Intermediates for nematicidal pyrazoles

Details Intermediates for nematicidal pyrazoles Intermediates for nematicidal pyrazoles

2001-08-15

2003-08-12

Stockton, Laura L. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S078000

Reexamination Certificate

active

06605730

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to novel pyrazoles, to processes for their preparation and to their use as nematicides and anthelmintics as well as to the intermediates for the preparation of pyrazoles.
BACKGROUND OF THE INVENTION
Specifically, 3-(2-Thienyl)-5-phenyl-1H-pyrazole has already been disclosed in Zh. Org. Khim., 15(1), 57-63, 1979, and 3-(2-thienyl)-5-(4-methoxyphenyl)-1H-pyrazole has been described in J. Electron Spectrosc. Relat. Phenom., 31(4), 317-21, 1983.
However, it is neither described nor suggested in these publications that the aforesaid compounds have a nematicidal action.
Moreover, a certain kind of insecticidal oxazole or thiazole derivatives have already been disclosed in WO 87/06429, and insecticidal bithienyl derivatives have been ray described in WO 86/05949.
SUMMARY OF THE INVENTION
Pyrazoles of the formula (I)
wherein
R
1
represents halogen, C
1-6
alkyl, C
1-5
haloalkyl, C
2-6
alkoxy, C
1-4
alkylthio, C
2-5
alkenyloxy, C
3-5
alkenyloxy, C
2-6
(total carbon number) alkoxyalkyl, C
2-6
(total carbon number) alkylthioalkyl, C
1-5
haloalkoxy, C
2-6
(total carbon number) alkoxyalkoxy, hydroxy or optionally substituted phenyl,
R
2
represents hydrogen, halogen, C
1-5
alkyl, C
2-6
(total carbon number) alkoxy-alkyl, C
2-6
(total carbon number) alkylthioalkyl, C
2-6
(total carbon number) alkylsulfinylalkyl, C
2-6
(total carbon number) alkylsulfonylalkyl or C
1-5
halo-alkyl,
R
3
represents hydrogen, C
1-5
alkyl, —COR
4
, —COOR
5
, CH(OR
6
)
2
, or CH
2
Si(R
7
)
3
,
R
4
represents C
1-10
alkyl, C
1-6
haloalkyl, C
2-6
alkenyl, optionally substituted C
3-6
cycloalkyl, C
2-6
(total carbon number) alkoxyalkyl, C
2-6
(total carbon number) alkylthioalkyl, optionally substituted phenyl, C
1-5
alkylamino, di-(C
1-6
alkyl)amino or optionally substituted phenylamino,
R
5
represents C
1-7
alkyl,
R
6
and R
7
represent C
1-6
alkyl, and
n is 1, 2 or 3, and when n is 2 or 3, The R
1
radicals may be the same or different.
DETAILED DESCRIPTION
There have now been found novel pyrazoles of the formula (I)
wherein
R
1
represents halogen, C
1-6
alkyl, C
1-5
haloalkyl, C
2-6
alkoxy, C
1-4
alkylthio, C
2-5
alkenyloxy, C
3-5
alkynyloxy, C
2-6
(total carbon number) alkoxyalkyl, C
2-6
(total carbon number) alkylthioalkyl, C
1-5
haloalkoxy, C
2-6
(total carbon number) alkoxyalkoxy, hydroxy or optionally substituted phenyl,
R
2
represents hydrogen, halogen, C
1-5
alkyl, C
2-6
(total carbon number) alkoxy-alkyl, C
2-6
(total carbon number) alkylthioalkyl, C
2-6
(total carbon number) alkylsulfinylalkyl, C
2-6
(total carbon number) alkylsulfonylalkyl or C
1-5
halo-alkyl,
R
3
represents hydrogen, C
1-5
alkyl, —COR
4
, —COOR
5
, CH(OR
6
)
2
, or CH
2
Si(R
7
)
3
,
R
4
represents C
1-10
alkyl, C
1-6
haloalkyl, C
2-6
alkenyl, optionally substituted C
3-6
cycloalkyl, C
2-6
(total carbon number) alkoxyalkyl, C
2-6
(total carbon number) alkylthioalkyl, optionally substituted phenyl, C
1-5
alkylamino, di-(C
1-6
alkyl)amino or optionally substituted phenylamino,
R
5
represents C
1-7
alkyl,
R
6
and R
7
represent C
1-6
alkyl, and
n is 1, 2 or 3, and when n is 2 or 3,
the corresponding number (n) of R
1
radicals may be the same or different.
(i) When R
3
is not H, the compound of the above formula (I) can exist as a mixture of the following positional isomers
wherein R
1
, R
2
, R
3
and n are as defined above, and
wherein R
1
, R
2
, R
3
and n are as defined above.
(ii) When R
3
is H, the compound of the above formula (I) can exist as a mixture of the following tautomers:
wherein R
1
, R
2
and n are as defined above, and
wherein R
1
, R
2
and n are as defined above.
The compounds of formula (I) can be obtained by a process in which
a) when R
3
is hydrogen:
compounds of the formula
 wherein R
1
and n are as defined above,
are reacted with a compound of the formula
NH
2
—NH
2
  (III)
