Substituted 1-arylpyrazoles, pesticidal compositions and use

Substituted 1-arylpyrazoles useful in combating insects having the arachnida and nematodes of the formula ##STR1## in which R.sup.1 represents hydrogen or alkyl, PA1 R.sup.2 represents alkyl or halogenoalkyl, PA1 R.sup.3 represents hydrogen or alkanoyl, PA1 R.sup.4 represents hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, halogenoalkyl, alkenyl, halogenoalkenyl or alkinyl, in each case optionally substituted cycloalkyl, aralkyl or aryl, or, when X represents oxygen or sulphur, R.sup.4 can represent a cation equivalent which is bonded in a salt-like manner, PA1 A represents a double-linked alkylene radical, PA1 X represents oxygen, sulphur or a radical ##STR2## Ar represents optionally substituted phenyl, pyridyl and n represents a number 0, 1 or 2, where R.sup.5 represents hydrogen, alkyl, hydroxylalkyl, alkoxyalkyl, alylthioalkyl, halogenoalkyl, alkenyl, halogenoalkenyl or alkinyl, or represents optionally substituted cycloalkyl, aralkyl or aryl.

The invention relates to new substituted 1-arylpyrazoles, to several 
processes for their preparation, and to their use as pesticides. 
It is known that certain substituted 1-arylpyrazoles, such as, for example, 
the compound 
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylthiopyrazole or 
the compound 
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl-3-methyl-4-dichlorofluorom 
ethylthiopyrazole or the compound 
1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-dichlorofluoromethylsu 
lphonyl -5-propionamidopyrazole or the compound 
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-dichloro-fluor 
omethylsulphinyl-pyrazole or the compound 
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulphiny 
l-pyrazole, have a good activity against pests (cf., for example, EP-A 
201,852). 
However, the level of activity or duration of activity of these previously 
known compounds is not entirely satisfactory in all fields of application, 
in particular in the case of certain insects or when low application 
concentrations are used. 
New substituted 1-arylpyrazoles of the general formula (I) 
##STR3## 
in which 
R.sup.1 represents hydrogen or alkyl, 
R.sup.2 represents alkyl or halogenoalkyl, 
R.sup.3 represents hydrogen or alkanoyl, 
R.sup.4 represents hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, 
alkylthioalkyl, halogenoalkyl, alkenyl, halogenoalkenyl or alkinyl, or 
represents in each case optionally substituted cycloalkyl, aralkyl or 
aryl, or, in the event that X represents oxygen or sulphur, also 
represents a cation equivalent which is bonded in a salt-like manner, 
A represents a double-linked alkylene radical, 
X represents oxygen, sulphur or a radical 
##STR4## 
Ar represents optionally substituted phenyl or optionally substituted 
pyridyl and 
n represents a number 0, 1 or 2, where R.sup.5 represents hydrogen, alkyl, 
hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, halogenoalkyl, alkenyl, 
halogenoalkenyl or alkinyl, or represents optionally substituted 
cycloalkyl, aralkyl or aryl, 
have now been found. 
Furthermore, it has been found that the new substituted 1-arylpyrazoles of 
the general formula (I) 
##STR5## 
in which 
R.sup.1 represents hydrogen or alkyl, 
R.sup.2 represents alkyl or halogenoalkyl, 
R.sup.3 represents hydrogen or alkanoyl, 
R.sup.4 represents hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, 
alkylthioalkyl, halogenoalkyl, alkenyl, halogenoalkenyl or alkinyl, or 
represents in each case optionally substituted cycloalkyl, aralkyl or 
aryl, or, in the event that X represents oxygen or sulphur, also 
represents a cation equivalent which is bonded in a salt-like manner, 
A represents a double-linked alkylene radical, 
X represents oxygen, sulphur or a radical 
##STR6## 
Ar represents optionally substituted phenyl or optionally substituted 
pyridyl and 
n represents a number 0, 1 or 2, where R.sup.5 represents hydrogen, alkyl, 
hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, halogenoalkyl, alkenyl, 
halogenoalkenyl or alkinyl, or represents optionally substituted 
cycloalkyl, aralkyl or aryl, 
are obtained by one of the processes described below: 
(a) substituted 1-arylpyrazoles of the formula (I) 
##STR7## 
in which 
R.sup.1, R.sup.2, R.sup.3, R.sup.4, A, X, Ar and n have the abovementioned 
meaning, 
are obtained when 1-arylpyrazoles of the formula (II) 
##STR8## 
in which 
R.sup.1, R.sup.2, R.sup.3, Ar and n have the abovementioned meaning, are 
reacted with alkylating agents of the formula (III) 
##STR9## 
in which 
Hal.sup.1 represents halogen and 
R.sup.4, A and X have the abovementioned meaning, if appropriate in the 
presence of a diluent and if appropriate in the presence of a reaction 
auxiliary; 
(b) substituted 1-arylpyrazoles of the formula (Ib) 
##STR10## 
in which 
R.sup.1, R.sup.2, A, Ar and n have the abovementioned meaning, are obtained 
when substituted 1-arylpyrazoles of the formula (Ia) 
##STR11## 
in which 
R.sup.4-1 represents alkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, 
halogenoalkyl, alkenyl, halogenoalkenyl or alkinyl, or represents in each 
case optionally substituted cycloalkyl, aralkyl or aryl and 
R.sup.1, R.sup.2, R.sup.3, A, X, Ar and n have the abovementioned meaning, 
are hydrolyzed with acids or bases as a catalyst in the presence of water 
and, if appropriate, in the presence of a diluent; 
(c) substituted 1-arylpyrazoles of the formula (Ic) 
##STR12## 
in which 
R.sup.4-2 represents hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, 
alkylthioalkyl, halogenoalkyl, alkenyl, halogenoalkenyl or alkinyl, or 
represents in each case optionally substituted cycloalkyl, aralkyl or aryl 
and 
R.sup.1, R.sup.2, A, X, Ar and n have the abovementioned meaning, 
are obtained when substituted 1-arylpyrazoles of the formula (Ib) 
##STR13## 
in which 
R.sup.1, R.sup.2, A and n have the abovementioned meaning, are reacted with 
alcohols, thiols or amino compounds of the formula (IV) 
EQU R.sup.4-2 --X--H (IV) 
in which 
R.sup.4-2 and X have the abovementioned meaning, in the presence of an 
acylation catalyst and, if appropriate, in the presence of a diluent and, 
if appropriate, in the presence of a reaction auxiliary; 
(d) substituted 1-arylpyrazoles of the formula (Id) 
##STR14## 
in which 
R.sup.1, R.sup.2, R.sup.3, R.sup.4, A, X and Ar have the abovementioned 
meaning, 
are obtained when 1-arylpyrazoles which are unsubstituted in the 
4-position, of the formula (V), 
##STR15## 
in which 
R.sup.1, R.sup.3, R.sup.4, A, X and Ar have the abovementioned meaning, 
are reacted with sulphenyl halides of the formula (VI) 
EQU R.sup.2 --S--Hal.sup.2 (VI) 
in which 
Hal.sup.2 represents halogen and 
R.sup.2 has the abovementioned meaning, if appropriate in the presence of a 
diluent and, if appropriate, in the presence of a reaction auxiliary; 
(e) substituted 1-arylpyrazoles of the formula (Ie) 
##STR16## 
in which 
R.sup.1, R.sup.2, R.sup.3, R.sup.4, A, X and Ar have the abovementioned 
meaning and 
m represents a number 1 or 2, 
are obtained when substituted 1-arylpyrazoles of the formula (Id) 
##STR17## 
in which 
R.sup.1, R.sup.2, R.sup.3, R.sup.4, A, X and Ar have the abovementioned 
meaning, 
are reacted with oxidants, if appropriate in the presence of a diluent and, 
if appropriate, in the presence of a catalyst; 
(f) substituted 1-arylpyrazoles of the formula (If) 
##STR18## 
in which 
X.sup.1 represents oxygen or sulphur, 
M.sup..sym. represents a cation which is bonded in a saltlike manner and 
R.sup.1, R.sup.2, R.sup.3, A, Ar and n have the abovementioned meaning, 
are obtained when substituted 1-arylpyrazoles of the formula (Ig) 
##STR19## 
in which 
R.sup.1, R.sup.2, R.sup.3, A, X.sup.1, Ar and n have the abovementioned 
meaning, 
are reacted with inorganic or organic bases, if appropriate in the presence 
of a diluent. 
Finally, it has been found that the new substituted 1-arylpyrazoles of the 
general formula (I) have a good activity against pests, in particular 
against leaf insects and soil insects which damage plants. 
Surprisingly, the substituted 1-arylpyrazoles of the general formula (I) 
according to the invention have a considerably better activity against 
pests than the substituted 1-arylpyrazoles which are known from the prior 
art, such as, for example, the compound 
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylthiopyrazole or 
the compound 
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-dichlorofluoro 
methylthiopyrazole or the compound 
1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-dichlorofluoromethylsu 
lphonyl -5-propionamidopyrazole or the compound 
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-dichlorofluoro 
methylsulphinyl-pyrazole or the compound 
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulphiny 
l-pyrazole, which are compounds of a similar chemical structure and similar 
type of action. 
