Fungicides containing pyrrolidones as their active agents

This application is a 371 of PCT/EP99/08379 Nov. 12, 1999.

The present invention relates to novel agrochemical compositions having fungicidal action comprising pyrrolidones as active compounds, and to their use in the treatment of plants and in agriculture.

The present invention provides compositions comprising as active compounds compounds of the formula I

where:

R

1

is hydrogen, C

1

-C

6

-alkyl, C

1

-C

6

-alkylcarbonyl, formyl or C

1

-C

6

-haloalkylcarbonyl;

R

2

is hydrogen, C

1

-C

6

-alkyl or C

1

-C

6

-haloalkyl;

R

3

-R

12

are hydrogen, halogen, C

1

-C

6

-cycloalkyl, C

1

-C

6

-alkyl, C

1

-C

6

-haloalkyl, C

1

-C

6

-alkoxy, C

1

-C

6

-haloalkoxy, C

1

-C

6

-alkylsulfonyl, C

1

-C

6

-haloalkylsulfonyl, formyl, C

1

-C

6

-alkylcarbonyl, cyano, C

1

-C

6

-alkylthio or phenyl, which may be unsubstituted or substituted by halogen atoms, C

1

-C

6

-alkyl or C

1

-C

6

-haloalkyl groups, and their agriculturally useful salts.

Some of the compounds of the formula I are known from the literature (M. Augustin and P. Reinemann, Z. Chem. Volume 13, pp. 214-216 (1973), and/or they are commercially available. These are the following compounds:

1-anilino-3-phenylpyrrole-2,5-dione, 1-anilino-3-p-tolylpyrrole-2,5-dione, 1-(N-methylanilino)-3-p-tolylpyrrole-2,5-dione, 1-anilino-3-(3-chlorophenyl)pyrrole-2,5-dione, 1-anilino-3-(4-chlorophenyl)pyrrole-2,5-dione, 1-anilino-3-(4-bromophenyl)pyrrole-2,5-dione, 3-(4-chlorophenyl)-1-(N-methylanilino)pyrrole-2,5-dione, 1-(4-chloroanilino)-3-p-tolylpyrrole-2,5-dione, 3-(4-bromophenyl)-1-(4-methylanilino)pyrrole-2,5-dione, 1-(4-chloroanilino)-3-(4-chlorophenyl)pyrrole-2,5-dione, 1-anilino-3-(3,4-dichlorophenyl)pyrrole-2,5-dione, 3-(4-bromophenyl)-1-(4-methoxyanilino)pyrrole-2,5-dione, 3-(4-chlorophenyl)-1-(3,4-dichloroanilino)pyrrole-2,5-dione, 3-(4-methoxyphenyl)-1-(N-methylanilino)pyrrole-2,5-dione, 1-anilino-3-(4-methoxyphenyl)pyrrole-2,5-dione, 1-(4-chloroanilino)-3-(4-methoxyphenyl)pyrrole-2,5-dione, 1-(4-methoxyanilino)-3-(4-methoxyphenyl)pyrrole-2,5-dione, 1-(2-methoxyanilino)-3-(4-methoxyphenyl)pyrrole-2,5-dione, 1-(4-fluoroanilino)-3-(4-chlorophenyl)pyrrole-2,5-dione, 3-(4-chlorophenyl)-1-(4-methylanilino)pyrrole-2,5-dione, 1-(4-methylanilino)-3-phenylpyrrole-2,5-dione, 3-(4-chlorophenyl)-1-(2,4-dichloroanilino)pyrrole-2,5-dione, 1-(2,4-dichloroanilino)-3-phenylpyrrole-2,5-dione, 1-(2,4-dichloroanilino)-3-(4-methoxyphenyl)pyrrole-2,5-dione.

A fungicidal activity of these compounds has hitherto not been described.

Surprisingly, it has been found that compounds of the formula I have fungicidal activity. They are suitable for controlling harmful fungi in the treatment of plants, and also for the therapeutic treatment of diseases in humans caused by harmful fungi, and for veterinary treatment in mammals.

Compounds of the formula I can be prepared by the same method as that described in the literature (Z. Chem. Volume 13, pp. 214-216 (1973)). The starting materials are either known from the literature or commercially available.

In the definition of the substituents R

1

to R

12

, the given terms are collective terms for a group of compounds.

In each case, halogen is fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.

Examples of other meanings are:

C

1

-C

6

-alkyl: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl, in particular ethyl;

C

1

-C

6

-haloalkyl: a C

1

-C

6

-alkyl radical as mentioned above such as partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example trichloromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2-fluoropropyl, 3-fluoropropyl, 2-chloropropyl or 3-chloropropyl, in particular 2-fluoroethyl or 2-chloroethyl;

C

1

-C

6

-alkoxy: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, in particular methoxy or ethoxy;

C

3

-C

8

-cycloalkyl: for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl;

halo-C

1

-C

6

-alkoxy: a C

1

-C

6

-alkoxy radical as mentioned above which is substituted by fluorine, chlorine or bromine;

C

1

-C

6

-alkylcarbonyl: a carbonyl group which is substituted by a C

1

-C

6

-alkyl radical as mentioned above, such as, for example, acetyl, propionyl, butyryl;

halo-C

1

-C

6

-alkylcarbonyl: a C

1

-C

6

-alkylcarbonyl radical as mentioned above which is substituted by fluorine, chlorine or bromine;

C

1

-C

6

-alkylsulfonyl: a sulfonyl group which is substituted by a C

1

-C

6

-alkyl radical as mentioned above;

halo-C

1

-C

6

-alkylsulfonyl: a C

1

-C

6

-alkylsulfonyl radical as mentioned above which is substituted by fluorine, chlorine or bromine;

C

1

-C

6

-alkylthio: a sulfur atom which is substituted by a C

1

-C

6

-alkyl radical as mentioned above;

an unsubstituted or substituted phenyl radical: a phenyl radical which is mono- or polysubstituted. The substituents can be chosen at will, for example the following: halogen atoms, C

1

-C

6

-alkyl or halo-C

1

-C

6

-alkyl.

For the purpose of the present invention, the compounds listed under items 1-4 below are preferred with a view to the definitions of substituents mentioned, in each case on their own or in combination with one another:

1. Compounds of the formula 1, where R

1

is as defined below: hydrogen, methyl, ethyl or formyl, in particular hydrogen or methyl.

2. Compounds according to 1, where R

2

is as defined below: hydrogen, methyl, ethyl, trifluoromethyl, in particular hydrogen.

3. Compounds according to 1 or 2, where R

3

-R

12

are as defined below: hydrogen, fluorine, chlorine, methyl, ethyl, propyl, butyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, methoxy, methylthio, cyano.

4. Compounds according to 1 to 3, where at least two of the radicals R

8

-R

12

and in addition at least two of the radicals R

3

-R

7

are hydrogen and the others are hydrogen, fluorine, chlorine, methyl, ethyl, propyl, butyl, trifluoromethyl, trifluoromethoxy or difluoromethoxy.

The two phenyl rings are preferably unsubstituted (R

3

—R

12

=H) or preferably mono-, di- or trisubstituted, suitable substituents being mainly the following: C

1

-C

6

-alkyl, halogen, halo-C

1

-C

6

-alkyl, halo-C

1

-C

6

-alkoxy, in particular methyl, isopropyl, fluorine, chlorine, trifluoromethyl or trifluoromethoxy.

In general, the abovementioned compounds have been found to be particularly effective.

For the purpose of the present invention, for example the following compounds in Table 1 are suitable fungicidally active compounds:

TABLE 1

Phys.

No.

R

1

R

2

R

3

R

4

Data

1)

H

H

phenyl

phenyl

2)

H

H

phenyl

4-methylphenyl

3)

H

H

phenyl

2,4-dichloro-

phenyl

4)

H

H

4-methylphenyl

phenyl

5)

H

H

4-methylphenyl

4-chlorophenyl

6)

H

H

4-methoxy-

phenyl

phenyl

7)

H

H

4-methoxy-

4-methoxyphenyl

phenyl

8)

H

H

4-methoxy-

2-methoxyphenyl

phenyl

9)

H

H

4-methoxy-

4-chlorophenyl

phenyl

10)

H

H

4-methoxy-

2,4-dichloro-

phenyl

phenyl

11)

H

H

3-chlorophenyl

phenyl

12)

H

H

3,4-dichloro-

phenyl

m.p.

phenyl

208-

210° C.

13)

H

H

4-chlorophenyl

phenyl

14)

H

H

4-chlorophenyl

4-chlorophenyl

m.p.

192-

193° C.

15)

H

H

4-Chlorophenyl

3,4-dichloro-

phenyl

16)

H

H

4-chlorophenyl

2,4-dichloro-

phenyl

17)

H

H

4-chlorophenyl

4-fluorophenyl

18)

H

H

4-chlorophenyl

4-methylphenyl

19)

H

H

4-bromophenyl

4-methoxyphenyl

20)

H

H

4-bromophenyl

4-methylphenyl

21)

Methyl

H

4-methylphenyl

phenyl

22)

Methyl

H

4-methoxy-

phenyl

phenyl

23)

Methyl

H

4-chlorophenyl

phenyl

m.p.

149-

150° C.

24)

Acetyl

H

phenyl

phenyl

25)

Tri-

H

phenyl

phenyl

fluoro-

acetyl

26)

H

H

phenyl

4-isopropyl-

1H-NMR

phenyl

(DMSO-

d

6

): δ =

1.15 (d);

2.78 (m);

6.65 (d);

7.05 (d);

7.40 (s);

7.57 (m);

8.05 (m);

8.30 (s).

27)

H

H

phenyl

4-fluorophenyl

28)

H

H

phenyl

3-fluorophenyl

29)

H

H

phenyl

2-fluorophenyl

30)

H

H

phenyl

2,3,5,6-tetra-

m.p.

fluorophenyl

123-

125° C.

31)

H

H

phenyl

4-trifluoro-

m.p.

methylphenyl

211-

214° C.

32)

H

H

phenyl

3-trifluoro-

methylphenyl

33)

H

H

phenyl

4-methyl-

m.p.

sulphonylphenyl

168-

170° C.

34)

H

H

phenyl

4-chlorophenyl

m.p.

175-

177° C.

35)

H

H

phenyl

3-chlorophenyl

m.p.

192-

194° C.

36)

H

H

phenyl

2-chlorophenyl

m.p.

175-

177° C.

37)

H

H

phenyl

3,5-dichloro-

m.p.

phenyl

234-

236° C.

38)

H

H

phenyl

4-(trifluoro-

m.p.

methoxy)phenyl

174-

176° C.

39)

H

H

phenyl

3-(trifluoro-

methoxy)phenyl

40)

H

H

phenyl

4-(difluoro-

methoxy)phenyl

41)

H

H

phenyl

3-(difluoro-

methoxy)phenyl

42)

H

H

phenyl

4-cyanophenyl

43)

H

H

4-chlorophenyl

4-trifluoro-

m.p.

methylphenyl

206-

208° C.

44)

H

H

4-chlorophenyl

3-trifluoro-

methylphenyl

45)

H

H

4-chlorophenyl

2-chlorophenyl

m.p.

185-

187° C.

46)

H

H

4-chlorophenyl

3-chlorophenyl

m.p.

178-

180° C.

47)

H

H

4-chlorophenyl

4-trifluoro-

methoxyphenyl

48)

H

H

4-chlorophenyl

3-trifluoro-

methoxyphenyl

49)

H

H

4-chlorophenyl

4-difluoro-

methoxyphenyl

50)

H

H

4-chlorophenyl

3-difluoro-

methoxyphenyl

51)

H

H

4-fluorophenyl

phenyl

m.p.

174-

176° C.

52)

H

H

4-fluorophenyl

4-ethylphenyl

53)

H

H

4-fluorophenyl

4-methylphenyl

54)

H

H

4-fluorophenyl

2-methylphenyl

55)

H

H

4-fluorophenyl

3-methylphenyl

56)

H

H

4-fluorophenyl

4-fluorophenyl

m.p.

183-

186° C.

