Process for the preparation of herbicidal derivatives

Details Process for the preparation of herbicidal derivatives Process for the preparation of herbicidal derivatives

2001-11-29

2003-04-22

McKane, Joseph K. (Department: 1626)

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

C540S469000, C544S066000, C548S126000, C548S143000

Reexamination Certificate

active

06552187

ABSTRACT:

This is a 371 of international application PCT/EP00/05476 with international filing date Jun. 14, 2000.
The present invention relates to a new process for the preparation of herbicidally active substituted 3-hydroxy-4-aryl-5-oxopyrazoline derivatives.
3-Hydroxy-4-aryl-5-oxopyrazolines having herbicidal action and the preparation thereof are described, for example, in WO 92/16510, EP-A-0 508 126, WO 95/01971, WO 96/21652, WO 96/25395, WO 97/02243 and in WO 99/47525.
Surprisingly, it has now been found that substituted 3-hydroxy-4-aryl-5-oxopyrazoline derivatives can readily be prepared in a high yield and with a high degree of purity by the condensation of arylmalonic acid diamides or arylmalonic acid monoamides with hydrazine derivatives.
The present invention accordingly relates to a process for the preparation of compounds of formula I:
wherein
R
0
is, each independently of any other, halogen, C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
1
-C
6
haloalkyl, cyano-C
1
-C
6
alkyl, C
2
-C
6
haloalkenyl, cyano-C
2
-C
6
alkenyl, C
2
-C
6
haloalkynyl, cyano-C
2
-C
6
alkynyl, hydroxy, hydroxy-C
1
-C
6
alkyl, C
1
-C
6
alkoxy, nitro, amino, C
1
-C
6
alkylamino, di(C
1
-C
6
alkyl)amino, C
1
-C
6
alkylcarbonylamino, C
1
-C
6
alkylsulfonylamino, C
1
-C
6
alkylaminosulfonyl, C
1
-C
6
alkylcarbonyl, C
1
-C
6
alkylcarbonyl-C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyl-C
1
-C
6
alkyl, C
1
-C
6
alkylcarbonyl-C
2
-C
6
alkenyl, C
1
-C
6
alkoxycarbonyl-C
2
-C
6
alkenyl, C
1
-C
6
alkylcarbonyl-C
2
-C
6
alkynyl, C
1
-C
6
alkoxycarbonyl-C
2
-C
6
alkynyl, C
1
-C
6
alkoxycarbonyl, cyano, carboxyl, phenyl or an aromatic ring that contains 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the latter two aromatic rings may be substituted by C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, C
1
-C
3
alkoxy, C
1
-C
3
haloalkoxy, halogen, cyano or by nitro; or
R
0
, together with the adjacent substituents R
1
, R
2
and R
3
, forms a saturated or unsaturated C
3
-C
6
hydrocarbon bridge that may be interrupted by 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur and/or may be substituted by C
1
-C
4
alkyl;
R
1
, R
2
and R
3
are each independently of the others hydrogen, halogen, C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
6
haloalkyl, C
2
-C
6
haloalkenyl, C
1
-C
6
alkoxycarbonyl-C
2
-C
6
alkenyl, C
1
-C
6
alkylcarbonyl-C
2
-C
6
alkenyl, cyano-C
2
-C
6
alkenyl, nitro-C
2
-C
6
alkenyl, C
2
-C
6
haloalkynyl, C
1
-C
6
alkoxycarbonyl-C
2
-C
6
alkynyl, C
1
-C
6
alkylcarbonyl-C
2
-C
6
alkynyl, cyano-C
2
-C
6
alkynyl, nitro-C
2
-C
6
alkynyl, C
3
-C
6
halocycloalkyl, hydroxy-C
1
-C
6
alkyl, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, C
1
-C
6
alkylthio-C
1
-C
6
alkyl, cyano, C
1
-C
4
alkylcarbonyl, C
1
-C
6
alkoxycarbonyl, hydroxy, C
1
-C
6
alkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
alkynyloxy, C
1
-C
6
haloalkoxy, C
3
-C
6
haloalkenyloxy, C
1
-C
6
alkoxy-C
1
-C
6
alkoxy, mercapto, C
1
-C
6
alkylthio, C
1
-C
6
haloalkylthio, C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkylsulfonyl, nitro, amino, C
1
-C
6
alkylamino, di(C
1
-C
6
alkyl)amino or phenoxy in which the phenyl ring may be substituted by C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, C
1
-C
3
alkoxy, C
1
-C
3
haloalkoxy, halogen, cyano or by nitro;
R
2
also may be phenyl, naphthyl or a 5- or 6-membered aromatic ring that may contain 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by halogen, C
3
-C
8
cycloalkyl, hydroxy, mercapto, amino, cyano, nitro or by formyl; and/or
the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by C
1
-C
6
alkyl, C
1
-C
6
alkoxy, 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
alkylcarbonyl, C
1
-C
6