Formula (I) provides a general definition of the substituted 
1-arylpyrazoles according to the invention. Preferred compounds of the 
formula (I) are those in which 
R.sup.1 represents hydrogen or straight-chain or branched alkyl having 1 to 
6 carbon atoms, 
R.sup.2 represents straight-chain or branched alkyl having 1 to 6 carbon 
atoms or straight-chain or branched halogenoalkyl having 1 to 4 carbon 
atoms and 1 to 9 identical or different halogen atoms, 
R.sup.3 represents hydrogen or straight-chain or branched alkanoyl having 1 
to 5 carbon atoms, 
R.sup.4 represents hydrogen, in each case straight-chain or branched alkyl 
or hydroxyalkyl, each of which has 1 to 12 carbon atoms, in each case 
straight-chain or branched alkoxyalkyl or alkylthioalkyl, each of which 
has 2 to 12 carbon atoms, in each case straight-chain or branched alkenyl 
or alkinyl, each of which has 2 to 12 carbon atoms, straight-chain or 
branched halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or 
different halogen atoms, straight-chain or branched halogenoalkenyl having 
2 to 8 carbon atoms and 1 to 15 identical or different halogen atoms, 
cycloalkyl which has 3 to 7 carbon atoms and which is optionally 
monosubstituted or polysubstituted by identical or different alkyl 
substituents which have 1 to 4 carbon atoms and which are straight-chain 
or branched, or represents phenyl, benzyl or phenylethyl, each of which is 
optionally monosubstituted or polysubstituted in the phenyl moiety by 
identical or different substituents, suitable phenyl substituents in each 
case being: halogen, cyano, nitro, in each case straight-chain or branched 
alkyl, alkoxy or alkylthio, each of which has 1 to 4 carbon atoms, in each 
case straight-chain or branched halogenoalkyl, halogenoalkoxy or 
halogenoalkylthio, each of which has 1 to 4 carbon atoms and 1 to 9 
identical or different halogen atoms, in each case straight-chain or 
branched alkoxycarbonyl or alkoximinoalkyl, each of which has 1 to 4 
carbon atoms in the individual alkyl moieties, and also phenyl which is 
optionally monosubstituted or polysubstituted by identical or different 
substituents from the series comprising halogen and/or straight-chain or 
branched alkyl having 1 to 4 carbon atoms; and, furthermore, in the event 
that X represents oxygen or sulphur, also represents one equivalent of an 
alkali metal, alkaline earth metal, copper, zinc, manganese, tin, 
iron-cobalt or nickel cation or an ammonium, phosphonium or sulphonium 
cation, each of which is optionally monosubstituted or polysubstituted by 
identical or different substituents, suitable substituents being: 
straight-chain or branched alkyl having 1 to 18 carbon atoms, phenyl or 
benzyl, 
A represents a double-linked, straight-chain or branched alkylene radical 
having 1 to 12 carbon atoms, 
X represents oxygen, sulphur or a radical 
##STR20## 
Ar represents phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, each of which is 
optionally monosubstituted or polysubstituted by identical or different 
substituents, suitable substituents in each case being: cyano, nitro, 
halogen, in each case straight-chain or branched alkyl, alkoxy or 
alkoxycarbonyl, each of which has 1 to 4 carbon atoms, in each case 
straight-chain or branched halogenoalkyl or halogenoalkoxy, each of which 
has 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, 
or a radical --S(O).sub.p --R.sup.6 and 
n represents a number 0, 1 or 2, where R.sup.5 represents hydrogen, in each 
case straight-chain or branched alkyl or hydroxyalkyl, each of which has 1 
to 12 carbon atoms, in each case straight-chain or branched alkoxyalkyl or 
alkylthioalkyl, each of which has 2 to 12 carbon atoms, in each case 
straight-chain or branched alkenyl or alkinyl, each of which has 2 to 12 
carbon atoms, in each case straight-chain or branched halogenoalkyl having 
1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, 
straight-chain or branched halogenoalkenyl having 2 to 8 carbon atoms and 
1 to 15 identical or different halogen atoms, or cycloalkyl which has 3 to 
7 carbon atoms and which is optionally monosubstituted or polysubstituted 
by identical or different alkyl substituents which are straight-chain or 
branched and which have 1 to 4 carbon atoms, or represents phenyl, benzyl 
or phenylethyl, each of which is optionally monosubstituted or 
polysubstituted in the phenyl moiety by identical or different 
substituents, suitable phenyl substituents in each case being: halogen, 
cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or 
alkylthio, each of which has 1 to 4 carbon atoms, in each case 
straight-chain or branched halogenoalkyl, halogenoalkoxy or 
halogenoalkylthio, each of which has 1 to 4 carbon atoms and 1 to 9 
identical or different halogen atoms, in each case straight-chain or 
branched alkoxycarbonyl or alkoximinoalkyl, each of which has 1 to 4 
carbon atoms in the individual alkyl moieties, and also phenyl which is 
optionally monosubstituted or polysubstituted by identical or different 
substituents from the series comprising halogen and/or straight-chain or 
branched alkyl having 1 to 4 carbon atoms; 
R.sup.6 represents amino and in each case optionally straight-chain or 
branched alkyl, alkylamino, dialkylamino or halogenoalkyl, in each case 
having to 4 carbon atoms in the individual alkyl moieties and, in the case 
of the halogenoalkyl, 1 to 9 identical or different halogen atoms, and 
p represents a number 0, 1 or 2. 
Particularly preferred compounds of the formula (I) are those in which 
R.sup.1 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or 
t-butyl, 
R.sup.2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 
chloromethyl, difluoromethyl, difluorochloromethyl, fluorodichloromethyl, 
trifluoromethyl, pentafluoroethyl, pentachloroethyl, 
fluorotetrachloroethyl, difluorotrichloroethyl, trifluorodichloroethyl, 
tetrafluorochloroethyl, heptafluoropropyl, chloroethyl, bromoethyl, 
chloropropyl or bromopropyl, 
R.sup.3 represents hydrogen, acetyl, propionyl or butyryl, 
R.sup.4 represents hydrogen, or methyl, ethyl, n- or i-propyl, n-, i-, s- 
or t-butyl or n- or i-pentyl, each of which is optionally monosubstituted 
to trisubstituted by identical or different substituents from the series 
comprising fluorine, chlorine, hydroxyl, methoxy, ethoxy, methylthio or 
ethylthio, or allyl, propenyl or butenyl, each of which is optionally 
monosubstituted to trisubstituted by identical or different substituents 
from the series comprising fluorine and chlorine, or propargyl, propinyl, 
butinyl or pentinyl, or cyclopropyl, cyclopentyl or cyclohexyl, or benzyl 
or phenyl, each of which is optionally monosubstituted to pentasubstituted 
by identical or different substituents from the series comprising 
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, ethoxy, 
methylthio or trifluoromethyl, and, in the event that X represents oxygen 
or sulphur, furthermore also represents one equivalent of a sodium, 
potassium, magnesium, calcium, barium, copper, zinc, manganese, tin, iron, 
cobalt or nickel cation, or an ammonium, phosphonium or sulphonium cation, 
each of which is optionally monosubstituted to tetrasubstituted by 
identical or different substituents from the series comprising methyl, 
ethyl, n- or i-propyl, n-, i-, s- or t-butyl, benzyl or phenyl, 
A represents a double-linked, straight-chain or branched alkylene radical 
having 1 to 6 carbon atoms, 
X represents oxygen, sulphur or a radical 
##STR21## 
Ar represents phenyl which is optionally monosubstituted to 
pentasubstituted by identical or different substituents, or 2-pyridyl 
which is optionally monosubstituted to tetrasubstituted by identical or 
different substituents, suitable substituents in each case being: cyano, 
nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- and 
i-propyl, n-, i-, s- and t-butyl, methoxy, ethoxy, methoxycarbonyl, 
ethoxycarbonyl, trifluoromethyl, trichloromethyl, dichlorofluoromethyl, 
difluorochloromethyl, chloromethyl, dichloromethyl, difluoromethyl, 
pentafluoroethyl, tetrafluoroethyl, trifluorochloroethyl, trifluoroethyl, 
difluorodichloroethyl, trifluorodichloroethyl, pentachloroethyl, 
trifluoromethoxy, trichloromethoxy, dichlorofluoromethoxy, 
difluorochloromethoxy, chloromethoxy, dichloromethoxy, difluoromethoxy, 
pentafluoroethoxy, tetrafluoroethoxy, trifluorochloroethoxy, 
trifluoroethoxy, difluorodichloroethoxy, trifluorodichloroethoxy, 
pentachloroethoxy or a radical --S(O).sub.p --R.sup.6 and 
n represents a number 0, 1 or 2, where 
R.sup.5 represents hydrogen, or methyl, ethyl, n- or i-propyl, n-, i-, s- 
or t-butyl or n- or i-pentyl, each of which is optionally monosubstituted 
to trisubstituted by identical or different substituents from the series 
comprising fluorine, chlorine, hydroxyl, methoxy, ethoxy, methylthio or 
ethylthio, or allyl, propenyl or butenyl, each of which is optionally 
monosubstituted to trisubstituted by identical or different substituents 
from the series comprising fluorine and chlorine, or propargyl, propinyl, 
butinyl or pentinyl, or cyclopropyl, cyclopentyl or cyclohexyl, or 
represents benzyl or phenyl, each of which is optionally monosubstituted 
to pentasubstituted by identical or different substituents from the series 
comprising fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, 
methoxy, ethoxy, methylthio or trifluoromethyl, 
R.sup.6 represents amino, methylamino, ethylamino, dimethylamino, 
diethylamino, fluorodichloromethyl, difluoromethyl, tetrafluoroethyl, 
trifluorochloroethyl, trichloromethyl, trichloroethyl, trifluoromethyl, 
methyl or ethyl, and 
p represents a number 0, 1 or 2. 
