NZ236824A

NZ236824A - Unsaturated cyclohexylacetic acid derivatives and insecticidal and fungicidal compositions

Info

Publication number: NZ236824A
Application number: NZ236824A
Authority: NZ
Inventors: Bernd Mueller; Hubert Sauter; Eberhard Ammermann; Gisela Lorenz
Original assignee: Basf Ag
Priority date: 1990-01-20
Filing date: 1991-01-18
Publication date: 1992-05-26
Also published as: CA2034156A1; IL96896A; CS11391A2; DE4001618A1; ES2062278T3; AU6947691A; ATE102922T1; JPH054961A; DE59005018D1; HUT56817A; HU910176D0; AU629088B2; EP0438726B1; EP0438726A1; DK0438726T3; KR910014346A; IL96896A0; ZA91371B; HU208310B

Abstract

Unsaturated cyclohexylacetic acid derivatives of the formula I <IMAGE> in which U is =NOCH3, =CHOCH3, =CH2, =CH-CH3, =CH-CH2-CH3, =N-NH-CH3 or =CH-S-CH3, n denotes the numbers 0 to 10, A denotes hydrogen or the optionally substituted radicals alkyl, cycloalkyl, aryl or hetaryl, and, if n = 0, X is a single bond or oxygen or sulphur, and the phytophysiologically acceptable acid addition products and base addition products thereof, and the fungicides and insecticides containing these compounds.