 in the presence of suitable diluent, and if appropriate, in the presence of an acid catalyst, or
b) when R
3
is hydrogen
compounds of the formula
 wherein R
1
, R
2
and n are as defined above,
are reacted with the aforementioned compound of the formula (III) in the presence of
suitable diluent, and if appropriate, in the presence of an acid catalyst, or
c) when R
3
is a radical as defined above but other than hydrogen:
compounds of formula
 wherein R
1
, R
2
and n are as defined above,
are reacted with compounds of the formula
R
3
—X  (VI)
 wherein R
3
is a radical as defined above but other than hydrogen, and X is halogen, in the presence of suitable diluent, and if appropriate, in the presence of an acid binding agent, or
d) compounds of the formulae
 wherein R
1
, R
2
, R
3
and n are as defined above are oxidized, or
e) when R
2
is alkylsulfinylalkyl or alkylsulfonylalkyl:
compounds of the formula
 wherein R
1
, R
3
and n are as defined above, p is 1, 2 or 3, q is 1, 2, 3, 4 or 5, and 2≦p+q≦6, are oxidized.
The compounds of formula (I) according to the present invention have strong nematicidal activities and anthelmintic activities. In particular, they exhibit a very excellent nematicidal and anthelmintic effects as compared with the aforesaid well-known 3-(2-thienyl)-5-phenyl-1H-pyrazole and 3-(2-thienyl)-5-(4- methoxyphenyl)-1H-pyrazole, and also have a good affinity for crops and mammals. Accordingly, the compounds of the present invention are very useful as nematicides and anthelmintics.
In this specification, the “halogen” and the halogen in the “haloalkyl” and the “haloalkoxy” means fluoro, chloro, bromo or iodo.
The “alkyl” may be straight-chain or branched, and includes, for example, methyl, ethyl, propyl, isopropyl, n-, iso-, sec- or tert-butyl, n-, iso-, neo- or tert-pentyl, n- or isohexyl, heptyl, octyl, nonyl and decyl.
The “haloalkyl” may be straight-chain or branched, and includes, for example, chloromethyl, 2-chloroethyl, trifluoromethyl, 2,2,2-trifluoroethyl and 2 2,3,3-tetrafluoropropyl.
The “alkoxy” may be straight-chain or branched, and includes, for example, ethoxy, propoxy, isopropoxy, n-, iso-, sec- or tert-butoxy, pentyloxy and hexyloxy.
The “alkylthio” may be straight-chain or branched, and includes, for example, methylthio, ethylthio, propylthio, isopropylthio, and n-, iso-, sec- or tert-butylthio.
The “alkenyloxy” includes, for example, vinyloxy, allyloxy, 1-propenyloxy, iso-propenyloxy, and 1-, 2- or 3-butenyloxy.
The “alkynyloxy” includes, for example, propargyloxy. The “alkoxyalkyl” includes, for example, methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-, iso-, sec- or tert-butoxymethyl, and n-, iso-, sec-, tert- or neo-pentoxymethyl.
The “alkylthioalkyl” includes, for example, methylthiomethyl, ethylthiomethyl, propylthiomethyl, isopropylthiomethyl, n-, iso-, sec- or tert-butylthiomethyl, n-, iso-, sec-, tert- or neo-pentylthiomethyl, and methylthioethyl.
The “haloalkoxy” includes, for example, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, 2,2,2-trifluoroethoxy and 2,2,3,3-tetrafluoropropyloxy.
The “alkoxyalkoxy” includes, for example, methoxymethoxy and ethoxymethoxy.
The “alkylsulfinylalkyl” includes, for example, methylsulfinylmethyl, ethylsulfinylmethyl, propylsulfinylmethyl, isopropylsulfinylmethyl and methylsulfinylethyl.
The “alkylsulfonylalkyl” includes, for example, methylsulfonylmethyl, ethylsulfonylmethyl, propylsulfonylmethyl, isopropylsulfonylmethyl and methylsulfonylethyl.
The “cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
The “fluoro-substituted cyclopropyl” includes, for example, 2,2-difluorocyclopropyl.
The “optionally substituted phenyl” includes, for example, phenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 4-chlorophenyl, 4-trifluoromethoxyphenyl, (4-fluorophenyl)-phenyl, and (4-trifluoromethylphenyl)phenyl.
The “alkylamino” includes, for example, methylamino, ethylamino, propylamino, isopropylamino, n-, iso-, sec- or tert-butylamino, and n-, iso-, sec-, tert- or neo-pentylamino.
The “dialkylamino” includes, for example,

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