Very particularly preferred compounds of the formula (I) are those in which 
R.sup.1 represents hydrogen or methyl, 
R.sup.2 represents methyl, ethyl, n- or i-propyl, trifluoromethyl, 
dichlorofluoromethyl or chlorodifluoromethyl, 
R.sup.3 represents hydrogen, acetyl or propionyl, 
R.sup.4 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- 
or i-pentyl, allyl, propenyl, n- or i-butenyl, n- or i-pentenyl, 
propargyl, propinyl, n- or i-butinyl, n- or i-pentinyl, trifluoroethyl, 
trichloroethyl, chloroethyl, chloropropenyl, dichloropropenyl, 
hydroxyethyl, hydroxypropyl, methoxymethyl, methoxyethyl, methoxypropyl, 
ethoxymethyl, ethoxyethyl, ethoxypropyl, propoxymethyl, propoxyethyl, 
butoxymethyl, butoxyethyl, methylthiomethyl, methylthioethyl, 
methylthiopropyl, ethylthioethyl, ethylthiopropyl or propylthioethyl, and, 
in the event that X represents oxygen or sulphur, furthermore also 
represents a sodium or potassium ion or represents an ammonium ion which 
is optionally monosubstituted to tetrasubstituted by identical or 
different substituents from the series comprising methyl, ethyl, n- or 
i-propyl, n-butyl or benzyl, 
A represents a double-linked, straight-chain or branched alkylene radical 
having 1 to 4 carbon atoms, 
X represents oxygen, sulphur or 
##STR22## 
Ar represents phenyl which is optionally monosubstituted to 
pentasubstituted by identical or different substituents, suitable 
substituents being: fluorine, chlorine, bromine, methyl, ethyl, methoxy, 
ethoxy, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, 
trifluoromethylsulphinyl or trifluoromethylsulphonyl and 
n represents a number 0, 1 or 2, where 
R.sup.5 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or 
t-butyl, n- or i-pentyl, allyl, propenyl, n- or i-butenyl, n- or 
i-pentenyl, propargyl, propinyl, n- or i-butinyl, n- or i-pentinyl, 
trifluoroethyl, trichloroethyl, chloroethyl, chloropropenyl, 
dichloropropenyl, hydroxyethyl, hydroxypropyl, methoxymethyl, 
methoxyethyl, methoxypropyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, 
methylthiomethyl, methylthioethyl, methylthiopropyl, ethylthioethyl or 
ethylthiopropyl. 
Besides, other compounds of the formula (I) which are very particularly 
preferred are those in which 
R.sup.1 represents hydrogen or methyl, 
R.sup.2 represents methyl, ethyl, n- or i-propyl, trifluoromethyl, 
dichlorofluoromethyl or chlorodifluoromethyl, 
R.sup.3 represents hydrogen, 
R.sup.4 represents hydrogen or one equivalent of a sodium, potassium, 
calcium, magnesium, barium, copper, zinc, manganese, tin, iron, cobalt or 
nickel cation, or an ammonium cation which is optionally monosubstituted 
to tetrasubstituted by identical or different substituents from the series 
comprising methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, benzyl or 
phenyl, 
A represents a double-linked, straight-chain or branched alkylene radical 
having 1 to 4 carbon atoms, 
X represents oxygen, 
Ar represents phenyl which is optionally monosubstituted to 
pentasubstituted by identical or different substituents, suitable 
substituents being: fluorine, chlorine, bromine, methyl, ethyl, methoxy, 
ethoxy, trifluoromethyl, trifluoromethylsulphinyl or 
trifluoromethylsulphonyl and 
n represents a number 0, 1 or 2. 
Especially preferred compounds of the formula (I) are those in which 
R.sup.1 represents hydrogen or methyl, 
R.sup.2 represents trifluoromethyl, dichlorofluoromethyl or 
chlorodifluoromethyl, 
R.sup.3 represents hydrogen, acetyl or propionyl, 
R.sup.4 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or 
t-butyl or benzyl, 
A represents a radical of the formula --CH.sub.2 --; --CH.sub.2 --CH.sub.2 
--; --CH.sub.2 --CH.sub.2 --CH.sub.2 -- or 
##STR23## 
X represents oxygen or a radical 
##STR24## 
Ar represents phenyl which is optionally monosubstituted to 
pentasubstituted by identical or different substituents from the series 
comprising fluorine, chlorine, bromine, trifluoromethyl or 
trifluoromethoxy and 
n represents a number 0, 1 or 2, where 
R.sup.5 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or 
a radical --SO.sub.2 --R.sup.6 and 
R.sup.6 represents methyl, trifluoromethyl, phenyl or p-tolyl. 
If, for example, 
5-acetamido-3-methyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluorom 
ethylthiopyrazole and methyl bromoacetate are used as the starting 
substances, the course of the reaction of process (a) according to the 
invention may be represented by the following equation: 
##STR25## 
If, for example, 
5-[N-methoxycarbonylmethyl)acetamido]-3-methyl-1-(2,6-dichloro-4-trifluoro 
methylphenyl)-4-trifluoromethylthio-pyrazole is used as the starting 
compound, the course of the reaction of process (b) according to the 
invention may be represented by the following equation: 
##STR26## 
If, for example, 
N-[4-methylthio-1-(2,4,6-trichlorophenyl)-5-pyrazolyl]-glycine and 
2-methoxyethanol are used as the starting substances, the course of the 
reaction of process (c) according to the invention may be represented by 
the following equation: 
##STR27## 
If, for example, 
N-[1-(2,6-dichloro-4-trifluoromethylphenyl)-5-pyrazolyl]-glycine and 
dichlorofluoromethanesulphenyl chloride are used as the starting 
substances, the course of the reaction of process (d) according to the 
invention may be represented by the following equation: 
##STR28## 
If, for example, 
3-methyl-4-methyl-thio)-1-(2,4-dichlorophenyl)-5-ethoxycarbonyl-methylamin 
opyrazole is used as the starting compound and 3-chloroperbenzoic acid as 
the oxidant, the course of the reaction of process (e) according to the 
invention may be represented by the following equation: 
##STR29## 
If, for example, 
N-[1-(2,6-dichloro-4-trifluoromethylsulphonyl-phenyl)-3-methyl-4-trifluoro 
methylsulphonyl -5-pyrazolyl]-glycine and triethylamine are used as the 
starting substances, the course of the reaction of process (f) according 
to the invention may be represented by the following equation: 
##STR30## 
Formula (II) provides a general definition of the 1-arylpyrazoles required 
as starting substances for carrying out process (a) according to the 
invention. In this formula (II), R.sup.1, R.sup.2, R.sup.3, Ar and n 
preferably represent those radicals and indices which have already been 
mentioned in connection with the description of the substances of the 
formula (I) according to the invention as being preferred for these 
substituents and indices. 
The 1-arylpyrazoles of the formula (II) are known (cf., for example, EP-A 
201,852). 
Formula (III) provides a general definition of the alkylating agents 
furthermore required as starting substances for carrying out process (a) 
according to the invention. In this formula (III), R.sup.4, A and X 
preferably represent those radicals which have already been mentioned in 
connection with the description of the substances of the formula (I) 
according to the invention as being preferred for these substituents. 
Hal.sup.1 preferably represents chlorine, bromine or iodine, in particular 
bromine. 
The alkylating agents of the formula (III) are generally known compounds of 
organic chemistry, or they can be obtained in analogy to generally known 
processes. 
Formula (Ia) provides a general definition of the substituted 
1-arylpyrazoles required as starting substances for carrying out process 
(b) according to the invention. In this formula (Ia), R.sup.1, R.sup.2, 
R.sup.3, A, X, Ar and n preferably represent those radicals which have 
already been mentioned in connection with the description of the 
substances of the formula (I) according to the invention as being 
preferred for this substituent. 
R.sup.4-1 preferably represents those radicals which have already been 
mentioned in connection with the description of the substances of the 
formula (I) according to the invention as being preferred for the 
substituent R.sup.4, with the exception of the hydrogen radical and the 
cations which are bonded in a salt-like manner. 
The substituted 1-arylpyrazoles of the formula (Ia) are compounds according 
to the invention and can be obtained with the aid of processes (a), (c), 
(d) or (e) according to the invention. 
Formula (Ib) provides a general definition of the substituted 
1-arylpyrazoles required as starting substances for carrying out process 
(c) according to the invention. In this formula (Ib), R.sup.1, R.sup.2, A, 
Ar and n preferably represent those radicals which have already been 
mentioned in connection with the description of the substances of the 
formula (I) according to the invention as being preferred for these 
substituents. 
The substituted 1-arylpyrazoles of the formula (Ib) are compounds according 
to the invention and can be obtained with the aid of processes (a), (b), 
(d) or (e) according to the invention. 
Formula (IV) provides a general definition of the alcohols, thiols or amino 
compounds furthermore required as starting substances for carrying out 
process (c) according to the invention. In this formula (IV), X preferably 
represents those radicals which have already been mentioned in connection 
with the description of the substances of the formula (I) according to the 
invention as being preferred for these substituents. 
R.sup.4-2 preferably represents those radical which have already been 
mentioned in connection with the description of the substances of the 
formula (I) according to the invention as being preferred for the 
substituent R.sup.4, with the exception of the cations which are bonded in 
a salt-like manner. 
The alcohols, thiols or amino compounds of the formula (IV) are generally 
known compounds of organic chemistry. 
