一台132Kw空压机，运行电流分别为85A 280A 285A，请师傅们帮忙找原因。_百度知道
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我们会通过消息、邮箱等方式尽快将举报结果通知您。Ortho-substituted 1-naphthyl ethers and fungicides containing these
United States Patent 5057537
Ortho-substituted 1-napthyl ethers of the formula ##STR1## where X is CH or N, Y is saturated or unsaturated alkylene and R is aryl, aryloxy, arylthio or arylalkoxy, the aromatic ring being substituted or unsubstituted, and fungicides containing these compounds.
Inventors:
Wenderoth, Bernd (Lampertheim, DE)
Sauter, Hubert (Mannheim, DE)
Harreus, Albrecht (Ludwigshafen, DE)
Roehl, Franz (Ludwigshafen, DE)
Ammermann, Eberhard (Ludwigshafen, DE)
Lorenz, Gisela (Neustadt, DE)
Application Number:
Publication Date:
10/15/1991
Filing Date:
02/02/1990
Export Citation:
BASF Aktiengesellschaft (Ludwigshafen, DE)
Primary Class:
Other Classes:
International Classes:
A01N37/10; A01N37/38; A01N37/44; A01N37/50; C07C69/734; C07C205/37; C07C251/48; C07C255/54; C07C323/12; C07C323/19; C07C323/20; (IPC1-7): A01N37/05
Field of Search:
560/35, 560/10, 560/21, 514/510, 558/384
View Patent Images:
&&&&&&PDF help
US Patent References:
4913721Clough et al.4829085Wenderoth et al.514/5224822908Karbach et al.4802913Clough et al.3978116Fried et al.
Foreign References:
EP0178826Fungicides.EP0254426Fungicides.EP0336211Ortho-substituted phenol ethers and fungicides containing them.GB2192883A
Primary Examiner:
Gray, Bruce
Attorney, Agent or Firm:
Oblon, Spivak, McClelland, Maier & Neustadt
1. Ortho-substituted 1-naphthyl ethers of the general formula I ##STR11## where X is N, Y is saturated or unsaturated C1 -C12 -alkylene and R is aryl, aryloxy, arylthio or arylalkoxy, it being possible for the aromatic ring to be substituted one to five times by the following: halogen, C1 -C6 -alkyl, C1 -C6 -alkoxy, C1 -C4 -alkylthio, C1 -C2 -haloalkyl, aryl, aryl-C1 -C2 -alkoxy, C1 -C4 -alkylcarbonyl, amino which is substituted once or twice by C1 -C4 -alkyl, or is cyano or nitro.
2. A process for combating fungi, wherein the fungi or the materials, plants, seed or soil threatened by fungus attack are treated with a fungicidally effective amount of a compound of the formula I ##STR12## where X is N, Y is saturated or unsaturated C1 -C12 -alkylene and R is aryl, aryloxy, arylthio or arylalkoxy, it being possible for the aromatic ring to be substituted one to five times by the following: halogen, C1 -C6 -alkyl, C1 -C6 -alkoxy, C1 -C4 -alkylthio, C1 -C2 -haloalkyl, aryl, aryl-C1 -C2 -alkoxy, C1 -C4 -alkylcarbonyl, amino which is substituted once or twice by C1 -C4 -alkyl, or is cyano or nitro.
3. A fungicide containing an inert carrier and a fungicidally effective amount of a compound of the formula I ##STR13## where X is N, Y is saturated or unsaturated C1 -C12 -alkylene and R is aryl, aryloxy, arylthio or arylalkoxy, it being possible for the aromatic ring to be substituted one to five times by the following: halogen, C1 -C6 -alkyl, C1 -C6 -alkoxy, C1 -C4 -alkylthio, C1 -C2 -haloalkyl, aryl, aryl-C1 -C2 -alkoxy, C1 -C4 -alkylcarbonyl, amino which is substituted once or twice by C1 -C4 -alkyl, or is cyano or nitro.
4. A compound of the formula I as set forth in claim 1, where R is 2-fluorophenyl, Y is CH2 and X is N.
5. A compound of the formula I as set forth in claim 1, where R is 2-chlorophenyl Y is CH2 and X is N.
6. A compound of the formula I as set forth in claim 1, where R is 2-bromophenyl, Y is CH2 and X is N.
Description:
The present invention relates to novel ortho-substituted 1-naphthyl ethers, the prepartion thereof, fungicides containing these, and the use thereof as fungicides. The use of oxime ethers such as methyl 2-benzyloxyphenyl glyoxylate O-methyloxime as fungicides has been disclosed (EP 4426). However, their fungicidal action is often inadequate. We have found that ortho-substituted 1-naphthyl ethers of the general formula I ##STR2## where X is CH or N, Y is C1 -C12 -alkylene which can be unsaturated and R is aryl, aryloxy, arylthio or arylalkoxy, it being possible for the aromatic ring to be substituted one to five times by the following: halogen, C1 -C6 -alkyl, C1 -C6 -alkoxy, C1 -C4 -alkylthio, C1 -C2 -haloalkyl, aryl, aryl-C1 -C2 -alkoxy, C1 -C4 -alkylcarbonyl, amino which is substituted once or twice by C1 -C4 -alkyl, or cyano or nitro, have an excellent fungicidal action. Examples of possible meanings of the radicals listed for the general formula are the following: X can be CH or N, Y can be straight-chain C1 -C12 -alkylene, in particular C1 -C4 -alkylene (e.g. methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene), branched C2 -C12 -alkylene (e.g. methylethylene) or C4 -C12 -alkenylene (e.g. butenylene), R can be aryl (phenyl), aryloxy (phenoxy, 1-naphthyloxy, 2-naphthyloxy), arylthio (phenylthio) or arylalkoxy (benzyloxy), it being possible for the aromatic ring to be substituted one to five (one to three) times by the following:
