AU658291B2 - Novel benzyl enol ethers and their use as crop protection agents - Google Patents
Novel benzyl enol ethers and their use as crop protection agents Download PDFInfo
- Publication number
- AU658291B2 AU658291B2 AU38227/93A AU3822793A AU658291B2 AU 658291 B2 AU658291 B2 AU 658291B2 AU 38227/93 A AU38227/93 A AU 38227/93A AU 3822793 A AU3822793 A AU 3822793A AU 658291 B2 AU658291 B2 AU 658291B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- substituted
- unsubstituted
- phenyl
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 benzyl enol ethers Chemical class 0.000 title claims abstract description 504
- 239000011814 protection agent Substances 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 20
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 20
- 150000002367 halogens Chemical class 0.000 claims abstract description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 239000000417 fungicide Substances 0.000 claims abstract description 10
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 9
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims abstract description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 6
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 5
- 150000001408 amides Chemical class 0.000 claims abstract description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 4
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims abstract 4
- 125000002252 acyl group Chemical group 0.000 claims abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract 2
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract 2
- 125000005347 halocycloalkyl group Chemical group 0.000 claims abstract 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 241000196324 Embryophyta Species 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 9
- 230000000855 fungicidal effect Effects 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 150000002085 enols Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 235000009917 Crataegus X brevipes Nutrition 0.000 claims 1
- 235000013204 Crataegus X haemacarpa Nutrition 0.000 claims 1
- 235000009685 Crataegus X maligna Nutrition 0.000 claims 1
- 235000009444 Crataegus X rubrocarnea Nutrition 0.000 claims 1
- 235000009486 Crataegus bullatus Nutrition 0.000 claims 1
- 235000017181 Crataegus chrysocarpa Nutrition 0.000 claims 1
- 235000009682 Crataegus limnophila Nutrition 0.000 claims 1
- 235000004423 Crataegus monogyna Nutrition 0.000 claims 1
- 240000000171 Crataegus monogyna Species 0.000 claims 1
- 235000002313 Crataegus paludosa Nutrition 0.000 claims 1
- 235000009840 Crataegus x incaedua Nutrition 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 210000002837 heart atrium Anatomy 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 130
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 16
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 7
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 7
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 5
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 4
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 4
- 235000012054 meals Nutrition 0.000 description 4
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 4
- 125000000466 oxiranyl group Chemical group 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 3
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 3
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 3
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 3
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 3
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 3
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 description 3
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241001281803 Plasmopara viticola Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 3
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 2
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical class COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 2
- 125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 2
- DOGUTBVQUQYPFC-UHFFFAOYSA-N 3-hydroxy-2-(4-methylphenyl)prop-2-enenitrile Chemical compound CC1=CC=C(C(=CO)C#N)C=C1 DOGUTBVQUQYPFC-UHFFFAOYSA-N 0.000 description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- 208000015181 infectious disease Diseases 0.000 description 1
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- 235000019341 magnesium sulphate Nutrition 0.000 description 1
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- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
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Classifications
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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- A—HUMAN NECESSITIES
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
- C07D311/46—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids
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Abstract
Benzyl enol ether derivatives of the formula I <IMAGE> in which A denotes CH2, CHCl, CH-alkyl, CH-O-alkyl, CH-S-alkyl, N-O-alkyl and B denotes OH, alkoxy, alkylthio and alkylamino, U, V and W are identical or different and denote hydrogen, halogen, alkyl and alkoxy, R<1>, R<2> and R<3> are identical or different and denote hydrogen, cyano, halogen, amino, ester, amide, acyl, S(O)nR<4>, PO(OR<4>)2, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkyl-alkyl, alkoxy-alkyl, alkylthio-alkyl, arylthio-alkyl, alkenyl, haloalkenyl, cycloalkenyl, halocycloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, benzylthio, alkylcarbonyl, optionally substituted phenylcarbonyl, optionally substituted benzylcarbonyl, alkoxycarbonyl, optionally substituted phenoxycarbonyl, optionally substituted benzyloxycarbonyl, optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylthio, optionally substituted arylalkyl, optionally substituted arylalkenyl, optionally substituted aryloxyalkyl, optionally substituted arylthioalkyl, optionally substituted hetaryl, optionally substituted hetaryloxy, optionally substituted hetarylthio, optionally substituted heteroarylalkyl, optionally substituted hetarylalkenyl, optionally substituted hetaryloxyalkyl, optionally substituted heterocyclyl and optionally substituted heterocyclyloxy, and the radical R<4> denotes hydrogen and C1-C4-alkyl, and R<1> and R<3> together and also R<2> and R<3> together can in each case form a carbocyclic or heterocyclic ring which, in turn, can be benzo-fused and substituted, and fungicides containing these compounds.
Description
PAY'Je1i I 28dtl Regutation 3.2(2)
AUSTRALIA
Patents Act 1990 2N )4 I ~j L
ORIGINAL
COMPLETE SPECIFICATION STANDARD PATENT S. S.
S."
S
4* .9 *4 Application Number: Lodged: Invention Title: NOVEL BENZYL ENOL ETHERS AND THEIR USE AS CROP PROTECION AGENTrS The following statement is a full description of this Invention, including the best method of performing it known to :-US O.Z. 0050/43197 Novel benzyi enol ethers and their use as crop protection agents The present invention relates to novel benzyl enol ethers, pesticides containing them, in particular fungicides, and to a process for controlling pests, in particular fungi, insects, nematodes and spider mites, using these compounds.
It is known that f-methoxyacrylates, for example methyl 2- [2-(phenyloxymethylene)phenyl ]-3-methoxyacrylate (EP 178 826) and also oxime ethers, for example methyl 2- [2-(phenyloxymethylene)phenyl]glyoxylate 0-methyloxime ether (cf. EP 253 213) have fungicidal or insecticidal activity. Their action, however, is unsatisfactory.
It has now surprisingly been found that benzyl 15 enol ethers of the general formula I U V W
R
3
A
where A is
CH
2 CHC1, CH-C-C 4 -alkyl, CH-O-Cl-C 4 -alkyl, CH-S-C 1
-C
4 alkyl, N-O-Cl-C 4 -alkyl, B is OH, Cl-C 4 -alkoxy, C,-C 4 -alkylthio and Cl-C 4 -alkylamino, U, V and W are identical or different and are hydrogen, halogen, Cl-C 4 -alkyl or Cl-C 4 -alkoxy,
R
2 and R 3 are identical or different and are hydrogen, cyano, halogen, NR 4
R
S
C0 2
R
4
CONR
4
R
5
COR
4
S(O),R
4 where n 0, 1 2 0050/43197 or 2, PO(0R 4 unbranched or branched C,-C 1 -alkyl, Cl-C,haloalkyl, C 3
-C
6 -CYCloalkyl, C-C 6 -halocycloaikyl, C 3
-C
6 cycloalkyl-Cl-C,-alkyl,
C
1
-C
4 -alkoxy-C,-C-alkyl, C1-C 4 alkylthio-Cl-C 4 -alkyl, arylthio-Cl-C 4 -alhyl, C 2 -C-alkenyl,
C
2 -C-haloalkenyl, C 3 -C-cycloalkenyl C 3
-C
6 -halocycloalkenyl, C 2 -C-alkynyl, Cl-C 6 -alkoxy, C,-C-haloalkoxy, Cl-C 4 -alkylthio, benzylthio, C 1
-C
4 -alkylcarbonyl, unsubstituted or substituted phenylcarbonyl, unsubstituted or substituted benzylcarbonyl, CI-C 4 alkoxycarbonyl, unsubstituted or substituted phenoxycarbonyl, unsubstituted or substituted benzyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylthio, unsubstituted or substituted aryl- Cl-C 4 -alkyl, unsubstituted or substituted aryl-.C 2
-C
4 alkenyl, unsubstituted or substituted aryloxy-C 1
-C
4 -alkyl, unsubstituted or substituted arylthio-Cl-C 4 -alkyl, unsubstituted or substituted hetaryl, unsubstituted or substituted hetaryloxy, unsubstituted or substituted hetarylthio, unsubstituted or substituted heteroaryl-Cl-C 4 -alkyl, unsubstituted or substituted hetaryl-C 2
-C
4 -alkenyl, *unsubstituted or substituted hetaryloxy-Cl-C 4 -alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyloxy, where unsubstituted or substituted, in addition to hydrogen, includes the radicals halogen, cyano, nitro, :Cl-C 4 -alkyl, C,-C 4 -alkoxy, C,-C 4 -haloalkyl, C-C 4 -haloalkoxy, C 1
-C
1 0 -alkoximino-C 1
-C
2 -alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, C 3
-C
6 -cycloalkyl, heterocyclyl, heterocyclyloxy, and the radicals R 4 and R' are identical or different and are hydrogen or C 1
-C
4 alkyl,
R
1 and R' together, and also R 2 and R 3 together, in each case can form a carbocyclic or a heterocyclic ring which can in turn be benzo-fused and can be substituted by the 3 O.Z. 0050/43197 radical mentioned under unsubstituted or substituted, where, inter alia, the following ring systems A F are possible: the symbol 0 is the group U VW CH2in the following 0 Or, e* 1.
x 0 R2 -4 O.Z. 0050/43197 where X is CH2 1 0, NR 4 Y is CH, CH 2 1 where n 0, 1 or 2, z is hydrogen, halogen, C 1
-C
4 -alkyl or Cl-C 4 -alkoxy and R 4 is hydrogen or Cl-C 4 -alkyl and is a single bond or a double bond, have an excellent fungicidal, insecticidal, nematicidal and acaricidal action which is better than that of the known ,-methoxyacrylates or oxime ethers. The fungicidal action is preferred.
The radicals shown in the general formula I can have, for example, the following meanings:
A
can be, for example, Cl-C 4 -alkylidene (eg. methylidene, ethylidene, n- or isopropylidene, iso-, sec- or tertbutylidene), Cl-C 4 -alkoxymethylidene (eg. methoxy-, *ethoxy-, n- or isopropoxy, iso-, sec- or tert-butoxymrethylidene), Cl-C 4 -alkylthiomethylidene (eg. methyl-, ethyl-, n- or isopropyl, iso-, sec- or tert-butylthiomethylidene), C 1
-C
4 -alkoxyimino (eg. methoxy-, i. 25 ethoxy-, n- or isopropoxy, iso-, sec- or tert-butoxyimino), chloromethylidene,
B
can be OH, C 1
-C
4 -alkoxy (for example methoxy, r'thoxy, nor isopropoxy, iso-, sec- or tert-butoxy) CI-C 4 alkylthio (eg. methylthio, ethylthio, n- or isopropylthio, iso-, sec- or tert-butylthio) and Cl-C 4 -alkylamine (eg. methylamine, ethylamine, n- or isopropylamine, iso-, sec- or tert-butylamino), U, V and W can be, for example, H, halogen (eg. fluorine, chlorine, 5 O.Z. 0050/43197 bromine, iodine), methyl, methoxy, RI, R 2 and R 3 can be identical or different and are hydrogen, cyano, halogen (for example fluorine, chlorine, bromine, iodine), NR 4 C0 2
R
4
CONR
4 COR S where n 0, 1 or 2, PO(0R 4 2 where the radicals R 4 and R' are identical or dif ferent and are hydrogen or Cl-C 4 -alkyl (f or example methyl, ethyl, n- or isopropyl, iso-, sec- and tert-butyl),
R
1 R 2 and R 3 can also be unbranched or branched Cl-Cl 0 -alkyl (for example methyl, ethyl, n- or isopropyl, iso-, sec- or 15 tert-butyl, iso-, sec-, tert- or neopentyl, n-hexyl,
*C,-C
4 -haloalkyl (eg. trifluoromethyl, 2-f luoroethyl, S. 2,2, 2-trifluoroethyl, pentafiiioroethyl, fluorodichloromethyl, difluorochlorometbhyl, chloromethyl, dichloromethyl, trichloromethyl, 2-ch'Loroethyl, 2,2,2-trichloroetyl .etclroty)
C
3
-C
6 -CYCloalkyl (eg. cyclopropyl, cyclobutyl, cyclopentyl, ccoey)
C
3
-C
6 -halocycloalkyl (eg. 2, 2-difluorocyclopropyl, 2,2dichlorocyclopropyl, 2, 2-dibromocyclopropyl, 2,2dichloro-3-methylcyclopropyl, tetrafluorocyclobutyl) C 3 C.-cycloalkyl-Cl-C 4 -alkyl (eg. 1-methylcyclopropyl, 2,2dimethylcyclopropyl, 1-methylcyclohexyl),
CI-C
4 -alkoxy-Cj-C, 4 -alkyl (eg. methoxymethyl, ethoxymethyl, n- or isopropoxymathyl, iso-, sec- or tert-butoxymethyl, 2-methoxy-prop-2-yl, 2-ethoxyprop-2-yl, 2-n- or isopropoxyprop-2-yl, iso-, sec- or tert-biutoxyprop-
C
1
-C
4 -alkylthio-Cj-C,-alkyl (eg. methylthiomethyl, ethyln- or isopropylthiomethyl, iso-, sec- or tert-butylthiomethyl, 2-methylthioprop-2-yl, 2-ethylthioprop-2-yl, 2-n- or isopropylthio-prop-2-yl, 2-n-, -6 O.Z. 0050/43197 iso-, sec- or tert-butylthio-prop-2-yl), aryl (phenyl) thio-Cl-C 4 ,-alkyl (eg. phenyithiomethyl, 2chlorophenyl-thiomethyl), 1 -C-alkenyl (eg. vinyl, 1-propenyl, 2-propenyl, 2- .atn y 1, 3-butenyl, 1-methyl-2-propenyl, 3-methyl-2butenyl, 2-methyl-2-penten-5-yl),
C
2
-C
5 -haloalkenyl (eg. 2 ,2-difluorovinyl, 2, 2-dichiorovinyl, 3,3,3-trifluoropropenyl, 3,3,3-trichioropropenyl, 3-chloro-2-propenyl), C,-C,-cycloalkenyl (eg. cyclopent-1-enyl, cyclopentadienyl, cyclohex-l-enyl),
C
3
-C
6 -halocycloalkenyl (eg. pentafluorocyclopentadienyl, pentachlorocyclopentadienyl),
C
2
-C
4 -alkynyl (eg. ethynyl, 1-propynylf 1-propargyl), Cl-C 4 -alkoxy (eg. methoxy, ethoxy, n- or isopropoxy, n-, iso-, sec- or tert-butoxy), 99 Cl-C 4 -alkylthio (eg. methylthio, ethylthlo, n- or isopropylthio, iso-, sec- or tert-butylthio) benzylthio, Cl-C 4 -haloalkoxy (eg. trif luoromethoxy, pentaf luoroethoxy, 1,1,2, 2-tetrafluoroethoxy), Cl-C,-alkylcarbonyl (eg. acetyl, propionyl, butyryl, isobutyryl, piva&loyl), unsubstituted or substituted phenylcarbonyl (eg. benzoyl, 4-ohlorobenzoyl), unsubstituted or substituted benzylcarbonyl (eg. benzylcarbonyl),
C
1
-C
4 -Clkoxycarbony1 (eg. methoxycarbonyl, ethoxycarbonyl, n- or isopropoxycarbonyl, iso-, sec- or tertbutoxycarbonyl), unsubstituted or substituted phenoxycarbonyl (eg.
phenoxycarbonyl, 4-chiorophenoxycarbonyl), unsubstituted or substituted benzyloxycarbonyl (eg.
benzyloxycarbonyl), unsubstituted or substituted aryl (eg. phenyl, naphthyl, anthryl), unsubstituted or substituted aryloxy (eg. phenoxy, 7 O.Z. 0050/43197 naphthoxy, anthroxy), unsubstituted or substituted arylthio (eg. phenylthio), unsubstituted, or substituted aryl-C 2 -C,-alkyl (eg. benzyl, I.-Pheneth', 2-phenethyl, 1-phenyipropyl, 2-phenylpropyl, 3-phenyipropyl, 2-methyi-3-phenylpropyl, 2-methyl-2phenyipropyl, 4-phenylbutyl), unsubstituted or substituted aryl-C,-C 4 -alkenyl (eg.
phenyl-l-ethenyl, 2-phenyl-1-propenyl, 2, 2-diphenylethenyl, 1-phenyl-1-propen-2-yl, 1-phenyl-1-ethenyl), unsubst.ituted or substituted arv,1OXY-C 1
-C
4 -alkyl (eg.
phenoxyltethyl), unsubstituted, or substituted arylthio-C 1 -C.-alkyl (eg.
phenyithiomethyl), unsubstituted or substituted hateroaryl (eg. pyridyl, 2- 15 pyridyl, 3-pyridyl, 4-pyridyl, pyrimidinyl, -yid, inyl, 2-pyrimidinyl, thienyl, 2-thienyl, 3-thienyl, furyl, 2-furyl, 3-furyl, 1-pyrrolyl, 1-imidazolyl, 1,2,4triazolyl, 1,3,4-triazolyl, 4-thiazolyl, 2-benzothiazoly 1 urtsubstituted or substituted heteroaryloxy 2pyridyloxy, 2-pyrimi~dinyloxy), unsubstituted 'or substituted heteroarylthio (eq. 2pyridylthio, 2-pyrimidinylthio, 2-benzothiazolylthio), unsubstituted, or substituted heteroaryl-Cl-C.-alkyl (eg.
2-py~idylmethyl, 3-pyridylmethyl), unsubstituted or substituted heteroaryloxy-Cl-C 4 -alkyl furfurylmethoxy, thienylmethoxy, 3-isoxazolylmethoxy, 2-oxazoymetho.xcy, 2-pyridylmethoxy), unsubstituted or substituted heteroaryl-C 2
-C
4 ,-alkenyl (eg.
2 '-furyl-2-ethenyl, 2 '-thienyl-2-ethenyll 3 '-pyridyl-2ethenyl), unsubstituted, or substituted heterocyclyl (eg. oxiranyl, 1-aziridinyl, 1-azetidiniyl, 1-pyrrolidinyl, 2-tetrahydrofuryl, 2-tetrahydrcjrjranyl, 3-tetrahydropyralyl, 1piperidinyl, 1-morpholinyl, 1-piparazinyl, 1, 3-dioxany-, 3-tetr, iydrothiopyranyl), unsubstituted or substituted heterocycloxy (eg. 2- 8 O.Z. 0050/43197 dihydropyranyloxy, 2 -tetrahydropyranyloxy).
The radicals called unsubstituted or substituted in tha above are, in addition to hydrogen, for example, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoromethoxy, 1, 1,2, 2-tetrafluoroethoxy, methoxyiminomethyl, ethoxyiminomethyl, n-propoxyiminomethyll n-butoxyiminomethyl, n-pentoxyiminomethyl, n-hexoxyiminomethyl, allyloxyiminomethyl, benzyloxyiminomethyi, isopropoxyiminomethyl, isohutoxyiminomethyl, tert-butoxyiminomethyl, methylimino- -ethyl, etho~ryimino- 1 ty, n-propoxyimino- 1ethyl, n-butoxyimino-1-ethyl, n-pentoxyimino-1-ethyl, n- 1: S ~1 hexoxyimino-1-ethyl, allyloximino-1-ethyl, bnyoy imino-1-ethyl, phenyl, phenoxy, benzyloxy, imidazol-1-yl, piperazin- l-yl, 4-morpholinyl, piperidin- l-yl, pyridyl- 2-oxy, cyclopropyl, cyclohexyl, oxiranyl, 1, 3-dioxan-2yl, 1, 3-dioxolan-2-yl, tetrahydropyran-2-yloxy.
