4-(3′,4′-heterocyclyl benzoyl) pyrazoles as...

Details 4-(3′,4′-heterocyclyl benzoyl) pyrazoles as... 4-(3′,4′-heterocyclyl benzoyl) pyrazoles as...

2001-11-01

2003-04-01

McKane, Jospeh K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S140000, C548S127000, C548S222000, C548S261000, C548S364400

Reexamination Certificate

active

06541423

ABSTRACT:

This is a 371 of International application PCT/EP00/04040 filed May 5, 2000. The present invention relates to pyrazolyl derivatives of benzo-fused unsaturated 5-membered nitrogen heterocycles, to processes for preparing such pyrazolyl derivatives, to compositions comprising such compounds, and to the use of the pyrazoyl derivatives or of the compositions comprising them for controlling harmful plants.
WO 96/05197 discloses saccharin derivatives having herbicidal action which are substituted on the benzene ring of the saccharin skeleton by a (5-hydroxypyrazol-4-yl)carbonyl radical. WO 97/30993 and WO 97/09327 disclose dioxothiochromane derivatives and dihydrobenzothiophene derivatives having herbicidal action which likewise have a (5-hydroxypyrazol-4-yl)carbonyl radical on the benzene ring of the sulfur heterocycles.
WO 97/08164 discloses, inter alia, benzo-fused derivatives of &ggr;-butyrolactam having herbicidal action which likewise have a (5-hydroxypyrazol-4-yl)carbonyl radical.
However, the herbicidal properties of the compounds known from the publications mentioned and their compatibility with crop plants do not meet all of the criteria required from herbicides.
EP-A-822 187 discloses herbicides based on aryl-substituted pyrazoles of the formula
where R
1
is hydrogen or a protective group suitable for a pesticide, R
4
is preferably hydrogen and R
2
and R
3
are phenyl, naphthyl or heterocyclic groups which are unsubstituted or substituted. R
3
is preferably a 5- or 6-membered heterocyclic ring and in particular a thiophene group. The herbicidal action of the compounds described in this publication and their crop plant compatibility are likewise not satisfactory.
It is an object of the present invention to provide novel compounds having herbicidal action which preferably have greater activity than the herbicidal substances of the prior art and/or better selectivity with respect to harmful plants.
We have found that this object is achieved by pyrazolyl derivatives of benzo-fused unsaturated 5-membered nitrogen heterocycles of the formula I defined below.
Consequently, the present invention relates to pyrazolyl derivatives of benzo-fused unsaturated 5-membered nitrogen heterocycles of the formla I,
where
X is N or a group C—R
3
;
Y is O, S, SO, SO
2
or NR
4
; or
X—Y is S═N, and X is sulfur;
R
1
is hydrogen, nitro, halogen, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-haloalkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-haloalkylsulfonyl, aminosulfonyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio-C
1
-C
6
-alkyl, C
1
-C
6
-alkylsulfinyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkylsulfonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkylamino-C
1
-C
6
-alkyl, or di(C
1
-C
6
-alkyl)amino-C
1
-C
6
-alkyl;
R
2
is hydrogen, halogen or C
1
-C
6
-alkyl;
R
3
is hydrogen, halogen, nitro, cyano, hydroxyl, amino, mercapto, thiocyanato, hydrazide, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-hydroxyalkyl, C
1
-C
6
-aminoalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-hydroxyalkoxy, C
1
-C
6
-alkoxy-C
1
-C
6
-alkoxy, C
3
-C
6
-cycloalkyl,
is C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
3
-C
6
-cycloalkylamino, where the alkyl and cycloalkyl groups of the three last-mentioned radicals may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of C
1
-C
4
-alkoxy and hydroxyl,
is C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-hydroxyalkylthio, C
1
-C
6
-alkoxy-C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl,
is phenyl, naphthyl, heterocyclyl, phenylamino, phenoxy, diphenylamino, where the phenyl and heterocyclyl groups of the six last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-haloalkoxy,
is C(O)OR
5
, or C(O)N(R
6
)R
7
;
R
4
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-hydroxyalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl,
is phenyl, naphthyl, where the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-haloalkoxy; where
R
5
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-hydroxyalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl,
is phenyl, naphthyl or heterocyclyl, where the three last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro cyano, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-haloalkoxy; and
R
6
, R
7
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-hydroxyalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl,
are phenyl or naphthyl, where the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-haloalkoxy;
and Pz is a radical of the formula IIa or IIb,
 where the variables R
8
, R
9
and R
10
are as defined below:
R
8
is hydroxyl, mercapto, halogen, OR
11
, SR
11
, SOR
12
, SO
2
R
12
, OSO
2
R
12
, P(O)R
13
R
14
, OP(O)R
13
R
14
, P(S)R
13
R
14
, OP(S)R
13
R
14
, NR
15
R
16
, ONR
15
R
16
or N-bonded heterocyclyl, which may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-haloalkoxy;
R
9
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-haloalkyl, hydroxyl, C
1
-C
6
-alkoxy or C
1
-C
6
-haloalkoxy;
R
10
is hydrogen, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, hydroxyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylthio or C
1
-C
6
-haloalkylthio;
R
11
is 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, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkylcarbonyl, C
2
-C
6
-alkenylcarbonyl, C
2
-C
6
-alkynylcarbonyl, C
3
-C
6
-cycloalkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, C
3
-C
6
-alkenyloxycarbonyl, C
3
-C
6
-alkynyloxycarbonyl, C
1
-C
6
-alkylthiocarbonyl, C
1
-C
6
-alkylaminocarbonyl, C
3
-C
6
-alkenylaminocarbonyl, C
3
-C
6
-alkynylaminocarbonyl, N,N-di(C
1
-C
6
-alkyl)aminocarbonyl, N—(C
3
-C
6
-alkenyl)—N—(C
1
-C
6
-alkyl)aminocarbonyl, N—(C
3
-C
6
-alkynyl)—N—(C
1
-C
6
-alkyl)aminocarbonyl, N—(C
1
-C
6
-alkoxy)—N—(C
1
-C
6
-alkyl)aminocarbonyl, N—(C
3
-C
6
-alkenyl)—N—(C
1
-C
6
-alkoxy)aminocarbonyl, N—(C
3
-C
6
-alkynyl)—N—(C
1
-C
6
-alkoxy)aminocarbonyl, di(C
1
-C
6
-alkyl)aminothiocarbonyl or C
1
-C
6
-alkoxyimino-C
1
-C
6
-alkyl, where the alkyl, cycloalkyl and alkoxy radicals mentioned may be partially or fully halogenated and/or may carry one, two or three of the following groups: cyano, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, di(C
1
-C
4
-alkyl)amino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkylaminocarbonyl, di(C
1
-C
4
-alkyl)aminocarbonyl, aminocarbonyl, C
1
-C
4
-alkylcarbonyloxy or C
3
-C
6
-cycloalkyl;
is phenyl, phenyl-C
1
-C
6
-alkyl, phenylcarbonyl-C
1
-C
6
-alkyl, phenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl, N—(C
1
-C
6
-alkyl)—N-(phenyl)aminocarbonyl, phenyl-C
2
-C
6
-alkenylcarbonyl, heterocyclyl, heterocyclyl-C
1
-C
6
-alkyl, heterdcyclylcarbonyl-C
1
-C
6
-alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N—(C
1
-C
6
-alkyl)—N-(heterocyclyl)aminocarbonyl, or heterocyclyl-C
2
-C
6
-alkenylcarbonyl, where t

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