Formula (V) provides a general definition of the 1-arylpyrazoles which are 
unsubstituted in the 4-position and which are required as starting 
substances for carrying out process (d) according to the invention. In 
this formula (V), R.sup.1, R.sup.3, R.sup.4, A, X and Ar preferably 
represent those radicals which have already been mentioned in connection 
with the description of the substances of the formula (I) according to the 
invention as being preferred for these substituents. 
The 1-arylpyrazoles which are unsubstituted in the 4-position, of the 
formula (V), were hitherto unknown. However, they are obtained in analogy 
to known processes, for example when 1-arylpyrazoles of the formula (VII) 
##STR31## 
in which 
R.sup.1, R.sup.3 and Ar have the abovementioned meaning, are reacted, in 
analogy to the procedure of process (a) according to the invention, with 
alkylating agents of the formula (III) 
##STR32## 
in which 
A, X and R.sup.4 have the abovementioned meaning and 
Hal.sup.1 represents halogen, in particular bromine, if appropriate in the 
presence of a diluent, such as, for example, acetonitrile or 
tetrahydrofuran, and, if appropriate, in the presence of a reaction 
auxiliary such as, for example, potassium carbonate or sodium hydride, at 
temperatures between -30.degree. C. and +120.degree. C., or, 
alternatively, when 1-arylpyrazoles of the formula (VIII) 
##STR33## 
in which 
R.sup.1, A and Ar have the abovementioned meaning and 
Hal.sup.3 represents halogen, in particular chlorine or bromine, 
in a first step, initially subjected to an intramolecular cyclization 
reaction with a base, such as, for example, ammonia, if appropriate in the 
presence of a diluent, such as, for example, ethanol, and then, in a 
second step, the resulting N-pyrazolyl lactams of the formula (IX) 
##STR34## 
in which 
R.sup.1, A and Ar have the abovementioned meaning, are then cleaved again 
with aqueous acids, such as, for example, hydrobromic acid, at 
temperatures between 20.degree. C. and 150.degree. C., to give the 
1-arylpyrazoles which are unsubstituted in the 4-position, of the formula 
(Va), 
##STR35## 
in which 
R.sup.1, A and Ar have the abovementioned meaning (cf. also the Preparation 
Examples). 
1-Arylpyrazoles of the formulae (VII) and (VIII) are known (cf., for 
example, EP-A 154,115 and EP-A 201,852). 
Formula (VI)) provides a general definition of the sulphenyl halides 
furthermore required as starting substances for carrying out process (d) 
according to the invention. In this formula (IV)), R.sup.2 preferably 
represents those radicals which have already been mentioned in connection 
with the description of the substances of the formula (I) according to the 
invention as being preferred for this substituent. 
Hal.sup.2 preferably represents chlorine or bromine. 
The sulphenyl halides of the formula (VI) are generally known compounds of 
organic chemistry. 
Formula (Id) provides a general definition of the substituted 
1-arylpyrazoles required as starting substances for carrying out process 
(e) according to the invention. In this formula (Id), R.sup.1, R.sup.2, 
R.sup.3, R.sup.4, A, X and Ar preferably represent those radicals which 
have already been mentioned in connection with the description of the 
substances of the formula (I) according to the invention as being 
preferred for these substituents. 
The substituted 1-arylpyrazoles of the formula (Id) are compounds according 
to the invention and can be obtained with the aid of processes (a), (b), 
(c), (d) and (f) according to the invention. 
Formula (Ig) provides a general definition of the substituted 
1-arylpyrazoles required as starting substances for carrying out process 
(f) according to the invention. In this formula (Ig), R.sup.1, R.sup.2, 
R.sup.3, A, Ar and n preferably represent those radicals and indices which 
have already been mentioned in connection with the description of the 
substances of the formula (I) according to the invention as being 
preferred for these substituents and indices. 
X.sup.1 represents oxygen, sulphur or a radical of the formula 
##STR36## 
where R.sup.6 preferably represents those radicals which have already been 
mentioned in connection with the description of the substances of the 
formula (I) according to the invention as being preferred for this 
substituent. 
The substituted 1-arylpyrazoles of the formula (Ig) are compounds according 
to the invention and can be obtained with the aid of processes (a), (b), 
(d) and (e) according to the invention. 
Diluents which are suitable for carrying out process (a) according to the 
invention are inert organic solvents. These in particular include 
aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, 
such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, 
petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or 
carbon tetrachloride, ethers, such as diethyl ether, dioxane, 
tetrahydrofuran, ethylene glycol dimethyl ether or ethylene glycol diethyl 
ether, ketones, such as acetone or butanone, nitriles, such as 
acetonitrile or propionitrile, amides, such as dimethylformamide, 
dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or 
hexamethylphosphoric triamide, esters, such as ethyl acetate, or 
sulphoxides, such as dimethyl sulphoxide. 
If appropriate, process (a) according to the invention can also be carried 
out in a two-phase system, such as, for example, water/toluene or 
water/dichloromethane, if appropriate in the presence of a phase transfer 
catalyst. Examples of such catalysts which may be mentioned are: 
tetrabutylammonium iodide, tetrabutylammonium bromide, 
tributyl-methylphosphonium bromide, trimethyl-C.sub.13 /C.sub.15 
-alkylammonium chloride, dibenzyl-dimethylammonium methylsulphate, 
dimethyl-C.sub.12 /C.sub.14 -alkylbenzylammonium chloride, 
tetrabutylammonium hydroxide, 15-crown-5, 18-crown-6, 
triethylbenzylammonium chloride or trimethylbenzylammonium chloride. 
Reaction auxiliaries which are suitable for carrying out process (a) 
according to the invention are all inorganic and organic bases which can 
customarily be used. Hydrides, hydroxides, amides, alkoxides, carbonates 
or hydrogen carbonates of alkali metals, such as, for example, sodium 
hydride, sodium amide, sodium methoxide, sodium hydroxide, sodium 
carbonate or sodium hydrogen carbonate, and also tertiary amines, such as, 
for example, triethylamine, N,N-dimethylaniline, pyridine, 
4-(N,N-dimethylamino)pyridine, diazabicyclooctane (DABCO), 
diazabicyclononene (DBN) or diazabicycloundecene (DBU), are preferably 
used. 
When carrying out process (a) according to the invention, the reaction 
temperatures can be varied within a substantial range. In general, the 
process is carried out between -20.degree. C. and +150.degree. C., 
preferably between 0.degree. C. and +100.degree. C. 
For carrying out process (a) according to the invention, 1.0 to 20.0 moles, 
preferably 1.0 to 15.0 moles, of alkylating agent of the formula (III) 
and, if appropriate, 1.0 to 3.0 moles, preferably 1.0 to 2.0 moles, of 
reaction auxiliary and, if appropriate, 0.01 to 1.0 mole of phase transfer 
catalyst are generally employed per mole of 1-arylpyrazole of the formula 
(II). The reaction is carried out and the reaction products of the formula 
(I) are worked up and isolated in a generally customary fashion. 
Diluents which are suitable for carrying out process (b) according to the 
invention are inorganic or organic polar solvents. Alcohols, such as, for 
example, methanol, ethanol or propanol, or their mixtures with water, are 
preferably used. 
Catalysts which are preferably suitable for carrying out process (b) 
according to the invention are acids, in particular hydrochloric acid or 
sulphuric acid, or bases, in particular sodium hydroxide, sodium hydride 
or potassium t-butoxide. 
When carrying out process (b) according to the invention, the reaction 
temperatures can be varied within a substantial range. In general, the 
process is carried out between +20.degree. C. and +150.degree. C., 
preferably between +50.degree. C. an 120.degree. C. 
For carrying out process (b) according to the invention, 1.0 to 20.0 moles, 
preferably 1.0 to 10.0 moles, of catalyst acid or catalyst base are 
generally employed per mole of substituted 1-arylpyrazole of the formula 
(Ia), and the mixture is heated for several hours to the reaction 
temperature required. The reaction products of the formula (Ib) are worked 
up, isolated and purified by customary methods. 
Diluents which are suitable for carrying out process (c) according to the 
invention are inert organic solvents. 
These preferably include aliphatic or aromatic, optionally halogenated 
hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, 
chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, 
chloroform or carbon tetrachloride, ethers, such as diethyl ether, 
dioxane, tetrahydrofuran, ethylene glycol dimethyl ether or ethylene 
glycol diethyl ether, ketones, such as acetone or butanone, nitriles, such 
as acetonitrile or propionitrile, amides, such as dimethylformamide, 
dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or 
hexamethylphosphoric triamide, esters, such as ethyl acetate, or 
sulphoxides, such as dimethyl sulphoxide. 
If alcohols, amino compounds or thiols in liquid form are used as the 
reactants of the formula (IV), it is also possible to employ these in an 
appropriate excess, to act simultaneously as the diluent. 
Process (c) according to the invention is preferably carried out in the 
presence of a suitable acylation catalyst. In principle, suitable 
acylation catalysts are all customary reaction auxiliaries which can be 
used for esterification and amidations. The following may be mentioned by 
way of example: acid halide formers, such as thionyl chloride, phosphorus 
trichloride, phosphorus pentachloride or phosphorus oxychloride, or 
activated ester components, such as N-hydroxy-succinimide, anhydride 
formers, such as 4-nitrophenyl chloroformate, or customary condensation 
agents, such as concentrated sulphuric acid, dicyclohexylcarbodiimide 
(DCC), triphenylphosphine as a mixture with carbon tetrachloride, 
N,N'-carbonyl-diimidazole or N-ethoxycarbonyl-2-ethoxy-dihydroquinoline 
(EEDQ). 
