DE3310148A1 - HETEROCYCLIC COMPOUNDS - Google Patents
HETEROCYCLIC COMPOUNDSInfo
- Publication number
- DE3310148A1 DE3310148A1 DE19833310148 DE3310148A DE3310148A1 DE 3310148 A1 DE3310148 A1 DE 3310148A1 DE 19833310148 DE19833310148 DE 19833310148 DE 3310148 A DE3310148 A DE 3310148A DE 3310148 A1 DE3310148 A1 DE 3310148A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrazinyl
- alkyl
- pyridyl
- acetophenone
- dichloro
- 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.)
- Withdrawn
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 64
- -1 3-pyridyl-1-oxide Chemical group 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 26
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 150000002923 oximes Chemical class 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 150000002576 ketones Chemical class 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 238000009472 formulation Methods 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 241000233866 Fungi Species 0.000 claims description 8
- 239000000417 fungicide Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 230000000855 fungicidal effect Effects 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 238000003898 horticulture Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- HVLOGZQCPYKVCW-UHFFFAOYSA-N 2-bromo-1-(2,4-dichlorophenyl)-N-methoxy-2-pyridin-3-ylethanimine Chemical compound CON=C(C(C=1C=NC=CC1)Br)C1=C(C=C(C=C1)Cl)Cl HVLOGZQCPYKVCW-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- JXJZOKLCMIXNMF-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylpent-4-en-1-imine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=NOC)C(CC=C)C1=CC=CN=C1 JXJZOKLCMIXNMF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- JHNRZXQVBKRYKN-VQHVLOKHSA-N (ne)-n-(1-phenylethylidene)hydroxylamine Chemical class O\N=C(/C)C1=CC=CC=C1 JHNRZXQVBKRYKN-VQHVLOKHSA-N 0.000 claims description 2
- GQJAYZZANCJTRS-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-methoxy-2-(5-methylpyrazin-2-yl)ethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=NOC)CC1=CN=C(C)C=N1 GQJAYZZANCJTRS-UHFFFAOYSA-N 0.000 claims description 2
- UXZQRFIAFDLIGK-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-phenoxy-2-pyridin-3-ylethanimine Chemical compound ClC1=CC(Cl)=CC=C1C(CC=1C=NC=CC=1)=NOC1=CC=CC=C1 UXZQRFIAFDLIGK-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- GUONMLMNDCJQAB-UHFFFAOYSA-N [[1-(2,4-dichlorophenyl)-2-pyridin-3-ylethylidene]amino] benzoate Chemical compound ClC1=CC(Cl)=CC=C1C(CC=1C=NC=CC=1)=NOC(=O)C1=CC=CC=C1 GUONMLMNDCJQAB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- ULDCHQMBTGXQBB-UHFFFAOYSA-N n-methoxy-1-(4-nitrophenyl)-2-pyridin-3-ylethanimine Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(=NOC)CC1=CC=CN=C1 ULDCHQMBTGXQBB-UHFFFAOYSA-N 0.000 claims description 2
- IWEFODGCIUREIH-UHFFFAOYSA-N n-methoxy-2-pyrazin-2-yl-1-[4-(trifluoromethyl)phenyl]ethanimine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(=NOC)CC1=CN=CC=N1 IWEFODGCIUREIH-UHFFFAOYSA-N 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- RCBNSTYDRPXTSU-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)-n-methoxy-2-pyrazin-2-ylethanimine Chemical compound C=1C(Cl)=CC=C(Cl)C=1C(=NOC)CC1=CN=CC=N1 RCBNSTYDRPXTSU-UHFFFAOYSA-N 0.000 claims 2
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims 1
- MRNNJQKWCNASEC-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n-methoxy-2-pyrazin-2-ylethanimine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=NOC)CC1=CN=CC=N1 MRNNJQKWCNASEC-UHFFFAOYSA-N 0.000 claims 1
- LBUNTWYSZNEBQK-UHFFFAOYSA-N 1-(3-chlorophenyl)-n-methoxy-2-pyrazin-2-ylethanimine Chemical compound C=1C=CC(Cl)=CC=1C(=NOC)CC1=CN=CC=N1 LBUNTWYSZNEBQK-UHFFFAOYSA-N 0.000 claims 1