57)

H

H

4-fluorophenyl

2,4-difluoro-

phenyl

58)

H

H

4-fluorophenyl

4-chlorophenyl

59)

H

H

4-fluorophenyl

3-chlorophenyl

60)

H

H

4-fluorophenyl

2-chlorophenyl

61)

H

H

4-fluorophenyl

4-chloro-2-

methoxyphenyl

62)

H

H

4-fluorophenyl

4-trifluoro-

methylphenyl

63)

H

H

4-fluorophenyl

2-trifluoro-

methylphenyl

64)

H

H

4-fluorophenyl

3-trifluoro-

methylphenyl

65)

H

H

4-fluorophenyl

4-(trifluoro-

methoxy)phenyl

66)

H

H

4-fluorophenyl

3-(trifluoro-

methoxy)phenyl

67)

H

H

4-fluorophenyl

4-(difluoro-

methoxy)phenyl

68)

H

H

4-fluorophenyl

3-(difluoro-

methoxy)phenyl

69)

H

H

4-fluorophenyl

4-cyanophenyl

70)

H

H

3-fluorophenyl

phenyl

71)

H

H

3-fluorophenyl

4-ethylphenyl

72)

H

H

3-fluorophenyl

4-methylphenyl

73)

H

H

3-fluorophenyl

2-methylphenyl

74)

H

H

3-fluorophenyl

3-methylphenyl

75)

H

H

3-fluorophenyl

4-fluorophenyl

76)

H

H

3-fluorophenyl

2,4-difluoro-

phenyl

77)

H

H

3-fluorophenyl

4-chlorophenyl

78)

H

H

3-fluorophenyl

3-chlorophenyl

79)

H

H

3-fluorophenyl

2-chlorophenyl

80)

H

H

3-fluorophenyl

4-chloro-2-

methoxyphenyl

81)

H

H

3-fluorophenyl

4-trifluoro-

methylphenyl

82)

H

H

3-fluorophenyl

2-trifluoro-

methylphenyl

83)

H

H

3-fluorophenyl

3-trifluoro-

methylphenyl

84)

H

H

3-fluorophenyl

4-(trifluoro-

methoxy)phenyl

85)

H

H

3-fluorophenyl

3-(trifluoro-

methoxy)phenyl

86)

H

H

3-fluorophenyl

4-(difluoro-

methoxy)phenyl

87)

H

H

3-fluorophenyl

3-(difluoro-

methoxy)phenyl

88)

H

H

3-fluorophenyl

4-cyanophenyl

89)

H

H

2-fluorophenyl

phenyl

90)

H

H

2-fluorophenyl

4-ethylphenyl

91)

H

H

2-fluorophenyl

4-methylphenyl

92)

H

H

2-fluorophenyl

2-methylphenyl

93)

H

H

2-fluorophenyl

3-methylphenyl

94)

H

H

2-fluorophenyl

4-fluorophenyl

95)

H

H

2-fluorophenyl

2,4-difluoro-

phenyl

96)

H

H

2-fluorophenyl

4-chlorophenyl

97)

H

H

2-fluorophenyl

3-chlorophenyl

98)

H

H

2-fluorophenyl

2-chlorophenyl

99)

H

H

2-fluorophenyl

4-chloro-2-

methoxyphenyl

100)

H

H

2-fluorophenyl

4-trifluoro-

methylphenyl

101)

H

H

2-fluorophenyl

2-trifluoro-

methylphenyl

102)

H

H

2-fluorophenyl

3-trifluoro-

methylphenyl

103)

H

H

2-fluorophenyl

4-(trifluoro-

methoxy)phenyl

104)

H

H

2-fluorophenyl

3-(trifluoro-

methoxy)phenyl

105)

H

H

2-fluorophenyl

4-(difluoro-

methoxy)phenyl

106)

H

H

2-fluorophenyl

3-(difluoro-

methoxy)phenyl

107)

H

H

2-fluorophenyl

4-cyanophenyl

108)

H

H

2,4-difluoro-

phenyl

phenyl

109)

H

H

2,4-difluoro-

4-ethylphenyl

phenyl

110)

H

H

2,4-difluoro-

4-methylphenyl

phenyl

111)

H

H

2,4-difluoro-

2-methylphenyl

phenyl

112)

H

H

2,4-difluoro-

3-methylphenyl

phenyl

113)

H

H

2,4-difluoro-

4-fluorophenyl

phenyl

114)

H

H

2,4-difluoro-

2,4-difluoro-

phenyl

phenyl

115)

H

H

2,4-difluoro-

4-chlorophenyl

phenyl

116)

H

H

2,4-difluoro-

3-chlorophenyl

phenyl

117)

H

H

2,4-difluoro-

2-chlorophenyl

phenyl

118)

H

H

2,4-difluoro-

4-chloro-2-

phenyl

methoxyphenyl

119)

H

H

2,4-difluoro-

4-trifluoro-

phenyl

methylphenyl

120)

H

H

2,4-difluoro-

2-trifluoro-

phenyl

methylphenyl

121)

H

H

2,4-difluoro-

3-trifluoro-

phenyl

methylphenyl

122)

H

H

2,4-difluoro-

4-(trifluoro-

phenyl

methoxy)phenyl

123)

H

H

2,4-difluoro-

3-(trifluoro-

phenyl

methoxy)phenyl

124)

H

H

2,4-difluoro-

4-(difluoro-

phenyl

methoxy)phenyl

125)

H

H

2,4-difluoro-

3-(difluoro-

phenyl

methoxy)phenyl

126)

H

H

2,4-difluoro-

4-cyanophenyl

phenyl

127)

H

H

4-trifluoro-

phenyl

methylphenyl

128)

H

H

4-trifluoro-

4-ethylphenyl

methylphenyl

129)

H

H

4-trifluoro-

4-methylphenyl

methylphenyl

130)

H

H

4-trifluoro-

2-methylphenyl

methylphenyl

131)

H

H

4-trifluoro-

3-methylphenyl

methylphenyl

132)

H

H

4-trifluoro-

4-fluorophenyl

methylphenyl

133)

H

H

4-trifluoro-

2,4-difluoro-

methylphenyl

phenyl

134)

H

H

4-trifluoro-

4-chlorophenyl

methylphenyl

135)

H

H

4-trifluoro-

3-chlorophenyl

methylphenyl

136)

H

H

4-trifluoro-

2-chlorophenyl

methylphenyl

137)

H

H

4-trifluoro-

4-chloro-2-

methylphenyl

methoxyphenyl

138)

H

H

4-trifluoro-

4-trifluoro-

methylphenyl

methylphenyl

139)

H

H

4-trifluoro-

2-trifluoro-

methylphenyl

methylphenyl

140)

H

H

4-trifluoro-

3-trifluoro-

methylphenyl

methylphenyl

141)

H

H

4-trifluoro-

4-(trifluoro-

methylphenyl

methoxy)phenyl

142)

H

H

4-trifluoro-

3-(trifluoro-

methylphenyl

methoxy)phenyl

143)

H

H

4-trifluoro-

4-(difluoro-

methylphenyl

methoxy)phenyl

144)

H

H

4-trifluoro-

3-(difluoro-

methylphenyl

methoxy)phenyl

145)

H

H

4-trifluoro-

4-cyanophenyl

methylphenyl

146)

H

H

3,4-dichloro-

4-fluorophenyl

1H-NMR

phenyl

(DMSO-

d

6

): δ =

6.80 (m);

7.00 (t);

7.57 (s);

7.83 (d);

8.05 (d);

8.35 (s);

8.40 (s).

147)

H

H

3,4-(methyl-

phenyl

m.p.

enedi-

188-

oxy)phenyl

190° C.

148)

H

H

3-trifluoro-

phenyl

methylphenyl

149)

H

H

3-trifluoro-

4-ethylphenyl

methylphenyl

150)

H

H

3-trifluoro-

4-methylphenyl

methylphenyl

151)

H

H

3-trifluoro-

2-methylphenyl

methylphenyl

152)

H

H

3-trifluoro-

3-methylphenyl

methylphenyl

153)

H

H

3-trifluoro-

4-fluorophenyl

methylphenyl

154)

H

H

3-trifluoro-

2,4-difluoro-

methylphenyl

phenyl

155)

H

H

3-trifluoro-

4-chlorophenyl

methylphenyl

156)

H

H

3-trifluoro-

3-chlorophenyl

methylphenyl

157)

H

H

3-trifluoro-

2-chlorophenyl

methylphenyl

158)

H

H

3-trifluoro-

4-chloro-2-

methylphenyl

methoxyphenyl

159)

H

H

3-trifluoro-

4-trifluoro-

methylphenyl

methylphenyl

160)

H

H

3-trifluoro-

2-trifluoro-

methylphenyl

methylphenyl

161)

H

H

3-trifluoro-

3-trifluoro-

methylphenyl

methylphenyl

162)

H

H

3-trifluoro-

4-(trifluoro-

methylphenyl

methoxy)phenyl

163)

H

H

3-trifluoro-

3-(trifluoro-

methylphenyl

methoxy)phenyl

164)

H

H

3-trifluoro-

4-(difluoro-

methylphenyl

methoxy)phenyl

165)

H

H

3-trifluoro-

3-(difluoro-

methylphenyl

methoxy)phenyl

166)

H

H

3-trifluoro-

4-cyanophenyl

methylphenyl

167)

methyl

H

phenyl

phenyl

1H-NMR

(CDCl

3

):

δ = 3.38

(s); 6.80

(m); 6.90

(t); 7.72

(m); 7.50

(m); 7.97

(m).

168)

methyl

H

phenyl

4-methylphenyl

169)

methyl

H

phenyl

2,4-dichloro-

phenyl

170)

methyl

H

4-methylphenyl

4-chlorophenyl

171)

methyl

H

4-methoxy-

4-methoxyphenyl

phenyl

172)

methyl

H

4-methoxy-

2-methoxyphenyl

phenyl

173)

methyl

H

4-methoxy-

4-chlorophenyl

phenyl

174)

methyl

H

4-methoxy-

2,4-dichloro-

phenyl

phenyl

175)

methyl

H

3-chlorophenyl

phenyl

176)

methyl

H

3,4-dichloro-

phenyl

phenyl

177)

methyl

H

4-chlorophenyl

4-chlorophenyl

178)

methyl

H

4-chlorophenyl

3,4-dichloro-

phenyl

179)

methyl

H

4-chlorophenyl

2,4-dichloro-

phenyl

180)

methyl

H

4-chlorophenyl

4-fluorophenyl

181)

methyl

H

4-chlorophenyl

4-methylphenyl

182)

methyl

H

4-bromophenyl

4-methoxyphenyl

183)

methyl

H

4-bromophenyl

4-methylphenyl

184)

methyl

H

phenyl

4-isopropylphe-

nyl

185)

methyl

H

phenyl

4-fluorophenyl

186)

methyl

H

phenyl

3-fluorophenyl

187)

methyl

H

phenyl

2-fluorophenyl

188)

methyl

H

phenyl

2,3,5,6-tetra-

fluorophenyl

189)

methyl

H

phenyl

4-trifluoro-

methylphenyl

190)

methyl

H

phenyl

3-trifluoro-

methylphenyl

191)

methyl

H

phenyl

4-methyl-

sulfonylphenyl

192)

methyl

H

phenyl

4-chlorophenyl

193)

methyl

H

phenyl

3-chlorophenyl

194)

methyl

H

phenyl

2-chlorophenyl

195)

methyl

H

phenyl

3,5-dichloro-

phenyl

196)

methyl

H

phenyl

4-(trifluoro-

methoxy)phenyl

197)

methyl

H

phenyl

3-(trifluoro-

methoxy)phenyl

198)

methyl

H

phenyl

4-(difluoro-

methoxy)phenyl

199)

methyl

H

phenyl

3-(difluoro-

methoxy)phenyl

200)

methyl

H

phenyl

4-cyanophenyl

201)

methyl

H

4-chlorophenyl

4-trifluoro-

methylphenyl

202)

methyl

H

4-chlorophenyl

3-trifluoro-

methylphenyl

203)

methyl

H

4-chlorophenyl

2-chlorophenyl

204)

methyl

H

4-chlorophenyl

3-chlorophenyl

205)

methyl

H

4-chlorophenyl

4-trifluoro-

methoxyphenyl

206)

methyl

H

4-chlorophenyl

3-trifluoro-

methoxyphenyl

207)

methyl

H

4-chlorophenyl

4-difluoro-

methoxyphenyl

208)

methyl

H

4-chlorophenyl

3-difluoro-

methoxyphenyl

209)

methyl

H

4-fluorophenyl

phenyl

210)

methyl

H

4-fluorophenyl

4-ethylphenyl

211)

methyl

H

4-fluorophenyl

4-methylphenyl

212)

methyl

H

4-fluorophenyl

2-methylphenyl

213)

methyl

H

4-fluorophenyl

3-methylphenyl

214)

methyl

H

4-fluorophenyl

4-fluorophenyl

215)

methyl

H

4-fluorophenyl

2,4-difluoro-

phenyl

216)

methyl

H

4-fluorophenyl

4-chlorophenyl

217)

methyl

H

4-fluorophenyl

3-chlorophenyl

218)

methyl

H

4-fluorophenyl

2-chlorophenyl

219)

methyl

H

4-fluorophenyl

4-chloro-2-

methoxyphenyl

220)

methyl

H

4-fluorophenyl

4-trifluoro-

methylphenyl

221)

methyl

H

4-fluorophenyl

2-trifluoro-

methylphenyl

222)

methyl

H

4-fluorophenyl

3-trifluoro-

methylphenyl

223)

methyl

H

4-fluorophenyl

4-(trifluoro-

methoxy)phenyl

224)

methyl

H

4-fluorophenyl

3-(trifluoro-

methoxy)phenyl

225)

methyl

H

4-fluorophenyl

4-(difluoro-

methoxy)phenyl

226)

methyl

H

4-fluorophenyl

3-(difluoro-

methoxy)phenyl

227)

methyl

H

4-fluorophenyl

4-cyanophenyl

228)

methyl

H

3-fluorophenyl

phenyl

229)

methyl

H

3-fluorophenyl

4-ethylphenyl

230)

methyl

H

3-fluorophenyl

4-methylphenyl

231)

methyl

H

3-fluorophenyl

2-methylphenyl

232)

methyl

H

3-fluorophenyl

3-methylphenyl

233)

methyl

H

3-fluorophenyl

4-fluorophenyl

234)

methyl

H

3-fluorophenyl

2,4-difluoro-

phenyl

235)

methyl

H

3-fluorophenyl

4-chlorophenyl

236)

methyl

H

3-fluorophenyl

3-chlorophenyl

237)

methyl

H

3-fluorophenyl

2-chlorophenyl

238)

methyl

H

3-fluorophenyl

4-chloro-2-

methoxyphenyl

239)

methyl

H

3-fluorophenyl

4-trifluoro-

methylphenyl

240)

methyl

H

3-fluorophenyl

2-trifluoro-

methylphenyl

241)

methyl

H

3-fluorophenyl

3-trifluoro-

methylphenyl

242)