Description

<div class="application article clearfix" id="description"> New Zealand Paient Spedficaiion for Paient Number £36824 2 3 6 8 2 4 i CoriV?'"*!! "'licGtlors Filsd: %.? ;'.ss: :^}cca?;.3^3./ui.,,co.^.^!3.^2,rL= 2-I •CO.71 OZtrAS.f .'.2~flu7.C.COD.2.3<^..[2.U.,.3Uci , .C.O..1Q2Jf-.I./.',2,f Ji^...CCC7l0.^?.3>.3./.-'-W, Pubifcstio-ri P,*; P.O. vJO'.i: 3VC. C?.. Class Cont: t*.cr-:"n.C>.'2-.C-. i^/oS^O j j cpnDa^3.2,pi+r c.o^d^-Tt.7^0,'3^-, ir\5.i4-3/io.,.^0^.?ki.to tn.u,7r &v.8<>, Patents Form No, Class Cont: /-ftO iM.-2p | GCoy /VCjtJ j r~XLtr,. /\.Qi tO.^iTl / 0^2-.roC=)v',Q-. NEW ZE. » = fH ? 2 « Si d £ s^-C / f « "i f # jAi-S Hi ••'J, PATENTS ACT 1953 COMPLETE SPECIFICATION UNSATURATED CYCLOHEXYLACETIC ACID DERIVATIVES, AND CROP-PROTECTION' AGENTS CONTAINING SAME ' ? o\ >£Jan'»M K>S t" / v ?- WE, BASF AKTIENGESELLSCHAFT, a German Joint Company organised and existing under the laws of the Federal Republic of Germany, of 6700 Ludwigshafen Federal Republic of Germany hereby declare the invention, for which We pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: - 1 - (followed by page la) £00 O.Z. 0050/41358 Unsaturated cvclohexvlacetic acid derivativesf and crop-protection agents containing samp The present invention relates to cyclohexylacetic acid derivatives having a fungicidal and insecticidal action, to fungicides and insecticides containing these compounds, and to a method of combating fungi. We have found that unsaturated cyclohexylacetic acid derivatives of the formula I where U is =N0CH3, =CH0CH3/ =CH2, =CH-CH3, =CH-CH2-CH3, =N-NH-CH3 or =CH-S-CH3, n is from 0 to 10, A is hydrogen or substituted or unsubstituted alkyl, cycloalkyl, aryl or hetaryl, and X is a single bond in the case where n = 0, and oxygen, sulfur or a single bond in the case where n is not 0, and the plant-compatible acid-addition products and base-addition products thereof have a high fungitoxic and insecticidal action and very good plant compatibility. Examples of acids for acid-addition products are mineral acids, eg. hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid or nitric acid, or car-boxylic acids, such as formic acid, acetic acid, oxalic acid, malonic acid, lactic acid, malic acid, succinic acid, tartaric acid, citric acid or salicylic acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid, or proton-acidic compounds in general, eg. saccharin. Examples of bases for base-addition products are potassium hydroxide, potassium carbonate, sodium hydroxide, sodium carbonate and ammonium hydroxide. The novel compounds of the formula I may be produced as mixtures of stereoisomers (E/Z isomers, diastereomers or enantiomers), which can be resolved into the individual components in a conventional manner, for I .(followed by page 2) - 2 - ? 5c 82 4 O.Z. 0050/41358 example by crystallization or chromatography. The individual isomers and their mixtures can be used as fungicides or insecticides and are included in the invention. If U can occur in sym/anti-isomers, the invention 5 relates to all the isomers, in particular the anti- isomers. In particular, the invention relates to all the diastereomers, in particular those having a bis-equatorial arrangement at the two centers of chirality in 10 the cyclohexane ring. U is =N0CH3, =CHOCH3, =CH2, =CH-CH3, =CH-CH2-CH3, =N-NH-CH3 or =CH-S-CH3, in particular =N0CH3, =CH-0CH3 or =CH-CH3, preferably =N0CH3. n is from 0 to 10, in particular from 0 to 5, 15 preferably 0, 1, 2 or 3. A is, for example, a saturated or unsaturated, straight-chain or branched hydrocarbon radical having from 1 to S, in particular from 1 to 4, carbon atoms or a C3-C8-cycloalkyl radical, or phenyl, thienyl, furyl, 20 pyrryl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl, indolyl, benzimidazolyl, quin-azolyl, or quinoxalyl, the cycloalkyls, alkyls, aryls or hetaryls mentioned being unsubstituted or substituted by 25 from 1 to 3 identical or different substituents from the group comprising halogen, eg. fluorine, chlorine, bromine or iodine, Cj.-Ca-alkyl, Cj.-Cg-alkylthio, C1-C3-alkyl-sulfinyl, cyano, hydroxyl, nitro, C^-Cg-alkoximino, C1-C9-alkoxy, phenyl, C^-C^-haloalkyl, Ci-Cg-alkenyloximino, 30 formyl, C^-Cg-alkylcarbonyl or (^-Cg-alkoxycarbonyl, or phenyl which is substituted by from 1 to 3 identical or different substituents from the group comprising halogen, eg. fluorine, chlorine, bromine or iodine, Cj.-Cg-alkyl, C1-C8-alkylthio, C^-Cg-alkylsulfinyl, cyano, hydroxyl, 35 nitro, Ci-Ca-alkoximino, Ci-Cg-alkoxy, phenyl, C^-C^-halo- alkyl, Ci-Cg-alkenyloximino, formyl or Ci-Cg-alkylcarbonyl. A is preferably a saturated or unsaturated, ,r^\ ► n r> - 3 - ? 3 6 8 2 O.Z. 0050/41358 straight-chain or branched hydrocarbon radical having from 1 to 6, in particular from 1 to 4, carbon atoms or a C3-Cs-cycloalkyl radical, or phenyl, pyridyl or benz-imidazolyl. The novel compounds can be prepared, for example, by the following processes: Methyl a-cyclohexen-l-yl-a-oxoacetate 1 (G. Neef et al./ THL 1977 (32), 2 825-8)/isa"r^cte^wit^^aSt\iiol 2, if necessary with base catalysis, to give a thioether 3 (Y. Vankar et al., J. Chem. Research 1989, 178-179) (scheme 1). Scheme 1 + A—X— (CH 2) n—SH A-X-(CH2)n^S^Y^ O^^C02CH3 H 3C02C-^0 I 2 3 A and n are as above. Substituted methyl a-oxoacetates 3 are converted into the active ingredients 4 by reaction with CH3-0-NH3Cl or H2N-NH-CH3 (scheme 2) . Scheme 2 A-X-(CH2)n^S>^Y^ A_X-(CH2) H3C02C-^0 H3CO2C-^<5U 3 4 U is =N0CH3 or =N-NHCH3, and A and n are as above. The methyl a-octoacetates 3 can be used to prepare the compounds 5 by a Wittig reaction with (C6H5) jP^-CHjX , (C8H5)3P+-CH2-CH3X~, (C6H5)3P+-CH2-CH2-CH3X" (X = halogen) or (C6Hs)3P+-CH2-0-CH3Cl", (C6Hs)2P(=0)-CH2-0-CH3 or by Peterson olefin formation using (CH3)3Si-CH2-0-CH3 (scheme 3) . Scheme 3 A-X-(CH2)n^S>\^ ► A-X-(CH2)n^S^Y^ H3C02C-"^0 h 3co 3 . 