- MUDCZCFCURGFHV-UHFFFAOYSA-N 1-(4-chloro-2-methoxyphenyl)-n-methoxy-2-pyrazin-2-ylethanimine Chemical compound C=1C=C(Cl)C=C(OC)C=1C(=NOC)CC1=CN=CC=N1 MUDCZCFCURGFHV-UHFFFAOYSA-N 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- BNLQSILCISLZBJ-UHFFFAOYSA-N C(C=CC)(=O)ON=C(CC=1C=NC=CC1)C1=C(C=C(C=C1)Cl)Cl Chemical compound C(C=CC)(=O)ON=C(CC=1C=NC=CC1)C1=C(C=C(C=C1)Cl)Cl BNLQSILCISLZBJ-UHFFFAOYSA-N 0.000 claims 1
- 150000002443 hydroxylamines Chemical class 0.000 claims 1
- XUQBNWNCMBROPZ-UHFFFAOYSA-N n-methoxy-1-(4-methoxyphenyl)-2-pyrazin-2-ylethanimine Chemical compound C=1C=C(OC)C=CC=1C(=NOC)CC1=CN=CC=N1 XUQBNWNCMBROPZ-UHFFFAOYSA-N 0.000 claims 1
- DPCNQJBGJKTRRH-UHFFFAOYSA-N n-methoxy-1-phenyl-2-pyrazin-2-ylethanimine Chemical compound C=1C=CC=CC=1C(=NOC)CC1=CN=CC=N1 DPCNQJBGJKTRRH-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 239000003921 oil Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000002270 dispersing agent Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 241000221785 Erysiphales Species 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 150000004292 cyclic ethers Chemical class 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WUYTZBFFXRNJSB-UHFFFAOYSA-N 1-phenyl-2-pyrazin-2-ylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CN=CC=N1 WUYTZBFFXRNJSB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- BVUNKIYUJIIEEX-UHFFFAOYSA-N n-[1-(2,4-dichlorophenyl)-2-pyridin-3-ylethylidene]hydroxylamine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=NO)CC1=CC=CN=C1 BVUNKIYUJIIEEX-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- CGZQCZNRBCLEOH-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-pyridin-3-ylethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)CC1=CC=CN=C1 CGZQCZNRBCLEOH-UHFFFAOYSA-N 0.000 description 2
- LHXLYCTZKAOAPX-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-methoxyimino-1-pyridin-3-ylethanol Chemical compound CON=C(C(O)C=1C=NC=CC1)C1=C(C=C(C=C1)Cl)Cl LHXLYCTZKAOAPX-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- CUKYGXFNZUNZLN-UHFFFAOYSA-N n-[1-(2,4-dichlorophenyl)-2-pyrazin-2-ylethylidene]hydroxylamine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=NO)CC1=CN=CC=N1 CUKYGXFNZUNZLN-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- ZZAXSKXALNKDRJ-UHFFFAOYSA-N o-[(2,6-dichlorophenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.NOCC1=C(Cl)C=CC=C1Cl ZZAXSKXALNKDRJ-UHFFFAOYSA-N 0.000 description 1
- DBTXKJJSFWZJNS-UHFFFAOYSA-N o-phenylhydroxylamine;hydrochloride Chemical compound Cl.NOC1=CC=CC=C1 DBTXKJJSFWZJNS-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000417 polynaphthalene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- 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
- 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
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Description
worinwherein
25 30 3525 30 35
Pa/31.1.83Pa / 1/31/83
unsubstituiertes oder mono-, di- oder trisubstituiertes Phenyl bedeutet, wobei die gegebenenfalls vorhandenen Substituenten aus 1 bis 3 Halogenatomen, 1 bis 3. C, 3~Alkylgruppen, 1 oder 2 C, ^-Alkoxygruppen, einer Trifluormethylgruppe, einer Cyanogruppe und einer Nitrogruppe ausgewählt sind, 3-Pyridyl, 3-Pyridyl-l-oxid, 2-Pyrazinyl, 2-Pyrazinyl-l-oxid, 2-Pyrazinyl-4-oxid, 2-Pyrazinyl-l,4-dioxid, 5-Pyrimi· dinyl, 5-Pyrimidinyl-l-oxid, 5-Pyrimidinyl-3-oxid oder 5-Pyrimidinyl-l,3-dioxid bedeutet, wobei die vorgenanntendenotes unsubstituted or mono-, di- or trisubstituted phenyl, the substituents optionally present consisting of 1 to 3 halogen atoms, 1 to 3 C, 3 ~ alkyl groups, 1 or 2 C, ^ alkoxy groups, a trifluoromethyl group, a cyano group and a nitro group are selected, 3-pyridyl, 3-pyridyl-1-oxide, 2-pyrazinyl, 2-pyrazinyl-1-oxide, 2-pyrazinyl-4-oxide, 2-pyrazinyl-1,4-dioxide, 5-pyrimidinyl , 5-pyrimidinyl-1-oxide, 5-pyrimidinyl-3-oxide or 5-pyrimidinyl-1, 3-dioxide means, the aforementioned
