N-aryl-1,2,4-triazolin-5-ones

Details N-aryl-1,2,4-triazolin-5-ones N-aryl-1,2,4-triazolin-5-ones

1997-12-02

2001-07-10

Morris, Patricia L. (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S263800, C548S264400

Reexamination Certificate

active

06258957

ABSTRACT:

The present invention relates to the use of novel and known N-aryl-1,2,4-triazolin-5-ones for controlling animal pests, in particular insects, arachnids and nematodes, encountered in agriculture, in forests, in the protection of store products and materials, and in the hygiene field.
It is already known that certain substituted N-aryl-1,2,4-triazolin-5-one derivatives have herbicidal properties (cf. for example EP-A-0 610 733 and EP-A-0 617 026). Nothing is known about an insecticidal activity of the compounds known from EP-A-0 617 026. The compounds known from EP-A-0 610 733 are claimed to have activity against leaf insects and acarids at the appropriate application rates. However, the insecticidal activity of these compounds, in particular at low application rates and concentrations, is not always satisfactory.
This invention, accordingly, provides novel and known N-aryl-1,2,4-triazolin-5-ones of the formula (I)
in which
A represents nitrogen or the group CR,
R represents hydrogen, halogen, nitro, cyano, hydroxyl, optionally halogen-, cyano-, nitro-, alkoxy- or amino-substituted alkyl, optionally substituted cycloalkyl or the radical —CX—NY
1
Y
2
,
R
1
represents halogen, nitro, cyano, respectively optionally halogen-, cyano-, nitro-, alkoxy- or amino-substituted alkyl or alkoxy, optionally substituted cycloalkyl or the radical —CX—NY
1
Y
2
,
R
2
represents hydrogen, halogen, optionally halogen-, cyano-, nitro-, alkoxy- or amino-substituted alkyl or optionally substituted cycloalkyl,
R
3
represents nitro, halogenoalkyl, halogenoalkoxy or the radical —S(O)
n
R
6
,
R
4
represents halogen, nitro, cyano, respectively optionally halogen-, cyano-, nitro-, alkoxy- or amino-substituted alkyl or alkoxy, represents alkenyl, alkenyloxy, alkinyl, hydroxyl, mercapto, respectively optionally substituted cycloalkyl or cycloalkylalkyl, respectively optionally substituted aryl, aryloxyalkyl or aralkyl or the radical —S(O)
n
R
6
,
R
5
represents hydrogen, cyano, respectively optionally halogen-, cyano-, nitro-, alkoxy- or amino-substituted alkyl or alkoxy, represents alkenyl, alkenyloxy, alkinyl, alkinyloxy, respectively optionally substituted cycloalkyl or cycloalkylalkyl, respectively optionally substituted aryl or aralkyl or one of the radicals —S(O)
n
R
6
, —NR
7
R
8
or —N═CR
9
R
10
,
R
6
represents optionally halogen-, cyano-, nitro-, alkoxy- or amino-substituted alkyl, represents alkenyl, alkanedienyl, alkinyl, optionally substituted cycloalkyl or optionally substituted aryl,
R
7
represents hydrogen, optionally halogen-, cyano-, nitro-, alkoxy- or amino-substituted alkyl, represents alkenyl, alkinyl, alkoxy, optionally substituted cycloalkyl or optionally substituted aryl,
R
8
represents hydrogen, optionally halogen-, cyano-, nitro-, alkoxy- or amino-substituted alkyl, represents alkenyl, alkinyl, alkoxy, optionally substituted cycloalkyl or optionally substituted aryl, or
R
7
and R
8
join with the linking nitrogen atom to represent an optionally substituted heterocycle which may optionally contain one or more additional hetero atoms,
R
9
represents hydrogen, optionally halogen-, cyano-, nitro-, alkoxy- or amino-substituted alkyl, represents alkoxy, optionally substituted cycloalkyl or respectively optionally substituted aryl or heterocyclyl,
R
10
represents hydrogen, optionally halogen-, cyano-, nitro-, alkoxy- or amino-substituted alkyl, represents alkoxy, optionally substituted cycloalkyl or respectively optionally substituted aryl or heterocyclyl,
X represents oxygen or sulphur,
Y
1
represents hydrogen or alkyl,
Y
2
represents hydrogen or alkyl, and
n represents one of the numbers 0, 1 or 2,
which are highly suitable for controlling animal pests, in particular insects, arachnids and nematodes.
Depending on the nature of the substituents, the compounds of the formula (I) can be present as geometric and/or optical isomers or isomer mixtures of differing composition. The invention relates both to the pure isomers and to the isomer mixtures.