alkylthio, C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkylsulfonyl, mono-C
1
-C
6
alkylamino, di(C
1
-C
6
alkyl)amino, C
1
-C
6
alkylcarbonylamino, C
1
-C
6
alkylcarbonyl-(C
1
-C
6
alkyl)amino, C
2
-C
6
alkenyl, C
3
-C
6
alkenyloxy, hydroxy-C
3
-C
6
alkenyl, C
1
-C
6
alkoxy-C
2
-C
6
alkenyl, C
1
-C
6
alkoxy-C
3
-C
6
alkenyloxy, C
2
-C
6
alkenylcarbonyl, C
2
-C
6
alkenylthio, C
2
-C
6
alkenylsulfinyl, C
2
-C
6
alkenylsulfonyl, mono- or di-(C
2
-C
6
alkenyl)amino, C
1
-C
6
alkyl(C
3
-C
6
alkenyl)amino, C
2
-C
6
alkenylcarbonylamino, C
2
-C
6
alkenylcarbonyl(C
1
-C
6
alkyl)amino, C
2
-C
6
alkynyl, C
3
-C
6
alkynyloxy, hydroxy-C
3
-C
6
alkynyl, C
1
-C
6
alkoxy-C
3
-C
6
alkynyl, C
1
-C
6
alkoxy-C
4
-C
6
alkynyloxy, C
2
-C
6
alkynylcarbonyl, C
2
-C
6
alkynylthio, C
2
-C
6
alkynylsulfinyl, C
2
-C
6
alkynylsulfonyl or di-(C
3
-C
6
alkynyl)amino, C
1
-C
6
alkyl(C
3
-C
6
alkynyl)amino, C
2
-C
6
alkynylcarbonylamino or by C
2
-C
6
alkynylcarbonyl(C
1
-C
6
alkyl)amino; and/or
the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by halo-substituted C
1
-C
6
alkyl, C
1
-C
6
alkoxy, 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
alkylcarbonyl, C
1
-C
6
alkylthio, C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkylsulfonyl, mono-C
1
-C
6
alkylamino, di(C
1
-C
6
alkyl)amino, C
1
-C
6
alkylcarbonylamino, C
1
-C
6
alkylcarbonyl(C
1
-C
6
alkyl)amino, C
2
-C
6
alkenyl, C
3
-C
6
alkenyloxy, hydroxy-C
3
-C
6
alkenyl, C
1
-C
6
alkoxy-C
2
-C
6
alkenyl, C
1
-C
6
alkoxy-C
3
-C
6
alkenyloxy, C
2
-C
6
alkenylcarbonyl, C
2
-C
6
alkenylthio, C
2
-C
6
alkenylsulfinyl, C
2
-C
6
alkenylsulfonyl, mono- or di-(C
2
-C
6
alkenyl)amino, C
1
-C
6
alkyl-(C
3
-C
6
alkenyl)amino, C
2
-C
6
alkenylcarbonylamino, C
2
-C
6
alkenylcarbonyl(C
1
-C
6
alkyl)amino, C
2
-C
6
alkynyl, C
3
-C
6
alkynyloxy, hydroxy-C
3
-C
6
alkynyl, C
1
-C
6
alkoxy-C
3
-C
6
alkynyl, C
1
-C
6
alkoxy-C
4
-C
6
alkynyloxy, C
2
-C
6
alkynylcarbonyl, C
2
-C
6
alkynylthio, C
2
-C
6
alkynylsulfinyl, C
2
-C
6
alkynylsulfonyl, mono- or di-(C
3
-C
6
alkynyl)amino, C
1
-C
6
alkyl(C
3
-C
6
alkynyl)amino, C
2
-C
6
alkynylcarbonylamino or C
2
-C
6
alkynylcarbonyl(C
1
-C
6
alkyl)amino; and/or
the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by a radical of the formula COOR
50
, CONR
51
, SO
2
NR
53
R
54
or SO
2
OR
55
wherein R
50
, R
51
, R
52
, R
53
, R
54
and R
55
are each independently of the others C
1
-C
6
alkyl, C
2
-C
6
alkenyl or C
3
-C
6
alkynyl or halo-, hydroxy-, alkoxy-, mercapto-, amino-, cyano-, nitro-, alkylthio-, alkylsulfinyl- or alkylsulfonyl-substituted C
1
-C
6
alkyl, C
2
-C
6
alkenyl or C
3
-C
6
alkynyl;
n is 0, 1 or 2;
R
4
and R
5
are each independently of the other hydrogen, C
1
-C
12
alkyl, C
1
-C
12
haloalkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl, C
1
-C
10
alkoxy-C
1
-C
8
alkyl, poly-C
1
-C
10
alkoxy-C
1
-C
8
alkyl, C
1
-C
10
alkylthio-C
1
-C
8
alkyl, C
3
-C
8
cycloalkyl, C
3
-C
8
halocycloalkyl, 4- to 8-membered heterocyclyl, phenyl, &agr;- or &bgr;-naphthyl, phenyl-C
1
-C
6
alkyl, &agr;- or &bgr;-naphthyl-C
1
-C
6
alkyl, 5- or 6-membered heteroaryl or 5- or 6-membered heteroaryl-C
1
-C
6
alkyl, wherein those aromatic and heteroaromatic rings may be substituted by halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, nitro or by cyano; or
R
4
and R
5
, together with the nitrogen atoms to which they are bonded, form a saturated or unsaturated 5- to 8-membered heterocyclic ring that 1) may be interrupted by oxygen, sulfur or by —NR
14
— and/or may be substituted by halogen, C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, hydroxy, C
1
-C
6
alkoxy, C
1
-C
6
alkoxy-C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, mercapto, C
1
-C
6
alkylthio, C
3
-C
7
cycloalkyl, heteroaryl, heteroaryl-C
1
-C
6
alkyl, phenyl, phenyl-C
1
-C
6
alkyl or by benzyloxy, wherein the phenyl rings of the last three substituents may in turn be substituted by halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy or by nitro, and/or 2) may contain a fused or spiro-bound alkylene or alkenylene chain having from 2 to 6 carbon atoms that is optionally i

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