Moreover, process (c) according to the invention can be carried out, if 
appropriate, in the presence of a suitable reaction auxiliary. Reaction 
auxiliaries which are suitable are all customary inorganic or organic 
bases. These include, for example, alkali metal hydroxides, such as sodium 
hydroxdide or potassium hydroxide, alkali metal carbonates, such as sodium 
carbonate, potassium carbonate or sodium hydrogen carbonate, and also 
tertiary amines, such as triethylamine, N,N-dimethylaniline, pyridine, 
N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene 
(DBN) or diazabicycloundecene (DBU). A suitable excess of one of the 
amines used simultaneously as the reactant of the formula (IV) can also 
serve as reaction auxiliary, if appropriate. 
When carrying out process (c) according to the invention, the reaction 
temperatures can be varied within a substantial range. In general, the 
process is carried out at temperatures between -20.degree. C. and 
+150.degree. C., preferably at temperatures between 0.degree. C. and 
+100.degree. C. 
For carrying out process (c) according to the invention, 1.0 to 20.0 moles, 
preferably 1.0 to 10.0 moles, of alcohol, amino compound or thiol of the 
formula (IV), 1.0 to 5.0 moles, preferably 1.0 to 2.0 moles, of acylation 
catalyst and, if appropriate, 1.0 to 2.0 moles of reaction auxiliary are 
generally employed per mole of substituted 1-arylpyrazole of the formula 
(Ib). 
In most cases, it is advantageous to first prepare an activated complex 
(acid halide, activated ester, mixed acid anhydride etc.) from the 
substituted 1-arylpyrazole of the formula (Ib) and the acylation catalyst, 
and, if appropriate, this activated complex can be isolated and reacted 
with the alcohol, amine or thiol of the formula (IV) either in a separate 
reaction step or in a one-pot process. Depending on the nature of the 
acylation catalyst used, addition of the reaction auxiliary can be useful 
either in step 1 for the formation of the activated complex or in step 2 
for the reaction of the latter. The reaction is carried out and the 
reaction products of the formula (Ic) are worked up and isolated by 
generally customary processes. 
Diluents which are suitable for carrying out process (d) according to the 
invention are inert organic solvents. These in particular include 
aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, 
such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, 
petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or 
carbon tetrachloride, ethers, such as diethyl ether, dioxane, 
tetrahydrofuran, ethylene glycol dimethyl ether or ethylene glycol diethyl 
ether, ketones, such as acetone or butanone, nitriles, such as 
acetonitrile or propionitrile, amides, such as dimethylformamide, 
dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or 
hexamethylphosphoric triamide, esters, such as ethyl acetate, sulphoxides, 
such as dimethyl sulphoxide, or acids, such as, for example, acetic acid. 
If appropriate, process (d) according to the invention can be carried out 
in the presence of a reaction auxiliary. Reaction auxiliaries which are 
suitable are all customary inorganic or organic bases. These include, for 
example, alkali metal hydroxides, such as sodium hydroxdide or potassium 
hydroxide, alkali metal carbonates, such as sodium carbonate, potassium 
carbonate or sodium hydrogen carbonate, and also tertiary amines, such as 
triethylamine, N,N-dimethylaniline, pyridine, N,N-dimethylaminopyridine, 
diazabicyclooctane (DABCO), diazabicyclononene (DBN) or 
diazabicycloundecene (DBU). 
When carrying out process (d) according to the invention, the reaction 
temperatures can be varied within a substantial range. In general, the 
process is carried out at temperatures between -20.degree. C. and 
+120.degree. C., preferably at temperatures between 0.degree. C. and 
+50.degree. C. 
For carrying out process (d) according to the invention, 1.0 to 2.5 moles, 
preferably 1.0 to 1.5 moles, of sulphenyl halide of the formula (VI) and, 
if appropriate, 1.0 to 2.5 moles, preferably 1.0 to 1.5 moles, of reaction 
auxiliary are generally employed per mole of 1-arylpyrazole which is 
unsubstituted in the 4-position, of the formula (V). The reaction is 
carried out and the reaction products of the formula (Id) are worked up 
and isolated by generally customary methods. 
Oxidants which are suitable for carrying out process (e) according to the 
invention are all customary oxidants which can be used for the oxidation 
of sulphur. The following oxidants are particularly suitable: hydrogen 
peroxide, organic peracids, such as, for example, peracetic acid, 
m-chloroperbenzoic acid or p-nitroperbenzoic acid, or atmospheric oxygen. 
Diluents which are suitable for carrying out process (e) according to the 
invention are also inert organic solvents. The following are preferably 
used: hydrocarbons, such as benzine, benzene, toluene, hexane or petroleum 
ether; chlorinated hydrocarbons, such as dichloromethane, 
1,2-dichloroethane, chloroform, carbon tetrachloride or chlorobenzene; 
ethers, such as diethyl ether, dioxane or tetrahydrofuran; carboxylic 
acids, such as acetic acid or propionic acid, or dipolar aprotic solvents, 
such as acetonitrile, acetone, ethyl acetate or dimethylformamide. 
If appropriate, process (e) according to the invention can be carried out 
in the presence of an acidbinding agent. Suitable acid-binding agents are 
all organic and inorganic acid-binding agents which can customarily be 
used. The following are preferably used: hydroxides, acetates or 
carbonates of alkaline earth metals or alkali metals, such as, for 
example, calcium hydroxide, sodium hydroxide, sodium acetate or sodium 
carbonate. 
If appropriate, process (e) according to the invention can be carried out 
in the presence of a suitable catalyst. Catalysts which are suitable are 
all metal salt catalysts which are customarily used for sulphur oxidations 
of this type. Ammonium molybdate may be mentioned in this connection by 
way of example. 
When carrying out process (e) according to the invention, the reaction 
temperatures can be varied within a substantial range. In general, the 
process is carried out at temperatures between -20.degree. C. and 
+70.degree. C., preferably at temperatures between 0.degree. C. and 
+50.degree. C. 
For carrying out process (f) according to the invention, 0.8 to 1.2 moles, 
preferably equimolar amounts, of oxidant are generally employed per mole 
of substituted 1-arylpyrazole of the formula (Id) if it is desired to 
interrupt the oxidation of sulphur at the sulphoxide level. For oxidation 
to give the sulphone, 1.8 to 3.0 moles, preferably twice the molar 
amounts, of oxidant are generally employed per mole of substituted 
1-arylpyrazole of the formula (Id). The reaction is carried out and the 
end products of the formula (Ie) are worked up and isolated by customary 
processes. 
Process (f) according to the invention is carried out in the presence of an 
inorganic or organic base. Bases which are used are hydroxides, oxides or 
carbonates of alkali metals or alkaline earth metals or suitably 
substituted amines, depending on the nature of the desired counterion 
M.sup..sym. in the compounds of the formula (If). 
Diluents which are suitable for carrying out process (f) according to the 
invention are organic or aqueous solvents or organic-aqueous solvent 
mixtures. Alcohols, such as methanol, ethanol or propanol, or their 
mixtures with water, as well as pure water, are preferably used as 
diluents. 
When carrying out process (f) according to the invention, the reaction 
temperatures can be varied within a substantial range. In general, the 
process is carried out at temperatures between -20.degree. C. and 
+120.degree. C., preferably at temperatures between 0.degree. C. and 
80.degree. C. 
For carrying out process (f) according to the invention, 1.0 to 20.0 moles, 
preferably 1.0 to 10.0 moles, of base are generally employed per mole of 
substituted 1-arylpyrazole of the formula (Ig). The calcium, barium, 
magnesium, manganese, copper, nickel, tin, iron and cobalt salts are also 
obtained from the sodium salts by treating them with a corresponding 
inorganic metal salt, for example calcium chloride, barium chloride, 
copper sulphate, nickel chloride or cobalt nitrate. The salts of the 
formula (If) are worked up and isolated by customary methods. 
The active compounds of the general formula (I) are suitable for combating 
animal pests, in particular insects, arachnida and nematodes, encountered 
in agriculture, in forestry, in the protection of stored products and of 
materials, and in the hygiene field, and have good plant tolerance and 
favourable toxicity to warm-blooded animals. They are active against 
normally sensitive and resistant species and against all or some stages of 
development. The abovementioned pests include: 
From the order of the Isopoda, for example, Oniscus asellus, Armadillidium 
vulgare and Porcellio scaber. From the order of the Diplopoda, for 
example, Blaniulus guttulatus. From the order of the Chilopoda, for 
example, Geophilus carpophagus and Scutigera spec. From the order of the 
Symphyla, for example, Scutigerella immaculata. From the order of the 
Thysanura, for example, Lepisma saccharina. From the order of the 
Collembola, for example, Onychiurus armatus. From the order of the 
Orthoptera, for example, Blatta orientalis, Periplaneta americana, 
Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa 
spp., Locusta migratoria migratorioides, Melanoplus differentialis and 
Schistocerca gregaria. From the order of the Dermaptera, for example, 
Forficula auricularia. From the order of the Isoptera, for example, 
Reticulitermes spp. From the order of the Anoplura, for example, 
Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, 
Haematopinus spp. and Linognathus spp. From the order of the Malophaga, 
for example, Trichodectes spp. and Damalinea spp. From the order of the 
Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci. From 
the order of the Heteroptera, for example, Eurygaster spp., Dysdercus 
intermedius, Piesma quadrate, Cimex lectularius, Rhodnius prolixus and 
Triatoma spp. From the order of the Homoptera, for example, Aleurodes 
brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossyoii, 
Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, 
Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., 
Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, 
Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax 
striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, 
Pseudococcus spp. and Psylla spp. From the order of the Lepidoptera, for 
example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, 
Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, 
Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrix 
thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia 
spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra 
brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia 
ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, 
Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea 
pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua 
reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima 
and Tortrix viridana. From the order of the Coleoptera, for example, 
Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, 
Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, 
Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., 
Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., 
Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus 
sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera 
postica, Dermestes spp., Trogoderma ssp., Anthrenus spp., Attagenus spp., 
Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium 
psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus 
spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra 
zealandica. From the order of the Hymenoptera, for example, Diprion spp., 
Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa ssp. From the 
order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., 
Drosophila melanogaster, Musca spp., Fannia spp., Calliphora 
erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., 
Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma 
spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia 
spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula 
paludosa. From the order of the Siphonaptera, for example, Xenopsylla 
cheopis and Ceratophyllus spp. From the order of the Arachnida, for 
example, Scorpio maurus and Latrodectus mactans. 
