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US 2006/0052247 A1Published application
Novel herbicides
AssigneeSyngenta Crop Protection AG
InventorsRenaud Beaudegnies, Andrew Edmunds, Christoph Luthy, Roger Hall, Sebastian Wendeborn, Jurgen Schaetzer
Life of this patent
Estimating the term…
Abstract
Compounds of formula (I), wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula I are suitable for use as herbicides.
Claims7
A compound of formula I
- wherein
- Y is oxygen, NR4a, sulfur, sulfonyl, sulfinyl, C(O), C(═NR4b), C(═CR6aR6b) or a C1-C4alkylene or C2-C4alkenylene chain, which may be interrupted by oxygen, NR5a, sulfur, sulfonyl, sulfinyl, C(O) or C(═NR5b) and/or mono- or poly-substituted by R6;
- A1 is nitrogen or CR7;
- A2 is nitrogen or CR8;
- R1, R2, R6, R7 and R8 are each independently of the others hydrogen, hydroxy, mercapto, NO2, cyano, halogen, formyl, oxyiminomethylene, C1-C6alkoxyiminomethylene, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C3-C6oxacycloalkyl, C3-C6thiacycloalkyl, C3-C6dioxacycloalkyl, C3-C6dithiacycloalkyl, C3-C6oxathiacycloalkyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyloxy, C1-C6alkylcarbonyloxy, C1-C6alkylthio, C1-C6-alkylsulfonyl, C1-C6alkylsulfinyl, NR9R10, C3-C6cycloalkyl, tri(C1-C6alkyl)silyl, di(C1-C6alkyl)-phenylsilyl, tri(C1-C6alkyl)silyloxy, di(C1-C6alkyl)phenylsilyloxy or Ar1;
- or R1, R2, R6, R7, R8 are each independently of the others a C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl or C3-C6cycloalkyl group, which may be interrupted by oxygen, sulfur, sulfonyl, sulfinyl, —NR11— or —C(O)— and/or mono-, di- or tri-substituted by hydroxy, mercapto, NO2, cyano, halogen, formyl, C1-C6alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6haloalkoxy, C1-C2alkoxy-C1-C2alkoxy, C1-C4alkoxycarbonyloxy, C1-C4alkylcarbonyloxy, C1-C4alkoxycarbonyl, C1-C4alkylcarbonyl, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, NR12R13, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, tri(C1-C6alkyl)silyl, tri(C1-C6alkyl)silyloxy or Ar2;
- or two substituents R6 at the same carbon atom together form a —CH2O— or a C2-C5alkylene chain, which may be interrupted once or twice by oxygen, sulfur, sulfinyl or sulfonyl and/or mono- or poly-substituted by R6c, with the proviso that two hetero atoms may not be located next to one another;
- or two substituents R6 at different carbon atoms together form an oxygen bridge or a C1-C4alkylene chain, which may in turn be substituted by R6c;
- or R7 and R8 together form a —CH2CH═CH—, —OCH═CH— or —CH═CH—CH═CH— bridge or a C3-C4alkylene chain, which may be interrupted by oxygen or —S(O)n1— and/or mono- or poly-substituted by R6d;
- R3 is hydroxy, halogen, mercapto, C1-C8alkylthio, C1-C8alkylsulfinyl, C1-C8alkylsulfonyl, C1-C8haloalkylthio, C1-C8haloalkylsulfinyl, C1-C8haloalkylsulfonyl, C1-C4alkoxy-C1-C4alkylthio, C1-C4alkoxy-C1-C4alkylsulfinyl, C1-C4alkoxy-C1-C4alkylsulfonyl, C3-C8alkenylthio, C3-C8-alkynylthio, C1-C4alkylthio-C1-C4alkylthio, C3-C4alkenylthio-C1-C4alkylthio, C1-C4alkoxycarbonyl-C1-C4alkylthio, C1-C4alkoxycarbonyl-C1-C4alkylsulfinyl, C1-C4alkoxycarbonyl-C1-C4alkylsulfonyl, C3-C8cycloalkylthio, C3-C8cycloalkylsulfinyl, C3-C8cycloalkylsulfonyl, phenyl-C1-C4alkylthio, phenyl-C1-C4alkylsulfinyl, phenyl-C1-C4alkylsulfonyl, S(O)n1—Ar3, phenylthio, phenylsulfinyl, phenylsulfonyl, it being possible for the phenyl-containing groups to be substituted by one or more C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C4alkoxycarbonyl, halogen, cyano, hydroxy or nitro groups;