halogen (e.g. fluorine, chlorine, bromine, iodine), C1 -C6 -alkyl (e.g. methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n-, iso-, sec-, tert- or neo-pentyl, hexyl), C1 -C6 -alkoxy (e.g. methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy), C1 -C4 -alkylthio (e.g. methylthio, ethylthio), C1 -C2 -haloalkyl (e.g. difluoromethyl, trifluoromethyl), aryl (e.g. phenyl), aryl-C1 -C2 -alkoxy (e.g. benzyloxy), C1 -C4 -alkylcarbonyl (e.g. acetyl), amino which is substituted once or twice by C1 -C4 -alkyl (e.g. dimethylamino), or cyano or nitro. The novel compounds of the formula I can, because of the C?N double bond, result as E/Z isomer mixtures which can be separated in a conventional manner, e.g. by crystallization or chromatography, into the individual components. Both the individual isomers and the mixtures thereof are embraced by the invention and can be used as fungicides. The novel compounds of the general formula I can be prepared by the following processes, for example: starting from 1-naphthol it is possible by Friedel-Crafts acylation with methyl oxalyl chloride in a suitable solvent (for example dichloromethane) in the presence of a Lewis acid (for example titanium tetrachloride) to synthesize the α-keto ester III which is known from the literature (O. Piccolo et al., Tetrahedron 42 (1986), 885-891). ##STR3## Starting from the compound of the formula III it is possible to obtain the novel and valuable intermediates of the formula IV which are likewise embraced by this invention and in which X is CH or N ##STR4## The α-keto ester III can be converted into the novel oxime ether derivative of the formula IV (X?N) by reacting it with O-methylhydroxylamine, or by reacting first with hydroxylamine to give the corresponding oxime and then with a methylating agent such as methyl iodide or dimethyl sulfate (cf. EP 253213). ##STR5## The α-keto ester III can be converted into the novel enol ether derivative of the formula IV (X?CH) by subjecting it to a Wittig reaction with methoxymethyltriphenylphosphonium halide (cf. EP 44448). ##STR6## The novel compounds of the general formula I can be prepared, for example, by reacting the compound of the general formula IV with halides of the formula II in a suitable solvent such as methanol or N,N-dimethylformamide by conventional processes (cf. Houben-Weyl, Methoden der organischen Chemie, volume 6/3, p. 54, Thieme-Verlag, Stuttgart 1965). ##STR7## R, Y and X have the abovementioned meanings. Hal is Cl, Br or I. The novel compounds of the general formula I can also be prepared, for example, by reacting the α-keto ester of the formula III with halides of the formula II in a suitable solvent such as methanol or N,N-dimethylformamide by conventional processes (cf. Houben-Weyl, Methoden der organischen Chemie, volume 6/3, p. 54, Thieme-Verlag, Stuttgart 1965) to give the novel α-keto carboxylic esters of the formula V: ##STR8## These esters of the general formula V can be converted into the compounds of the general formula I accord reaction with O-methylhydroxylamine or with hydroxylamine and subsequent methylation with a methylating agent such as methyl iodide or dimethyl sulfate result in the novel oxime ether derivatives of the formula I (X?N) (cf. EP 253213), and a Wittig reaction with methoxymethyltriphenylphosphonium halide results in the novel enol ether derivatives of the formula I (X?CH) (cf. EP 44448). The α-keto carboxylic esters of the formula V are novel and valuable intermediates and are likewise embraced by this invention.
The preparation of the novel compounds of the formulae I and IV is illustrated by the following examples: Preparation Examples a) 28.5 g (0.15 mol) of titanium tetrachloride are added under nitrogen at -10° C. to 150 ml of methylene chloride. This is followed by dropwise addition at -40° C. of, firstly, 22.3 g (0.15 mol) of 1-naphthol dissolved in 100 ml of methylene chloride and then 18.5 g (0.15 mol) of methyl oxalyl chloride. After stirring at this temperature for 30 min, a little dilute hydrochloric acid is added at room temperature (20° C.), and the mixture is poured onto ice. The organic phase is washed 1× with H2 O, dried over sodium sulfate and concentrated. 30 g (0.13 mol) of methyl 1-hydroxy-2-naphthylglyoxylate (87% yield) are obtained. 1 H NMR (CDCl3): δ=4.05 (s, 3H), 7.25 (d, 1H), 7.40-7.80 (m, 4H), 8.45 (d, 1H), 13.00 (s, 1H). b) 69 g (0.26 mol) of methyl 1-hydroxy-2-naphthylglyoxylate and 44 g (0.53 mol) of O-methylhydroxylamine hydrochloride in 800 ml of methanol are stirred under reflux for 6 h. The mixture
the residue is taken up in ethyl acetate, and the solution is washed with H2 O, dried over sodium sulfate and concentrated again. 52 g (0.20 mol) of methyl 1-hydroxy-2-naphthylglyoxylate O-methyloxime (77% yield) are obtained. 1 H NMR (CDCl3): δ=4.00 (s, 3H), 4.05 (s, 3H), 7.00 (d, 1H), 7.30 (d, 1H), 7.40-7.90 (m, 4H), 8.35 (m, 1H), 10.90 (s, 1H). c) 5 g (19 mmol) of methyl 1-hydroxy-2-naphthylglyoxylate O-methyloxime, 2.7 g (19 mmol) of 2-fluorobenzyl chloride and 2.6 g (19 mmol) of potassium carbonate in 65 ml of methanol are stirred under reflux for 8 h. The mixture is cooled to room temperature and the solids are removed by filtration. The filtrate is concentrated, and dilute sodium hydroxide solution is added. The mixture is then extracted by shaking seve the combined ether phases are washed with H2 O, dried over sodium sulfate and concentrated. 5 g (13.6 mmol) of methyl 1-(2-fluorobenzyloxy)-2-naphthylglyoxylate O-methyloxime (yield 71%) are obtained (compound no. 2, Table 1). 1 H NMR (CDCl3): δ=3.65 (s, 3H), 4.10 (s, 3H), 5.10 (s, 2H), 7.00-8.20 (m, 10H). The following compounds are prepared in a corresponding manner.
