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US 8,569,301 B2Granted
6, 6-dioxo-6-thia-1, 4-diaza-naphthalenes as herbicides
AssigneeSyngenta Limited
InventorsNigel James Willetts, Nicholas Phillip Mulholland, Paul Anthony Worthington, Alaric James Avery
Life of this patent
Estimating the term…
Abstract
The present invention relates to 6,6-dioxo-6-thia-1,4-diaza-naphthalene derivatives of formula (I) where R1, R2, R3a, R3b, R4 and R5 are as defined in claim 1; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for making compounds of formula (I), to herbicidal compositions comprising compounds of formula (I) and to methods of using compounds of formula (I) to control plant growth.
Claims11
A compound of formula (I)
- wherein
- R1 and R2 are independently hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, hydroxy, C1-C8alkoxy-, thiol, or C1-C8alkylthio-;
- R3a and R3b are independently hydrogen, halogen, cyano, C1-C8alkyl, C1-C8alkoxy-C1-C4alkyl-, C1-C8haloalkyl, C2-C8alkenyl, C2-C8haloalkenyl, C2-C8alkynyl, C2-C8haloalkynyl, C3-C10cycloalkyl, C3-C10cycloalkyl-C1-C4alkyl-, heterocyclyl, heterocyclyl-C1-C4alkyl-, or C1-C8alkoxycarbonyl-, or
- R3a and R3b together with the carbon atom they are attached to join to form a 3- to 10-membered carbocyclic ring or a 3- to 10-membered heterocyclic ring;
- R4 is aryl or aryl substituted by one to five R6, or heteroaryl or heteroaryl substituted by one to five R6;
- R5 is hydroxy or R8-oxy-, and where R8 is C1-C8alkyl-, C2-C8alkenyl-, C2-C8alkynyl-, aryl-C1-C4alkyl- or aryl-C1-C4alkyl- where the aryl moiety is substituted by one to five R9, C1-C8alkylcarbonyl-, C1-C8alkoxycarbonyl-, C1-C8alkylthiocarbonyl-, or C1-C8alkylsulfonyl-;
- and where each R9 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy- or C1-C8haloalkoxy-;
- each R6 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8alkoxy-C1-C4alkyl-, C1-C8haloalkyl, C1-C8haloalkoxy-C1-C4alkyl-, hydroxy, C1-C8alkoxy-, C1-C8haloalkoxy-, thiol, C1-C8alkylthio-, C1-C8haloalkylthio-, C1-C8alkylsulfinyl-, C1-C8haloalkylsulfinyl-, C1-C8alkylsulfonyl-, C1-C8haloalkylsulfonyl-, amino, N—C1-C8alkylcarbonylamino-, N—C1-C8alkyl-N—C1-C8alkylcarbonylamino-, N—C1-C8alkylsulfonylamino-, N—C1-C8alkyl-N—C1-C8alkylsulfonylamino-, aryl or aryl substituted by one to five R7, heteroaryl or heteroaryl substituted by one to five R7, aryloxy- or aryloxy- substituted by one to five R7, heteroaryloxy- or heteroaryloxy- substituted by one to five R7, arylthio- or arylthio-substituted by one to five R7, or heteroarylthio- or heteroarylthio- substituted by one to five R7;
- and
- each R7 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy- or C1-C8haloalkoxy-;
- or a salt or N-oxide thereof.