R' and R 3 together, and also R 2 and R 3 together, in each *case can form a carbocyclic or a heterocyclic ring which can in turn be benzo-fused and can be substituted by the radical mentioned under unsubstituted. or substituted, where, inter alia, the following ring systems A F are possible: ~4 .4the symbol is the group U V W in the following 0050/43197 0 0 or z Y-x or z- 0 2 0 R 000 000 0 *0 0or where X is
:CH
2
N
4 CH.0,N y is CHI, where n 1 or 2, z is H, halogen (for example fluorine, chlorine, bromine, iodine) Cl-C 4 -alkyl (for example methyl, ethyl) and C 1
-C
4 alkoxy (for example methoxy, ethoxy), R 4 is hydrogen and C 1
-C
4 -alkyl (for example methyl, ethyl, npropyl and n-butyl).
Preferred compounds of the general formula I are 10 O.Z. 0050/43197 those in which A is
CHCH
3
CH-CH
2
CH
3
CH-OCH
3
NOCH
3 B is
OCH
3
NHCH
3 U, V and W are hydrogen R R 2
R
3
R
4 and R are identical or different and have the meanings described in claim 1.
The novel compounds of the general formula I can be obtained as E/Z isomer mixtures during preparation owing to the C=C or C=N double bonds. These can be separated into the individual components in the customary S 15 manner, for example by crystallization or chromatography.
Both the individual isomeric compounds and their mixtures are encompassed by the invention and are utilizable as Spesticides.
The compounds of the general formula I as claimed 20 in claim 1 are prepared, for example, as described in Scheme Scheme 1.
0e00 "0 0 0, so 0 o.z. 0050/43197 11 scheme 1 v w u v' 4- U VW U V 0 0 0 44 0 L L 0
R
U VW R 900 *0 9 0 00
A
1 UVW 2
R
0 R
B
12 O.Z. 0050/43197 The compounds of the general formula I where A is CH,, CH-alkyl or CH-alkoxy can be prepared, for example, from the ketoesters 4 by Wittig or Wittig-Horner reaction (cf. EP 348 766, DE 3 705 389, EP 178 826). The similar compounds 5 are likewise obtained from the ketoesters 2.
Alternatively, a procedure can be used in which compounds of the formula 7 or 9 are condensed with suitable reagents, for example: for A CH, with formaldehyde (see DE 3 317 356), for A CH-alkyl a) with aldehydes (cf. D.M. Brown, J. Chem. Soc. 1948, 2147) or b) first with N,N-dimethylformamide dimethyl acetal, followed by reaction with a Grignard reagent (similarly to C. Jutz Chem. Ber. 91 (1958), 1867), for A CH-Oalkyl with ethyl formate followed by alkylation (see EP 178 826). Other preparation procedures for the compounds of the formula 5 and I where A CH-O-alkyl are described in EP 178 826.
A further possibility for preparing the compounds of the formula I where A CH-alkyl and B O-alkyl is the reaction of ketene acetals with phenyl chlorocarbonates (see N. Slougni, G. Rousseau, Synth. Commun.
12 (1982) 401-7).
For compounds of the general formula I in which 6*'C A is CH-S-alkyl and A is CHC1, the preparation can be carried out by the methods from EP 244 077 or 310 954.
The intermediates of the formula 3, 6 or 8 can be prepared from the compounds 2, 5 and 7 by halogenating these according to known methods, for example with chlorine, bromine or N-bromosuccinimide in an inert solvent (for example CC1, or cyclohexane) under illumination with, for example, an Hg vapor lamp or free radical initiators, such as, for example, dibenzoyl peroxide, or by introducing the radicals L such as, for example, mesylate, tosylate, acetate or triflate by means of suitable intermediate compounds (L halogen, OH).
The oxime ethers of the formula I where A N-Oalkyl can be prepared from 4 a) by reaction with 0-alkyl- 13 O.Z. 0050/43197 hydroxylamine hydrochloride or b) with hydroxylamine hydrochloride and subsequent alkylation with an alkylating agent (such as, for example, alkyl iodide, dialkyl sulfate etc.) (cf. DE 3 623 921).
Likewise, similarly to the method in EP 254 426, a phenylacetic ester of the formula 9 can be converted into its anion using a base (such as, for example, NaOMe, NaH, K tert-butoxide, etc.) in a solvent (such as, for example, diethyl ether, toluene, tert-butanol etc.) and oximated using a suitable nitrosating agent (such as, for example, methyl nitrite, amyl nitrite, tert-butyl nitrite etc.). The resulting oximate is alkylated using an alkylating agent (such as, for example, alkyl iodide, dialkyl sulfate).
S 15 The same processes can correspondingly also be transferred to the compounds of the formula 2 or 7, where the resulting oxime ethers 5 can as known (EP 254 426) be converted into the target compounds I via the intermediates 6 (L eg. halogen).
20 Customarily, in the preparation processes described above the radical B is alkoxy and U, V and W are H.
The compounds where B OH (11) can be prepared by methods known from the literature (Organikum 16th edition, p. 415, 622) from the compounds of the general formula I where B is 0-alkyl (10) (see Scheme 2): 14 4 0050/43197 Scheme 2: U V U V ,I 3
R
R
R 2 0~R3 R *0 .i N-Alkyl a 3 r x S-Alky.
S.
5 Starting from the carboxylic acids 11 thus obtained, the acid chlorides 12 can be prepared in a manner known per se (cf. Organikum 16th edition, (1985) p. 423f B. The conversion of 12 to the amides 13 is carried out similarly to Organikum 16th edition (1985) p. 412.
15 O.Z. 0050/43197 The thioesters 14 are obtained from the acid chlorides 12 (similarly to Houben-Weyl Vol. 8 (1952), p. 464 et seq.).
Alternatively, the thioesters 14 can also be prepared from the acids 11 (similarly to Houben-Weyl Vol.
(1985), p. 855 et seq.).
The amides 13 can also be prepared from the ester by methods known from the literature.
The preparation of the compounds of the general formulae 2 and 7 having ortho-methyl substitution on the aromatic ring is known (B 0-alkyl; U, V and W H; see EP 178 826, EP 260 832).
The enols required for preparing the compounds of the general formula I are either known or can be prepared by methods known per se, for example by reacting an activated methylene unit 15 with a formic acid ester in the presence of a base, such as, for example, NaH, or sodium methoxide (cf. Scheme 3).
Scheme 3:
*OH
*I Base H OR R R H Other methods of preparation are found in Houben- Weyl, Methoden der Organischen Chemie (Methods of Organic Chemistry), Vol. 6/11, (1977), pages 1-217.
The novel compounds of the general formula I as 25 claimed in claim 1 are prepared, for example, by reacting an enol 16 a or the tautomeric ketone 17 a with a benzyl compound of the formula 6.
16 O.Z. 0050/43197 0 vw UV W HO R 2 S 1 3 3 R R O t A or 16 aA B 0 R B R R 11 a
R
1
R
3 A, B, U, V and W have the meaning described in claim 1; L is a leaving group (for example chloride, bromide, iodide, triflate, methanesulfonate, ptoluenesulfonate).
5 The reactions described can be carried out, for example, in an inert solvent or diluent (for example acetone, acetonitrile, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone) using a base (for example sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, sodium methoxide).
The reaction can also be carried out in a twophase system (for example dichloromethane, water) with the addition of a suitable phase transfer catalyst (for example cetyltrimethylammonium chloride, benzyltriethyl- 15 ammonium chloride).
EXAMPLES
Methyl E/Z-2-methoximino-2-[2-cyano-2-(4-methyl)phenylethen-l-yloxymethyl]phenylacetate (compound 2.100; Table 2) 2.8 g (17.5 mmol) of 3-hydroxy-2-(4-methylphenyl)acrylonitrile, 2.6 g of potassium carbo.nate and 100 mg of potassium iodide are added to a solution of 5 g (17.5 mmol) of methyl 2-methoximino-2-(2'-bromomethyl)- 17 O.Z. 0050/43197 phenylacetate in 80 ml of acetone and the mixture is stirred at room temperature (20°C) for 16 hours. It is then poured into water, extracted with ethyl acetate, and the organic phase is dried and concentrated. 6.2 g (97%) of colorless solid remain, having a melting point of 93- 0 C. Isomer distribution according to GC: 7:1. E- to Zisomer 1 H-NMR (CDCl 3 6 2.34 3H, isomer 1 3.73; 4.03
OCH
3 isomer 3.87; 4.03 OCH 3 isomer 4.99 CH, isomer 5.00 CH,, isomer 6.97 7.61 ppm aryl-H and =CH).
Methyl E/Za-[2{2-cyano-2-(4-methyl)phenyl-ethen- 1-yloxy}methylphenyl]-A-methoxy-acrylate (compound 1.100; Table 1) 0* 20 o r 1.7 g (11 mmol) of 3-hydroxy-2-(4-methylphenyl)acrylonitrile, 1.6 g of potassium carbonate and 100 mg of potassium iodide are added to a solution of 3 g (11 mmol) of methyl 3-methoxy-2-(2'-bromomethyl)phenylacrylate in 50 ml of acetone and the mixture is stirred at room temperature for 16 hours. It is poured into water and extracted with ethyl acetate, and the organic phase is dried and concentrated. 3.6 g of a yellow oil remain. Isomer ratio according to GC: 5:1 E- to Z-isomer.
1 H-NMR (CDC1 3 6 2.55 2x CH 3 3.66; 3.77 OCH 3 isomer 3.71; 3.82 OCH3; isomer 5.04 CH 2 isomer 5.05 CH,; isomer 7.03 7.65 aryl- H; =CH).
The following compounds can be prepared in a corresponding manner.
r 0 0 a a a a a O.Z. 0050/43197 Table 1 No. R1 R 3 phys. data 1.1. H H CF 3 1.2. H CF 3
CE;
1.3. H CF 3 Phenyl 1.4. H CN Methyl H CN Ethyl 1.6. H CN n-Propyl 1.7. H CN iso-Propyl 1.8. H1 CN n-Butyl 1.9. H CN sec.-BUtyl 1.10. H CN tert.-BUtyl 1.11. H CN Cyclopropyl 1.12. H CN ICyclohexyl a, a S a a S a a .5 O.Z. 0050/43197 No.~ 'Ri JR plays. data 1.13. H CN M~ethoxymethy1 1.14. H CN Ethoxyrnethyl 1.15. H CN Phenoxymethyl 1.16. H CA3-Chiorophenoxymethyl 1.17. H ON Benzyloxymethyl 1118. H CN 2 -Methylbenzyloxymethyl (1.19. H NMtytim hl 112. H CN Phe-nylthiomethyl 1.21. H CN Ethynyl 1.22. H CN Phenylethynyl 1.23. H CN 1-Propynyl 1.24. H CN ON 1.25. H ON Acetyl 1.26. H CN Propion-1-yl 1.27. H ON Butyr-l-yl 1.28. H CN iSo-Butyr-l-yl 1.29. TH ONj~laoy 1.30._tH ON IBenzovl 1.31. IH ON f4-Chlorobenzoyl_____________ 1.32. HCN fBenzylcarbonyl__ 1.3. H ON Methoxycarbonyl 1.33ON ethoxycarbonyl S **S S S S S S S S S SO S *5 S 555 O.Z. 0050/43197 No. RlR R phys. data 1.35. H CN n-Propoxycarbonyl 1.36. H CN iso-Propoxycarbonyl 1.37. H CN n-Butoxycarbonyl 1.38. H CN is-utxcarbonyl 1.39. H CN sec.-Butoxycarboniyl 1.40. H CN tert.-Butoxycarbonyl 1.41. H CN n-Hexoxycarbonyl 1.42. H CN Phenoxycarbrlyl 1.43. H CN 4-Chiorophenoxycarbonyl 1.44. H CN Benzyloxycarbonyl 1.45. H CN Aminocarbonyl 1.46. H CN Dimeth-ylamiriocarbonyl 1.47. H CN Diethyiaminoczarbonyl 1.48. H CN Di-isopropylaminocarbonyl 1.49. H C14Phenylaminocarbonyl 1.50. H CN N-M4etby1 -N-Phenylaminocarbonyl 1.51. H CN Phenyl 1.52. H CN 2-Fluorop--nyl E/Z 8(CH_) 5.00 or 5:08 H CN 3-Fluorophenyl 8(CH-) =5.07 or 5.10 1.54. H CN 4 -Fluorophenyl I =5.05 1.55. H CN Pentafluorophenyl 0* 0** 0 0 *0e O.Z. 0050/43197 No. RI R-R phys. data 1.56. H CNt'-Chlorophenyl ~E/z 8(cH =4.95 oi 5.05 1.57. H }cN 3-Chlorophenyl .E!Z 8(CH_) 4.07 or 1.58. H CN 4-Chilorophenyl L5(CH 5.06 1.59. H CN Pentachiorophenyl 1.60. H CN 2,3-Dichlorophenyl 1.61. H CN 2.4-Dichiorophenyl EIZ 8(CH.) 4.98 or 5.08 1.62. 1H CN 2,5-Dichlorophenyk1 1.63. H CN 2,6-Dichlorophenyl EIZ 8(CH.) 4.98 or 5.09 1.64. H CN 11.4-Dich-'orophenyl EIZ 8 (CHI 5.09 or 5.11 1.65. H CN 1.66. H CN 2,3,4-Trichiorophenyl 1.67. H CN 2,3,5-Tiichlorophenyl 1. 68. H CN 12,3_6-Trichiorophenyl 1.69. H CN J2,4, 1.70. H CN 2,4,6-Tr"-hlorophenyl 1.71. IH CN 3,4,5-Trichior~ophenyl 1.72. H CN 2,3,4, 6-Tetrachlcrrophenyl 1.73. H CN 2,3,5..6-Tetrachlorophenyl 1.74. H CN 2-Bromophenyl 1.75. H CN 3-B-1romophenyl 1.76. IH I CN 4-Bromophenyl I b(CH) 5-09 a a. a a a a a..
a a a *a o.z. 0050/43197 No. RR-Rphys. data 1.77. 1H CN 2,4-Dibromoplienyl IH CN3-Bromo-4--Pluorophenyl 1.79. H CN 3-Bromo-4-Methoxyphenyl 1.80. H CN 2-Iodophenyl 1.81. (H IT 3-lodophenyl 1.82. H CN 4-Iodophenyl 1.83. P~ CN 2-Chloro-4-fluorophenyl 1.84. H CN 1.85. H CN 2-Chloro--6-fluorophenyl 1.86. H CN 2-Chloro-4-bromophenyl 1.87. H CN 2-Bromo-4-chlorophenyl 1.88. H CN 2-Bromo-4-fluorophenyl 1.89. H CN 3-Bromo-4-fluorophenyl 1.90. H CN 3-Chloro-4-fluorophenyl 1.91. H CN 3-Fluoro-4-chlorophexyl 1.92. 1H C N 2-Cyanophenyl 1.93. H CN 3-Cyanophenyl 1.94. H CN 4-Cyanophenyl 1.95. H CN 2-Nitrophenyl 1.96. H CN 3--Nitrophenyl 11.97. H CN 4-Nitrophenyl 11.98. 1H CN 12-Methyiphenyl f 83 **9 9~ 9 0* a 9 999 9 *09 9999999 9 *99. 9 9 9* 9 9 o.Z. 0050/43197 No. RlR -phys. data 1.99. H ON 3-Methyiphenyl b(CH-) 1.100. H ON 4-Methylphenyl E/Z 8(CH.) 5.04 or 5.05 1.101. H ON 2,4-Dimethylpheny.± 1.102. H CN 2,6-Dimethylphenyl 1.103. H ON 3,4-Dimethylphenyl 1.104. H ON 1.105. H ON 2,3,4-Trimethylphen-yl 1.106. H ON 2,3,5-Trimethylphenayl 1.107. H ON 2,3,6-Trimethylphenyl 1.108. H ON 2,4,5-Trimethylphen"1, 1.109. H O1, 2,4.6-Trimethylphenyl 1.110. H ON 3,4,5-Trimethylphenyl 1.111. H ON Pentamethyiphenyl 1.112. H ON 2-Ethyiphenyl 1.113. H ON 3-Ethylphenyl 1.114. H ON 4-Ethyiphenyl 1.115. H ON 1.116. H ON 2-n-Propylphenyl 1.117. H ON 3-n-Propylphenyl 1.118. H ON 4-n-Propylphenyl 1.119. H ON 2-iso-Propyiphenyl 1.120. 1H OCN 3-iso-Propylphenyl *9* a p a C
S..
p C P p *sp S p a a a a a p. ap p a. C *54 C o.Z. 0050/43197 fNo. RiR R3 phys. data 1.121. H CN 4-iso-Propylphenyl 1.122. H CN 2,4-Di--isopropylpheny1 1.123. H CN 1.124. H CN 4-n-Butyphenyl 1.125. H CN 4-sec.-BUtylphenyl 1.126. H CN 4-iSo-Butyiphienyl 1.127. H CN 4-tert.-Butylphe-nyl 1.128. H CN 3-tert.-Butylphenyl 1.129. H CN 2-tert.-Butylphenyl 1.130. H CN 2,4-Di-tert.-Butylphenyl 1.131. H CN 1.132. H CN 4-n-Hexylphenyl 1.133. H CN 4-n--Dodecylphenyl 1.134. H CN 2-Methyl-4--tert.--Butylphenyl 1.135. H CN 2-Methyl--6-tert.-Butylphenyl 1.136. H CN 2-methyl--4-isopropylphenyl 1.137. H CN 2-Methyl--4-Cyclohexylphenyl 1.138. H CN 2-Methyl-4-Phenylphenyl 1.139. H CN 2-Methyl-4-Benzylphenyl 1.140. H CN 2-methyl-4-Phenoxyphenyl 1.141. H CN 2-Methyl-4-Benzyloxyphenyl 1.142. IH CN 12-Methyl-3-Chlorophenyl S S S S O.Z. 0050/43197 No. R!R-'R phys. data 1.143. H CN 2-Methyl-4-Chlorophenyl 1.144. H CN 1.145. H CN 2-Methyl--6-Chlorophenyl 1.146. H CN 2-Methyl--4-Fluorophenyl 1.147. H CN 2-Methyl--3-Bromophenyl 1.148. H CN 2-Methy1-4-Bromophenyl 1.149. H CN 2-Methyl--3-Methoxyphenyl 1.150. H CN 2-Methyl-4-Methoxyphenyl 1 1 5 1 H C N 2 M e t h y l M t o y p e y 1.152. H CN 2-Methyl-6-Methoxyphe-nyl 1.153. H CN 2-Methyl-6-isoprooxyphenyl____________ 1.154. H CN 2-Methyl-4,-i ethopxyphenyl 1.155. H CN 2-Methoyphenyletoxphny 1.156. H CN 3-Methoxyphenyl 1.157. H CN 4-Methoxyphenyl 1.157. H CN 2,-DiMethoxyphenyl 1.159. H CN 2,4-Dimethoxyphenyl 1.160. H CN -Dimethoxyphenyl 1.161. H CN 1.162. H 3N ,4-Dimethoxyphenyl 1.163. H CN 1 .164. H CN 3,6-Dimnethoxyphenyl a. a a a O.Z. 0050/43197 No. RR phys. data 1.165. H CN 2,3,4-Trimethox-yphel 1.166. H CN 2,3,5-Trimethoxyphenyl 1.167. IH CN 2,3,6-Trimethoxyphelyl 1.168. H CN 2,4,5-Triffiethoxyphelyl 1.169. H CN 2,4, 6-Trimethoxyphelyl IiM0 H CN 3,4,5-Trimethoxyphell 1.171. H CN 2-Ethoxyphenyl 1.172. H CN 3-Ethoxyphenyl 1.173. H ICN 4-Ethoxyphenyl 1.174. H }CN 2-isopropoxyphenyl 1.175. H CN 3-isopropoxyphelyl 1.176. H CN 4-isopropoxyphelyl 1.177. H CN 3-tert.-Butoxyphefll 1.178. H CN 4-tert.-Butoxyphell 1.179. H CN 2-Trifluoronethoxyphell 1.180. H CN 3-Trifluoromethoxyphell 1.181. H CN 4-Trifluoromethoxyphelyl 1.182. H CN 3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl 1.8.H CN 4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl 1.8.H CN 2-Chloromethyiphelyl *.e
S
S S #55 S S S S S S S S S. S o.Z. 0050/43197 No. R, R- phys. data 1.185. H CN 3-Chioromethyiphenyl 1.186. H CN 4-Chioromethylphenyl 1.187. H CN 2-Trifluoromethyiphenyl 1.188. H CN 3-Trifluoromethyiphenyl 1.189. H CN 4-Trifluoromethylphenyl 1.190. H CN 2- (Methoxyiminomethyl)phenyl 1.191. H CN 3- (Methoxyiminomethyl)phenyl 1.192. H CN 4-(Methoxyiminomethyl)phenyl 1.193. H- CN 2-(Ethoxyiminomethyl)phenyl 1.194. H CN 3-(Ethoxyiminomethyl)pheny.