__________________________________________________________________________
##STR9## Comp. no.
mp (°C.) IR (cm-1)
__________________________________________________________________________
resin, , 1061,2
2-FC6 H4CH2
, , 1037,7573
3-FC6 H4CH2
resin, , 1037,7524
4-FC6 H4CH2
resin, , 1037,8215
2,4-F2C6 H3CH2
resin, , 1101,6
2-ClC6 H4CH2
resin, , 1037,7537
3-ClC6 H4CH2
resin, , 1037,7528
4-ClC6 H4CH2
resin, , 1037,8109
2,4-Cl2C6 H3CH2
, , 1098,10
2,6-Cl2C6 H3CH211
3,5-Cl2C6 H3CH212
2,4,6-Cl3C6 H2CH213
2-BrC6 H4CH2
resin, , 1037,75214
3-BrC6 H4CH2
resin, , 1061,103615
4-BrC6 H4CH2
resin, , 1037,80816
2,4-Br2C6 H3CH217
2-J-C6 H4CH2
resin, , 1100,, 75018
2-CH3C6 H4CH2
resin, , 1036,74819
3-CH3C6 H4CH2
resin, , 1037,75220
4-CH3C6 H4CH2
resin, , 1060,103721
2,4-(CH3)2C6 H3CH 222
2,5-(CH3)2C6 H3CH2
resin, , 1100,, 81823
2,4,6-(CH3)3C6 H2CH224
4-t-C4 H9C6 H4CH2
resin, , 1100,, 81725
4-i-C3 H7C6 H4CH226
4-C2 H5C6 H4CH2
resin, , 1061,, 75227
2-CH3 OC6 H4CH228
3-CH3 OC6 H4CH2
resin, , 1227,103729
4-CH3 OC6 H4CH230
4-C2 H5 OC6 H4CH231
4-i-C3 H7 OC6 H4CH232
2-CF3C6 H4CH233
3-CF3C6 H4CH2
resin, , 1126,103734
4-CF3C6 H 4CH235
2-CNC6 H4CH2
81-85, , 1228,36
3-CNC6 H4CH2
resin, , 1229,37
4-CNC6 H4CH2
resin, , 1228,38
2-NO2C6 H4CH239
3-NO2C6 H4CH2
resin, , 1229,40
4-NO2C6 H4CH241
3-C6 H5C6 H4CH242
4-C6 H5C6 H4CH243
4-C6 H5 OC6 H4CH244
2-F, 3-CH3C6 H3CH245
2-Cl, 3-CH3C6 H3CH2
resin, , 1102,, 77246
2-Br, 3-CH3C6 H3CH2
, , 1102,, 77247
2-Cl, 3-i-C3 H 7C6 H3CH2
resin, , 1102,, 75648
2-CH3, 3-i-C3 H7C6 H3CH249
2-CH3, 3-C6 H5C6 H3CH250
2-Cl, 3-C6 H5C6 H3CH251
2-CH3 O, 3-i-C3 H7C6 H3CH252
2,4,5-Cl3C6 H2CH253
2,4,5-(CH3)3C6 H2CH254
2-CH3 O, 5-NO2C6 H3CH255
2,5-Cl2C6 H3CH256
2,5-F2C6 H3CH257
2-Cl, 5-CH3C6 H3CH258
2-F, 3-CH3C6 H3CH259
2,3-F2C6 H3CH260
2,3-Cl2C6 H3CH261
2-F, 3-ClC6 H3CH262
2-F, 4-Br C6 H3CH263
2,6-F2C6 H3CH264
2-F, 6-ClC6 H3CH265
2-Cl, 6-CF3C6 H3CH266
2,3,4,5,6-(CH3)5C6CH267
2,3,4,5,6-F5C6CH268
2-CH3, 4-ClC6 H3CH269
2-Cl, 4-CH3C6 H3CH270
2-CH3 O, 4-CH3C6 H3CH271
4-CH3 O, 2-CH3C6 H3CH272
2-FC6 H4OCH2CH274
3-FC6 H4OCH2CH275
4-FC6 H4OCH2CH276
2-ClC6 H4OCH2CH277
3-ClC6 H4OCH2CH278
4-Cl C6 H4OCH2CH279
2-CH3C6 H4OCH2CH280
3-CH3C6 H4OCH2CH281
4-CH3C6 H4OCH2CH282
2-CH3 OC6 H4OCH2CH283
3-CH3 OC6 H4OCH2CH284
4-CH3 OC6 H4OCH2CH285
4-t-C4 H9C6 H4OCH2CH286
4-C2 H5 OC6 H4OCH2CH287
4-CF3C6 H4OCH2CH288
4-C6 H5C6 H4OCH2CH289
4-(C6 H5CH2O)C6 H4OCH2CH290
2,4,6-Cl3C6 H2OCH2CH291
2,4,6-(CH3)3C6 H2OCH2CH292
1-naphthyl-O
2-naphthyl-O
2-BrC6 H4OCH2CH295
3-BrC6 H4OCH2CH296
4-BrC6 H4OCH2CH297
2-CF3C6 H4OCH2CH298
3-CF3C6 H4OCH2CH299
4-CNC6 H4OCH2CH2100
4-CH3 COC6 H4OCH2CH2101
3-(CH3)2 NC6 H4OCH2CH2102
4-CH3 SC6 H4OCH2CH2103
2-C2 H5 OC6 H4OCH2CH2104
4-t-C4 H9C6 H4OCH2CH2105
2,4-Cl2H6 H3OCH2CH2106
3,4-Cl2C6 H3OCH2CH2107
2,5-Cl2C6 H3OCH2CH2108
2,6-Cl2C6 H3OCH2CH2109
2,4,5-Cl3C6 H2OCH2CH2110
2-Cl, 4-FC6 H3OCH2CH2111
2-Cl, 4-BrC6 H3OCH2CH2112
2,4-(CH3)2C6 H3OCH2CH2113
2-CH3, 4-t-C4 H9C6 H3OCH2CH2114
2-CH3, 4-ClC6 H3OCH2CH2115
2-CH3, 4,6-Cl2C6 H2OCH2CH2116
2,6-(CH3)2C6 H 3OCH2CH2117
2,5,6-(CH3)3C6 H2OCH2CH2118
2,4,5-(CH3)3C6 H2OCH2CH2119
2-i-C3 H7, 5-CH3C6 H3OCH2CH2120
3,5-(C2 H5)2C6 H3OCH2CH2121
2,4,6-(sec-C4 H9)3C6 H2OCH2CH2122
3,5-(CH3 O)2C6 H3OCH2CH2123
2-CH3 O, 4-CH3C6 H3OCH2CH2124
2,6-(CH3)2, 4-CH3 SC6 H2OCH2CH2125
2-Cl, 5-CH3 OC6 H3OCH2CH2126
2-CH3, 4-CH3 SC6 H3OCH2CH2127
2,6-(CH3 O)2C6 H3OCH2CH2128
