Substituted 3-thiocarbamoylpyrazoles

Details Substituted 3-thiocarbamoylpyrazoles Substituted 3-thiocarbamoylpyrazoles

2000-11-28

2003-02-11

Morris, Patricia L. (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S406000, C548S366100, C548S366700, C548S367400, C548S368400, C548S369100, C548S369700

Reexamination Certificate

active

06518296

ABSTRACT:

The invention relates to novel substituted 3-thiocarbamoylpyrazoles, to a plurality of processes for their preparation and to their use as pesticides.
It is already known that various substituted amino pyrazoles are highly effective against pests (cf., for example, WO 97/22 593, WO 97/44 340, EP 295 117, EP 807 668, EP 738 713, EP 352 944, EP 201 852, EP 418 016, EP 659 745, U.S. Pat. No. 5,688,966, U.S. Pat. No. 5 631 381, U.S. Pat. No. 5 629 335). However, in particular in the case of certain pests and/or at low application concentrations, the efficacy and/or persistency of the prior-art compounds is not entirely satisfactory in all areas of use.
This invention, accordingly, provides novel substituted 3-thiocarbamoylpyrazoles of the general formula (I):
in which
R
1
represents H
2
N—CS—,
m represents the number 0 or 1,
n represents the number 0, 1 or 2,
R
2
represents alkyl, alkenyl, alkinyl, cyanoalkyl, thiocyanatoalkyl, nitroalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, halogenoalkylthioalkyl, halogenoalkylsulphinylalkyl, halogenoalkylsulphonylalkyl, alkenylthioalkyl, alkenylsulphinylalkyl, alkenylsulphonylalkyl, alkinylthioalkyl, alkinylsulphinylalkyl, alkinylsulphonylalkyl, alkoxycarbonylalkyl, halogenoalkoxycarbonylalkyl, alkoxycarbonyl, alkenyloxycarbonyl, halogenoalkoxycarbonyl, alkylcarbonyl, alkoxyalkyl, halogenoalkoxyalkyl, alkoxyalkylthioalkyl, alkoxyalkylsulphinylalkyl, alkoxyalkylsulphonylalkyl, halogenoalkoxyalkylthioalkyl, halogenoalkoxyalkylsulphinylalkyl, halogenoalkoxyalkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, trialkylsilylalkyl; in each case optionally substituted cycloalkyl, cycloalkenyl or cycloalkylalkyl; and also represents aryl, heteroaryl, arylalkyl, heteroarylalkyl, aryloxyalkyl, arylthioalkyl, arylsulphinylalkyl, arylsulphonylalkyl, arylalkyloxyalkyl, arylalkylthioalkyl, arylalkylsulphinylalkyl or arylalkylsulphonylalkyl, each of which is optionally substituted in the aryl moiety or heteroaryl moiety,
R
2
for the meaning of m=0 additionally represents thiocyanato, halogen, nitro, cyano, hydroxyl, halogenoalkyl, halogenoalkenyl, chlorosulphonyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkylcarbonyloxy, formyl, trialkylsilylethinyl, optionally substituted aryloxy or represents one of the following groupings:
 —NHR
4
, —NR
4
R
5
, —NHNH
2
, —CONH
2
, —CSNH
2
, —CONR
4
R
5
, —SO
2
NR
4
R
5
, —CR
6
═NOR
7
, —CH(OH)R
8
or —CH(CN)OR
9
,
where
R
4
and R
5
independently of one another represent hydrogen, cyano, alkyl or in each case optionally substituted aryl or aralkyl,
R
6
represents hydrogen or alkyl,
R
7
represents hydrogen, alkyl or optionally substituted aralkyl,
R
8
represents alkyl or halogenoalkyl and
R
9
represents alkyl,
R
3
represents hydrogen, amino, halogen or represents one of the following groupings:
 —NH—CO—R
10
, —NHR
11
, —OR
12
, —SR
12
or —NR
13
—CX—C(R
14
, R
15
, R
16
)
where
R
10
represents alkyl, halogenoalkyl, alkoxyalkyl or in each case optionally substituted phenyl, phenoxy or pyridyl,
R
11
represents alkyl, alkenyl, alkinyl, formyl, alkylcarbonyl, halogeno-alkylcarbonyl or alkoxycarbonyl,
R
12
represents alkyl, alkenyl, alkinyl, optionally substituted aralkyl, dialkylaminoalkyl or represents the grouping —P(═Y)(OR
17
)(SR
18
),
where
R
17
and R
18
independently of one another represent alkyl and
Y represents oxygen or sulphur,
R
13
represents hydrogen, alkyl, alkoxyalkyl, propargyl, allyl, alkoxycarbonyl, alkylcarbonyl, optionally substituted benzyl or the grouping —CO—C(R
14
, R
15
, R
16
),
R
14
represents hydrogen, alkyl, halogenoalkyl, halogen or optionally substituted phenyl and
R
15
represents hydrogen, alkyl, halogenoalkyl, halogen, halalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkoxy-(alkoxy)
r
alkyl where r=0 to 4, hydroxyl, alkoxycarbonylalkyl or alkoxy, or
