Production of pyridazine herbicides

Details Production of pyridazine herbicides Production of pyridazine herbicides

2000-07-17

2001-12-25

Berch, Mark L (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C544S239000, C544S052000, C544S105000

Reexamination Certificate

active

06333413

ABSTRACT:

TECHNICAL FIELD
The present invention relates to the production of pyridazine herbicides, and more particularly, it relates to carboxylic acids useful as intermediates for the production of pyridazin-3-one derivatives, a process for producing these intermediates, and a process for producing pyridazin-3-one derivatives from these intermediates.
BACKGROUND ART
Pyridazin-3-one derivatives of formula (7):
wherein R
2
and R
3
are independently hydrogen or C
1
-C
3
alkyl, and Q is optionally substituted phenyl, have excellent herbicidal activity, including the following examples:
The production of pyridazin-3-one derivatives in a favorable manner is preferred for the development of pyridazine herbicides with excellent activity.
DISCLOSURE OF INVENTION
The present inventors have intensively studied to find a process for producing pyridazin-3-one derivatives in a favorable manner. As a result, they have found that carboxylic acids of formula (1):
wherein R
2
, R
3
and Q are as defined above, can be easily converted into pyridazin-3-one derivatives of formula (7) and therefore serve as their important intermediates, thereby completing the present invention.
Thus, the present invention provides compounds of formula (1):
wherein R
2
, R
3
and Q are as defined above, which compounds are hereinafter referred to as the present compound(s), a process for their production, and a process for producing pyridazin-3-one derivatives of formula (7):
wherein R
2
, R
3
and Q are as defined above, comprising ring closing the compounds of formula (1).
Examples of the optionally substituted phenyl group represented by Q may include, for example, groups Q-1, Q-2, Q-3, Q-4 and Q-5 of formula (2):
wherein X is hydrogen or halogen;
Y is halogen, nitro, cyano or trifluoromethyl;
Z
1
and Z
2
are independently oxygen or sulfur;
n is 0 or 1;
R
4
is hydrogen or C
1
-C
3
alkyl;
R
5
is C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, (C
3
-C
6
cycloalkyl) C
1
-C
6
alkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, cyano C
1
-C
6
alkyl, C
1
-C
4
alkoxy C
1
-C
4
alkyl, C
1
-C
3
alkoxy C
1
-C
3
alkoxy C
1
-C
3
alkyl, carboxy C
1
-C
6
alkyl, (C
1
-C
6
alkoxy)carbonyl C
1
-C
6
alkyl, {(C
1
-C
4
alkoxy) C
1
-C
4
alkoxy}carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkoxy)carbonyl C
1
-C
6
alkyl, —CH
2
CON(R
12
)R
13
, —CH
2
COO—N(R
12
)R
13
, —CH(C
1
-C
4
alkyl)CON(R
12
)R
13
, —CH(C
1
-C
4
alkyl)COON(R
12
)R
13
, C
1
-C
4
alkylthio C
1
-C
4
alkyl or hydroxy C
1
-C
6
alkyl;
R
12
and R
13
are independently hydrogen, C
1
-C
6
alkyl, C
3
-C
8
cycloalkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, cyano C
1
-C
6
alkyl, C
1
-C
4
alkoxy C
1
-C
4
alkyl, C
1
-C
4
alkylthio C
1
-C
4
alkyl, carboxy C
1
-C
6
alkyl, (C
1
-C
6
alkoxy)carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkoxy)carbonyl C
1
-C
6
alkyl, (C
1
-C
6
alkyl)carbonyloxy C
2
-C
6
alkyl, (C
1
-C
6
alkyl)carbonylamino C
2
-C
6
alkyl, hydroxy C
2
-C
6
alkyl, optionally substituted benzyl, optionally substituted phenyl or {(C
1
-C
4
alkoxy) C
1
-C
4
alkyl}carbonyl C
1
-C
6
alkyl, or R
12
and R
13
are taken together to form trimethylene, tetramethylene, pentamethylene, ethyleneoxyethylene or ethylenethioethylene;
R
6
is C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, cyano, carboxyl, hydroxy C
1
-C
6
alkyl, C
1
-C
6
alkoxy C
1
-C
6
alkyl, C
1
-C
6
alkoxy C
1
-C
6
alkoxy C
1
-C
6
alkyl, (C
1
-C
6
alkyl)carbonyloxy C
1
-C
6
alkyl, (C
1
-C
6
haloalkyl)carbonyloxy C
1
-C
6
alkyl or (C
1
-C
6
alkoxy)carbonyl;
R
7
is hydrogen or C
1
-C
6
alkyl;
R
8
is C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, hydroxy C
1
-C
6
alkyl, C
1
-C
4
alkoxy C
1
-C
4
alkyl, C
1
-C
3
alkoxy C
1
-C
3
alkoxy C
1
-C
3
alkyl, (C
1
-C
6
alkyl)carbonyloxy C
1
-C
6
alkyl, (C
1
-C
6
haloalkyl)carbonyl C
1