2-Cl, 4-C6 H5C6 H3OCH2CH2129
2,Cl, 4-CH3C6 H3OCH2CH2130
2-CH3, 6-i-C3 H7C6 H3OCH2CH2131
3-t-C4 H9, 4-CH3 OC6 H3OCH2CH2132
2,4-(CH3)2 -1-naphthyl-OCH2CH2133
4-ClC6 H4SCH2CH2135
2,4,6-Cl3C6 H2OCH2CH(CH3)136
CH2CH(CH3)137
2-FC6 H4O(CH2)3139
3-FC6 H4O(CH2)3140
4-FC6 H4 O(CH2)3141
2-ClC6 H4O(CH2)3142
3-ClC6 H4O(CH2)3143
4-ClC6 H4O(CH2)3144
2-CH3C6 H4O(CH2)3145
3-CH3C6 H4O(CH2)3146
4-CH3C6 H4O(CH2)3147
2-CH3 OC6 H4O(CH2)3148
3-CH3 OC6 H4O(CH2)3149
4-CH3 OC6 H4O(CH2)3150
4-t-C4 H9C6 H4O(CH2)3151
4-C2 H5 OC6 H4O(CH2)3152
4-CF3C6 H4O(CH2)3153
4-C6 H5C6 H4O(CH2)3154
4-(C6 H5CH2O)C6 H4O(CH2)3155
2,4,6-Cl3C6 H2O(CH2)3156
2,4,6-(CH3)3C6 H2O(CH2)3157
1-naphthyl-O
2-naphthyl-O
2,4-Cl2C6 H3O(CH2)3160
3,5-Cl2C6 H3O(CH2)3161
3,4-Cl2C6 H3O(CH2)3162
2,6-(CH3)2C6 H3O(CH2)3163
2,4-(CH3)2C6 H3O(CH3)3164
3-CF3C6 H4O(CH2)3165
2-Cl, 4-CH3C6 H3O(CH2)3166
(CH2) 3167
C6 H5CH2O(CH2)3168
2-FC6 H4O(CH2)4170
3-FC6 H4O(CH2)4171
4-FC6 H4O(CH2)4172
2-CH3C6 H4O(CH2)4173
3-CH3C6 H4O(CH2)4174
4-CH3C6 H4O(CH2)4175
2-CH3 OC6 H4O(CH2)4176
3-CH3 OC6 H4O(CH2)4177
4-CH3 OC6 H4O(CH2)4178
4-t-C4 H9C6 H4O(CH2)4179
4-C2 H5 OC6 H4O(CH2)4180
4-CF3C6 H4O(CH2)4181
4-C6 H5C6 H4O(CH2)4182
4-(C6 H5CH2O)C6 H4(CH2)4183
2,4,6-Cl3C6 H2O(CH2)4184
2,4,6-(CH3)3C6 H2O(CH2)4185
1-naphthyl-O
2-naphthyl-O
3-CF3C6 H4O(CH2)4188
3-iso-C3 H7C6 H4O(CH2)4189
4-iso-C3 H7C6 H4O(CH2)4190
3-t-C4 H9C6 H4O(CH2)4191
4-t-C4 H9C6 H4O(CH2)4192
3-C6 H5C6 H4O(CH2)4193
2,4-Cl2C6 H3O(CH2)4194
3,4-Cl2C6 H3O(CH2)4195
3,5-Cl2C6 H3O(CH2)4196
2,6-Cl2C6 H3O(CH2)4197
2-Cl, 4-CH3C6 H3O(CH2)4198
2,6-(CH3)2C6 H3O(CH2)4199
2,5-(CH3)2C6 H3O(CH2)4200
4-CNC6 H4O(CH2)4201
C6 H5CH2O(CH2)4203
CH2CHCHCH2204
2-FC6 H4OCH2CHCHCH2205
3-FC6 H4OCH2CHCHCH2206
4-FC6 H4OCH2CHCHCH2207
2-ClC6 H4OCH2CHCHCH2208
3-ClC6 H4OCH2CHCHCH2209
4-ClC6 H4OCH2CHCHCH2210
2-ClC6 H4O(CH2)5212
3-ClC6 H4O(CH2)5213
4-ClC6 H4O(CH2)5214
2-FC6 H4O(CH2)5215
3-FC6 H4O(CH2)5216
4-FC6 H4O(CH2)5217
2-CH3C6 H4O(CH2)5218
3-CH3C6 H4O(CH2)5219
4-CH3C6 H4O(CH2)5220
2-CH3 OC6 H4O(CH2)5221
3-CH3 OC6 H4O(CH2)5222
4-CH3 OC6 H4O(CH2)5223
4-t-C4 H9C6 H4O(CH2)5224
4-C2 H5 OC6 H4O(CH2)5225
4-CF3C6 H4O(CH2)5226
4-C6 H5C6 H4O(CH2)5227
4-(C6 H5CH2O)C6 H4O(CH2)5228
2,4,6-Cl3C6 H2O(CH2)5229
2,4,6-(CH3)3C6 H2O(CH2)5230
1-naphthyl-O
2-naphthyl-O
C6 H5CH2O(CH2) 5233
2-ClC6 H4O(CH2)6235
3-ClC6 H4O(CH2)6236
4-ClC6 H4O(CH2)6237
2-FC6 H4O(CH2)6238
3-FC6 H4O(CH2)6239
4-FC6 H4O(CH2)6240
2-CH3C6 H4O(CH2)6241
3-CH3C6 H4O(CH2)6242
4-CH3C6 H4O(CH2)6243
2-CH3 OC6 H4O(CH2)6244
3-CH3 OC6 H4O(CH2)6245
4-CH3 OC6 H4O(CH2)6246
4-t-C4 H9C6 H 4O(CH2)6247
4-C2 H5 OC6 H4O(CH2)6248
4-CF3C6 H4O(CH2)6249
4-C6 H5C6 H4O(CH2)6250
4-(C6 H5CH2O)C6 H4O(CH2)6251
2,4,6-Cl3C6 H2O(CH2)6252
2,4,6-(CH3)3C6 H2O(CH2)6253
1-naphthyl-O
2-naphthyl-O
C6 H5CH2O(CH2)6256
2-ClC6 H4O(CH2)7258
3-ClC6 H4O(CH2)7259
4-ClC6 H4O(CH2)7260
2-FC 6 H4O(CH2)7261
3-FC6 H4O(CH2)7262
4-FC6 H4O(CH2)7263
2-CH3C6 H4O(CH2)7264
3-CH3C6 H4O(CH2)7265
4-CH3C6 H4O(CH2)7266
2-CH3 OC6 H4O(CH2)7267
3-CH3 OC6 H4O(CH2)7268
4-CH3 OC6 H4O(CH2)7269
4-t-C4 H9C6 H4O(CH2)7270
4-C2 H5 OC6 H4O(CH2)7271
4-CF3C6 H4O(CH2)7272
4-C6 H5C6 H4O(CH2)7273
2,4,6-(Cl3)3C6 H2O(CH2)7274
2,4,6-(CH3)3C6 H2O(CH2)7275
1-naphthyl-O
2-naphthyl-O
4-(C6 H5CH2O)C6 H4O(CH2)7278
C6 H5CH2O(CH2)7279
2-ClC6 H4O(CH2)8281
3-ClC6 H4O(CH2)8282
4-ClC6 H4O(CH2)8283
2-FC6 H4O(CH2)8284
3-FC6 H4O(CH2)8285
4-FC6 H4O(CH2)8286
