Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-10-12
2002-07-02
Gerstl, Robert (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S237000
Reexamination Certificate
active
06414000
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel substituted oxazoline derivatives, to processes for their preparation and to their use for controlling animal pests.
BACKGROUND OF THE INVENTION
It is already known that oxazoline derivatives have insecticidal and acaracidal activity (cf. for example EP-A 0 432 661, EP-A 0 696 584, WO-A 95/04726, WO-A 96/11190 or WO-A 96/22283), for example. 2-(2,6-difluorophenyl)-4-(4′-methoxy- or isopropoxy biphenyl-4-yl)-1,3-oxazoline (cf. EP-A 0 432 661).
However, the efficacy and/or the duration of action of these known compounds, in particular against certain organisms or at low application concentrations, is not entirely satisfactory in all areas of use.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel substituted oxazoline derivatives of the formula (I)
in which the radicals A, B, Q and R are each as defined in Table 1 below:
TABLE 1
Comp.
No.
A
B
Q
R
1
F
F
H
2
Cl
H
H
3
F
Cl
H
—CH
2
—C(CH
3
)═N—O—CH(CH
3
)C
2
H
5
4
F
Cl
H
—C(CH
3
)
2
—C(CH
3
)═N—O—C
3
H
7
-i
5
Br
H
H
—C
3
H
7
-i
6
F
F
H
—CO—NH—C
3
H
7
-i
7
F
F
H
—CF═CF—CH═CH
2
8
F
F
H
—CH
2
—CH═NOCH
3
9
H
Cl
H
—C
3
H
7
-n
10
H
Cl
H
11
H
Cl
H
—C
3
H
7
-i
12
H
Cl
H
—C
4
H
9
-n
13
H
Cl
H
14
H
Cl
H
—CH
2
—C
3
H
7
-i
15
F
F
H
—CH
2
CH
2
—CH═CF
2
16
F
F
H
—CH
2
—CH═NOC
2
H
5
17
F
F
H
18
F
F
H
19
F
F
H
20
F
F
H
21
F
F
H
22
I
H
H
23
F
F
H
24
F
F
H
25
F
F
H
26
F
F
H
27
F
Cl
H
—C
3
H
7
-i
28
F
F
H
29
F
Cl
H
—C
3
H
7
-n
30
F
Cl
H
—CH
2
—C
3
H
7
-i
31
F
F
H
32
F
F
H
33
F
F
H
34
F
Cl
H
—C
4
H
9
-n
35
F
F
H
—CH(CH
3
)—CH═NOCH
3
36
F
F
H
—CH(CH
3
)—C≡CH
37
Cl
H
H
—CH(CH
3
)—C≡CH
38
Cl
F
H
39
Cl
H
H
—CH
2
—C
3
H
7
-i
40
Cl
Cl
H
41
Cl
Cl
H
—C
3
H
7
-i
42
F
F
H
43
F
F
Cl
44
F
F
Cl
45
Cl
H
Cl
46
F
F
H
47
F
Cl
H
48
F
Cl
H
49
F
Cl
H
50
F
F
H
51
F
F
H
52
F
F
H
53
F
F
H
—C(CH
3
)
2
—CH═NOC
2
H
5
54
F
Cl
H
55
F
F
H
56
F
F
H
57
F
F
H
—C(CH
3
)
2
—CH═NOCH
3
58
Cl
H
H
59
F
F
H
60
F
F
H
61
Cl
H
Cl
62
Cl
H
Cl
63
F
F
Cl
64
F
F
Cl
65
Cl
Cl
H
—CH(CH
3
)—COCH
3
66
Cl
Cl
H
67
Cl
Cl
H
68
Br
H
H
—CH(CH
3
)—COCH
3
69
Cl
H
H
CF
3
70
CH
3
O—
H
H
CF
3
71
CF
3
H
H
CF
3
72
CH
3
SO
2
—
H
H
CF
3
73
C
2
H
5
O—
H
H
CF
3
74
i-C
3
H
7
O—
H
H
CF
3
75
NO
2
H
H
CF
3
76
CH
3
O—
F
H
CF
3
77
F
NH
2
H
CF
3
78
CH
3
S—
H
H
CF
3
79
i-C
3
H
7
S—
H
H
CF
3
80
C
2
H
5
S—
H
H
CF
3
81
C
2
H
5
O—
F
H
CF
3
82
C
2
H
5
CH(CH
3
)O—
F
H
CF
3
83
C
2
H
5
CH(CH
3
)O—
C
2
H
5
CH(CH
3
)O—
H
CF
3
84
i-C
3
H
7
CH
2
O—
F
H
CF
3
85
i-C
3
H
7
CH
2
O—
i-C
3
H
7
CH
2
O—
H
CF
3
86
C
2
H
5
H
H
CF
3
87
H
H
CF
3
88
CH
3
O
H
H
C
3
H
7
-i
89
Br
H
H
CF
3
90
I
H
H
CF
3
91
Br
H
H
—CH(CH
3
)—CH(OH)CH
3
92
Br
H
H
—CH(CH
3
)—C(CH
3
)═NOCH
3
93
I
H
H
C
3
H
7
-i
94
I
H
H
95
Br
H
H
—CH
2
—CH═CH
2
96
Br
H
H
—CH
2
—C≡CH
97
F
H
Cl
98
F
H
Cl
99
F
Cl
H
100
F
H
H
—CH(CH
3
)—COCH
3
101
F
H
H
102
F
F
H
—C(CH
3
)
2
—CHO
103
F
H
Cl
104
F
Cl
H
105
F
H
Cl
106
F
H
Cl
107
F
H
H
—C
3
H
7
-i
108
F
H
H
—CH
2
—C
3
H
7
-i
109
F
H
H
110
F
H
H
111
F
H
H
112
F
Cl
H
—CH
2
—CH═NOCH
3
113
F
Cl
H
—CH
2
—CH═NOC
2
H
5
114
F
F
Cl
—CH
2
—CH═NOCH
3
115
F
F
Cl
—CH
2
—CH═NOC
2
H
5
116
Cl
H
Cl
—CH
2
—CH═NOCH
3
117
Cl
H
Cl
—CH
2
—CH═NOC
2
H
5
118
F
H
Cl
—CH
2
CF
3
119
F
F
CH
3
—CH
2
CF
3
120
CF
3
CH
2
O—
F
CH
3
—CH
2
CF
3
121
Cl
H
—CH
2
—
—CH
2
CF
3
CH═CH
2
122
Cl
H
CH
3
—CH
2
CF
3
123
F
F
C
2
H
5
CH
2
CF
3
124
Cl
H
H
—CH
2
CF
3
125
F
F
H
126
F
F
H
—CH
2
—CF
2
—CHF
2
127
F
F
H
—(CH
2
)
3
—CF
2
—CF
3
The substituted oxazoline derivatives of the formula (I) can be present as optical and/or geometrical isomers, which depends, among other things, on the substituents. The present invention provides both the isomer mixtures and the pure isomers.
