Substituted 3-phenylpyrazoles

Details Substituted 3-phenylpyrazoles Substituted 3-phenylpyrazoles

1999-02-19

2002-04-02

Ramsuer, Robert W. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S366100

Reexamination Certificate

active

06365552

ABSTRACT:

The present invention relates to novel substituted 3-phenylpyrazoles of the formula I
in which
R
1
is hydrogen, cyano, nitro, halogen, C
1
-C
8
-alkyl, C
2
-C
8
-alkenyl, C
2
-C
8
-alkynyl, C
1
-C
8
-haloalkyl, C
2
-C
8
-haloalkenyl, C
2
-C
8
-haloalkynyl, cyano-C
1
-C
4
-alkyl, C
1
-C
8
alkyl-O—R
6
, C
1
-C
8
-alkyl- O—CO—R
6
, C
2
-C
8
-alkenyl-O—R
6
, C
2
-C
8
-alkynyl-O—R
6
, C
1
-C
8
-alkyl-S—R
6
, C
2
-C
8
-alkenyl-S—R
6
, C
2
-C
8
-alkynyl-S—R
6
, C
1
-C
8
-alkyl-SO—R
6
, C
2
-C
8
-alkenyl-SO—R
6
, C
2
-C
8
-alkynyl-SO—R
6
, C
1
-C
8
-alkyl-SO
2
—R
6
, C
2
-C
8
-alkenyl-SO
2
—R
6
; C
2
-C
8
-alkynyl-SO
2
—R
6
, —O—R
6
, —S—R
6
, —SO—R
6
, —SO
2
—R
6
, —SO
2
—Cl, —SO
2
—O—R
6
, —SO
2
—N(R
7
,R
8
), —SO
2
—N(R
7
)—CO—R
9
, —N(R
7
R
8
), —N(R
7
) —N(R
8
,R
32
), —N═N—CO—R
9
, —N(R
7
)—N(R
8
)—CO—R
9
, —N(R
10
)—CO—R
9
, —N(R
10
)—SO
2
—R
11
, —N(SO
2
—R
11
)(SO
2
—R
12
), —N(SO
2
—R
11
)(CO—R
9
), —NH—CO—O—R
6
, —O—CO—NH—R
7
, —O—CO—R
9
, —NH—CO—NH—R
13
, —O—CS—N(C
1
-C
4
-alkyl)
2
, —O—CS—NH
2
, —A—CO—O—R
6
, —A—P(O)(OR
6
)
2
, —O—(C
1
-C
4
-alkyl)-COOR
6
, —A—CO—O—N═C(R
14
,R
15
), —A—CO—O—CH
2
—O—N═C(R
16
,R
17
), —A—CO—O—C(R
18
,R
19
)—CH
2
—O—N═C(R
16
,R
17
), —A—CO—N(R
7
,R
8
), —A—CS—N(R
7
,R
8
), —A—CO—NH—SO
2
—(C
1
-C
4
-alkyl), —A—CO—R
20
, —A—CH═N—O—R
6
, —A—CH(XR
21
, YR
22
), —A—C(R
20
)═N—O—R
6
, —(C
1
-C
4
-alkyl)-O—(C
1
-C
4
-alkyl)—C(R
19
)═N—O—(C
1
-C
4
-alkyl), isoxazolidinylcarbonyl, —A—CO—N(R
7
)—C(R
8
,R
18
)—COOR
6
, —SO
2
—N(R
7
)—C(R
8
,R
18
)—COOR
6
, —SO
2
—N(R
7
)—C(R
8
,R
18
)—CO—N(R
32
,R
33
),
R
2
is cyano, trifluoromethyl or halogen;
R
3
is hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
R
4
is C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
R
5
is hydrogen, nitro, halogen, —COOR
29
or —CO—N(R
30
,R
31
);
Z is oxygen, sulfur, —SO— or —SO
2
—;
X and Y independently of one another are oxygen or sulfur;
A is a chemical bond, methylene, ethylene, 1,3-propylene, 1,4-butylene, vinylene or 1,4-butadienylene;
R
6
,R
29
independently of one another are hydrogen, C
1
-C
8
-alkyl, C
1
-C
8
-haloalkyl, C
3
-C
7
-cycloalkyl which may in turn carry from one to three C
1
-C
3
-alkyl radicals, C
3
-C
6
-alkenyl, C
5
-C
7
-cycloalkenyl which may in turn carry from one to three C
1
-C
3
-alkyl radicals, C
3
-C
6
-haloalkenyl, cyano-C
1
-C
8
-alkyl, C
3
-C
6
-alkynyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, 2-tetrahydrofuryl-C
1
-C
8
-alkyl, 3-oxetanyl, 3-thietanyl, carboxyl-C
1
-C
6
-alkyl, (C
1
-C
8
-alkoxy)carbonyl-C
1
-C
6
-alkyl, C
1
-C
4
-alkoxy-(C
1
-C
4
-alkoxy)carbonyl-C
1
-C
6
-alkyl, cyclopropylmethyl, (1-methylthiocycloprop-1-yl)methyl, C
3
-C
9
-(&agr;-alkylalkylidene)-iminooxy-C
1
-C
6
-alkyl, (C
1
-C
4
-alkyl)carbonyl, C
1
-C
4
-alkyl which is substituted by —C(R
19
)═N—O—(C
1
-C
4
-alkyl), —C(R
19
)═N—O—(C
1
-C
4
-haloalkyl), —C(R
19
)═N—O—(C
3
-C
6
-alkenyl), —C(R
19
)═N—O—(C
3
-C
6
-haloalkenyl) or —C(R
19
)═N—O—(C
1
-C
4
-alkyl)-R
34
, phenyl, phenyl-C
1
-C
6
-alkyl, phenyl-C
2
-C
6
-alkenyl, phenyl-C
3
-C
6
-alkynyl or phenoxy-C
1
-C
6
-alkyl, the phenyl ring being able in each case to be unsubstituted or in turn to carry from one to three radicals selected from the group consisting of halogen, nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkyl and C
2
-C
6
-alkenyl, 5- or 6-membered heteroaryl, heteroaryl-C
1
-C
6
-alkyl, heteroaryl-C
3
-C
6
-alkenyl, heteroaryl-C
3
-C
6
-alkynyl or heteroaryloxy-C
1
-C
6
-alkyl, the heteroaromatic radical containing in each case from one to three heteroatoms selected from a group consisting of one or two nitrogen atoms and one oxygen or sulfur atom, and the heteroaromatic radical being able, if desired, to carry on each substitutable ring member a radical selected in each case from the group consisting of hydroxyl, halogen, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio and C
1
-C
4
-alkyl;
R
7
,R
8
,R
13
,R
30
,R
31
,R