2-CH3C6 H4O(CH2)8287
3-CH3 C6 H4O(CH2)8288
4-CH3C6 H4O(CH2)8289
2-CH3 OC6 H4O(CH2)8290
3-CH3 OC6 H4O(CH2)8291
4-CH3 OC6 H4O(CH2)8292
4-t-C4 H9C6 H4O(CH2)8293
4-C2 H5 OC6 H4O(CH2)8294
4-CF3C6 H4O(CH2)8295
4-C6 H5C6 H4O(CH2)8296
4-(C6 H5CH2O)C6 H4O(CH2)8297
2,4,6-Cl3C6 H2O(CH2)8298
2,4,6-(CH3)3C6 H2O(CH2)8299
1-naphthyl-O
(CH2 )8300
2-naphthyl-O
C6 H5CH2O(CH2)8302
(CH2)10304
2-ClC6 H4O(CH2)10305
3-ClC6 H4O(CH2)10306
4-ClC6 H4O(CH2)10307
2-FC6 H4O(CH2)10308
3-FC6 H4O(CH2)10309
4-FC6 H4O(CH2)10310
2-CH3C6 H4O(CH2)10311
3-CH3C6 H4O(CH2)10312
4-CH3C6 H4O(CH2)10313
2-CH3 OC6 H4O(CH2)10314
3-CH 3 OC6 H4O(CH2)10315
4-CH3 OC6 H4O(CH2)10316
4-t-C4 H9C6 H4O(CH2)10317
4-C2 H5 OC6 H4O(CH2)10318
4-CF3C6 H4O(CH2)10319
4-C6 H5C6 H4O(CH2)10320
4-(C6 H5CH2O)C6 H4O(CH2)10321
2,4,6-Cl3C6 H2O(CH2)10322
2,4,6-(CH3)3C6 H2O(CH2)10323
1-naphthyl-O
(CH2)10324
2-naphthyl-O
(CH2)10325
C6 H5CH2O(CH2)10326
3,4-Cl2C6 H3CH2
resin, , 1228,, 819327
3-C6 H5 OC6 H4CH2328
4-C12H25C6 H4CH2329
2-Cl, 6-CNC6 H3CH2330
3,4-(CH3)2C6 H3CH2331
2-CH3, 4-t-C4 H9C6 H3CH2332
2-Cl, 4-CH3 OC6 H3CH2333
2,3,6-Cl3C6 H2CH2
__________________________________________________________________________
__________________________________________________________________________
##STR10## Comp. no. R
mp(°C.) IR(cm-1)
__________________________________________________________________________
2-FC6 H4CH23a
3-FC6 H4CH24a
4-FC6 H4CH25a
2,4-F2C6 H3CH26a
2-ClC6 H4CH27a
3-ClC6 H4CH28a
4-ClC6 H4CH29a
2,4-Cl2C6 H3CH210a
2,6-Cl2C6 H3CH211a
3,5-Cl2C6 H3CH212a
2,4,6-Cl3C6 H2CH213a
2-BrC6 H4CH214a
3-BrC6 H4CH215a
4-BrC6 H4CH216a
2,4-Br2C6 H3CH217a
2-JC6 H4CH218a
2-CH3C6 H4CH219a
3-CH3C6 H4CH220a
4-CH3C6 H4CH221a
2,4-(CH3)2C6 H3CH222a
2,5-(CH3)2C6 H3CH223a
2,4,6-(CH3)3C6 H2CH224a
4-t-C4 H9C6 H4CH225a
4-i-C3 H7C6 H4CH226a
4-C2 H5C6 H4CH227a
2-CH3 OC6 H4CH228a
3-CH3 OC6 H4CH229a
4-CH3 OC6 H4CH230a
4-C2 H5 OC6 H4CH231a
4-i-C3 H7 OC6 H4CH232a
2-CF3C6 H4CH233a
3-CF3C6 H4CH234a
4-CF3C6 H4CH235a
2-CNC6 H4CH236a
3-CNC6 H4CH237a
4-CNC6 H4CH238a
2-NO2C6 H4CH239a
3-NO2C6 H4CH240a
4-NO2C6 H4CH241a
3-C6 H5C6 H4CH242a
4-C6 H5C6 H4CH243a
4-C6 H5 OC6 H4CH244a
2-F,3-CH3C6 H3CH245a
2-Cl,3-CH3C6 H3CH246a
2-Br,3-CH3C6 H3CH247a
2-Cl,3-i-C3 H7C6 H3CH248a
2-CH3,3-i-C3 H7C6 H3CH249a
2-CH3,3-C6 H5C6 H3CH250a
2-Cl,3-C6 H5C6 H3CH251a
2-CH3 O,3-i-C3 H7C6 H3CH252a
2,4,5-Cl3C6 H2CH253a
2,4,5-(CH3)3C6 H2CH254a
2-CH3 O,5-NO2C6 H3CH255a
2,5-Cl2C6 H3CH256a
2,5-F2C6 H3CH257a
2-Cl,5-CH3C6 H3CH258a
2-F,3-CH3C6 H3CH259a
2,3-F2C6 H3CH260a
2,3-Cl2C6 H3CH261a
2-F,3-ClC6 H3CH262a
2-F,4-BrC6 H3CH263a
2,6-F2C6 H3CH264a
2-F,6-ClC6 H3CH265a
2-Cl,6-CF3C6 H3CH266a
2,3,4,5,6-(CH3)5C6CH267a
2,3,4,5,6-F5C6CH268a
2-CH3,4-ClC6 H3CH269a
2-Cl,4-CH3C6 H3CH270a
2-CH3 O,4-CH3C6 H3CH271a
4-CH3 O,2-CH3C6 H3CH272a
C6 H5O CH2CH273a
2-FC6 H4OCH2CH274a
3-FC6 H4OCH2CH275a
4-FC6 H4OCH2CH276a
2-ClC6 H4OCH2CH277a
3-ClC6 H4OCH2CH278a
4-ClC6 H4OCH2CH279a
2-CH3C6 H4OCH2CH280a
3-CH3C6 H4OCH2CH281a
4-CH3 C6 H4OCH2CH282a
2-CH3 OC6 H4OCH2CH283a
3-CH3 OC6 H4OCH2CH284a
4-CH3 OC6 H4OCH2CH285a
4-t-C4 H9C6 H4OCH2CH286a
4-C2 H5 OC6 H4OCH2CH287a
4-CF3C6 H4OCH2CH288a
4-C6 H5C6 H4OCH2CH289a
4-(C6 H5CH2O)C6 H4OCH2CH290a
2,4,6-Cl3C6 H2OCH2CH291a
2,4,6-(CH3)3C6 H2OCH2CH292a
1-naphthyl-O
2-naphthyl-O
2-BrC6 H4OCH2CH295a
3-BrC6 H4OCH2CH296a
4-BrC6 H4OCH2CH297a
2-CF3C6 H4OCH2CH298a
3-CF3C6 H4OCH2CH299a
4-CNC6 H4OCH2CH2100a