- or R3 is O−M+, wherein M+ is an alkali metal cation or an ammonium cation;
- Q is a radical
- p1, p2 and p3 are 0 or 1;
- m1, m2 and m3 are 1, 2 or 3;
- X1, X2 and X3 are hydroxy, halogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl or C1-C6haloalkylsulfonyl;
- Z1, Z2 and Z3 are C1-C6alkyl which is substituted by the following substituents:
- C3-C4cycloalkyl or C3-C4cycloalkyl substituted by halogen, C1-C6alkyl, C1-C3alkoxy or C1-C3alkoxy-C1-C3alkyl;
- oxiranyl or oxiranyl substituted by C1-C6alkyl or C1-C3alkoxy-C1-C3alkyl;
- 3-oxetanyl or 3-oxetanyl substituted by C1-C6alkyl, C1-C3alkoxy or C1-C3alkoxy-C1-C3alkyl;
- 3-oxetanyloxy or 3-oxetanyloxy substituted by C1-C6alkyl, C1-C3alkoxy or C1-C3alkoxy-C1-C3-alkyl;
- C3-C6cycloalkyloxy or C3-C4cycloalkyloxy substituted by halogen, C1-C6alkyl, C1-C3-alkoxy or C1-C3alkoxy-C1-C3alkyl;
- C1-C6haloalkoxy;
- C1-C6alkylsulfonyloxy;
- C1-C6haloalkylsulfonyloxy;
- phenylsulfonyloxy;
- benzylsulfonyloxy, benzoyloxy;
- phenoxy;
- phenylthio;
- phenyl-sulfinyl;
- phenylsulfonyl;
- Ar10;
- OAr12;
- tri(C1-C6alkyl)silyl or tri(C1-C6alkyl)silyloxy, it being possible for the phenyl-containing groups to be mono- or poly-substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano, hydroxy or nitro;
- or Z1, Z2 and Z3 are 3-oxetanyl;
- 3-oxetanyl substituted by C1-C3alkoxy, C1-C3alkoxy-C1-C3alkyl or C1-C6alkyl;
- C3-C6cycloalkyl substituted by halogen, C1-C3alkyl or C1-C3alkoxy-C1-C3alkyl;
- tri(C1-C6alkyl)silyl;
- tri(C1-C6alkyl)silyloxy or CH═P(phenyl)3;
- or Z1, Z2 and Z3 are a C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl group, which is interrupted by oxygen, —O(CO)—, —(CO)O—, —O(CO)O—, —N(R14)O—, —ONR15—, sulfur, sulfinyl, sulfonyl, —SO2NR16—, —NR17SO2— or —NR18— and is mono- or poly-substituted by L1;
- it also being possible for L1 to be bonded at the terminal carbon atom of the C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl group;
- or Z1, Z2 and Z3 are hydrogen, hydroxy, mercapto, NO2, cyano, halogen, formyl, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkylsulfinyl, NR22R23, phenyl which may be mono- or poly-substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano, hydroxy or nitro, C3-C6cycloalkyl, C5-C6cycloalkyl substituted by C1-C3alkoxy, C1-C3alkoxy-C1-C3alkyl or C1-C6alkyl, or Ar5, O—Ar6, N(R24)Ar7 or S(O)n6Ar8;
- L1 is hydrogen, halogen, hydroxy, amino, formyl, nitro, cyano, mercapto, carbamoyl, P(O)(OC1—C6alkyl)2, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkoxycarbonyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, halo-substituted C3-C6cycloalkyl, C3-C6alkenyloxy, C3-C6alkynyloxy, C3-C6haloalkenyloxy, cyano-C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy, C1-C6alkylthio-C1-C6alkoxy, C1-C6alkylsulfinyl-C1-C6alkoxy, C1-C6-alkylsulfonyl-C1-C6alkoxy, C1-C6alkoxycarbonyl-C1-C6alkoxy, C1-C6alkylcarbonyloxy-C1-C6-alkylcarbonyl, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl or oxiranyl, which may in turn be substituted by C1-C6alkyl, C1-C3alkoxy or C1-C3alkoxy-C1-C3alkyl, or (3-oxetanyl)-oxy, which may in turn be substituted by C1-C6alkyl, C1-C3alkoxy or C1-C3alkoxy-C1-C3alkyl, or benzoyloxy, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, C1-C6alkylamino, di(C1-C6alkyl)amino, R19S(O)2O—, R20N(R21)SO2—, rhodano, phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, Ar4 or OAr11, it being possible for the phenyl-containing groups in turn to be substituted by one or more C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano, hydroxy or nitro groups;
