3-hydroxy-4-aryl-5-oxo-pyrazoline derivatives

Details 3-hydroxy-4-aryl-5-oxo-pyrazoline derivatives 3-hydroxy-4-aryl-5-oxo-pyrazoline derivatives

1998-03-31

2001-04-24

Ramsuer, Robert W. (Department: 1613)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C514S405000, C548S363100

Reexamination Certificate

active

06221810

ABSTRACT:

The invention relates to new polycyclic 3-hydroxy-4-aryl-5-oxo-pyrazoline derivatives, to a plurality of processes for their preparation, and to their use as insecticides, acaricides and herbicides.
Certain 3H-pyrazol-3-one derivatives such as, for example, 1,2-diethyl-1,2-dihydro-5-hydroxy-4-phenyl-3H-pyrazol-3-one or {[5-oxo-1,2-diphenyl-4-(p-sulphophenyl)-3-pyrazolin-3-yl]-oxy}-disodium salt or p-(3-hydroxy-5-oxo-1,2-diphenyl-3-pyrazolin-4-yl)-benzenesulphonic acid are known from the literature (cf. J. Heterocycl. Chem., 25 (5), 1301-1305, 1988 or J. Heterocycl. Chem., 25 (5), 1307-1310, 1988 or Zh. Obshch. Khim., 34 (7), 2397-2402, 1964). However, a biological action of these compounds is not described.
Furthermore, it is known that the trisodium salt of 4,4′,4″-(5-hydroxy-3-oxo-1H-pyrazole-1,2,4(3H)-triyl)-tris-benzenesulphonic acid has pharmacological properties (cf. Farmakol. Toksikol. (Moscow), 39 (2), 180-186, 1976). However, its use in plant protection is not known.
There have now been new 3-hydroxy-4-aryl-5-oxo-pyrazoline derivatives of the formula (I)
in which
A and B are identical or different and independently of one another in each case represent hydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl or optionally substituted aryl or
A and B together represent the bivalent radical of a saturated or unsaturated, optionally substituted, mono-, bi-, tri- or polycyclic system,
X represents alkyl, halogen or alkoxy,
Y represents hydrogen, alkyl, halogen, alkoxy or halogenoalkyl,
Z represents alkyl, halogen or alkoxy,
n represents a number 0, 1, 2 or 3,
G represents hydrogen (a) or the groups —CO—R
1
(b),
—SO
2
—R
3
(d),
or E (g),
in which
E represents a metal ion equivalent or an ammonium ion,
L and M represents oxygen and/or sulphur,
R
1
represents optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or cycloalkyl which can be interrupted by hetero atoms, optionally substituted phenyl, optionally substituted phenylalkyl, substituted hetaryl, substituted phenoxyalkyl or substituted hetaryloxyalkyl and
R
2
represents optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or optionally substituted phenyl or benzyl,
R
3
, R
4
and R
5
independently of one another represent optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, alkynylthio or cycloalkylthio, and optionally substituted phenyl, phenoxy or phenylthio,
R
6
and R
7
independently of one another represent hydrogen, optionally halogen-substituted alkyl, alkenyl, alkoxy or alkoxyalkyl, optionally substituted phenyl, optionally substituted benzyl,
or
R
6
and R
7
together represent an alkylene radical which is optionally interrupted by oxygen.
Taking into account various meanings (a), (b), (c), (d), (e), (f) and (g) of group G of the general formula (I), the following main structures (Ia) to (Ig) result:
where
A, B, E, L, M, X, Y, Z
n
, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
have the abovementioned meanings.
Due to one or more centres of chirality, the compounds of the formula (Ia)-(Ig) are generally obtained in the form of a mixture of stereoisomers. They can be used in the form of their mixtures of diastereoisomers or in the form of pure diastereomers or enantiomers.
Furthermore, it has been found that the new 3-hydroxy-4-aryl-5-oxo-pyrazoline derivatives of the formula (I) are obtained by one of the processes described below.
(A) 3-Hydroxy-4-aryl-5-oxo-pyrazolines of the Formula (Ia)
in which
A, B, X, Y, Z and n have the abovementioned meanings,
are obtained when
(&agr;) halogenocarbonyl ketenes of the formula (II)
in which
X, Y, Z and n have the abovementioned meaning and