4-CH3 COC6 H4OCH2CH2101a
3-(CH3)2 NC6 H4OCH2CH2102a
4-CH3 SC6 H4OCH2CH2103a
2-C2 H5 OC6 H4OCH2CH2104a
4-t-C4 H9C6 H4OCH2CH2105a
2,4-Cl2H6 H3OCH2CH2106a
3,4-Cl2C6 H3OCH2CH2107a
2,5-Cl2C6 H3OCH2CH2108a
2,6-Cl2C6 H3OCH2CH2109a
2,4,5-Cl3C6 H2OCH2CH2110a
2-Cl,4-FC6 H3OCH2CH2111a
2-Cl,4-BrC6 H3OCH2CH2112a
2,4-(CH3)2C6 H3OCH2CH2113a
2-CH3,4-t-C4 H9C6 H3OCH2CH2114a
2-CH3,4-ClC6 H3OCH2CH2115a
2-CH3,4,6-Cl2C6 H2OCH2CH2116a
2,6-(CH3)2C6 H3OCH2CH2117a
2,5,6-(CH3)3C6 H2OCH2CH2118a
2,4,5-(CH3)3C6 H2OCH2CH2119a
2-i-C3 H7,5-CH3 C6 H3OCH2CH2120a
3,5-(C2 H5)2C6 H3OCH2CH2121a
2,4,6-(sec-C4 H9)3C6 H2OCH2CH2122a
3,5-(CH3 O)2C6 H3OCH2CH2123a
2-CH3 O,4-CH3C6 H3OCH2CH2124a
2,6-(CH3)2,4-CH3 SC6 H2OCH2CH2125a
2-Cl,5-CH3 OC6 H3OCH2CH2126a
2-CH3,4-CH3 SC6 H3OCH2CH2127a
2,6-(CH3 O)2C6 H3OCH2CH2128a
2-Cl,4-C6 H5C6 H3OCH2CH2129a
2-Cl,4-CH3C6 H3OCH2CH2130a
2-CH3,6-i-C3 H7C6 H3OCH2CH2131a
3-t-C4 H9,4-CH3 OC6 H3OCH2CH2132a
2,4-(CH3)2 -1-naphthyl-OCH2CH2133a
C6 H5S CH2CH2134a
4-ClC6 H4SCH2CH2135a
2,4,6-Cl3C6 H2OCH2CH(CH3)136a
C6 H5O CH2CH(CH3)137a
C6 H5O (CH2)3138a
2-FC6 H4O(CH2)3139a
3-FC6 H4O(CH2)3140a
4-FC6 H4O(CH2)3141a
2-ClC6 H4O(CH2)3142a
3-ClC6 H4O(CH2)3143a
4-ClC6 H4O(CH2)3144a
2-CH3C6 H4O(CH2)3145a
3-CH3C6 H4O(CH2)3146a
4-CH3C6 H4O(CH2)3147a
2-CH3 OC6 H4O(CH2)3148a
3-CH3 OC6 H4O(CH2)3149a
4-CH3 OC6 H4O(CH2)3150a
4-t-C4 H9C6 H4O(CH2)3151a
4-C2 H5 OC6 H4O(CH2)3152a
4-CF3C6 H4O(CH2)3153a
4-C6 H5C6 H4O(CH2)3154a
4-(C6 H5CH2O)C6 H4O(CH2)3155a
2,4,6-Cl3C6 H2O(CH2)3156a
2,4,6-(CH3)3C6 H2O(CH2 )3157a
1-naphthyl-O
(CH2)3158a
2-naphthyl-O
(CH2)3159a
2,4-Cl2C6 H3O(CH2)3160a
3,5-Cl2C6 H3O(CH2)3161a
3,4-Cl2C6 H3O(CH2)3162a
2,6-(CH3)2C6 H3O(CH2)3163a
2,4-(CH3)2C6 H3O(CH2)3164a
3-CF3C6 H4O(CH2)3165a
2-Cl,4-CH3C6 H3O(CH2)3166a
C6 H5S (CH2)3167a
C6 H5CH2O(CH2)3168a
C6 H5O (CH2)4169a
2-FC6 H4O(CH2)4170a
3-FC6 H4O(CH2)4171a
4-F C6 H4O(CH2)4172a
2-CH3C6 H4O(CH2)4173a
3-CH3C6 H4O(CH2)4174a
4-CH3C6 H4O(CH2)4175a
2-CH3 OC6 H4O(CH2)4176a
3-CH3 OC6 H4O(CH2)4177a
4-CH3 OC6 H4O(CH2)4178a
4-t-C4 H9C6 H4O(CH2)4179a
4-C2 H5 OC6 H4O(CH2)4180a
4-CF3C6 H4O(CH2)4181a
4-C6 H5C6 H4O(CH2)4182a
4-(C6 H5CH2O)C6 H4(CH2)4183a
2,4,6-Cl3C6 H2O(CH2)4184a
2,4,6-(CH3)3C6 H2O(CH2)4185a
1-naphthyl-O
(CH2)4186a
2-naphthyl-O
(CH2)4187a
3-CF3C6 H4O(CH2)4188a
3-iso-C3 H7C6 H4O(CH2)4189a
4-iso-C3 H7C6 H4O(CH2)4190a
4-t-C4 H9C6 H4O(CH2)4191a
4-t-C4 H9C6 H4O(CH2)4192a
3-C6 H5C6 H4O(CH2)4193a
2,4-Cl2C6 H3O(CH2)4194a
3,4-Cl2C6 H3O(CH2)4195a
3,5-Cl2C6 H3O(CH2)4196a
2,6-Cl2C6 H3O(CH2)4197a
2-Cl,4-CH3C6 H3O(CH2)4198a
2,6-(CH3)2C6 H3O(CH2)4199a
2,5-(CH3)2C6 H3O(CH2)4200a
4-CNC6 H4O(CH2)4201a
C6 H5S (CH2)4202a
C6 H5CH2O(CH2)4203a
C6 H5O CH2CHCHCH2204a
2-FC6 H4OCH2CHCHCH2205a
3-FC6 H4OCH2CHCHCH2206a
4-FC6 H4OCH2CHCHCH2207a
2-ClC6 H4OCH2CHCHCH2208a
3-ClC6 H4OCH2CHCHCH2209a
4-ClC6 H4OCH2CHCH CH2210a
C6 H5O (CH2)5211a
2-ClC6 H4O(CH2)5212a
3-ClC6 H4O(CH2)5213a
4-ClC6 H4O(CH2)5214a
2-FC6 H4O(CH2)5215a
3-FC6 H4O(CH2)5216a
4-FC6 H4O(CH2)5217a
2-CH3C6 H4O(CH2)5218a
3-CH3C6 H4O(CH2)5219a
4-CH3C6 H4O(CH2)5220a
2-CH3 OC6 H4O(CH2)5221a
3-CH3 OC6 H4O(CH2)5222a
4-CH3 OC6 H4O(CH2)5223a
4-t-C4 H9C6 H4O(CH2)5224a
4-C2 H5 OC6 H4O(CH2)5225a
4-CF3C6 H4O(CH2)5226a
4-C6 H5C6 H4O(CH2)5227a
4-(C6 H5CH2O)C6 H4O(CH2)5228a
2,4,6-Cl3C6 H2O(CH2)5229a
2,4,6-(CH3)3C6 H2O(CH2)5230a
1-naphthyl-O
(CH2)5231a
2-naphthyl-O
(CH2)5232a
C6 H5CH2O(CH2)5233a
C6 H5O (CH2)6234a