R
14
and R
15
together with the carbon atom to which they are attached represent a 3- to 7-membered ring system having optionally up to two heteroatoms and
R
16
represents hydroxyl, alkoxy, halalkoxy, alkoxy(alkoxy)
p
where p=1 to 4 or halalkoxy(alkoxy)
q
where q=1 to 4, and
X represents oxygen or sulphur, and
Ar represents in each case optionally substituted phenyl or pyridyl.
Furthermore, it has been found that the novel substituted 3-thiocarbamoylpyrazoles of the formula (I) are obtained when
a) 3-cyanopyrazole derivatives of the formula (II):
in which
 Ar, R
2
, R
3
, m and n are as defined above,
 are reacted with hydrogen sulphide, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent;
or when
b) 3-thiocarbamoylpyrazole derivatives of the formula (III)
in which
Ar is as defined above and
R
3−1
represents one of the groupings below:
 —NHR
11
, —OR
12
or —NR
13
—CX—C(R
14
, R
15
, R
16
),
where
R
10
to R
16
and X are as defined above,
are reacted with sulphenyl halides of formula (IV):
Hal—S—R
2
  (IV)
in which
R
2
is as defined above and
Hal represents halogen, in particular chlorine or bromine,
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary;
or when
c) the 3-thiocarbamoylpyrazole derivatives, obtainable according to process (a) or (b), of the formula (Ia):
in which
Ar, R
2
and R
3
are as defined above,
are oxidized with oxidizing agents, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst.
Finally, it has been found that the novel 3-thiocarbamoylpyrazole derivatives of the formula (I) have highly pronounced biological properties and are suitable especially for controlling animal pests, in particular insects, arachnids and nematodes, encountered in agriculture, in forests, in the protection of stored products and in the protection of materials and in the hygiene sector.
The formula (I) provides a general definition of the compounds according to the invention.
Preferred substituents or ranges of the radicals listed in the formulae mentioned above and below are illustrated below.
R
2
preferably represents (C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkinyl, cyano-(C
1
-C
4
)-alkyl, thiocyanato-(C
1
-C
4
)-alkyl, nitro-(C
1
-C
4
)-alkyl, (C
1
-C
6
)-alkylthio-(C
1
-C
4
)-alkyl, (C
1
-C
6
)-alkylsulphinyl-(C
1
-C
4
)-alkyl, (C
1
-C
6
)-alkyl-sulphonyl-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-halogenoalkylthio-(C
1
-C
4
)-alkyl having 1 to 6 halogen atoms, (C
1
-C
4
)-halogenoalkylsulphinyl-(C
1
-C
4
)-alkyl having 1 to 6 halogen atoms, (C
1
-C
4
)-halogenoalkylsulphonyl-(C
1
-C
4
)-alkyl having 1 to 6 halogen atoms, (C
2
-C
6
)-alkenylthio-(C
1
-C
4
)-alkyl, (C
2
-C
6
)-alkenylsulphinyl-(C
1
-C
4
)-alkyl, (C
2
-C
6
)-alkenylsulphonyl-(C
1
-C
4
)-alkyl, (C
2
-C
6
)-alkinylthio-(C
1
-C
4
)-alkyl, (C
2
-C
6
)-alkinylsulphinyl-(C
1
-C
4
)-alkyl, (C
2
-C
6
)-alkinylsulphonyl-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy-carbonyl-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-halogenoalkoxy-carbonyl-(C
1
-C
4
)-alkyl having 1 to 5 halogen atoms, (C
1
-C
6
)-alkoxy-carbonyl, (C
1
-C
6
)-alkyl-carbonyl, (C
1
-C
6
)-alkoxy-(C
1
-C
4
)-alkyl, (C
1
-C
6
)-halogenoalkoxy-(C
1
-C
4
)-alkyl having 1 to 6 halogen atoms, (C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkylthio-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkylsulphinyl-(C
1
-C
4
)-alkyl, alkoxy-(C
1
-C
4
)-alkylsulphonyl-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-halogenoalkoxy-(C
1
-C
4
)-alkylthio-(C
1
-C
4
)-alkyl having 1 to 5 halogen atoms, (C
1
-C
4
)-halogenoalkoxy-(C
1
-C
4
)-alkylsulphinyl-(C
1
-C
4
)-alkyl having 1 to 5 halogen atoms, (C
1
-C
4
)-halogenoalkoxy-(C
1
-C
4
)-alkylsulphonyl-(C
1
-C
4
)-alkyl having 1 to 5 halogen atoms, (C
1
-C
4
)-alkylamino-(C
1
-C
4
)-alkyl, di-(C
1
-C
4
)-alkylamino-(C
1
-C
4
)-alkyl, tri-(C
1
-C
4
)-alkylsilyl-(C
1
-C
4
)-alkyl;
 represents (C
3
-C
6
)-cycloalkyl, (C
5
-C
6
)-cycloalkenyl or (C
3
-C
6
)-cycloalkyl-(C
1
-C
2
)-alkyl, each of which is optionally mono- to pentasubstituted by identical or different substituents, possible substituents being: (C
1
-C
4
)-alkyl, (C
1

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