Furthermore, it was found that the substituted oxazoline derivatives of the formula (I)/(Table 1) are obtained when hydroxybiphenyloxazolines of the formula (II)
in which
A, B and Q are each as defined above in Table 1 are reacted with a compound of the formula (III)
M—R (III)
in which
R is in each case as defined above in Table 1 and
M is a leaving group,
if appropriate in the presence of a base and/or catalyst and if appropriate in the presence of a diluent.
Furthermore, it was found that the novel substituted oxazoline derivatives of the formula (I) are highly suitable for controlling animal pests, in particular insects, arachnids, and nematodes, encountered in agriculture, in forestry, in the protection of stored products and of materials, and in the hygiene sector.
The formula (I)/Table 1 provides a general definition of the compounds according to the invention. Preferred compounds are listed in Table 1 a below:
TABLE IA
(I)
Cpd.No.
A
B
Q
R
1A
F
F
H
2A
Cl
H
H
3A
F
Cl
H
—CH
2
—C(CH
3
)═N—O—CH(CH
3
)C
2
H
5
4A
F
Cl
H
—C(CH
3
)
2
—C(CH
3
)═N—O—C
3
H
7
-i
5A
Br
H
H
—C
3
H
7
-i
Using, for example, 2-(2,6-difluorophenyl)-4-(4′-hydroxybiphenyl-4-yl)1,3-oxazoline and 4-trifluoromethylbenzyl chloride as starting materials for carrying out the process according to the invention, the course of the reaction can be represented by the following equation:
Starting compounds of formula (II) are known (cf. for example EP-A 432 661 and EP-A 696 584) and/or can be obtained, as described therein, in a generally well-known manner by converting an amide-derivative of the formula (IV)
in which
A and B are each as defined above in Table 1 and
R′ represents C
1
-C
4
-alkyl, preferably methyl or ethyl,
with biphenyl derivatives of the formula (V)
in which
Q is as defined above in Table 1 and
R″ represents C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy, preferably methyl, ethyl, methoxy or ethoxy,
in the presence of an acid catalyst such as, for example, hydrofluoric acid, sulphuric acid, acetic acid or aluminium chloride and in the presence of a diluent such as, for example, methylene chloride or acetonitrile, at temperatures between 0° C. and 80° C.;
cyclizing the resulting compounds of the formula (VI)
in which
A, B, Q and R″ are each as defined above
in the presence of a base such as, for example, aqueous sodium hydroxide solution, if appropriate in the presence of a catalyst such as, for example, ammonium compounds and if appropriate in the presence of a diluent such as, for example, dimethylformamide, at temperatures between 0° C. and 100° C. to give biphenyloxazolines of the formula (VII)
in which
A, B, Q and R″ are each as defined above,
and hydrolysing these in a customary manner in the presence of the diluent such as, for example, methanol at room temperature, using, for example, aqueous ammonia, it being possible, if appropriate, to carry out cyclization and hydrolysis in a one-part reaction.
Not known and likewise part of the subject matter of this application is the compound (II-1) of the formula (II).
The amide derivatives of the formula (IV) are known (cf. for example EP-A 594 179) and/or can be obtained by methods described therein.
The formula (III) provides a general definition of the compounds also to be used as starting materials in the process according to the invention. In the formula (III), M represents a customary leaving group, preferably halogen, in particular chlorine or bromine; alkylsulphonyloxy, in particular methylsulphonyloxy; or optionally substituted arylsulphonyloxy, in particular phenylsulphonyloxy, p-chlorophenylsulphonyloxy or tolylsulphonyloxy.
The compounds of the formula (III) are generally known compounds of organic chemistry.
Suitable diluents for carrying out the process according to the invention are all customary solvents. Preference is given to using optionally halogenated aromatic or aliphatic hydrocarbons, ketones, nitrites and amides. Examples include toluene, acetone, acetonitrile, dimethylformamide and dimethylacetamide.
Suitable bases for carrying out the process according to the invention are all customary inorganic and organic bases. Examples include tertiary amines such as
Erdelen Christoph
Kraatz Udo
Krämer Wolfgang
Lantzsch Reinhard
Marhold Albrecht
Bayer Aktiengesellschaft
Gerstl Robert
Gil Joseph C.
Zurcher Jackie Ann
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