Title of Invention

PHENYL-SUBSTITUTED 4-HYDROXY TETRAHYDROPYRIDONES AND THEIR PROCESS OF PREPARATION

Abstract The present invention relates to novel compounds of the formula(I) in which W,X,Y,Z,G,A,B,Q1,Q2 AND D are each as defined in the description, to a plurality of processes for their preparation and to their use as pesticides and herbicides.
Full Text FORM 2
THE PATENTS ACT 1970
[39 OF 1970]
&
THE PATENTS (AMENDMENT) RULES 2006
COMPLETE SPECIFICATION
[See Section 10; rule 13]
"PHENYL-SUBSTITUTED 4-HYDROXY TETRAHYDROPYRIDONES AND THEIR PROCESS OF
PREPARATION"
BAYER AKTIENGESELLSCHAFT, a German company, of D-51368 Leverkusen, Germany,
The following specification particularly describes the invention and the manner in which it is to be performed:


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Phenvl-substituted 4-hydroxy-"tetrahydropyridones
The present invention relates to novel phenyl-substituted 4-hydroxy-
5 tetrahydropyridones, to a plurality of processes for their preparation and to their use
as pesticides and herbicides.
It is known that certain tetrahydropyridones have herbicidal properties: JP 0832530.
Moreover, specific 4-hydroxytetrahydropyridones having acaricidal, insecticidal and
10 herbicidal properties are known: JP 11152273.
However, the activity and activity spectrum of these compounds is, in particular at
low application rates and concentrations, not always entirely satisfactory.
Furthermore, the compatibility of these compounds with plants is not always
15 sufficient.
This invention, accordingly, provides novel compounds of the formula (I)
(I)
in which 20
W represents hydrogen, alkyl, alkenyl, alkinyl, halogen, halogenoalkyl or alkoxy,
X represents halogen, alkyl, alkoxy, alkenyl, alkinyl, halogenoalkyl,
halogenoalkoxy, cyano or in each case optionally substituted phenyl,
25 phenoxy, phenylthio, phenylalkoxy or phenylalkylthio,


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Y represents hydrogen, alkyl, halogen, alkoxy, alkenyl, alkinyl or optionally substituted aryl or hetaryl,
Z represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy
5 or cyano,
A represents hydrogen, in each case optionally halogen-substituted alkyl,
alkenyl, alkoxyalkyl, optionally substituted cycloalkyl or cycloalkyl-alkyl in
which optionally at least one ring atom is replaced by a heteroatom, or in each
10 case optionally halogen-, alkyl-, halogenoalkyl-, alkoxy-, halogenoalkoxy-,
cyano- or nitro-substituted aryl, arylalkyl, hetaryl or hetarylalkyl,
B represents hydrogen or alkyl, or
15 A and B together with the carbon atom to which they are attached represent a
saturated or unsaturated, unsubstituted or substituted cycle which optionally contains at least one heteroatom,
A and Q1 together represent alkenediyl which is optionally substituted by in each
20 case optionally substituted alkyl or alkoxy or,
D represents hydrogen,
D also represents an optionally substituted radical from the group consisting of
25 alkenyl, alkinyl, alkoxyalkyl, optionally substituted cycloalkyl and cycloalkyl-
alkyl in which optionally one or more ring members are replaced by heteroatoms,
D and Q1 together represent alkanediyl which is optionally substituted by in each
30 case optionally substituted alkyl or alkoxy or


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Q1 represents hydrogen, alkyl, alkoxyalkyl, optionally substituted cycloalkyl (in which optionally one methylene group is replaced by oxygen or sulphur) or optionally substituted phenyl, or
5 Q2 represents hydrogen or alkyl,
Q1 and Q2 together with the carbon atom to which they are attached represent an unsubstituted or substituted cycle which optionally contains a heteroatom,
10 G represents hydrogen (a) or represents one of the groups

in which
15
E represents a metal ion or an ammonium ion,
L represents oxygen or sulphur,
20 M represents oxygen or sulphur,
R.1 represents in each case optionally halogen-substituted alkyl, alkenyl,
alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally halogen-,
alkyl- or alkoxy-substituted cycloalkyl in which one or more
25 methylene groups may be replaced by heteroatoms, in each case
optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,


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R2 represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents or in each case optionally substituted cycloalkyl, phenyl or benzyl, 5
R3, R4 and R5 independently of one another represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio and represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio, and 10
R6 and R7 independently of one another represent hydrogen, in each case
optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy,
alkoxyalkyl, represent optionally substituted phenyl, represent
optionally substituted benzyl, or together with the N atom to which
15 they are attached represent a ring which is optionally interrupted by
oxygen or sulphur.
Depending inter alia on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and/or optical isomers or isomer mixtures in varying
20 composition which, if appropriate, can be separated in a customary manner. The
present invention provides both the pure isomers and the isomer mixtures, their preparation and use, and also compositions comprising them. However, hereinbelow, for the sake of simplicity, only compounds of the formula (I) are referred to, although this may mean both the pure compounds and, if appropriate, mixtures with varying
25 contents of isomeric compounds.
Depending on the location of the substituent G, the compounds of the formula (I) can be present in the two isomeric forms of the formulae (I-A) and (I-B),


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which is meant to be indicated by the broken line in formula (I).
The compounds of the formulae (I-A) and (I-B) can be present both as mixtures and
5 in the form of their pure isomers. Mixtures of the compounds of the formulae (I-A)
and (I-B) can, if appropriate, be separated in a manner known per se by physical methods, for example by chromatographic methods.
For reasons of clarity, hereinbelow only one of the possible isomers is shown in each
10 case. This does not exclude the fact that the compounds are, if appropriate, present in
the form of the isomer mixtures or in the respective other isomeric form.
Taking into account the different meanings (a), (b), (c), (d), (e), (0 and (g) of group G, the following principal structures (I-a) to (I-g) result
15



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10

in which
A, B, D, E, L, M, Q1, Q2, W, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 are each as defined above.
Furthermore, it has been found that the novel compounds of the formula (I) can be obtained by one of the processes described below;
(A) Substituted tetrahydropyridine-2,4-diones of their enols of the formula (I-a)


in which
i5 A, B, D, Q1, Q2, W, X, Y and Z are each as defined above,
are obtained when


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N-acylamino acid esters of the formula (II)

in which
A, B, D, Q1,Q2, W, X, Y and Z are each as defined above,
and
R8 represents alkyl (preferably C1-C6-alkyl),
are condensed intramolecularly in the presence of a diluent and in the presence of a base.
Furthermore, it has been found
(B) that compounds of the formulae (I-a) to (I-g) shown above in which A, B, D, G, Q1, Q2, W, X, Y and Z are each as defined above are obtained when compounds of the formulae (I-a") to (I-g"),



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10

in which
5 A, B, D, R1, R2, R3, R4, R5, R6, R7, E, L, M, Q1, Q2, W; X", Y" and Z" are each
as defined above and where at least one of the radicals
W, X", Y" represents chlorine, bromine or iodine, preferably bromine,
10 and Z" does not represent bromine or iodine,
a) are initially reacted with silylacetylene of the formula (HI)

15 in which
R9 represents hydrogen and
R10 represents C1-C4alkyl or phenyl, in particular methyl or tert-
20 butyl,


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11
in the presence of a solvent, a base and a catalyst, particularly suitable catalysts being palladium complexes, and the silyl group is then removed,
o or
(3) are reacted with vinylstannanes of the formula (IV)
(IV)
10 in which
R9 represents hydrogen, methyl or ethyl and R10 represents C1-C4 alkyl, in particular butyl,
15
in the presence of a solvent, if appropriate in the presence of a base and in the presence of a catalyst, particularly suitable catalysts being palladium complexes,
20 or
y) in the specific case where Y" represents chlorine, bromine or iodine, preferably bromine, are reacted with boronic acids of the formula (V)

25
in which
Y represents optionally substituted phenyl or hetaryl


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12
in the presence of a solvent, a base and a catalyst, particularly suitable catalysts being palladium complexes.
5 Moreover, it has been found
(C) that the compounds of the formula (I-b) shown above in which A, B, D, Ql,
Q2, R1, W, X, Y and Z are each as defined above are obtained when
compounds of the formula (I-a) shown above in which A, B, D, Ql, Q2, W,
10 X, Y and Z are each as defined above are in each case reacted
(a) with acid halides of the formula (VI)


(VI)

15 in which
Rl is as defined above and
Hal represents halogen (in particular chlorine or bromine)
20
or
(p) with carboxylic anhydrides of the formula (VII)






in which
Rl is as defined above,



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if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder;
5 (D) that the compounds of the formula (I-c) shown above in which A, B, D, Q1,
Q2, R2, M, W, X, Y and Z are each as defined above and L represents oxygen are obtained when compounds of the formula (I-a) shown above in which A, B, D, Q1, Q2, W, X, Y and Z are each as defined above are in each case reacted 10
with chloroformic esters or chloroformic thioesters of the formula (VIII)
R2-M-CO-C1 (VHI)
in which 15
R2 and M are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of
an acid binder; 20
(E) that compounds of the formula (I-c) shown above in which A, B, D, Q1, Q2,
R2, M, W, X, Y and Z are each as defined above and L represents sulphur are
obtained when compounds of the formula (I-a) shown above in which A, B,
D, Q1, Q2, W, X, Y and Z are each as defined above are in each case reacted 25
with chloromonothioformic esters or chlorodithiofonnic esters of the formula
(IX)

in which

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M and R2 are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of
5 an acid binder
and
(F) that compounds of the formula (I-d) shown above in which A, B, D, Q1, Q2,
10 R3, W, X, Y and Z are each as defined above are obtained when compounds
of the formula (I-a) shown above in which A, B, D, Q1, Q2, W, X, Y and Z are each as defined above are in each case reacted
with sulphonyl chlorides of the formula (X) 15
R3-SO2-C1 (X)
in which
R3 is as defined above, 20
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
(G) that compounds of the formula (I-e) shown above in which A, B, D, L, Q1,
25 Q2, R4, R5, W, X, Y and Z are each as defined above are obtained when
compounds of the formula (I-a) shown above in which A, B, D, Q1, Q2, W, X, Y and Z are each as defined above are in each case reacted
with phosphorus compounds of the formula (XI)


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15


10
15
20


in which
L, R4 and R5 are each as defined above and
Hal represents halogen (in particular chlorine or bromine),
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
(H) that compounds of the formula (I-f) shown above in which A, B, D, E, Q1, Q2, W, X, Y and Z are each as defined above are obtained when compounds of the formula (I-a) in which A, B, D, Q1, Q2, W, X, Y and Z are each as defined above are in each case reacted
with metal compounds or amines of the formulae (XII) and (XII)

in which
Me represents a mono- or divalent metal (preferably an alkali metal or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium),

25 t represents the number 1 or 2 and


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-16

10
15
20

independently of one another each represent hydrogen or alkyl (preferably C1-C8-alkyl),
if appropriate in the presence of a diluent,
(I) that compounds of the formula (I-g) shown above in which A, B, D, L, Q1,
Q2, R6, R7,
W, X, Y and Z are each as defined above are obtained when
compounds of the formula (I-a) shown above in which A, B, D, Q1, Q2, W, X, Y and Z are each as defined above are in each case
(a) reacted with isocyanates or isothiocyanates of the formula (XIV)
R6-N=C=L (XIV)
in which
R6 and L are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or
(B) are reacted with carbamoyl chlorides or thiocarbamoyl chlorides of the formula (XV)



25


in which
L, R6 and R7 are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.


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Furthermore, it has been found that the novel compounds of the formula (I) have very good activity as pesticides, preferably as insecticides and akaricides, and also as herbicides. 5
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:
10 W preferably represents hydrogen, C1-C6-alkyl, C2-C4-alkenyl, ethinyl, fluorine,
chlorine, bromine, C1-C4-halogenoalkyl or C1-C6-alkoxy.
X preferably represents fluorine, chlorine, bromine, C1-C6-alkyl, C1-C4-
halogenoalkyl, C1-C6-alkoxy, C2-C4-alkenyl, ethinyl, C1-C4-
15 halogenoalkoxy, cyano or in each case optionally halogen-, C1-C5-alkyl-, C1-
C6-alkoxy-, C1-C4-halogenoalkyl-, C1-C4-halogenoalkoxy-, nitro- or cyano-
substituted phenyl or benzyloxy.
Y preferably represents hydrogen, C1-C6-alkyl, fluorine, chlorine, bromine,
20 C1-C6-alkoxy, C2-C4-alkenyl, ethinyl or represents one of the radicals

V1 preferably represents hydrogen, halogen, C1-C12-alkyl, C1-C6-alkoxy,
C1-C6-alkylthio, C1-C4-halogenoalkyl, C1-C4-halogenoalkoxy, nitro, cyano
25 or represents phenyl, phenoxy, phenoxy-C1-C4-alkyl, phenyl-C1-C4-alkoxy,


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18
phenylthio-C1-C4-alkyl or phenyl-C1-C4-alkylthio, each of which is optionally mono- or polysubstituted by halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-halogenoalkyl, C1-C4-halogenoalkoxy, nitro or cyano.
5 V2 preferably represents hydrogen, fluorine, chlorine C1-C6-alkyl, C1-C6-alkoxy,
C1-C4-halogenoalkyl orC1-C4-halogenoalkoxy.
V3 preferably represents hydrogen, fluorine, chlorine, methyl or methoxy.
10 Z preferably represents hydrogen, fluorine, chlorine, bromine, C1-C6-alkyl, C1-
C4-halogenoalkyl, C1-C6-alkoxy, C1-C4-halogenoalkoxy or cyano, with the proviso that W, X and Z do not represent bromine, C2-C4-alkenyl and ethinyl if Y represents V1-, V2- and V3-substituted phenyl or hetaryl, and that at most two of the radicals W, X and Y may represent C2-C4-alkenyl and ethinyl, with
15 the proviso that none of the other radicals W, X, Y and Z may represent
bromine.
A preferably represents hydrogen or in each case optionally halogen-substituted C1-C12-alkyl, C3-C8-alkenyl, C1-C6-alkoxy-C1-C4alkyl, optionally
20 halogen-, C1-C4alkyl- or C1-C4-alkoxy-substituted C3-C8-cycloalkyl or C3-
C6-cycloalkyl-C1-C4-alkyl in which optionally one or two not directly adjacent ring members are replaced by oxygen and/or sulphur, or represents in each case optionally halogen-, C1-C6-alkyl-, C1-C6-halogenoalkyl-, C1-C6-alkoxy-, C1-C6-halogenoalkoxy-, cyano- or nitro-substituted phenyl, benzyl,
25 hetaryl having 5 or 6 ring members (for example furanyl, pyridyl, imidazolyl,
triazolyl, pyrazolyl, pyrimidyl, thiazolyl or thienyl) or hetaryl-C1-C4-alkyl having 5 or 6 ring members (for example pyridyl, pyrimidyl or thiazolyl).
B preferably represents hydrogen or C1-C6-alkyl.
30


