Patent EP-2017264-A1 (EP)
Inventor: TIEBES JOERG DR
IPC: C07C317/32
Filed: 2007-07-16
Abstract: Use of substituted phenyl propargyl compounds (I) or their salts, as herbicides or plant growth regulators, is claimed. Use of substituted phenyl propargyl compounds of formula (I) or their salts, as herbicides or plant growth regulators, is claimed. Q : carbocyclic aromatic residue with 6 ring atoms or heteroaromatic residue with 5-6 ring atoms, where: the heteroaromatic residue exhibits 1-4 N, or 1 S, or 1 S and 1 N as a hetero ring atoms and the carbocyclic aromatic residue or the heteroaromatic residue at one or more CH group is optionally substituted; A : unsaturated nitrogen containing divalent group of formula (-C(R 6>)=N-O-) (A1), (-C(R 6>)=N-N(R 7>)-) (A2), substituted pyrazole group of formula (A3)-(A5); R 2>1-6C-alkyl, 2-6C-alkenyl, 2-6C-alkynyl, 3-6C-cycloalkyl, 5-6C-cycloalkenyl, heterocycle with 3-6 ring atoms and 1-3 heteroring atoms of N, O or S, phenyl (all optionally substituted), or H; (R3) ne.g. CO 2R 20>, halo, CN, azido, SF 5, isocyanato, nitro, C(R1c)=N-OR1d or -C(SR1e)=NR1f; R 20>H, 1-6C-(halo)alkyl, (1-6C)-alkoxy-carbonyl, 1-6C-alkoxy-oxalyl or 3-6C-cycloalkyl (optionally substituted by one or more 1-4C-alkyl); R1c : H, 1-6C-(halo)alkyl, or 3-6C-cycloalkyl (optionally substituted by one or more (1-4C)-alkyl); R1d : H, 1-8C-(halo)alkyl, 2-8C-(halo)alkenyl or 2-8C-alkynyl; R1e : 1-6C-alkyl; R1f : H or 1-6C-alkyl; either R 4>, R 5>H, 1-4C-alkyl, 1-4C-haloalkyl or 3-6C-cycloalkyl (optionally substituted by one or more halo or (1-3C)-alkyl); or R 4>C, R 5>C : 3-6-membered ring, which is a carbocyclic or heterocyclic ring with 1 or 2 hetero ring atoms of N, O or S, where the ring is optionally substituted by one or more halo, 1-4C-alkyl, 1-4C-haloalkyl, 1-4C-alkoxy or 1-4C-haloalkoxy; R 6>1-6C-alkyl, 2-6C-alkenyl, 2-6C-alkynyl, phenyl, pyridyl, phenoxy, 3-6C-cycloalkyl, 5-6C-cycloalkenyl or saturated heterocyclic residue with 3-6 ring atoms and 1 or 2 heteroring atoms of N, O or S (all optionally substituted), or H; R 7>R 6>, formyl, COR, COOR, SOR or S(O) 2R; R : 1-6C-alkyl, 2-6C-alkenyl, 2-6C-alkynyl, phenyl, pyridyl, phenoxy, 3-6C-cycloalkyl, 5-6C-cycloalkenyl, a saturated heterocyclic residue with 3-6 ring atoms and 1 or 2 heteroring atoms of N, O or S or CONR1aR1b; R1a, R1b : 1-6C-alkyl, 2-6C-alkenyl, 2-6C-alkynyl, phenyl, pyridyl, phenoxy, 3-6C-cycloalkyl, 5-6C-cycloalkenyl or a saturated heterocyclic residue with 3-6 ring atoms and 1 or 2 heteroring atoms of N, O or S (all optionally substituted), or H; n : \-1; and either R 8>, R 9>1-6C-alkyl, 2-6C-alkenyl, 2-6C-alkynyl, halo, CN, carboxyl, formyloxy, nitro, OH, thio, phenyl, pyridyl, phenoxy, 3-6C-cycloalkyl, 5-6C-cycloalkenyl or a saturated heterocyclic residue with 3-6 ring atoms and 1 or 2 heteroring atoms of N, O or S, 1-6C-alkoxy, 1-6C-alkylthio, 2-6C-alkenyloxy, 3-6C-cycloalkoxy, 5-6C-cycloalkenyloxy, COOR, SOR, S(O) 2R, OCOOR, OSOR, OS(O) 2R, CONR1a or OCONR1aR1b (all optionally substituted) or H; or R 8>R 9>2-5C-alkylene chain, which can be interrupted by one or more heteroatom of N, O or S, and optionally substituted by one or more halo or (1-4C)-alkyl. Where the residue Q with the group (A) of (A1)-(A5) is bonded through unsaturated carbon atom, and the group CR 4>R 5>with group (A) in the formula (A1)-(A5) is bonded with the saturated heteroatom of group (A), the double bond in (A1) or (A2) is in Z or E configuration. An independent claim is included for 7 methods for the preparation of (I) comprising e.g. reacting a compound of formula (Q-A-H) (II) with a substituted benzene compound of formula (III); or reacting an acetylene compound of formula ((A-Q)(R 4>)(R 5>)C-C=?CH) (IV) with a substituted benzene compound of formula (V); or reacting an amide substituted benzene compound of formula (VI) with a carbonyl compound of formula (Q-CO-R 6>) (VII) to obtain (I) (in which A is (A1)); or reacting an amide substituted benzene compound of formula (VIII) with (VII) to obtain (I) (in which A is (A2)); or reacting a benzene substituted compound of formula (IX) with boron hydroxide compound of formula (Q-B(OH) 2) (X) under the condition of cross coupling to obtain (I) (in which A is (A3)-(A5)). X : leaving group. [Image] [Image] [Image] [Image] ACTIVITY : Herbicide. MECHANISM OF ACTION : None given.