5 9*a ; ft ^ -2 APR 092*1 C "2 m * \ % er t 2 3 8 8 - 4 - O.Z. 0050/41358 U is =CH2/ =CH-CH3, =CH-CH2-CH3 or =CHOCH3, and A and n are as above. The thioenol ethers 7 can be obtained from the enol ethers 6 by reaction with methyl mercaptan (EP 178 826; scheme 4). Scheme 4 A-X-(CH2)n^S-"'\^ ► A-X-(CH2)n^S--'^^J h3co2c^choch3 h3co2c^chsch3 6 . 7 A and n are as above. The Examples below illustrate the preparation of novel compounds. EXAMPLE 1 Methyl a-(2-benzylthiocyclohexyl)-a-oxoacetate (Compound No. 1.15) 2 g (12 mmol) of methyl a-cyclohexenyl-a-oxo-acetate, 1.5 g (12 mmol) of benzyl mercaptan and 1 g (10 mmol) of triethylamine in 10 ml of methylene chloride are stirred at room temperature (20°C) for 15 hours. After the stirring period, water is added to the batch, and the aqueous phase is extracted with methylene chloride. The organic phase is extracted with water, dried over MgS04 and evaporated. Chromatographic purification of the crude product gives 2.3 g (66 %) of the title compound as a pale yellow oil. IR (cm-1): 2933, 1727, 1277, 1069. EXAMPLE 2 Methyl a-(2-benzylthiocyclohexyl)-a-oxoacetate 0-methyl oxime (Compound No. 2.15) 2.3 g (7.9 mmol) of methyl a-(2-benzylthiocyclo-hexyl)-a-oxoacetate (Example 1) and 0.66 g (8 mmol) of methoxyamine hydrochloride in 15 ml of methanol are stirred at room temperature for 15 hours. 236824 - 5 - O.Z. 0050/41358 Water is added to the reaction mixture, and the aqueous phase is extracted with ether. The organic phase is washed with water, dried over MgS04 and evaporated. Chromatographic purification of the crude product gives 5 1 g (40 %) of the title compound as a pale yellow oil. IR (cm"1): 2935, 1726,1151, 1042. _ 2 3 0 8 2 A- o 890828 O.Z. 0050/41358 Table 1 No. A-X-(CH2)n~sS H3C02C A-X-(CH2)n mp. IR: v(cm-1) 5 1. 1 1. 2 1. 1. 1. 10 1. 1. 3 4 5 6 7 1. 8 1. 9 1.10 15 1.11 1.12 1.13 1.14 1.15 20 1.16 1.17 1.18 1.19 1.20 25 1.21 1.22 1.23 1.24 1.25 30 1.26 1.27 1.28 1.29 1.30 35 1.31 1.32 1.33 1.34 1.35 40 H methyl ethyl isopropy1 butyl sec.-buty1 t-buty1 isobutyl penty1 pivaloy1 hexy 1 octy 1 decy 1 phenyl benzyl pheriylethy 1 phenyIpropyl phenylpentyl 1-naphthyl 2-naphthyI 2-bromopheny1 3-bromophenyl 4-bromopheny1 2-chlorophenyl 3-chlorophenyl 4-chlorophenyl 2-fluorophenyl 3-fluorophenyl 4-fluorophenyl 2-methylphenyl 3-methylphenyl 4-methylphenyl 2-ethyl-phenyl 3-ethyl-phenyl 4-ethy1-phenyl oi 1 oil 2935,1729,1276,1069 2933,1727,1277,1069 7 23 890828 O.Z. 0050/41358 Table 1 (contd.) No. A-X-(ch2)n mP- IR: v(cm~l) 5 1.36 2-iso-propy1-pheny1 1.37 3-iso-propy1-pheny1 1.38 4-iso-propy1-pheny1 1.39 2-tert.-butyl-phenyl 1.40 3-tert.-butyl-phenyl 10 1.41 4-tert.-butyl-phenyl 1.42 4-buty1-pheny1 1.43 4-hexy1-pheny1 1.44 4-nony1-phenyI 1.45 4-decy1-pheny1 15 1.46 2-methoxy-pheny1 1.47 3-methoxy-phenyl 1.48 4-methoxy-pheny1 1.49 2-trifluoromethyl-phenyl 1.50 3-trifluoromethy1-pheny1 20 1.51 4-trifluoromethy1-pheny1 1.52 2-formylpheny1 1.53 3-formylpheny1 1.54 4-formy1pheny1 1.55 2-allyl-0-N=CH-phenyl 25 1.56 3-allyl-0-N=CH-phenyl 1.57 4-ally1-O-N-CH-phenyl 1.58 2-nitro-phenyl 1.59 3-nitro-phenyl 1.60 2,4-dichloropheny1 30 1.61 2, 5-dichlorophenyl 1.62 2,6-dichloropheny1 1.63 3, 4-dichloropheny1 1.64 2, 3-dichloropheny1 1.65 3, 5-dichlorophenyl 35 1.66 2, 3,4-trichlorophenyl 1.67 2,4,5-trichlorophenyl 1.68 2, 4, 6-trichlorophenyl 1. 69 2, 3, 4,6-tetrachloropheny1 1. 70 2, 3, 4, 5,6-pentachloropheny1 AO 1. 71 2, 3,4,5-tetrafluorophenyl 1. 72 2, 3, 5,6-tetrafluorophenyl 1. 73 2, 3, 4, 5,6-pentafluorophenyl 2 3 6 8 890828 8 O.Z. 0050/41358 Table 1 (contd.) No. A-X-(CH2)n mP- IR: v(cm_1) 5 1. 74 2-chloro, 4-fluorophenyl 1. 75 3-chloro, 4-fluorophenyl 1. 76 2-chloro, 6-methy1-pheny1 1. 77 4-chloro, 2-methy1-pheny1 1. 78 2,4-dichloro, 5-methy1-pheny1 10 1. 79 4-chloro, 2,5-dimethy1-phenyl 1. 80 4-bromo, 2-methy1-pheny1 1. 81 3,5-bistri fluoromethyl-pheny1 1. 82 2, 3-dimethyl-pheny1 1. 83 2,4-dimethy1-pheny1 15 1. 84 2,5-dimethy1-pheny1 1. 85 2,6-dimethy1-phenyl 1. 86 3,4-dimethyl-pheny1 1. 87 3,5-dimethyl-pheny1 1. 88 2, 4, 5-trimethyl-phenyl 20 1. 89 2, 6-diethy1-phenyl 1. 90 2, 4-di-tert.-butyl-phenyl 1. 91 2,5-dimethoxy-pheny1 1. 92 3,4-dimethoxy-pheny1 1. 93 2-methyl, 4-tert.-butyl-phenyl 25 1. 94 2-methoxycarbony1-phenyl 1. 95 2-ethoxycarbony1-pheny1 1. 96 2-propoxycarbony1-pheny1 1. 97 2-butoxycarbony1-phenyl 1. 98 2-cyano-phenyl 30 1. 99 3-cyano-phenyl 1. 100 4-cyano-pheny1 1. 101 1-naphthylmethyl 1. 102 2-naphthylmethy1 1. 103 2-bromobenzy1 35 1. 104 3-bromobenzy1 1. 105 4-bromobenzy1 1. 106 2-chlorobenzy 1 1. 107 3-chlorobenzyl 1. 108 4-chlorobenzyl 40 1. 109 2-fluorobenzy1 1. 110 3-fluorobenzy1 1. 111 4-fluorobenzy1 1. 