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A, B and the carbon atom to which they are attached preferably represent saturated
or unsaturated " in which optionally one
ring member is replaced by oxygen or sulphur and which are optionally
mono- or disubstituted by
5 halogenoalkyl," halogen or phenyl, or
A and Q1 together preferably represent which is optionally mono-
or disubstituted by identical or different substituents ■ from the group consisting of
10
D
D
15
preferably represents hydrogen.
also preferably represents in each case optionally halogen-substituted ( alkenyl, optionally halogen-, C\~
or cycloalkyl or in which optionally one ring
member is replaced by oxygen or sulphur.
D and Q1 together preferably represent which is optionally mono-
20 or disubstituted by identical or different substituents from the group
consisting of
Q1 preferably represents hydrogen,
optionally fluorine-, chlorine-,
25 alkoxy-substituted in which optionally one methylene group
is replaced by oxygen or sulphur or optionally halogen-, alkoxy-, i cyano or nitro-
substituted phenyl, or
30 Q2 preferably represents hydrogen or


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20
Q1 and Q2 together with the carbon atom to which they are attached preferably represent optionally
substituted in which optionally one ring member is replaced
by oxygen or sulphur.
G preferably represents hydrogen (a) or represents one of the groups



in which
10 E represents a metal ion or an ammonium ion,
L represents oxygen or sulphur and
M represents oxygen or sulphur, 15
R.1 preferably represents in each case optionally halogen-substituted
alkyl,
alkyl, or optionally halogen-,
or in which optionally one or
20 more (preferably one or two) not directly adjacent ring members are replaced
by oxygen and/or sulphur,
represents optionally halogen-, cyano-, nitro-,
i
25 alkylsulphonyl-substituted phenyl,


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21
represents optionally halogen-, nitro-, cyano-,

alkyl,
5 represents optionally halogen-, or trifluoromethyl-substituted 5-
or 6-membered hetaryl (for example pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl),
represents optionally halogen- or
10 alkyl or
represents optionally halogen-, amino- or membered

15
R2 preferably represents in each case optionally halogen-substituted alkyl,

20 represents optionally halogen-,

represents in each case optionally halogen-, cyano-, nitro-,
substituted
25 phenyl or benzyl.
R3 preferably represents optionally halogen-substituted or
represents in each case optionally halogen-,
cyano- or nitro-substituted
30 phenyl or benzyl,


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22
R4 and R5 independently of one another preferably represent in each case optionally
halogen-substituted C1-C8-alkyl, C1-C8-alkoxy, C1-C8-alkylamino, di-(C1-
C8-alkyl)amino, C1-C8-alkylthio, C2-C8-alkenylthio, C3-C7-cycloalkylthio
or represent in each case optionally halogen-, nitro-, cyano-, C1-C4-alkoxy-,
5 C1-C4-halogenoalkoxy-, C1-C4-alkylthio-, C1-C4-halogenoalkylthio-, C1-
C4-alkyl- or C1-C4-halogenoalkyl-substituted phenyl, benzyl, phenoxy or phenylthio,
R6 and R7 independently of one another preferably represent hydrogen, represent in
10 each case optionally halogen-substituted C1-C8-alkyl, C3-C8-cycloalkyl,
C1-C8-alkoxy, C3-C8-alkenyl, Ci-Cg-alkoxy-C1-C8-alkyl, represent
optionally halogen-, C1-C8-halogenoalkyl-, C1-C8-alkyl- or C1-C8-alkoxy-
substituted phenyl, optionally halogen-, C1-C8-alkyl-, Ci-Cg-halogenoalkyl-
or C1-C8-alkoxy-substituted benzyl or together represent an optionally C1
15 C4alkyl-substituted C3-C6-alkylene radical in which optionally one carbon
atom is replaced by oxygen or sulphur.
In the radical definitions mentioned as being preferred, halogen, also as substituent,
such as, for example, in halogenoalkyl, represents fluorine, chlorine, bromine and
20 iodine, in particular fluorine and chlorine.
W particularly preferably represents hydrogen, C1-C4alkyl, C2-C3-alkenyl, ethinyl, fluorine, chlorine, bromine, trifluoromethyl or C1-C4alkoxy,
25 X particularly preferably represents fluorine, chlorine, bromine, C1i-C4-alkyl,
C1-C4-alkoxy, C2-C3-alkenyl, ethinyl, C1-C2-halogenoalkyl, C1-C2-halogenoalkoxy or cyano,
Y particularly preferably represents hydrogen, C1-C4alkyl, fluorine, chlorine,
30 bromine, C1-C4alkoxy, C2-C3-alkenyl, ethinyl, 2-thienyl, 3-thienyl or
represents the radical


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23



V1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, halogenoalkyl, nitro, cyano or phenyl,
V2 particularly preferably represents hydrogen, fluorine, chlorine

10
Z particularly preferably represents hydrogen, fluorine, chlorine, bromine,
with
the proviso that W, X and Z do not represent bromine, C2-C3-alkenyl and
ethinyl if Y represents V1- and V2-substituted phenyl, 2-thienyl or 3-thienyl,
15 and that only one of the radicals W, X and Y may represent C2-C3-alkenyl
and ethinyl, with the proviso that none of the other radicals W, X, Y and Z may represent bromine.
A particularly preferably represents hydrogen, in each case optionally fluorine-
20 substituted optionally fluorine-,
chlorine-, methyl,- ethyl- or methoxy-substituted
cycloalkyl-Cj-C2-alkyl, in which optionally one ring member is replaced by
oxygen or sulphur or in each case optionally fluorine-, chlorine-, bromine-,

25 halogenoalkoxy-substituted phenyl or benzyl.
B particularly preferably represents hydrogen or


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A, B and the carbon atom to which they are attached particularly preferably represent saturated in which optionally one ring member is
replaced by oxygen and which is optionally monosubstituted by trifluoromethyl or 5
A and Q1 together particularly preferably represent C3-C4-alkanediyl,
D particularly preferably represents hydrogen,
10 D particularly preferably also represents in each case optionally fluorine-
substituted cycloalkyl methylene group is replaced by oxygen.
15 D and Q1 together particularly preferably represent
Q1 particularly preferably represents hydrogen,
C2-alkyl or optionally methyl- or methoxy-substituted which optionally one methylene group is replaced by oxgen. 20
Q2 particularly preferably represents hydrogen, methyl or ethyl.
Q1 and Q2 together with the carbon to which they are attached particularly preferably represent optionally 25 in which optionally one ring member is replaced by oxygen.
G particularly preferably represents hydrogen (a) or represents one of the groups


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25

in which 5
E represents a metal ion or an ammonium ion,
L represents oxygen or sulphur and
10 M represents oxygen or sulphur.
Rl particularly preferably represents in each case optionally fluorine- or chlorine-
15
two not directly adjacent ring members are replaced by oxygen and/or sulphur,
represents optionally fluorine*, chlorine-, bromine-, cyano-, nitro-, C1-C4-
20 alkyl-, C1-C4-alkoxy-, trifluoromethyl- or trifluoromethoxy-substituted
phenyl,
represents in each case optionally fluorine-, chlorine-, bromine-, methyl-, ethyl- or trifluoromethyl-substituted pyridyl or thienyl,
25
R2 particularly preferably represents in each case optionally fluorine-substituted C1-C16-alkyl, C2-C16-alkenyl or C1-C4-alkoxy-C2-C4-alkyl,


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represents optionally methyl-, ethyl- or methoxy-substituted C3-C7-cycloalkyl or
represents in each case optionally fluorine-, chlorine-, bromine-, cyano-,
5 nitro-, C1-C4-alkyl-, C1-C3-alkoxy-, trifluoromethyl- or trifluoromethoxy-
substituted phenyl or benzyl.
R3 particularly preferably represents optionally fluorine-substituted C1-C6-alkyl
or represents in each case optionally fluorine-, chlorine-, bromine-, C1-C4-
10 alkyl-, C1-C4-alkoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-
substituted phenyl.
R4 particularly preferably represents C1-C6-alkyl, C1-C6-alkoxy, C1-C6
alkylamino, di-(C1-C6-alkyl)amino, C1-C6-alkylthio, or represents in each
15 case optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, C1-C3-alkoxy-,
trifluoromethoxy-, C1-C3-alkyl- or trifluoromethyl-substituted phenyl,
benzyl, phenoxy or phenylthio.
R5 particularly preferably represents C1-C4alkyl, C1-C4alkoxy or C1-C4-
20 alkylthio.
R6 particularly preferably represents hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl,
C1-C6-alkoxy, C3-C6-alkenyl, C1-C6-alkoxy-C1-C6-alkyl, represents
optionally fluorine-, chlorine-, bromine-, trifluoromethyl-, C1-C4-alkyl- or
25 C1-C4-alkoxy-substituted phenyl, represents optionally fluorine-, chlorine-,
bromine-, methyl-, ethyl-, trifluoromethyl- or methoxy-substituted benzyl.
R7 particularly preferably represents hydrogen, C1-C6-alkyl or C3-C6-alkenyl.


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R6 and R7 together particularly preferably represent an optionally methyl- or ethyl-substituted C4-C5-alkylene radical in which optionally one methylene group is replaced by oxygen or sulphur.
5 In the radical definitions mentioned as being particularly preferred, halogen, also as
substituent, such as, for example, in halogenoalkyl, represents fluorine, chlorine, bromine and iodine, in particular fluorine and chlorine, particularly preferably fluorine.
10 W very particularly preferably represents hydrogen, fluorine, chlorine, bromine,
methyl, ethyl, propyl or methoxy.
X very particularly preferably represents fluorine, chlorine, bromine, methyl,
ethyl, n-propyl, iso-propyl, methoxy, ethoxy, n-propoxy, trifluoromethyl,
15 difluoromethoxy, trifluoromethoxy or cyano (especially chlorine, bromine,
methyl, ethyl, n-propyl or trifluoromethyl).
Y very particularly preferably represents hydrogen, methyl, ethyl, propyl, iso-
propyl, fluorine, chlorine, bromine, methoxy, 2-thienyl, 3-thienyl or
20 represents the radical

V1 very particularly preferably represents hydrogen, fluorine, chlorine,
bromine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-
25 butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl or
trifluoromethoxy, cyano or phenyl.
V2 very particularly preferably represents hydrogen, fluorine, chlorine methyl, methoxy or trifluoromethyl.


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Z very particularly preferably represents hydrogen, fluorine, chlorine, bromine,
methyl, ethyl, methoxy or trifluoromethyl (especially hydrogen, fluorine,
chlorine, bromine or methyl), with the proviso that W, X and Z do not
5 represent bromine if Y represents V1- and V2-substituted phenyl, 2-thienyl or
3-thienyl.
A very particularly preferably represents hydrogen, methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, methoxymethyl, ethoxymethyl.
10
B very particularly preferably represents hydrogen, methyl or ethyl.
A, B and the carbon atom to which they are attached very particularly preferably
represent saturated C5-C6-cycloalkyl in which optionally one ring member is
15 replaced by oxygen and which is optionally monosubstituted by methyl, ethyl,
n-propyl, isopropyl, butyl, trifluoromethyl, methoxy, ethoxy, n-propoxy or n-
butoxy, or
A and Q1 together very particularly preferably represent C3-C4-alkanediyl, 20
D very particularly preferably represents hydrogen,
D very particularly preferably also represents allyl, 2-butenyl, methoxyethyl, ethoxyethyl, cyclopropyl, cyclopentyl or cyclohexyl. 25
D and Q1 together very particularly preferably represent C3-C4-alkanediyl.
Q1 very particularly preferably represents hydrogen, methyl, ethyl, propyl, iso¬propyl, cyclopropyl, cyclopentyl or cyclohexyl. 30
Q2 very particularly preferably represents hydrogen, methyl or ethyl.