Gruppen auch mit Methyl, Methoxy oder Chlor substituiert sein können, R Wasserstoff, C,_.-Alkyl, C,- oder C.-Alkenyl, C3- oder C.-Alkinyl, Chlor, Brom oder Hydroxy bedeutetGroups may be also substituted with methyl, methoxy or chlorine, R is hydrogen, C _.- alkyl, C, - or C-alkenyl, C 3 - or C-alkynyl, chlorine, bromine or hydroxy
4
und R eine Gruppe4th
and R is a group
5 » 65 »6
OR (a) oder OCR (b)OR (a) or OCR (b)
darstellt, worinrepresents where
R unsubstituiertes oder mit Halogen,R unsubstituted or with halogen,
C1 .,-Alkoxy oder Cyano monosubstitu-C 1. , - alkoxy or cyano monosubstitu-
iertes C, ,-Alkyl; C-, ,-Cycloalkyl;C 1 -C 8 -alkyl; C-, C- cycloalkyl;
C-, .-Alkenyl; C, ,.-Alkinyl; oder unsubstituiertes oder im Arylkern mono-, di-C-,. -Alkenyl; C 1, - alkynyl; or unsubstituted or mono-, di-
oder trisubstituiertes Aryl-C- ,-alkyl oder Aryl ist, wobei die gegebenenfalls vorhandenen Substituenten aus 1 bis Halogenatomen, einer C. ,-Alkylgruppe, einer C» 3~Alkoxygruppe und 1 bis 3or tri-substituted aryl-C, alkyl, or aryl, wherein the optional substituents are from 1 to halogen atoms, a C., alkyl group, a C "3 ~ alkoxy group and 1 to 3
Nitrogruppen ausgewählt sind, R unsubstituiertes oder mit Halogen,Nitro groups are selected, R unsubstituted or with halogen,
C, ,-Alkoxy oder Cyano monosubstituiertes C- ,-Alkyl; unsubstituiertes oder im Arylkern mono-, di- oder trisubC1, -Alkoxy or cyano monosubstituted C-, -alkyl; unsubstituted or mono-, di- or trisub in the aryl nucleus
stituiertes Aryl-C. ,-alkyl; C,_,-Cycloalkyl; C- ,--Alkenyl; unsubstituiertes oder mono-, di- oder trisubstituiertes Aryl; unsubstituiertes oder im Arylkern mono-, di- oder trisubstisubstituted aryl-C. , -alkyl; C 1-6 cycloalkyl; C-, - alkenyl; unsubstituted or mono-, di- or trisubstituted aryl; unsubstituted or mono-, di- or trisubsti in the aryl nucleus
tuiertes Aryloxy-C._3~alkyl; C- ,-Alkoxy; C, ,-Alkylamino; oder Di(C, ,-alkyl)amino ist, wobei die im Arylkern gegebenenfalls vorhandenen Substituenten aus 1 bis 3 Halogenatomen, einertuiertes aryloxy c._ ~ 3 alkyl; C-, alkoxy; C,, -alkylamino; or di (C, alkyl) amino, the substituents optionally present in the aryl nucleus consisting of 1 to 3 halogen atoms, one
C, 3~Alkylgruppe, einer C, -Alkoxygruppe und 1 bis 3 Nitrogruppen ausgewählt sind, und X Sauerstoff oder Schwefel bedeutet,C, 3 ~ alkyl group, a C, alkoxy group and 1 to 3 nitro groups are selected, and X is oxygen or sulfur,
IUIU
mit der Massgabe, dass, falls gleichzeitig R mit 1with the proviso that, if at the same time R and 1
2 bis 3 Halogenatomen substituiertes Phenyl, R 3-Pyridyl, 3-Pyridyl-l-oxid, 2-Pyrazinyl, 2-Pyrazinyl-l-oxid, 2-Pyrazinyl-4-oxid oder 2-Pyrazinyl-l,4-dioxid, R2 to 3 halogen atoms substituted phenyl, R 3-pyridyl, 3-pyridyl-l-oxide, 2-pyrazinyl, 2-pyrazinyl-l-oxide, 2-pyrazinyl-4-oxide or 2-pyrazinyl-1,4-dioxide, R
44th
Wasserstoff oder C1 .-Alkyl, R eine Gruppe (a) und R unsubstituiertes C1 ,-Alkyl, C_ ,.-Cycloalkyl, C0 ,-Alkenyl oder C, ,.-Alkinyl bedeuten, R nur 3-Halophenyl, 2,3-, 2,5-, 3,4- oder 3,5-Dihalophenyl oder 2,3,4-, 2,3,5- oder 2,4,5-Trihalophenyl sein kann, und Säureadditionssalze dieser Verbindungen.Is hydrogen or C. 1-alkyl, R is a group (a) and R is unsubstituted C 1 alkyl, C_, .- cycloalkyl, C 0, alkenyl or C, mean .- alkynyl, R a 3-halophenyl, 2 , 3-, 2,5-, 3,4- or 3,5-dihalophenyl or 2,3,4-, 2,3,5- or 2,4,5-trihalophenyl, and acid addition salts of these compounds.