112 2-methylbenzyl 2 3 6 8 2 4 890828 O.Z. 0050/41358 Table 1 (contd.) No. A-X-(CH2)n mP- IR: v(cm_1) 5 1 .113 3-methylbenzy1 1 .114 4-methylbenzyl 1 .115 2-methoxybenyzl 1 .116 3-methoxybenzy1 1 .117 4-methoxybenzy1 10 1 .118 4-ethoxybenzy1 1 .119 4-butyloxybenzyl 1 .120 4-benzyloxybenzyl 1 .121 2-tri fluoromethy1-benzyl 1 .122 3-trifluoromethy 1-benzyl 15 1 .123 4-trifluoromethy1-benzyl 1 .124 2-formylbenzy1 1 .125 3-formylbenzy1 1 .126 4-formylbenzy1 1 .127 2-allyl-0-N=CH-benzy1 20 1 .128 3-allyl-0-N=CH-benzyl 1 .129 4-allyl-0-N=CH-benzy1 1 .130 2-nitrobenzyl 1 .131 3-nitrobenzy1 1 .132 2,4-dichlorobenzyl 25 1 .133 2,6-dichlorobenzyl 1 .134 3,4-dichlorobenzyl 1 .135 2,3-dichlorobenzyl 1 .136 3,5-dichlorobenzyl 1 .137 2,3-dimethylbenzy1 30 1 .138 2,4-dimethylbenzy1 1 .139 2,5-dimethylbenzy1 1 .140 2,6-dimethylbenzy1 1 .141 3,4-dimethylbenzy1 1 .142 3,5-dimethylbenzyl 35 1 .143 4-chioro-2-methylbenzy1 1 .144 2-methoxycarbony1-benzyl 1 .145 2-ethoxycarbony1-benzyl 1 .146 2-butoxycarbony1-benzyl 1 .147 2-cyano-benzy1 40 1 .148 3-cyano-benzy1 1 .149 4-cyano-benzyl 1 .150 2-pyridyl 1 .151 3-pyridyl 10 890828 O.Z. 0050/41358 Table 1 (contd.) No. A-X-(CH2)n mp. IR: v(cm~l) 5 1. . 152 4-pyridyl 1. ,153 6-methyl-2-pyridy1 1. ,154 6-ethy1-2-pyridyl 1. 155 6-ri-propy 1-2-pyr idyl 1. ,156 6-n-buty1-2-pyridyl 10 1. ,157 6-tert.-buty1-2-pyridyl 1. 158 6-n-hexy1-2-pyridyl 1. 159 6-pheny1-2-pyridyI 1. 160 6-benzy1-2-pyridyl 1. 161 6-tri fluoromethyl-2-pyridyl 15 1. 162 6-methoxy-2-pyridy1 1 . 163 6-chloro-2-pyridy1 1 . 164 3,6-dimethyl-2-pyridy1 1. 165 4,6-dimethy1-2-pyridyl 1. 166 5,6-dimethy1-2-pyridyl 20 1. 167 4-phenyl-6-methy1-2-pyridyl 1. 168 3,4-dichloro-6-methyl-2-pyridy1 1. 169 3, 4, 5-trichloro-6-methyl-2-pyridyl 1 . 170 4-tri fluoromethy1-6-methy1-2-pyridyl 1. 171 3-acetyl-4, 6-dimethyl-2-pyridyl 25 1 . 172 3-cyano-6-methy1-2-pyr i dy1 1. 173 3-cyano-6-pheny1-2-pyridyl 1. 174 3-methyloxycarbony1-2-pyridy1 1. 175 3-methy loxycarboriy 1-6-iso-propy 1-2-pyr idyl 1. 176 5-tri fluoromethy1-2-pyridyl 30 1. 177 2-quinolyl 1 . 178 3-methy1-2-quinolyl 1. 179 4-phenyl-2-quinolyl 1. 180 8-chloro-2-quinoly1 1 . 181 4-methyl-8-methoxy-2-quinolyl 35 1. 182 4-quinolyl 1. 183 2,6-dimethyl-4-quinolyl 1 . 184 8-quinoly1 1 . 185 5,7-dichloro-8-quinolyl 1 . 186 2-pyrimidinyl 40 1 . 187 4-tri fluoromethy1-2-pyrimidiny1 1. 188 4,6-dimethyl-5-chloro-2-pyrimidinyl 1. 189 3,5-dimethy1-4-pyrimidiny1 1. 190 2-pyrazinyI n 2 3 6 8 2 4 : 890828 11 O.Z. 0050/41358 Table 1 (contd.) No. A-X-(CH2)n mP- IR: v(cm"^) 5 1.191 2-thienyl 1.192 3-thienyl 1.193 3-methy1-2-quinoxaliny1 1.194 3-pheny1-5-isoxazolyl 1.195 2-benzoxazoly1 10 1.196 2-benzthiazolyl 1.197 4-chloro-2-benzothiazoly1 1.198 5-chloro-2-benzothiazoly1 1.199 6-chloro-2-benzothiazoly1 1.200 6-methyl-2-benzothiazoly1 15 1.201 6-methoxy-2-benzothiazoly1 20 25 30 35 40 f) iL. C n ( 890828 12 O.Z. 0050/41358 Table 2 No. A-X-(CH 2) H3C02C A—X—(CH2)n NOCH 3 mp. IR: v(cm~1) 5 2. 2. 2. 2. 2. 10 2. 2. 2. 2. 2. 15 1 2 3 4 5 6 7 8 9 10 2.11 2.12 2.13 2.14 2.15 20 2.16 2.17 2.18 2.19 2.20 25 2.21 2.22 2.23 2.24 2.25 30 2.26 2.27 2.28 2.29 2.30 35 2.31 2.32 2.33 2.34 2.35 40 H methy 1 ethyl i sopropy1 butyl sec.-butyl t-butyI isobutyl penty1 pi valoy1 hexy 1 octy 1 decy 1 phenyl benzyl phenylethy1 phenylpropyl phenylpenty1 1-naphthy1 2-naphthy1 2-bromopheny1 3-bromophenyl 4-bromopheny1 2-chloropheny1 3-chloropheny1 4-chlorophenyl 2-fluorophenyl 3-fluorophenyl 4-fluorophenyl 2-methylphenyl 3-methylpheny1 4-methylphenyl 2-ethy1-phenyl 3-ethy1-phenyl 4-ethy1-phenyl oil oil 2935,1738,1722,1152,1043 2935,1726,1151,1042 23 6 8 890828 O.Z. 0050/41358 Table 2 (contd.) No. A-X-(CH£)n mP- IR: v(cm 5 2.36 2-iso-propyl-phenyl 2.37 3-iso-propyl-pheny1 2.38 4-iso-propyl-pheny1 2.39 2-tert.-butyl-phenyl 2.40 3-tert.-butyl-phenyl 10 2.41 4-tert.-butyl-phenyl 2.42 4-buty1-pheny1 2.43 4-hexy1-phenyl 2.44 4-nonyl-phenyl 2.45 4-decy1-phenyI 15 2.46 2-methoxy-pheny1 2.47 3-methoxy-pheny1 2.48 4-methoxy-pheny1 2.49 2-trifluoromethy1-pheny1 2.50 3-trifluoromethy1-pheny1 20 2.51 4-trifluoromethyl-phenyl 2.52 2-formylpheny1 2.53 3-formylpheny1 2.54 4-formylpheny1 2.55 2-allyl-0-N=CH-phenyl 25 2.56 3-allyl-0-N=CH-pheny1 2.57 4-allyl-O-N-CH-pheny1 2.58 2-nitro-phenyl 2.59 3-nitro-phenyI 2.60 2,4-dichlorophenyl 30 2.61 2,5-dichlorophenyl 2.62 2,6-dichlorophenyl 2.63 3,4-dichlorophenyl 2.64 2,3-dichloropheny1 2.65 3,5-dichlorophenyl 35 2.66 2,3,4-trichloropheny1 2.67 2,4,5-trichloropheny1 2.68 2,4,6-trichloropheny1 2. 69 2,3,4,6-tetrachlorophenyl 2. 70 2,3,4,5,6-pentachlorophenyl 40 2. 71 2,3,4,5-tetrafluoropheny1 2. 72 2, 3, 5,6-tetrafluorophenyl 2. 73 2,3,4,5,6-pentaf1uorophenyl 2. 74 2-chloro, 4-fluorophenyl 13 236 0 0 / o c 4 890828 14 O.Z. 0050/41358 Table 2 (contd.) Nc ). A-X-(CH2)n mP- 1 5 2. 75 3-chloro, 4-fluorophenyl 2. 76 2-chloro, 6-methy1-pheny1 2. 77 4-chloro, 2-methy1-phenyl 2. 78 2,4-dichloro, 5-methy1-pheny1 2. 79 4-chloro, 2, 5-dimethy1-phenyl 10 2. 80 4-bromo, 2-methy1-pheny1 2. 81 3, 5-bistri fluoromethy1-pheny1 2. 82 2,3-dimethy1-pheny1 2. 83 2,4-dimethyl-phenyl 2. 84 2,5-dimethy1-phenyl 15 2. 85 2,6-dimethy1-pheny1 2. 86 3,4-dimethyl-phenyl 2. 87 3,5-dimethy1-pheny1 2. 88 2, 4, 5-trimethy1-pheny1 2. 89 2,6-diethy1-phenyl 20 2. 90 2, 4-di-tert.-butyl-phenyl 2. 91 2, 5-dimethoxy-pheny 1 2. 92 3, 4-dimethoxy-pheny1 2. 93 2-methyl, 4-tert.-butyl-phenyl 2. 