methyl

H

3-fluorophenyl

4-(trifluoro-

methoxy)phenyl

243)

methyl

H

3-fluorophenyl

3-(trifluoro-

methoxy)phenyl

244)

methyl

H

3-fluorophenyl

4-(difluoro-

methoxy)phenyl

245)

methyl

H

3-fluorophenyl

3-(difluoro-

methoxy)phenyl

246)

methyl

H

3-fluorophenyl

4-cyanophenyl

247)

methyl

H

2-fluorophenyl

phenyl

248)

methyl

H

2-fluorophenyl

4-ethylphenyl

249)

methyl

H

2-fluorophenyl

4-methylphenyl

250)

methyl

H

2-fluorophenyl

2-methylphenyl

251)

methyl

H

2-fluorophenyl

3-methylphenyl

252)

methyl

H

2-fluorophenyl

4-fluorophenyl

253)

methyl

H

2-fluorophenyl

2,4-difluoro-

phenyl

254)

methyl

H

2-fluorophenyl

4-chlorophenyl

255)

methyl

H

2-fluorophenyl

3-chlorophenyl

256)

methyl

H

2-fluorophenyl

2-chlorophenyl

257)

methyl

H

2-fluorophenyl

4-chloro-2-

methoxyphenyl

258)

methyl

H

2-fluorophenyl

4-trifluoro-

methylphenyl

259)

methyl

H

2-fluorophenyl

2-trifluoro-

methylphenyl

260)

methyl

H

2-fluorophenyl

3-trifluoro-

methylphenyl

261)

methyl

H

2-fluorophenyl

4-(trifluoro-

methoxy)phenyl

262)

methyl

H

2-fluorophenyl

3-(trifluoro-

methoxy)phenyl

263)

methyl

H

2-fluorophenyl

4-(difluoro-

methoxy)phenyl

264)

methyl

H

2-fluorophenyl

3-(difluoro-

methoxy)phenyl

265)

methyl

H

2-fluorophenyl

4-cyanophenyl

266)

methyl

H

2,4-difluoro-

phenyl

phenyl

267)

methyl

H

2,4-difluoro-

4-ethylphenyl

phenyl

268)

methyl

H

2,4-difluoro-

4-methylphenyl

phenyl

269)

methyl

H

2,4-difluoro-

2-methylphenyl

phenyl

270)

methyl

H

2,4-difluoro-

3-methylphenyl

phenyl

271)

methyl

H

2,4-difluoro-

4-fluorophenyl

phenyl

272)

methyl

H

2,4-difluoro-

2,4-difluoro-

phenyl

phenyl

273)

methyl

H

2,4-difluoro-

4-chlorophenyl

phenyl

274)

methyl

H

2,4-difluoro-

3-chlorophenyl

phenyl

275)

methyl

H

2,4-difluoro-

2-chlorophenyl

phenyl

276)

methyl

H

2,4-difluoro-

4-chloro-2-

phenyl

methoxyphenyl

277)

methyl

H

2,4-difluoro-

4-trifluoro-

phenyl

methylphenyl

278)

methyl

H

2,4-difluoro-

2-trifluoro-

phenyl

methylphenyl

279)

methyl

H

2,4-difluoro-

3-trifluoro-

phenyl

methylphenyl

280)

methyl

H

2,4-difluoro-

4-(trifluoro-

phenyl

methoxy)phenyl

281)

methyl

H

2,4-difluoro-

3-(trifluoro-

phenyl

methoxy)phenyl

282)

methyl

H

2,4-difluoro-

4-(difluoro-

phenyl

methoxy)phenyl

283)

methyl

H

2,4-difluoro-

3-(difluoro-

phenyl

methoxy)phenyl

284)

methyl

H

2,4-difluoro-

4-cyanophenyl

phenyl

285)

methyl

H

4-trifluoro-

phenyl

methylphenyl

286)

methyl

H

4-trifluoro-

4-ethylphenyl

methylphenyl

287)

methyl

H

4-trifluoro-

4-methylphenyl

methylphenyl

288)

methyl

H

4-trifluoro-

2-methylphenyl

methylphenyl

289)

methyl

H

4-trifluoro-

3-methylphenyl

methylphenyl

290)

methyl

H

4-trifluoro-

4-fluorophenyl

methylphenyl

291)

methyl

H

4-trifluoro-

2,4-difluoro-

methylphenyl

phenyl

292)

methyl

H

4-trifluoro-

4-chlorophenyl

methylphenyl

293)

methyl

H

4-trifluoro-

3-chlorophenyl

methylphenyl

294)

methyl

H

4-trifluoro-

2-chlorophenyl

methylphenyl

295)

methyl

H

4-trifluoro-

4-chloro-2-

methylphenyl

methoxyphenyl

296)

methyl

H

4-trifluoro-

4-trifluoro-

methylphenyl

methylphenyl

297)

methyl

H

4-trifluoro-

2-trifluoro-

methylphenyl

methylphenyl

298)

methyl

H

4-trifluoro-

3-trifluoro-

methylphenyl

methylphenyl

299)

methyl

H

4-trifluoro-

4-(trifluoro-

methylphenyl

methoxy)phenyl

300)

methyl

H

4-trifluoro-

3-(trifluoro-

methylphenyl

methoxy)phenyl

301)

methyl

H

4-trifluoro-

4-(difluoro-

methylphenyl

methoxy)phenyl

302)

methyl

H

4-trifluoro-

3-(difluoro-

methylphenyl

methoxy)phenyl

303)

methyl

H

4-trifluoro-

4-cyanophenyl

methylphenyl

304)

methyl

H

3,4-dichloro-

4-fluorophenyl

phenyl

305)

methyl

H

3,4-

phenyl

(methylene-

dioxy)phenyl

306)

methyl

H

3-trifluoro-

phenyl

methylphenyl

307)

methyl

H

3-trifluoro-

4-ethylphenyl

methylphenyl

308)

methyl

H

3-trifluoro-

4-methylphenyl

methylphenyl

309)

methyl

H

3-trifluoro-

2-methylphenyl

methylphenyl

310)

methyl

H

3-trifluoro-

3-methylphenyl

methylphenyl

311)

methyl

H

3-trifluoro-

4-fluorophenyl

methylphenyl

312)

methyl

H

3-trifluoro-

2,4-difluoro-

methylphenyl

phenyl

313)

methyl

H

3-trifluoro-

4-chlorophenyl

methylphenyl

314)

methyl

H

3-trifluoro-

3-chlorophenyl

methylphenyl

315)

methyl

H

3-trifluoro-

2-chlorophenyl

methylphenyl

316)

methyl

H

3-trifluoro-

4-chloro-2-

methylphenyl

methoxyphenyl

317)

methyl

H

3-trifluoro-

4-trifluoro-

methylphenyl

methylphenyl

318)

methyl

H

3-trifluoro-

2-trifluoro-

methylphenyl

methylphenyl

319)

methyl

H

3-trifluoro-

3-trifluoro-

methylphenyl

methylphenyl

320)

methyl

H

3-trifluoro-

4-(trifluoro-

methylphenyl

methoxy)phenyl

321)

methyl

H

3-trifluoro-

3-(trifluoro-

methylphenyl

methoxy)phenyl

322)

methyl

H

3-trifluoro-

4-(difluoro-

methylphenyl

methoxy)phenyl

323)

methyl

H

3-trifluoro-

3-(difluoro-

methylphenyl

methoxy)phenyl

324)

methyl

H

3-trifluoro-

4-cyanophenyl

methylphenyl

325)

formyl

H

phenyl

phenyl

326)

formyl

H

phenyl

4-methylphenyl

327)

formyl

H

phenyl

2,4-dichloro-

phenyl

328)

formyl

H

4-methylphenyl

4-chlorophenyl

329)

formyl

H

4-methoxy-

4-methoxyphenyl

phenyl

330)

formyl

H

4-methoxy-

2-methoxyphenyl

phenyl

331)

formyl

H

4-methoxy-

4-chlorophenyl

phenyl

332)

formyl

H

4-methoxy-

2,4-dichloro-

phenyl

phenyl

333)

formyl

H

3-chlorophenyl

phenyl

334)

formyl

H

3,4-dichloro-

phenyl

phenyl

335)

formyl

H

4-chlorophenyl

4-chlorophenyl

336)

formyl

H

4-chlorophenyl

3,4-dichloro-

phenyl

337)

formyl

H

4-chlorophenyl

2,4-dichloro-

phenyl

338)

formyl

H

4-chlorophenyl

4-fluorophenyl

339)

formyl

H

4-chlorophenyl

4-formylphenyl

340)

formyl

H

4-bromophenyl

4-methoxyphenyl

341)

formyl

H

4-bromophenyl

4-formylphenyl

342)

formyl

H

phenyl

4-isopropyl-

phenyl

343)

formyl

H

phenyl

4-fluorophenyl

344)

formyl

H

phenyl

3-fluorophenyl

345)

formyl

H

phenyl

2-fluorophenyl

346)

formyl

H

phenyl

2,3,5,6-tetra-

fluorophenyl

347)

formyl

H

phenyl

4-trifluoro-

methylphenyl

348)

formyl

H

phenyl

3-trifluoro-

methylphenyl

349)

formyl

H

phenyl

4-formyl-

sulfonylphenyl

350)

formyl

H

phenyl

4-chlorophenyl

351)

formyl

H

phenyl

3-chlorophenyl

352)

formyl

H

phenyl

2-chlorophenyl

353)

formyl

H

phenyl

3,5-dichloro-

phenyl

354)

formyl

H

phenyl

4-(trifluoro-

methoxy)phenyl

355)

formyl

H

phenyl

3-(trifluoro-

methoxy)phenyl

356)

formyl

H

phenyl

4-(difluoro-

methoxy)phenyl

357)

formyl

H

phenyl

3-(difluoro-

methoxy)phenyl

358)

formyl

H

phenyl

4-cyanophenyl

359)

formyl

H

4-chlorophenyl

4-trifluoro-

methylphenyl

360)

formyl

H

4-chlorophenyl

3-trifluoro-

methylphenyl

361)

formyl

H

4-chlorophenyl

2-chlorophenyl

362)

formyl

H

4-chlorophenyl

3-chlorophenyl

363)

formyl

H

4-chlorophenyl

4-trifluoro-

methoxyphenyl

364)

formyl

H

4-chlorophenyl

3-trifluoro-

methoxyphenyl

365)

formyl

H

4-chlorophenyl

4-difluoro-

methoxyphenyl

366)

formyl

H

4-chlorophenyl

3-difluoro-

methoxyphenyl

367)

formyl

H

4-fluorophenyl

phenyl

368)

formyl

H

4-fluorophenyl

4-ethylphenyl

369)

formyl

H

4-fluorophenyl

4-formylphenyl

370)

formyl

H

4-fluorophenyl

2-formylphenyl

371)

formyl

H

4-fluorophenyl

3-formylphenyl

372)

formyl

H

4-fluorophenyl

4-fluorophenyl

373)

formyl

H

4-fluorophenyl

2,4-difluoro-

phenyl

374)

formyl

H

4-fluorophenyl

4-chlorophenyl

375)

formyl

H

4-fluorophenyl

3-chlorophenyl

376)

formyl

H

4-fluorophenyl

2-chlorophenyl

377)

formyl

H

4-fluorophenyl

4-chloro-2-

methoxyphenyl

378)

formyl

H

4-fluorophenyl

4-trifluoro-

methylphenyl

379)

formyl

H

4-fluorophenyl

2-trifluoro-

methylphenyl

380)

formyl

H

4-fluorophenyl

3-trifluoro-

methylphenyl

381)

formyl

H

4-fluorophenyl

4-(trifluoro-

methoxy)phenyl

382)

formyl

H

4-fluorophenyl

3-(trifluoro-

methoxy)phenyl

383)

formyl

H

4-fluorophenyl

4-(difluoro-

methoxy)phenyl

384)

formyl

H

4-fluorophenyl

3-(difluoro-

methoxy)phenyl

385)

formyl

H

4-fluorophenyl

4-cyanophenyl

386)

formyl

H

3-fluorophenyl

phenyl

387)

formyl

H

3-fluorophenyl

4-ethylphenyl

388)

formyl

H

3-fluorophenyl

4-formylphenyl

389)

formyl

H

3-fluorophenyl

2-formylphenyl

390)

formyl

H

3-fluorophenyl

3-formylphenyl

391)

formyl

H

3-fluorophenyl

4-fluorophenyl

392)

formyl

H

3-fluorophenyl

2,4-difluoro-

phenyl

393)

formyl

H

3-fluorophenyl

4-chlorophenyl

394)

formyl

H

3-fluorophenyl

3-chlorophenyl

395)

formyl

H

3-fluorophenyl

2-chlorophenyl

396)

formyl

H

3-fluorophenyl

4-chloro-2-

methoxyphenyl

397)

formyl

H

3-fluorophenyl

4-trifluoro-

methylphenyl

398)

formyl

H

3-fluorophenyl

2-trifluoro-

methylphenyl

399)

formyl

H

3-fluorophenyl

3-trifluoro-

methylphenyl

400)

formyl

H

3-fluorophenyl

4-(trifluoro-

methoxy)phenyl

401)

formyl

H

3-fluorophenyl

3-(trifluoro-

methoxy)phenyl

402)

formyl

H

3-fluorophenyl

4-(difluoro-

methoxy)phenyl

403)

formyl

H

3-fluorophenyl

3-(difluoro-

methoxy)phenyl

404)

formyl

H

3-fluorophenyl

4-cyanophenyl

405)