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Q1 and Q2 together with the carbon to which they are attached very particularly
preferably represent optionally methyl-, ethyl-, propyl-, iso-propyl-, methoxy-,
ethoxy-, propoxy- or butoxy-substituted saturated C5-C6-cycloalkyl in which
5 optionally one ring member is replaced by oxygen.
G very particularly preferably represents hydrogen (a) or represents one of the groups

10

15

in which
E represents a metal ion or an ammonium ion,
L represents oxygen or sulphur and
M represents oxygen or sulphur,

20 R1 very particularly preferably represents in each case optionally fluorine- or
chlorine-substituted
. alkyl, or optionally fluorine-, chlorine-,
methyl-, ethyl- or methoxy-substituted in which optionally
one or two not directly adjacent ring members are replaced by oxygen and/or
25 sulphur,


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30

10

represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-, iso-propyl-, tert-butyl-, methoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl,
represents in each case optionally fluorine-, chlorine-, bromine- or methyl-substituted thienyl or pyridyl,
R2 very particularly preferably represents in each case optionally fluorine-substituted C1-C14-alkyl, C2-C14-alkenyl or C1-C4-alkoxy-C=-C3-alkyl,
represents optionally methyl-, ethyl- or methoxy-substituted C3-C6-cycloalkyl,

or represents in each case optionally fluorine-, chlorine-, cyano-, nitro-,
15 methyl-, ethyl-, iso-propyl-, tert-butyl-, methoxy-, trifluoromethyl- or
trifluoromethoxy-substituted phenyl or benzyl.
R3 very particularly preferably represents optionally fluorine-substituted methyl,
ethyl, n-propyl, iso-propyl or in each case optionally fluorine-, chlorine-,
20 bromine-, methyl-, tert-butyl-, methoxy-, trifluoromethyl-, trifluoromethoxy-,
cyano- or nitro-substituted phenyl.
R4 very particularly preferably represents C1-C4-alkyl, C1-C4-alkoxy, C1-C4-
alkylamino, di-( C1-C4-alkyl)amino, C1-C4-alkylthio or represents in each
25 case optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, C1-C2-alkoxy-,
trifluoromethoxy- or C1-C3-alkyl-substituted phenyl, phenoxy or phenylthio.
R5 very particularly preferably represents methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio. 30


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31
R6 very particularly preferably represents hydrogen, represents C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C3-C4-alkenyl, C1-C4-alkoxy- C1-C4-alkyl.
R7 very particularly preferably represents hydrogen, represents C1-C4-alkyl or
5 C3-C4-alkenyl.
R.6 and R7 together very particularly preferably represents a C5-C6-alkylene radical in which optionally one methylene group is replaced by oxygen or sulphur.
10 In the compounds of the formula (I) mentioned as being most preferred, the radicals
are as defined below:
W most preferably represents hydrogen, fluorine, chlorine, bromine, methyl or
ethyl, 15
X most preferably represents chlorine, bromine, methyl, ethyl, propyl or
trifluoromethyl,
Y most preferably represents hydrogen, chlorine, bromine, fluorine, methyl,
20 ethyl or the radical

V1 most preferably represents hydrogen, fluorine, chlorine, bromine,
25 methyl, tert-butyl, methoxy, trifluoromethyl or phenyl,
V2 most preferably represents. hydrogen, flourine, chlorine; -methyl, methoxy or trifluoromethyl,


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Z most preferably represents hydrogen, bromine, chlorine or methyl,
A most preferably represents methyl, ethyl or propyl,
5 B most preferably represents methyl or ethyl,
A, B and the carbon atom to which they are attached most preferably represent
saturated C5-C6-cycloalkyl in which optionally one ring member is replaced
by oxygen and which is optionally monosubstituted by methyl, ethyl,
10 methoxy, ethoxy, n-propoxy or n-butoxy.
D most preferably represents hydrogen,
D most preferably also represents cyclopropyl, cyclopentyl or cyclohexyl, 15
Q1 and Q2 most preferably represent hydrogen,
D and Q1 together most preferably represent butanediyl,
20 G most preferably represents hydrogen (a) or represents one of the groups

25 Rl most preferably represents C1-C8-alkyl, C2-C4~alkenyl, methoxymethyl,
ethoxymethyl, ethylthiomethyl or optionally fluorine-, chlorine-, methyl-, ethyl- or methoxy-substituted cyclopropyl, cyclopentyl or cyclohexyl,


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represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-, iso-propyl-, tert-butyl-, methoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl, 5
represents in each case optionally chlorine- or methyl-substituted thienyl or pyridyl,
R2 most preferably represents in each case optionally fluorine-substituted C1-C8-
10 alkyl, C2-C4-alkenyl or methoxyethyl, ethoxyethyl, propoxyethyl, iso-
propoxyethyl, cyclopentyl or cyclohexyl,
or represents in each case optionally fluorine-, chlorine-, cyano-, nitro-,
methyl-, ethyl-, iso-propyl-, tert-butyl-, methoxy-, trifluoromethyl- or
15 trifluoromethoxy-substituted phenyl or benzyl.
R3 most preferably represents methyl,
R6 and R7 together most preferably represent a C6-alkylene radical in which
20 optionally one methylene group is replaced by oxygen,
or else
W most preferably represents hydrogen, fluorine, chlorine, bromine, methyl or
25 ethyl,
X most preferably represents chlorine, bromine, methyl, ethyl, propyl or trifluoromethyl,
30 Y most preferably represents hydrogen, methyl, ethyl, fluorine, chlorine,
bromine or represents the radical


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V1 most preferably represents hydrogen, fluorine, chlorine, bromine,
5 methyl, tert-butyl, methoxy, trifluoromethyl or phenyl,
V2 most preferably represents hydrogen, fluorine, chlorine methyl, methoxy or trifluoromethyl,
10 Z most preferably represents hydrogen, chlorine, bromine or methyl,
A and B most preferably represent hydrogen,
D most preferably represents hydrogen, methyl, ethyl propyl, iso-propyl,
15 cyclopropyl, cyclopentyl cyclohexyl,
D and Q1 together most preferably represent butanediyl,
Q1 most preferably represents methyl, ethyl or propyl, 20
Q2 most preferably represents methyl; if D and Q1 together represent butanediyl, Q2 may also represent hydrogen,
Q1 and Q2 together with the carbon to which they are attached most preferably
25 represent optionally methyl-, ethyl-, methoxy-, ethoxy-, propoxy- or butoxy-
substituted C5-C6-cycloalkyl in which optionally one ring member is replaced by oxygen,
G most preferably represents hydrogen (a) or represents one of the groups

Le A 34 338-Foreign Countries

in which M represents oxygen or sulphur,
R1 most preferably represents C1-C8-alkyl, C2-C4-alkenyr, methoxymethyl,
5 ethoxymethyl, ethylthiomethyl or optionally fluorine-, chlorine-, methyl-,
ethyl- or methoxy-substituted cyclopropyl, cyclopentyl or cyclohexyl,
represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-,
ethyl-, iso-propyl-, tert-butyl-, methoxy-, trifluoromethyl- or
10 trifluoromethoxy-substituted phenyl,
represents in each case optionally chlorine- or methyl-substituted thienyl or pyridyl,
15 R2 most preferably represents in each case optionally fluorine-substituted C1-C8-
alkyl, C2-C4-alkenyl or methoxyethyl, ethoxyethyl, propoxyethyl, iso-propoxyethyl, cyclopentyl or cyclohexyl,
or represents in each case optionally fluorine-, chlorine-, cyano-, nitro-,
20 methyl-, ethyl-, iso-propyl-, tert-butyl-, methoxy-, trifluoromethyl- or
trifluoromethoxy-substituted phenyl or benzyl,
R3 most preferably represents methyl.
25 R6 and R7 together most preferably represent a C6-alkylene radical in which
optionally one methylene group is replaced by oxygen.


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The abovementioned general or preferred radical definitions or illustrations can be combined with one another as desired, i.e. including combinations between the respective ranges and preferred ranges. They apply both to the end products and, correspondingly, to precursors and intermediates. 5
Preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being preferred (preferable).
Particular preference according to the invention is given to the compounds of the
10 formula (I) which contain a combination of the meanings listed above as being
particularly preferred.
Very particular preference according to the invention is given to the compounds of
the formula (I) which contain a combination of the meanings listed above as being
15 very particularly preferred.
Most preference is given to compounds of the formula (I) in which G represents hydrogen.
20 Most preference is given to compounds of the formula (I) in which D represents
hydrogen.
Furthermore, most preference is given to compounds of the formula (I) in which D represents optionally substituted alkenyl, alkinyl, alkoxyalkyl or cycloalkyl. 25
Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, can in each case be straight-chain or branched as far as this is possible, also in combination with heteroatoms, such as, for example in alkoxy.


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Unless indicated otherwise, optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitution, the substituents can be identical or different.
Using according to process (A) ethyl N-[(2,3,4,6-tetramethyl)-phenylacetyl]-l-aminomethyl-cyclohexane-carboxylate as starting material, the course of the process according to the invention can be represented by the following reaction scheme;



Using according to process (By) 3-[(2-chloro-4-bromo-6-methyl)-phenyl]-6,6-dimethyl-piperidine-2,4-dione and 4-chlorophenylboronic acid as starting materials, the course of the reaction can be represented by the following scheme:


15

20

Using according to process (Coc) 3-[(2,4-dichloro-6-methyl)-phenyl]-6,6-dimethylpiperidine-2,4-dione and pivaloyl chloride as starting materials, the course of the process according to the invention can be represented by the following reaction scheme:

3S

Le A 34 338-Foreign Countries
-38



Using according to process (Cp) 3-[(4-bromo-2-chloro-6-ethyl)-phenyl]-6,6-dimethyl-piperidine-2,4-dione and acetic anhydride as starting materials, the course of the process according to the invention can be represented by the following reaction scheme:



10 Using according to process (D) 3-[(2-chloro-6-ethyl-4-phenyl)-phenyI]-5,5-
dimethylpiperidine-2,4-dione and ethoxyethyl chloroformate as starting materials, the course of the process according to the invention can be represented by the following reaction scheme:

15


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Using according to process (E) 3-[2,4,6-trichloro-phenyl]-6,6-dimethyl-piperidine-2,4-dione and methyl chloromonothioformate as starting materials, the course of the reaction can be represented as follows:



Using according to process (F) 3-(2,4-dichloro-6-methyl-phenyl)-6,6-dimethyl-piperidine-2,4-dione and methanesulphonyl chloride as starting materials, the course of the reaction can be represented by the following reaction scheme:
10




15

Using according to process (G) 2-(2-methyl-5-bromo-phenyl)-6,6-dimethyUpyridine-2,4-dione and 2,2,2-trifluoroethyl methanethiophosphonyl chloride as starting materials, the course of the reaction can be represented by the following reaction scheme:




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-40
Using according to process (H) 3-(2,4-dichloro-phenyl)-6,6-dimethyl-piperidine-2,4-dione and NaOH as components, the course of the process according to the invention can be represented by the following reaction scheme:



Using according to process (la) 3-(2,4-dichloro-6-methyl-phenyl)-6,6-dimethyl-piperidine-2,4-dione and ethyl isocyanate as starting materials, the course of the reaction can be represented by the following reaction scheme:
10




15

Using according to process (IB) 3-(2-chloro-4-bromo-phenyl)-6,6-dimethyI-piperidine-2,4-dione and dimethylcarbamoyl chloride as starting materials, the course of the reaction can be represented by the following scheme:




The compounds of the formula (II)



Le A 34 338-Foreign Countries
-41



in which

5

A, B, D, Q1, Q2, W, X, Y, Z and R8 are each as defined above,
required as starting materials for the process (A) according to the invention are novel, except for the compounds


10
in which
A and B each represent methyl or
15 A and B represent-(CH2)5-and
R8 represents alkyl.
The acylamino acid esters of the formula (II) are obtained, for example, when amino
20 acid derivatives of the formula (XVI)


Le A 34 338-Foreign Countries
42



in which

5

A, B, Q1,Q2, R8 and D are each as defined above,
axe acylated with substituted phenylacetyl halides of the formula (XVII)





in which
10
W, X, Y and Z are each as defined above and
Hal represents chlorine or bromine,
15 (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6, 341-5,1968)
or when acylamino acids of the formula (XVIII)



Le A 34 338-Foreisn Countries
43
in which
A, B, D, Q1, Q2, W, X, Y and Z are each as defined above,
are esterified (Chem. Ind. (London) 1568 (1968)).
The compounds of the formula (XVHI)



10 in which

15

A, B, D, Q1, Q2, W, X, Y and Z are each as defined above, are novel.
The compounds of the formula (XVIII) are obtained when amino acids of the formula (XIX)







20 in which
A, B, Q1, Q2 and D are each as defined above,

_

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44
are acylated with substituted phenylacetyl halides of the formula (XVII)

in which
W, X, Y and Z are each as defined above and
Hal represents chlorine or bromine,
for example according to Schotten-Baumann (Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, p. 505).
The compounds of the formula (XVII) are known. They can be prepared by processes known in principle (see, for example, H. Henecka, Houben-Weyl, Methoden der Organischen Chemie [Methods of organic chemistry], Vol. 8, p. 467-469 (1952)).
The compounds of the formula (XVII) are obtained, for example, by reacting substituted phenylacetic acids of the formula (XX)

in which
W, X, Y and Z are each as defined above,


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with halogenating agents (for example thionyl chloride, thionyl bromide, oxalyl
chloride, phosgene, phosphorus trichloride, phosphorus tribromide or phosphorus
pentachloride), if appropriate in the presence of a diluent (for example optionally
5 chlorinated aliphatic or aromatic hydrocarbons, such as toluene or methylene
chloride) at temperatures of from -20°C to 150°C, preferably from -10°C to 100°C.
Some of the compounds of the formulae (XVI) and (XIX) are known, and/or they can
be prepared by known processes (see, for example, T. Suzuki et al., Synthetic
10 Commun. 28,701 (1998), R. Graf, Justus Liebigs Ann. Chem. 661,111 (1963)).
Furthermore, the starting materials of the formula (II)



15 in which

20

A, B, D, Q1, Q2, W, X, Y, Z and R8 are each as defined above,
used in the above process (A)
can be prepared by reacting aminonitriles of the formula (XXI)



Le A 34 338-Foreign Countries
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5

in which
A, B, Q1, Q2 and D are each as defined above,
with substituted phenylacetyl halides of the formula (XVII)





in which

10

W, X, Y, Z and Hal are each as defined above, to give compounds of the formula (XXII)


15
in which
A, B, D, Q1, Q2, W, X, Y and Z are each as defined above,
20 and then subjecting these to an acid alcoholysis.


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The compounds of the formula (XXII) are likewise novel.
Some of the aminonitriles of the formula (XXI) are known, and/or they can be
5 prepared by known processes (T. Suzuki et al., Chem. Pharm. Bull. 46,1116 (1998)).
Some of the silylacetylenes of the formula (III) required for carrying out the process
B(cx) are commercially available, or they can be prepared by generally known
processes. Some of the vinylstannanes of the formula (IV) required for carrying out
10 the process B(|3) are also commercially available, or they can be prepared by known
processes.
Some of the boronic acids of the formula (V)

15
in which
Y represents optionally substituted phenyl or hetaryl,
20 required for carrying out the process B(y) are commercially available, or they can be
prepared in a simple manner by generally known processes.
The acid halides of the formula (VI), carboxylic anhydrides of the formula (VII),
chloroformic esters or chloroformic thioesters of the formula (VIII),
25 chloromonothioformic esters or chlorodithioformic esters of the formula (IX),
sulphonyl chlorides of the formula (X), phosphorus compounds of the formula (XI) and metal hydroxides, metal alkoxides or amines of the formulae (XII) and (XHI) and isocyanates of the formula (XIV) and carbamoyl chlorides of the formula (XV) furthermore required as starting materials for carrying out the processes (C), (D), (E),


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(F), (G), (H) and (I) according to the invention are generally known compounds of organic or inorganic chemistry.
The process (A) is characterized in that compounds of the formula (II) in which A, B,
5 D, Ql, Q2, W, X, Y, Z and R8 are each as defined above are subjected to an
intramolecular condensation in the presence of the base.
Suitable diluents for the process (A) according to the invention are all inert organic solvents. Preference is given to using hydrocarbons, such as toluene and xylene,
10 furthermore ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl
ether and diglycol dimethyl ether, moreover polar solvents, such as dimethyl sulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone, and also alcohols, such as methanol, ethanol, propanol, iso-propanol, butanol, iso-butanol and tert-butanol.
15
Suitable bases (deprotonating agents) for carrying out the process (A) according to invention are all customary proton acceptors. Preference is given to using alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium
20 carbonate, potassium carbonate and calcium carbonate, which can also be employed
in the presence of phase-transfer catalysts, such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl(C8-C10)ammomiim chloride) or TDA 1 (= tris-(methoxyethoxyethyl)-amine). Alkali metals such as sodium and potassium can also be used. Furthermore,
25 alkali metal and alkaline earth metal amides and hydrides, such as sodium amide,
sodium hydride and calcium hydride and additionally also alkali metal alkoxides, such as sodium methoxide, sodium ethoxide and potassium tert-butoxide can be employed.


