# US 8,569,301 B2 · 6, 6-dioxo-6-thia-1, 4-diaza-naphthalenes as herbicides

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- Number: US 8,569,301 B2
- Document ID: US8569301B2
- Status: Granted
- Kind: B2
- Application number: 13/320,419
- Filed: 2010-05-06
- Published: 2012-05-10
- Granted: 2013-10-29
- Earliest claimed: 2009-05-14
- Assignees: Syngenta Limited
- Applicants: Nigel James Willetts; Nicholas Phillip Mulholland; Paul Anthony Worthington; Alaric James Avery
- Inventors: Nigel James Willetts; Nicholas Phillip Mulholland; Paul Anthony Worthington; Alaric James Avery
- Web page: https://patentgrep.com/patent/US8569301B2

## CPC

- C07D 495/04: Ortho-condensed systems
- A01N 43/60: 1,4-Diazines; Hydrogenated 1,4-diazines
- C07D 241/24: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## 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.

## Claims

### Claim 1

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.

### Claim 2 (depends on 1)

A compound according to claim 1 where R1 is hydrogen, halogen or C1-C8alkyl.

### Claim 3 (depends on 1)

A compound according to claim 1 where R2 is hydrogen, halogen or C1-C8alkyl.

### Claim 4 (depends on 1)

A compound according to claim 1 where R3a is hydrogen, halogen, C1-C8alkyl, C1-C8haloalkyl or C2-C8alkynyl.

### Claim 5 (depends on 1)

A compound according to claim 1 where R3b is hydrogen, halogen, C1-C8alkyl, C1-C8haloalkyl or C2-C8alkynyl.

### Claim 6 (depends on 1)

A compound according to claim 1 where R4 is phenyl or phenyl substituted by one to five R6, or heteroaryl or heteroaryl substituted by one to five R6 (where heteroaryl is pyridyl, pyrimidinyl, pyrazolyl, triazolyl, thiophenyl, isoxazolyl, oxadiazolyl, or thiazolyl).

### Claim 7 (depends on 1)

A herbicidal composition which comprises a herbicidally effective amount of a compound according to claim 1 in addition to formulation adjuvants.

### Claim 8 (depends on 1)

A method of controlling plants which comprises applying to the plants or to the locus thereof a herbicidally effective amount of a compound according to claim 1.

### Claim 9

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.

### Claim 10

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.

### Claim 11

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.