94 2-methoxycarbony1-phenyl 25 2. 95 2-ethoxycarbony1-phenyl 2. 96 2-propoxycarbony1-pheny1 2. 97 2-butoxycarbony1-phenyl 2. 98 2-cyano-pheny1 2. 99 3-cyano-phenyI 30 2. 100 4-cyano-pheny1 2. 101 1-naphthylmethyl 2. 102 2-naphthylmethyl 2. 103 2-bromobenzyI 2. 104 3-bromobenzy1 35 2. 105 4-bromobenzy1 2. 106 2-chlorobenzy1 2. 107 3-chlorobenzy1 2. 108 4-chlorobenzy1 2. 109 2-fluorobenzy1 40 2. 110 3-fluorobenzy1 2. 111 4-fluorobenzy1 2. 112 2-methylbenzy1 2. 113 3-methylbenzy1 2 3 6 8 2 4' ri 890828 15 O.Z. 0050/41358 Table 2 (contd.) No. A-X-(CH2)n mP- IR: v(cm_l) 5 2 114 4-methylbenzy1 2 115 2-methoxybenyzl 2 116 3-methoxybenzy1 2 117 4-methoxybenzy1 2 118 4-ethoxybenzy1 10 2 119 4-butyloxybenzyl 2 120 4-benzyloxybenzyl 2 121 2-tri fluoromethy1-benzyl 2 122 3-tri fluoromethy1-benzy1 2. 123 4-tri fluoromethy1-benzy1 15 2 124 2-formylbenzy1 2. 125 3-formylbenzy1 2. 126 4-formyIbenzyl 2. 127 2-allyl-0-N=CH-benzy1 2. 128 3-allyl-0-N=CH-benzy1 20 2. 129 4-allyl-0-N=CH-benzy1 2. 130 2-nitrobenzyl 2. 131 3-nitrobenzyl 2. 132 2,4-d chlorobenzyl 2. 133 2,6-d chlorobenzyl 25 2. 134 3, 4-d chlorobenzyl 2. 135 2, 3-d chlorobenzyl 2. 136 3,5-d chlorobenzyl 2. 137 2, 3-d methylbenzyl 2. 138 2,4-d methylbenzyl 30 2. 139 2,5-d methylbenzyl 2. 140 2,6-d methylbenzyl 2. 141 3, 4-d methylbenzyl 2. 142 3,5-d methylbenzyl 2. 143 4-chioro-2-methylbenzy1 35 2. 144 2-methoxycarbony1-benzy1 2. 145 2-ethoxycarbony1-benzy1 2. 146 2-butoxycarbony1-benzy1 2. 147 2-cyano-benzy1 2. 148 3-cyano-benzyl 40 2. 149 4-cyano-benzy1 2. 150 2-pyridy1 2. 151 3-pyridyl 2. 152 4-pyridyl 2 3 6 8 2 4 890828 O.Z. 0050/41358 Table 2 (contd.) NO. A-X -(CH2)n mp. IR: v(cm 1) 5 2. 153 6-methy1-2-pyridyl 2. 154 6-ethyl-2-pyridy1 2. 155 6-n-propy1-2-pyridy1 2. 156 6-n-buty1-2-pyridyl 2. 157 6-tert.-butyl-2-pyridy1 10 2. 158 6-n-hexy1-2-pyridyI 2. 159 6-pheny1-2-pyridy1 2. 160 6-benzy1-2-pyridyl 2. 161 6-tri fluoromethy1-2-pyri dy1 2. 162 6-methoxy-2-pyri dy1 15 2. 163 6-chloro-2-pyridy1 2. 164 3,6-dimethy1-2-pyridyl 2. 165 4,6-dimethy1-2-pyridyl 2. 166 5, 6-dimethy1-2-pyridyl 2. 167 4-pheny1-6-methy1-2-pyri dyl 20 2. 168 3,4-dichloro-6-methy1-2-pyridyl 2. 169 3,4,5-trichloro-6-methyl-2-pyridyl 2. 170 4-tri f1uoromethy1-6-methy1-2-pyridy1 2. 171 3-acetyl-4,6-dimethyl-2-pyridyl 2. 172 3-cyano-6-methy1-2-pyridy1 25 2. 173 3-cyano-6-pheny1-2-pyridyl 2. 174 3-methyloxycarbony1-2-pyridyl 2. 175 3-methy1oxyc arbony1-6-i so-propy1-2-py r i dy1 2. 176 5-tri fluoromethy1-2-pyri dyl 2. 177 2-quinolyl 30 2. 178 3-methy1-2-quinolyl 2. 179 4-pheny1-2-quinolyl 2. 180 8-chloro-2-quinoly1 2. 181 4-methyl-8-methoxy-2-quinoly1 2. 182 4-quinolyl 35 2. 183 2, 6-dimethyl-4-quinolyl 2. 184 8-quinolyl 2. 185 5,7-dichloro-8-quinolyl 2. 186 2-pyrimidiny1 2. 187 4-tri fluoromethyI-2-pyrimidiny1 40 2. 188 4, 6-dimethyl-5-chloro-2-pyrimidinyl 2. 189 3, 5-dimethyl-4-pyrimidiriy 1 2. 190 2-pyraziny1 2. 191 2-thieny1 o 16 ^ 236824 890828 17 O.Z. 0050/41358 Table 2 (contd.) No. A-X-(CH2)n mP- IR: v(cm-1) 5 2.192 3-thieny 1 2.193 3-methyl-2-quinoxalinyl 2.194 3-phenyl-5-isoxazolyl 2.195 2-benzoxazoly1 2.196 2-benzthiazolyl 10 2.197 4-chloro-2-benzothiazoly1 2.198 5-chloro-2-benzothiazoly1 2.199 6-chloro-2-benzothiazoly1 2.200 6-methyl-2-benzothiazoly1 2.201 6-methoxy-2-benzothiazolyl 15 20 25 30 35 40 o 18 236 890828 O.Z. 0050/41358 Table 3 No. 5 3. 1 3. 2 3. 3 3. 4 3. 5 10 3. 6 3. 7 3. 8 3. 9 3.10 15 3.11 3.12 3.13 3.14 3.15 20 3.16 3.17 3.18 3.19 3.20 25 3.21 3.22 3.23 3.24 3.25 30 3.26 3.27 3.28 3.29 3.30 35 3.31 3.32 3.33 3.34 3.35 A-X-(CH2), H3CO 20^(^0(^3 A-X-(CH2)n mP* IR: v(cm_1) n-buty1 phenyl 2-methoxypheny1 3-methoxypheny1 4-methoxypheny1 2-chlorophenyI 3-chloropheny1 4-chloropheny1 2-methylpheny1 3-methylpheny1 4-methylphenyl 2.3-dimethylpheny1 2.4-dimethylpheny1 2.5-dimethylphenyl 2.6-dimethylphenyl 3.4-dimethylphenyl 3.5-dimethylphenyl 4-chloro-2-methylpheny1 4-methoxycarbonylphenyl 4-ethoxycarbonylpheny1 4-butoxycarbonylpheny1 2-allyl-0-N=CH-pheny\ 3-allyl-0-N=CH-pheny1 4-allyl-0-N=CH-pheny I 2-pyridyl 6-methy1-2-py r i dy1 6-chloro-2-pyridyl 4-chloro-2-benzothi azoly1 5-chloro-2-benzothiazoly1 6-chloro-2-benzothi azoly1 2-methoxybenzy1 3-methoxybenzyl 4-methoxybenzyl 2-chlorobenzene 3-chlorobenzene 236824 o ^ 890828 19 O.Z. 0050/41358 Table 3 (contd.) No. A-X-(CH2)n mp. IR: v(cnfl) 5 3.36 4-chlorobenzy1 3.37 2-methylbenzy1 3.38 3-methylbenzy1 3.39 4-methylbenzy1 3.40 2,3-dimethylbenzy1 10 3.41 2, 4-dimethylbenzy1 3.42 2,5-dimethylbenzy 1 3.43 2,6-dimethylbenzy 1 3.44 3,4-dimethylbenzy 1 3.45 3,5-dimethylbenzy1 15 3.46 4-chloro-2-methylbenzy1 3.47 4-methoxycarbonylbenzyl 3.48 4-ethoxycarbonylbenzy1 3.49 4-butoxycarbonylbenzy1 3.50 2-allyl-0-N=CH-pheny1 20 3.51 3-allyl-0-N=CH-phenyl 3.52 4-allyl-0-N=CH-phenyl 25 30 35 40 T\ n 890828 20 O.Z. 0050/41358 Table 4 No. „-.-0 A—X— (CH 2),. h3co2c-^ch-ch3 A-X-(CH2)n mp. IR: v(cm 1) 5 4. 1 4. 2 4. 4. 4. 10 4. 4. 4. 8 4. 