Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-06-28
2003-01-07
Berch, Mark L (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S256000, C514S333000, C514S362000, C514S365000, C514S372000, C514S374000, C514S378000, C514S383000, C514S392000, C544S335000, C544S336000, C544S405000, C546S274700, C548S134000, C548S205000, C548S214000, C548S235000, C548S247000, C548S267400, C548S312400, C548S314700
Reexamination Certificate
active
06503912
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The present application relates to novel guanidine derivatives, to a process for their preparation and to their use for controlling animal pests.
BACKGROUND OF THE INVENTION
Is already known that certain heterocyclic compounds have insecticidal properties (cf., for example, EP-A 0 192 060, EP-A 0 277 317, Literature references according to CA 125, 188 277; 121, 255 796; 121, 157 642).
However, in particular at low application rates and concentrations, the activity and/or activity spectrum of these compounds is not entirely satisfactory in all areas of use.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel guanidine derivatives of the formula (I)
in which
R
1
represents a five- or six-membered heterocyclic grouping which contains 1, 2, 3 or 4 nitrogen atoms and/or one or two oxygen or sulphur atoms as heteroatom ring members—where the number of heteroatoms is 1, 2, 3 or 4- and which is optionally substituted by halogen, cyano, nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkinyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkinyloxy, alkylthio, halogenoalkylthio, alkenylthio, halogenoalkenylthio, alkinylthio, alkylsinphinyl, halogenoalkylsinphinyl, alkylsulphonyl, halogenoalkylsulphonyl, amino, alkylamino, dialkylamino, aryl, arylthio, arylamino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and/or alkoxycarbonyl;
R
2
represents hydrogen or alkyl,
R
3
represents the groupings —OR
4
, —OCOR
5
, —OCOOR
6
, —OCONR
7
R
8
and —OSO
2
R
9
, where
R
4
, R
5
and R
6
independently of one another represent alkyl, alkoxyalkyl, halogenoalkyl, alkenyl, alkinyl, alkylaminoalkyl, dialkylaminoalkyl, optionally substituted cycloalkyl and in each case optionally substituted phenyl or benzyl,
R
7
and R
8
independently of one another represent hydrogen, alkyl, alkenyl and in each case optionally substituted phenyl or benzyl and
R
9
represents alkyl or optionally substituted phenyl,
A represents the groupings —CH
2
CH
2
—, (CH
2
)
3
and —CH═CH— and
z represents cyano or nitro,
with the proviso that, if Z represents NO
2
and A represents —CH
2
CH
2
—, the radical R
2
represents hydrogen; and the compound of the formula (I) in which
R
1
R
2
H,
R
3
OCH
3
,
A —CH
2
CH
2
— and
Z NO
2
is excluded.
Furthermore, it has been found that the compounds of the formula (I) are obtained when compounds of the formula (II)
in which
R
1
, A and Z are as defined above
are reacted with halogen compounds of the formula (III)
in which
R
2
and R
3
are as defined above and
x represents halogen (in particular chlorine or bromine),
in the presence of a base and if appropriate in the presence of a diluent.
Finally, it has been found that the novel compounds 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 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
1
preferably represents a five- to six-membered heterocyclic grouping from the group consisting of pyrazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrazinyl and pyrimidinyl, which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C
1
-C
2
-alkyl (which is optionally substituted by fluorine and/or chlorine), C
1
-C
2
-alkoxy (which is optionally substituted by fluorine and/or chlorine), C
1
-C
2
-alkylthio (which is optionally substituted by fluorine and/or chlorine), or C
1
-C
2
-alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine),
R
2
preferably represents hydrogen or C
1
-C
6
-alkyl,
R
3
preferably represents the groupings —OR
4
, —OCOR
5
, —OCOOR
6
, —OCONR
7
R
8
and —OSO
2
R
9
, where
R
4
, R
5
and R
6
independently of one another preferably represent C
1
-C
12
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms; C
2
-C
4
-alkenyl, C
2
-C
4
-alkinyl, C
1
-C
4
-alkylamino-C
1
-C
4
-alkyl, di(C
1
-C
4
)-alkylamino-C
1
-C
4
-alkyl, represent C
3
-C
6
-cycloalkyl which is optionally mono- to trisubstituted by identical or different substituents, preferred substituents which may be mentioned being: halogen, C
1
-C
4
-alkyl and C
1
-C
4
-halogenoalkyl having 1 to 5 identical or different halogen atoms, such as F, Cl and Br atoms, or represent phenyl or benzyl, each of which is optionally mono- to trisubstituted by identical or different substituents, preferred phenyl substituents being in each case: halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-halogenoalkyl and C
1
-C
4
-halogenoalkoxy having in each case 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms and nitro.