1.195. H CN 4-(Ethoxyixninomethyl)phenyl 1.196. H CN 2- (n-Propoxyiminomethyl)pheiyl 1.197. H CN 3- (n-Propoxyiminomethyl)phenyl 1.198. H CN 4- (n-Propoxyiminomet-hyl)phenyl 1.199. H ICN 2- (iso-propoxyiminornethyl)phenyl 1.200. H CN 3-(iso-Propoxyiminomethyl)phenyl 1.201. H CN 4-(iso-Propoxyiminomethyl)phenyl 1.202. H CN 2- (n-Butoxyirninomethyl)phenyl 1.203. H CN 3-(n-Butoxyiminomethyl)phenyl 1.204. H CN 4-(n-Butox-Yiminomethyl)phenyl 1-205. H CN 2-(iso-Butoxyirninomethyl)phenyl 1.206. H CN 3-Ciso-Butoxyiminomethyl)phenyl a a a.
a.
a..
a e a a a a a a a a a a a a a a a. O.Z. 0050/43197 No. R -R-'phys. data T.207. H CN 4-(iSo-ButoxyimiLnornethyl)phenyl 1.208. H CN 2-(tert.-Butoxyiminomethyl)phenyl 1.209. H CN 3-(tert.-Butoxyiminometnyl)phenyl 1.210. H CN 4-(tert.-Butoxyiminomethyl)phenyl 1.211. H CN 2- (n-Pentoxyiminomethyl)phenyl 1.212. H CN 3- (n-Pentoxyiminomethyl)phenyl 1.213. H CN 4-(n-Pentoxyiminomethyl)phenyl 1.214. H CN 2-(n-Hexoxyimiriomethyl)phenyl 1.215. H CN 3- (n-Hexoxyirninomethyl)phenyl 1.216. H CN 4- (n-Hexoxyiminomethyl)phenyl 1.217. H CN 2-(Allyloxcyiminomethyl)phenyl 1.218. H CN 3-(Allyloxyiminoinethyl)phenyl 1.219. 11. CN 4-(Allyloxyiminomethyl)phenyl 1.220. H CN 2- (Benzyloxyiminomethyl)phenyl 1.221. H CN 3- (Benzyloxyiminomethyl)phenyl 1.222. H CN 4-(Benzyloxyiminomethyl)phenyl 1.223. H CN 2- (Methoxyimino-1 '-ethyl)phenyl 1.224. H CN 3-(Methoxyimino-1'-ethyl)phenyl 1.225. H CN 4-(Methoxyimino-1'-ethyl)phenyl 1.226. H CN 2-(Ethoxyimino-l'-ethyl)phenyl 1.227. H CN 3-(Ethoxyimino-1'-echyl)phenyl 1.228. H CN .4-(Ethoxyirntino-1'-ethyl)phenyl a a..
a a a a a a. a o.z. 0050/43197 No. JR1 R3 phys. data 1.229. H CN 2-(n-Propoxyimino-1'-ethyl)phenyl 1.230. H CN 3-(n-Propoxyimino-1'-ethyl)phenyl 1.231. H CN 4- (n-Propoxyimino-1'--ethyl)phenyl 1.232. H CN 2-(n-Butoxyamino-1'-ethyl)phenyl 1.233. H CN 3- (n-Butoxyamino-1'-ethyl)phenyl 1.234. H CN 4- (n-Butoxyamino-1' -ethyl)phenyl 1.235. H CN 2-(n-Pentoxyimino-1'-ethyl)phenyl 1.236. H CN 3- (n-Pentoxyimino-1 '-ethyl)phenyl 1.237. H CN 4- (n-Pentoxyimino-1'-ethyl)phenyl 1.238. H CN 2-(n-Hexoxyimino-1'-ethyl)phenyl 1.239. H CN 3-(n-Hexoxyimino-1'-ethyl)phelyl 1.240. H CN 4- (n-Hexoxyimino-1'-ethyl)phenyl 1.241. H CN 2- (Allyloxyimino-1'-ethyl)-phenyl 1.242. H CN 3- (Allyloxyimino-1' -ethyl)-phenyl 1.243. H CN 4- (Allyloxyimino-1'-ethyl)-phenyl 1.244. H CN 2-(Benzyloxyimino-1'-ethyl)phenyl 1.245. H CN 3-(Benzyloxyimino-1'-ethyl)phenyl 1.24 6. H CN 4- (Benzyloxyiminco-1'-ethyl)phenyl 1.247. H CN 2-Phenyiphenyl 1.248. H CN 3-Phenylphenyl 1.249. H CN 4-Phenyiphenyl 1.250. H CN 2-Phenoxyphenyl
U
UO*
*U
U U* 0 *0 0* O.Z. 0050/43197 No. phys. data 1.251. H GN 3-Phenoxyphenyl E/Z 8(CH-) 5.04 or 5.06 1.252. H CN 4-Phenoxyphenyl 1.253. H CN 2-Denzyloxyphenyl 1.254. H CN 3 -Benzyloxyphenyl 1.255. H CN 14-Benzyloxypheny.
1.256. H CN 4-(Imidazol-1'-yl),phenyl 1,257. H CN 4-(Piperaziri-1'-yl)phenyl 1.258. H CN 4-(Morpholin-1'-yl)phenyl 1.259. H CN 4-(Piperidin-1'-yl)phenyl 1.260. H CN 4-(Pyridyl-2'-oxy)phenyl 1.261. H- CN 2-Cyclopropylphenyl 1.262. H CN 3-Cyclopropylphenyl 1.263. H CN 4-Cyclopropyiphenyl 1.264. H CN j3-CyclohexylphenyJ.
1.265. H CN 4-Cyclohexylphenyl 1.266. H CN 74-Oxiranyiphenyl 1.267. H CN 4-(1',3'-Dioxan-2'-yl)-phenyl 1.268. H CN 4- (Tetrahydropyran2-yloxy) -phenyl 1.269. H CN 1-Naphthyl 1.270. H CN 2-Naphthyl 1.271. H CN Benzyl 1.72.I H CN 12-Methylbenzyl *5 S S S S S S C S S S S S 55 5*5 S o.z. 0050/43197 No. RIR 2
R
3 phys. data 1.273. H CN 3-Methylbenzyl 1.274. H CN 4-Methylbenzyl 1.275. H CN 4-tert.--Butylbenzyl 1.276. H CN 2-Chlorobenzyl 1.277. H CN 3-Chlorobenzyl 1.278. H CN 4-Chlorobeizy1 1.279. H CN 2,4-Dichlorobenzyl 1.280. H CN 2,6-Dichlorobenzyl 1.281. H CN 2,4,6-Trichlorobenzyl 1.282. H CN 2-Trifluoromethylbenzyl 1.283. H CN 3-Trifluoromethylbenzyl 1.284. H- CN 4-trifluoroniethylbenzyl 1.285. H CN 2-methoxybenzyl 1.286. H CN 4--methoxybenzyl 1.287. H CN 4-tert.-Butoxybenzyl 1.288. H CN 1-Phenoxybenzyl 1.289. H- CN 1-Phenethyl 1.290. H CN 2-Phenethyl 1.291. H CN 1-Phenylpropyl 1.292. H CN 2-phenylpropyl 1.293. H CN 3-Pheinylpropyl 1.294. H __jN 12-Methyl-2-phenylpropyl *0* *a hJ 9 9 9 99 9 9 9 *99 9 O.Z. 0050/43197 1 No. RR2R 3 phys. data 1.295. H CN 2-Methyl-3-pheflylpropyl_____________ 1.296. H CN 4-Phenylbutyl 1.297. H CN 2-Pheny1-l-ethefl 1.298. H CN 1-Phenyl-1-ethenyl 1.299. H CN 1-Phenyl-1-propelyl 1.300. H CN 1-Phenyl-l-propef- 2 -yl 1.301. H CN 2,2-Diphenylethelyl 1.302. H CN 2-Pyridyl 1.303. H CN 3-Pyridyl 1.304. H CN 4-Pyridyl 1.305. H CN 2,6-Pyrimidinyl 1.306. H CN 1.307. H CN 2- rhienyl 1.308. H CN 3-Thienyl 1.309. H CN 2-Furyl 1.310. H CN 3-Furyl 1.311. H CN 1-Pyrrolyl 1.312. H CN 1-ImidazoJ-yl 1.313. H CN 1,2,4-Triazolyl 1.314. H CN- 1,3,4-Triazolyl 1.1.H CN 4-Thiazolyl 1.16 CN 2-Befizothiazolyl a p *0 p. fl050/43197 [No. JRI R-1R3 phys. data 1.31-J H CN 2-Pyridylmethyl______________ 1l.31S.' H CN 3-Pyridyirnethiyl '1.319.tH CN 1.320. H CN 2'-Thienyl-2-ethelyl____________ 1.321. H CN 3'-Pyridyl-2-ethenyl 1.322. 1H CN Oxirarnyl 1.323. IH CN IiAiiiy 1.324. IH teN 1-Azetidiny1
I
1.325. 'H TeN 1--Pyrrolidinyl 11.326. H CN2-Tetrahydrofurylf_____________ 1.327. H 1 CN 2-TetrahydrOrTyralyl_____________ 1.328. H ICN 3 -Tetrahydropyranyl 1.329. H leN 1-Piperidinyl 1.330. H CN 1-morpholiflyl 1.331. H CN 1-Piperazinyl 1.332. H CN 1,3-Dioxan-2-yl 1.333. H CN 4-Tetrahydrothiopyrall 1.334. H CN 4-Methylpeit-3-efl-1-yl 1.335. H JCN 2-Propenyl 1.336. H ICN 2-Butenyl 1.337. H t '1-Methyl-2-propelyl 1.,338. [H eN 3-Methyl-2-butenylI C C a Ceo .00 C a SC.
0.0.04. C C S S C 0e 0 S C S S S *o O.z. 0050/43197 No. JRI JRR3 jphys. data 1.339._IH JCN 2-Di'fluorethenylT 1.340. H CN 2 -Dichioroothenyl 1.341. H CN 33--rfurpoey 1.4.HCN 1333-Tri chiorooDrop enyl 1.343 H CN3-Chloro-2-propenyl 1.4.HCN cyclopent-l-eqryl 1.4.HCN Cyclopentadienyl 1.4.HCN Cycl1ohex- 1-enyl 1.347 H CNPentafluorocyclopentadienyl 1.348. H CN Pentachlorocyclopentadienyl 1.350. H CO 2 Me Phenyl 126 -1300C 1.351. H CO 2 Me 2-Fluorophenyl 1.352. H CO 2 Me 3-Fluorophenyl 1.353. H CO-,Me 4-Fluorophenyl 1.354. H CO 2 Me' 2-Chlorophenyl bC-) 49 1.355. H COzMe 3-Chiorophenyl 1.356. H C0 2 ML: 4-Chlorophenyl 1.357. H CO 2 Me 2-Methyiphenyl 1.358. H CO 2 ,Me 3-?Aethylphenyl 5(H) 4 1.359. HR Co&.Me 4-Mathyiphenyl 1.360. IH CO 2 ,Me 2-Cyanophenyl .6* o *0* 9 SS *e o.z. 0050/43197 JR R 2 l R3 IlihTs. data S1. 361. 1IH 1.362. H 1.363. H 1.6 H 71.365. H 1.36L,. H 1. 367., H 1.368. H 1.369. H 1.370. Hi 1.371. H 1.372. H 1.373. H 1.374. H 1.375. H 1.376. H 1.377. H 1. 378. H Canph-y 'Co 2 me 4 4-Cyanophenyl
CO
2 Me j2--Methoxyphenyl_____________
CO
2 Me !3-methoxyphenyl CO-!Me 4-methoxyphenyl
CO
2 Me 2-Nitrophenyl CO2Me 3-Nitrophenyl
CO
2 Me 4-Nitrophernyl LP(rn(O~e) 2 Phentyl 2 2-Fluorophenyl 3-Fluorophenyl P(O) (MeiV 4-Fluorophenyl P(O) (OMe)2 2-Chiorophenyl P(O) (OMe) 2 3-Chiorophelyl P (Oie-) 2 4-Chiorophenyl P (Oe) 2 2-Methyipheniyl P(O) (O~e) 2 3-Methyiphenyl 107 0
C
P (OMe) 2 4 -Methy lphepy 1 1.379. CH 3 CN Phenyl 1.380. Acetyl H 26Dclrpey 1.381. AcetyI H 2,4-Dichlorophenyl 1.382. ICH 3
CO
2 Et Benizoyl 000 0 0 0 000 O.Z. 0050/43197 No. R 2 R3 phys. data 1.383. fmethoxycar- H AcetylI [bonylmethyl 1.404._[H LIC0 2 Me [2-Bromophenyl 97_- 102 0
C
O.Z. 0050/43197 O.Z. 0050/43197 No. 0 R2phys. data 1.388 0 0
CH
00 0 0 1.389 0 C(H 2 H349 1.390_ CC 8C13 51 0* C C *C*
C
C C C CC* C C C C. 'A CCC C o.z. 0050/43197 0 c 0 a..
a a a O.Z. 0050/43197 a a
S
a a a a. a Iphys. data No.
1<R 3 1.395 0 0 H 0 1.396 N-OEt
ICH
0
N
1.397 N-OEt CH3 CH2 %*0 0 00 00 000 0 0 0 **0 00*000 0 0 0 0 0 00 0 0 000 0 0 0 0o 0 000 000 0 O.Z. 0050/43197 No. 0 R 2 phys. data 1.398 0 =0 CH H3 0
N-
CH3H a..
a a a a. a a a a a a a a a..
O.Z. 0050/43197 No. 0 R 2 phys. data 1.4010 N-NCj
CH
3 1.402 -0 H 154 15511C 0 1.403 -o H 149 1500C /0
CH
3 *5 a a *5* *5 B. B 5555.55 0 S *5e* S a SS See O.Z. 0050/43197 Table 2 0
R
OMe R CO )Me N No. R1R 3phys. data 2.1. H H CF 3 2.2. H CF 3
CF
3 2.3. H CF3 Phenyl.
2.4. H CN Methyl H CN Ethyl 2.6. H CN n-Propyl 2.7. H CN isopropyl 2.8. H CN n-Butyl 2.9. H CN sec.-Butyl 2.10. H CN tert.-Butyl 2.11. H CN Cyclopropyl 2.12. IH CN Cyclohexyl
S
CS
S~ 555 S S
S
*5 o.Z. 0050/43197 S S S S S SS S S S S S 5555 i S S 55 5 555 55* 5 No. PiR phys. data 2.13. H CN Methoxyiethy- 2.14. H CN Ethoxyrnethyl 2.15. H- CN Phenoxymethyl 2.16. H CN 3-Chlorophenoxymethyl 2.17. H CN Benzyloxymethyl 2.18. H CN 2-Methylbenzyloxyrnethyl 2.19. H CN Methylthiomfethyl 2.20. H CN Phenyithiomethyl 2.21. H CN Ethynyl 2.22. H CN Phenylethynyl 2.23. H CN 1-Propynryl 2.24. H CN CN 2.25. IH CN ACetyl 2.26. H CN Propion-l-yl 2.27. H CN 1 Butyr-1-yl 2.28. H CN Iisobutyr-1-XT 2.29. H CN Pivaloyl 2.30. H CN Benzoyl 2.31. H CN 4-Chlorobenzoyl 2.32. H ICN Benzylcarboflyl 2.33. H CN Methoxycarboflyl 12.34. H CN Ethoxycarbonyl
S
S. S
S
55
S.
S**
5 0 S a S S *~S S S S S
S
S* 5.5 O.Z. 0050/43197 No. RR-R 3 phys. data 2.35. H CN ns-Propoxycarbonyl 2.36. H CN is-Prpoxycarbonyl 2.37., H CN n-obutoxycarbonyl 2.38. H CN so.Butoxycarbonyl 2.39. H CN tert.-Butoxycarbonyl 2.40. H CN t-et-xoxycarbonyl 2.41. H CN n-heoxycarbonyl 2.42. H CN P-hohenoxycarbonyl 2.44. H CN Benzyloxycarbonyl 2.45. H CN Aminocarbonyl 2.46. H CN Dimethylaminocarbonyl 2.47. H CN Diethylaminocaribonyl 2.48. H CN Di-isopropylaminocarbonyl 2.49. H 1 CN Phenylaminocarbonyl 2.50. H JGN N-Methyl-N-Phenylamrinocarbonyl 2.51. H -N Phenyl E/Z 6(MH) 4.98 or 5.00 2.52. B. fCN 2-loophenyl 107 108-C 2.53. H JCN 3Fuorophenyl 97 98-C 2.54. H CN 4Fuorophenyl 128 131 C 2.55. H CN na f luorophenyl H CN 2-hoohnlEIZ b(CH.) 4.90 or .0 9 9 S 95
S..