-C
6
alkyl, carboxyl, carboxy C
1
-C
6
alkyl, (C
1
-C
8
alkoxy)carbonyl, (C
1
-C
6
haloalkoxy)carbonyl, (C
3
-C
10
cycloalkoxy)carbonyl, (C
3
-C
8
alkenyloxy)carbonyl, (C
3
-C
8
alkynyloxy)carbonyl, (C
1
-C
6
alkyl)aminocarbonyl, di(C
1
-C
6
alkyl)aminocarbonyl, (C
1
-C
6
alkyl)amninocarbonyloxy C
1
-C
6
alkyl or di(C
1
-C
6
alkyl)aminocarbonyloxy C
1
-C
6
alkyl;
B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, OR
1
, SR
1
, SO
2
OR
21
, COOR
22
, CR
23
═CR
24
COOR
25
or CH
2
CHWCOOR
25
;
W is hydrogen, chlorine or bromine;
R
1
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
8
cycloalkyl, benzyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, cyano C
1
-C
6
alkyl, C
1
-C
4
alkoxy C
1
-C
4
alkyl, C
1
-C
4
alkylthio C
1
-C
4
alkyl, carboxy C
1
-C
6
alkyl, (C
1
-C
8
alkoxy)carbonyl C
1
-C
6
alkyl, (C
1
-C
6
haloalkoxy)carbonyl C
1
-C
6
alkyl, {(C
1
-C
4
alkoxy) C
1
-C
4
alkoxy}carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkoxy)carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkyl) C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkyl, —CH
2
COON(R
12
)R
13
—CH—(C
1
-C
4
alkyl)COON(R
12
)R
13
, —CH
2
CON(R
12
)R
13
, —CH(C
1
-C
4
alkyl)CON(R
12
)R
13
, C
2
-C
6
alkenyloxycarbonyl C
1
-C
6
alkyl, C
3
-C
6
haloalkenyloxycarbonyl C
1
-C
6
alkyl, C
3
-C
6
alkynyloxycarbonyl C
1
-C
6
alkyl, C
3
-C
6
haloalkynyloxycarbonyl C
1
-C
6
alkyl, (C
1
-C
6
alkylthio)carbonyl C
1
-C
6
alkyl, (C
1
-C
6
haloalkylthio)carbonyl C
1
-C
6
alkyl, (C
3
-C
6
alkenylthio)carbonyl C
1
-C
6
alkyl, (C
3
-C
6
haloalkenylthio)carbonyl C
1
-C
6
alkyl, (C
3
-C
6
alkenylthio)carbonyl C
1
-C
6
alkyl, (C
3
-C
6
haloalkenylthio)carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkylthio)carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cyclohaloalkylthio)carbonyl C
1
-C
6
alkyl, ((C
3
-C
8
cycloalkyl) C
1
-C
6
alkylthio)carbonyl C
1
-C
6
alkyl, di(C
1
-C
6
alkyl)C═NO carbonyl C
1
-C
6
alkyl, (optionally substituted benzylthio)carbonyl C
1
-C
6
alkyl, (optionally substituted phenylthio)carbonyl C
1
-C
6
alkyl, hydroxy C
2
-C
6
alkoxycarbonyl C
1
-C
6
alkyl, (C
1
-C
6
alkyl)carbonyloxy C
2
-C
6
alkoxycarbonyl C
1
-C
6
alkyl, (C
1
-C
6
alkyl)carbonylamino C
2
-C
6
alkoxycarbonyl C
1
-C
6
alkyl, {(C
1
-C
6
alkoxy)carbonyl C
1
-C
6
alkyl}oxycarbonyl C
1
-C
6
alkyl, hydroxy C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyl, C
1
-C
6
haloalkoxycarbonyl, C
3
-C
8
cycloalkoxycarbonyl, C
3
-C
6
alkenyloxycarbonyl, benzyloxycarbonyl, C
1
-C
6
alkylcarbonyl, optionally substituted benzyloxycarbonyl C
1
-C
6
alkyl, optionally substituted phenoxycarbonyl C
1
-C
6
alkyl, optionally substituted furyloxycarbonyl C
1
-C
6
alkyl, optionally substituted furyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted thienyloxycarbonyl C
1
-C
6
alkyl, optionally substituted thienyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyrrolyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyrrolyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted imidazoyloxycarbonyl C
1
-C
6
alkyl, optionally substituted imidazoyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyrazoyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyrazoyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted thiazoyloxycarbonyl C
1
-C
6
alkyl, optionally substituted thiazoyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted oxazoyloxycarbonyl C
1
-C
6
alkyl, optionally substituted oxazoyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted isothiazoyloxycarbonyl C
1
-C
6
alkyl, optionally substituted isothiazoyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted isoxazoyloxycarbonyl C
1
-C
6
alkyl, optionally substituted isoxazoyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyridyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyridyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyrazinyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyrazinyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyrimidinyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyrimidinyl C
1
-C
6

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