9 4.10 15 4.11 4.12 4.13 4.14 4.15 20 4.16 4.17 4.18 4.19 4.20 25 4.21 4.22 4.23 4.24 4.25 30 4.26 4.27 4.28 4.29 4.30 35 4.31 4.32 4.33 4.34 4.35 40 n-buty1 phenyl 2-methoxypheny1 3-methoxypheny1 4-methoxypheny1 2-chloropheny1 3-chloropheny1 4-chloropheny 1 2-methylpheny1 3-methylpheny1 4-methylphenyl 2.3-dimethylpheny1 2.4-dimethylpheny 1 2.5-dimethylpheny1 2.6-dimethylpheny1 3.4-dimethylpheny1 3.5-dimethylpheny1 4-chloro-2-methylpheny1 4-methoxycarbonylphenyl 4-ethoxycarbonylpheny1 4-butoxycarbonylpheny1 2-allyl-0-N=CH-phenyl 3-allyl-0-N=CH-phenyl 4-allyl-0-N=CH-phenyl 2-pyridyl 6-methy1-2-pyridyl 6-chloro-2-pyridyl 4-chloro-2-benzothi azoly 1 5-ch1oro-2-benzothi azoly1 6-chloro-2-benzothiazoly1 2-methoxybenzy1 3-methoxybenzyl 4-methoxybenzy1 2-chlorobenzene 3-chlorobenzene 2 3 6 8 2 4 890828 21 O.Z. 0050/41358 Table 4 (contd.) No. A-X-(CH2)n mp. IR: v(cm 1) 5 4.36 4-chlorobenzy1 4.37 2-methylbenzy1 4.38 3-methylbenzy 1 4.39 4-methylbenzy 1 4.40 2,3-dimethylbenzy1 10 4.41 2,4-dimethylbenzy 1 4.42 2,5-dimethylbenzy1 4.43 2,6-dimethylbenzyl 4.44 3,4-dimethylbenzyl 4.45 3,5-dimethylbenzyl 15 4.46 4-chloro-2-methylbenzy1 4.47 4-methoxycarbonylbenzyl 4.48 4-ethoxycarbonylbenzy1 4.49 4-butoxycarbonylbenzy1 4.50 2-allyl-0-N=CH-phenyl 20 4.51 3-allyl-0-N=CH-pheny1 4.52 4-allyl-0-N=CH-phenyl 25 30 35 40 o 22 890828 O.Z. 0050/41358 Table 5 A-X-(CH2)n^-Y^ H3C02<X^U NO. A-X-(CH2)n u mP- IR: v/cm~ 5 5, . 1 2-methylpheny1 ch2 5, . 2 3-methoxypheny1 ch2 5, . 3 4-chloropheny1 ch2 5, . 4 2-allyl-0-N=CH-pheny1 ch2 5, . 5 3-methoxycarbonylpheny1 ch2 10 5. . 6 6-chloro-2-pyridy1 ch2 5. . 7 6-chloro-2-benzothiazoly1 ch2 5, . 8 2-methylbenzy1 ch2 5. . 9 3-methoxybenzy1 ch2 5. .10 4-chlorobenzy1 ch2 15 5. .11 2-allyl-0-N=CH-benzyl ch2 5. .12 3-methoxycarbony1-benzy1 ch2 5. ,13 2-methylpheny1 CH-CH2-CH3 5. ,14 3-methoxypheny1 CH-CH2-CH3 5. ,15 4-chlorophenyl ch-ch2-ch3 20 5. 16 2-allyl-0-N=CH-pheny1 CH-CH2-CH3 5. 17 3-methoxycarbonylpheny1 ch-ch2-ch3 5. 18 6-chloro-2-pyridy1 ch-ch2-ch3 5. 19 6-chloro-2-benzothi azoly1 CH-CH2-CH3 5. 20 2-methylbenzy1 CH-CH2-CH3 25 5. 21 3-methoxybenzy1 ch-ch2-ch3 5. 22 4-chlorobenzy\ CH-ch2-ch3 5. 23 2-allyl-0-N=CH-benzy1 CH-ch2-ch3 5. 24 3-methoxycarbony1-benzy1 CH-ch2-ch3 5. 25 2-methylpheny1 N-NH-ch3 30 5. 26 3-methoxypheny1 N-NH-ch3 5. 27 4-chlorophenyl N-NH-ch3 5. 28 2-allyl-0-N=CH-pheny1 N-NH-ch3 5. 29 3-methoxycarbonylpheny1 N-NH-ch3 5. 30 6-chloro-2-pyridy1 N-NH-ch3 35 5. 31 6-chloro-2-benzothi azoly1 N-NH-ch3 5. 32 2-methylbenzy1 N-NH-ch3 5. 33 3-methoxybenzy1 N-NH-ch3 5. 34 4-chlorobenzy1 N-NH-ch3 5. 35 2-allyl-0-N=CH-benzyl N-NH-ch3 40 o / " 890828 23 O.Z. 0050/41358 Table 5 (contd.) No. A-X-(CH2)n u mP- IR: v/cnT1) 5 5.36 3-methoxycarbony1-benzy1 N-NH-ch3 5.37 2-methylpheny1 CH-S-ch3 5.38 3-methoxypheny 1 CH-S-ch3 5.39 4-chlorophenyl CH-S-ch3 5.40 2-allyl-0-N=CH-phenyl CH-S-ch3 10 5.41 3-methoxycarbonylpheny1 CH-S-ch3 5.42 6-chloro-2-pyridy1 CH-S-ch3 5.43 6-chloro-2-benzothiazoly1 CH-S-ch3 5.44 2-methylbenzy1 CH-S-ch3 5.45 3-methoxybenzy1 CH-S-ch3 15 5.46 4-chlorobenzy1 CH-S-ch3 5.47 2-allyl-0-N=CH-benzy1 CH-S-ch3 5.48 3-methoxycarbony1-benzyl CH-S-ch3 20 25 30 35 40 o 23 0 24 O.z. 0050/41358 In general terms, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the class consisting of the Ascomycetes and Basidiomycetes. Some of them have a systemic action and can be used as foliar and soil fungicides. 5 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 10 vegetables such as cucumbers, beans and cucurbits. The novel compounds are particularly useful for controlling the following plant diseases: 15 Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits, Podosphaera leucotricha in apples, Uncinula necator in vines, Puccinia species in cereals, 20 Rhizoctonia solani in cotton, Ustilago species in cereals and sugar cane, Venturia inaequalis (scab) in apples, Helminthosporium species in cereals, Septoria nodorum in wheat, 25 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, 30 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 35 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 40 as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; 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 emulsifiers and dispersants; if water o 2 3 6 8 25 O.Z. 0050/41358 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., chloro-benzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., 5 methanol, butanol), ketones (e.g., eyelohexanone), amines (e.g., ethanolamine, dimethyIformamide), and water; 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., polyoxyethy1-10 ene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as lignin, sulfite waste liquors and methylcellulose. The fungicides 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 15 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 (timber), e.g., against Paecilomyces variotii. when the active ingredients are used for treating seed, amounts of from 0.001 to 50, and preferably from 0.01 to 20, g per kg of seed are generally required. 20 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. 25 Examples of formulations are given below. I. A solution of 90 parts by weight of compound no. 2.15 and 10 parts by weight of N-methy1-a-pyrrolidone, which is suitable for application in the 30 form of very fine drops. II. A mixture of 20 parts by weight of compound no. 2.15, 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 35 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 finely dispersing the mixture in water, an aqueous dispersion is obtai ned. 40 III. An aqueous dispersion of 20 parts by weight of compound no. 2.15, 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 dispersing it therein, an aqueous dispersion is obtained. o 26 O.Z. 0050/41358 IV. An aqueous dispersion of 20 parts by weight of compound no. 2.15, 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 5 oil. By pouring the solution into water and finely dispersing it therein, an aqueous dispersion is obtained. V. A hammer-milled mixture of 80 parts by weight of compound no. 2.15, 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic 10 acid, 10 parts by weight of the sodium salt of a 1 ignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained. 