoxycarbonyl, (C 1 -C 8 )-alkylcarboxy, (C 3 -C 8 )-cycloalkyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkoxycarbonyl-(C 1 -C 8 )-alkyl, hydroxycarbonyl, hydroxycarbonyl-(C 1 -C 4 )-alkyl, R 13 R 14 N-carbonyl, and wherein heterocyclyl has q oxo groups, and wherein each of the aforementioned heterocyclic residues, in addition to the carbon atoms, has in each case p ring members from the group consisting of N(R 12 ) m , O and S(O) n ,
or

NR 2 R 3 is —N═CR 8 R 9 or —N═S(O) n R 10 R 11 ,
R 4 , R 5 are each independently hydrogen, formyl, cyano, halogen, oxytetrahydropyranmethyl, (C 1 -C 8 )-alkoxycarbonyl, (C 1 -C 8 )-alkylcarbonyloxy, (C 1 -C 6 )-alkylcarbonyloxy-(C 1 -C 6 -alkyl, (C 1 -C 8 )-alkylsilyl, (C 2 -C 6 )-alkenylcarbonyl, (C 2 -C 6 )-alkynylcarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkylaminocarbonyl, aminocarbonyl, (C 1 -C 8 )-alkylcarboxy, (C 1 -C 8 )-alkyl, (C 2 -C 8 )-alkenyl, (C 2 -C 8 )-alkynyl, NR 13 R 14 , R 13 R 14 N—(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkoxy, (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkylthio, (C 1 -C 8 )-alkylsulphinyl, (C 1 -C 8 )-alkylsulphonyl, (C 1 -C 8 )-alkylthio-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkylsulphinyl-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkylsulphonyl-(C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 3 -C 8 )-cycloalkenyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkoxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkoxy, aryl, aryl-(C 1 -C 8 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 8 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 8 )-alkyl, aryloxy, heteroaryloxy, heterocyclyloxy, wherein all these residues are unsubstituted or substituted by one or more residues from the group consisting of halogen, hydroxyl, cyano, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkyl, (C 1 -C 8 )-haloalkyl, (C 1 -C 8 )-haloalkoxy, (C 1 -C 8 )-alkylthio, (C 1 -C 8 )-alkylsulphinyl, (C 1 -C 8 )-alkylsulphonyl, (C 1 -C 8 )-haloalkylthio, (C 1 -C 8 )-haloalkylsulphinyl, (C 1 -C 8 )-haloalkylsulphonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkoxyimino, (C 2 -C 6 )-alkenyloxyimino, (C 1 -C 6 )-alkyloxyimino, aminocarbonyl and wherein heterocyclyl has q oxo groups, and wherein each of the aforementioned heterocyclic residues, in addition to the carbon atoms, has in each case p ring members from the group consisting of N(R 12 ) m , O and S(O) n ,
provided that R 4 and R 5 are not hydrogen at the same time, and wherein R 4 and R 5 together do not form an aromatic ring,

R 6 , R 7 are each independently hydrogen, cyano, halogen, (C 1 -C 8 )-alkyl, (C 2 -C 8 )-alkenyl, (C 2 -C 8 )-alkynyl, or (C 3 -C 8 )-cycloalkyl,
R 8 , R 9 are each independently hydrogen, (C 1 -C 8 )-alkyl, (C 2 -C 8 )-alkenyl, (C 2 -C 8 )-alkynyl, (C 2 -C 8 )-alkenyloxy, (C 2 -C 8 )-alkynyloxy, NR 13 R 14 , (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkylthio-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkylsulphinyl-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkylsulphonyl-(C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 3 -C 8 )-cycloalkenyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 8 )-alkyl, aryl, aryl-(C 1 -C 8 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 8 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 8 )-alkyl, wherein all these residues are unsubstituted or substituted by one or more residues from the group consisting of halogen, nitro, hydroxyl, cyano, (C 1 -C 8 )-alkyl, (C 1 -C 8 )-haloalkyl, (C 1 -C 8 )-alkoxy, (C 1 -C 8 )-haloalkoxy, and wherein heterocyclyl has q oxo groups, and wherein each of the aforementioned heterocyclic residues, in addition to the carbon atoms, has in each case p ring members from the group consisting of N(R 12 ) m , O and S(O) n ,
R 10 , R 11 are each independently hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, pyridinyl, furanyl, thienyl, pyridinyl-(C 1 -C 6 )-alkyl, thienyl

Assignees

• Bayer Cropscience Ag

Inventors

• Rey Jullien
• Tiebes Joerg
• Mosrin Marc
• Droege Thomas
• Dietrich Hansjoerg
• Machettira Anu Bheemaiah
• Gatzweiler Elmar
• Rosinger Christopher Hugh
• Schmutzler Dirk
• Portz Daniela
• Ilg Kerstin
• Rinolfi Philippe

Classifications

• A01N43/90 Primary

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• C07D517/04 Primary

  Ortho-condensed systems · CPC title

• C07D513/04

  Ortho-condensed systems · CPC title