R
7
and R
8
independently of one another preferably represent hydrogen, C
1
-C
6
-alkyl, C
2
-C
4
-alkenyl or represent phenyl or benzyl, each of which is mono- to trisubstituted by identical or different substituents, preferred phenyl substituents being in each case: halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-halogenoalkyl and C
1
-C
4
-halogenoalkoxy having in each case 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms; and
R
9
preferably represents C
1
-C
4
-alkyl or represents phenyl which is mono- to trisubstituted by identical or different substituents, possible substituents being: halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-halogenoalkyl and C
1
-C
4
-halogenoalkoxy having in each case 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms,
A preferably represents the groupings —CH
2
CH
2
—, —(CH
2
)
3
— and —CH═CH—.
z preferably represents cyano or nitro,
with the proviso that, if Z represents NO
2
and A represents —CH
2
CH
2
—, the radical R
2
represents hydrogen; and the compound of the formula (I) in which
R
1
R
2
H, R
3
OCH
3
,
A —CH
2
CH
2
— and
Z NO
2
is excluded.
R
1
particularly preferably represents 6-chloro-3-pyridyl (6-chloro-pyridin-3-yl) or represents 2-chloro-5-thiazolyl (2-chloro-thiazol-5-yl),
R
2
particularly preferably represents hydrogen or C
1
-C
5
-alkyl,
R
3
particularly preferably represents the groupings —OR
4
, —OCOR
5
, —OCOOR
6
, —OCONR
7
R
8
and —OSO
2
R
9
, where
R
4
, R
5
and R
6
independently of one another particularly preferably represent C
1
-C
8
-alkyl, C
1
-C
2
-alkoxy-C
1
-C
2
-alkyl, C
1
-C
2
-halogenoalkyl having 1 to 2 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms; allyl, propargyl, C
1
-C
2
-alkylamino-C
1
-C
2
-alkyl, di(C
1
-C
2
)-alkylamino-C
1
-C
2
-alkyl, cyclopropyl, cyclopentyl, cyclohexyl or represent phenyl or benzyl, each of which is optionally mono- to disubstituted by identical or different substituents, possible phenyl substituents being in each case: fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy and nitro.
R
7
and R
8
independently of one another particularly preferably represent hydrogen, C
1
-C
4
-alkyl, vinyl, allyl or represent phenyl or benzyl, each of which is optionally mono- to disubstituted by identical or different substituents, possible phenyl substituents being in each case: fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl and trifluoromethoxy; and
R
9
particularly preferably represents methyl, ethyl or phenyl which is optionally mono- to disubstituted by identical or different substituents, possible substituents being: fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl and trifluoromethoxy,
A particularly preferably represents the groupings —CH
2
CH
2
— and —CH═CH—,
Z particularly preferably represents cyano or nitro
Andersch Wolfram
Erdelen Christoph
Mencke Norbert
Turberg Andreas
Wachendorff-Neumann Ulrike
Bayer Aktiengesellschaft
Berch Mark L
Gil Joseph C.
McKenzie Thomas
Mrozinski, Jr. John E.
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