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When carrying out process (A) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between -50°C and 200°C, preferably between -20°C and 150°C.
5 The process (A) according to the invention is generally carried out under atmospheric
pressure.
When carrying out the process (A) according to the invention, the reaction
components of the formula (II) and the deprotonating bases are generally employed in
10 approximately double-equimolar amounts. However, it is also possible to use a larger
excess (up to 3 mol) of one component or the other.
Suitable catalysts for carrying out the process B (a) to B (y) according to the
invention are palladium(O) complexes. Use is made, for example, of tetrakis-
15 (triphenylphosphine)palladium. Also suitable are palladium(II) compounds, such as
bis(triphenylphosphine)palladium(II) chloride.
Suitable acid acceptors for carrying out the processes B (a) and B (Y) according to the invention are inorganic or organic bases. These preferably include alkaline earth
20 metal or alkali metal hydroxides, acetates, carbonates or bicarbonates, such as, for
example, sodium hydroxide, potassium hydroxide, barium hydroxide or ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate or ammonium acetate, sodium carbonate, potassium carbonate or ammonium carbonate, sodium bicarbonate or potassium bicarbonate, alkali metal fluorides, such as, for example, potassium
25 fluoride and caesium fluoride, and also tertiary amines, such as trimethylamine,
triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
30


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Suitable diluents for carrying out the process B (y) according to the invention are
water, organic solvents and any mixtures thereof. Organic solvents which may be
mentioned in an exemplary manner for processes B (a) to B (y) are: aliphatic,
alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane,
5 heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline;
halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene,
methylene chloride, chloroform, carbon tetrachloride, dichloroethane, trichloroethane
or tetrachloroethylene; ethers, such as diethyl ether, diisopropyl ether, methyl tert-
butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,
10 1,2-diethoxyethane, diethylene glycol dimethyl ether or anisol; alcohols, such as
methanol, ethanol, n- or iso-propanol, n-, iso-, sec or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether; diethylene glycol monoethyl ether; water.
15 When carrying out the process (B) according to the invention, the reaction
temperature can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between 0°C and +180°C, preferably between +50°C and +150°C.
20 When carrying out the process B (a), silylacetylenes of the formula (III) and
compounds of the formulae (I-a) to (I-g) are employed in a molar ratio of from 1:1 to 10:1, preferably from 1:1 to 3:1. When carrying out the process B((3), vinylstannanes of the formula (IV) and compounds of the formulae (I-a) to (I-g) are employed in a molar ratio of from 1:1 to 10:1, preferably from 1:1 to 3:1.
25
When carrying out the process B (y) according to the invention, the boronic acid of the formula (V) and the compounds of the formulae (I-a) to (I-g) are employed in a molar ratio of from 1:1 to 3:1, preferably from 1:1 to 2:1.


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The catalyst is generally employed in an amount from 0.005 to 0.5 mol, preferably 0.01 mol to 0.1 mol, per mole of the compounds (I-l-a) to (I-l-g). The base is generally employed in excess.
5 The process (C-a) is characterized in that compounds of the formula (I-a) are in each
case reacted with carbonyl halides of the formula (VI), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
Suitable diluents for the process (C-a) according to the invention are all solvents
10 which are inert towards the acid halides. Preference is given to using hydrocarbons,
such as benzine, benzene, toluene, xylene and tetraline, furthermore halogenated
hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride,
chlorobenzene and o-dichlorobenzene, moreover ketones, such as acetone and methyl
isopropyl ketone, furthermore ethers, such as diethyl ether, tetrahydrofuran and
15 dioxane, additionally carboxylic esters, such ethyl acetate, nitriles, such as
acetonitrile, and also strongly polar solvents, such as demethylformamide, dimethyl sulphoxide and sulpholane. The hydrolytic stability of the acid halide permitting, the reaction can also be carried out in the presence of water.
20 Suitable acid binders for the reaction according to the process (C-a) according to the
invention are all customary acid acceptors. Preference is given to using tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hiinig base and N,N-dimethyl-aniline, further alkaline earth metal oxides, such as magnesium oxide and
25 calcium oxide, moreover alkali metal and alkaline earth metal carbonates, such as
sodium carbonate, potassium carbonate and calcium carbonate, and also alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide.
The reaction temperatures in the process (C-a) according to the invention can be
30 varied within a relatively wide range. In general, the reaction is carried out at
temperatures between -20°C and +150°C, preferably between 0°C and 100°C.
-^

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When carrying out the process (C-a) according to the invention, the starting materials
of the formula (I-a) and the carbonyl halide of the formula (VI) are generally in each
case employed in approximately equivalent amounts. However, it is also possible to
5 employ a relatively large excess (up to 5 mol) of the carbonyl halide. Work-up is
carried out by customary methods.
The process (C-P) is characterized in that compounds of the formulae (I-a) are
reacted with carboxylic anhydrides of the formula (VII), if appropriate in the
10 presence of a diluent and if appropriate in the presence of an acid binder.
Preferred diluents for the process (C-P) according to the invention are those diluents which are also preferred when acid halides are used. Otherwise, it is also possible for a carboxylic anhydride employed in excess to act simultaneously as a diluent. 15
In the process (C-p), acid binders which are added, if appropriate, are preferably those acid binders which are also preferred when acid halides are used.
In the process (C-p) according to the invention, the reaction temperatures can be
20 varied within a relatively wide range. In general, the reaction is carried out at
temperatures between -20°C and +150°C, preferably between 0°C and 100°C.
When carrying out the process (C-p) according to the invention, the starting materials
of the formula (I-a) and the carboxylic anhydride of the formula (VII) are generally
25 each employed in approximately equivalent amounts. However, it is also possible to
use a relatively large excess (up to 5 mol) of the carboxylic anhydride. Work-up is carried out by customary methods.
In general, the adopted procedure is to remove diluent and excess carboxylic
30 anhydride and also the carboxylic acid formed by distillation or by washing with an
organic solvent or with water.


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-53-
The process (D) is characterized in that compounds of the formula (I-a) are in each
case reacted with chloroformic esters or chloroformic thioesters of the formula (VIE),
if appropriate in the presence of a diluent and if appropriate in the presence of an acid
5 binder.
Suitable acid binders for the reaction according to the process (D) according to the invention are all customary acid acceptors. Preference is given to using tertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBA, Hiinig base and N,N-
10 dimethyl-aniline, furthermore alkaline earth metal oxides, such as magnesium oxide
and calcium oxide, moreover alkali metal carbonates and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and also alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide.
15
Suitable diluents for the process (D) according to the invention are all solvents which are inert towards the chloroformic esters or chloroformic thioesters. Preference is given to using hydrocarbons, such as benzine, benzene, toluene, xylene and tetraline, furthermore halogenated hydrocarbons, such as methylene chloride, chloroform,
20 carbon tetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones, such
as acetone and methyl isopropyl ketone, furthermore ethers, such as diethyl ether, tetrahydrofuran and dioxane, additionally carboxylic esters, such as ethyl acetate, nitriles, such as acetonitrile, and also strongly polar solvents, such as dimethylformamide, dimethyl sulphoxide and sulpholane.
25
When carrying out the process (D) according to the invention, the reaction temperatures can be varied within a relatively wide range. If the reaction is carried out in the presence of a diluent and an acid binder, the reaction temperatures are generally between -20°C and +100°C, preferably between 0°C and 50°C.


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-54-
The process (D) according to the invention is generally carried out under atmospheric pressure.
When carrying out the process (D) according to the invention, the starting materials
5 of the formula (I-a) and the appropriate chloroformic ester or chloroformic thioester
of the formula (VIII) are generally in each case employed in approximately
equivalent amounts. However, it is also possible to employ a relatively large excess
(up to 2 mol) of one component or the other. Work-up is carried out by customary
methods. In general, precipitated salts are removed and the reaction mixture that
10 remains is concentrated by stripping the diluent.
The process (E) according to the invention is characterized in that compounds of the formula (I-a) are in each case reacted with compounds of the formula (IX) in the presence of a diluent and, if appropriate, in the presence of an acid binder. 15
In the preparation process (E), approximately 1 mol of chloromonothioformic ester or chlorodithioformic ester of the formula (IX) is reacted per mole of starting material of the formula (I-a), at from 0 to 120°C, preferably at from 20 to 60°C.
20 Suitable diluents which are added, if appropriate, are all inert polar organic solvents,
such as nitriles, ethers, esters, amides, sulphones, sulphoxides, but also halogenoalkanes.
Preference is given to using acetonitrile, ethyl acetate, dimethyl sulphoxide,
25 tetrahydrofuran, dimethylforrnamide or methylene chloride.
If, in a preferred embodiment, the enolate salt of the compound (I-a) is prepared by addition of strong deprotonating agents, such as, for example, sodium hydride or potassium tert-butoxide, it is not necessary to add further acid binders. 30


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If acid binders are employed, these are customary inorganic or organic bases, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine.
5 The reaction can be carried out at atmospheric pressure or under elevated pressure
and is preferably carried out at atmospheric pressure. Work-up is carried out by customary methods.
The process (F) according to the invention is characterized in that compounds of the
10 formula (I-a) are in each case reacted with sulphonyl chlorides of the formula (X), if
appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
In the preparation process (F), approximately 1 mol of sulphonyl chloride of the
15 formula (X) is reacted per mole of starting material of the formula (I-a), at from -20
to 150°C, preferably at from 20 to 70°C.
Suitable diluents which are added, if appropriate, are all inert polar organic solvents,
such as esters, ethers, amides, nitriles, sulphones, sulphoxides or halogenated
20 hydrocarbons, such as methylene chloride.
Preference is given to using acetonitrile, ethyl acetate, dimethyl sulphoxide, tetrahydrofuran, dimethylformamide, methylene chloride.
25 If, in a preferred embodiment, the enolate salt of the compound (I-a) is prepared by
addition of strong deprotonating agents (such as, for example, sodium hydride or potassium tert-butoxide), it is not necessary to add further acid binders.
If acid binders are employed, these are customary inorganic or organic bases, for
30 example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine,
triethylamine.


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The reaction can be carried out at atmospheric pressure or under elevated pressure and is preferably carried out at atmospheric pressure. Work-up is carried out by customary methods 5
The process (G) according to the invention is characterized in that compounds of the formula (I-a) are in each case reacted with phosphorus compounds of the formula (XI), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
10
In the preparation process (G), 1 to 2, preferably 1 to 1.3 mol of the phosphorus compound of the formula (XI) are reacted per mole of the compound (I-a) at temperatures between -40°C and 150°C, preferably between -10 and 110°C, to give compounds of the formula (I-e).
15
Suitable solvents which are added, if appropriate, are all inert polar organic solvents, such as ethers, amides, nitriles, alcohols, sulphides, sulphones, sulphoxides, etc.
Preference is given to using acetonitrile, dimethyl sulphoxide, tetrahydrofuran,
20 dimethylformamide, methylene chloride.
Suitable acid binders which are added, if appropriate, are customary inorganic or organic bases, such as hydroxides, carbonates or amines. Examples include sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine.
25
The reaction can be carried out at atmospheric pressure or under elevated pressure and is preferably carried out under atmospheric pressure. Work-up is carried out by customary methods of organic chemistry. The resulting end products are preferably purified by crystallization, chromatographic purification or by so-called "incipient
30 distillation", i.e. removal of the volatile components under reduced pressure.


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The process (H) is characterized in that compounds of the formula (I-a) are reacted with metal hydroxides or metal alkoxides of the formula (XII) or amines of the formula (XIII), if appropriate in the presence of a diluent.
5 Preferred diluents for the process (H) according to the invention are ethers, such as
tetrahydrofuran, dioxane, diethyl ether or else alcohols, such as methanol, ethanol, isopropanol, but also water.
The process (H) according to the invention is generally carried out under atmospheric
10 pressure.
The reaction temperatures are generally between -20°C and 100°C, preferably between 0°C and 50°C.
15 The process (I) according to the invention is characterized in that compounds of the
formula (I-a) are in each case reacted with (I-a) compounds of the formula (XIV), if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst, or (I-|3) with compounds of the formula (XV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
20
In the preparation process (I-a), approximately 1 mol of isocyanate of the formula (XIV) is reacted per mole of starting material of the formula (I-a), at from 0 to 100°C, preferably at from 20 to 50°C.
25 Suitable diluents which are added, if appropriate, are all inert organic solvents, such
as nitriles, esters, ethers, amides, sulphones, sulphoxides.
If appropriate, catalysts may be added to accelerate the reaction. Very
advantageously, the catalysts which are employed are organotin compounds, such as,
30 for example, dibutyltin dilaurate. The reaction is preferably carried out at
atmospheric pressure.