formyl

H

2-fluorophenyl

phenyl

406)

formyl

H

2-fluorophenyl

4-ethylphenyl

407)

formyl

H

2-fluorophenyl

4-formylphenyl

408)

formyl

H

2-fluorophenyl

2-formylphenyl

409)

formyl

H

2-fluorophenyl

3-formylphenyl

410)

formyl

H

2-fluorophenyl

4-fluorophenyl

411)

formyl

H

2-fluorophenyl

2,4-difluoro-

phenyl

412)

formyl

H

2-fluorophenyl

4-chlorophenyl

413)

formyl

H

2-fluorophenyl

3-chlorophenyl

414)

formyl

H

2-fluorophenyl

2-chlorophenyl

415)

formyl

H

2-fluorophenyl

4-chloro-2-

methoxyphenyl

416)

formyl

H

2-fluorophenyl

4-trifluoro-

methylphenyl

417)

formyl

H

2-fluorophenyl

2-trifluoro-

methylphenyl

418)

formyl

H

2-fluorophenyl

3-trifluoro-

methylphenyl

419)

formyl

H

2-fluorophenyl

4-(trifluoro-

methoxy)phenyl

420)

formyl

H

2-fluorophenyl

3-(trifluoro-

methoxy)phenyl

421)

formyl

H

2-fluorophenyl

4-(difluoro-

methoxy)phenyl

422)

formyl

H

2-fluorophenyl

3-(difluoro-

methoxy)phenyl

423)

formyl

H

2-fluorophenyl

4-cyanophenyl

424)

formyl

H

2,4-difluoro-

phenyl

phenyl

425)

formyl

H

2,4-difluoro-

4-ethylphenyl

phenyl

426)

formyl

H

2,4-difluoro-

4-formylphenyl

phenyl

427)

formyl

H

2,4-difluoro-

2-formylphenyl

phenyl

428)

formyl

H

2,4-difluoro-

3-formylphenyl

phenyl

429)

formyl

H

2,4-difluoro-

4-fluorophenyl

phenyl

430)

formyl

H

2,4-difluoro-

2,4-difluoro-

phenyl

phenyl

431)

formyl

H

2,4-difluoro-

4-chlorophenyl

phenyl

432)

formyl

H

2,4-difluoro-

3-chlorophenyl

phenyl

433)

formyl

H

2,4-difluoro-

2-chlorophenyl

phenyl

434)

formyl

H

2,4-difluoro-

4-chloro-2-

phenyl

methoxyphenyl

435)

formyl

H

2,4-difluoro-

4-trifluoro-

phenyl

methylphenyl

436)

formyl

H

2,4-difluoro-

2-trifluoro-

phenyl

methylphenyl

437)

formyl

H

2-4-difluoro-

3-trifluoro-

phenyl

methylphenyl

438)

formyl

H

2,4-difluoro-

4-(trifluoro-

phenyl

methoxy)phenyl

439)

formyl

H

2,4-difluoro-

3-(trifluoro-

phenyl

methoxy)phenyl

440)

formyl

H

2,4-difluoro-

4-(difluoro-

phenyl

methoxy)phenyl

441)

formyl

H

2,4-difluoro-

3-(difluoro-

phenyl

methoxy)phenyl

442)

formyl

H

2,4-difluoro-

4-cyanophenyl

phenyl

443)

formyl

H

4-trifluoro-

phenyl

methylphenyl

444)

formyl

H

4-trifluoro-

4-ethylphenyl

methylphenyl

445)

formyl

H

4-trifluoro-

4-formylphenyl

methylphenyl

446)

formyl

H

4-trifluoro-

2-formylphenyl

methylphenyl

447)

formyl

H

4-trifluoro-

3-formylphenyl

methylphenyl

448)

formyl

H

4-trifluoro-

4-fluorophenyl

methylphenyl

449)

formyl

H

4-trifluoro-

2,4-difluoro-

methylphenyl

phenyl

450)

formyl

H

4-trifluoro-

4-chlorophenyl

methylphenyl

451)

formyl

H

4-trifluoro-

3-chlorophenyl

methylphenyl

452)

formyl

H

4-trifluoro-

2-chlorophenyl

methylphenyl

453)

formyl

H

4-trifluoro-

4-chloro-2-

methylphenyl

methoxyphenyl

454)

formyl

H

4-trifluoro-

4-trifluoro-

methylphenyl

methylphenyl

455)

formyl

H

4-trifluoro-

2-trifluoro-

methylphenyl

methylphenyl

456)

formyl

H

4-trifluoro-

3-trifluoro-

methylphenyl

methylphenyl

457)

formyl

H

4-trifluoro-

4-(trifluoro-

methylphenyl

methoxy)phenyl

458)

formyl

H

4-trifluoro-

3-(trifluoro-

methylphenyl

methoxy)phenyl

459)

formyl

H

4-trifluoro-

4-(difluoro-

methylphenyl

methoxy)phenyl

460)

formyl

H

4-trifluoro-

3-(difluoro-

methylphenyl

methoxy)phenyl

461)

formyl

H

4-trifluoro-

4-cyanophenyl

methylphenyl

462)

formyl

H

3,4-dichloro-

4-fluorophenyl

phenyl

463)

formyl

H

3,4-(formyl-

phenyl

enedi-

oxy)phenyl

464)

formyl

H

3-trifluoro-

phenyl

methylphenyl

465)

formyl

H

3-trifluoro-

4-ethylphenyl

methylphenyl

466)

formyl

H

3-trifluoro-

4-formylphenyl

methylphenyl

467)

formyl

H

3-trifluoro-

2-formylphenyl

methylphenyl

468)

formyl

H

3-trifluoro-

3-formylphenyl

methylphenyl

469)

formyl

H

3-trifluoro-

4-fluorophenyl

methylphenyl

470)

formyl

H

3-trifluoro-

2,4-difluoro-

methylphenyl

phenyl

471)

formyl

H

3-trifluoro-

4-chlorophenyl

methylphenyl

472)

formyl

H

3-trifluoro-

3-chlorophenyl

methylphenyl

473)

formyl

H

3-trifluoro-

2-chlorophenyl

methylphenyl

474)

formyl

H

3-trifluoro-

4-chloro-2-

methylphenyl

methoxyphenyl

475)

formyl

H

3-trifluoro-

4-trifluoro-

methylphenyl

methylphenyl

476)

formyl

H

3-trifluoro-

2-trifluoro-

methylphenyl

methylphenyl

477)

formyl

H

3-trifluoro-

3-trifluoro-

methylphenyl

methylphenyl

478)

formyl

H

3-trifluoro-

4-(trifluoro-

methylphenyl

methoxy)phenyl

479)

formyl

H

3-trifluoro-

3-(trifluoro-

methylphenyl

methoxy)phenyl

480)

formyl

H

3-trifluoro-

4-(difluoro-

methylphenyl

methoxy)phenyl

481)

formyl

H

3-trifluoro-

3-(difluoro-

methylphenyl

methoxy)phenyl

482)

formyl

H

3-trifluoro-

4-cyanophenyl

methylphenyl

483)

formyl

H

4-formylphenyl

phenyl

484)

formyl

H

4-methoxy-

phenyl

phenyl

485)

formyl

H

4-chlorophenyl

phenyl

m.p.

145-

146° C.

486)

H

methyl

phenyl

phenyl

487)

H

methyl

phenyl

4-methylphenyl

488)

H

methyl

phenyl

2,4-dichloro-

phenyl

489)

H

methyl

4-methylphenyl

phenyl

490)

H

methyl

4-methylphenyl

4-chlorophenyl

491)

H

methyl

4-methoxy-

phenyl

phenyl

492)

H

methyl

4-methoxy-

4-methoxyphenyl

phenyl

493)

H

methyl

4-methoxy-

2-methoxyphenyl

phenyl

494)

H

methyl

4-methoxy-

4-chlorophenyl

phenyl

495)

H

methyl

4-methoxy-

2,4-dichloro-

phenyl

phenyl

496)

H

methyl

3-chlorophenyl

phenyl

497)

H

methyl

3,4-dichloro-

phenyl

phenyl

498)

H

methyl

4-chlorophenyl

phenyl

499)

H

methyl

4-chlorophenyl

4-chlorophenyl

500)

H

methyl

4-chlorophenyl

3,4-dichloro-

phenyl

501)

H

methyl

4-chlorophenyl

2,4-dichloro-

phenyl

502)

H

methyl

4-chlorophenyl

4-fluorophenyl

503)

H

methyl

4-chlorophenyl

4-methylphenyl

504)

H

methyl

4-bromophenyl

4-methoxyphenyl

505)

H

methyl

4-bromophenyl

4-methylphenyl

506)

methyl

methyl

4-methylphenyl

phenyl

507)

methyl

methyl

4-methoxy-

phenyl

phenyl

508)

methyl

methyl

4-chlorophenyl

phenyl

509)

H

methyl

phenyl

4-isopropyl-

phenyl

510)

H

methyl

phenyl

4-fluorophenyl

511)

H

methyl

phenyl

3-fluorophenyl

512)

H

methyl

phenyl

2-fluorophenyl

513)

H

methyl

phenyl

2,3,5,6-tetra-

fluorophenyl

514)

H

methyl

phenyl

4-trifluoro-

methylphenyl

515)

H

methyl

phenyl

3-trifluoro-

methylphenyl

516)

H

methyl

phenyl

4-methyl-

sulfonylphenyl

517)

H

Methyl

phenyl

4-chlorophenyl

518)

H

methyl

phenyl

3-chlorophenyl

519)

H

methyl

phenyl

2-chlorophenyl

520)

H

methyl

phenyl

3,5-dichloro-

phenyl

521)

H

methyl

phenyl

4-(trifluoro-

methoxy)phenyl

522)

H

methyl

phenyl

3-(trifluoro-

methoxy)phenyl

523)

H

methyl

phenyl

4-(difluoro-

methoxy)phenyl

524)

H

methyl

phenyl

3-(difluoro-

methoxy)phenyl

525)

H

methyl

phenyl

4-cyanophenyl

526)

H

methyl

4-chlorophenyl

4-trifluoro-

methylphenyl

527)

H

methyl

4-chlorophenyl

3-trifluoro-

methylphenyl

528)

H

methyl

4-chlorophenyl

2-chlorophenyl

529)

H

methyl

4-chlorophenyl

3-chlorophenyl

530)

H

methyl

4-chlorophenyl

4-trifluoro-

methoxyphenyl

531)

H

methyl

4-chlorophenyl

3-trifluoro-

methoxyphenyl

532)

H

methyl

4-chlorophenyl

4-difluoro-

methoxyphenyl

533)

H

methyl

4-chlorophenyl

3-difluoro-

methoxyphenyl

534)

H

methyl

4-fluorophenyl

phenyl

535)

H

methyl

4-fluorophenyl

4-ethylphenyl

536)

H

methyl

4-fluorophenyl

4-methylphenyl

537)

H

methyl

4-fluorophenyl

2-methylphenyl

538)

H

methyl

4-fluorophenyl

3-methylphenyl

539)

H

methyl

4-fluorophenyl

4-fluorophenyl

540)

H

methyl

4-fluorophenyl

2,4-difluoro-

phenyl

541)

H

methyl

4-fluorophenyl

4-chlorophenyl

542)

H

methyl

4-fluorophenyl

3-chlorophenyl

543)

H

methyl

4-fluorophenyl

2-chlorophenyl

544)

H

methyl

4-fluorophenyl

4-chloro-2-

methoxyphenyl

545)

H

methyl

4-fluorophenyl

4-trifluoro-

methylphenyl

546)

H

methyl

4-fluorophenyl

2-trifluoro-

methylphenyl

547)

H

methyl

4-fluorophenyl

3-trifluoro-

methylphenyl

548)

H

methyl

4-fluorophenyl

4-(trifluoro-

methoxy)phenyl

549)

H

methyl

4-fluorophenyl

3-(trifluoro-

methoxy)phenyl

550)

H

methyl

4-fluorophenyl

4-(difluoro-

methoxy)phenyl

551)

H

methyl

4-fluorophenyl

3-(difluoro-

methoxy)phenyl

552)

H

methyl

4-fluorophenyl

4-cyanophenyl

553)

H

methyl

3-fluorophenyl

phenyl

554)

H

methyl

3-fluorophenyl

4-ethylphenyl

555)

H

methyl

3-fluorophenyl

4-methylphenyl

556)

H

methyl

3-fluorophenyl

2-methylphenyl

557)

H

methyl

3-fluorophenyl

3-methylphenyl

558)

H

methyl

3-fluorophenyl

4-fluorophenyl

559)

H

methyl

3-fluorophenyl

2,4-difluoro-

phenyl

560)

H

methyl

3-fluorophenyl

4-chlorophenyl

561)

H

methyl

3-fluorophenyl

3-chlorophenyl

562)

H

methyl

3-fluorophenyl

2-chlorophenyl

563)

H

methyl

3-fluorophenyl

4-chloro-2-

methoxyphenyl

564)

H

methyl

3-fluorophenyl

4-trifluoro-

methylphenyl

565)

H

methyl

3-fluorophenyl

2-trifluoro-

methylphenyl

566)

H

methyl

3-fluorophenyl

3-trifluoro-

methylphenyl

567)

H

methyl

3-fluorophenyl

4-(trifluoro-

methoxy)phenyl

568)

H

methyl

3-fluorophenyl

3-(trifluoro-

methoxy)phenyl

569)

H

methyl

3-fluorophenyl

4-(difluoro-

methoxy)phenyl

570)