S S. S S *5 *S
S**
545595. S .5 9 S S 0 5 *9 S o.Z. 0050/43197
S
No. RR1R3phys. data 2.57. H CN 3-Chioropherlyl E/Z 8 (CH 2 5.02 or 5.05 2.58. H CN 4-Chloropheiyl b(CH) 5.02 or 5.03 ~2.59. IH CM Pentachioropheny- 2.60. H CN 2,3-Dichlorophenyl 2.61. H CN 2,4-Dichiorophelyl E/Z b(CH.) =4.93 or 5.03 2.62. H CN 2.63. H CM 2, 6-Dichlorophenyl 2.64. H CN 3,4-Dichiorophenyl 121 -122,C 2.65. 1H CN 3, 2.66. ,H CN 2,3,4.-Trichiorophelyl 2.67. H CN 2,3,5-Trichlorophelyl 2.68. H CM 2,3,6-Trichlorophelyl 2.69. H CN 2,4,5-Tr-ichlorophelyl 2.70. 1H CM 2,4,6-Trichlorophenyl 2.71. H CN 3,4,5-Trichlorophelyl 2.72. H CM 2,3,4,6-Tetrachlorohell 2.73. H CN 2.3,5,6-Tetrachlorophenll 2.74. H CN 2-Bromopheny1 2.75. H CM 3-Bromophenyl 2.76. H CN 4-Bromophenyl 100 -102 C 27. H CM 2,4-Dibromophelyl ft .ft. ft.
ft..
ft..
ft ft ft. ft ft ft ft.. ft ft ft ft..
ft ft ft ft ft ft ft 5ftft ft ft ft ft ft ft *ft- ft ftt~ft ftftft ft OftZ. 0050/43197 No. RR"Rlphys. data 2.78. H CN 3-Brorno-4-fluorophenyl 2.79. H CN 3-Bromo-4-Methoxyphelyl 2.80. H CN 2-Iodophenyl 2.81. H CN 3-Iodophenyl 2.82. H CN 4-Iodophenyl 2.83. IH CN 2-Chloro-4-fluorophelyl 2.84. H CN 2.85. H CN 2-Chloro-6-fluorophelyl EIZ 6(CH- 4.94 or 5.04 2.86. H CN 2-Chloro-4-bromopheriyl 2.87. H CN 2-Bromo--4-chlorophelyl 2.88. H CN 2-Bromo-4.-fluoropheill 2.89. H CN 3-Bromo-4--fluoropheflyl 2.90. H CN 3-Chloro-4-fluorophelyl 2.91. H CN 3-Fluoro-4-chlorophell 2.92. H CN 2-Cyanophenyl 2.93. H CN 3-Cyanophenyl 2.94. IH CN 4-Cyanophenyl 2.95. H CN 2-Nitrophenyl 2.96. H CN 3-Nitronhenyl 2.97. H CN 4-Nitrophenyl 2.98. IH CN 2-methyiphenyl 106 107 C 299. IH CN 3-Methyiphenyl 129 130-C C
A
a.
S.
a tSp a- a we a 9 a. a.
0050/43197 No. RRR3phys- data 2.100. H 4 -Methyiphenyl 93 2.101. hl CN 24Dirnethylpheflyl 2.102. H FN2,4-iehypey 2.103. H CN 3,4-Dimethylphenyl_____________ 2.104. H CN 2.105. H CN 2,3,4-Trimethylphenyl 2.106. H CN 2,3,5-Trimethyiphenyl 2.107. H CN 2,3,6-Trimethyiphenyl 2.108. H CN 2,4..5-Trimethylphenyl 2.109. H CN 2,4, 6-Trimethyiphenyl 2.110. H CN 3,4,5-Trimethylphenyl 2.111. H CN Pentar :-tlylphenyl 2.112. H CN 2-Ethyiphenyl 2.113. H CN 3-Ethylphenyl 2.114. H CN 4-Ethylphenyl 2.115. H CN 3,ca-Diethylphenyl 2.116. H CNi 2-n-Pzopylpheny1L 2.117. H CN 3-n-Propylphenyl 2.118. H Cri 4-n-Propylphenyl 2.119. H 2-isopropyiphenyl 2.120. 1H CN 3-isopropyiphenyl 2.121. IH CN 14-isopropylpb-.nyl a. a a.
a.
a a.
a..
a a a a a. a a a a *aa a. a. a. a a a a a a a. a a S a a a. a a a. a a O.Z. 0050i43197 No. R R 1 R3 phys- data 2. 12 2. H CN 2,4-Di-isopropylphenyl 12 .123. H CN 1 2.124. H N4nBtpey 2F125. H CN 4-sec.-Butylphenyl 2.126. H CN 4-isobutyiphenyl 2.127. H CN 4-tert.-Butylphenyl____________J K2.128. H CN 3-tert.-Butylphenyl 2.129. H CM 2-tert--Butylphenyl 2.130. H CN 2,4-Di-tert.-Butylphenyl 2.131. H CN 2.132. H CN 4-n-Hexylphenyl 2.133. H CN 4-n-Dodecylphenyl 12,3134. H CN 2-Methyl-4-tert butyiphenyl F2-.'35. H CM 2-methyl-6-tert.-butylphenyl______________ 2.136. H CN 2-Methyl-4-isopropylphenyl 2.3.HCN 2-Methyl-4-cyclohexylphenyl 2.138. H CM 2-Methyl-4-phenylphenyl 2.139. *H CM 2-Methyl-4-benzylphenjil 2. 140. H CM 2-Methyl-4-phenoxyphenyl 2.141. H CN 2-Methy1-4-benzylox-yphen)?l 2.142. H CM 2-Methyl-3-chlorophenyl 2.143. JH CN2Mtyl- 4-chlorophenyl____ *a a a a a a a O.Z. 0050/43197 No. RR-R"phys. data 2.144. H CN 2-methyl-5-chlorophell______ 2.145. H CN 2-Methyl-6-chlorophell___________ 2.146, H CN 2-methyl-4-fluorophell____________ 2.147. H CN 2-Methyl-3-bromnophenyl 2.148. H CN 2-Methyl-4-bromopheiyl 2.149. H CN 2-Methyl-3-methoxyphelyl___________ 2.150. H CN 2-Methyl-4-methoxyphell___________ 2.151. H CN 2.152. H CN 2-methyl-6-methoxyphenll 2.153. H CN 2-Methyl-4-isopropoxyphell_____________ 2.154. H CN 2-Methyl-2,5-dimfethoxypheflyl_____________ 2.155. H CN 2-Methoxyphenyl 2 156. H CN 3-methoxyphelyl 2.157. H CN 4-Methoxyphel 2.158. H CN 2,3-Dimethoxyphelyl 2.159. H CN 2,4-Dimethoxyphelyl 2.160. H CN 2.161. H CN 2,6-DimethoxyphenYl 2.162. H CN 3,4-Dimethoxyphell 2.163. 1H CN 2.164. 11 CN 3,6-Dimethoxyphell 2.165._j H CN 2,3,4-Trimethoxyphelyl______________ C C C C C C p. O.Z. 0050/43197 NO. Rl R 3 phys. data 2.166. H CN 2,3,5-Trimethoxyphenyl 2.167. H CN 2,3, 6-Trimethoxyphenyl 2.168. H CN 2,4,5-Trimethoxyphenyl 2.169. H CN 2,4,6-Trimethoxyphenyl 2.170. H CN 3,4,5-Trimethoxyphenyl 2.171. H CN 2-Ethoxyphenyl 2.172. H CN 3-Ethoxyphenyl 2.173. H CN 4-Ethoxyphenyl 2.174. H CN 2-isopropoxyphenyl 2.175. H CN 3-isopropoxyphenyl 2.176. H CN 4-isopropoxyphenyl 2.177. H CN 3-tert.-Butoxcyphenyl 2.178. H CN 4-tert.-Butoxyphenyl 2.179. H CN 2-Trifluoromethoxyphenyl 2. 180. H CN 3-Trifluoromethoxyphenyl 2.181. H CN 4-Tritluoromethoxypheny.
2.182. H CN 3-(1',1',2',2'-Tetrafluoro)ethoxy- 2.183. H CN 4-(1',,1,2',2'-Tetrafluoro)ethoxy- 2.184. H CN 2-Chloromethyiphenyl 2.185. H CN 3-Chioromethyiphenyl a. a. a.
a a a a a a a a a. a o.z. 0050/43197 I phys. data 2.186. H CN 4-Chioromethyiphenyl 2.187. H CN 2-Trifluoromethyiphenyl 2.188. H CN 3-Trifluoromethylphenyl 2.189. H CN 4-Trifluoromethyiphenyl 2.190. H CN 2-(Methoxyiminomethyl)phenyl 2.191. H CN 3-(Methoxyiminomethyl)phenyl- 2.192. H CN 4-(IMethoxyiminomethyl)phenyl 2.193. H CN 2-(Ethoxyiminomethyl)phenyl 2.194. H CN 3- (Ethoxyiminomethyl)phenyl 2.9.RCN 4- (Ethoxyiininomethyl)phenyl 2.9.HCN 2- (n-Propoxyiminomethyl)phenyl 2.9.HCN 3- (n-Propoxyiminomethyl )phenyl 2.9.HCN 4- (n-Propoxyiminomethyl)phenyl 2.201. H CN 4- (isopropoxyiminomethyl)phenyl 2.202. H 2N (n-Butoxyimnometyl)phenyl 2.203. H C-N 2-(n-Butoxyimino-methyl)phenyl 2.204. H CN 3-(n-Butoxyimino-methyl)phenyl 2.204. H CN 2-(is-Butoxyimino-methyl)phenyl 2.206. H CN 3-(iso-Butoxyimino-methyl)phenyI 2.207. H CN 3-(iso-Butoxyirnino-methyl)phenyl
S
S *5 S *SS S **S S S S S S S S
S
S* O.Z. 0050/43197 No. JR12IR3 phys. data 2.208. H CN 2- (tert.-Butoxyimino-methyl)phenyl 2.209. H cIN 3-(tert.-Butoxyimino-methyl)phenyl 2.210. H CIN 4- (tert.-BUtoxyimino-methyl)phenyI 2.211. H C14 2- (n-Pentoxyiminomethyl) -phenyl 2.212. H CN 3- (n-Pentoxyiminornethyl)-phenyl 2.213. H CN 4- (n-Pentoxyiminornethyl) -phenyl 2.214. H CN 2- (n-Hexoxyiminomethyl) -phenyl 2.215. H CN 3- (n-Hexoxyiminomethyl) -phenyl 2.216. H CN 4-(n-Hexoxyiininomethyl)-phenyl 2.217. H CN 2-(Allyloxyiininomethyl)-phenyl 2.218. H CN 3-(Allyloxyimninomethyl)-phenyl 2.219. H CN 4- (A11yloxyiminomethy1) -pheniyl 2.220. H CN 2- (Benzyloxyiminomethyl) -phenyl 2.221. H CN 3-(Benzyloxyiminomnethyl)-phenyl 2.222. H CN 4- (Benzyloxyiminornethyl)-phenyl 2z~223. H CM 2- (Methoxyimino-1 '-ethyl) -phenyl 2.224. H CN 3-(Methoxyimino-1'-ethyl) -phenyl 2.225. H CN 4- (Methoxyimino-1'-ethyl) -phenyl 2.226. H CN 2- (Ethoxyimino-1'-ethyl) -phenyl 2.227. H CN 3- (Ethoxyimino-1 '-ethyl)-phenyl 2.228. H CN 4-(Ethoxyimino-1'-ethyl)-phenyl 2.229. H CN 2-(n-Propoxyimino-1'-ethyl)phenyl a a a a C, a a a a a a p. a O.Z. 0050/43197 No. RIR 2
R
3 phys. data 2.230. H CN 3- (n-Propoxyimino-1'-ethyljphenyl 2.231. H CN 4-(n-Propoxyimino-1'-ethyl)phenyl 2.232. H CN 2- (n-Butoxyamino-1'-ethyl)phenyl 2.233. H CN 3- (n-Butoxyanino-1'-ethyl)phenyl 2.234. H CN 4-(n-BUtoxyamino-1'-ethyl)phenyl 2.235. H CN 2-(n-Pentoxyimino-1'-ethyl)phenyl 2.236. H CN 3-(n-Pentoxyimino-1'-ethyl)phenyl 2.237. H CN 4-(n-Pentoxyimino-1'-ethyl)phenyl 2.238. H CN 2- (n-Hexoxyimino-1'-ethyl)phenyl 2.239. H CN 3-(n-Hexoxyimino-1'-eth.-yl)phenyl 2.240. H CN 4-(n-Hexoxyimino-1'-ethyl)phenyl 2.241. H CN 2- (Allyloxyimino-1'-ethyl)-phenyl 2.242. H CN 3- (Allyloxyimino-1'-ethyl)-phenyl 2.243. H CN 4-(Allyloxyimino-1'-ethyl)-phenyl 2.244. H CN 2- (Benzyloxcyimino-1'-ethyl)phenyl 2.245. H CN 3- (Benzyloxyimino-1'-ethyl)phenyl 2.246. H CN 4- (Benzyloxyimino-1'-ethyl)phenyl 2.247. H CN 2-Phenylphenyl 2.248. H CN 3-Phenylphenyl 2.249. H CN 4-Phenylphenyl 2.250. H CN 2-Phenoxyphenyl 2.251. jH JCN 3-Phenoxyphenyl 96 -97C a 4.* a a a.* Ca. a a a a a a. a a O.Z. 0050/43197 N. Rl 2R phys. data 2.252. H CN 4-Phenoxyphenyl 2.253. H CN 2-Benzyloxyphenyl 2.254. H CN 3-Benzyloxyphenyl 2.255. H CN 4-Benzyloxyphenyl 2.256. H CN 4-(Imidazol-1'-yl)phenyl 2.257. H CN 4-(Piperazin-1'--yl)phenyl 2.258. H CN 4-(Morpholin-1'-yl)phenyl 2.259. H CN 4-(Piperidin-1'-yl)phenyl 2.260. H CN 4-(Pyridyl-2'-oxy)phenyl 2.261. H CN 2-Cyclopropylphenyl 2.262. H CN 3-Cyclopropylphenyl 2.263. H CN 4-Cyclopropyiphenyl 2.264. H CN 3-Cyclohexylphenyl 2.265. H CN 4-Cyclohexylphenyl 2.266. H CN 4-Oxiranylphenyl 2.267. H CN 4-(1',3'-Dioxan-2'-yl)-phenyl 2.268. H CN 4-(Tetrahydropyran-2-yloxy)-phenyl 2.269. H CN 1-Naphthyl 2.270. H CN 2-Naphthyl 2.271. H CN Benzyl 2.272. H CN 2-Methylbenzyl 2.273. IH JCN 13-Methylbenzyl 0
S
*5
S
S 4 5 **S S S S
S
555 S S S 555 O.Z. 0050/43197 No. R3 2R 3 phys. data 2.274. H CN 4-Methylbenzyl 2.275. H CN 4-tert.-Butylbenzyl 2.276. H CN 2-Chlorobenzyl 2.7.HCN 3-Chlorobenzyl 2.7.HCN 4-Chlorobenzyl 2.7.HCN 2, 4-Dichlorobenzyl 2.8.1HCN 2 ,6-Dichlorobenzyl 2.8.HCN 2,4, 6-Trichlorobenzyl T8.HCN 2 -Trifluoromethylbenzy.
2.283. H CN 3-Trifluoromethylbenzyl 2.284. H CN 4-trifluoromethylbenzyl 2.285. H CN 2-Methoxybenzyl 2.286. H CN 4-Methoxybenzyl 2.8.HCN 4-tert. Butoxybenzyl 2.8.HCN 4-Phenoxybenzyl 2.8.HCN I-Phenethyl 2.290. H CN 2-Phenethyl 2.9.HCN 1-Phenyipropyl 2.9.HCN 2-Phenylpropyl 2.9.HCN 3-Phenylpropyl 2.9.HCN 2-Methyl-2-phenylpropyl LEI:iCN 12-Methyl-3-phenylpropyl 0 0
C
C *C
C
C
C
CC. C.* C. C C
C
*c C. C C C. C.C *CC C O.Z. 0050/43197 INo. 'Ri R2 R3phys. data 2.296. H CN 4-Phenylbutyl 2.297. H CN 2-Phenyl-1-ethenyl 2.298. H CN 1-Phenyl-1-ethenyl 2.299. H CN 1-Phenyl-l-propenyl 2.300. ,H CN 1-Phenyl-1--propen-2-yl 2.301. H CN 2,2-Diphenylethenyl 2.302. H CN 2-Pyridyl 2.303. H CN 3-Pyridyl 2.304. H CN 4-Pyridyl 2.305. H CN 2,6-Pyrimidinyl.
2.306. H CN 1, 2.307. Hf CN 2-Thienyl 2.308. H CN 3-Thienyl 2.309. H CN 2-Furyl 2.310. H CN 3-Furyl 2.311. H CN 1-Pyrrolyl 2.312. H CN 1-imidazolyl 2.313. H CN i,2..4-Triazolyl 2.314. H CN 1,3,4-Triazolyl 2.315. H CN 4-Thiazolyl 2.316. H CN 2-Benzothiazolyl 2.317. CN 2-Pyridylmethyl a. a a a a a. a.
a a *.a a a a a. a a a a a. a. a a. a a.a a O.Z. 0050/43197 No. RR2R 3 phys. data 2.318. H CN 3-Pyridylmethyl 2.319. H CN 2'-Furyl-2-etlefll 2.320. H CN 2'-Thienyl-2-ethell H CN 3'-Pyridyl-2-ethell 2.322. H CNOxiranyl 2.323. H CN 1-Aziridinyl 2.324.1H CN 1-Azetidinyl 12.325. H CN 1-Pyrrolidiiiyl S2.326. H CN 2-Tetrahydrofuryl 2.327. H CN 2-Tetrahydropyrall___________ 2.328. H CN 3-Tetrahydropyralyl 2.329. H CN 1-Piperidinyl 2.330. H CN 1-Morpholinyl 2.331. H CN I-Piperazinyl 2.332. IH CN 1,3-Dioxan-2-yl 2.333. H CN 4-Tetrahydrothiopyralyl 2.334. H CN 4-Methylpelt-3-efl-1-yl 2.335. H CN 2-Propeny.