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In the preparation process (I-P), approximately 1 mol of carbamoyl chloride of the formula (XV) is reacted per mole of starting material of the formula (I-a), at from -20 to 150°C, preferably at from 0 to 70°C. 5
Suitable diluents which are added, if appropriate, are all inert polar organic solvents, such as nitriles, esters, ethers, amides, sulphones, sulphoxides or halogenated hydrocarbons.
10 Preference is given to using acetonitrile, ethylene acetate, dimethyl sulphoxide,
tetrahydrofuran, dimethylformamide or methylene chloride.
If, in a preferred embodiment, the enolate salt of the compound (la) is prepared by
addition of strong deprotonating agents (such as, for example, sodium hydride or
15 potassium tert-butoxide), it is not necessary to add further acid binders.
If acid binders are employed, these are customary inorganic or organic bases, for example sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine. 20
The reaction can be carried out at atmospheric pressure or under elevated pressure and is preferably carried out at atmospheric pressure. Work-up is carried out by customary methods.
25 The active compounds are suitable for controlling animal pests, in particular insects,
arachnids and nematodes found in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector, and they are tolerated well by plants and have favourable homeotherm toxicity. They are preferably employed as crop protection agents. They are active against normally sensitive and resistant species,
30 and against all or individual developmental stages. The abovementioned pests
include:


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From the order of the Isopoda, for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
5 From the order of the Diplopoda, for example, Blaniulus guttulatus.
From the order of the Chilopoda, for example, Geophilus carpophagus, Scutigera spp.
10 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. 15
From the order of the Orthoptera, for example, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
From the order of the Blattaria, for example, Blatta orientalis, Periplaneta americana,
20 Leucophaea maderae, Blattella germanica.
From the order of the Dermaptera, for example, Forficula auricularia.
From the order of the Isoptera, for example, Reticulitermes spp. 25
From the order of the Phthiraptera, for example, Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips
30 tabaci, Thrips palmi, Frankliniella occidentalis.


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From the order of the Heteroptera, for example, Eurygaster spp„ Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci,
5 Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus
ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon
humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix
cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata
10 lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.,
15 Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp.,
Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, 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,
20 Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,
Cnaphalocerus spp., Oulema oryzae.
From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus,
25 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 spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,
30 Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio


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molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp.,
5 Lasius spp., Monomorium pharaonis, Vespa spp.
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.,
10 Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio
hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.
From the order of the Siphonaptera, for example, Xenopsylla cheopis, Ceratophyllus
15 spp.
From the class of the Arachnida, for example, Scorpio maurus, Latrodectus mactans,
Acarus siro, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis,
Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp.,
20 Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,
Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
The plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus
25 similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera
spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.
At certain concentrations or application rates, the compounds according to the
30 invention can, if appropriate, also be employed as herbicides and microbicides, for


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example as fungicides, antimycotics and bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
The active compounds can be converted into the customary formulations such as
5 solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble
powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric materials.
These formulations are produced in a known manner, for example by mixing the
10 active compounds with extenders, that is, liquid solvents and/or solid carriers,
optionally with the use of surfactants, that is, emulsifiers and/or dispersants, and/or foam formers.
If the extender used is water, it is also possible, for example, to use organic solvents
15 as cosolvents. The following are essentially suitable as liquid solvents: 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, mineral and vegetable oils, alcohols such as butanol or glycol
20 and 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, or else water.
Suitable solid carriers are:
25
for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as highly-disperse silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as
30 calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of
inorganic and organic meals, and granules of organic material such as sawdust,


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coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam
formers are: for example nonionic and anionic emulsifiers such as polyoxyethylene
fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl
polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein
5 hydrolysates; suitable dispersants are: for example lignin-sulphite waste liquors and
methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the
form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and
10 polyvinyl acetate, or else 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,
15 titanium oxide and Prussian Blue, and organic colorants such as alizarin colorants,
azo colorants and metal phthalocyanine colorants, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95% by weight of active
20 compound, preferably between 0.5 and 90%.
The active compound according to the invention can be present in its commercially
available formulations and in the use forms, prepared from these formulations, as a
mixture with other active compounds, such as insecticides, attractants, sterilants,
25 bactericides, acaricides, nematicides, fungicides, growth-regulating substances or
herbicides. The insecticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and substances produced by microorganisms.
30 Examples of particularly advantageous mixing components are the following:


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Fungjcides
aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl, bialaphos,
5 binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate,
buthiobate,
calcium polysulphide, capsimycin, captafol, capian, carbendazim, carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyproconazole,
10 cyprodinil, cyprofuram,
debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon,
15 edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,
famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide, fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,
20 fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis,
furmecyclox, guazatine,
hexachlorobenzene, hexaconazole, hymexazole, imazalil, imibenconazole, iminoctadine, iminoctadine albesilate, iminoctadine
25 triacetate, iodocarb, ipconazole, iprobenfos (IBP), iprodione, irumamycin,
isoprothiolane, isovaledione,
kasugamycin, kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture,


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mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil, metalaxyl,
metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax,
mildiomycin, myclobutanil, myclozolin,
nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,
5 ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,
paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,
10 quinconazole, quintozene (PCNB),
sulphur and sulphur preparations,
tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole, thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram, tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, trichlamide, tricyclazole,
15 tridemorph, triflumizole, triforine, triticonazole,
uniconazole,
validamycin A, vinclozolin, viniconazole, zarilamide, zineb, ziram and also Dagger G,
20 OK-8705,
OK-8801,
α-(l,l-dimethylethyl)-β-(2-phenoxyethyl)-lH-l,2,4-triazole-l-ethanol, α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-lH-l,2,4-triazole-l-ethanol, α-(2,4-dichlorophenyl)-p-methoxy-α-methyl-1H-1,2,4-triazole-1 -ethanol,
25 α-(5-methyl-l,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-lH-l,2,4-
triazole-1 -ethanol,
(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(lH-l,2,4-triazol-l-yl)-3-octanone, (E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetarnide, 1-isopropyl {2-methyl-l-[[[l-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-
30 carbamate,
l-(2,4-dichlorophenyl)-2-(lH-l,2,4-triazol-l-yl)-ethanone O-(phenylmethyl)-oxime,


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1 -(2-methyl-1 -naphthalenyl)- lH-pyrrole-2,5-dione,
l-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,
l-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,
l-[[2-(2,4-dich]orophenyl)-l,3-dioxolan-2-yl]-methyl]-lH-imidazole,
5 l-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-lH-l,2,4-triazole,
l-[l-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-lH-imidazole,
l-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,
2",6"-dibromo-2-methy]-4"-trifluoromethoxy-4,-trifluoro-methyl-l,3-thiazole-5-
carboxanilide,
10 2,2-dichloro-N-[l-(4-chIorophenyl)-ethyl]-l-ethyl-3-methyl-cyclopropane-
carboxamide,
2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,
2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,
2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,
15 2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,
2-[(l-methylethyl)-sulphonyl]-5-(trichloromethy])"l,3,4-thiadiazole,
2-[[6-deoxy-4-0-(4-0-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-
methoxy-lH-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,
2-aminobutane,
20 2-bromo-2-(bromomethyl)-pentanedinitrile,
2-chloro-N-(2,3-dihydro-l,l,3-trimethyl-lH-inden-4-yl)-3-pyridinecarboxamide,
2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,
2-phenylphenol (OPP),
3,4-dichloro-l-[4-(difluoromethoxy)-phenyl]-lH-pyrrole-2,5-dione,
25 3,5-dichloro-N-[cyano[(l-methyl-2-propinyl)-oxy]-methyl]-benzamide,
3-( 1,1 -dimethylpropyl-1 -oxo-1 H-indene-2-carbonitrile,
3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,
4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-lH-imidazole-l-sulphonamide,
4-methyl-tetrazolo[l,5-a]quinazolin-5(4H)-one,
30 8-(l,l-dimethylethyl)-N-ethyl-N-propyl-l,4-dioxaspiro[4.5]decane-2-methanamine,
8-hydroxyquinoline sulphate,


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9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylichydrazide,
bis-(l-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,
cis-1 -(4-chlorophenyl)-2-( 1H-1,2,4-triazol-1 -yl)-cycloheptanol,
cis-4-[3-[4-(l,l-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine-
5 hydrochloride,
ethyl [(4-chlorophenyl)-azo]-cyanoacetate,
potassium hydrogen carbonate,
methanetetrathiol sodium salt,
methyl l-(2,3-dihydro-2,2-dimethyl-lH-inden-l-yl)-lH-imidazole-5-carboxylate,
10 methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,
methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate, N-(2,3-dichloro-4-hydroxyphenyl)-l-methyl-cyclohexanecarboxamide, N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide, N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,
15 N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,
N-(4-cyclohexylphenyl)-l,4,5,6-tetrahydro-2-pyrimidineamine, N-(4-hexylphenyl)-l,4,5,6-tetrahydro-2-pyrimidineamine, N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide, N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide,
20 N-[2,2,2-trichloro-l-[(chloroacetyl)-amino]-ethyl]-benzamide,
N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N"-methoxy-methanimidamide, N-formyl-N-hydroxy-DL-alanine sodium salt,
0,0-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate, O-methyl S-phenyl phenylpropylphosphoramidothioate,
25 S-methyl l,2,3-benzothiadiazole-7-carbothioate,
spiro[2H]-l-benzopyran-2,l"(3"H)-isobenzofuran]-3"-one,
Bactericides
bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin,
30 octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin,
tecloftalam, copper sulphate and other copper preparations.


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Insecticides / acaricides / nematicides
abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb, aldoxycarb, alpha-
cypermethrin, alphamethnn, amitraz, avermectin, AZ 60541, azadirachtin,
5 azamethiphos, azinphos A, azinphos M, azocyclotin,
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella, bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin, bifenazate, bifenthrin, bioethanomethrin, biopermethrin, BPMC, bromophos A, bufencarb, buprofezin, butathiofos,
10 butocarboxim, butylpyridaben,
cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin, cloethocarb, clofentezine, cyanophos, cycloprene, cycloprothrin,
15 cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron, diazinon, dichlorvos, diflubenzuron, dimethoat, dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn, eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp., esfenvalerate,
20 ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole, etrimfos,
fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron, flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,
25 furathiocarb,
granulosis viruses,
halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene, imidacloprid, isazofos, isofenphos, isoxathion, ivermectin, lambda-cyhalothrin, lufenuron,


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malathion, mecarbam, metaldehyde, methamidophos, Metharhizium anisopliae,
Metharhizium flavoviride, methidathion, methiocarb, methomyl, methoxyfenozide,
metolcarb, metoxadiazone, mevinphos, milbemectin, monocrotophos,
naled, nitenpyram, nithiazine, novaluron, nuclear polyhedrosis viruses,
5 omethoat, oxamyl, oxydemethon M,
Paecilomyces fumosoroseus, parathion A, parathion M, permethrin, phenthoat, phorat, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur, prothiofos, prothoat, pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen,
10 pyriproxyfen,
quinalphos, ribavirin,
salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos, tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron,
15 tefluthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, theta-cypermethrin,
thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate, triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron, trimethacarb, vamidothion, vaniliprole, Verticillium lecanii,
20 YI5302
zeta-cypermethrin, zolaprofos
(lR-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcycIopropanecarboxylate (3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate
25 l-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-l,3,5-triazine-
2(lH)-imine
2-(2-chloro-6-fluorophenyl)-4-[4-(l,l-dimethylethyl)phenyl]-4,5-dihydro-oxazole 2-(acetlyoxy)-3-dodecyI-l,4-naphthalenedione 2-chloro-N-[[[4-(l-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide
30 2-chloro-N-[[[4-(2,2-dichloro-l,l-difluoroethoxy)-phenyl]-amino]-carbonyl]-
benzamide


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3-methylphenyl propylcarbamate
4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1 -fluoro-2-phenoxy-benzene
4-chloro-2-(l,l-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone
5 4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-
pyridazinone
4-chloro-54[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-
pyridazinone
Bacillus thuringiensis strain EG-2348
10 [2-benzoyl-l-(l,l-dimethylethyl)-hydrazinobenzoic acid
2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-l-oxaspiro[4.5]dec-3-en-4-ylbutanoate
[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide
dihydro-2-(nitromethylene)-2H-l,3-thiazine-3(4H)-carboxaldehyde
ethyl [2-[[l,6-dihydro-6-oxo-l-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate
15 N-(3,4,4-trifluoro-l-oxo-3-butenyl)-glycine
N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-lH-
pyrazole-1 -carboxamide
N-[(2-chloro-5-thiazolyl)methyl]-N"-methyl-N"-nitro-guanidine
N-methyl-N"-(l-methyl-2-propenyl)-l,2-hydrazinedicarbothioamide
20 N-methyl-N"-2-propenyl-l,2-hydrazinedicarbothioamide
0,0-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.
Mixtures with other known active compounds such as herbicides or with fertilizers and growth regulators are also possible.
25
When used as insecticides, 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 synergists. Synergists are compounds which increase the action of the active compounds, without it being
30 necessary for the synergist added to be active itself.


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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.
5
The compounds are employed in a customary manner appropriate for the use forms.
When used against hygiene pests and stored-product pests, the active compound is
distinguished by an excellent residual action on wood and clay as well as good
10 stability to alkali on limed substrates.
The active compounds according to the invention are not only active against plant
pests, hygiene pests and stored-product pests, but also, in the veterinary medicine
sector, against animal parasites (ectoparasites) such as hard ticks, soft ticks, mange
15 mites, harvest mites, flies (stinging and licking), parasitizing fly larvae, lice, hair lice,
bird lice and fleas. These parasites include:
From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
20
From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Wemeckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
25
From the order Diptera and the suborders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca
30 spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp.,
Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,

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Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.
From the order of the Siphonapterida, for example, Pulex spp., Ctenocephalides spp.,
5 Xenopsylla spp., Ceratophyllus spp.
From the order of the Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
10 From the order of the Blattarida, for example, Blatta orientalis, Periplaneta
americana, Blattela germanica, Supella spp.
From the subclass of the Acaria (Acarida) and the orders of the Meta- and
Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp.,
15 Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp.,
Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.
From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for
20 example, Acarapis spp., Cheyletiella spp., Omithocheyletia spp., Myobia spp.,
Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp. 25
The active compounds according to the invention are also suitable for controlling
arthropods which attack agricultural livestock such as, for example, cattle, sheep,
goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks,
geese, honey-bees, other domestic animals such as, for example, dogs, cats, caged
30 birds, aquarium fish and so-called experimental animals such as, for example,
hamsters, guinea pigs, rats and mice. By controlling these arthropods, cases of death

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and reductions in productivity (for meat, milk, wool, hides, eggs, honey and the like) should be diminished, so that more economical and simpler animal husbandry is possible by the use of the active compounds according to the invention.
5 The active compounds according to the invention are used in the veterinary sector in
a known manner by enteral administration in the form of, for example, tablets,
capsules, potions, drenches, granules, pastes, boluses, the feed-through method,
suppositories, by parenteral administration such as, for example, by injections
(intramuscularly, subcutaneously, intravenously, intraperitoneally and the like),
10 implants, by nasal administration, by dermal administration in the form of, for
example, immersing or dipping, spraying, pouring-on, spotting-on, washing, dusting, and with the aid of active-compound-comprising moulded articles such as collars, ear tags, tail tags, limb bands, halters, marking devices and the like.
15 When used fcr cattle, poultry, domestic animals and the like, the active compounds
can be applied as formulations (for example powders, emulsions, flowables) comprising the active compounds in an amount of 1 to 80% by weight, either directly or after 100- to 10 000-fold dilution, or they may be used as a chemical dip.
20 Moreover, it has been found that the active compounds according to the invention
show a potent insecticidal action against insects which destroy industrial materials.
The following insects may be mentioned by way of example and with preference, but not by way of limitation:
25
Beetles such as
Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus
30 pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec, Tryptodendron


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spec, Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec, Dinoderus minutus.
Dermapterans such as
5 Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
Termites such as
Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes
flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes
10 darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
Bristle-tails such as Lepisma saccharina.
Industrial materials in the present context are understood as meaning non-living
15 materials such as, preferably, polymers, adhesives, glues, paper and board, leather,
wood, timber products and paints.
The material which is to be protected from insect attack is very especially preferably wood and timber products. 20
Wood and timber products which can be protected by the composition according to the invention, or mixtures comprising it, are to be understood as meaning, for example:
25 Construction timber, wooden beams, railway sleepers, bridge components, jetties,
vehicles made of wood, boxes, pallets, containers, telephone poles, wood lagging, windows and doors made of wood, plywood, chipboard, joinery, or timber products which quite generally are used in house construction or building joinery.