8 more elements
A compound of formula (10):
- where R1 and R2 are independently hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, hydroxy, C1-C8alkoxy-, thiol, or C1-C8alkylthio-;
- R4 is aryl or aryl substituted by one to five R6, or heteroaryl or heteroaryl substituted by one to five R6;
- each R6 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8alkoxy-C1-C4alkyl-, C1-C8haloalkyl, C1-C8haloalkoxy-C1-C4alkyl-, hydroxy, C1-C8alkoxy-, C1-C8haloalkoxy-, thiol, C1-C8alkylthio-, C1-C8haloalkylthio-, C1-C8alkylsulfinyl-, C1-C8haloalkylsulfinyl-, C1-C8alkylsulfonyl-, C1-C8haloalkylsulfonyl-, amino, N—C1-C8alkylcarbonylamino-, N—C1-C8alkyl-N—C1-C8alkylcarbonylamino-, N—C1-C8alkylsulfonylamino-, N—C1-C8alkyl-N—C1-C8alkylsulfonylamino-, aryl or aryl substituted by one to five R7, heteroaryl or heteroaryl substituted by one to five R7, aryloxy- or aryloxy- substituted by one to five R7, heteroaryloxy- or heteroaryloxy- substituted by one to five R7, arylthio- or arylthio- substituted by one to five R7, or heteroarylthio- or heteroarylthio- substituted by one to five R7;
- and
- each R7 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy- or C1-C8haloalkoxy-;
- or a salt or N-oxide thereof.
3 more elements
A compound of formula (6):
- where R1 and R2 are independently hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, hydroxy, C1-C8alkoxy-, thiol, or C1-C8alkylthio-;
- R4 is aryl or aryl substituted by one to five R6, or heteroaryl or heteroaryl substituted by one to five R6;
- each R6 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8alkoxy-C1-C4alkyl-, C1-C8haloalkyl, C1-C8haloalkoxy-C1-C4alkyl-, hydroxy, C1-C8alkoxy-, C1-C8haloalkoxy-, thiol, C1-C8alkylthio-, C1-C8haloalkylthio-, C1-C8alkylsulfinyl-, C1-C8haloalkylsulfinyl-, C1-C8alkylsulfonyl-, C1-C8haloalkylsulfonyl-, amino, N—C1-C8alkylcarbonylamino-, N—C1-C8alkyl-N—C1-C8alkylcarbonylamino-, N—C1-C8alkylsulfonylamino-, N—C1-C8alkyl-N—C1-C8alkylsulfonylamino-, aryl or aryl substituted by one to five R7, heteroaryl or heteroaryl substituted by one to five R7, aryloxy- or aryloxy- substituted by one to five R7, heteroaryloxy- or heteroaryloxy- substituted by one to five R7, arylthio- or arylthio- substituted by one to five R7, or heteroarylthio- or heteroarylthio- substituted by one to five R7;
- each R7 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy- or C1-C8haloalkoxy-;
- and
- R10 is C1-C8alkyl;
- or a salt or N-oxide thereof.
4 more elements
A compound of formula (9):
- where R1 and R2 are independently hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, hydroxy, C1-C8alkoxy-, thiol, or C1-C8alkylthio-;
- R4 is aryl or aryl substituted by one to five R6, or heteroaryl or heteroaryl substituted by one to five R6;
- each R6 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8alkoxy-C1-C4alkyl-, C1-C8haloalkyl, C1-C8haloalkoxy-C1-C4alkyl-, hydroxy, C1-C8alkoxy-, C1-C8haloalkoxy-, thiol, C1-C8alkylthio-, C1-C8haloalkylthio-, C1-C8alkylsulfinyl-, C1-C8haloalkylsulfinyl-, C1-C8alkylsulfonyl-, C1-C8haloalkylsulfonyl-, amino, N—C1-C8alkylcarbonylamino-, N—C1-C8alkyl-N—C1-C8alkylcarbonylamino-, N—C1-C8alkylsulfonylamino-, N—C1-C8alkyl-N—C1-C8alkylsulfonylamino-, aryl or aryl substituted by one to five R7, heteroaryl or heteroaryl substituted by one to five R7, aryloxy- or aryloxy- substituted by one to five R7, heteroaryloxy- or heteroaryloxy- substituted by one to five R7, arylthio- or arylthio- substituted by one to five R7, or heteroarylthio- or heteroarylthio- substituted by one to five R7;
- each R7 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy- or C1-C8haloalkoxy-;
- and
- R10 is C1-C8alkyl;
- or a salt or N-oxide thereof.
4 more elements
Dependencies are inferred from the claim text.