2.336. 1H CN 2-Butenyl 2.337. IH CN I-Methyl-2-propell 2.338. H CN 3-Methyl-2-butelyl 2.339. H CN 2,2-Difluoroethelyl 0 a.
a a a a a a. a a **a a. a. *ea a a a a a a. a a a. .a a a SC a o.Z. 0050/43157 No. RiR 3phys. data 2.340. H CN 2,2-Dichloroethenyl 2.341. H CN 3,3,3-Trifluoropropenyl 2.342. H CN 3,3,3-Trichloropropenyl 2.343. H CN 3-Chloro-2-propenyl 2.344. H CN Cyclopent-1-enyl 2.345. H CN cyclorentadienyl 2.346. H CN Cyclohex-1-enyl 2.347. H CNPentafluorocyclopentadienyl 2.348. H CN Pentachiorocyclopentadienyl 2.349. H CN Styryl 2.350. H CO_ 2 Me Phenyl 124 -128 0
C
2.351. H CO 2 Me 2-Fluorophenyl 2.352. H CO 2 Me 3-Fluorophenyl 2.353. H CO 2 Me 4-Fluorophenyl 2-354. H CO 2 Me 2-Chiorophenyl t8(CH2) 4.90 2.355. H CO 2 Me 3-Chlorophenyl 2.356. H CO 2 Me 4-Chlorophenyl 2.357. H CO 2 Me 2-Methylphenyl 2.358. H CO 2 Me 3-Methylphenyl 8(CH2n) 4.87 2.359. H CO-Me 4-Methylphenyl 2.360. H CO:Me 2-Cyanophenyl 2.361. IH ICO 2 Me 3-Cyanophenyl
S..
S.
U
U 05 S *55 S S S 05 *S 0 S* S 550 5 O.Z. 0050/43197 No. RlR 3phys. data 2.362. H CO.-Me 4-Cyanophenyl 2.363. H COMe, 2-Methoxyphenyl- 2.364. H CO 2 Me 3-methoxyphenyl____________ 2.365. H CO 2 Me 4-Methoxyphenyl 2.366. H CO 2 Me 2-Nitrophenyl 2.367. H CO 2 Me 3-Nitropheny.
2.368. H COqMe 4-Nitrophenyl 2.369. H P(O)(Ome) 2 Phenyl 2.370. H P(O)(OMe) 2 2-Fluorophenyl 2.371. H P(O) (OMe) 2 3-Fluorophenyl 2.372. H P(Q)(Ome) 2 4-Fluorophenyl 2.373. H P(O)(OMe) 2 2-Chlorophenyl 2.374. H P(O) (OMe) 2 3-Chiorophenyl 2.375. H P(O)(OMe) 2 4-Chlorophenyl 2.376. H P(O) (OMe) 2 2-Methyiphenyl 2.377. H P(O)(OMe) 2 3-Methyiphenyl 135 -1370C 2.378. H P(O)(OMe) 2 4-Methyip~henyl 2.379. CH 3 CN Phenyl 8(CH 2 5.00 2.380. Acetyl H 2,6-Dichlorophenyl 2.381. Acetyl H 2,4-Dichloropheny1 2.382. ICH3 lCO-Et Benzoyl a.
a.
a a.. a a a a at at a a a baa a a a a a a a a a a a a. *a a a a a. a a O*Z. 0050/43197 No. R][2R 3 phys. data 2.383. Methoxycar- H AcetylI jbonyirnethyl 2.404. [H CO 2 Me 2-Promophenyl 192_- 93 0
C
a
S.
a S.
a a..
S. SaSa 0 S a S S a a a a a a a a. S *aa a o.Z. 0050143197 2.384 122 123C oz S S
S
S 50 C See
S
S
bC# C C a S.e.C. S 5 0 C CbCS S O.Z. 0050/43197 CH31 0o we.
we
C
Sc
C
S.
S C S C 0C C a S C* C C*S C C C CCC .CCw *WC C S C S S S* S S C C C. CS S o.z. 0050/43197 0.
2.392 2.393 NC N0 2 0
CH
3
CH
3 2.394 SS
S.
0 a a.
S *1 0. .0 p a p a. a p a p a S. as a a p a. a PaSO.. a O.Z. 0050/43197
-CH
3
CH
2 2.397
CH
3
CH-)
S
S S S
S.
S
*S
S 55 S *S* S S
S
S.C
S S S S 5. 0 5- 5
*S
**SSSS S S S S S S S S S S S S S S S S S. O.Z. 0050/43197 No. 0 R 2 phys. data 2.398 0
CH
3 H3
CH
3
H
2.400 -0
N-N
CH-3_ 5* S S S S S o.Z. 0050/43197 No. 0 R2 phys. data RR3 2.401 -0 N -N
CH
3
CH
3 2.402 -0 H 161 1620C 0 0 2.403 -0 H 171 172 0
C
N0
CH
3 a S a S O.Z. 0050/43197 01 Table 3 C0 2 Me No. R1R 3phys. data 3.1. H H CF 3 3.2. H CF 3
CF
3 3.3. H CF 3 Phenyl 3.4. H CN Methyl H CN Ethyl 3.6. H CN n-Propyl 3.7. H CN isopropyl 3.8. H CN n-Butyl 3.9. IH CN sec.-Butyl 3.10._fH CN tert.-Butyl 3.11._JH CN Cyclopropyl 3.2_H CN rCyciohexyl a..
a *a.
a a *aa a o.z. 0050/43197 No. RIR 2
R
3 phys. data 3.13. H CN Methoxymethyl 3.14. H CN Ethoxymnethyl 3.15. H CN Phenoxymethyl 3.16. H CN 3-Chiorophenoxymethyl 3.17. H CN Benzyloxymethyl 3.18. H CN 2-MethylbenzyloxymethyJ.
3.19. H CN Methyithiomethyl 3.20. H CN Phenyithiomethyl 3.21. H CN Ethynyl 3.22. H CN Phenylethynyl 3.23. H CN 1-Propynyl 3.24. H CN
CN
3.25. H CN Acetyl 3.26. H CN Propion-1--yl 3.27. H CN Butyr-1-yl 3.28. H CN isobutyr-1-yl 3.29. H CN Pivaloyl 3.30. H CN Benzoyl 3.31. H CN 4-Chlorobenzoyl 3.32. H CN Benzylcarboflyl 3.33. H ICN Methoxycarbolyl 3.34.- H CN lEthoxycarboflyl te. S S *5
S
5* 55 S 5 **S S *SSSS S S S S a S S S S S S S S S S S S S S. 5 555 *55 S o*Z. 0050/43197 No. RIR2 R3phys. data 33.HCN f-Propoxycarbonyl 33.HCN isopropoxycarbonyl 33. HCN n-But oxycarbony 1 33.HCN isobutoxycarbonyl 33. HCN sec Butoxycarbonyl 34. HCN tert But oxycarbonyl 34.HCN n-Hexoxycarbonyl 34.HCN Phenoxycarbonyl 34.HCN 4 -Chiorophenoxycarbonyl 34.HCN Benzyloxycarbonyl 34.HCN Aininocarbonyl 34.HCN Dimethy laminocarbony 1 34.HCN Diethylaminocarbonyl 34.HCN Di-isopropylaminocarbonyl 34.HCN Phenylaininocarbonyl N-Methy 1-N--pheny laminocarbony I HCN Phenyl 2-Fluorophenyl 3-Fluorophenyl HCN 4-Fluorophenyl HCN Pentafluorophenyl 3.CN 12-Chlorophenyl 9 9** 9** 9* 9*.
99 9*9 9 9 9 9 9e* 9 a 9. a a O.Z. 0050/43197 No. RiR'R 3 phys. data 3.57. H CN 3-Chlorophenyl 3.58. H CN 4-Chiorophenyl 3.59. H CN Pentachiorophenyl 3.60. H CN 2,3-Dichlorophenyl 3.61. H CN 2,4-Dichlorophenyl 3.62. H CN 3.63. H CN 2,6-Dichlorophenyl 3.64. H CN 3,4-Dichlorophenyl 3.65. H CN 3.66. H CN 2,3,4-Trichlorophenyl 3.67. H CN 2,3,5-Trichiorophenyl 3.68. H CN 2,3,6-Trichloroplhenyl 3.69. H CN 2 3.70. H CN 2,4,6-Trichlorophenyl 3.71. H CN 3,4,5-Trichlorophenyl 3.72. H CN 2,3,4,6-Tetrachlorophenyl 3.73. H CN 2,3,5, 6-Tetrachiorophenyl 3.74. H CN 2-Bromophenyl 3.75. H CN 3-Bromophenyl 3.76. H CN 4-Bromophenyl 3.77. H CN 2,4-Dibrornophenyl 3.78. CN 3-Bromo-4-f luorophenylI 9* 9*9 9 9 9..
9 S 9* 9 a S 9 9 9* o.Z. 0050/43197 01 No. R R R 3 phys. data 3.79. H CN 3-Bromo-4-methoxyphenyl 3.80. H CN 2-lodophenyl 3.81. H CN 3-Iodophenyl 3.82. H CN 4-Iodophenyl 3.83. H CN 2-Chloro-4-fluorophenyl 3.84. H CN 3.85. H CN 2-Chloro-6--fluorophenyl 3.86. H CN 2-Chloro-4-bromophenyl 3.87. H CN 2-Bromo-4--chlorophenyl 3.88. Hi CN 2-Bromo-4-fluorophenyl 3.89. H CN 3-Bromo-4-fluorophenyl 3.90. H CN 3-Chloro-4-fluorophenyl 3.91. IH CN 3-Fluoro-4-chloropheny- 3.92. H CN 2-Cyanophenyl 3.93. H CN 3-Cyanophenyl 3.94. H CN 4-Cyanophenyl 3.95. H CN 2-Nitrophenyl 3.96. H CN 3-Nitrophenyl 3.97. H CN 4-Nitrophenyl 3.98. H CN 2-Methyiphenyl 3.99. H CN 3-Methyiphenyl 3.100. H CN 4-Methylphenyl *0 a.
9 a.
a a a a a a a a a a a. a C o.Z. 0050/43197 No. RR2R 3 phys. data 3.101. H CN 2,4-flimethylphenyl 3.102. H CN 2,6-Dimethylphenyl 3.103. H CN 3,4-Dimethyiphenyl 3.104. H CN 3.105. H CN 2,3,4-Trimethyiphenyl 3.106. H CN 2,3,5-Trimethyiphenyl 3.107. IH CN 2,3, 6-Trimethyi~phenyl 3.108. H CN 2,4,5-Trimethyiphenyl 3.109. H CN 2,4,6-Txixnethylphenyl 3.110. H CN 3,4,5-Triinethylphenyl 3.111. H CN Pentamethyiphenyl 3.112. H CN 2-Ethyiphenyl 3.113. H CN 3-EthyiphenYl 3.114. fH CN 4-Ethylphenyl 3.115. H CN S3.116. H CN 2-n--Propylpheny.
3.1L17. H CN 3-n-Propylphenyl 3.118. H CN 4-n--Propylphenyl 3.119. H CN 2-isopropyiphenyl 3. 120. H CM 3-isopropylphenyl 3.121. H CN 4-isopropylphenyl 3.22I CN 2,4-Di-isopropylphenyl .0 to: :0 too a a. .aa a a a .a 11. to .0 a to*. to to. too a o.z. 0050143197 No. RI R 2
R
3 phys- data 3.123. H CN 3.124. H CN 4-n--Butyphenyl 3.125. H CN 4-sec.-Butylphenyl 3.126. H CN 4-iso-Butyiphenyl 3.127. H CN 4--tert.-Butylphenyl 3.128. H CN 3-tert.-BUtylphenyl 3.129. H CN 2-tert.-Butylphenyl 3.130. H CN 2, 4-Di-tert.-Butylphenyl 3.131. H CN 3.132. iTI CN 4-n-Hexylphenyl 3.133. H CN 4-n-Dodecylphenyl 3.134. H CN 2-Methyl-4-tert.-Butylphenyl 3.135. H CN 2-Methyl-6-tert.-Butylphenyl 3.136. H CN 2-Methyl-4-iso-Propylphenyl 3.137. H CN 2-Methyl-4--Cyclohexylphenyl 3.138. H CN 2-Methyl--4-Phenylphenyl 3.139. H CN 2-Methyl-4-Benqzylphenyl 3.140. H CN 12-Methyl-4-P-henoxyphenyl 3.141. 'H CN 2-Methyl-4-Benzyloxyphelyl 3.142. H CN 2-Methyl-3-Chlorophenyl 3.143. H CN 2-Methyl-4-Chlorophenyl 3.144. IH ICN 000 *0* 000 00 01~ 000 00 0 00 0 0 0 0*0 O.Z. 0050/43197 000 0 0 ~0 0 000000 0 No. RlR 2 FR3 phys. data 3.145. H CN -eh C 3.146. H CN 2-Methyl-4-Fluorophenyl 3.147. H CN 2-Methyl-3-Bromophenyl 3.148. H CN 2-Methyl-4--Bromophenyl____________ 3.149. H CN 2-Methyl-3-Methmrxyphenyl 3.150. 1H CN 2-Methyl-4--Methoxyphenyl 3.151. H CN 3.152. H CN 2-Methyl-6-Methoxyphelyl 3.153. H CN 2-Methyl-4-iso-Propoxyphenfl_____________ 3.154. H CN 2-Methyl-2,5-Dixnethoxyphenyl -ehxpey 3.155. H CN 2-methoxyphenyl 3.156. H CN 3-Methoxyphenyl 3.157. H CN 4,-ethoxyheylbey 3.158. H CN 2,4-Dimethoxyphenyl 3.159. H CN 2,4-Dimethoxyphenyl 3.160. H CN 3.161. H CN 2,6-Dimethoxyphenyl 3.162. H CN 3,4-Dimethoxyphelyl 3.163. H ICN 3.164. H CN 23,-imethoxyphenyl 3.165. H CN 2,3,4-Trimethoxyphenyl a a a. o.Z. 0050/43197 -No. RR2R 3 phys. data 3.167. H CN 2,3,6-Trimethoxyphell___________ 3.168. H CN 2,4,5-Trimethoxyphenll__________ 3.169. H CN 2,4,6-Trimethoxyphell_____________ 3.170. H ICN 3,4,5-Trimethoxyphell___________ 3.171. H ICN 2-Ethoxyphelyl 3.172. H CN 3-Ethoxyphelyl 3.173. H CN 4-Ethoxyphenyl 3.174. H CN 2-iso-Propoxyphell 3.175. H CN 3-iso--Propoxyphelyl 3.176. H CN 4-iso-Propoxyphelyl 3.177. H CN 3-tert.-BUtoxyphenll__________ 3.178. H CN 4-tert.-Butoxyphenll 3.179. H CN 2-Trifluoromethoxyphelyl 3.180. H CN 3-Trifluoromethoxyphenl 3.181. H CN 4-Trifluoromethoxyph(-nl 3.182. H CN 3-~(1,1',2'.2'-Tetraf1uoro)ethoxyphenyl 3.183. H CN 4-(1',1',2',2'-Tetra-fluoro)ethox~ypher.yl 3.184. H CN 2-Chloromethylphell 3.185. H CN 3-Choromethylphell- 3.186._ H CN 14-Chloromethylphenll_____________
S
a..
5 5 S *S S S S a O.Z. 0050/43197 No. RR2R 3 phys. data 3.187. H CN 2-Trifluoromethylphenyl 3.188. H CN 3-Trifluoromethylpheiyl 3.189. H CN 4-Trifluoromcethy~lpheny1 3.190. H CN 2- (Methoxyiminomethyl) -phenyl 3.191. H CN 3- (Methoxyim.:iomethyl) -pheny.
3.192. H CN 4- (Methoxyilninomethyl'/-phenyl 3.193. H CN 2-(Ethoxyiminomethyl)-phenyl 2.194. H CN 3- (Ethoxyiminomethyl) -phenyl 3.195. H CN 4-(Ethoxyimincmethyl)-phenyl 3.196. H CN 2- (n-Propoxyiminomethyl )phenyl 3.197. H CN 3-(n-Propoxyiminomethyl)pheniyl 3.199. H CN 4- (n-Propoxyiminomethyl, phenyl 3. 199. H CN 2- (iso-Propoxyiminomethyl )phenyl 3.200. H CN 3- (iso-Propoxyiminomethyl )phenyl 3.201. H -CN 4-(iso-Propoxyiminow',thyl)phenyl 3.202. H CN 2-(n-Butoxyiminomethyl)phenyl 3.2 03. H CN 3- (n-Butoxyiminomethyl)phenyl 3.204. H CN 4-(n-Butoxyiminomethyl)phenyl 3.205. H CN 2- (iso-Butoxyixninornethyl)phenyl 3.206. H CN 3- (iso-Butoxyiminomethyl)phenylI 3.207. IH ICN 14-(iso-Butoxyixninomethyl)phenyl 3.208. IH J 21- (tert Butoxyiminomethyl)phenyI Ow 4* *4e 4 4 4. .4 4 4 4 4.4.
U 4 0, 4 .4 a 9 a 44 4 444 O.Z. 0050/43197 No. RlR 3phys. data 3.209. H CN 3-(tert Butoxyiminomethyl)phenyI 3.210. H CNq 4-(tert.-IButoxyiminomethyl)phenyl 3.211. H CN 2-(n-Pentoxyiminomethyl) -phenyl 3.212. H CN 3-(n-Pentoxyiminornethyl)-phenyil____________ 3.213. H CN 4-(n-Pentoxyiminonethy.)--phenyl 3.214. H CN 2-(n-Hexoxyiminomethyl)-phenyl 3.215. H CN 3-(n-He,.oxyiminomethyl) -phenyl 3.216. H CN 4-(n-Hexoxyiminomethyl)-phenyl 3.217. H CN 2-(Allyloxyiminomethyl)-pheny.
3.218. H CN 3- (Allyloxyiminomethyl)-phenyl 3.219. H CN 4- (A 1 lyloxyiminomethyl) -phenyl 3.220. H CN 2- (Benzyloxyiminom-ethyl) -phenyl 3.221. H CN 3- (Benzyloxyiminomethyl) -phenyl 3.222. H CN 4-(Benzyloxyiminomethyl)-phenyl 3.223. H CN 2- (Methoxyimino-1' -ethyl) -phenyl 3.224. H CN 3-(Methoxyimino-1 '-ethyl)-phenyl 3.225. H CN 4-(Methoxyim.Lno-1'-ethyl) -phenyl 3.226. H CN 2- (Ethoxyimino-1'-ethyl) -phenyl 3.227. H- CN 3-(Ethoxyimino-1'-ethyl)-phelyl 3.228. H CN 4-(Ethoxyimino-1'-ethyl)-phenyl 3.229. H CN 2-(n-Propoxyimino-1'-ethyl)phenyl 3.230. H CN 3- (n-Propoxyimino-1 '-ethyl)phenyl to so .0 to 09.9 to .0 t. Ov 0 a 9. .9 o.Z. 0G50/43197
S
No. RR2R 3 phys. data 3.231. H CN 4- (n-Propoxyirnino-1 '-ethyl)pheiyl 3.232. H CN 2- (n-Butoxyamino-1' -ethyl)phenyl 3.233. H CN 3-(n-BUtoxyamino-1'-ethyl)phenyl 3.234. H CN 4-(n-Butoxyamino--1'-ethyl)phenyl 3.235. H CN 2-(n-Pentoxyimino-l'-ethyl)phenyl 3.236. H CN 3- (n-Pentoxyimino-l'-ethyl)phenyl 3.237. H CN 4-(n--Pentoxyiinino-1 '-ethyl)phenyI.