Surprisingly, the N-aryl-1,2,4-triazolin-5-ones used according to the invention have appreciably better activity against animal pests than the constitutionally most similar prior-art compounds.
Formula (I) provides a general definition of the N-aryl-1,2,4-triazolin-5-ones usable according to the invention.
Preferred substituents and ranges of the radicals recited in the formulae mentioned hereinabove and hereinbelow are illustrated in what follows.
A preferably represents nitrogen or the group CR.
R preferably represents hydrogen, fluorine, chlorine, bromine, nitro, cyano, hydroxyl, optionally fluorine-, chlorine-, cyano-, nitro- or C
1
-C
2
-alkoxy-substituted C
1
-C
4
-alkyl, optionally fluorine-, chlorine-, bromine-, C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkyl- or C
1
-C
4
-halogenoalkoxy-substituted C
3
-C
6
-cycloalkyl, or represents one of the radicals —CONH
2
, —CSNH
2
, —CO—NH—C
1
-C
4
-alkyl, —CS—NH—C
1
-C
4
-alkyl, —CO—N(C
1
-C
4
-alkyl)
2
, or —CS—N(C
1
-C
4
-alkyl)
2
.
R
1
preferably represents fluorine, chlorine, bromine, nitro, cyano, respectively optionally fluorine-, chlorine-, cyano-, nitro- or C
1
-C
2
-alkoxy-substituted C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy, optionally fluorine-, chlorine-, bromine-, C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkyl- or C
1
-C
4
-halogenoalkoxy-substituted C
3
-C
6
-cycloalkyl, or represents one of the radicals —CONH
2
, —CSNH
2
, —CO—NH—C
1
-C
4
-alkyl, —CS—NH—C
1
-C
4
-alkyl, —CO—N(C
1
-C
4
-alkyl)
2
, or —CS—N(C
1
-C
4
-alkyl)
2
.
R
2
preferably represents hydrogen, fluorine, chlorine, C
1
-C
4
-alkyl or C
1
-C
4
-halogenoalkyl.
R
3
preferably represents nitro, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy or one of the radicals —S—C
1
-C
4
-halogenoalkyl, —SO—C
1
-C
4
-halogenoalkyl, or —SO
2
—C
1
-C
4
-halogenoalkyl.
R
4
preferably represents halogen, nitro, cyano, respectively optionally fluorine-, chlorine-, cyano-, nitro-, C
1
-C
4
-alkoxy- or amino-substituted C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy, represents C
3
-C
6
-alkenyl, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkinyl, hydroxyl, mercapto, respectively optionally fluorine-, chlorine-, bromine-, C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkyl- or C
1
-C
4
-halogenoalkoxy-substituted C
3
-C
6
-cycloalkyl or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, represents phenyl, phenyloxy-C
1
-C
4
-alkyl or phenyl-C
1
-C
4
-alkyl, each of which is optionally substituted by halogen, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, C
1
-C
4
-halogenoalkylthio or optionally halogen- or C
1
-C
4
-alkyl-substituted phenyl, or represents the radical —S(O)
n
R
6
.
R
5
preferably represents hydrogen, cyano, respectively optionally fluorine-, chlorine-, cyano-, nitro-, C
1
-C
4
-alkoxy- or amino-substituted C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy, represents C
3
-C
6
-alkenyl, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkinyl, C
3
-C
6
-alkinyloxy, respectively optionally fluorine-, chlorine-, bromine-, C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkyl- or C
1
-C
4
-halogenoalkoxy-substituted C
3
-C
6
-cycloalkyl, or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, phenyl which is optionally substituted by halogen, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, C
1
-C
4
-halogenoalkylthio or optionally halogen- or C
1
-C
4
-alkyl-substituted phenyl, represents C
1
-C
4
-alkyl-substituted benzyl or one of the radicals —S(O)
n
R
6
, —NR
7
R
8
or —N═CR
9
R
10
.
R
6
preferably represents optionally fluorine-, chlorine-, cyano- or nitro-substituted C
1
-C
4
-alkyl, represents C
3
-C
6
-alkenyl, C
3
-C
6
-alkanedienyl, C
3
-C
6
-alkinyl, optionally fluorine-, chlorine-, bromine-, C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkyl- or C
1
-C
4
-halogenoalkoxy-substituted C
3
-C
6
-cycloalkyl, or phenyl which is optionally substituted by halogen, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalk

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