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The active compounds can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
5 The abovementioned formulations can be prepared in a manner known per se, for
example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and/or binder or fixative, water repellant, if desired desiccants and UV stabilizers, and if desired colorants and pigments and other processing auxiliaries. 10
The insecticidal compositions or concentrates used for protecting wood and timber products comprise the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
15 The amount of composition or concentrate employed depends on the species and the
abundance of the insects and on the medium. The optimal quantity to be employed can be determined in each case by test series upon application. In general, however, it will suffice to employ 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
20
A suitable solvent and/or diluent is an organochemical solvent or solvent mixture and/or an oily or oil-type organochemical solvent or solvent mixture of low volatility and/or a polar organochemical solvent or solvent mixture and/or water and, if appropriate, an emulsifier and/or wetter.
25
Organochemical solvents which are preferably employed are oily or oil-type solvents with an evaporation number of above 35 and a flash point of above 30°C, preferably above 45°C. Such oily and oil-type solvents which are insoluble in water and of low volatility and which are used are suitable mineral oils or their aromatic fractions or
30 mineral-oil-containing solvent mixtures, preferably white spirit, petroleum and/or
alkylbenzene.


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Mineral oils with a boiling range of 170 to 220°C, white spirit with a boiling range of
170 to 220°C, spindle oil with a boiling range of 250 to 350°C, petroleum and
aromatics with a boiling range of 160 to 280°C, oil of terpentine, and the like are
5 advantageously used.
In a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range of 180
to 210°C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a
boiling range of 180 to 220°C and/or spindle oil and/or monochloronaphthalene,
10 preferably a-monochloronaphthalene are used.
The organic oily or oil-type solvents of low volatility and with an evaporation
number of above 35 and a flash point of above 30°C, preferably above 45°C, can be
replaced in part by organochemical solvents of high or medium volatility, with the
15 proviso that the solvent mixture also has an evaporation number of above 35 and a
flash point of above 30°C, preferably above 45°C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
In a preferred embodiment, some of the organochemical solvent or solvent mixture is
20 replaced by an aliphatic polar organochemical solvent or solvent mixture. Aliphatic
organochemical solvents which contain hydroxyl and/or ester and/or ether groups are preferably used, such as, for example, glycol ethers, esters or the like.
Organochemical binders used for the purposes of the present invention are the
25 synthetic resins and/or binding drying oils which are known per se and which can be
diluted in water and/or dissolved or dispersed or emulsified in the organochemical
solvents employed, in particular binders composed of, or comprising, an acrylate
resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation
or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenol
30 resin, hydrocarbon resin such as indene/coumarone resin, silicone resin, drying


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vegetable and/or drying oils and/or physically drying binders based on a natural and/or synthetic resin.
The synthetic resin employed as binder can be employed in the form of an emulsion,
5 dispersion or solution. Bitumen or bituminous substances may also be used as
binders, in amounts of up to 10% by weight. In addition, colorants, pigments, water repellants, odour-masking agents, and inhibitors or anticorrosive agents and the like, all of which are known per se, can be employed.
10 In accordance with the invention, the composition or the concentrate preferably
comprises, as organochemical binders, at least one alkyd resin or modified alkyd resin and/or a drying vegetable oil. Alkyd resins which are preferably used in accordance with the invention are those with an oil content of over 45% by weight, preferably 50 to 68% by weight.
15
Some or all of the abovementioned binder can be replaced by a fixative (mixture) or plasticizer (mixture). These additives are intended to prevent volatilization of the active compounds, and also crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of binder employed).
20
The plasticizers are from the chemical classes of the phthalic esters, such as dibutyl phthalate, dioctyl phthalate or benzyl butyl phthalate, phosphoric esters such as tributyl phosphate, adipic esters such as di-(2-ethylhexyl)-adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ethers or higher-
25 molecular-weight glycol ethers, glycerol esters and p-toluenesulphonic esters.
Fixatives are based chemically on polyvinyl alkyl ethers such as, for example, polyvinyl methyl ether, or ketones such as benzophenone and ethylenebenzophenone.


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Other suitable solvents or diluents are, in particular, water, if appropriate as a mixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants.
5 Particularly effective timber protection is achieved by industrial-scale impregnating
processes, for example the vacuum, double-vacuum or pressure processes.
The ready-to-use compositions can also comprise other insecticides, if appropriate, and also one or more fungicides, if appropriate. 10
Possible additional mixing components are, preferably, the insecticides and fungicides mentioned in WO 94/29 268. The compounds mentioned in this document are an explicit constituent of the present application.
15 Especially preferred mixing partners which may be mentioned are insecticides, such
as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyfenozide and triflumuron,
20 and also fungicides, such as epoxyconazole, hexaconazole, azaconazole,
propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid, 3-iodo-2-propinyl-butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.
25 The combinations according to the invention can at the same time be employed for
protecting objects which come into contact with saltwater or brackish water, such as hulls, screens, nets, buildings, moorings and signalling systems, against fouling.
Fouling by sessile Oligochaeta, such as Serpulidae, and by shells and species from
30 the Ledamorpha group (goose barnacles), such as various Lepas and Scalpel 1 urn
species, or by species from the Balanomorpha group (acorn barnacles), such as


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Balanus or Pollicipes species, increases the frictional drag of ships and, as a consequence, leads to a marked increase in operation costs owing to higher energy consumption and additionally frequent residence in the dry dock.
5 Apart from fouling by algae, for example Ectocarpus sp. and Ceramium sp., fouling
by sessile Entomostraka groups, which come under the generic term Cirripedia (cirriped crustaceans), is of particular importance.
Surprisingly, it has now been found that the combinations according to the invention,
10 alone or in combination with other active compounds, have an outstanding
antifouling action.
Using the combinations according to the invention, alone or in combination with other active compounds, allows the use of heavy metals such as, for example, in
15 bis(trialkyltin) sulphides, tri-n-butyltin laurate, tri-n-butyltin chloride, copper(I)
oxide, triethyltin chloride, tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin
oxide, molybdenum disulphide, antimony oxide, polymeric butyl titanate, phenyl-
(bispyridine)-bismuth chloride, tri-n-butyltin fluoride, manganese
ethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zinc
20 ethylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol 1-oxide,
bisdimethyldithiocarbamoylzinc ethylene-bisthiocarbamate, zinc oxide, copper(I) ethylene-bisdithiocarbamate, copper thiocyanate, copper naphthenate and tributyltin halides to be dispensed with, or the concentration of these compounds substantially reduced.
25
If appropriate, the ready-to-use antifouling paints can additionally comprise other active compounds, preferably algicides, fungicides, herbicides, molluscicides, or other antifouling active compounds.
30 Preferably suitable components in combinations with the antifouling compositions
according to the invention are:


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algicides such as
2-tert-butylamino-4-cyclopropylarnino-6-methylthio-l,3,5-triazine, dichlorophen,
diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen,
5 quinoclamine and terbutryn;
fungicides such as
benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide, dichlofluanid,
fluorfolpet, 3-iodo-2-propinyl butylcarbamate, tolylfluanid and azoles such as
10 azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole,
propiconazole and tebuconazole;
molluscicides such as
fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb and trimethacarb; 15
or conventional antifouling active compounds such as
4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatryl sulfone, 2-(N,N-
dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium, copper, sodium and zinc salts
of 2-pyridinethiol 1-oxide, pyridine-triphenylborane, tetrabutyldistannoxane, 2,3,5,6-
20 tetrachloro-4-(methylsulfonyl)-pyridine, 2,4,5,6-tetrachloroisophthalonitrile,
tetramethylthiuram disulfide and 2,4,6-trichlorophenylmaleiimide.
The antifouling compositions used comprise the active compound according to the
invention of the compositions according to the invention in a concentration of 0.001
25 to 50% by weight, in particular 0.01 to 20% by weight.
Moreover, the antifouling compositions according to the invention comprise the
customary components such as, for example, those described in Ungerer, Chem. Ind.
1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge,
30 1973.


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Besides the algicidal, fungicidal, molluscicidal active compounds and insecticidal active compounds according to the invention, antifouling paints comprise, in particular, binders.
5 Examples of recognized binders are polyvinyl chloride in a solvent system,
chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular
for an aqueous system, vinyl chloride/vinyl acetate copolymer systems in the form of
aqueous dispersions or in the form of organic solvent systems,
butadiene/styrene/acrylonitrile rubbers, drying oils such as linseed oil, resin esters or
10 modified hardened resins in combination with tar or bitumens, asphalt and epoxy
compounds, small amounts of chlorine rubber, chlorinated polypropylene and vinyl resins.
If appropriate, paints also comprise inorganic pigments, organic pigments or
15 colorants which are preferably insoluble in salt water. Paints may furthermore
comprise materials such as colophonium to allow controlled release of the active
compounds. Furthermore, the paints may comprise plasticizers, modifiers which
affect the rheological properties and other conventional constituents. The compounds
according to the invention or the abovementioned mixtures may also be incorporated
20 into self-polishing antifouling systems.
The active compounds are also suitable for controlling animal pests, in particular
insects, arachnids and mites, which are found in enclosed spaces such as, for
example, dwellings, factory halls, offices, vehicle cabins and the like. They can be
25 employed alone or in combination with other active compounds and excipients in
domestic insecticide products for controlling these pests. They are active against sensitive and resistant species and against all developmental stages. These pests include:
30 From the order of the Scorpionidea, for example, Buthus occitanus.


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From the order of the Acarina, for example, Argas persicus, Argas reflexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus, Omithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae. 5
From the order of the Araneae, for example, Aviculariidae, Araneidae.
From the order of the Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium. 10
From the order of the Isopoda, for example, Oniscus asellus, Porcellio scaber.
From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus spp.
15 From the order of the Chilopoda, for example, Geophilus spp.
From the order of the Zygentoma, for example, Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
20 From the order of the Blattaria, for example, Blatta orientalies, Blattella germanica,
Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.
25 From the order of the Saltatoria, for example, Acheta domesticus.
From the order of the Dermaptera, for example, Forficula auricularia.
From the order of the Isoptera, for example, Kalotermes spp., Reticulitermes spp. 30
From the order of the Psocoptera, for example, Lepinatus spp., Liposcelis spp.


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From the order of the Coleptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum. 5
From the order of the Diptera, for example, Aedes aegypti, Aedes albopictus, Aedes
taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis,
Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia
canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium
10 spp., Stomoxys calcitrans, Tipula paludosa.
From the order of the Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
15 From the order of the Siphonaptera, for example, Ctenocephalides canis,
Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
From the order of the Hymenoptera, for example, Camponotus herculeanus, Lasius
fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula
20 spp., Tetramorium caespitum.
From the order of the Anoplura, for example, Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.
25 From the order of the Heteroptera, for example, Cimex hemipterus, Cimex
lectularius, Rhodinus prolixus, Triatoma infestans.
In the field of household insecticides, they are used alone or in combination with
other suitable active compounds, such as phosphoric acid esters, carbamates,
30 pyrethroids, growth regulators or active compounds from other known classes of
insecticides.