Hal represents halogen, in particular chlorine or bromine,
or
(&bgr;) malonic acid derivatives of the formula (III)
in which
X, Y, Z and n have the abovementioned meaning and
R
8
represents alkyl,
are reacted with hydrazines of the formula (IV)
A—NH—NH—B  (IV)
in which
A and B have the abovementioned meaning,
if appropriate in the presence of a diluent and if appropriate in the presence of a base;
or
(B) Compounds of the Formula (Ib)
in which
A, B, X, Y, Z, R
1
and n have the abovementioned meaning,
are obtained when compounds of the formula (Ia)
in which
A, B, X, Y, Z and n have the abovementioned meaning,
&agr;) are reacted with acid halides of the general formula (V)
in which
R
1
has the abovementioned meaning and
Hal represents halogen, in particular chlorine and bromine,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent,
or
&bgr;) are reacted with carboxylic anhydrides of the general formula (VI)
R
1
—CO—O—CO—R
1
  (VI)
in which
R
1
has the abovementioned meaning,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent;
or
(C) Compounds of the Formula (Ic-1)
in which
A, B, X, Y, Z, R
2
and n have the abovementioned meaning
and
M represents oxygen or sulphur,
are obtained when compounds of the formula (Ia)
in which
A, B, X, Y, Z and n have the abovementioned meaning, are reacted with chloroformic ester or chloroformic thioester of the general formula (VII)
R
2
—M—CO—Cl  (VII)
in which
R
2
and M have the abovementioned meaning,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent;
or
(D) Compounds of the Formula (Ic-2)
in which
A, B, R
2
, X, Y, Z and n have the abovementioned meaning,
and
M represents oxygen or sulphur,
are obtained when compounds of the formula (Ia)
in which
A, B, X, Y, Z and n have the abovementioned meaning,
&agr;) are reacted with chloromonothioformic esters or chlorodithioformic esters of the general formula (VIII)
in which
M and R
2
have the abovementioned meaning,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent,
or
&bgr;) are reacted with carbon disulphide and subsequently with alkyl halides of the general formula (IX)
R
2
—Hal  (IX)
in which
R
2
has the abovementioned meaning
and
Hal represents chlorine, bromine or iodine;
or
(E) Compounds of the Formula (Id)
in which
A, B, X, Y, Z, R
3
and n have the abovementioned meaning,
are obtained when compounds of the formula (Ia)
in which
A, B, X, Y, Z and n have the abovementioned meaning,
are reacted with sulphonyl chlorides of the general formula (X)
R
3
—SO
2
—Cl  (X)
in which
R
3
has the abovementioned meaning,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent;
or
(F) The Compounds of the Formula (Ie)
in which
A, B, L, X, Y, Z, R
4
, R
5
and n have the abovementioned meaning
are obtained when
3-hydroxy-4-aryl-5-oxo-pyrazolines of the formula (Ia)
in which
A, B, X, Y, Z and n have the abovementioned meaning,
are reacted with phosphorus compounds of the general formula (XI)
in which
L, R
4
and R
5
have the abovementioned meaning
and
Hal represents halogen, in particular chlorine and bromine,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent;
or
(G) Compounds of the Formula (If)
in which
A, B, L, X, Y, Z, R
6
, R
7
and n have the abovementioned meaning
are obtained when compounds of the formula (Ia)
in which
A, B, X, Y, Z and n have the abovementioned meaning,
&agr;) are reacted with isocyanates of the general formula (XII)
R
6
—N═C═O  (XII)
in which
R
6
has the abovementioned meaning,
if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst,
or
&bgr;) are reacted with carbamoyl chlorides or thiocarbamoyl chlorides of the general formula (XIII)
in which
L, R
6
and R
7
have the abovementioned meaning,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent,
or
(H) Compounds of the Formula (Ig)
in which
A, B, X, Y, Z and n have the abovementioned meaning,
and
E represents a metal ion equivalent or an ammon

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