32
,R
33
independently of one another are hydrogen, C
1
-C
8
-alkyl, C
1
-C
8
-haloalkyl, C
2
-C
8
-alkenyl, C
2
-C
8
-alkynyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio-C
1
-C
4
-alkyl, cyano-C
1
-C
8
-alkyl, carboxyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, C
1
-C
4
-alkylsulfonyl-C
1
-C
4
-alkyl, C
3
-C
8
-cycloalkyl, C
1
-C
6
-alkoxy, (C
3
-C
6
-cycloalkoxy)carbonyl-C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy-(C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkyl)carbonyl, (C
1
-C
4
-haloalkyl)carbonyl, tetrahydrofuran-2-on-3-yl, phenyl, phenyl-C
1
-C
4
-alkyl, in which the phenyl ring may in each case be unsubstituted or may carry one to three radicals selected from the group consisting of halogen, nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkyl and C
2
-C
6
-alkenyl, 5- or 6-membered heteroaryl or heteroaryl-C
1
-C
4
-alkyl, the heteroaromatic radical containing from one to three heteroatoms selected from a group consisting of one or two nitrogen atoms and one oxygen or sulfur atom, and the heteroaromatic radical being able, if desired, to carry on each substitutable ring atom a radical selected from the group consisting of hydroxyl, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio and C
1
-C
4
-haloalkyl; or
R
7
and R
8
and/or R
30
and R
31
are together a tetramethylene, pentamethylene or ethyleneoxyethylene chain which may if desired carry from one to three C
1
-C
4
-alkyl radicals and/or a radical —COOR
6
;
R
9
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
3
-C
7
-cycloalkyl which may in turn carry from one to three radicals selected from the group consisting of halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-alkylthio, phenyl or phenyl-C
1
-C
6
-alkyl, in which the phenyl ring may in each case be unsubstituted or may carry from one to three radicals selected from the group consisting of halogen, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio and C
1
-C
4
-haloalkyl;
R
10
is hydrogen, C
1
-C
4
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl or the equivalent of an agriculturally usable cation;
R
11
and R
12
independently of one another are C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, phenyl which may be unsubstituted or may carry from one to three substituents in each case selected from the group consisting of halogen, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio and C
1
-C
4
-haloalkyl, or 5- or 6-membered heteroaryl containing from one to three heteroatoms selected from the group consisting of 2 nitrogen atoms and one oxygen or sulfur atom, the heteroaromatic radical being able to be unsubstituted or to carry, if desired, on each substitutable ring member a substituent in each case selected from the group consisting of hydroxyl, halogen C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-alkylthio;
R
14
is C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio, (C
1
-C
6
-alkoxy)carbonyl or (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
4
-alkyl;
R
15
is C
1
-C
6
-alkyl, trifluoromethyl, C
1
-C
6
-alkoxy-C
1
-C
4
-alkyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
4
-alkyl, di-[(C
1
-C
6
-alkoxy)carbonyl]-C
1
-C
4
-alkyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, (C
1
-C
6
-alkoxy)carbonyl, 2-furyl or phenyl, both of which may be unsubstituted or, if desired, may carry from one to three radicals selected from the group consisting of halogen, C
1
-C
4
-alkyl and C
1
-C
4
-alkoxy; consisting of halogen, C
1
-C
4
-alkyl and C
1
-C
4
-alkoxy; or
R
14
and R
15
together with the carbon atom to which they are attached, are a cyclopentane or cyclohexane ring which may if desired in turn carry from one to three C
1
-C
4
-alkyl radicals;
R
16
is hydrogen or C
1
-C
6
-alkyl;
R
17
is C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl or phenyl;
R
18
is hydrogen or C
1
-C
4
-alkyl;
R
19
is hydrogen, C
1
-C
4
-alkyl, phenyl or benzyl;
R
20
is hydrogen, cyano, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio, C
2
-C
4
-alkenyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, di-(C
1
-C

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