H

methyl

3-fluorophenyl

3-(difluoro-

methoxy)phenyl

571)

H

methyl

3-fluorophenyl

4-cyanophenyl

572)

H

methyl

2-fluorophenyl

phenyl

573)

H

methyl

2-fluorophenyl

4-ethylphenyl

574)

H

methyl

2-fluorophenyl

4-methylphenyl

575)

H

methyl

2-fluorophenyl

2-methylphenyl

576)

H

methyl

2-fluorophenyl

3-methylphenyl

577)

H

methyl

2-fluorophenyl

4-fluorophenyl

578)

H

methyl

2-fluorophenyl

2,4-difluoro-

phenyl

579)

H

methyl

2-fluorophenyl

4-chlorophenyl

580)

H

methyl

2-fluorophenyl

3-chlorophenyl

581)

H

methyl

2-fluorophenyl

2-chlorophenyl

582)

H

methyl

2-fluorophenyl

4-chloro-2-

methoxyphenyl

583)

H

methyl

2-fluorophenyl

4-trifluoro-

methylphenyl

584)

H

methyl

2-fluorophenyl

2-trifluoro-

methylphenyl

585)

H

methyl

2-fluorophenyl

3-trifluoro-

methylphenyl

586)

H

methyl

2-fluorophenyl

4-(trifluoro-

methoxy)phenyl

587)

H

methyl

2-fluorophenyl

3-(trifluoro-

methoxy)phenyl

588)

H

methyl

2-fluorophenyl

4-(difluoro-

methoxy)phenyl

589)

H

methyl

2-fluorophenyl

3-(difluoro-

methoxy)phenyl

590)

H

methyl

2-fluorophenyl

4-cyanophenyl

591)

H

methyl

2,4-difluoro-

phenyl

phenyl

592)

H

methyl

2,4-difluoro-

4-ethylphenyl

phenyl

593)

H

methyl

2,4-difluoro-

4-methylphenyl

phenyl

594)

H

methyl

2,4-difluoro-

2-methylphenyl

phenyl

595)

H

methyl

2,4-difluoro-

3-methylphenyl

phenyl

596)

H

methyl

2,4-difluoro-

4-fluorophenyl

phenyl

597)

H

methyl

2,4-difluoro-

2,4-difluoro-

phenyl

phenyl

598)

H

methyl

2,4-difluoro-

4-chlorophenyl

phenyl

599)

H

methyl

2,4-difluoro-

3-chlorophenyl

phenyl

600)

H

methyl

2,4-difluor-

2-chlorophenyl

phenyl

601)

H

methyl

2,4-difluoro-

4-chloro-2-

phenyl

methoxyphenyl

602)

H

methyl

2,4-difluoro-

4-trifluoro-

phenyl

methylphenyl

603)

H

methyl

2,4-difluoro-

2-trifluoro-

phenyl

methylphenyl

604)

H

methyl

2,4-difluoro-

3-trifluoro-

phenyl

methylphenyl

605)

H

methyl

2,4-difluoro-

4-(trifluoro-

phenyl

methoxy)phenyl

606)

H

methyl

2,4-difluoro-

3-(trifluoro-

phenyl

methoxy)phenyl

607)

H

methyl

2,4-difluoro-

4-(difluoro-

phenyl

methoxy)phenyl

608)

H

methyl

2,4-difluoro-

3-(difluoro-

phenyl

methoxy)phenyl

609)

H

methyl

2,4-difluoro-

4-cyanophenyl

phenyl

610)

H

methyl

4-trifluoro-

phenyl

methylphenyl

611)

H

methyl

4-trifluoro-

4-ethylphenyl

methylphenyl

612)

H

methyl

4-trifluoro-

4-methylphenyl

methylphenyl

613)

H

methyl

4-trifluoro-

2-methylphenyl

methylphenyl

614)

H

methyl

4-trifluoro-

3-methylphenyl

methylphenyl

615)

H

methyl

4-trifluoro-

4-fluorophenyl

methylphenyl

616)

H

methyl

4-trifluoro-

2,4-difluoro-

methylphenyl

phenyl

617)

H

methyl

4-trifluoro-

4-chlorophenyl

methylphenyl

618)

H

methyl

4-trifluoro-

3-chlorophenyl

methylphenyl

619)

H

methyl

4-trifluoro-

2-chlorophenyl

methylphenyl

620)

H

methyl

4-trifluoro-

4-chloro-2-

methylphenyl

methoxyphenyl

621)

H

methyl

4-trifluoro-

4-trifluoro-

methylphenyl

methylphenyl

622)

H

methyl

4-trifluoro-

2-trifluoro-

methylphenyl

methylphenyl

623)

H

methyl

4-trifluoro-

3-trifluoro-

methylphenyl

methylphenyl

624)

H

methyl

4-trifluoro-

4-(trifluoro-

methylphenyl

methoxy)phenyl

625)

H

methyl

4-trifluoro-

3-(trifluoro-

methylphenyl

methoxy)phenyl

626)

H

methyl

4-trifluoro-

4-(difluoro-

methylphenyl

methoxy)phenyl

627)

H

methyl

4-trifluoro-

3-(difluoro-

methylphenyl

methoxy)phenyl

628)

H

methyl

4-trifluoro-

4-cyanophenyl

methylphenyl

629)

H

methyl

3,4-dichloro-

4-fluorophenyl

phenyl

630)

H

methyl

3,4-(methyle-

phenyl

nedioxy)phenyl

631)

H

methyl

3-trifluoro-

phenyl

methylphenyl

632)

H

methyl

3-trifluoro-

4-ethylphenyl

methylphenyl

633)

H

methyl

3-trifluoro-

4-methylphenyl

methylphenyl

634)

H

methyl

3-trifluoro-

2-methylphenyl

methylphenyl

635)

H

methyl

3-trifluoro-

3-methylphenyl

methylphenyl

636)

H

methyl

3-trifluoro-

4-fluorophenyl

methylphenyl

637)

H

methyl

3-trifluoro-

2,4-difluoro-

methylphenyl

phenyl

638)

H

methyl

3-trifluoro-

4-chlorophenyl

methylphenyl

639)

H

methyl

3-trifluoro-

3-chlorophenyl

640)

H

methyl

3-trifluoro-

2-chlorophenyl

methylphenyl

641)

H

methyl

3-trifluoro-

4-chloro-2-

methylphenyl

methylphenyl

642)

H

methyl

3-trifluoro-

4-trifluoro-

methylphenyl

methylphenyl

643)

H

methyl

3-trifluoro-

2-trifluoro-

methylphenyl

methylphenyl

644)

H

methyl

3-trifluoro-

3-trifluoro-

methylphenyl

methylphenyl

645)

H

methyl

3-trifluoro-

4-(trifluoro-

methylphenyl

methoxy)phenyl

646)

H

methyl

3-trifluoro-

3-(trifluoro-

methylphenyl

methoxy)phenyl

647)

H

methyl

3-trifluoro-

4-(difluoro-

methylphenyl

methoxy)phenyl

648)

H

methyl

3-trifluoro-

3-(difluoro-

methylphenyl

methoxy)phenyl

649)

H

methyl

3-trifluoro-

4-cyanophenyl

methylphenyl

650)

methyl

methyl

phenyl

phenyl

651)

methyl

methyl

phenyl

4-methylphenyl

652)

methyl

methyl

phenyl

2,4-dichloro-

phenyl

653)

methyl

methyl

4-methylphenyl

4-chlorophenyl

654)

methyl

methyl

4-methoxy-

4-methoxyphenyl

phenyl

655)

methyl

methyl

4-methoxy-

2-methoxyphenyl

phenyl

656)

methyl

methyl

4-methoxy-

4-chlorophenyl

phenyl

657)

methyl

methyl

4-methoxy-

2,4-dichloro-

phenyl

phenyl

658)

methyl

methyl

3-chlorophenyl

phenyl

659)

methyl

methyl

3,4-dichloro-

phenyl

phenyl

660)

methyl

methyl

4-chlorophenyl

4-chlorophenyl

661)

methyl

methyl

4-chlorophenyl

3,4-dichloro-

phenyl

662)

Methyl

methyl

4-chlorophenyl

2,4-dichloro-

phenyl

663)

methyl

methyl

4-chlorophenyl

4-fluorophenyl

664)

methyl

methyl

4-chlorophenyl

4-methylphenyl

665)

methyl

methyl

4-bromophenyl

4-methoxyphenyl

666)

methyl

methyl

4-bromophenyl

4-methylphenyl

667)

methyl

methyl

phenyl

4-isopropylphe-

nyl

668)

methyl

methyl

phenyl

4-fluorophenyl

669)

methyl

methyl

phenyl

3-fluorophenyl

670)

methyl

methyl

phenyl

2-fluorophenyl

671)

methyl

methyl

phenyl

2,3,5,6-tetra-

fluorophenyl

672)

methyl

methyl

phenyl

4-trifluoro-

methylphenyl

673)

methyl

methyl

phenyl

3-trifluoro-

methylphenyl

674)

methyl

methyl

phenyl

4-methyl-

sulphonylphenyl

675)

methyl

methyl

phenyl

4-chlorophenyl

676)

methyl

methyl

phenyl

3-chlorophenyl

677)

methyl

methyl

phenyl

2-chlorophenyl

678)

methyl

methyl

phenyl

3,5-dichloro-

phenyl

679)

methyl

methyl

phenyl

4-(trifluoro-

methoxy)phenyl

680)

methyl

methyl

phenyl

3-(trifluoro-

methoxy)phenyl

681)

methyl

methyl

phenyl

4-(difluoro-

methoxy)phenyl

682)

methyl

methyl

phenyl

3-(difluoro-

methoxy)phenyl

683)

methyl

methyl

phenyl

4-cyanophenyl

684)

methyl

methyl

4-chlorophenyl

4-trifluoro-

methylphenyl

685)

methyl

methyl

4-chlorophenyl

3-trifluoro-

methylphenyl

686)

methyl

methyl

4-chlorophenyl

2-chlorophenyl

687)

methyl

methyl

4-chlorophenyl

3-chlorophenyl

688)

methyl

methyl

4-chlorophenyl

4-trifluoro-

methoxyphenyl

689)

methyl

methyl

4-chlorophenyl

3-trifluoro-

methoxyphenyl

690)

methyl

methyl

4-chlorophenyl

4-difluoro-

methoxyphenyl

691)

methyl

methyl

4-chlorophenyl

3-difluoro-

methoxyphenyl

692)

methyl

methyl

4-fluorophenyl

phenyl

693)

methyl

methyl

4-fluorophenyl

4-ethylphenyl

694)

methyl

methyl

4-fluorophenyl

4-methylphenyl

695)

methyl

methyl

4-fluorophenyl

2-methylphenyl

696)

methyl

methyl

4-fluorophenyl

3-methylphenyl

697)

methyl

methyl

4-fluorophenyl

4-fluorophenyl

698)

methyl

methyl

4-fluorophenyl

2,4-difluoro-

phenyl

699)

methyl

methyl

4-fluorophenyl

4-chlorophenyl

700)

methyl

methyl

4-fluorophenyl

3-chlorophenyl

701)

methyl

methyl

4-fluorophenyl

2-chlorophenyl

702)

methyl

methyl

4-fluorophenyl

4-chloro-2

methoxyphenyl

703)

methyl

methyl

4-fluorophenyl

4-trifluoro-

methylphenyl

704)

methyl

methyl

4-fluorophenyl

2-trifluoro-

methylphenyl

705)

methyl

methyl

4-fluorophenyl

3-trifluoro-

methylphenyl

706)

methyl

methyl

4-fluorophenyl

4-(trifluoro-

methoxy)phenyl

707)

methyl

methyl

4-fluorophenyl

3-(trifluoro-

methoxy)phenyl

708)

methyl

methyl

4-fluorophenyl

4-(difluoro-

methoxy)phenyl

709)

methyl

methyl

4-fluorophenyl

3-(difluoro-

methoxy)phenyl

710)

methyl

methyl

4-fluorophenyl

4-cyanophenyl

711)

methyl

methyl

3-fluorophenyl

phenyl

712)

methyl

methyl

3-fluorophenyl

4-ethylphenyl

713)

methyl

methyl

3-fluorophenyl

4-methylphenyl

714)

methyl

methyl

3-fluorophenyl

2-methylphenyl

715)

methyl

methyl

3-fluorophenyl

3-methylphenyl

716)

methyl

methyl

3-fluorophenyl

4-fluorophenyl

717)

methyl

methyl

3-fluorophenyl

2,4-difluoro-

phenyl

718)

methyl

methyl

3-fluorophenyl

4-chlorophenyl

719)

methyl

methyl

3-fluorophenyl

3-chlorophenyl

720)

methyl

methyl

3-fluorophenyl

2-chlorophenyl

721)

methyl

methyl

3-fluorophenyl

4-chloro-2-

methoxyphenyl

722)

methyl

methyl

3-fluorophenyl

4-trifluoro-

methylphenyl

723)

methyl

methyl

3-fluorophenyl

2-trifluoro-

methylphenyl

724)

methyl

methyl

3-fluorophenyl

3-trifluoro-

methylphenyl

725)

methyl

methyl

3-fluorophenyl

4-(trifluoro-

methoxy)phenyl

726)

methyl

methyl

3-fluorophenyl

3-(trifluoro-

methoxy)phenyl

727)

methyl

methyl

3-fluorophenyl

4-(difluoro-

methoxy)phenyl

728)

methyl

methyl

3-fluorophenyl

3-(difluoro-

methoxy)phenyl

729)

