Cyclic imines as pesticides

Details Cyclic imines as pesticides Cyclic imines as pesticides

2001-12-19

2004-08-03

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S248000, C540S609000, C546S236000

Reexamination Certificate

active

06770595

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The invention relates to novel cyclic imines, to a plurality of processes for their preparation and to their use as pesticides.
BACKGROUND OF THE INVENTION
Only few substituted cyclic &agr;,&agr;′-diphenylimines have been disclosed before three 2,5-diphenyl-1-pyrrolines alkoxy-substituted on 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 in Chem. Ber 96, 93 (1963) and the corresponding 4-propoxy compound in J. Prakt. Chem, Series 4, 1, 57 (1955)] and the unsubstituted 2,6-diphenyl-3,4,5,6-tetrahydropyridine [cf. for example Bull Soc Chim Fr. 1974, 258, and Chem Ber. 116, 3931 (1983)].
Nothing is known about their suitability for use as pesticides.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel cyclic imines of the formula (I)
in which
n represents 1, 2 or 3,
Ar
1
represents the radical
 and
Ar
2
represents the radical
 in which
m represents 0, 1, 2, 3 or 4,
R
1
represents halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, alkoxyalkyl, —S(O)
o
R
6
or —N
7
R
8
,
R
2
and R
3
independently of one another each represent hydrogen, halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, alkoxyalkyl, —S(O)
o
R
6
, or —NR
7
R
8
,
R
4
represents halogen, cyano, trialkylsilyl, —CO—NR
10
R
11
, tetrahydropyranyl or one of the groupings below
(l) —X—A.
(m) —B—Z—D
(n) —Y—E,
R
5
represents hydrogen, halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, alkoxyalkoxy or —S(O)
o
R
6
,
o represents 0, 1 or 2,
R
6
represents alkyl or halogenoalkyl,
R
7
and R
8
independently of one another each represent hydrogen or alkyl, together represent alkylene,
R
10
and R
11
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, alkenylene, 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 having one or more hetero atoms from the group consisting of nitrogen, oxygen and sulphur and containing 1 or 2 aromatic rings, which is 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 WI,
Z represents oxygen or sulphur,
D represents hydrogen, alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, respectively optionally halogen-, alkyl-, alkenyl-, halogenoalkenyl-, phenyl-, styryl-, halogenophenyl- or halogenostyryl-substituted cycloalkyl or cycloalkylalkyl, represents respectively optionally halogen- or alkyl-substituted cycloalkenyl or cycloalkenylalkyl, represents respectively optionally nitro-, halogen-, alkyl-, alkoxy-, halogenoalkyl- or halogenoalkoxy-substituted phenylalkyl, naphthylalkyl, tetrahydronaphthylalkyl or 5- or 6-membered hetarylalkyl having 1 or 2 hetero atoms from the group consisting of nitrogen, oxygen and sulphur, represents —CO—R
12
, —CO—NR
13
R
14
, or represents the grouping
—(CH
2
)
p
—(CR
15
R
16
)
q
—(CH
2
)
r
—G,
or
Z and D together represent optionally nitro-, halogen-, alkyl-, alkoxy-, haloogenoalkyl- or halogenoalkoxy-substituted phenoxyalkyl,
Y represents a direct bond, oxygen, sulphur, carbonyl, carbonyloxy, oxycarbonyl, alkylene, alkenylene, alkenylene, 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, respectively optionally halogen-, alkyl-, alkenyl-, halogenoalkenyl-, phenyl-, styryl-, halogenophenyl- or halogenostyryl-substituted cycloalkyl, represents respectively 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 1 or 2 hetero atoms from the group consisting of nitrogen, oxygen and sulphur, which is optionally mono- to tetrasubstituted by radicals from the list W
2
, or represents the grouping
—(CH
2
)
p
—(CR
15
R
16
)
q
—(CH
2
)
r
—G,
R
12
represents alkyl, alkoxy, alkenyl, alkenyloxy, respectively optionally halogen-, alkyl-, alkenyl-, halogenoalkyl- or halogenoalkenyl-substituted cycloalkyl, cycloalkytoxy or cycloalkylalkyloxy or represents respectively optionally nitro-, halogen-, alkyl-, alkoxy-, halogenoalkyl- or halogenoalkoxy-substituted phenyl or naphthyl,
R
13
represents hydrogen or alkyl,
R
14
represents alkyl, halogenoalkyl, respectively optionally halogen-, alkyl-, alkenyl-, halogenoalkyl- or halogenoalkenyl-substituted cycloalkyl or cycloalkylalkyl or represents respectively 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
15
and R
16
independently of one another each represent hydrogen or alkyl,
G represents cyano, represents a 5- or 6-membered heterocycle having 1 to 3 identical or different hetero atoms from the group consisting of nitrogen, oxygen and sulphur, which is optionally substituted by halogen, alkyl or halogenoalkyl and, at the attachment point, optionally by the radical R
17
, or represents one of the groupings below
R
17
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
18
represents hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, respectively optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or cycloalkylalkyl or represents arylalkyl which is optionally mono- to pentasubstituted by radicals from the list W
1
,
R
19
and R
20
independently of one another each represent hydrogen, alkyl, alkenyl, haloogenoalkyl, halogenoalkenyl, alkoxy, respectively optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or cycloalkylalkyl, represent aryl or arylalkyl, each of which is optionally mono- to pentasubstituted by radicals from the list W
3
, represent —OR
18
or —NR
17
R
18
or together represent an alkylene chain having 2 to 6 members in which one methylene group is optionally replaced by oxygen,
R
21
represents —OR
18
, —NR
17
R
18
or —N(R
17
)—COOR
18
,
R
22
, R
23
and R
24
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)OR
6
,
W
2
represents halogen, cyano, formyl, nitro, alkyl, trialkylsilyl, alkoxy, halogenoalkyl, halogenoalkoxy, alkylcarbonyl, alkoxycarbonyl, pentafluorothio, —S(O)
o
R
6
or —C(R
17
)═N—R
21
,
W
3
represents halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, dialkylamino —S(O)
o
R
6
, —COOR
25
or —CONR
26
R
27
,
R
25
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
26
and R
27
independently of one another each represent hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, alkoxy, respectively optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or cycloalkylalkyl or represent aryl or arylalkyl, each of which is optionally mono- to penta-substituted by radicals from the list W
4
, represent —OR
22
or —NR
23
R
24
or together represent an alkylene chain having 2

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