15 VI. An intimate mixture of 3 parts by weight of compound no. 2.15 and 97 parts by weight of particulate kaolin. The dust contains 3wt% of the active ingredient. VII. An intimate mixture of 30 parts by weight of compound no. 2.15, 92 20 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. This formulation of the active ingredient exhibits good adherence. VIII. A stable aqueous dispersion of 40 parts by weight of compound no. 25 2.15, 10 parts of the sodium salt of a phenolsulfonic acid-urea- formaldehyde condensate, 2 parts of silica gel and 48 parts of water, which dispersion can be further diluted. IX. A stable oily dispersion of 20 parts by weight of compound no. 2.15, 30 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. 35 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 a greater fungicidal action spectrum. 40 Q 27 23 6 8 O.Z. 0050/41358 The following list of fungicides with which the novel compounds may be combined is intended to illustrate possible combinations but not to impose any restrictions. 5 Examples of fungicides which may be combined with the novel compounds are: sulfur, dithiocarbamates and their derivatives, such as ferric dimethyIdithiocarbamate, 10 zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethyIthiuram disulfides, 15 ammonia complex of zinc N,N'-ethylenebisdithiocarbamate, ammonia complex of zinc N,N'-propylenebi sdithiocarbamate, zinc N,N'-propylenebisdithioccarbamate and N,N'-polypropylenebis(thiocarbamyl) disulfide; 20 nitro derivatives, such as dinitro(1-methyIhepty1)-phenyl crotonate, 2-sec-buty1-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-buty1-4,6-dinitrophenyl isopropylcarbonate and diisopropyl 5-nitroisophthalate; 25 heterocyclic substances, such as 2-heptadecylimidazol-2-y1 acetate, 2,4-dichloro-6-(o-chloroani1ino)-s-tri azine, 0,0-diethy1 phthalimidophosphonothioate, 30 5-amino-1-[-bis-(dimethyl amino)-phosphinyl]-3-pheny1-1,2,4-tri azole, 2.3-dicyano-l,4-dith ioanthraquinone, 2-thio-1, 3-dithio[4,5-b]quinoxaline, methyl 1-(butylcarbamyl)-2-benzimidazolecarbamate, 2-methoxycarbonylami nobenzimidazole, 35 2-(fur-2-y1)-benzimidazole, 2-(thiazol-4-yl)benzimidazole, N-(1,1, 2, 2-tetrachloroethylthio)-tetrahydrophthalimide, N-trichloromethyIthi otetrahydrophthalimide, N-trichloromethy1thi ophthalimide, 40 N-dichIorofluoromethy1thio-N',N'-dimethy1-N-phenylsuIfuric acid diamide, 5-ethoxy-3-trichloromethyl-l, 2, 3-thiadiazole, 2-thiocyanatomethyIthiobenzothiazole, 1.4-dichloro-2, 5-dimethoxybenzene, n 28 " - •- U O.Z. 0050/41358 4-(2-chlorophenyIhydrazono) -3-methy 1-5-i soxazo lone, 2-thiopyridine 1-oxide, 8-hydroxyquinoline and its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-l,4-oxathiyne, 5 2,3-dihydro-5-carboxani1ido-6-methy1-1,4-oxathiyne 4, 4-dioxide, 2-methy1-5,6-dihydro-4H-pyran-3-carboxani1ide, 2-methy1furan-3-carboxani1ide, 2.5-dimethylfuran-3-carboxani1ide, 2,4,5-trimethy 1furan-3-carboxani1ide, 10 2,5-dimethyl-N-cyclohexylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2, 5-diethy1 furan-3-carboxamide, 2-methyIbenzan i1ide, 2-iodobenzani1ide, N-formyl-N-morpholine-2,2, 2-trichloroethylacetal, 15 piperazine-l,4-diylbis-(l-(2,2,2-trichloroethy1)-formamide), l-(3, 4-dichloroani1ino)-1-formylamino-2,2, 2-trichloroethane, 2.6-dimethyl-N-tridecyImorpholine and its salts, 2,6-dimethy1-N-cyclododecylmorpholine and its salts, N-[3-(p-tert.-butylphenyl)-2-methy1 propyl]-cis—2, 6-dimethyImorpholine, 20 N-[3-(p-tert.-butylpheny1)-2-methy1 propyl]-piperidine, l-[2-(2,4-dichlorophenyl)-4-ethyl-l,3-dioxolan-2-y1ethy1]-1H-1,2,4--triazole, 1-[2—(2,4-dichlorophenyl)-4-n-propy1-1,3-dioxolan-2-ylethyl]-lH-l, 2, 4--tri azole, 25 N-(n-propyI)-N-(2, 4, 6-trichlorophenoxyethy1)-N'-imidazoly1-urea, 1-(4-chlorophenoxy)-3, 3-dimethy1-1-(1H-1,2,4-triazol-l-y1)-butan-2-one, 1-(4-chlorophenoxy)-3,3-dimethy1-1- (1H-1,2,4-triazol-l-y1)-butan-2-ol, a-(2-chloropheny1)-a-(4-chloropheny 1 )-5-pyrimidinemethanol, 5-buty1-(2-dimethyl amino-4-hydroxy-6-methylpyrimi dine, 30 bis-(p-chlorophenyl)-3-pyridinemethanol, 1, 2-bis-(3-ethoxycarbony1-2-thioureido)-benzene, 1, 2-bis-(3-methoxycarbony1-2-thioureido)-benzene, and various fungicides, such as 35 dodecyIguanidine acetate, 3-[3-(3,5-dimethy1-2-oxyeyelohexy1)-2-hydroxyethy1]-glutaramide, hexachlorobenzene, DL-methyl-N-(2,6-dimethylphenyl)-N-fur-2-yl alanate, methyl DL-N-(2,6-dimethylpheny1)-N-(2'-methoxyacetyl)-alanate, 40 N-(2,6-dimethy 1pheny1)-N-chloroacetyl-DL-2-aminobutyrolactone, methyl DL-N-(2, 6-dimethylphenyl)-N-(pheny1 acetyl)-alanate, 5-methy1-5-v inyl-3-(3,5-dichlorophenyl)-2,4-dioxo-l, 3-oxazoli di ne, 3-[3,5-dichlorophenyl]-5-methy1-5-methoxymethy1-1, 3-oxazolidine-2, 4-dione, 3-(3, 5-dichlorophenyl)-l-isopropylcarbamylhydantoin, </div>

