Pyrazol-4-ylbenzoyl derivatives and their use as herbicides

Details Pyrazol-4-ylbenzoyl derivatives and their use as herbicides Pyrazol-4-ylbenzoyl derivatives and their use as herbicides

1998-02-24

2001-09-18

Higel, Floyd D. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C504S280000, C548S252000

Reexamination Certificate

active

06291682

ABSTRACT:

The present invention relates to novel herbicidally active pyrazol-4-ylbenzoyl derivatives, to processes for the preparation of the pyrazol-4-ylbenzoyl derivatives, to compositions which comprise them, and to the use of these derivatives or of the compositions comprising them for controlling weeds.
Herbicidally active pyrazolebenzoyl derivatives have been disclosed in the literature, for example in EP 352543, WO 93/15060, WO 94/01431 and WO 93/18031.
However, the herbicidal properties of the known compounds and the compatibility with crop plants are only moderately satisfactory.
It was an object of the present invention to find novel pyrazolebenzoyl derivatives which have improved properties.
We have found that this object is achieved by pyrazol-4-ylbenzoyl derivatives of the formula I
where the substituents have the following meanings:
L,M are hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
4
-alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C
1
-C
4
-alkoxy; halogen, cyano, nitro, a group —(A)
m
—S(O)
n
R
1
or a group —(A)
m
—CO—R
2
;
Y is a group consisting of C═O, C═N—R
3
, CR
7
—NR
5
R
6
, CR
7
—OR
8
, CR
10
R
11
, CR
7
—SR
8
; 1,3-dioxanyl or 1,3-dioxolanyl, each of which is substituted by hydrogen or C
1
-C
4
-alkyl; a hetero atom selected from the group consisting of oxygen, sulfur and nitrogen;
X is a chain (—CR
12
R
13
—), (—CR
12
R
13
—CR
21
R
22
—), (—CR
12
═CR
13
—), (—CR
12
R
13
—CR
12
═CR
13
—); NR
23
;
the bond between X and Y can be saturated or unsaturated;
A is oxygen or NR
14
;
m is zero or one;
n is zero, one or two;
R
1
is C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or NR
14
;
R
2
is C
1
-C
4
alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or NR
14
;
R
3
is hydrogen, —NR
9
R
4
; C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
2
-C
6
-alkenyl, C
2
-C
6
-haloalkenyl, C
2
-C
6
-alkynyl;
mono- to polysubstituted phenyl, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro; mono- to polysubstituted benzyl, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
mono- to polysubstituted benzyloxy, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
R
4
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C═O—NR
14
;
mono- to polysubstituted phenyl, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
mono- to polysubstituted benzyl, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
R
9
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C═O—NR
14
;
mono- to polysubstituted phenyl, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
mono- to polysubstituted benzyl, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
R
5
,R
6
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
4
haloalkyl, C
2
-C
6
haloalkenyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy;
mono- to polysubstituted phenyl, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
mono- to polysubstituted benzyl, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
R
7
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkyl, C
1
-C
4
-haloalkoxy; unsubstituted or substituted phenyl, it being possible for the substituents to be from the series consisting of one to three halogens, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, nitro; R
7
and R
21
or R
7
and R
23
or R
7
and R
12
can form a bond;
R
8
is hydrogen, C
1
-C
6
alkyl, C
1
-C
4
-haloalkyl, substituted phenyl, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
substituted benzyl, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
R
10
,R
11
independently of one another are hydrogen, C
1
-C
6
-alkyl; phenyl which is unsubstituted or substituted by one to three halogens, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, nitro; R
10
and R
12
or R
10
and R
23
or R
10
and R
21
can form a bond;
R
12
,R
13
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy;
unsubstituted or substituted phenyl, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
R
14
is C
1
-C
4
-alkyl;
R
21
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy; unsubstituted or substituted phenyl, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
R
22
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy; unsubstituted or substituted phenyl, it being possible for the substituents to be from the series consisting of C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
R
23
is hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy; phenyl or benzyl, each of which is unsubstituted or substituted by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, halogen, cyano, nitro;
Q is a pyrazole ring, linked in the 4-position, of the formula II
where
R
15
is C
1
-C
4
-alkyl,
R
16
is hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl and
R
17
is hydrogen, C
1
-C
4
-alkylsulfonyl, phenylsulfonyl or alkylphenylsulfonyl,
where, in the event that Y=C═O, X is other than NR
23
,
and agriculturally useful salts of the compound I.
Compounds of the formula I are obtained by reacting 5-hydroxypyrazoles of the formula IIa with a benzoic acid derivative of the formula III and subjecting the products to a rearrangement reaction to give pyrazol-4-ylbenzoyl derivatives of the formula I:
DIAGRAM 1
In the above diagram 1, T in the abovementioned formulae has the meanings of halogen or OH and R
15
, R
16
, L, M, X, Y and n have the abovementioned meanings.
The first step of the reaction sequence, ie. the acylation, is carried out in the generally known manner, for example by adding an acid chloride of the formula III (T═Cl) or a carboxylic acids III (T═OH) which has been activated using, for example, DCC (dicyclocarbodiimides) or similar agents known from the literature, eg. triphenylphosphine/DEAD=diethyl azodicarboxylate, 2-pyridine disulfide/triphenylphosphine, to the solution or suspension of a cyclohexanedione II, in the presence or absence of an auxiliary base. The reactants and the auxiliary base are expediently employed in equimolar amounts. Under certain circumstances, a slight excess, for example, 1.2 to 1.5 mol equivalents of the auxiliary base, based on II, may be advantageous.
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