From the order of the Acarina, for example, Acarus siro, Argas spp., 
Ornithodoros spp., Dermanyssus gallinae, Eriophves ribis, Phyllocoptruta 
oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma 
spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., 
Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp. 
The active compounds according to the invention are not only active against 
plant, hygiene and stored product pests, but also, in the veterinary 
medicine sector, against animal parasites (ectoparasites and 
endoparasites), such as scaly ticks, argasidae, scab mites, trombidae, 
flies (stinging and sucking), parasitic fly larvae, lice, hair lice, bird 
lice, fleas and endoparasitically living worms. 
They are active against normally sensitive and resistant species and 
strains, as well as against all parasitic and non-parasitic stages of 
development of the ecto- and endoparasites. 
The active compounds according to the invention have a strong insecticidal 
action. They can be employed particularly successfully against insects 
which are harmful to plants, such as, for example, against the caterpillar 
of the owlet moth (Spodoptera frugiperda) and the larvae of the mustard 
beetle (Phaedon cochleariae) or against the green peach aphid (Mycus 
persicae), and for the control of soil insects, such as, for example, 
against the grubs of the onion fly (Phorbia anticua) or of Diabrotica 
balteata larvae in the soil. In this connection, the active compounds 
according to the invention also show systemic properties and are therefore 
particularly suitable as seed treatment agents. 
The active compounds according to the invention can additionally be 
employed with particularly good success for combating pests which live as 
parasites on warm-blooded animals, such as, for example, against cattle 
ticks (Boophilus microplus). 
The active compounds can be converted to the customary formulations, such 
as solutions, emulsions, suspensions, powders, foams, pastes, granules, 
aerosols, natural and synthetic materials impregnated with active 
compound, very fine capsules in polymeric substances and in coating 
compositions for seed, and formulations used with burning equipment, such 
as fumigating cartridges, fumigating cans, fumigating coils and the like, 
as well as ULV cold mist and warm mist formulations. 
These formulations are produced in a known manner, for example by mixing 
the active compounds with extenders, that is, liquid solvents, liquefied 
gases under pressure and/or solid carriers, optionally with the use of 
surface-active agents, that is emulsifying agents and/or dispersing agents 
and/or foam-forming agents. In the case of the use of water as an 
extender, organic solvents can, for example, also be used as auxiliary 
solvents. As liquid solvents, there are suitable in the main: aromatics, 
such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or 
chlorinated aliphatic hydrocarbons, such as chlorobenzenes, 
chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as 
cyclohexane or paraffins, for example mineral oil fractions, alcohols, 
such as butanol or glycol as well as their ethers and esters, ketones, 
such as acetone, methyl ethyl ketone, methyl isobutyl ketone or 
cyclohexanone, strongly polar solvents, such as dimethylformamide and 
dimethyl sulphoxide, as well as water; by liquefied gaseous extenders or 
carriers are meant liquids which are gaseous at ambient temperature and 
under atmospheric pressure, for example aerosol propellants, such as 
halogenated hydrocarbons as well as butane, propane, nitrogen and carbon 
dioxide; as solid carriers there are suitable: for example ground natural 
minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, 
montmorillonite or diatomaceous earth, and ground synthetic minerals, such 
as highly disperse silica, alumina and silicates; as solid carriers for 
granules there are suitable: for example crushed and fractionated natural 
rocks, such as calcite, marble, pumice, sepiolite and dolomite, as well as 
synthetic granules of inorganic and organic meals, and granules of organic 
material such as sawdust, coconut shells, maize cobs and tobacco stalks; 
as emulsifying and/or foam-forming agents there are suitable: for example 
non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid 
esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl 
polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as 
well as albumen hydrolysis products; as dispersing agents there are 
suitable: for example lignin-sulphite waste liquors and methylcellulose. 
Adhesives such as carboxymethylcellulose and natural and synthetic polymers 
in the form of powders, granules or latices, such as gum arabic, polyvinyl 
alcohol and polyvinyl acetate, as well as natural phospholipids, such as 
cephalins and lecithins, and synthetic phospholipids, can be used in the 
formulations. Other additives can be mineral and vegetable oils. 
It is possible to use colorants such as inorganic pigments, for example 
iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such 
as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, 
and trace nutrients such as salts of iron, manganese, boron, copper, 
cobalt, molybdenum and zinc. 
The formulations in general contain between 0.1 and 95 per cent by weight 
of active compound, preferably between 0.5 and 90%. 
The active compounds according to the invention can be present in their 
commercially available formulations and in the use forms, prepared from 
these formulations, as a mixture with other active compounds, acaricides, 
nematicides, fungicides, growth-regulating substances or herbicides. The 
insecticides include, for example, phosphates, carbamates, carboxylates, 
chlorinated hydrocarbons, phenylureas and substances produced by 
microorganisms, inter alia. 
The active compounds according to the invention can furthermore be present 
in their commercially available formulations and in the use forms, 
prepared from these formulations, as a mixture with synergistic agents. 
Synergistic agents are compounds which increase the action of the active 
compounds, without it being necessary for the synergistic agent added to 
be active itself. 
The active compound content of the use forms prepared from the commercially 
available formulations can vary within wide limits. The active compound 
concentration of the use forms can be from 0.0000001 to 95% by weight of 
active compound, preferably between 0.0001 and 1% by weight. 
The compounds are employed in a customary manner appropriate for the use 
forms. 
When used against hygiene pests and pests of stored products, the active 
compounds are distinguished by an excellent residual action on wood and 
clay as well as a good stability to alkali on limed substrates. 
The active compounds which can be used according to the invention are also 
suitable for combating insects, midges, ticks etc. in the sectors of 
animal keeping and cattle breeding; better results, for example higher 
milk production, greater weight, more attractive animal pelt, longer life 
etc., can be achieved by combating the pests. 
The application of the active compounds which can be used according to the 
invention occurs in this sector in a known fashion, such as by oral 
application in the form of, for example, tablets, capsules, potions, 
granules, by means of dermal or external application in the form of, for 
example, dipping, spraying, pouring-on, spotting-on and dusting, as well 
as by means of parenteral application in the form, for example, of 
injection, and, furthermore, by means of the feed-through process. In 
addition, application as moulded articles (collar, ear tag) is also 
possible. 
The biological effectiveness of the compounds according to the invention 
will be explained with reference to the examples below.

PREATION EXAMPLES 
Example 1 
##STR37## 
(Process a) 
3.4 ml (0.03 mol) of ethyl bromoacetate are added dropwise with stirring at 
room temperature to a mixture of 9.3 g (0.02 mol) of 
1-(2,6-dichloro-4-trifluoromethylphenyl) 
-3-methyl-4-trifluoromethylthio-5-propionamidopyrazole (cf., for example, 
European Patent No. 201,852) and 0.87 g (0.03 mol) of sodium hydride (80% 
pure in paraffin) in 90 ml of absolute tetrahydrofuran; when the addition 
is complete, the mixture is stirred for 3 more hours at room temperature, 
100 ml of saturated aqueous ammonium chloride solution are then added, the 
mixture is extracted several times using dichloromethane, the combined 
organic extracts are washed with saturated aqueous sodium chloride 
solution and dried over sodium sulphate, and the solvent is removed in 
vacuo. 
This gives 11.1 g (100% of theory) of ethyl 
N-propionyl-N-[1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-trifluo 
romethylthio-5-pyrazolyl]-glycinate of melting point 73.degree. C. to 
74.degree. C. 
Example 2 
##STR38## 
(Process b) 
6 g (0.011 mol) of ethyl 
N-propionyl-N-[1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-trifluo 
romethylthio-5-pyrazolyl]-glycinate are stirred for about 8 hours at 
50.degree. C. in 25 ml of 80% strength sulphuric acid. The reaction 
mixture is then transferred into 200 ml of ice-water, the precipitated 
product is filtered off and dissolved in 2-normal sodium hydroxide 
solution, the solution is washed with dichloromethane, precipitation is 
then induced again by acidifying the solution with icecooling, and the 
product is filtered off with suction, washed with water and dried. 
This gives 4.3 g (84% of theory) of 
N-[1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-trifluoromethylthio 
-5-pyrazolyl]-glycine of melting point 168.degree.-170.degree. C. 
Example 3 
##STR39## 
(Process c) 
A solution of 3 g (0.0062 mol) of 
N-[1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-trifluoromethylthio 
-5-pyrazolyl]-glycine and 0.9 ml of concentrated sulphuric acid in 30 ml of 
absolute methanol is stirred for 4 hours at 20.degree. C. and then 
concentrated in vacuo, the residue is taken up in ether, and the solution 
is washed with saturated aqueous sodium hydrogen carbonate solution, dried 
over sodium sulphate and concentrated in vacuo. 