Claims

<div class="application article clearfix printTableText" id="claims"> o 2 3 6 € 29 O.Z. 0050/41358 N-(3,5-dichlorophenyl)—1,2-dimethylcyclopropane-l,2-dicarboximide, 2-cyano-[N-(ethy1 aminocarbony1)-2-methoximino]-acetami de, 1 -[2—(2,4-dichlorophenyl)-pentyl]-lH-l,2,4-triazole, 2,4-di fluoro-a-(lH-l,2, 4-triazol-l-ylmethyl)-benzhydryl alcohol, 5 N-(3-chloro-2,6-dinitro-4-tri fluoromethylpheny1)—5—trifluoromethy1-3-chloro-2-aminopyridine, and l-((bis-(4-fluorophenyl)-methyl silyl)-methyl) — 1H—1,2,4-triazole. Use Example 10 Action on brown rust of wheat Leaves of pot-grown wheat seedlings of the "Kanzler" variety were dusted with spores of brown rust (Puccinia recondita). The pots were then placed for 24 hours at 20 to 22°C in a high-humidity (90 - 95%) chamber. During 15 this period the spores germinated and the germ tubes penetrated the leaf tissue. The infected plants were then sprayed to runoff with aqueous liquors containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the plants were set up in the greenhouse at 20 to 22°C and a relative humidity of 65 to 707o. The 20 extent of rust fungus spread on the leaves was assessed after 8 days. The results show that active ingredient 2.15, applied as a 0.025wt% spray liquor, has a good fungicidal action (100%). 25 30 35 40 0 7/ p US, CA, AU, NZ, TW, KR, IL '' - ° WHAT ^/WE CLAIM IS: 30 o.z. 0050/41358 We_c-Ua-Uu_

1. Unsaturated cyclohexylacetic acid derivatives of the formula I in-sAJ 10 A-X—(CH2), H3co2C-^U where U is =NOCH3, =CHOCH3, =CH2, =CH-CH3, =CH-CH2~CH3, =N-NH-CH3 or =CH-S-CH3, n is from 0 to 10, A is hydrogen or substituted or unsubstituted alkyl, cycloalkyl, aryl or hetaryl, and X is a single bond when n is 0, or oxygen, sulfur or a single bond 15 when n is not 0, and the plant-compatible acid addition products and base addition products thereof.

2. A compound of the formula I as set forth in claim 1, where U is =NOCH3, 20 ri is 1, A is phenyl, and X is a single bond.

3. A fungicide containing an inert carrier and a fungicidally effective 25 amount of a compound of the formula I A-X-(CH2)n-S>\X I H3C02(X^U where U is =NOCH3, =CH0CH3, =CH2, =CH-CH3, =CH-CH2"CH3r =N-NH-CH3 or =CH-S-CH3, n is from 0 to 10, A is hydrogen or substituted or unsubstituted alkyl, cycloalkyl, aryl or hetaryl, and X is a single bond when n is 0, or oxygen, sulfur or a single bond when n is not 0, or a plant-compatible acid addition product or.base\?, addition product thereof. *-;i;30;35;i * "2 APR j.992^ \\ - 3 6 824 US,CA,AU, NZ, TW, KR, IL 31 O.Z. 0050/41358

4. An insecticide containing an inert carrier and an insecticida 11y effective amount of a compound of the formula I A-X-(CH2)n""S H3C0.. I where 5 U is =n0ch3, =ch0ch3, =CH2, =CH-CH3, =CH-CH2-CH3, =N-NH-ch3 or =CH-S-ch3, n is from 0 to 10, 10 A is hydrogen or substituted or unsubstituted alkyl, cycloalkyl, aryl or hetaryl, and X is a single bond when n is 0, or oxygen, sulfur or a single bond when n is not 0, or a plant-compatible acid addition product or base 15 addition product thereof.

5. A process for combating fungi, wherein the fungi or the plants, seed, materials or the soil to be protected against fungus attack are treated with a fungicidally effective amount of a compound of the U is =noch3, =ch0ch3, =ch2, =ch-ch3, =ch-ch2~ch3, =n-nh-ch3 or =ch-s-ch3, 25 n is from 0 to 10, A is hydrogen or substituted or unsubstituted alkyl, cycloalkyl, aryl or hetaryl, and 30 X is a single bond when n is 0, or oxygen, sulfur or a single bond when n is not 0, or a plant-compatible acid addition product or base addition product thereof. 20 formula I I where 35 32

6. A compound as claimed in claim 1 as specifically set forth herein.

7. A process for producing a compound as claimed in claim 1 substantially as herein described with reference to any one of the Examples. BASF AKTIENGESELLSCHAFT BALDWIN, SON & CAREY </div>