3.3.H cli 2-(n-Hexoxyimino-l'-ethyl)phenyl 3.3.H CN 3-(n-Hexoxyimino-1'-ethyl)phenyl 3.240. H CN 4- (n-Hexoxyimino-1'-ethyl)phenyl 3.241. H CN 2-(Allyloxyimino-1'-ethyl)-phenyl 3.242. H1 CN 3-(Allyloxyimino-1'-ethyl)-phenyl 3.243. H CN 4-(Allyloxyimino-1'-ethyl)-phenyl 3.244. H CN 2- (Benzyloxyimino-1 '-ethyl)phenyl 3.245. H CN 3- (Benzyloxyimino-l'-ethyl)phenyl 3.246. H CN 4- (Benzyloxyimino-1 '-ethyl)phenyl 3.247. H CN 2-Phenyiphenyl 3.248. H CN 3-Phenylphenyl 3.249. H CN 4-Phenylphenyl 3.250. H CN 2-Phenoxyphenyl 3.251. H CN 1 3-Phenoxyphenyl_____________ 3.252. 1H CN 14-Phenoxyphenyl S S S S S S S O.Z. 0050/43197 No. RlR 2
R
3 phys. data 3.253.
1 H CN 2-Benzyloxyphenyi 3.254. H CN 3-Benzyioxyphenyl 3.255. H CN 4-Benzyioxyphenyi 3 5.hCN 4- (Imida7ol-i' -yl )phenyl 4- (Piperaz in-i' -yl) phenyl 4- (Morpholin-1'-y phenyl 3.29. CN4- (Piperidin-1' -yl) phenyl 3.20. CN4- (Pyridyl-2 '-oxy)phenyl 3.261 H N2 -Cyciopropyiphenyl 3.262. H CN 3-Cyclopropylphenyl 3.263. H CN 4-Cyclopropylphenyi 3.264. H CN 3-Cyclohexyiphenyl 3.265. H CN 4-Cyclohexyipheniyl 3.266. H CN 4-Oxiranyiphenyl 3.267. H CN 4-(l',3'-Dioxan-2'-yl)-phenyl 3.268. H CN 4- (Tetrahydropyran2-yloxy)-phenyl 3.269. H CN 1-Naphthyl 3.270. H CN 2-Naphthyl 3.271. H CN Benzyl 3.272. H CN 2-Methylbenzyl 3.273. H CN 3-Methylbenzyl 3.274 H CM4-methylbenzyl *5e S *S. a a a 0 a a a. o.z. 0050/43197 F~IR1 rR2 IR3 _phys. data 3.275. H CN 4-tert.-BUtylbenzyl 3.276. H CN 2-Chlorobenzy.
3.277. H CN 3-Chlorobenzyl 3.278. H CN 4-Chlorobeflzyl 3.279. H CN 2,4-Dichlorobenzyl 3.280. H CN 2,6-Dichlorobel 3.281. H CN 2,4,6-Trichlorobelzyl 3.282. H CN 2-TrifluoromethylbezlZ~ 3.283. H CN 3-Trifluoromethylbel 3.284. H CN 4-trifluoromethylbezlZ~ 3.285. H CN 2-M~et hoxybenzy 1 3.286. H CN 4-Methoxybelzyl 3.287. H CN 4-tert.-ButoxybeflZY1 [328.H CN 4-PhenoxybenzyJ.
3.289. H CN I-Phenethyl 3.290. H CN 2-Phenethy.
3.291. H CN 1-Phenylpropyl 3.292. H CN 2-Phenylpropyl 3.293. H CN 3-Phenylpropyl 3.294. H CN 2-Methyl-2-phelylpropyl 3.295. H CN _2-Methyl-3-phellpropyl 3.296.
4 -Phenylbutyl
I
S 555 o.Z. 0050/43197 No. Rl phys. data 3.297. H CN 2-Phenyl-l-ethenyl_____________ 3.298. H CN 1-Phenyl-l-ethenyl 3.299. H CN 1-Phenyl-l-propeiyl_____________ 3.300. H CN I-Phenyl-l-propen-2-yl 3.301. H CN 2, 2-Diph~nylelthenyl 3.302. H CN 2 -Pyridyl I 3.303. H CN 3-Pyridyl 3.304. H CN 4-Pyridyl 3.305. H CN 2,6-Pyrimidinyl 3.306. H CN 3.307. H CN 2-Thienyl 3.308. H CN 3-Thienyl 3.309. H CN 2-Furyl 3.310. H CN 3-Puryl 3.311. H CN 1-Pyrrolyl 3.312. H CN 1-Imidazolyl 3.313. H CN 1,2,4-Triazolyl 3.314. H CN 1,3,4-Triazolyl 3.315. H CN 4-Thiazolyl 3.316. H CN 2-Benzothiazolyl 3.317. H CN 2-Pyridylmethyl 3.318. H CN 3-Pyridylmethyl_____________ a O.Z. 0050/43197 Ho CNR R 3 phys. data 3.319. H N2'-Furyl-2-ethenyl 3.320. H CN 2'-Thienyl-2-ethenyl 3.321. H CN 3'-Pyridyl-2-ethenyl 3.322. H CN Oxiranyl 3.323. IH CN 1-Aziridinyl 3.324. IH CN 1-Azetidinyl 3.325. H CN 1-Pyrrolidinyl 3.326. H CN 2-Tetrahydrofuryl 3.327. H CN 2-Tetrahydropyralyl 3.328. 1H CN 3-Tetrahydropyranyl 3.329. H CN 1-Piperidinyl 3.330. H CN 1-Morpholinyl 3.331. H CN 1-Piperazinyl 3.332. H CN 1,3-Dioxan-2-yl 3.333. H CN 4-Tetrahydrothiopyralyl 3.334. H CN 4-Methylpent-3-en-1-yI 3.335. H CN 2-Propenyl 3.336. H CN 2-Butenyl 3.337. H CN 1-Methyl-2-propelyl 3.338. H CN j3-Methyl--2-butenyl 3. 9. 1H CN I2,2-Difluoroethenyl 3.340. IH Ci 12, 2-Dichioroethenyl S S S S S S S S O.Z. 0050/43197 No. RIR 2 R3 phys. data 3.341. H CN 3,3,3-Trifluoropropenyl 3.342. H CN 3,3.3-Trichloropropenyl 3.343. H CN 3-Chloro-2-propenyl 3.344. H CN Cyclopent-l-enyl 3.345. H CN Cyclopentadienyl_____________ 3.346. H CN Cyclohex-1-enyl 3.347. H CN Pentafluorocyclopenradienyl 3.348. H CN Pentachlorocyclopentadienyl 3.349. H CN Styryl 3.350. H CO2Me Phenyl 3.351. H CO 2 Me 2-Fluorophenyl 3.352. H CO 2 Me 3-Fluorophenyl 3.353. H ICOi)Me 4-Fluorophenyl 3.354. H CO 2 Me 2-Chiorophenyl 3.355. H CO2,Me 3-Chlorophenyl 3.356. H CO 2 ,Me 4-Chlorophenyl 3.357. H CO 2 Me 2-Methylphenyl 3.358. H CO 2 Me 3-Methyiphenyl 3.359. H CO 2 )Me 4-Methyiphenyl 3.360. H CO:Me 2-Cyanophenyl 3.361. H COMe 3-Cyanophenyl 3.362. H COQMe 6.-Cyanophenyl S S o.Z. 0050/43197 No.- R R- R 3 phys. data 3.363. H co. Me 2-Methoxyphelyl 3.364. H CO.Me 3-Methoxyphenyl 3.365. H CO-Me 4-Methoxyphenyl 3.366. H
CO,
2 Me 2-Nitrophenyl 3.367. H C0 2 Me 3-Nitrophenyl 3.368. H CO 2 Me 4-Nitrophenyl 3.369. H p(O) (OMe) 2 Phenyl 3.370. H P(O) (OMe) 2 2-Fluorophelyl 3.371. H P(O) (OMe) 2 3-F-luorophelyl 3.372. H P(O) (Ome)q 4-Fluorophelyl 3.373. H P(O) (OMe) 2 2-Chiorophelyl 3.374. H P(OJ (OMe) 2 3-Chiorophelyl 3.375. IH P(O) (OMe) 2 4-Chlorophenly 3.376. H P(O) (OMe)2 2-Methyiphelyl 3.377. H P(O) (OMe) 2 3-Methyiphelyl 3.378. H P(O) (Ome) 2 4-methylphelyl 3.379. CH 3 CN Phenyl 3.380. Acetyl H 2,.6-Dichlorophell 3.381. Acetyl H 2,4-Dichlorophelyl 3.382. OHI- CO-Et Benzoyl 3.383. Methoxycar- H Acetyl bony ipheny 1 a a a..
a a a a a a a a a a. a *aa a 86 o.Z. 0050/43197 9 0 o.Z. 0050/43197 S S S S S S S S 5.5 t S S P 5 O.Z. 0050/43197 S S 55 S asa
C..
a S o.z. 0050/43121 0 R 2 pH: PIJIYS. d Uc~ 3.394CF
CH
2
NCH
3.395 0 0 0 o 3.396 OEL I CH-t CH2 0 I L p A as..
eft p pa.
a a p. p .a *a a a a *Sa peap p a p pp aa a a a a. a a O.Z. 0050/43197
-CH
3
'CH
2 3.398 CH3 *0* 9 S S *e 9* 99* O.Z. 0050/43197 .0 *0
S..
S S* S SS S S S S S S* S S S S S S S S. S S O.Z. 0050/43197 0l No. I phys. data 3.402 -0 H 0 0 3.403 -o H N 0
CH
3 0 0 0 C C C o.Z. 0050/43197 Table 4
NH
CHa No. R R phys. data 4.1. H H CF 3 4.2. H CF 3
CF
3 4.3. H CFj Pheniyl 4.4. H CN Methyl H CN Ethyl 4.6. H CM n-Propyl 4.7. H CN iso-Propyl 4.8. H CN n-Butyl 4.9. H CN sec.-Butyl 4.10. H jCM tert.-Butyl a. a a. a a a a a a a a a a O.Z. 0050/43197 No.__Rl phys. data 4.11. JH CN Cyclopropyl 4.12. H CN Cyclohexyl 4.13. H CN Methoxyrnethyl 4.14. H CN Ethoxyinethyl 4.15. H CN Phenoxymethyl 4.16. H CN 3-Chlorophenoxymethyl___________ 4.17. H CN Benzyloxymethyl 4.18. H CN 2-Methylbenzyloxymethyl 4.19. H CN Methylthiomethyl 4.20. H CN Phenyithiomethyl 4.21. H CN Ethynyl 4.22. H CN Phenylethynyl 4.23. H CN I-Propynyl 4.24. H CN CN 4.25. H CN Acetyl 4.26. H CN Propion-1--yl 4.27. H CN Butyr-1-yl 4.28. H CN iso-Butyr-1-yl 4.29. H CN Pivaloyl 4.30. H CN Benzoyl 4.31. H CM 4-Chlorobenzoyl 4.32. H CN Benzylcarbonyl S. S.
C C S S a C C C S S C S *5 a S o.z. 0050/43197 0 No. jRl R"R 3 phys. data 4.3 CN Methoxycarbolyl 4.34. H CN Ethoxycarbonyl 4.35. H CN n-Propoxycarbonyl~__________ 4.36. H CN iso-Propoxycarbonyl 4.37. H CN n-Btitoxycarboflyl 4.38. H CN iso-Butoxycarbonyl 4.39. H CN sec.-Butoxycarboflyl 4.40. H CN tert.-Butoxycarboflyl 4.41. H CN n-Hexoxycarboll 4.42. H CN Phenoxycarbonyl 4.43. H CN 4-Chlorophenoxycarbofll 4.44. H CN Benzyloxycarbonyl 4.45. H CN Aminocarbolyl 4.46. H CN Dimethylaminocarboflyl 4.47. H CN Diethylaminocarbofll 4.48. H CN Di-iso-Propylailocarbol 4.49. H CN Phenylaminocarboll 4.50. H CM IN-Methyl-N-Phelylamiflocarbofll_________ 4.51. H CN Phenyl 4,52. H CN 2-Fluorphenyl 4.53. 1H CN 3-Fluorphelyl 4.54. IH ]CM 4-Fluorphenyl I I I I S S I S. C O.Z. 0050/43197 No. RIR:R 3 phys-. data 4.55. H CN Pentafluorophenyl 4.56. H CM 2-Chlorophenyl 4.57. H CM 3-Chiorophenyl 4.58. H CM 4-Chiorophenyl 4.59. H CN Pentachlorophenyl 4.60. 1H CM 2,3-Dichiorophenyl 4.61. H CM 2,4-Dichlorophelyl 4.62. H CN 4.63. H CN 2, 6-Dichiorophenyl 4.64. H CN 3,4-Dichlorophenyl 4.65. H CM 4.66. H CM 2,3,4-Trichlorophelyl 4.67. H CM 2,3,5-Trichlorophelyl 4.68. H CM 2,3, 6-Trichiorophenyl 4.69. H CM 2,4,5-Trichiorophelyl 4.70. H CN 2,4,6-Trichlorophell 4.71. H CN 3,4,5-'rrichlorophenyl 4.72. H CN 2,3,4, 6-Tetrachlorophenyl 4.73. H CN 2,3, 5,6-Tetrachiorophelyl 4.74. H CN 2-Bromonhenyl F47.HCM 3-Bromophenyl liCN 14-Bromophenyl
S
S S .5-Se S S o.Z. 0050/43197 No. Rl R R 3 phys. data 4.77. H CN 2,4-Dibromophenyl 4.78. H CN 3-Broino-4-Fluorophenyl 4.79. H CN 3-Bromo-4-Methoxyphell 4.80. H CN 2-Iodophenyl 4.81. H CN 3-Iodophenyl 4.82. 1H CN 4-Iodophenyl 4.83. H CN 2-Chloro-4-Fluorophelyl 4.84. H CN 4.85. H CN 2-Chloro-6-Fluorophenfll 4.86. H CN 2-Chloro-4-Bromophenyl 4.87. H CN 2-Bromo-4-Chlorophenyl 4.88. H CN 2-Bromo-4-Fluorophelyl 4.89. H CN 3-Bromo-4-Fluorophell 4.90. H CN 3-Chloro-4-Fluorophelyl 4.91. H CN 3-Fluoro-4-Chlorophelyl_________ 4.92. H CN 2-Cyanophenyl 4.93. H CN 3-Cyanopheny.
4.94. H CN 4-Cyanophenyl 4.95. H CN 2-Nitrophenyl 4.96. H CN 3-Nitrophelyl 4.97. H CN 4-Nitrophenyl 4.98. IH CN 2-Methylphenyl
S
S
S S S *S S
S
S
S. S. 55 .5.
S S a
S
*SS* eSO O.Z. 0050/43197 No.- RIR R 3 phys. data 4.99. H CN 3-Methyiphenyl 4.100. H CN 4-Methyiphenyl 4.101. H CN 2,4-Dimethyiphenyl 4.102. H CN 2,6-Dimethylphenyl___________ 4.103. H CN 3,4-Dimethylphenyl 4.104. H CN 4.105. H CN 2,3,4-Trimethylphenyl 4.106. H CN 2,3,5-Triniethylphenyl 4.107. H CN2,3,6-Triniethylphenyl 4.108. H CN 2,4,5-Trimethylphenyl 4.1,09. H CN 2,4,6-Trimethylphenyl 4.110. H CN 3,4,5-TFrimethylphenyl 4.111. H CN Pentarnethyiphenyl 4.112. H CN 2-Ethyiphenyl 4.113. H CN 3-Ethylphenyl 4.114. H CN 4-Ethyiphenyl 4.115. H CN 4.116. H CN 2-n-Propylphenyl 4.117. H CN 3-n-Propylphenyl 4.118. H CN 4-n-Propylphenyl 4.119. H CN 2-iso-Propyiphenyl 4.120. H CN 3-iso-Propylphenyl a a aa a a a..
a. a. a. a C a. a a a a a a. a O.Z. 0050/43197 No. RR2R 3 phys. data 4.121. H CN 4-iso-Propylphenyl___________ 4.122. H CN 2,4-Di-iso-PropyJlphenyl 4.123. H CN 4.124. H CN 4-n-Butyphelyl 4.125. H CN 4-sec.-Butylphenyl 4.126. H CN 4-iso-Butylpheny.
4.127. H CN 4-tert.-Butylphelyl 4.128. H CN 3-tert.-Butylphelyl 4A29. H CN 2-tert.-Butylphelyl 4.130. 1H CN 2,4--Di-tert.-Butylphell_________ 4.131. H CN 4.132. H CN 4-n-Hexylphelyl 4.133. H CN 4-n-Dodecylphelyl 4.134. H CN 2-Methyl-4-tert.-Buty1lphell 4.135. H CN 2-Methyl-6-tert.-Butylphelyl 4.136. H CN 2-methyl-4-iso-Propylphell 4.137. H CN 2-Methyl-4-Cyclohexylphell 4.138. H CN 2-Methyl-4-Phenylphelyl 4.139. H CN 2-Methy1-4-Benzylpheli 4.1'C. jH_ CN 2--Methyl-4-Phefloxyphefll 4.141. H CN 2-Methyl-4-Benzyloxyphell 4.142 H CN 2-Methyl-3-Chlorophell lb 4..
