2-hetaryl-3,4-dihydro-2H-pyrrole derivatives

Details 2-hetaryl-3,4-dihydro-2H-pyrrole derivatives 2-hetaryl-3,4-dihydro-2H-pyrrole derivatives

2001-04-05

2003-07-29

McKane, Joseph K. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C546S276400, C546S014000, C546S286000, C546S288000, C548S527000, C548S205000, C549S059000, C549S491000, C549S497000, C514S428000

Reexamination Certificate

active

06599924

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to novel 2-hetaryl-3,4-dihydro-2H-pyrrole derivatives, to a plurality of processes for their preparation and to their use as pesticides.
BACKGROUND OF THE INVENTION
Hitherto, only substituted cyclic &agr;,&agr;′-diphenylimines have been disclosed: three 2,5-diphenyl-1-pyrrolines which are alkoxy-substituted in the 2-phenyl ring [5-(2,5-dimethoxyphenyl)-2-phenyl-3,4-dihydro-2H-pyrrole and 5-(4-methoxyphenyl)-2-phenyl-3,4-dihydro-2H-pyrrole from Chem. Ber. 96, 93 (1963) and the corresponding 4-propoxy compound from J. Prakt. Chem., series 4, 1, 57 (1955)] and 2,6-diphenyl-3,4,5,6-tetrahydropyridine, which is not further substituted [cf., for example, Bull. Soc. Chim. Fr. 1974, 258 and Chem. Ber. 116, 3931 (1983)].
WO 98/22438 describes novel substituted &agr;,&agr;′-diphenylimines and their suitability for use as pesticides. However, hitherto nothing has been disclosed about substituted &agr;-hetaryl-&agr;′-phenylimines and their suitability for use as pesticides.
SUMMARY OF THE INVENTION
2-Hetaryl-3,4-dihydro-2H-pyrrole derivatives of the formula (I)
may be used as pesticides.
DETAILED DESCRIPTION
This invention accordingly provides novel 2-hetaryl-3,4-dihydro-2H-pyrrole derivatives of the formula (I)
in which
Hetaryl represents unsaturated 5 to 10-membered mono- or bicyclic heterocycles, for example 5 or 6-membered monocycles having one or more heteroatoms from the group consisting of N, O and S, optionally mono- or polysubstituted by radicals from the list H
1
, where
H
1
represents hydrogen, halogen, cyano, formyl, nitro, alkyl, trialkylsilyl, alkoxy, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, alkylcarbonyl, alkoxycarbonyl, pentafluorothio, carbamoyl, thiocarbamoyl, alkoximino or —S(O)
o
R
3
,
Ar represents the radical
 in which
m represents 0, 1, 2, 3 or 4,
R
1
represents halogen or represents one of the groupings below
(l) —X—A
(m) —B—Z—D
(n) —Y—E
R
2
represents hydrogen, halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, alkoxyalkoxy or —S(O)
o
R
3
,
o represents 0, 1 or 2,
R
3
represents alkyl or halogenoalkyl,
X represents a direct bond, oxygen, sulphur, carbonyl, carbonyloxy, oxycarbonyl, alkylene, alkenylene, alkinylene, alkyleneoxy, oxyalkylene, thioalkylene, alkylenedioxy or dialkylsilylene,
A represents phenyl, naphthyl or tetrahydronaphthyl, each of which is optionally mono- or polysubstituted by radicals from the list W
1
, or represents 5- to 10-membered heterocyclyl containing one or two aromatic rings and having one or more heteroatoms from the group consisting of nitrogen, oxygen and sulphur and being in each case optionally mono- or polysubstituted by radicals from the list W
2
,
B represents p-phenylene which is optionally mono- or disubstituted by radicals from the list W
1
,
Z represents oxygen or sulphur,
D represents hydrogen, alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, in each case optionally halogen, alkyl , alkenyl-, halogenoalkenyl-, phenyl-, styryl-, halogenophenyl- or haloenostyryl-substituted cycloalkyl or cycloalkylalkyl, represents in each case optionally halogen- or alkyl-substituted cycloalkenyl or cycloalkenylalkyl, represents in each case optionally nitro-, halogen- alkyl-, alkoxy-, halogenoalkyl- or halogenoalkoxy-substituted phenylalkyl, naphthylalkyl, tetrahydronaphthylalkyl or hetarylalkyl having 5 or 6 ring members and one or two heteroatoms from the group consisting of nitrogen, oxygen and sulphur, represents —CO—R
4
, —CO—NR
5
R
6
or represents the grouping
—(CH
2
)
p
—(CR
7
R
8
)
q
—(CH
2
)
r
—G
 or
Z and D together represent optionally nitro-, halogen-, alkyl-, alkoxy halogenoalkyl- or halogenoalkoxy-substituted phenoxyalkyl,