This gives 2.3 g (77% of theory) of methyl 
N-[1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-trifluoromethylthio 
-5-pyrazolyl]-glycinate as an oil. 
.sup.1 H--NMR (CDCl.sub.3 /tetramethylsilane): .delta.=7.77 (s, 2H, aryl) 
ppm. 
Example 4 
##STR40## 
(process c) 
A mixture of 4.7 g (0.01 mol) of 
N-[1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-trifluoromethylthio 
-5-pyrazolyl]-glycine, 2.1 g (0.01 mol) of phosphorus pentachloride and 100 
ml of absolute ether is refluxed for 15 minutes and then concentrated in 
vacuo, the residue is taken up in 50 ml of n-butanol, and the solution is 
stirred for 16 hours at room temperature. For working up, the mixture is 
concentrated in vacuo, the residue is taken up in dichloromethane, and the 
solution is washed with water, dried over sodium sulphate and freed from 
the solvent in vacuo. 
This gives 3.5 g (67% of theory) of 
N-[1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-trifluoromethylthio 
-5-pyrazolyl]-glycinate as an oil. 
.sup.1 H--NMR (CDCl.sub.3 /tetramethylsilane): .delta.=7.75 ppm (s, 2H, 
aryl). 
Example 5 
##STR41## 
(Process d) 
3.3 m1 (0.0315 mol) of dichlorofluoromethanesulphenyl chloride are added 
dropwise with stirring at 15.degree. C. to 10 g (0.0262 mol) of 
N-[1-(2,6-dichloro-4-trifluoromethylphenyl)-5-pyrazolyl]-4-aminobutyric 
acid in 40 ml of glacial acetic acid, the reaction mixture is subsequently 
stirred for 5 hours at room temperature and then transferred into 
ice-water, and the product which has precipitated is filtered off with 
suction, washed with water and dried in vacuo at 50.degree. C. 
This gives 12.0 g (89% of theory) of 
N-[1-(2,6-dichloro-4-trifluoromethylphenyl)-4-dichlorofluoromethanesulphen 
yl-5-pyrazolyl]-4-aminobutyric acid of melting point 99.degree. C. to 
101.degree. C. 
PREATION OF THE STARTING COMPOUND 
Example V-1 
##STR42## 
61.5 g (0.169 mol) of 
1-[1-(2,6-dichloro-4-trifluoromethylphenyl)-5-pyrazolyl]-pyrrolidin-2-one 
are refluxed with stirring for 24 hours in 250 ml of 48 per cent strength 
hydrobromic acid. For working up, the in water, the mixture is neutralized 
using 4 per cent strength aqueous sodium hydroxide solution, the solid 
which has precipitated is washed and dried and taken up in n-hexane, the 
mixture is stirred, and the precipitate is again filtered with suction and 
dried at 50.degree. C. in vacuo. 
This gives 39.4 g (61% of theory) of 
N-[1-(2,6-dichloro-4-trifluoromethylphenyl)-5-pyrazolyl]-4-aminobutyric 
acid of melting point 160.degree.-162.degree. C. 
Example IX-1 
##STR43## 
30 ml of concentrated ammonia water are added to 67.7 g (0.169 mol) of 
5-(4-chlorobutanoyl)-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazo 
le (cf., for example, European Patent No. 154,115) in 120 ml of ethanol, 
the mixture is stirred for 24 hours at room temperature and concentrated 
in vacuo, and the resulting crude product is directly reacted further to 
Example V-1. 
This gives 61.5 g (98% of theory) of 
1-[1-(2,6-dichloro-4-trifluoromethylphenyl)-5-pyrazolyl]-pyrrolidin-2-one 
of melting point 130.degree.-131.degree. C. 
Example VIII-1 
##STR44## 
In a first step, 15 ml (0.186 mol) of anhydrous pyridine are added to 50 g 
(0.169 mol) of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole 
(cf. European Patent No. 154,115) in 250 ml of acetonitrile, and 20.3 ml 
(0.178 mol) of 4-chlorobutanoyl chloride are then added dropwise with 
stirring at room temperature, during which process the temperature of the 
reaction mixture rises to 30.degree. C. When the addition is complete, the 
reaction mixture is stirred for one more hour at room temperature and then 
transferred, with stirring, into 1,000 ml of water, and the product which 
has precipitated is filtered off with suction and dried in vacuo at 
50.degree. C. 
This gives 67.7 g (100% of theory) of 
5-(4-chlorobutanoylamino)-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazol 
e of melting point 103.degree. to 104.degree. C. 
The following substituted 1-arylpyrazoles of the general formula (I) are 
obtained in a corresponding manner and following the general preparation 
instructions: 
##STR45## 
__________________________________________________________________________ 
Example No. 
R.sup.1 
R.sup.2 
n R.sup.3 
Ar physical 
__________________________________________________________________________ 
properties 
6 CH.sub.3 
CF.sub.3 
0 H CH.sub.2COOC.sub.2 H.sub.5 
##STR46## 
.sup.1 H-NMR*: 7.77 
7 CH.sub.3 
CF.sub.3 
0 H CH.sub.2COO(CH.sub.2).sub.2CH.sub.3 
##STR47## 
.sup.1 H-NMR*: 7.78 
8 CH.sub.3 
CF.sub.3 
0 H CH.sub.2COOCH(CH.sub.3).sub.2 
##STR48## 
.sup.1 H-NMR*: 7.78 
9 CH.sub.3 
CF.sub.3 
0 H 
##STR49## 
##STR50## 
.sup.1 H-NMR*: 7.72 
10 CH.sub.3 
CF.sub.3 
0 H CH.sub.2CON(CH.sub.3).sub.2 
##STR51## 
Fp 109.degree. C. 
11 H CF.sub.3 
0 
##STR52## 
COOC.sub.2 H.sub.5 
##STR53## 
Fp 70-73.degree. C. 
12 H CF.sub.3 
0 H COOH 
##STR54## 
Fp 97.degree. C. 
(Zers.) 
13 H CF.sub.3 
0 H COOH 
##STR55## 
Fp 101-103.degree. 
14 H CF.sub.3 
1 H (CH.sub.2).sub.3COOH 
##STR56## 
.sup.1 H-NMR*: 7.90 
15 H CF.sub.3 
2 H (CH.sub.2).sub.3COOH 
##STR57## 
Fp: 98-101.degree. 
16 H CCl.sub.2 F 
1 H (CH.sub.2).sub.3COOH 
##STR58## 
.sup.1 H-NMR* 7.85 
17 H CCl.sub.2 F 
2 H (CH.sub.2).sub.3COOH 
##STR59## 
Fp: 108-116.degree. 
18 H CF.sub.3 
0 H (CH.sub.2).sub.3COOC.sub.2 H.sub.5 
##STR60## 
.sup.1 H-NMR* 7.67 
19 H CCl.sub.2 F 
0 H (CH.sub.2).sub.3COOC.sub.2 H.sub.5 
##STR61## 
.sup.1 H-NMR* 7.72 
20 H CCl.sub.2 F 
0 
##STR62## 
CH.sub.2COOC.sub.2 H.sub.5 
##STR63## 
Fp: 104-107.degree. 
21 H CCl.sub.2 F 
1 H (CH.sub.2).sub.3COOC.sub.2 H.sub.5 
##STR64## 
.sup.1 H-NMR* 7.91 
22 H CCl.sub.2 F 
2 H (CH.sub.2).sub.3COOC.sub.2 H.sub.5 
##STR65## 
.sup.1 H-NMR* 7.89 
23 H CCl.sub.2 F 
0 H CH.sub.2COOH 
##STR66## 
Fp: 156-159.degree. 
24 H CF.sub.3 
1 H (CH.sub.2).sub.3COOC.sub.2 H.sub.5 
##STR67## 
.sup.1 H-NMR* 7.95 
25 H CF.sub.3 
2 H (CH.sub.2).sub.3COOC.sub.2 H.sub.5 
##STR68## 
.sup.1 H-NMR* 7.87 
26 H CF.sub.3 
0 H CH.sub.2COOC.sub.2 H.sub.5 
##STR69## 
Fp: 64-70.degree. C. 
27 H CCl.sub.2 F 
0 H CH.sub.2COOC.sub.2 H.sub.5 
##STR70## 
__________________________________________________________________________ 
*The .sup.1 HNMR spectra were recorded in deuterochloroform (CDCl.sub.3) 
with tetramethylsilane (T) the internal standard. The chemical shift of 
the phenyl protons in the Ar substituent indicated as .delta. value in 
ppm. 
USE EXAMPLES 
In the Use Examples which follow, the compounds listed below are employed 
as comparison substances: 
##STR71## 
1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-dichlorofluoromethylsu 
l 
phonyl-5-propionamidopyrazole 
##STR72## 
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylthio-pyrazole 
##STR73## 
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-dichloromethylt 
hio-pyrazole 
##STR74## 
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-4-dichlorofluoro 
m 
ethylsulphinyl-pyrazole 
##STR75## 
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulphony 
l 
-pyrazole 
(all known from European Patent No. 201,852) 
EXAMPLE A 
Myzus test (long-term action after watering) 
Solvent: 7 parts by weight of dimethylformamide 
Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amount of solvent and the stated 
amount of emulsifier, and the concentrate is diluted with water to the 
desired concentration. 
Cabbage leaves (Brassica oleracea) which are heavily infested with peach 
aphids (Myzus persicae) are treated by being dipped into a preparation of 
active compound of the desired concentration. 