U..
a a. a.
a a a a ap a a a a a a e **aa a a. a o.Z. 0050/43197 100 No. lR
R
3 phys. data 4.143. H CN 2-ethyl-4-Chloropheny- 4.144. H CN 4.145.q CN 1 2Methyl-6-Chlorophenl 4.145. H CN -ehl4Furp ny 4.147. H CN 2-methyl-4-Fluorophefll 4.147. H CN 2-ethyl-3-Bromophenyl 4.148. IH CN 2-Methyl--rolpheyl 4.149. H CN 2-Methyl-3-Methoxyphell 4.151. H CN 2-Methyl-4-Methoxyphell________ 4.152. H CN 2-Methyl-6-Methoxyphelyl 4.153. H CN2-Methyl-4-iso-Propoxyphel___________ 4.154. H CN 2-Methyl-2,5-Dimethoxyphell_________ 4.155. H CN 2-Methoxyphenyl 4.156. H CN 3-Methoxyphelyl__ 4.157. H4 CN 4-Metlhoxyphelyl 4.159-. H cN2,3-Dimethoxyphelyl 4.159. H CN 2,4-Dimethoxyphelyl 4.160. H CN 4.161. H CN 2,6-Dimethoxyphelyl 4.162. IH CN 3,4-Dimethoxyphelyl 4.163 .I CN 4.164. H CN 3,6-Dimethoxyphenyl__________ St* S 5t5 S S S S S 1~ S S S S S S. O.Z. 0050/43197 101 No. RlR 2
R
3 phys. data 4.165.- H CN 2,3,4-Trirnethoxyphelyl 4.166. H CN 2,3,5-Trimethoxyphelyl 4.167. H CN 2,3,6-Trimethoxyphenyl 4.168. H CN 2,4,5-Trimethoxyphelyl 4.169. H CN 2,4,6-Trimethoxyphelyl 4.170. H CN 3,4,5-Trirnethoxyphenyl 4.171. H CN 2-Ethoxyphenyl 4.172. H CN 3-Ethoxyphelyl 4.173. H CN 4-Ethoxyphenyl 4.174. H CN 2-iso-Propoxyphenyl 4.175. H CN 3-iso-Propoxyphenyl 4.176. H CN 4-iso-Propoxyphelyl 4.177. H CN 3-tert.-Butoxyphelyl 4.178. H TN 4-tert. -Butoxyphenyl 4.179. H CN 2-Trifluoromethoxyphell 4.180. H CN 3-TrifluoromethoxyphelYl 4.181. H CN 4-Trifluoromethoxyphell 4.182. H CN 3-~(1'A1',2',2'-Tetrafluoro)ethoxyphel 4.183. H CN 4-(1',1',2',2'-Tetrafluoro)ethoxyphel 4.184. H CN 2-Chloromethylphenll 4.185. H IN 3-Chloromethylphenyl 4.86 HCN 4-Chioromethyiphenyl S Sb S S SS* S S S @55 S S S S S S S S S S S 5 S U* .55 5 o.z. 0050/43197 102 No. RR2R 3 phys. data 4.187. H CN 2-Trifluoromethylphenyl___________ 4.188. H CN 3-Trifluoromethyiphenyl 4.189. H CN 4-Trifluoromethylpheiyl 4.190. H CN 2-(Methoxyiininomethyl)-phenyl 4.191. H CN 3- (Methoxyiminomethyl) -phenyl 4.192. H CN 4-(Methoxyirninomethyl)-phenyl 4.193. H CN 2-(Ethoxyiminomethyl)-phenyl 4.194. H CN 3- (Ethoxyiminomethyl) -phenyl 4.195. H CN 4-(Ethoxyiminomethyl)--phenyl 4.196. H CN 2- (n-Propoxyixninomethyl )phenyl 4.197. HI CN 3- (n-Propoxyiminomethyl )phenyl 4.198. H CN 4- (n-Propoxyiminomethyl)phenyl 4.199. H CN 2-(iso-Propoxyixninomethyl)phenyl 4.200. H CN 3- (iso-Propoxyiminomethyl )phenyl 4.201. H CN 4- (iso-Propoxyiminomethyl)phenyl 4.202. H- CN 2-(n-Butoxyiminornethyl)phenyl 4.203. H CIN 3-(n-Butoxyiminomethyl)phenyl 4.204. H CN 4- (n-BUtoxyiminomethyl)phenyl 4.205. H CN 2-(iso-Butoxyiminomethyl)phenyl 4.206. H CN 3- (iso-Butoxyiminomethyl)phenyl 4.207. H CN 4-(iso-Butoxyiminomethyl)phenyl 4.208._jH CN 12- (tert.-Butoxyirninornethyl)phenyl
C
a..
a..
Ce.
a
C..
a. Ce .e S a a etC
S
C C C C Ce *t C C C. a St. C O.Zi. 0050/43197 103 No. R1 R2R 3 phys. data 4.209. H CN 3- (tert.-Butoxyiminomethyl)phenyl 4.210. H CN 4- (tert Butoxyiminomethyl)phenyl___________ 4.211. H CN 2- (n-Pentoxyiminornethyl)phenyl 4.212. H CN 13- (n-Pentoxyiminomethy1)phenyl 4.213. H CN 4-(n-Pentoxyiminomethyl)phenyl 4.214. H CN 2-(n-Hexoxyiminomethyl)-phenyl 4.215. Hi CN 3- (n-Hexoxyimino~methyl) -phenyl 4.216. H CN 4- (n-Hexoxy'ip~inomethyl) -phenyl 4.217. H CN 2-(Allyloxyiminomethyl)-phenyl 4.218. H CN 3- (A11ylcrxyiminomethyl)-phenyl 4.219. H CN 4-(Allyloxyiminomethyl)-phenyl 4.220. H CN 2- (Benzyloxyiminoniethyl)I-phenyl 4.221. H FN 3- (Benzyloxyiminomethyl) -phenyl 4.222. P CN 4-(Benzyloxyiminomethyl)-phenyl 4.223. H CN 2- (Methoxyimino-1'-ethyl) -pheriyl 4.224. H C3-(MathoxyintLuo-l'-ethyl) -phenyl 4.225. H CN 4- Ow r ho>xyixino-! '-ethyl) -phenyl 4.226. H CN 2- (Ethoxyzino-1'-Elthyl)-phenyl 4.227. H CN 3- (Ethoxyimino.-1'-ethyl)-phenyl 4.228. H CN 4-(EthcxyWimino-1'--ethyl)-phenyl 4.229. IH CN 2- (n-Propoxyimino-1 -ethy1iphenyl 4.3.H ICN .3-(n-Propoxyimino-1'-ethy'Ljphenyl___________ 0* r
S..
0 0*S
-S
0 5 **0
S
a. C a 0 a S. aS S a. S asS S o.Z. 0050/43197 104 No.- JRI R2 I R3 I phys. data 4.231. H CN j-t-(n-Propoxyimino-1'-ethy1)phenyl___________ 4.232. H CN 2- (n-Butoxyamino-l--ethiyi)phenyl 4.233. H CN 3-(n-Butoxyamino-i'-ethyl)phenyl jN 4.234. H CN 4- (n-Buntoxymino- '-ethyl) phenyl 4.235. H CN 2-(n-Pentoxyimino-1'-ethyl)phenyl 4.3.HC1-nPnoymn-'ehlpey 4.237. IH CN 4-(n-Pentoxyimino-l'-ethyl)phenyl 4.238. H CN 2- (n-Hexoxyimino-1'-ethyl)phenyl 4.239. H CN 3-(n-Hexoxyimino-1'-ethyl)phenyl 4.240. H CN 4- (n-Hexoxyimino-1' -ethyliphenyl 4.241. H CN 2- (Allyloxyimino-1 '-ethyl) -phenyl 4.242. H CN 3-(Allyloxyimino-l'-ethyl)-phenyl 4.243. H 4-(lyoymiol-ty)phnl____ 4.244. H CN j (Benzyloxyimino-l'-ethyl)phenyl 4.245. H CN 3- (Benzyloxyimino-l'-ethyl )phenyl 4.246. IH CN 4-(Benz, xyimino-II-ethyl)phenyl 4.247. H CN 2-Phenyiphenyl 4 48 H 4.2498. H 3N -Phenylphenyl 4.250. j H 2-Phenoxyphenyl 4.251. H 3 -Phenoxypheny 1 4.252. 1IH J CN I4-heoxphenyl 0** 0 O.Z. 0050143197 105 No. fl R2 R 3 phys. data 4.253., H CN 2-Benzyloxyphenyl 4.254. (H CN 3-Benzyloxyphenyl 4.255. H Cb7- 4-Benzylcxcyphenyl CN 4-(Imidazol-l'-yl)phenyl CN 4-(Piperazin-1'-yl)phenyl I4.258. H CN 4-(Morpholin--1'-yl)phenyl 4.259. H CN4-(Piperidin-1'-yl)phenyl 4.260. H CN 4- (Pyridyl-2 '-oxy)phenyl 14.261. H CN 2-Cyclopropylphenyl 4.262. H CN 3-Cyclopropylphenyl 4.263. H CN 4-Cyclopropylphenyl 4.264. H CN 3-Cyclohexylphenyl 4.265. H CN 4-Cyclohexylphenyl 4.266. H CN 4-oxiranylphenyl 4.267. H CN 4-(1',3'-Dioxan-2'-yl)-phenyl 4.268. H CN 4- (Tetrahydropyran2-yloxyj -phenyl 4.269. H CN I-Naphthyl 4.270. H CN 2-Naphthyl 4.271. H CN Benzyl 1.7. N2-Methylbenzyl 4.273. H CN 3-Methylbenzyl 4.7.H ICN 4-Methylbenzyl V a a OA~. 0050/43197 106 No. RI R R 3 phys. data 4.275. H CN 4-tert.-Butylbenzyl 4.276. 11 CN 2-Chlorobenzyl___________ 4.277. H CN 3-Chlorobenizyl 4.278. H CN 4-Chlorobenzyl 4.279. H CN 2,4-Dichlorobenzyl 4.280. H CN 2,6-Dichlorobenzyl 4.281. H CN 2,4,6-Tric-hlorobenzyl 4.282. H CN 2-Trifluoromethylbenzyl 4.283. H CN 3-Trifluoromethylbenzyl 4.284. H CN 4-trifluoromethylbenzyl 4.285. H CN 2-methoxybenzyl 4.286. H CN 4-methoxybenzyl 4.287. H CN 4-tert.-Butoxybenzyl 4.288. H CN 4-Phenoxyberizyl 4.289. H CN 1-Phenethyl 4.290. H CN 2-Phenethyl 4.291. H CN 1-Phenyipropyl 4.292. H CN 2-Phenylpropyl 4.293. H CN 3-PhenylproPyl 4.294. H CN 2-Methyl-2-phenylpropyl t4.295. H CN 2-Methyi-3-phenylpropyl 4.296. H CN 4-Phenylbutyl a a a a a o.Z. 0050/43197 107 No. Rl 2R phys. data 4.297. H CN 2-Phenyl-l-ethenyl___________ 4.298. H CN 1-Phenyl-1--ethenyl 4.299. 1H CN 1-Phenyl-l--propeflyl 4.300. H CN 1-Phenyl-l-propen-2-yl 4.301. H CN 2,2-Diphenylethenyl 4.302. H CN 2-Pyridyl 4.303. H CN 3-Pyridyl 4.304. H CN 4-Pyridyl 4.305. H CN 2,6-Pyrimidinyl 4.306. H CN 1,5-Pyrimidinyl 4.307. H- CN 2-Thienyl 4.308. H CN 3-Thienyl 4.309. H CN 2-Furyl 4.310. H CN 3-Furyl 4.311. H CN 1-Pyrrolyl 4.312. H CN 1-Imidazolyl 4.313. H CN 1,2,4-Triazolyl 4.314. H CN 1,3,4-Triazolyl 4.315. H CN 4-Thiazolyl 4.316. H CN 2-Benzothiazolyl 4.317. H CN 2-Pyridylmethyl 4.318. H CN 3-Pyridylmethyl
C.
S a 0..
S C C C C C o.Z. 0050/43197 01 108 No. RlR 2
R
3 phys. data 4.319. H CN 2'-Furyl-2-ethenyl 4.320. H CN 2'-Thienyl-2-ethenyl 4.321. H CN 3'-Pyridyl-2-ethenyl 4.322. H CN Oxiranyl 4.323. H CN 1-Aziridinyl 4.324. H CN 1-Azetidinyl 4.325. H CN 1-P1yrrolidinyl 4.326. H CN 2-Tetrahydrofuryl 4.327. H CN 2-Tetrahydropyranyl 4.328. H CN 3-Tetrahydropyranyl 4.329. H leN 1-Piperidinyl 4.330. H CN 1-Morpholinyl 4.331. H CN 1-Piperazinyl 4.332. H CN 1,3-Dioxari-2-yl 4.333. IH CN 4-Tetrahydrothiopyralyl 4.334. H CN 4-Methylpent-3-en-1-yl 4.335. H CN 2-Propenyl 4.336. H CN 2-Butenyl 4.337. H CN 1-Methyl-2-propenyl 4.338. H CN 3-Methyl--2-butenyl 4.339. H CN 2,2-Difluoroethenyl 4. 340. IH CN i2,2-Dichloroethenyl a a. a a a o.Z. 0050/43197 109 No. RlR 3phys. data 4.341. H CN 3,3,3-Trifluoropropenyl 4.342. H CN 3,3,3-Trichioropropenyl 4.343. H CN 3-Chloro--2-propenyl 4.344. H CN cyclopent-l-enyl 4.345. H- CN Cyclopentadienyl 4.346. H CN lCyclohex-1-enyl 4.347. H CN Pentafluorocyclopentadienyl 4.348. H CN Pentachlorocyclopeitadielyl P.349. H CN Styryl 4.350. H CO 2 Me Phenyl 4.351. H CO2Me 2-Fluorophenyl 4.352. H CO 2 Me 3-Fluorophenyl 4.353. H CO 2 Me 4-Fluorophenyl 4.354. H C0 2 Me 2-Chlorophenyl 4.355. H C0 2 Me 3-Chlorophenyl 4.356. H CO 2 IMe 4-Chiorophenyl 4.357. H CO 2 Me 2-Methylphenyl 4.358. H CO 2 Me 3-Methylphenyl 4.359. H CO 2 Me 4-Methylphenyl 4.360. H COnMe 2-Cyanophenyl 4.361. H I 3-Cyanophenyl 4.362.
CO-Me 4-Cyanophenyl
I
I a a a. a a a *5 0 O.Z. 0050/43197 110 No. RR2R 3 phys. data 4.363. H
CO
2 Me 2-Methoxyphenyl 4.364. H CO 2 Me 3-Methoxyphenyl 4.365. H
CO
2 Me 4-Methoxyphenyl 4.366. H CO 2 Me 2-Nitrophenyl 4.367. H
CO
2 Me 3-Nitrophenyl 4.368. H CO 2 ,Me 4-Nitrophenyl 4.369. H P(O)(OMe)2 Phenyl 4.370. H P(O) (OMe) 2 2-Fluorophelyl 4.371. H_ P(O)(OMe)2 3-Fluorophenyl 4.372. H P(O) (OMe) 2 4-Fluorophelyl 4.373. H P(O)(Qme) 2 2-Chiorophenyl 4.374. H P(O)(OMe) 2 3-Chlorophenyl 4.375. H P(O) COMe) 2 4-Chiorophenyl 4.376. H P(O) (OMe) 2 2-Methylphenyl 4.377. H P(O)(OMe)2 3-Methylphelyl 4.378. H P(O) COMe) 2 4-Methyiphenyl 4.379. C11 3 CN Phenyl 4.380. Acetyl H 2,6-Dichlorophenyl 4.381. Acetyl H 2,4-Dichiorophelyl 4.382. CH-1
CO
2 -Et Benzoyl 4.383. Methoxycar- H Acetyl bony imet hyl I1 a a a..
a a a a a a a a. 0* a. a *aa O.Z. 0050/43197 ill No. 0 R2phys. data 4.384 a- 0 4.385 0 0 4.386 CHi 2 CH3 a, eb. S.
S** S S S *5 S *5 *S S *0SSS S a S S S S. S S O.Z. 0050/43197 112 No. -T-2 phys. data 0 R 4.387 4.388 0 0CH 3 4.389 0 CH3 0 :1 Cfl3 S PR .4.
4*
S
o S 4 S..
S S 4 S *0 4 *O CO 545 4 5 ft 04W awne~. ft ft 9 4 4 5 We. ft 5 ft S. *1 9 5 44 4 545 *45 O.Z. 0050/43197 0i 113
FNO.
0 R2 FLY S I i 4.391 0 04 4.392 0 0
CH
3 4.393 N 1 N0 2 00 CH3
C
0 0 0 0* 0 0 0
S
o~z* 0050/43197 01 114 4.394 4.395 0
H
3 a
C.
a a *0~ a. Ca C.
aec a a. a a a C C a a. a Co. O*Z. 0050/43197 115 No.0 R phys. data 4.397 11 -CH 3
CH-)
4.398 -0 K. CH 3
'CH
3 0 i
CH
3
A
C C C C C C C C C C C C C C C. 9 O.Z. 0050/43197 116 No. R..2 phys. data 4.400 -0
N-N
CH
3 4.401 -0 N -N
CH
3
CH
3 C* C. O.Z. 0050/43197 117 No. 0 R2phys. data R (R<3 4.402 -0 H of 0 4.403 -0 H 0
N
CH
3 O.Z. 0050/43197 W 118 The novel compounds are suitable as fungicides and insecticides.
The fungicidal and insecticidal compounds according to the invention, or agents containing them, may be applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting a'ents, or granules by sprayi--, atomizing, dusting, broadcasting or watering.
The forms of application depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribution of the active ingredients according to the invention as possible.
Normally, the plants are sprayed or dusted with the active ingredients, or the seeds of the plants are treated with the active ingredients.
he formulations are produced in known manner, for example S" by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to 25 employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics xylene), chlorinated aromatics chlorobenzenes), paraffins crude oil fractionsl, alcohols methanol, butanol), ketones cyclohexanone); amines ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals k5 slins, aluminas, talc and chalk) and ground synthetic mi -rals highly disperse silica and silirates); emulsifiers such as nonionic and anionic emulsifiers 35 polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as lignin-sulfite waste liquors and methylcellulose.
Examples of surfactants are: alkali metal, alkaline earth metal and ammornium salts of aromatic sulfonic acids, e.g., ligninsulfonic ecid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylaryl sulfonates, and alkyl, lauryl O.Z. 0050/43197 V 119 ether and fatty alcohol sulfates, and salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol pi,!t.'..Yol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methyl cellulose.
Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.
Granules, coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral E :ths such as silicic acids, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, 25 dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Sand ureas, and vegetable products such as grain meals, bark .meal, wood meal, and nutohell meal, cellulosic powders, etc.
Examples of formulations are as follows: I. A solution of 90 parts by weight of compound no. 1.52 and 10 parts by weight of N-methyl-a-pyrrolidone, which is 35 suitable for application in the form of very fine drops.
II. A mixture of 20 parts by weight of compound no. 1.56, 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 O.Z. 0050/43197 w 120 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.
III. An aqueous dispersion of 20 parts by weight of compound no. 1.98, 40 parts by weight of cyclohexanone, parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil.
IV. An aqueous dispersion of 20 parts by weight of compound no. 1.100, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210 and 2806C, and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil.
V. A hammer-milled mixture of 80 parts by weight of compound no. 2.52, 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a 20 sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained.
VI. An intimate mixture of 3 parts by weight of compound 25 no. 2.100 and 97 parts by weight of particulate kaolin. The dusc contains 3wt% of the active ingredient.
VII. An intimate mixture of 30 parts by weight of compound no. 1.52, 92 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 35 compound no. 1.56, 10 parts of the sodium salt of a phonolsulfonic 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. 1.98, 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 O,Z. 0050/43197 W 121 salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.
The 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.
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 compounds are applied by treating the fungi, or the seeds, plants, materials or the soil to be protected against fungus attack, with a fungicidally effective amount of the 20 active ingredients.
Application may be effected before or after infection of the materials, plants or seed by the fungi.
25 The compounds I 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 solani in cotton, 35 Ustilago species in cereals and sugar cane, Venturia inaequalis (scab) in apples, Helminthosporium species in cereals, Septoria nodorum in wheat, Bozrytis 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, O.Z. 0050/43197 S122 Fusarium and Verticillium species in various plants, Plasmopara viticola in grapes, Alternaria species in fruit and vegetables.