methyl

methyl

3-fluorophenyl

4-cyanophenyl

730)

methyl

methyl

2-fluorophenyl

phenyl

731)

methyl

methyl

2-fluorophenyl

4-ethylphenyl

732)

methyl

methyl

2-fluorophenyl

4-methylphenyl

733)

methyl

methyl

2-fluorophenyl

2-methylphenyl

734)

methyl

methyl

2-fluorophenyl

3-methylphenyl

735)

methyl

methyl

2-fluorophenyl

4-fluorophenyl

736)

methyl

methyl

2-fluorophenyl

2,4-difluoro-

phenyl

737)

methyl

methyl

2-fluorophenyl

4-chlorophenyl

738)

methyl

methyl

2-fluorophenyl

3-chlorophenyl

739)

methyl

methyl

2-fluorophenyl

2-chlorophenyl

740)

methyl

methyl

2-fluorophenyl

4-chloro-2-

methoxyphenyl

741)

methyl

methyl

2-fluorophenyl

4-trifluoro-

methylphenyl

742)

methyl

methyl

2-fluorophenyl

2-trifluoro-

methylphenyl

743)

methyl

methyl

2-fluorophenyl

3-trifluoro-

methylphenyl

744)

methyl

methyl

2-fluorophenyl

4-(trifluoro-

methoxy)phenyl

745)

methyl

methyl

2-fluorophenyl

3-(trifluoro-

methoxy)phenyl

746)

methyl

methyl

2-fluorophenyl

4-(difluoro-

methoxy)phenyl

747)

methyl

methyl

2-fluorophenyl

3-(difluoro-

methoxy)phenyl

748)

methyl

methyl

2-fluorophenyl

4-cyanophenyl

749)

methyl

methyl

2,4-difluoro-

phenyl

phenyl

750)

methyl

methyl

2,4-difluoro-

4-ethylphenyl

phenyl

751)

methyl

methyl

2,4-difluoro-

4-methylphenyl

phenyl

752)

methyl

methyl

2,4-difluoro-

2-methylphenyl

phenyl

753)

methyl

methyl

2,4-difluoro-

3-methylphenyl

phenyl

754)

methyl

methyl

2,4-difluoro-

4-fluorophenyl

phenyl

755)

methyl

methyl

2,4-difluoro-

2,4-difluoro-

phenyl

phenyl

756)

methyl

methyl

2,4-difluoro-

4-chlorophenyl

phenyl

757)

methyl

methyl

2,4-difluoro-

3-chlorophenyl

phenyl

758)

methyl

methyl

2,4-difluoro-

2-chlorophenyl

phenyl

759)

methyl

methyl

2,4-difluoro-

4-chloro-2-

phenyl

methoxyphenyl

760)

methyl

methyl

2,4-difluoro-

4-trifluoro-

phenyl

methylphenyl

761)

methyl

methyl

2,4-difluoro-

2-trifluoro-

phenyl

methylphenyl

762)

methyl

methyl

2,4-difluoro-

3-trifluoro-

phenyl

methylphenyl

763)

methyl

methyl

2,4-difluoro-

4-(trifluoro-

phenyl

methoxy)phenyl

764)

methyl

methyl

2,4-difluoro-

3-(trifluoro-

phenyl

methoxy)phenyl

765)

methyl

methyl

2,4-difluoro-

4-(difluoro-

phenyl

methoxy)phenyl

766)

methyl

methyl

2,4-difluoro-

3-(difluoro-

phenyl

methoxy)phenyl

767)

methyl

methyl

2,4-difluoro-

4-cyanophenyl

phenyl

768)

methyl

methyl

4-trifluoro-

phenyl

methylphenyl

769)

methyl

methyl

4-trifluoro-

4-ethylphenyl

methylphenyl

770)

methyl

methyl

4-trifluoro-

4-methylphenyl

methylphenyl

771)

methyl

methyl

4-trifluoro-

2-methylphenyl

methylphenyl

772)

methyl

methyl

4-trifluoro-

3-methylphenyl

methylphenyl

773)

methyl

methyl

4-trifluoro-

4-fluorophenyl

methylphenyl

774)

methyl

methyl

4-trifluoro-

2,4-difluoro-

methylphenyl

phenyl

775)

methyl

methyl

4-trifluoro-

4-chlorophenyl

methylphenyl

776)

methyl

methyl

4-trifluoro-

3-chlorophenyl

methylphenyl

777)

methyl

methyl

4-trifluoro-

2-chlorophenyl

methylphenyl

778)

methyl

methyl

4-trifluoro-

4-chloro-2-

methylphenyl

methoxyphenyl

779)

methyl

methyl

4-trifluoro-

4-trifluoro-

methylphenyl

methylphenyl

780)

methyl

methyl

4-trifluoro-

2-trifluoro-

methylphenyl

methylphenyl

781)

methyl

methyl

4-trifluoro-

3-trifluoro-

methylphenyl

methylphenyl

782)

methyl

methyl

4-trifluoro-

4-(trifluoro-

methylphenyl

methoxy)phenyl

783)

methyl

methyl

4-trifluoro-

3-(trifluoro-

methylphenyl

methoxy)phenyl

784)

methyl

methyl

4-trifluoro-

4-(difluoro-

methylphenyl

methoxy)phenyl

785)

methyl

methyl

4-trifluoro-

3-(difluoro-

methylphenyl

methoxy)phenyl

786)

methyl

methyl

4-trifluoro-

4-cyanophenyl

methylphenyl

787)

methyl

methyl

3,4-dichloro-

4-fluorophenyl

phenyl

788)

methyl

methyl

3,4-

phenyl

(methylene-

dioxy)phenyl

789)

methyl

methyl

3-trifluoro-

phenyl

methylphenyl

790)

methyl

methyl

3-trifluoro-

4-ethylphenyl

methylphenyl

791)

methyl

methyl

3-trifluoro-

4-methylphenyl

methylphenyl

792)

methyl

methyl

3-trifluoro-

2-methylphenyl

methylphenyl

793)

methyl

methyl

3-trifluoro-

3-methylphenyl

methylphenyl

794)

methyl

methyl

3-trifluoro-

4-fluorophenyl

methylphenyl

795)

methyl

methyl

3-trifluoro-

2,4-difluoro-

methylphenyl

phenyl

796)

methyl

methyl

3-trifluoro-

4-chlorophenyl

methylphenyl

797)

methyl

methyl

3-trifluoro-

3-chlorophenyl

methylphenyl

798)

methyl

methyl

3-trifluoro-

2-chlorophenyl

methylphenyl

799)

methyl

methyl

3-trifluoro-

4-chloro-2-

methylphenyl

methoxyphenyl

800)

methyl

methyl

3-trifluoro-

4-trifluoro-

methylphenyl

methylphenyl

801)

methyl

methyl

3-trifluoro-

2-trifluoro-

methylphenyl

methylphenyl

802)

methyl

methyl

3-trifluoro-

3-trifluoro-

methylphenyl

methylphenyl

803)

methyl

methyl

3-trifluoro-

4-(trifluoro-

methylphenyl

methoxy)phenyl

804)

methyl

methyl

3-trifluoro-

3-(trifluoro-

methylphenyl

methoxy)phenyl

805)

methyl

methyl

3-trifluoro-

4-(difluoro-

methylphenyl

methoxy)phenyl

806)

methyl

methyl

3-trifluoro-

3-(difluoro-

methylphenyl

methoxy)phenyl

807)

methyl

methyl

3-trifluoro-

4-cyanophenyl

methylphenyl

808)

formyl

methyl

phenyl

phenyl

809)

formyl

methyl

phenyl

4-methylphenyl

810)

formyl

methyl

phenyl

2,4-dichloro-

phenyl

811)

formyl

methyl

4-methylphenyl

4-chlorophenyl

812)

formyl

methyl

4-methoxy-

4-methoxyphenyl

phenyl

813)

formyl

methyl

4-methoxy-

2-methoxyphenyl

phenyl

814)

formyl

methyl

4-methoxy-

4-chlorophenyl

phenyl

815)

formyl

methyl

4-methoxy-

2,4-dichloro-

phenyl

phenyl

816)

formyl

methyl

3-chlorophenyl

phenyl

817)

formyl

methyl

3,4-dichloro-

phenyl

phenyl

818)

formyl

methyl

4-chlorophenyl

4-chlorophenyl

819)

formyl

methyl

4-chlorophenyl

3,4-dichloro-

phenyl

820)

formyl

methyl

4-chlorophenyl

2,4-dichloro-

phenyl

821)

formyl

methyl

4-chlorophenyl

4-fluorophenyl

822)

formyl

methyl

4-chlorophenyl

4-formylphenyl

823)

formyl

methyl

4-bromophenyl

4-methoxyphenyl

824)

formyl

methyl

4-bromophenyl

4-formylphenyl

825)

formyl

methyl

phenyl

4-isopropylphe-

nyl

826)

forxnyl

methyl

phenyl

4-fluorophenyl

827)

formyl

methyl

phenyl

3-fluorophenyl

828)

formyl

methyl

phenyl

2-fluorophenyl

829)

formyl

methyl

phenyl

2,3,5,6-tetra-

fluorophenyl

830)

formyl

methyl

phenyl

4-trifluoro-

methylphenyl

831)

formyl

methyl

phenyl

3-trifluoro-

methylphenyl

832)

formyl

methyl

phenyl

4-formyl-

sulfonylphenyl

833)

formyl

methyl

phenyl

4-chlorophenyl

834)

formyl

methyl

phenyl

3-chlorophenyl

835)

formyl

methyl

phenyl

2-chlorophenyl

836)

formyl

methyl

phenyl

3,5-dichloro-

phenyl

837)

formyl

methyl

phenyl

4-(trifluoro-

methoxy)phenyl

838)

formyl

methyl

phenyl

3-(trifluoro-

methoxy)phenyl

839)

formyl

methyl

phenyl

4-(difluoro-

methoxy)phenyl

840)

formyl

methyl

phenyl

3-(difluoro-

methoxy)phenyl

841)

formyl

methyl

phenyl

4-cyanophenyl

842)

formyl

methyl

4-chlorophenyl

4-trifluoro-

methylphenyl

843)

formyl

methyl

4-chlorophenyl

3-trifluoro-

methylphenyl

844)

formyl

methyl

4-chlorophenyl

2-chlorophenyl

845)

formyl

methyl

4-chlorophenyl

3-chlorophenyl

846)

formyl

methyl

4-chlorophenyl

4-trifluoro-

methoxyphenyl

847)

formyl

methyl

4-chlorophenyl

3-trifluoro-

methoxyphenyl

848)

formyl

methyl

4-chlorophenyl

4-difluoro-

methoxyphenyl

849)

formyl

methyl

4-chlorophenyl

3-difluoro-

methoxyphenyl

850)

formyl

methyl

4-fluorophenyl

phenyl

851)

formyl

methyl

4-fluorophenyl

4-ethylphenyl

852)

formyl

methyl

4-fluorophenyl

4-formylphenyl

853)

formyl

methyl

4-fluorophenyl

2-formylphenyl

854)

formyl

methyl

4-fluorophenyl

3-formylphenyl

855)

formyl

methyl

4-fluorophenyl

4-fluorophenyl

856)

formyl

methyl

4-fluorophenyl

2,4-difluoro-

phenyl

857)

formyl

methyl

4-fluorophenyl

4-chlorophenyl

858)

formyl

methyl

4-fluorophenyl

3-chlorophenyl

859)

formyl

methyl

4-fluorophenyl

2-chlorophenyl

860)

formyl

methyl

4-fluorophenyl

4-chloro-2-

methoxyphenyl

861)

formyl

methyl

4-fluorophenyl

4-trifluoro-

methylphenyl

862)

formyl

methyl

4-fluorophenyl

2-trifluoro-

methylphenyl

863)

formyl

methyl

4-fluorophenyl

3-trifluoro-

methylphenyl

864)

formyl

methyl

4-fluorophenyl

4-(trifluoro-

methoxy)phenyl

865)

formyl

methyl

4-fluorophenyl

3-(trifluoro-

methoxy)phenyl

866)

formyl

methyl

4-fluorophenyl

4-(difluoro-

methoxy)phenyl

867)

formyl

methyl

4-fluorophenyl

3-(difluoro-

methoxy)phenyl

868)

formyl

methyl

4-fluorophenyl

4-cyanophenyl

869)

formyl

methyl

3-fluorophenyl

phenyl

870)

formyl

methyl

3-fluorophenyl

4-ethylphenyl

871)

formyl

methyl

3-fluorophenyl

4-formylphenyl

872)

formyl

methyl

3-fluorophenyl

2-formylphenyl

873)

formyl

methyl

3-fluorophenyl

3-formylphenyl

874)

formyl

methyl

3-fluorophenyl

4-fluorophenyl

875)

formyl

methyl

3-fluorophenyl

2,4-difluoro-

phenyl

876)

formyl

methyl

3-fluorophenyl

4-chlorophenyl

877)

formyl

methyl

3-fluorophenyl

3-chlorophenyl

878)

formyl

methyl

3-fluorophenyl

2-chlorophenyl

879)

formyl

methyl

3-fluorophenyl

4-chloro-2-

methoxyphenyl

880)

formyl

methyl

3-fluorophenyl

4-trifluoro-

methylphenyl

881)

formyl

methyl

3-fluorophenyl

2-trifluoro-

methylphenyl

882)

formyl

methyl

3-fluorophenyl

3-trifluoro-

methylphenyl

883)

formyl

methyl

3-fluorophenyl

4-(trifluoro-

methoxy)phenyl

884)

formyl

methyl

3-fluorophenyl

3-(trifluoro-

methoxy)phenyl

885)

formyl

methyl

3-fluorophenyl

4-(difluoro-

methoxy)phenyl

886)

formyl

methyl

3-fluorophenyl

3-(difluoro-

methoxy)phenyl

887)

formyl

methyl

3-fluorophenyl

4-cyanophenyl

888)

formyl

methyl

2-fluorophenyl

phenyl

889)

formyl

methyl

2-fluorophenyl

4-ethylphenyl

890)

formyl

methyl

2-fluorophenyl

4-formylphenyl

891)

formyl

methyl

2-fluorophenyl

2-formylphenyl

892)

formyl

methyl

2-fluorophenyl

3-formylphenyl

893)

formyl

methyl

2-fluorophenyl

4-Fluorphenyl

894)