Y represents a direct bond, oxygen, sulphur, carbonyl, carbonyloxy, oxycarbonyl, alkylene, alkenylene, alkinylene, alkyleneoxy, oxyalkylene, thioalkylene, alkylenedioxy or represents p-phenylene which is optionally mono- or disubstituted by radicals from the list W
1
,
E represents hydrogen, alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, in each case optionally halogen-, alkyl-, alkenyl-, halogenoalkenyl-, phenyl-, styryl-, halogenophenyl- or halogenostyryl-substituted cycloalkyl, represents in each case optionally halogen- or alkyl-substituted cycloalkenyl, represents phenyl which is optionally mono- to tetrasubstituted by radicals from the list W
1
or represents 5- or 6-membered hetaryl having one or two heteroatoms from the group consisting of nitrogen, oxygen and sulphur and being in each case optionally mono- to tetrasubstituted by radicals from the list W
2
or represents the grouping
—(CH
2
)
p
—(CR
7
R
8
)
q
—(CH
2
)
r
—G
R
4
represents alkyl, alkoxy, alkenyl, alkenyloxy, in each case optionally halogen-, alkyl-, alkenyl-, halogenoalkyl- or halogenoalkenyl-substituted cycloalkyl, cycloalkyloxy or cycloalkylalkyloxy or represents in each case optionally nitro-, halogen-, alkyl-, alkoxy-, halogenoalkyl- or halogenoalkoxy-substituted phenyl or naphthyl,
R
5
represents hydrogen or alkyl,
R
6
represents alkyl, halogenoalkyl, in each case optionally halogen-, alkyl-, alkenyl-, halogenoalkyl- or halogenoalkenyl-substituted cycloalkyl or cycloalkylalkyl or represents in each case optionally halogen-, alkyl-, alkoxy-, halogenoalkyl- or halogenoalkoxy-substituted phenyl or phenylalkyl,
p, q and r independently of one another each represent 0, 1, 2 or 3, their sum being smaller than 6,
R
7
and R
8
independently of one another each represent hydrogen or alkyl,
G represents cyano, represents an optionally halogen-, alkyl- or halogenoalkyl- and, at the point of linkage, optionally R
9
-substituted 5- or 6-membered heterocycle having 1 to 3 identical or different heteroatoms from the group consisting of nitrogen, oxygen and sulphur or one of the following groups
R
9
represents hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, in each case optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or cycloalkylalkyl or represents arylalkyl which is optionally mono- to pentasubstituted by radicals from the list W
3
,
R
10
represents hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, in each case optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or cycloalkylalkyl or represents arylalkyl which is optionally mono- to pentasubstituted by radicals from the list W
3
,
R
11
and R
12
independently of one another each represent hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, alkoxy, in each case optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or cycloalkylalkyl, represents aryl or arylalkyl, each of which is optionally mono- to pentasubstituted by radicals from the list W
3
, represent —OR
10
or —NR
9
R
10
or together represent an alkylene chain having 2 to 6 members in which optionally one methylene group is replaced by oxygen,
R
13
represents —OR
10
, —NR
9
R
10
or —N(R
9
)—COOR
10
,
R
14
, R
15
and R
16
independently of one another each represent alkyl,
W
1
represents hydrogen, halogen, cyano, formyl, nitro, alkyl, trialkylsilyl,, alkoxy, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, alkylcarbonyl, alkoxycarbonyl, pentafluorothio or, —S(O)
o
R
3
,
W
2
represents halogen, cyano, formyl, nitro, alkyl, trialkylsilyl, alkoxy, halogenoalkyl, halogenoalkoxy, alkylcarbonyl, alkoxycarbonyl, pentafluorothio, —S(O)
o
R
3
or —C(R
9
)═N—R
13
,
W
3
represents halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, dialkylamino, —S(O)
o
R
3
, —COOR
17
or —CONR
18
R
19
,
R
17
represents hydrogen, alkyl, halogenoalkyl, optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or represents phenyl which is optionally mono- to pentasubstituted by radicals from the list W
4
,
R
18
and R
19
independently of one another each represent hydrogen, alkyl alkenyl, halogenoalkyl, halogenoalkenyl, alkoxy, in each case optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or cycloalkylalkyl or represent aryl or arylalkyl, each of which is optionally mono- to pent

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