2-(2-methylphenyl)-3,4-dihydro-2H-pyrrole derivatives

Details 2-(2-methylphenyl)-3,4-dihydro-2H-pyrrole derivatives 2-(2-methylphenyl)-3,4-dihydro-2H-pyrrole derivatives

2000-11-13

2003-10-14

Stockton, Laura L. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S429000, C548S525000, C548S526000, C548S527000, C548S565000

Reexamination Certificate

active

06632833

ABSTRACT:

This application is a 317 of PCT/EP99/03062 filed May 5, 1999.
The invention relates to novel 2-(2-methylphenyl)-3,4-dihydro-2H-pyrrole derivatives, to a plurality of processes for their preparation and to their use as pesticides.
Hitherto, only few substituted cyclic &agr;,&agr;′-diphenylimines are known: 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-methoxy-phenyl)-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 the 2,6-diphenyl-3,4,5,6-tetrahydropyridine, which is not substituted any further [cf., for example, Bull. Soc. Chim. Fr. 1974, 258 and Chem. Ber. 116, 3931 (1983)].
Nothing is known concerning their suitability for use as pesticides.
This invention, accordingly, provides novel 2-(2-methylphenyl)-3,4-dihydro-2H-pyrrole derivatives of the formula (I)
in which
Ar represents the radical
 in which
m represents 0, 1, 2, 3 or 4,
R
1
represents hydrogen, F, Cl, Br, cyano, trialkylsilyl, —CO—NR
4
R
5
, tetrahydropyranyl or represents one of the following groupings
(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
,
with the proviso that R
1
does not represent hydrogen if m=1 and R
2
=iodine.
o represents 0, 1 or 2,
R
3
represents alkyl or halogenoalkyl,
R
4
and R
5
independently of one another each represent hydrogen, alkyl, halogenoalkyl or represent phenyl or phenylalkyl, each of which is optionally mono- or polysubstituted by radicals from the list W
1
,
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 halogenostyryl-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
6
, —CO—NR
7
R
8
or represents the grouping
—(CH
2
)
p
—(CR
9
R
10
)
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
9
R
1
)
q
—(CH
2
)
r
10
—G,
R
6
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
7
represents hydrogen or alkyl,
R
8
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 and greater than 1,
R
9
and R
10
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
11
-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
(a) —CO—R
11
(b) —CO—OR
12
(c) —CO—NR
13
R
14
(d) —CS—NR
13
R
14
R
11
represents hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or represents phenyl which is optionally mono- to pentasubstituted by alkylcarbonylamino, alkylcarbonylalkylamino and/or radicals from the list W
3
,
R
12
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
13
and R
14
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
12
or —NR
11
R
12
or together represent an alkylene chain having 2 to 6 members in which optionally one methylene group is replaced by oxygen,
R
15
represents —OR
12
, —NR
11
R
12
or —N(R
11
)—COOR
12
,
R
16
, R
17
and R
18
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
11
)═N—R
15
,
W
3
represents halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, dialkylamino, —S(O)
o
R
3
, —COOR
19
or —CONR
20
R
21
,
R
19
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
20
and R
21
independently of one another each represent hydrogen, alkyl, alkenyl, halogenoalkyl, haligenoalkenyl, 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 pentasubstituted by radicals from the list W
4
, represent —OR
16
or —NR
17
R
18
or together represent an alkylene chain having 2 to 6 members in which optionally one methylene group is replaced by oxygen, and
W
4
represents halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, dialkylamino, alkoxycar

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