The novel compounds may also be used for protecting materials (timber), for example against Paecilomyces variotii.
The fungicidal agents generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt% of active ingredient.
When the active ingredients are used for treating seed, rates of from 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are generally required.
When the agents according to the invention are used as fungicides, they may be applied together with other active ingredients, for example herbicides, insecticides, growth regulators, other fungicides and fertilizers.
When mixed with other fungicides, the spectrum of fungicidal Saction is frequently increased.
Use examples 9 25 The active ingredients used for comparison purposes were methyl 2-[2-(phenyloxymethylene)-phenyl]-3-methoxyacrylate disclosed in EP 178 826 and 2-[2-(phenyloxymethylene)-phenyl]-glyoxylic acid methyl ester-0-methyloxime ether disclosed in EP 253 213.
Use Example Action on Plasmopara viticola Leaves of potted vines of the Muller-Thurgau variety were 35 sprayed with aqueous suspensions containing (dry basis) of active ingredient and 20% of emulsifier. To assess the duration of action, the plants were set up, after the sprayed-on layer had dried, for 8 days in the greenhouse.
Then the leaves were infected with a zoospore suspension of Plasmopara viticola. The plants were first placed for 48 hours in a water vapor-saturated chamber at 24 0 C and then in a greenhouse for 5 days at from 20 to 30°C. To accelerate and intensify the sporangiophore discharge, the plants were O.Z. 0050/43197 O 123 then again placed in the moist chamber for 16 hours. The extent of fungus attack was then assessed on the undersides of the leaves.
The results show that active ingredients 1,52, 1.56, 1.98, 1.100, 2,52 and 2.100, applied as spray liquors containing ppm of active ingredient, have a better fungicidal action than prior art comparative agents A and B *35
S
Claims (7)
- 2. A benzyl enol. ether of the formula II O.Z. 0050/43197 .00 CH 2 R Ii CH where R1, R 2 and R' are the radicals mentioned in claim 1.
- 3. A benzyl enol ether of the formula III III CH 3 0 2 C *5 Si S S S S. S 5 where R 2 and R 3 are the radicals mentioned in claim 1.
- 4. A benzyl enol ether of the formula IV N 0,CH3 R CH 3 Ol *.H S S where R1, R' and R 3 are the radicals mentioned in claim 1. S. A process for preparing a benzyl enol ether of the formula I as claimed in claim 1, which comprises reacting a benzyl derivative of the formula jc~ O.Z. 0050/43197 U VW in which U, V, W, A and B have the meaning mentioned in claim 1 and L is a leaving group, with an enol of the formula HO R2 1 H R3 in which R 1 R 2 and R 3 have the meaning mentioned in claim 1.
- 6. A fungicide containing an inert carrier and a fungicidally active amount of a benzyl enol ether of the formula I S. 5*55 Si S S S CS *S S a U V W where A is CH 2 CHC1, CH-C-C 4 -alkyll CH-O-C-C 4 -alkyl, CH-S-Cl-C4c O.Z. 0050/43197 alkyl, N-O-C-C 4 -alkyl, B is OH, C-C 4 -alkoxy, C-C 4 -alkylthio and Cl-C 4 -alkylamino, U, V and W are identical or different and are hydrogen, halogen, C,-C 4 -alkyl or C,-C 4 -alkoxy, R R 2and R 3 are identical or different and are hydrogen, cyano, halogen, NR R 5 C0 2 R CONR 4 COR S where n 0, 1 or 2, PO(0R 4 2 1 unbranched or branched Cl-C 1 0 -alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -CS- cycloalkyl-Cl-C 4 -alkyl C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 alkylthio-Cl-C,-alkyl, arylthio-C,-C 4 -alkyl, C 2 -C 6 -alkenyl, C 2 -C.-haloalkenyl, C 3 -C.-cycloalkenyl, C.-C 6 -halocyclo- alkenyl, C 2 -C 6 -alkynyl, Cl-C.-alkoxy, Cl-C 6 -haloalkoxy, Cl-C 4 -alkylthio, benzylthio, C,-C 4 -alkylcarbonyl, unsubstituted or substituted phenylcarbonyl, unsubstituted. or substituted benzylcarbonyl, CI-C 4 alkoxycarbonyl, unsubstituted or substituted 20 ehnxcroy, usbtttd o usiue :20 penyoxycarbonyl, unsubstituted or substitutedl unsubstituted or substituted aryloxy, unsubstituted or Ssubstituted arylthio, unsubstituted or substituted aryl- C-C 4 -alkyl, unsubstituted or substituted aryl-C 2 -C 4 alkenyl, unsubstituted or substituted aryloXY-Cl-'- 4 -alkyl, unsubstituted or substituted arylthio-C 1 -C 4 -alkyl, unsub- stituted or substituted hetaryl, unsubstituted or substi- tuted hetaryloxy, unsubstituted or substituted hetaryl- thio, unsubstituted or substituted heteroaryl-C,-C 4 -alkyl, unsubstituted or substituted hetaryl-C 2 -C 4 -alkenyl, *unsubstituted or substituted hetaryloxy-Cl-C 4 -alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyloxy, where unsubstituted or substituted, in addition to hydrogen, includes the radicals halogen, cyano, nitro, C 1 -C 4 -alI--fL, C 1 -C 4 -alkoxy, Cl-C 4 -haloalkyl, Cl-C 4 -halo- alkoxy, C,-C, 1 0 -alkoximino-C,-C 2 -alkyl, aryl, aryloxy, 0050/43197 ben, Yloxy, hetaryl, hetaryloxy, C 3 -CS-C'YCloalkyl, hatero- cyclyl, heterocyclyloxy, and the radicals R' and R are identical or different and are hydrogen, or C 1 -C 4 alkyl, R 1 and R 3 together, and also R' and R' together, in each case can form a carbocyclic or a heterocyclic ring which can in turn be benzo-fused and can be substituted by the radical mentioned under unsubstituted or substituted, where, inter alia, the following ring systems A -F are possible: the symbol is the group UV W C~ 0 A in the following 0 0 0 x 0 x C 0000,0 R -or RI x B* z 00OO 0 0 P. Y-X or xr jaI O.Z. 0050/43197 o2 R or 0 X z where X is CH 2 0, NR 4 Y is CH, where n 0, 1 or 2, Z is hydrogen, halogen, Ci-C 4 -alkyl or CI-C 4 -alkoxy and R 4 is *i 10 hydrogen or Ci-C 4 -alkyl and is a single bond or a double bond.
- 7. A method for controlling fungi, which comprises treating the fungi or the materials, plants, seeds or the 1 5 ground threatened by fungal attack with a fungicidally S 15 active amount of a compound of the formula I V W R I T where O.Z. 0050/43197 A is CH 2 CHCl, CH-C 1 -C 4 -alkyl, CH-O-C 1 -C 4 -alkyl, Cfl-S-C 1 -C 4 alkyl,, N-O-C 1 -C 4 B is OHf, Cl-C 4 -"lkoXY, Cl-C-alkyithio and C 1 -C 4 -81k:lamnino, U, V and W are identical or different and are hydrogen, halogen, C-C 4 -alkyl Or C 1 -C 4 -alkoxy, R 2 and R 3 are identical or different and are hydrogen, cyano, halogen, NR R C0 2 R 4 CONR R COR 4 r S where n 0, 1 or 2, PO(0R 4 2 1 unbranched or branched C,-Cl.-'alkyl, C 1 -C 4 haloalkyl, C 3 -C-cy-loalkyl, C 3 -C-halocycloalkyl, C3-C 6 cycloalkyl-Cl-C 4 -alkyl, C 1 -C 4 -alkoxy-Cj-C 4 -alkyl, C 1 -C 4 alkylthioC 1 -C 4 -alkyl, aryltho-Cl-C 4 -alkyl, C 2 -C--.lkenyl, C7 ,-1Lloa1lcenyl, C 3 -C 6 -CY'oalkenyl, C 3 -C-halocyclo- alke'.2l, C 2 -C-alkynyl, C,--C-alkoxy, C,-C-haloalkoxy, C,-C-alkyltbio, benzylthio, C-C 4 -alkylcarbonyl, 20 unsubstituted or substituted pheaylcarbonyl, unsubstituted or substituted benzylcarbonyl, CI-C 4 alkoxycarbonyl, unsubstituted or substituted 9phenoxycarbonyl, unsubstituted or substituted benzyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, unsubstituted or substituted aryithia, unsubstituted or substituted aryl- .9 C- 4 -alkyl, unsubstituted otr substituted arylC 2 -C 4 alkenyl, unsubstituted or suLkstituted aryloxy-Cl-C 4 -alkyl, unsubstituted or substituted arylthio-Cl-C 4 -alkyl, unsub- stituted or substituted hetaryl, unsubstituted or substi- 30 tuted hetaryloxy, unsubstituted or substituted hetaryl- thio, unsubstituted oi: substituted heteroaryl-C 1 -C 4 -alkylf *unsubstituted or substituted hetaryl-C 2 -C 4 -alkenyl, unsubstituted or substituted hetaryloxy-Cj-2 4 %-alkyl, unsubstituted or substitutad heterocyclyl, unsubstituted or substituted heterocyclyloxy, where unstbstituted or substituted, in~ addition to hydrogen, includes the radicals halogen, cyano, nitro, I~i' 0050/43197 C 1 -C 4 -alkyl, Cl-C, 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -halo- alkoxy, C 1 -C,,-alkoximino-C 1 -C 2 -alkylt aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, C 3 -C 6 -CYCloalkyl, hetero- cyclyl, heterocyclyloxy, and the radicals R 4 and R' are identical or different and are hydrogen or CI-C 4 alkyl, R3, and R 3 together, and also R 2 and R 3 together, in each case c&n form a carbocyclic or a heterocyclic ring which can i turn be benzo-fused aend can be substituted by the radical mentioned under unsubstituted or substituted, where, inter alia, the following ring systems A -F are possible: the symbol Q- is the group VW fH2 a0 0 x 0 000,. B 0R O.Z. 0050/43197 00,0 R1 or 00"0 R2 Y-x x z 2ro 0R 0 R 0xor 0 x z where X is CH 2 0, NR', Y is CH, (CH 2 where n 1 or 2, @54 Z is 4. @4hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy and o 4 10 R 4 is *hydrogen or C,-C 4 -alkyl and is a single bond or a *4 44double bond.
- 8. A compound of the formula I as claimed in claim 1, wherein A is CHOCH 3 B is OCH 3 U, V, W and R' are 15 hydroge~n, R 2 is cyano and R' is 2-f luorophenyl. seen
- 9. A compound of the formula I as claimed in claim "oo 1, wherein A is CHOCH 3 B is OCH 3 1 U, V, W and R1 are 4. C hydrogen, R 2 is -,yano and R 3 is 4-methylpheny'l. 20 10. A compound of the formula I as claimed in claim 1, wherein A is NOCH 3 B is OCH 3 1 U, V, W and R 1 are hydrogen, R' is cyano and R 3 is 2-f luorophenyl. DATED this 28th day of April 1993. BASF AKIENGESELLSCHAFT2 WATERMARK PATENT TRADEMvARK ATTORNEYS "THE ATRIUM" 290 BURWXD ROAD HAWTHORN. VIC. 3122. 0050/43197 Novel benzyl enol ethers and their use as crop protection agents ABSTRACT OF THE DISCLOSURE: Benzyl enol ether derivatives of the general formula I tyVW I R 2 R 0R. A Ce B where A is CH 2 CHC1, CH-alkyl, CH-O-alkyl, CH-S-alkyl or N-O-alkikl, B ~:is OH, alkoxy, alkylthio and alkylamino, U, V and W are identical or different and each is hydrogen, halogen, alkyl or alkoxy, R1, R 2 and R 3 are identical or different and each is hydrogen, cyano, ha- logen, amino, ester, amide, acyl, S(O),p 4 PO(0R 4 2 alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkyl-alkyl, al- koxy-alkyl, alkylthio-alkyl, arylthio-alkyl, alkenyl, halo- alkenyl, cycloalkenyl, halocycloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, benzylthio, alky~.carbonyl, substitu- ted or unsubstituted phenylcarbonyl, substituted or unst'b- stituted benzylcarbonyl, alkoxycarbonyl, substituted or un- substituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, substituted or unsubstituted aryl, sub- stituted or unsubstituted aryloxy, substituted or unsubsti- O.Z. 0050/43107 tuted arylthio, substituted or unsubstituted arylalkyl, sub- stituted or umsubstituted arylalkenyl, substituted or unsub- stituted aryloxyalkyl, substituted or unsubstituted aryl- thioalkyl, suistituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted hetarylalkenyl, substituted or unsubstituted hetaryloxyalkyl, substituted or unsubstituted heterocycilyl or substituted or unsubstituted heterocycly- loxy, and is hydrogen or C 1 -C 4 -alkyl, R1 and R 3 together, and R 2 and R 3 together, may f orm a carbo- cyclic or heterocyclic ring which in turn can be benzo-fused and can be substituted, and fungicides containing these corn- pounds.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4214189 | 1992-04-30 | ||
| DE4214189 | 1992-04-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3822793A AU3822793A (en) | 1993-11-04 |
| AU658291B2 true AU658291B2 (en) | 1995-04-06 |
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ID=6457794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU38227/93A Ceased AU658291B2 (en) | 1992-04-30 | 1993-04-29 | Novel benzyl enol ethers and their use as crop protection agents |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0567828B1 (en) |
| JP (1) | JPH0680621A (en) |
| KR (1) | KR930021610A (en) |
| AT (1) | ATE133405T1 (en) |
| AU (1) | AU658291B2 (en) |
| CA (1) | CA2094359A1 (en) |
| DE (1) | DE59301487D1 (en) |
| DK (1) | DK0567828T3 (en) |
| ES (1) | ES2083217T3 (en) |
| GR (1) | GR3019251T3 (en) |
| HU (1) | HU213728B (en) |
| IL (1) | IL105357A (en) |
| NZ (1) | NZ247514A (en) |
| TW (1) | TW237377B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU681932B2 (en) | 1994-02-04 | 1997-09-11 | Basf Aktiengesellschaft | Phenyl acetic acid derivatives, process and intermediate products for their production and agents containing them |
| DE59506765D1 (en) * | 1994-07-06 | 1999-10-14 | Basf Ag | Pyrazolyl derivatives, their preparation and their use as pesticides |
| DE10135466A1 (en) * | 2001-07-20 | 2003-02-06 | Bayer Cropscience Ag | Biphenyl-substituted 4-hydroxy-quinolones |
| CN1310899C (en) * | 2003-11-11 | 2007-04-18 | 沈阳化工研究院 | Benzopyrone compounds with pest killing and sterilizing activity and preparation and use |
| KR101412719B1 (en) | 2007-07-17 | 2014-06-26 | 후지필름 가부시키가이샤 | Photosensitive compositions, curable compositions, novel compounds, photopolymerizable compositions, color filters, and planographic printing plate precursors |
| CN101349865B (en) * | 2007-07-17 | 2012-10-03 | 富士胶片株式会社 | Photosensitive compositions, curable compositions, color filters, and method for manufacturing the same |
| CN108640896B (en) * | 2018-04-09 | 2019-07-02 | 陕西科技大学 | A kind of Desertorin B and its extracting method and application |
| CN112209910B (en) * | 2020-07-03 | 2023-10-17 | 贵州大学 | Myricetin derivative containing sulfonyl piperazine, preparation method and application |
| IL312547A (en) | 2021-11-02 | 2024-07-01 | Flare Therapeutics Inc | Pparg inverse agonists and uses thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0253213A1 (en) * | 1986-07-16 | 1988-01-20 | BASF Aktiengesellschaft | Oximethers and fungicides containing them |
| EP0513580A2 (en) * | 1991-05-17 | 1992-11-19 | BASF Aktiengesellschaft | Alpha-phenyl-acrylic acid derivatives, process for their preparation and their use as parasiticides and fungicides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ213630A (en) * | 1984-10-19 | 1990-02-26 | Ici Plc | Acrylic acid derivatives and fungicidal compositions |
| ATE161007T1 (en) * | 1990-06-27 | 1997-12-15 | Basf Ag | O-BENZYL OXIMETHERS AND PLANT PROTECTION PRODUCTS CONTAINING THESE COMPOUNDS |
-
1993
- 1993-04-09 IL IL105357A patent/IL105357A/en not_active IP Right Cessation
- 1993-04-13 AT AT93105924T patent/ATE133405T1/en not_active IP Right Cessation
- 1993-04-13 DK DK93105924.0T patent/DK0567828T3/en active
- 1993-04-13 EP EP93105924A patent/EP0567828B1/en not_active Expired - Lifetime
- 1993-04-13 ES ES93105924T patent/ES2083217T3/en not_active Expired - Lifetime
- 1993-04-13 DE DE59301487T patent/DE59301487D1/en not_active Expired - Lifetime
- 1993-04-14 TW TW082102822A patent/TW237377B/zh active
- 1993-04-19 CA CA002094359A patent/CA2094359A1/en not_active Abandoned
- 1993-04-27 JP JP5100774A patent/JPH0680621A/en active Pending
- 1993-04-28 NZ NZ247514A patent/NZ247514A/en unknown
- 1993-04-29 AU AU38227/93A patent/AU658291B2/en not_active Ceased
- 1993-04-29 HU HU9301255A patent/HU213728B/en not_active IP Right Cessation
- 1993-04-29 KR KR1019930007284A patent/KR930021610A/en not_active Application Discontinuation
-
1996
- 1996-03-07 GR GR960400648T patent/GR3019251T3/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0253213A1 (en) * | 1986-07-16 | 1988-01-20 | BASF Aktiengesellschaft | Oximethers and fungicides containing them |
| EP0513580A2 (en) * | 1991-05-17 | 1992-11-19 | BASF Aktiengesellschaft | Alpha-phenyl-acrylic acid derivatives, process for their preparation and their use as parasiticides and fungicides |
Also Published As
| Publication number | Publication date |
|---|---|
| KR930021610A (en) | 1993-11-22 |
| EP0567828A3 (en) | 1994-01-05 |
| CA2094359A1 (en) | 1993-10-31 |
| ES2083217T3 (en) | 1996-04-01 |
| JPH0680621A (en) | 1994-03-22 |
| NZ247514A (en) | 1995-03-28 |
| GR3019251T3 (en) | 1996-06-30 |
| HU213728B (en) | 1997-09-29 |
| IL105357A0 (en) | 1993-08-18 |
| ATE133405T1 (en) | 1996-02-15 |
| EP0567828B1 (en) | 1996-01-24 |
| TW237377B (en) | 1995-01-01 |
| AU3822793A (en) | 1993-11-04 |
| IL105357A (en) | 1997-07-13 |
| DK0567828T3 (en) | 1996-05-20 |
| EP0567828A2 (en) | 1993-11-03 |
| HU9301255D0 (en) | 1993-08-30 |
| HUT64176A (en) | 1993-12-28 |
| DE59301487D1 (en) | 1996-03-07 |
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