Formyl

Methyl

2-fluorophenyl

2,4-difluoro-

phenyl

895)

formyl

methyl

2-fluorophenyl

4-chlorophenyl

896)

formyl

methyl

2-fluorophenyl

3-chlorophenyl

897)

formyl

methyl

2-fluorophenyl

2-chlorophenyl

898)

formyl

methyl

2-fluorophenyl

4-chloro-2-

methoxyphenyl

899)

formyl

methyl

2-fluorophenyl

4-trifluoro-

methylphenyl

900)

formyl

methyl

2-fluorophenyl

2-trifluoro-

methylphenyl

901)

formyl

methyl

2-fluorophenyl

3-trifluoro-

methylphenyl

902)

formyl

methyl

2-fluorophenyl

4-(trifluoro-

methoxy)phenyl

903)

formyl

methyl

2-fluorophenyl

3-(trifluoro-

methoxy)phenyl

904)

formyl

methyl

2-fluorophenyl

4-(difluoro-

methoxy)phenyl

905)

formyl

methyl

2-fluorophenyl

3-(difluoro-

methoxy)phenyl

906)

formyl

methyl

2-fluorophenyl

4-cyanophenyl

907)

formyl

methyl

2,4-difluoro-

phenyl

phenyl

908)

formyl

methyl

2,4-difluoro-

4-ethylphenyl

phenyl

909)

formyl

methyl

2,4-difluoro-

4-formylphenyl

phenyl

910)

formyl

methyl

2,4-difluoro-

2-formylphenyl

phenyl

911)

formyl

methyl

2,4-difluoro-

3-formylphenyl

phenyl

912)

formyl

methyl

2,4-difluoro-

4-fluorophenyl

phenyl

913)

formyl

methyl

2,4-difluoro-

2,4-difluoro-

phenyl

phenyl

914)

formyl

methyl

2,4-difluoro-

4-chlorophenyl

phenyl

915)

formyl

methyl

2,4-difluoro-

3-chlorophenyl

phenyl

916)

formyl

methyl

2,4-difluoro-

2-chlorophenyl

phenyl

917)

formyl

methyl

2,4-difluoro-

4-chloro-2-

phenyl

methoxyphenyl

918)

formyl

methyl

2,4-difluoro-

4-trifluoro-

phenyl

methylphenyl

919)

formyl

methyl

2,4-difluoro-

2-trifluoro-

phenyl

methylphenyl

920)

formyl

methyl

2,4-difluoro-

3-trifluoro-

phenyl

methylphenyl

921)

formyl

methyl

2,4-difluoro-

4-(trifluoro-

phenyl

methoxy)phenyl

922)

formyl

methyl

2,4-difluoro-

3-(trifluoro-

phenyl

methoxy)phenyl

923)

formyl

methyl

2,4-difluoro-

4-(difluoro-

phenyl

methoxy)phenyl

924)

formyl

methyl

2,4-difluoro-

3-(difluoro-

phenyl

methoxy)phenyl

925)

formyl

methyl

2,4-difluoro-

4-cyanophenyl

phenyl

926)

formyl

methyl

4-trifluoro-

phenyl

methylphenyl

927)

formyl

methyl

4-trifluoro-

4-ethylphenyl

methylphenyl

928)

formyl

methyl

4-trifluoro-

4-formylphenyl

methylphenyl

929)

formyl

methyl

4-trifluoro-

2-formylphenyl

methylphenyl

930)

formyl

methyl

4-trifluoro-

3-formylphenyl

methylphenyl

931)

formyl

methyl

4-trifluoro-

4-fluorophenyl

methylphenyl

932)

formyl

methyl

4-trifluoro-

2,4-difluoro-

methylphenyl

phenyl

933)

formyl

methyl

4-trifluoro-

4-chlorophenyl

methylphenyl

934)

formyl

methyl

4-trifluoro-

3-chlorophenyl

methylphenyl

935)

formyl

methyl

4-trifluoro-

2-chlorophenyl

methylphenyl

936)

formyl

methyl

4-trifluoro-

4-chloro-2-

methylphenyl

methoxyphenyl

937)

formyl

methyl

4-trifluoro-

4-trifluoro-

methylphenyl

methylphenyl

938)

formyl

methyl

4-trifluoro-

2-trifluoro-

methylphenyl

methylphenyl

939)

formyl

methyl

4-trifluoro-

3-trifluoro-

methylphenyl

methylphenyl

940)

formyl

methyl

4-trifluoro-

4-(trifluoro-

methylphenyl

methoxy)phenyl

941)

formyl

methyl

4-trifluoro-

3-(trifluoro-

methylphenyl

methoxy)phenyl

942)

formyl

methyl

4-trifluoro-

4-(difluoro-

methylphenyl

methoxy)phenyl

943)

formyl

methyl

4-trifluoro-

3-(difluoro-

methylphenyl

methoxy)phenyl

944)

formyl

methyl

4-trifluoro-

4-cyanophenyl

methylphenyl

945)

formyl

methyl

3,4-dichloro-

4-fluorophenyl

phenyl

946)

formyl

methyl

3,4-(formylene-

phenyl

dioxy)phenyl

947)

formyl

methyl

3-trifluoro-

phenyl

methylphenyl

948)

formyl

methyl

3-trifluoro-

4-ethylphenyl

methylphenyl

949)

formyl

methyl

3-trifluoro-

4-formylphenyl

methylphenyl

950)

formyl

methyl

3-trifluoro-

2-formylphenyl

methylphenyl

951)

formyl

methyl

3-trifluoro-

3-formylphenyl

methylphenyl

952)

formyl

methyl

3-trifluoro-

4-fluorophenyl

methylphenyl

953)

formyl

methyl

3-trifluoro-

2,4-difluoro-

methylphenyl

phenyl

954)

formyl

methyl

3-trifluoro-

4-chlorophenyl

methylphenyl

955)

formyl

methyl

3-trifluoro-

3-chlorophenyl

methylphenyl

956)

formyl

methyl

3-trifluoro-

2-chlorophenyl

ethylphenyl

957)

formyl

methyl

3-trifluoro-

4-chloro-2-

methylphenyl

methoxyphenyl

958)

formyl

methyl

3-trifluoro-

4-trifluoro-

methylphenyl

methylphenyl

959)

formyl

methyl

3-trifluoro-

2-trifluoro-

methylphenyl

methylphenyl

960)

formyl

methyl

3-trifluoro-

3-trifluoro-

methylphenyl

methylphenyl

961)

formyl

methyl

3-trifluoro-

4-(trifluoro-

methylphenyl

methoxy)phenyl

962)

formyl

methyl

3-trifluoro-

3-(trifluoro-

methylphenyl

methoxy)phenyl

963)

formyl

methyl

3-trifluoro-

4-(difluoro-

methylphenyl

methoxy)phenyl

964)

formyl

methyl

3-trifluoro-

3-(difluoro-

methylphenyl

methoxy)phenyl

965)

formyl

methyl

3-trifluoro-

4-cyanophenyl

methylphenyl

966)

formyl

methyl

4-formylphenyl

phenyl

967)

formyl

methyl

4-methoxy-

phenyl

phenyl

968)

formyl

methyl

4-chlorophenyl

phenyl

969)

H

H

2-chloro-6-

phenyl

m.p.

fluorophenyl

139-

141° C.

970)

H

H

2-chloro-6-

4-fluorophenyl

m.p.

fluorophenyl

73-

75° C.

971)

H

H

phenyl

4-cyanophenyl

m.p.

174-

176° C.

972)

H

H

phenyl

4-bromophenyl

m.p.

190-

191° C.

973)

H

H

phenyl

4-iodophenyl

m.p.

194-

196° C.

974)

acetyl

H

phenyl

phenyl

m.p.

147-

148° C.

975)

formyl

H

phenyl

phenyl

m.p.

140-

141° C.

976)

H

H

4-phenylphenyl

4-fluorophenyl

m.p.

231-

233° C.

977)

H

H

2,6-dichloro-

phenyl

m.p.

phenyl

131-

132° C.

978)

H

H

4-phenylphenyl

phenyl

m.p.

247-

249° C.

979)

methyl

H

4-phenylphenyl

phenyl

m.p.

183-

185° C.

980)

acetyl

H

4-chlorophenyl

phenyl

m.p.

129-

131° C.

The compounds of the formula I can preferably be prepared according to the following reaction scheme:

The compounds of the formula II listed in Table 2 below are novel compounds:

TABLE 2

(II)

No.

R

1

R

2

R

a

R

b

1)

H

H

phenyl

4-isopropylphenyl

2)

H

H

phenyl

2,3,5,6-tetrafluorophenyl

3)

H

H

phenyl

4-trifluoromethylphenyl

4)

H

H

phenyl

4-chlorophenyl

5)

H

H

phenyl

3-chlorophenyl

6)

H

H

phenyl

2-ch1orophenyl

7)

H

H

phenyl

3,5-dichlorophenyl

8)

H

H

phenyl

4-(trifluoromethoxy)phenyl

9)

H

H

4-chlorophenyl

4-trifluoromethylphenyl

10)

H

H

4-chlorophenyl

2-chlorophenyl

11)

H

H

4-chlorophenyl

3-chlorophenyl

12)

H

H

4-fluorophenyl

phenyl

13)

H

H

4-fluorophenyl

4-fluorophenyl

14)

H

H

3,4-dichloro-

4-fluorophenyl

phenyl

15)

methyl

H

phenyl

phenyl

16)

formyl

H

4-chlorophenyl

phenyl

17)

H

H

2-chloro-

phenyl

6-fluorophenyl

18)

H

H

2-chloro-

4-fluorophenyl

6-fluorophenyl

19)

H

H

phenyl

4-cyanophenyl

20)

H

H

phenyl

4-bromophenyl

21)

H

H

phenyl

4-iodophenyl

22)

acetyl

H

phenyl

phenyl

23)

formyl

H

phenyl

phenyl

24)

H

H

4-phenylphenyl

4-fluorophenyl

25)

H

H

2,6-dichloro-

phenyl

phenyl

26)

H

H

4-phenylphenyl

phenyl

27)

methyl

H

4-phenylphenyl

phenyl

28)

acetyl

H

4-chlorophenyl

phenyl

Compounds of the formula II are in particular those in which R

1

is a hydrogen atom or a C

1

-C

4

-alkyl group or a formyl group (—CHO). Preference is furthermore given to compounds II in which the radicals R

2

, R

a

and R

b

independently of one another have the following meanings:

R

2

is hydrogen;

R

a

is phenyl which may be mono- or polysubstituted, preferably mono- or disubstituted, by halogen or by a phenyl group which for its part may also be substituted by halogen or C

1

-C

4

-haloalky, C

1

-C

4

-haloalkoxy.

R

b

is phenyl which may be mono- or polysubstituted, preferably mono- to tetrasubstituted, by halogen, C

1

-C

6

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-haloalkoxy.

In this context, the radicals R

1

, R

a

and R

b

in the case of the compounds II have, for example, the following meanings:

R

1

: hydrogen, methyl, formyl;

R

2

: hydrogen;

R

a

: phenyl, 4-chlorophenyl, 4-fluorophenyl, 3,4-dichlorophenyl, 2-chloro-6-fluorophenyl, 4-phenylphenyl, 2,6-dichlorophenyl or 2-chlorophenyl.

R

b

: 4-isopropylphenyl, 2,3,5,6-tetrafluorophenyl, 4-trifluoromethylphenyl, 4-chlorophenyl, 3-chlorophenyl, 2-chlorophenyl, 3,5-dichlorophenyl, 4-(trifluoromethoxy)phenyl, 4-trifluoromethylphenyl, phenyl, 4-fluorophenyl, 4-cyanophenyl, 4-bromophenyl, 4-iodophenyl.

The compounds I have an excellent fungicidal activity. This is true, in particular, for the compounds Nos. 1, 13, 14, 17, 23, 26, 30, 31, 34, 35, 36, 38, 43, 45, 46, 51, 56, 969, 970, 971, 30 972, 973 and 977 listed in Table 1. Particularly preferred compounds are the following: Nos. 13, 14, 23, 26, 31, 35, 36, 38, 46, 56, 969, 970, 971, 972, 973 and 977 listed in table 1. Particularly preferred compounds are the following: Nos. 13, 14, 23, 26, 31, 35, 36, 38, 46, 56, 969, 970, 971, 972 and 973.

Normally, the plants are sprayed or dusted with the active compounds, or the seeds of the plants are treated with the active compounds.

The formulations (fungicidal compositions or agrochemical compositions) are prepared in a known manner, e.g. by extending the active compound with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents if water is used as diluent. Suitable auxiliaries are essentially: solvents, such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. mineral oil fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) and water; carriers, such as ground natural minerals (e.g. kaolins, clays, talc, chalk) and ground synthetic minerals (e.g. highly-disperse silica, silicates); emulsifiers, such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants, such as lignosulfite waste liquors and methylcellulose.

Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, or of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ether, condensates of sulfonated naphthalene and of its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isococtyl-, octyl- or nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors or methycellulose.

Powders, materials for spreading and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths, such as silica gel, silicic acids, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, ureas, and meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

Examples of such preparations are:

I. a solution of 90 parts by weight of a compound I according to the invention and 10 parts by weight of N-methyl-pyrrolidone which is suitable for use in the form of microdrops;

II. a mixture of 10 parts by weight of a compound I according to the invention, 70 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzesulfonate, 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil; a dispersion is obtained by finely distributing the solution in water.

III. an aqueous dispersion of 10 parts by weight of a compound I according to the invention, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil;

IV. an aqueous dispersion of 10 parts by weight of a compound I according to the invention, 25 parts by weight of cyclohexanol, 55 parts by weight of a mineral oil fraction of boiling point 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil;

V. a mixture, ground in a hammer mill, of 80 parts by weight of a compound I according to the invention, which is preferably in solid form, 3 parts by weight of sodium diisobutylnaphthalene-2-sulfonate, 10 parts by weight of a sodium lignosulfonate from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel; a spray mixture is obtained by finely distributing the mixture in water;

VI. an intimate mixture of 3 parts by weight of a compound I according to the invention and 97 parts by weight of finely divided kaolin; this dust comprises 3% by weight of active compound;

VII. an intimate mixture of 30 parts by weight of a compound I according to the invention, 62 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel; this preparation imparts good adhesion properties to the active compound;

VIII. a stable aqueous dispersion of 40 parts by weight of a compound I according to the invention, 10 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which can be diluted further;

IX. a stable oily dispersion of 20 parts by weight of a compound I according to the invention, 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condesate and 50 parts by weight of a paraffinic mineral oil.

The active compounds of the formula I are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them act systemically, and they can therefore also be employed as foliar- and soil-acting fungicides.

They are particlarly important for the control of a large number of fungi on a variety of crop plants, such as wheat, rye, barley, oats, rice, maize, grass, cotton, soya, coffee, sugar cane, grape vine, fruit-bearing species, ornamentals and vegetables, such as cucumbers, beans and cucurbits, and on the seed of these plants.

The compounds are applied by treating the fungi or the seed, plants, materials or soil to be protected against fungal infection with a fungicidally active amount of the active compounds. They are applied before or after infection of the materials, plants or seeds with the fungi.

Specifically, the novel compounds are suitable for controlling the following plant diseases:

Erysiphe graminis

(powdery mildew) in cereals,

Erysiphe cichoracearum

and

Sphaerotheca fuliginea

in cucurbits,

Podosphaera leucotricha

in apples,

Uncinula necator

in grapevine, Puccinia species in cereals, Rhizoctonia species in cotton and lawn, Ustilago species in cereals and sugar cane,

Venturia inaegualis

(scab) in apples, Helminthosporium species in cereals,

Septoria nodorum

in wheat,

Botrytis cinerea

(gray mold) in strawberries, grapevine, ornamentals and vegetables,

Cercospora arachidicola

in groundnuts,

Pseudocercosporella herpotrichoides

in wheat and barley,

Pyricularia oryzae

in rice,

Phytophthora infestans

in potatoes and tomatoes, Fusarium and Verticillium species in a variety of plants,

Plasmopara viticola

in grapevine and Alternaria species in vegetables and fruit.

The active compounds of the formula I can be present either in free from or in the form of their agriculturally utilizable or environmentally compatible salts. Such salts are, for example, acid addition salts with inorganic or organic acids, for example hydrochloric acid, sulfuric acid, acetic acid, and other acids.

The active compounds of the formula I can also be employed in the protection of materials (protection of wood), e.g. against

Paecilomyces variotii.

In general, the fungicidal compositions comprise of from 0.1 to 95, preferably from 0.5 to 90, % by weight of active compound.

Depending on the nature of the desired effect, the rates of application are between 0.025 and 2, preferably 0.1 to 1, kg of active compound per ha.

In the treatment of seed, amounts of 0.001 to 50 g, preferably 0.01 to 10 g, of active compound are generally required per kilogram of seed.

The compositions according to the invention can also be present in the application form as fungicides together with other active compounds, e.g. herbicides, insecticides, growth regulators and fungicides, or else with fertilizers.

In many cases, mixing them with other fungicidally active compounds results in a widened fungicidal spectrum of action. In particular when used in combination with other fungicidally active compounds, the active compounds of the formula I reduce the risk of development of resistance compared to the use of the individual active compounds.

If the crop plants or the seeds are treated with combination preparations of active compounds of the formula I and other fungicidally active compounds, this application can be carried out simultaneously or successively. If the active compounds of the formula I are used simultaneously with other fungicides, this is advantageously carried out by preparing an agrochemical mixture of the two active compounds, which mixture is used in a customary manner for treating the crop plants or the seeds. If the active compounds are applied successively, this is advantageously carried out by using the individual active compounds either within a short period of time or in intervals of several days or weeks.

The overall frequency of the treatment of plants or of seeds with fungicides can be reduced by this combined application.

For the purpose of the present invention, the term “combination preparation” is to be understood as meaning, in principle, all agrochemical composition which comprise active compounds of the formula I or II and one or more active compounds, in particular those having fungicidal action, for example in the form of customary agrochemical mixtures. Furthermore, the term “combination preparations” also includes those agrochemical preparations which comprise active compounds of the formula I and furthermore a note that these active compounds are suitable for combined application with other active compounds in the agricultural sector. Such a note may be present, for example, in the form of a label on the packaging on the commercial product or on the container containing the active compound of the formula I and/or the agrochemical composition which comprises an active compound of the formula I. Alternatively, it is also possible for other agrochemical products to contain corresponding notes concerning the combined application with compounds of the formula I or II. In this context, such products are likewise combination preparations which are suitable for use in combination with active compounds of the formula I and/or II.

The following list of fungicides together with which the compounds according to the invention can be used is intended to illustrate possible combinations, but not to impose any limitation:

sulfur, dithiocarbamates and their derivatives, such as iron(III) dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N-propylenebisdithiocarbamate), zinc (N,N-propylenebisdithiocarbamate), N,N-polypropylenebis(thiocarbamoyl) disulfide;

nitro derivatives, such as dinitro-(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate, diisopropyl 5-nitro-isophthalate;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithio-anthraquinone, 2-thio-1,3-dithiolo-[4,5-b]-quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2-(fur-2-yl)benzimidazole, 2-(thiazol-4-yl )benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide, N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenylsulfuric diamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine 2-thion-1-oxide, 8-hydroxyquinoline and its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-

3

-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanlilide, 2,4,5-trimethylfuran-3-carboxanilide cyclohexyl-2,5-dimethylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloromethyl acetal, piperazine-1,4-diylbis(1-(2,2,2-trichloroethyl)formamide, 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine and its salts, 2,6-dimethyl-N-cyclododecylmorpholine and its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine, N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2 4-triazole, 1-[2-(2,4-dichlorophenyl)-4-n-Proply-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N′-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, (2-chlorophenyl)-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene, [2-(4-chlorophenyl)ethyl]-(1,1-dimethylethyl)-1H-1,2,4-triazol-1-ethanol, 1-[3-(2-chlorophenyl)-1-(4-fluorophenyl)oxiran-2-ylmethyl]-1H-1,2,4-triazole, and

various fungicides, such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl)]glutarimide, hexachlorobenzene, methyl N-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninate, methyl N-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl)-D,L-alaninate, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-amino-butyrolactone, methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)-DL-alaninate, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-(3,5-dichlorophenyl)-5-methyl-5-methoxy-methyl-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano- [N-(ethylaminocarbonyl)-2-methoximino]acetamide, 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole, 2,4-difluoro-a-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, 1-((bis(4-fluorophenyl)methylsilyl)-methyl)-1H-1,2,4-triazole,

strobilurins, such as methyl E-methoximino-[α-(o-tolyloxy)-o-tolyl]acetate, methyl E-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate, methyl-E-methoximino-[α-(2-phenoxyphenyl)]acetamide, N-methyl-E-methoximino-[α-(2,5-dimethyloxy)-o-tolyl]acetamide,

anilinopyrimidines, such as N-(4,6-dimethylpyrimidin-2-yl)aniline, N-[4-methyl-6-(1-propinyl)pyrimidin-2-yl]aniline, N-(4-methyl-6-cyclopropylpyrimidin-2-yl)aniline,

phenylpyrroles, such as 4-(2,2difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile,

cinnamamides, such as 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-acryloylmorpholide.

The invention is illustrated in more detail by the working examples below:

EXAMPLE 1

1-Anilino-3-(3,4-dichlorophenyl)-pyrrole-2,5-dione (Table 1, No. 12)

a) Potassium 3-Cyano-3-(3,4-dichlorophenyl)acrylate

18.6g (0.1 mol) of (3,4-dichlorophenyl)acetonitrile and 35 g (0.25 mol) of potassium carbonate were initially charged in 200 ml of methanol and admixed with 22.2 g (0.15 mol) of 50% strength agueous glyoxylic acid, and the mixture was stirred at room temperature for 5 h. The residue was filtered off, washed with methylene chloride, stirred with 1 l of water at room temperature overnight and filtered off, and the precipitated product was washed with water and dried. Yield 26.2 g, m.p. 235-238° C.

b) (3,4-Dichlorophenyl)furan-2,5-dione

25.8 g (92 mmol) of potassium 3-cyano-3-(3,4-dichlorophenyl)acrylate were dissolved in 200 ml of 88% strength formic acid and admixed dropwise with 15 ml of concentrated sulfuric acid. The mixed was then heated under reflux for 3 h, poured at 90° C. into 2.5 l of water and stirred for 1 h, and the product was filtered off, washed with water and dried. Yield: 18.9 g, m.p. 112° C.

c) 1-Anilino-3-(3,4-dichlorophenyl)pyrrole-2,5-dione

2.43 g (10 mmol) of -(3,4-dichlorophenyl)furan-2,5-dione and 1.08 g (10 mmol) of phenyl hydrazine in 50 ml of glacial acetic acid were boiled under ref lux for 5 h. The mixture was cooled and the product was then filtered off and washed first with glacial acetic acid and subquently with pentane. Yield: 1.8 g of a crystalline solid, m.p. 208-210° C.

EXAMPLE 2

Activity Against

Phytophthora infestans

on Tomatoes

Leaves of potted plants cv. “Groβe Fleischtomate” were sprayed to runoff point with an aqueous suspension which had been prepared from a stock solution comprising 10% of active compound, 63% of cycbohexanone and 27% of emulsifier. The next day, the leaves were infected with an aqueous zoospore suspension of

Phytophthora infestans

. The plants were subsequently placed in a chamber saturated with water vapor, at 16-18° C. After 6 days, the late blight on the untreated but infected control plants had developed to such an extent that the infection could be determined visually in %.

% infection of the leaves after appli-

cation of an aqueous preparation con-

Active compound

taining 250 ppm of active compound

Table 1. No. 1

15

Table 1. No. 13

2

Table 1. No. 17

5

Table 1. No. 31

7

Table 1. No. 34

5

Table 1. No. 485

10

Table 1. No. 969

3

Table 1. NO. 971

3

Table 1. No. 972

5

Table 1. No. 973

8

Untreated

90

The table above shows that the damage caused by harmful fungi on the treated plants is considerably lower than on the untreated plants. Consequently, the active compounds according to the invention have good fungicidal activity. In particular, they have a protective effect against harmful fungi.

EXAMPLE 3

Activity Against

Plasmopara viticola

Leaves of potted grapevines cv. “Müller-Thurgau” were sprayed to runoff point with an aqueous active compound preparation which had been prepared from a stock solution comprising 10% of active compound, 63% of cyclohexanone and 27% of emulsifier. To be able to assess the persistency of the substances, the plants were, after the spray coating had dried on, placed in a greenhouse for 7 days. Only then were the leaves inoculated with an aqueous zoospore suspension of

Plasmopara viticola

. The grapevines were then initially placed in a water-vapor-saturated chamber at 24° C. for 48 hours and subsequently in a greenhouse at 20-30° for 5 days. After this time, the plants were returned into a humid chamber for 16 hours to accelerate the sporangiophore eruption. The extent to which the disease had developed on the underside of the leaves was then determined visually.

% infection of the leaves after appli-

cation of an aqueous preparation con-

Active compound

taining 250 ppm of active compound

Table 1. No. 1

5

Table 1. No. 17

5

Table 1. No. 30

15

Table 1. No. 34

5

Table 1. No. 43

15

Table 1. No. 45

10

Table 1. No. 51

15

Table 1. No. 969

5

Table 1. No. 971

10

Table 1. No. 972

1

Table 1. No. 973

1

Table 1. No. 977

3

Untreated

85

Fungicides containing pyrrolidones as their active agents

Information

Patent Number

Date Filed

Date Issued

Inventors

Original Assignees

Examiners

Agents

CPC

US Classifications

Field of Search

US

International Classifications

Abstract

Description

Claims

Priority Claims (1)

PCT Information

US Referenced Citations (1)

Foreign Referenced Citations (1)

Non-Patent Literature Citations (2)

Entry
Naik, et al, 1987, Med. Sci. Res., CAS-online abstract, 15(1), 27-8.*
Augustin, Et Al., Z.Chem., 13, Jg. (1973), pp. 214-216, XP-000901338.