- R4a and R5a are each independently of the other hydrogen, C1-C6alkyl, C1-C6haloalkyl, cyano, formyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, carbamoyl, C1-C6alkylaminocarbonyl, di(C1-C6alkylamino)carbonyl, di(C1-C6alkylamino)sulfonyl, C3-C6cycloalkylcarbonyl, C1-C6-alkylsulfonyl, phenylcarbonyl, phenylaminocarbonyl or phenylsulfonyl, it being possible for the phenyl groups to be mono- or poly-substituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6-alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxy or nitro;
- R4b and R5b are each independently of the other hydroxy, C1-C6alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy or benzyloxy, it being possible for the benzyl group to be mono- or poly-substituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxy or nitro;
- R9, R11, R13, R16, R17, R18, R20, R23 and R24 are each independently of the others hydrogen, C1-C6alkyl, Ar9, C1-C6haloalkyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylsulfonyl, phenyl, it being possible for the phenyl group in turn to be mono- or poly-substituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxy or nitro;
- R6a is hydrogen, C1-C6alkyl or C1-C6alkylcarbonyl;
- or together with R6b is a C2-C5alkylene chain;
- R6b, R6d, R10, R12 and R22 are each independently of the others hydrogen or C1-C6alkyl;
- R6c, R14, R15, R19 and R21, are each independently of the others C1-C6alkyl or C1-C6haloalkyl;
- Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7, Ar8, Ar9, Ar10, Ar11 and Ar12 are each independently of the others a five- to ten-membered, monocyclic or fused bicyclic ring system, which may be aromatic, partially saturated or fully saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen, sulfur, C(O) and C(═NR25), and each ring system may contain not more than two oxygen atoms, not more than two sulfur atoms, not more than two C(O) groups and not more than one C(═NR25) group, and each ring system may itself be mono- or poly-substituted by C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, amino, hydroxy, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6-haloalkenylthio, C3-C6alkynylthio, C1-C3alkoxy-C1-C3alkylthio, C1-C4alkylcarbonyl-C1-C3alkylthio, C1-C4alkoxycarbonyl-C1-C3alkylthio, cyano-C1-C3alkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, N,N-di(C1-C2alkyl)aminosulfonyl, di(C1-C4alkyl)amino, halogen, cyano, nitro or phenyl, it being possible for the phenyl group in turn to be substituted by hydroxy, C1-C6-alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C1-C3alkoxy-C1-C3alkylthio, C1-C4alkylcarbonyl-C1-C3alkylthio, C1-C4alkoxycarbonyl-C1-C3-alkylthio, cyano-C1-C3alkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, N,N-di(C1-C2alkyl)aminosulfonyl, di(C1-C4alkyl)amino, halogen, cyano or nitro, and the substituents at the nitrogen atom in the heterocyclic ring being other than halogen, and two oxygen atoms not being located next to one another;
- R25 is hydrogen, hydroxy, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl or C1-C6alkylsulfonyl;
- and
- n1 is 0, 1 or 2;
- and n6 is 0, 1 or 2;
- or an agronomically acceptable salt/isomer/enantiomer/tautomer of such a compound.
52 more elements
Dependencies are inferred from the claim text.