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They are used as aerosols, pressure-free spray products, for example pump and
atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator
products with evaporator tablets made of cellulose or polymer, liquid evaporators, gel
5 and membrane evaporators, propeller-driven evaporators, energy-free, or passive,
evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for spreading or in bait stations.
The active compounds according to the invention can be used as defoliants,
10 desiccants, haulm killers and, especially, as weed killers. Weeds in the broadest sense
are understood to mean all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
15 The active compounds according to the invention can be used, for example, in
connection with the following plants:
Dicotyledonous weeds of the genera: Abutilon, Amarantnus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea,
20 Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,
Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,
25 Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia. 30


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Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus,
Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus,
Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa,
Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium,
5 Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,
Scirpus, Setaria, Sorghum.
Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea. 10
However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
The active compounds according to the invention are suitable, depending on the
15 concentration, for the total control of weeds, for example on industrial terrain and rail
tracks, and on paths and areas with and without tree plantings. Similarly, the active
compounds according to the invention can be employed for controlling weeds in
perennial crops, for example forests, decorative tree plantings, orchards, vineyards,
citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations,
20 rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and
hop fields, on lawns, turf and pastureland, and for the selective control of weeds in annual crops.
The compounds according to the invention have strong herbicidal activity and a
25 broad active spectrum when used on the soil and on above-ground parts of plants. To
a certain extent they are also suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both by the pre-emergence and by the post-emergence method.
30 At certain concentrations or application rates, the active compounds according to the
invention can also be employed for controlling animal pests and fungal or bacterial


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plant diseases. If appropriate, they can also be used as intermediates or precursors tor the synthesis of other active compounds.
All plants and plant parts can be treated in accordance with the invention. Plants are
5 to be understood as meaning in the present context all plants and plant populations
such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional plant breeding and optimization methods or by biotechnological and recombinant methods or by combinations of these methods, including the transgenic
10 plants and inclusive of the plant varieties protectable or not protectable by plant
breeders" rights. Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. The plant parts also include harvested
15 material, and vegetative and generative propagation material, for example cuttings,
tubers, rhizomes, offsets and seeds.
Treatment according to the invention of the plants and plant parts with the active
compounds is carried out directly or by allowing the compounds to act on the
20 surroundings, environment or storage space by the customary treatment methods, for
example by immersion, spraying, evaporation, fogging, scattering, painting on and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.
25 As already mentioned above, it is possible to treat all plants and their parts according
to the invention. In a preferred embodiment, wild plant species and plant varieties, or those obtained by conventional biological breeding, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant varieties obtained by geneticaJ engineering, if appropriate in
30 combination with conventional methods (Genetically Modified Organisms), and parts


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thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above.
Particularly preferably, plants of the plant varieties which are in each case
5 commercially available or in use are treated according to the invention. Plant
varieties are to be understood as meaning plants having certain properties ("traits") and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be varieties, bio- or genotypes.
10 Depending on the plant species or plant varieties, their location and growth
conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions to be used according to
15 the invention, better plant growth, increased tolerance to high or low temperatures,
increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible which exceed the
20 effects which were actually to be expected.
The transgenic plants or plant varieties (i.e. those obtained by genetical engineering) which are preferably treated according to the invention include all plants which, in the genetic modification, received genetic material which imparted particularly
25 advantageous useful properties ("traits") to these plants. Examples of such properties
are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or
30 processability of the harvested products. Further and particularly emphasized
examples of such properties are a better defence of the plants against animal and

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microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or
viruses, and also increased tolerance of the plants to certain herbicidally active
compounds. Examples of transgenic plants which may be mentioned are the
important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes,
5 cotton, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits
and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton and oilseed rape. Traits that are emphasized are in particular increased defence of the plants against insects by toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes
10 CrylA(a), CrylA(b), CrylA(c), CryllA, CrymA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb
and CrylF and also combinations thereof) (hereinbelow referred to as "Bt plants"). Traits that are also particularly emphasized are the increased defence of the plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins
15 and toxins. Traits that are furthermore particularly emphasized are the increased
tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the "PAT" gene). The genes which impart the desired traits in question can also be present in combination with one another in the transgenic plants. Examples of "Bt
20 plants" which may be mentioned are maize varieties, cotton varieties, soya bean
varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned
25 are maize varieties, cotton varieties and soya bean varieties which are sold under the
trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), EMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylurea, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for
30 herbicide tolerance) which may be mentioned include the varieties sold under the
name Clearfield® (for example maize). Of course, these statements also apply to


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plant varieties having these genetic traits or genetic traits still to be developed, which plants will be developed and/or marketed in the future.
The plants listed can be treated according to the invention in a particularly
5 advantageous manner with the compounds of the formula (I). The preferred ranges
stated above for the active compounds also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the mixtures specifically mentioned in the present text.
10 The active compounds can be converted into the customary formulations such as
solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric materials.
15 These formulations are produced in a known manner, for example by mixing the
active compounds with extenders, that is, liquid solvents and/or solid carriers, optionally with the use of surfactants, that is, emulsifiers and/or dispersants, and/or foam formers.
20 If the extender used is water, it is also possible, for example, to use organic solvents
as cosolvents. The following are essentially suitable as liquid solvents: 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
25 mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol
and 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, or else water.
30 Suitable solid carriers are: for example ammonium salts and ground natural minerals
such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or


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diatomaceous earth, and ground synthetic materials such as highly-disperse silica,
alumina and silicates; suitable solid carriers for granules are: for example crushed
and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite,
or else synthetic granules of inorganic and organic meals, and granules of organic
5 material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable
emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers
such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for
example alkylaryl polyglycol ethers, alkylsulphonates, .alkyl sulphates,
arylsulphonates, or else protein hydrolysates; suitable dispersants are: for example
10 lignin-sulphite waste liquors and methylcellulose.
Tackifiers 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, or else natural phospholipids such as cephalins and lecithins and
15 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 colorants such alizarin colorants, azo
20 colorants and metal phthalocyanine colorants, and trace nutrients such as salts of
iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
25
For controlling weeds, the active compounds according to the invention, as such or in their formulations, can also be used as mixtures with known herbicides and/or substances which improve the compatibility with crop plants ("safeners"), finished formulations or tank mixes being possible. Also possible are mixtures with weed-
30 killers comprising one or more known herbicides and a safener.


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Possible components for the mixtures are known herbicides, for example
acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium),
ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine,
5 azafenidin, azimsulfuron, BAS-662H, beflubutamid, benazolin (-ethyl), benfuresate,
bensulfuron (-methyl), bentazon, benzfendizone, benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone (-ethyl), chlomethoxyfen,
10 chloramben, chloridazon, chlorimuron (-ethyl), chlornitrofen, chlorsulfuron,
chlortoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron (-methyl), cloransulam (-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, desmedipham,
15 diallate, dicamba, dichlorprop (-P), diclofop (-methyl), diclosulam, diethatyl (-ethyl),
difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid,
20 fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl, -isopropyl-L, -methyl),
flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone,
25 fluroxypyr (-butoxypropyl, -meptyl), flurprimidol, flurtamone, fluthiacet (-methyl),
fluthiamide, fomesafen, foramsulfuron, glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop (-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil,
30 isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole,
isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacet, mesotrione,


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metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron,
(alpha-) metolachlor, metosulam, metoxuron, metribuzin, metsulfuron (-methyl),
molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron,
norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,
5 oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin,
pentoxazone, phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron (-methyl), profluazol, prometryn, propachlor, propanil, propaquizafop, propisochlor, propoxycarbazone (-sodium), propyzamide, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxim,
10 pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac (-methyl), pyrithiobac
(-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl, -P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin,
15 thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron,
tribenuron (-methyl), triclopyr, tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl), tritosulfuron.
A mixture with other known active compounds, such as fungicides, insecticides,
20 acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil
structure, is also possible.
The active compounds can be used as such, in the form of their formulations or in the
use forms prepared therefrom by further dilution, such as ready-to-use solutions,
25 suspensions, emulsions, powders, pastes and granules. They are used in a customary
manner, for example by watering, spraying, atomizing or broadcasting.
The active compounds according to the invention can be applied both before and
after emergence of the plants. They can also be incorporated into the soil before
30 sowing.


The amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.
Accordingly the present invention relates to phenyl-substituted 4-hydroxy-tetrahydropyridones compounds of the formula (I)

(I)
in which
W represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl,
X represents chlorine, bromine, methyl, ethyl, propyl or trifluoromethyl,
Y represents hydrogen, chlorine, bromine, fluorine, methyl, ethyl or the
radical

V1 represents hydrogen, fluorine, chlorine, bromine, methyl, tert-butyl, methoxy, trifluoromethyl or phenyl,


V2 represents hydrogen, fluorine, chlorine methyl, methoxy or trifluoromethyl,
Z represents hydrogen, bromine, chlorine or methyl,
A represents methyl, ethyl or propyl,
B represents methyl or ethyl,
A, B and the carbon atom to which they are attached represent saturated C5-C6-cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, ethyl, methoxy, ethoxy, n-propoxy or n-butoxy,
D represents hydrogen,
D represents cyclopropyl, cyclopentyl or cyclohexyl,
Q1 and Q2 represent hydrogen,
D and Q1 represent butanediyl,
G represents hydrogen (a) or represents one of the groups

in which M represents oxygen or sulphur,
R1 represents C1-C8-alkyl, C2-C4-alkenyl, methoxymethyl, ethoxymethyl,
ethylthiomethyl or optionally fluorine-, chlorine-, methyl-, ethyl- or methoxy-substituted cyclopropyl, cyclopentyl or cyclohexyl,


represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-, iso-propyl-, tert-butyl-, methoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl,
represents in each case optionally chlorine-, or methyl-substituted thienyl or pyridyl,
R2 represents in each case optionally fluorine-substituted C1-C8-alkyl, C2-C4-alkenyl or methoxyethyl, ethoxyethyl, propoxyethyl, iso-propoxyethyl, cyclopentyl or cyclohexyl,
or represents in each case optionally fluorine-, chlorine-, cyano-, nitro-, methyl-, ethyl-, iso-propyl-, tert-butyl-, methoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl or benzyl,
R3 represents methyl,
R6 and R7 together represent a C6-alkylene radical in which optionally one methylene group is replaced by oxygen.
The preparation and the use of the active compounds according to the invention is illustrated by the examples below.


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Preparation examples Example I-a-1

3.9 g (0.13 mol) of sodium hydride in 70 ml of absolute toluene are heated at reflux,
and 33.1 g of the compound of Example II-l in 100 ml of absolute toluene are added
dropwise. The reaction is monitored by thin-layer chromatography. With ice-cooling,
10 ethanol is added until no more hydrogen evolves, the solvent is evaporated and water
is added. The toluene phase is separated off, and the aqueous phase is then acidified at 0-20°C with concentrated hydrochloric acid and the precipitate is filtered off and dried.
15 The product is purified by silica gel column chromatography (dichlorometahne/ethyl
acetetate 3:1). Yield: 8.41 g (30% of theory), m.p. 127°C.


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Example I-a-2

At room temperature, 3 mmol of the compound of Example I-a-4 are initially charged in 8 ml of DME (dimethoxyethane), and 6.9 ml of a 1M NaCO3 solution are added. 4.5 mmol of biphenylboronic acid are added, followed by 0.15 mmol of Pd(PPh3)2Cl2, and the mixture is stirred at room temperature for 1 h at then at 85°C for 16 h.
Purification was carried out on silica gel using the mobile phase cyclohexane/ethyl acetate (gradient from 100:1 to 1:1). Yield: 0.302 g (26.3% of theory), oil.


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Table 1
The following compounds of the formula (I-a) were obtained analogously to Examples (I-a-1) and (I-a-2) and in accordance with the general statements on the preparation


(I-a)



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Table 1 (Continued)



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Table 1 (Continued)

-98-

Le A 34 338-Foreign Countries
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5 At 0-10°C, 4.95 g of the compound of Example I-a-1 in 70 ml of methyl tert-butyl
ether are admixed with 1.4 ml of absolute pyridine and 2.94 ml of ethyl-diisopropylamine. 2.2 ml of pivaloyl chloride in 5 ml of methyl tert-butyl ether are then added, and the mixture is stirred at room temperature. The mixture is filtered off with suction, the residue is washed with methyl tert-butyl ether and the solution is
10 concentrated. The reaction mixture is purified by column chromatography
(cyclohexane/ethyl acetate 1:1). Yield: 3.42 g (55% of theory), oil


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100
Table 2
The following compounds of the formula (I-b) are obtained analogously to Example I-b-1 and in accordance with the general statements


on the preparation

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Example I-c-1

5 1.3 g of the compound of Example I-a-5 in 30 ml of absolute dichloromethane are, at
10-20°C, admixed with 0.42 ml of triethylamine and then with 0.3 ml of ethyl
chloroformate in 2 ml of absolute dichloromethane, and the mixture is stirred at room
temperature. The reaction mixture is washed twice with 10 ml of 0.5 N NaOH and
the solution is dried over magnesium sulphate and concentrated using a rotary
10 evaporator. The product is purified by silica gel colum chromatograpy
(dichloromethane/ethyl acetate, 3/1). Yield: 1.1 g (88% of theory) m.p. 195°C.


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The following compounds of the formula (I-c) were obtained analogously to Example I-c-1 and in accordance with the general statements on the preparation:

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Example I-d-1




10

1.02 g (3 mmol) of the compound of Preparation Example I-a-5 in 10 ml of absolute dichloromethane are admixed with 0.54 ml of triethylamine. 0.26 ml (3.3 mmol) of methanesulphonyl chloride is dissolved in a little dichloromethane and added dropwise with ice-cooling. The mixture is stirred at room temperature for 2 h. The reaction solution is washed with 10% strength citric acid and extracted with dichloromethane. The organic phase is washed with 1 N NaOH solution and dried. Yield: 1.05 g (83% of theory), m.p. 198-200°C.

Example I-A-g-1

15


1.02 g (3.0 mmol) of the compound of Preparation Example I-a-5 and 0.54 ml (3.90 mmol) of triethylamine are dissolved in 10 ml of absolute ethyl acetate and



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heated at reflux. 0.47 g (3.15 mmol) of morpholine-N-carbonyl chloride in 2 ml of absolute ethyl acetate is added. The mixture is heated at reflux for 2 h.
The solvent is distilled off and the residue is taken up in 50 ml of dichloromethane.
5 The mixture is washed twice with 30 ml of semiconcentrated NaCl solution and
extracted twice with 30 ml of 0.5 N NaOH solution. The organic phase is dried and concentrated. The product is purified by silica gel column chromatography (cyclohexane/ethyl acetate, 5:1 →1:1). Yield 0.200 g (15% of theory), m.p. 221-223°C.
Example I-B-g-1

15 1.02 g (3.0 mmol) of the compound of Preparation Example I-a-5 and 0.54 ml
(3.90 mmol) of triethylamine are dissolved in 10 ml of absolute ethyl acetate and heated at reflux. 0.47 g (3.15 mmol) of morpholin-N-carboxylic acid in 2 ml of absolute ethyl acetate are added. The mixture is heated at reflux for 2 h.
20 The solvent is distilled off and the residue is taken up in 50 ml of dichloromethane.
The mixture is washed twice with 30 ml of semiconcentrated NaCl solution and extracted twice with 30 ml of 0.5 N NaOH solution. The organic phase is dried and concentrated. The product is purified by silica gel column chromatography (cyclohexane/ethyl acetate, 5:1 → 1:1). Yield 0.480 g (35% of theory), m.p. 95-97°C.


