Production pyridazine herbicides

Details Production pyridazine herbicides Production pyridazine herbicides

1999-04-21

2001-03-20

Shah, Mukund J. (Department: 1611)

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

Organic compounds

Chalcogen in the nitrogen containing substituent

C544S105000, C548S165000, C548S170000, C548S221000, C548S259000, C548S260000, C548S261000, C549S055000, C549S466000, C560S034000

Reexamination Certificate

active

06204380

ABSTRACT:

This application is a national phase under 35 U.S.C. §371 of PCT International Application No. PCT/JP97/03727 which has an International filing date of Oct. 16, 1997 which designated the United States of America.
1. Technical Field
The present invention relates to the production of pyridazine herbicides, and more particularly, it relates to carboxylic acid ester derivatives 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.
2. 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 acid esters of formula (1):
wherein R is C
1
-C
6
alkyl, and 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 is C
1
-C
6
alkyl, and 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}carbony 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
COON(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
3
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, penta-methylene, 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)aminocarbonyloxy 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
alky (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
alkynylthio)carbonyl C
1
-C
6
alkyl, (C
3
-C
6
haloalkynylthio)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 oxazoyloxycarbonyl C
1
-C
6
alkyl, optionally substituted oxazoyl 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
alky

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