2-ClC6 H4O(CH2)6235a
3-ClC6 H4O(CH2)6236a
4-ClC6 H4O(CH2)6237a
2-FC6 H4O(CH2)6238a
3-FC6 H4O(CH2)6239a
4-FC6 H4O(CH2)6240a
2-CH3C6 H4O(CH2)6241a
3-CH3C6 H4O(CH2)6242a
4-CH3C6 H4O(CH2)6243a
2-CH3 OC6 H4O(CH2)6244a
3-CH3 OC6 H4O(CH2)6245a
4-CH3 OC6 H4O(CH2)6246a
4-t-C4 H9C6 H4O(CH2)6247a
4-C2 H5 OC6 H4O(CH2)6248a
4-CF3C6 H4O(CH2)6249a
4-C6 H5C6 H4O(CH2) 6250a
4-(C6 H5CH2O)C6 H4O(CH2)6251a
2,4,6-Cl3C6 H2O(CH2)6252a
2,4,6-(CH3)3C6 H2O(CH2)6253a
1-naphthyl-O
(CH2)6254a
2-naphthyl-O
(CH2)6255a
C6 H5CH2O(CH2)6256a
C6 H5O (CH2)7257a
2-ClC6 H4O(CH2)7258a
3-ClC6 H4O(CH2)7259a
4-ClC6 H4O(CH2)7260a
2-FC6 H4O(CH2)7261a
3-FC6 H4O(CH2)7262a
4-FC6 H4O(CH2)7263a
2-CH3C6 H4O(CH2)7264a
3-CH3C6 H4O(CH2)7265a
4-CH3C6 H4O(CH2)7266a
2-CH3 OC6 H4O(CH2)7267a
3-CH3 OC6 H4O(CH2)7268a
4-CH3 OC6 H4O(CH2)7269a
4-t-C4 H9C6 H4O(CH2)7270a
4-C2 H5 OC6 H4O(CH2)7271a
4-CF3C6 H4O(CH2)7272a
4-C6 H5C6 H4O(CH2)7273a
2,4,6-(Cl3)3C6 H2O(CH2)7274a
2,4,6-(CH3)C6 H2O(CH2)7275a
1-naphthyl-O
(CH2)7276a
2-naphthyl-O
(CH2)7277a
4-(C6 H5 CH2O)C6 H4O(CH2)7278a
C6 H5CH2O(CH2)7279a
C6 H5O (CH2)8280a
2-ClC6 H4O(CH2)8281a
3-ClC6 H4O(CH2)8282a
4-ClC6 H4O(CH2)8283a
2-FC6 H4O(CH2)8284a
3-FC6 H4O(CH2)8285a
4-FC6 H4O(CH2)8286a
2-CH3C6 H4O(CH2)8287a
3-CH3C6 H4O(CH2)8288a
4-CH3C6 H4O(CH2)8289a
2-CH3 OC6 H4O(CH2)8290a
3-CH3 OC6 H4O(CH2 )8291a
4-CH3 OC6 H4O(CH2)8292a
4-t-C4 H9C6 H4O(CH2)8293a
4-C2 H5 OC6 H4O(CH2)8294a
4-CF3C6 H4O(CH2)8295a
4-C6 H5C6 H4O(CH2)8296a
4-(C6 H5CH2O)C6 H4O(CH2)8297a
2,4,6-Cl3C6 H2O(CH2)8298a
2,4,6-(CH3)3C6 H2O(CH2)8299a
1-naphthyl-O
(CH2)8300a
2-naphthyl-O
(CH2)8301a
C6 H5CH2O(CH2)8302a
C6 H5O (CH2)9303a
C6 H5O (CH2)10304a
2-ClC 6 H4O(CH2)10305a
3-ClC6 H4O(CH2)10306a
4-ClC6 H4O(CH2)10307a
2-FC6 H4O(CH2)10308a
3-FC6 H4O(CH2)10309a
4-FC6 H4O(CH2)10310a
2-CH3C6 H4O(CH2)10311a
3-CH3C6 H4O(CH2)10312a
4-CH3C6 H4O(CH2)10313a
2-CH3 OC6 H4O(CH2)10314a
3-CH3 OC6 H4O(CH2)10315a
4-CH3 OC6 H4O(CH2)10316a
4-t-C4 H9C6 H4O(CH2)10317a
4-C2 H5 OC6 H 4O(CH2)10318a
4-CF3C6 H4O(CH2)10319a
4-C6 H5C6 H4O(CH2)10320a
4-(C6 H5CH2O)C6 H4O(CH2)10321a
2,4,6-Cl3C6 H2O(CH2)10322a
2,4,6-(CH3)3C6 H2O(CH2)10323a
1-naphthyl-O
(CH2)10324a
2-naphthyl-O
(CH2)10325a
C6 H5CH2O(CH2)10
__________________________________________________________________________
Generally speaking, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the Ascomycetes and Basidiomycetes classes. Some of them have a systemic action and can be used as foliar and soil fungicides. The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits. The novel compounds are particularly useful for controlling the following plant diseases:
Erysiphe graminis in cereals,
Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,
Podosphaera leucotricha in apples,
Uncinula necator in vines,
Puccinia species in cereals,
Rhizoctonia species in cotton and lawns,
Ustilago species in cereals and sugar cane,
Venturia inaequalis (scab) in apples,
Helminthosporium species in cereals,
Septoria nodorum in wheat,
Botrytis cinerea (gray mold) in strawberries and grapes,
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 various plants,
Plasmopara viticola in grapes,