105-
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Example II-l

At 0-10°C, 14 ml of triethylamine are added to 17.1 g of ethyl 2-piperidinyl-acetate in 130 ml of absolute tetrahydrofuran. At room temperature, 19.7 g of mesitylene acetyl chloride in 20 ml of absolute tetrahydrofuran are then added.
The reaction solution is added to 0.5 1 of ice-water and acidified with 100 ml of IN HC1. The solution is extracted with dichloromethane, the extract is dried and the solvent is evaporated. Yield: 33.4 g (100% of theory)


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Table 3
The following compounds of the formula (II) are obtained analogously to Example II-l and in accordance with the general statements on the preparation:




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Use examples
Example A
5 Meloidogyne test
Solvent: 30 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
I 10 To produce a suitable preparation of active compound, 1 part by weight of active
compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
Containers are filled with sand, solution of active compound, Meloidogyne incognita
15 egg/larvae suspension and lettuce seeds. The lettuce seeds germinate and the plants
develop. On the roots, galls are formed.
After the desired period of time, the nematicidal action in % is determined using the
formation of galls as a measure. 100% means that no galls have been found; 0%
20 means that the number of galls on the treated plants corresponds to that on the
I untreated control.
In this test, the compound of Preparation Example I-a-4 exhibited, at an exemplary active compound concentration of 20 ppm, a kill of 95% after 14 days.
25

Le A 34 338-Foreign Countries
-110-
Example B
Tetranychus test (OP-resistent/dip treatment)
5 Solvent: 30 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 amounts of solvent and emulsifier, and the
10 concentrate is diluted with emulsifier-containing water to the desired concentration.
Bean plants (Phaseolus vulgaris) which are heavily infested by all stages of the greenhouse rat spider mite (Tetranychus urticae) are treated by being dipped into a preparation of active compound of the desired concentration. 15
After the desired period of time, the effect in % is determined. 100% means that all spider mites have been killed; 0% means that none of the spider mites have been killed.
20 In this test, for example, compounds of Preparation Examples I-a-5 and I-c-1 exhibit,
at an exemplary active compound concentration of 100 ppm, a kill of 99% (I-a-5) and 95% (I-c-1), respectively, after 7 days.


Le A 34 338-Foreign Countries
-111-Example C
Post-emergence test
5 Solvent: 5 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
10 emulsifier is added and the concentrate is diluted with water to the desired
concentration.
Test plants of a height of 5-15 cm are sprayed with the preparation of active
compound such that the particular amounts of active compound desired are applied
15 per unit area. The concentration of the spray liquor was chosen such that the
particular amounts of active compound desired are applied in 1 000 1 of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. 20
The figures denote:
0% = no effect (like untreated control) 100% = total destruction
25


Le A 34 338-Foreign Countries
-112-Example D
Pre-emergence test
5 Solvent: 5 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 to the stated amount of solvent, the stated amount of emulsifier
10 is added and the concentrate is diluted with water to the desired concentration.
Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is
sprayed with the preparation of active compounds such that the particular amounts of
active compound desired are applied per unit area. The concentration of the spray
15 liquor is chosen such that the particular amounts of active compound desired are
applied in 1 000 1 of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. 20
The figures denote:
0% = no effect (like untreated control)
100% = total destruction


Le A 34 338-Foreign Countries

-113-


Le A 34 338-Foreign Countries
-114-
Example E
Critical concentration test / soil insects - treatment of transgenic plants
5 Test insect: diabrotica balteata - larvae in soil
Solvent: 7 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
10 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.
15 The preparation of active compound is poured onto the soil. Here, the concentration
of the active compound in the preparation is virtually irrelevant, only the amount by weight of active compound per volume unit of soil, which is stated in ppm (mg/1) matters. The soil is filled into 0.25 1 pots and these are allowed to stand at 20°C.
20 Immediately after preparation, 5 pre-germinated maize corns of the variety
YIELD GUARD (trade mark of Monsanto Comp., USA) are placed into each pot. After 2 days, the test insects are placed into the treated soil. After a further 7 days, the efficacy of the active compound is determined by counting the maize plants that have emerged (1 plant = 20% efficacy).
25

1



Le A 34 338-Foreign Countries
-115-
Example F
Heliothis virescens test - treatment of transgenic plants
5 Solvent: 7 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 and the stated amount of
10 emulsifier, and the concentrate is diluted with water to the desired concentration.
Soya bean shoots (Glycine max) of the variety Roundup Ready (trade mark of
Monsanto Comp. USA) are treated by being dipped into the preparation of active
compound of the desired concentration and are populated with the tobacco budworm
15 Heliothis virescens while the leaves are still moist.
After the desired period of time, the kill of the insects is determined.


WE CLAIM:
1. Phenyl-substituted 4-hydroxy-tetrahydropyridones compounds of the formula (I)

in which
W represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl,
X represents chlorine, bromine, methyl, ethyl, propyl or trifluoromethyl,
Y represents hydrogen, methyl, ethyl, fluorine, chlorine, bromine or represents
the radical

V1 represents hydrogen, fluorine, chlorine, bromine, methyl, tert-butyl, methoxy, trifluoromethyl or phenyl,
V2 represents hydrogen, fluorine, chlorine methyl, methoxy or trifluoromethyl,
Z represents hydrogen, chlorine, bromine or methyl,
A and B represent hydrogen,


D represents hydrogen, methyl, ethyl, propyl, iso-propyl, cyclopropyl, cyclopentyl
or cyclohexyl,
D and Q1 together represent butanediyl,
Q1 represents methyl, ethyl or propyl,
Q2 represents methyl; if D and Q1 together represent butanediyl, Q2 may also
represent hydrogen, Q1 and Q2 together with the carbon to which they are attached represent optionally methyl-, ethyl-, methoxy-, ethoxy-, propoxy- or butoxy substituted C5-C6-cycloalkyl in which optionally one ring member is replaced by oxygen,
G represents hydrogen (a) or represents one of the groups

in which M represents oxygen or sulphur, .
R1 represents C1-C8-alkyl, C2-C4-alkenyl, methoxymethyl, ethoxymethyl,
ethylthiomethyl or optionally fluorine-, chlorine-, methyl-, ethyl- or methoxy-
substituted cyclopropyl, cyclopentyl or cyclohexyl,
represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-, iso-
propyl-, tert-butyl-, methoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl,
represents in each case optionally chlorine- or methyl-substituted thienyl or pyridyl,
R2 represents in each case optionally fluorine-substituted C1-C8-alkyl, C2-C4 alkenyl or methoxyethyl, ethoxyethyl, propoxyethyl, iso-propoxyethyl, cyclopentyl or cyclohexyl,


or represents in each case optionally fluorine-, chlorine-, cyano-, nitro-, methyl-, ethyl, iso-propyl-, tert-butyl-, methoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl or benzyl,
R3 represents methyl,
R6 and R7 together represent a C6-alkylene radical in which optionally one methylene group is replaced by oxygen.

in which
A, B, D, Q1 Q2 W, X, Y and Z are each as defined above,
compounds of the formula (II)

in which

2. Process for preparing compounds of the formula (I), wherein to obtain (A) compounds of the formula (I-a)

A, B, D, Q1, Q2 W, X, Y and Z are each as defined above,
and
R8 represents alkyl,
are condensed intramolecularly in the presence of a diluents, of the kind such as herein described and in the presence of a base, of the kind such as herein described
(B) compounds of the formulae (I-a) to (I-g) shown above

in which A, B, D, G, Q1, Q2 W, X, Y and Z are each as defined above, compounds of the formulae (I-a") to (I-g"),



in which
A, B, D,R1, R2 R3, R4, R5, R6, R7; E, L, M, Q1, Q2, W, X", Y" and Z"
are each as defined above and where at least one of the radicals
W, X", Y" represents chlorine, bromine or iodine
and Z" does not represent bromine or iodine
a) are initially reacted with silylacetylene of the formula (III)

in which
R9 represents hydrogen and
R10 represents C1-C4-alkyl or phenyl,
in the presence of a solvent, a base and a catalyst, of the kind such as herein
described, and the silyl group is then removed,
or
B) are reacted with vinylstannanes of the formula (IV)



in which
R9 represents hydrogen, methyl or ethyl and
R10 represents C1-C4-alkyl
in the presence of a solvent, if appropriate in the presence of a base and in the
presence of a catalyst, of the kind such as herein described
or
Y) if Y" represents chlorine, bromine or iodine, are reacted with boronic acids of the
formula (V)

in which
Y represents optionally substituted phenyl or hetaryl,
in the presence of a solvent, a base and a catalyst, of the kind such as herein
described
(C) the compounds of the formula (I-b) shown above in which A, B, D, Q1, Q2, R1, W, X, Y and Z are each as defined above, compounds of the formula (I-a) shown above in which A, B, D, Q1, Q2 W, X, Y and Z are each as defined above are in each case reacted

(a) with acid halides of the formula (VI)


in which
R1 is as defined above and
Hal represents halogen,
or
(b) with carboxylic anhydrides of the formula (VII)
R1-CO-O-CO-R1 (vn)
in which
R1 is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, of the kind such as herein described
(D) compounds of the formula (I-c) shown above in which A, B, D, Q1, Q2, R2, M, W,
X, Y and Z are each as defined above and L represents oxygen, compounds of the
formula (I-a) shown above in which A, B, D, Q1, Q2, W, X, Y and Z are each as defined
above are in each case reacted
with chloroformic esters or chloroformic thioesters of the formula (VIII)
R2-M-CO-Cl (VII)
in which
R2 and M are each as defined above
if appropriate in the presence of a diluent and if appropriate in the presence of an acid
binder, of the kind such as herein described
(E) compounds of the formula (I-c) shown above in which A, B, D.Q1, Q2, R2, M, W,
X, Y and Z are each as defined above and L represents sulphur, compounds of the


formula (I-a) shown above in which A, B, D, Q1, Q2, W, X, Y and Z are each defined above are in each case reacted
with chloromonothioformic esters or chlorodithioformic esters of the formula (IX)

in which
M and R2 are each as defined above
if appropriate in the presence of a diluent and if appropriate in the presence of an acid
binder, of the kind such as herein described
and
(F) compounds of the formula (I-d) shown above in which A, B, D, Q1, Q2, R3, W, X,
Y and Z are each as defined above, compounds of the formula (I-a) shown above in
which A, B, D, Q1, Q2 W, X, Y and Z are each as defined above are in each case reacted
with sulphonyl chlorides of the formula (X)


in which
R3 is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, of the kind such as herein described
(G) compounds of the formula (1-e) shown above in which A, B, D, L, Q1, Q2, R4, R5 W,
X, Y and Z are each as defined above, compounds of the formula (I-a) shown above in
which A, B, D, Q1, Q2, W, X, Y and Z are each as defined above are in each case
reacted


with phosphorus compounds of the formula (XI)

in which
L, R4 and R5 are each as defined above and
Hal represents halogen,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid
binder, of the kind such as herein described
(H) compounds of the formula (I-f) shown above in which A, B, D, E, Q1, Q2, W, X, Y and Z are each as defined above, compounds of the formula (I-a) shown above in which A, B, D, Q1, Q2 W, X, Y and Z are each as defined above are in each case reacted with metal compounds or amines of the formulae (XII) and (XIII)
Me(OR11)t (XII)
in which
Me represents a mono- or divalent metal,
t represents the number 1 or 2 and
R11, R12, R13 independently of one another each represent hydrogen or alkyl, if appropriate in the presence of a diluent, of the kind such as herein described,
(I) compounds of the formula (I-g) shown above in which A, B, D, L, Q1, Q2, R6, R7, W, X, Y and Z are each as defined above, compounds of the formula (I-a) shown above in which A, B, D, Q1, Q2, W, X, Y and Z are each as defined above are in each case reacted


(a) with isocyanates or isothiocyanates of the formula (XIV)
R6.N=C=L (XIV)
in which
R6 and L are each as defined above
if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst, of the kind such as herein described or
(β) with carbamoyl chlorides or thiocarbamoyl chlorides of the formula (XV)

in which
L, R6 and R7 are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, of the kind such as herein described.
3. Pesticides and herbicides, wherein they comprise between 0.1 and 95 % by weight of at least one compound of the formula (I) as claimed in claim 1 and/or extenders and surfactants of the kind such as herein described.
4. Phenyl-substituted 4-hydroxy-tetrahydropyridones compounds of the formula (I) substantially as hereinbefore described with reference to the foregoing examples.

Dated this April 4, 2001.
(DR. ANUSHRI GUPTA)
OF REMFRY AND SAGAR
ATTORNEY FOR THE APPLICANTS

Documents:

318-mum-2001-cancelled pages(4-2-2008).pdf

318-mum-2001-claims(granted)-(11-02-2008).doc

318-mum-2001-claims(granted)-(11-2-2008).pdf

318-mum-2001-correspondence(4-2-2008).pdf

318-mum-2001-correspondence(ipo)-(21-3-2008).pdf

318-mum-2001-form 1(5-6-2007).pdf

318-mum-2001-form 13(25-6-2007).pdf

318-mum-2001-form 13(4-2-2008).pdf

318-mum-2001-form 18(15-12-2005).pdf

318-mum-2001-form 2(granted)-(11-02-2008).doc

318-mum-2001-form 2(granted)-(11-2-2008).pdf

318-mum-2001-form 3(20-7-2001).pdf

318-mum-2001-form 3(31-5-2007).pdf

318-mum-2001-form 3(4-4-2001).pdf

318-mum-2001-form 5(4-11-2001).pdf

318-mum-2001-form-pct-ipea-409(5-1-2007).pdf

318-mum-2001-form-pct-isa-210(5-1-2007).pdf

318-mum-2001-petition under rule 138(5-6-2007).pdf

318-mum-2001-power of authority(11-2-2008).pdf

318-mum-2001-power of authority(15-6-2007).pdf

318-mum-2001-power of authority(4-4-2001).pdf


Patent Number 217007
Indian Patent Application Number 318/MUM/2001
PG Journal Number 13/2008
Publication Date 28-Mar-2008
Grant Date 24-Mar-2008
Date of Filing 04-Apr-2001
Name of Patentee BAYER AKTIENGESELLSCHAFT
Applicant Address D-51368 LEVERKUSEN, GERMANY
Inventors:
# Inventor's Name Inventor's Address
1 REINER FISCHER NELLY-SACHS-STR. 23, 40789 MONHEIM, GERMANY
2 ALAN GRAFF Lortzingstr. 35, 51375 Leverkusen
3 AXEL TRAUTWEIN Im Aehlemaar 23, 51467 Bergisch Gladbach
4 ASTRID ULLMANN Merowingerstr. 31, 50677 Köln
5 UDO SCHNEIDER Heymannstr. 38, 51373 Leverkusen
6 RALF WISCHNAT Morgengraben 14, 51061 Köln
7 MARK WILHELM DREWES Goethestr. 38, 40764 Langenfeld
8 CHRISTOPH ERDELEN Unterbüscherhof 15, 42799 Leichlingen
9 DIETER FEUCHT Ackerweg 9, 40789 Monheim
PCT International Classification Number C07D455/02
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 10019145.2 2000-04-18 Germany