After the specified periods of time, the destruction in % is determined. 
100% means that all the aphids have been killed; 0% means that none of the 
aphids have been killed. 
In this test, a superior activity compared with the prior art is shown, for 
example, by the following compounds of the Preparation Examples: 3, 13, 23 
and 26. 
EXAMPLE B 
Phaedon larvae test 
Solvent: 7 parts by weight of dimethylformamide 
Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amount of solvent and the stated 
amount of emulsifier, and the concentrate is diluted with water to the 
desired concentration. 
Cabbage leaves (Brassica oleracea) are treated by being dipped into the 
preparation of the active compound of the desired concentration and are 
infested with mustard beetle larvae (Phaedon cochleariae), as long as the 
leaves are still moist. 
After the specified periods of time, the destruction in % is determined. 
100% means that all the beetle larvae have been killed; 0% means that none 
of the beetle larvae have been killed. 
In this test, a superior activity compared with the prior art is shown, for 
example, by the following compounds of the Preparation Examples: 3, 26 and 
27. 
EXAMPLE C 
Spodoptera test 
Solvent: 7 parts by weight of dimethylformamide 
Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amount of solvent and the stated 
amount of emulsifier, and the concentrate is diluted with water to the 
desired concentration. 
Cabbage leaves (Brassica oleracea) are treated by being dipped into the 
preparation of active compound of the desired concentration and are 
infested with caterpillars of the owlet moth (Spodoptera frugiperda), as 
long as the leaves are still moist. 
After the specified periods of time, the destruction in % is determined. 
100% means that all the caterpillars have been killed; 0% means that none 
of the caterpillars have been killed. 
In this test, a superior activity compared with the prior art is shown, for 
example, by the following compounds of the Preparation Examples: 16, 17, 
23, 26 and 27. 
EXAMPLE D 
Critical concentration test/soil insects 
Test insect: Phorbia antiqua maggots (in the soil) 
Solvent: 3 parts by weight of acetone 
Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amount of solvent, the stated 
amount of emulsifier is added and the concentrate is diluted with water to 
the desired concentration. 
The preparation of active compound is intimately mixed with soil. The 
concentration of the active compound in the preparation is of practically 
no importance here, only the amount by weight of active compound per unit 
volume of soil, which is given in ppm (=mg/1), being decisive. The soil is 
transferred into pots and the pots are left to stand at room temperature. 
After 24 hours, the test animals are introduced into the treated soil, and 
after a further 2 to 7 days the degree of effectiveness of the active 
compound is determined in % by counting the dead and live test insects. 
The degree of effectiveness is 100% if all the test insects have been 
killed and is 0% if just as many test insects are still alive as in the 
case of the untreated control. 
In this test, a superior activity compared with the prior art is shown, for 
example, by the following compounds of the Preparation Examples: 2, 3, 4, 
6, 7, 8, 9, 10, 14 and 17. 
EXAMPLE E 
Critical concentration test/soil insects 
Test insect: Diabrotica balteata larvae (in the soil) 
Solvent: 3 parts by weight of acetone 
Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amount of solvent, the stated 
amount of emulsifier is added and the concentrate is diluted with water to 
the desired concentration. The preparation of active compound is 
intimately mixed with soil. The concentration of the active compound in 
the preparation is of practically no importance here, only the amount by 
weight of active compound per unit volume of soil, which is given in ppm 
(=mg/1), being decisive. The soil is transferred into pots and the pots 
are left to stand at 20.degree. C. 
Immediately after preparation, 6 pre-germinated maize seeds are placed in 
each pot. After 2 days the corresponding test insects are introduced into 
the treated soil. After a further 7 days the degree of effectiveness of 
the active compound is determined in % by counting the dead and live test 
insects. The degree of effectiveness is 100% if all the test insects have 
been killed and is 0% if just as many test insects are still alive as in 
the case of the untreated control. 
In this test, a superior activity compared with the prior art is shown, for 
example, by the following compounds of the Preparation Examples: 2 and 3. 
EXAMPLE F 
Critical concentration test/root-systemic action 
Test insect: Phaedon cochleariae--larvae 
Solvent: 3 parts by weight of acetone 
Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amount of solvent, the stated 
amount of emulsifier is added and the concentrate is diluted with water to 
the desired concentration. 
The preparation of active compound is intimately mixed with soil. The 
concentration of the active compound in the preparation is of practically 
no importance, only the amount by weight of active compound per unit 
volume of soil, which is given in ppm (=mg/1), being decisive. The treated 
soil is transferred into pots and these are planted with cabbage (Brassica 
oleracea). The active compound can in this way be taken up from the soil 
by the roots of the plants and be transported into the leaves. 
To demonstrate the root-systemic effect, exclusively the leaves are 
infested with the abovementioned test animals after 7 days. After a 
further 2 days, the evaluation is made by counting or estimating the dead 
animals. The root-systemic action of the active compound is deduced from 
the mortality figures. It is 100% if all test animals have been killed and 
0% if just as many test insects are still alive as in the case of the 
untreated control. 
In this test, a superior activity compared with the prior art is shown, for 
example, by the following compounds of the Preparation Examples: 1, 2, 3, 
4, 6, 7, 8, 9, 10, 12, 14 and 16. 
EXAMPLE G 
Critical concentration test/root-systemic action 
Test insect: Myzus persicae 
Solvent: 3 parts by weight of acetone 
Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amount of solvent, the stated 
amount of emulsifier is added and the concentrate is diluted with water to 
the desired concentration. 
The preparation of active compound is intimately mixed with soil. The 
concentration of the active compound in the preparation is of practically 
no importance, only the amount by weight of active compound per unit 
volume of soil, which is given in ppm (=mg/1), being decisive. The treated 
soil is transferred into pots and these are planted with cabbage (Brassica 
oleracea). The active compound can in this way be taken up from the soil 
by the roots of the plants and be transported into the leaves. 
To demonstrate the root-systemic effect, exclusively the leaves are 
infested with the abovementioned test animals after 7 days. After a 
further 2 days, the evaluation is made by counting or estimating the dead 
animals. The root-systemic action of the active compound is deduced from 
the mortality figures. It is 100% if all test animals have been killed and 
0% if just as many test insects are still alive as in the case of the 
untreated control. 
In this test, a superior activity compared with the prior art is shown, for 
example, by the following compounds of the Preparation Examples: 3 us 12. 
EXAMPLE H 
Seed treatment test/soil insects 
Test insect: Phorbia antiqua grubs in the soil 
Test plant: Allium cepa 
Solvent: 1 part by weight of acetone 
Carrier: kaolin 
To produce a suitable preparation of active compound, the active compound 
is dissolved in acetone and 1 part by weight of active compound/acetone is 
mixed with 5 parts by weight of kaolin. The onion seeds are treated with 
this active compound preparation at the application rates required. They 
are sown in 0.5 liter pots containing standardized soils at a greenhouse 
temperature of 20.degree. C. 
After emergence of the onions, they are artificially infected with onion 
fly eggs. 
Evaluation is carried out after 14 days. The degree of action is 100% if 
all the onion plants remain standing, and 0% if all the test plants have 
been destroyed (as in the untreated control). 
In this test, a superior action compared with the prior art is shown, for 
example, by the following compounds of the Preparation Examples: 2, 3 and 
12. 
EXAMPLE I 
Seed treatment test/root-systemic action 
Test insect: Phaedon cochleariae beetles 
Test plant: Brassica oleracea 
Solvent: 1 part by weight of acetone 
Carrier: kaolin 
To produce a suitable preparation of active compound, the active compound 
is dissolved in acetone, and 1 part by weight of active compound/acetone 
is mixed with 5 parts by weight of kaolin. The cabbage seeds are treated 
with this active compound preparation at the application rates required. 
The cabbage is sown in 0.5 liter pots containing standardized soils at a 
room temperature of 20.degree. C. 
The active compound can thus be taken up from the soil by the plant roots 
and transported into the leaves. 
For detection of the root-systemic effect, exclusively the leaves are 
infested with the abovementioned test animals after 14 days. After a 
further 3 days, the evaluation is carried out by counting or estimating 
the dead animals. The root-systemic action of the active compound is 
derived from the destruction killed and 0% if just as many test insects 
are still alive as in the untreated control. 
In this test, a superior action compared with the prior art is shown, for 
example, by the following compounds of the Preparation Examples: 2, 3 and 
12. 
EXAMPLE K 
Tick test (Boophilus microplus)/Inhibition of egg deposition 
Solvent: 35 parts by weight of ethylene glycol monomethyl ether 
35 parts by weight of nonylphenol polyglycol ether 
To produce a suitable formulation, three parts by weight of active compound 
are mixed weight of the abovementioned solvent/emulsifier mixture, and the 
emulsion concentrate thus obtained is diluted with water to the specific 
desired concentration. 
Adult female ticks which have sucked themselves full of the species 
Boophilus microplus (sensitive and resistant, respectively) are immersed 
for one minute in this active compound preparation After 10 female 
specimens of each of the different tick species have been immersed, they 
are transferred into Petri dishes in which a filterpaper disc of 
appropriate size has been placed on the bottom. 
After 10 days, the effectiveness of the active compound preparation is 
determined by comparing the inhibition of egg deposition with untreated 
control ticks. The action is expressed as a percentage, 100% denoting that 
no eggs were deposited any longer and 0% denoting that the ticks deposited 
normal amounts of eggs. 
In this test, a superior action compared with the prior art is shown, for 
example, by the following compounds of Preparation Examples 1 and 20.