Alternaria species in fruit and vegetables. The compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi. The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for whi they should at all events ensure a fine and uniform distribution of the active ingredient. The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsif if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as lignin, sulfite waste liquors and methylcellulose. The fungicidal agents generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials, for example against Paecilomyces variotii. The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering. Examples of formulations are given below. I. 90 parts by weight of compound no. 2 is mixed with 10 parts by weight of N-methyl-α-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops. II. 20 parts by weight of compound no. 3 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained. III. 20 parts by weight of compound no. 4 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and finely distributing it therein, an aqueous dispersion is obtained. IV. 20 parts by weight of compound no. 6 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained. V. 80 parts by weight of compound no. 13 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in water, a spray liquor is obtained. VI. 3 parts by weight of compound no. 19 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient. VII. 30 parts by weight of compound no. 2 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence. VIII. 40 parts by weight of compound no. 3 is intimately mixed with 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water to give a stable aqueous dispersion. Dilution in water gives an aqueous dispersion. IX. 20 parts by weight of compound no. 4 is intimately mixed with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained. In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in an increase in the fungicidal spectrum. USE EXAMPLES For comparison purposes, methyl 2-benzyloxyphenylglyoxylate O-methyloxime (A) disclosed in EP 253,213 was used. USE EXAMPLE 1 Action on Botrytis Cinerea in Pimientos Pimiento seedlings of the "Neusiedler Ideal Elite" variety with 4 to 5 well developed leaves were sprayed to runoff with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the plants were sprayed with a conidial suspension of the fungus Botrytis cinerea and kept in a high-humidity chamber at 22° to 24° C. After 5 days, the disease had spread on the untreated control plants to such an extent that the necroses covered the major portion of the leaves. The results show that active ingredients 6 and 13, applied as 0.05 wt % spray liquors, have a better fungicidal action (90%) than prior art active ingredient A (65%). USE EXAMPLE 2 Action on Pyrenophora Teres Barley seedlings of the "Igri" variety were sprayed to runoff at the two-leaf stage with aqueous suspensions consisting (dry basis) of 80% of active ingredient and 20% of emulsifier. After 24 hours the plants were inoculated with a spore suspension of the fungus Pyrenophora teres, and set up for 48 hours in a high-humidity climatic cabinet at 18° C. The plants were then cultivated for a further 5 days in the greenhouse at 20° to 22° C. and a relative humidity of 70° C. The extent of fungus spread was then assessed. The results show that active ingredients 2, 3, 4, 6, 13 and 19, applied as 0.05 wt % spray liquors, have a better fungicidal action (90%) than prior art active ingredient A (60%).
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