Die Verbindungen der Formel I und deren Säureadditionssalze besitzen fungizide Eigenschaften und eignen sich als fungizide Wirkstoffe, insbesondere zur Verwendung in der Landwirtschaft und im Gartenbau.The compounds of the formula I and their acid addition salts have fungicidal properties and are suitable as fungicidal active ingredients, in particular for use in agriculture and horticulture.
Die Erfindung betrifft ferner ein Verfahren zur Herstellung der Verbindungen der Formel I und ihrer Säureadditionssalze, Verbindungen der Formel I und Säureadditionssalze davon als fungizide Wirkstoffe, fungizide Mittel, die Verbindungen der Formel I oder Säureadditionssalze davon als Wirkstoffe enthalten, sowie die Verwendung solcher Verbindungen, Säureadditionssalze und Mittel zur Bekämpfung von Fungi in der Landwirtschaft und im Gartenbau.The invention also relates to a method of production of the compounds of the formula I and their acid addition salts, compounds of the formula I and acid addition salts thereof as fungicidal active ingredients, fungicidal agents, the compounds of the formula I or acid addition salts thereof Contain as active ingredients, as well as the use of such compounds, acid addition salts and agents for combating of fungi in agriculture and horticulture.
Der Ausdruck "Halogenatom", "Halogen" bzw. "Halo" in der obigen Definition der Formel I umfasst Fluor, Chlor, Brom und Jod, wobei Chlor und Brom, insbesondere Chlor, bevorzugt sind. Im Falle von zwei oder drei Halogenatomen als Substituenten derselben Phenyl- bzw. Arylgruppe können diese gleich oder verschieden sein.The term "halogen atom", "halogen" or "halo" in the above definition of formula I includes fluorine, chlorine, Bromine and iodine, with chlorine and bromine, especially chlorine, being preferred. In the case of two or three halogen atoms as substituents on the same phenyl or aryl group, these can be identical or different.
Die Ausdrücke "C1 3-Alkyl", "C1 4-Alkyl", "C1 6-Alkyl", 11C3- oder C4-Alkenyl", 11C3 6-Alkenyl" , "C2_6-Alkenyl" , "C,- oder C.-Alkinyl" und "C_ --Alkinyl" umfassen sowohlThe terms "C 1 3 alkyl", "C 1 4 alkyl", "C 1 6 alkyl", 11 C 3 - or C 4 -alkenyl ", 11 C 3 6 -alkenyl", "C 2 _ 6 -Alkenyl "," C1- or C.-alkynyl "and" C_ -alkynyl "include both
•J τ O ^m Ό• J τ O ^ m Ό
geradkettige als auch verzweigte Kohlenwasserstoffreste. Unter "Alkyl" sind je nach Anzahl der Kohlenstoffatome z.B. folgende Gruppen zu verstehen: Methyl, Aethyl, n-Propyl,straight-chain and branched hydrocarbon radicals. By "alkyl", depending on the number of carbon atoms, e.g. to understand the following groups: methyl, ethyl, n-propyl,
Isopropyl, η-Butyl, tert.Butyl, Isoamyl und n-Hexyl. Dies gilt auch für Alkylgruppen enthaltende Gruppen, wie "C, .,-Alkoxy", "C1-6-AIkOXy", Aryl-C1_3~alkyl" , "Aryloxy-C^^-Isopropyl, η-butyl, tert-butyl, isoamyl and n-hexyl. This also applies to groups containing alkyl groups, such as "C,., - alkoxy", "C 1-6 -AIkOXy", aryl-C 1 _ 3 ~ alkyl "," aryloxy-C ^^ -
alkyl", "C1 ,-Alkylamino" und "Di(C1 --alkyl)amino". In der ι—1> ι—οalkyl "," C 1 , -alkylamino "and" di (C 1 -alkyl) amino ". In the ι — 1> ι — ο
letzterwähnten Gruppe können die C, ß-Alkylgruppen gleich oder verschieden sein.The last-mentioned group, the C, ß- alkyl groups can be identical or different.
R in der Bedeutung C^- oder C.-Alkenyl bzw. C,- oder C.-Alkinyl ist vorzugsweise Allyl bzw. Propargyl. Bedeutet R C-. ,-Alkenyl bzw. R C0 ,.-Alkenyl, so ist dies vor-R in the meaning of C ^ - or C.-alkenyl or C, - or C.-alkynyl is preferably allyl or propargyl. Means R C-. , -Alkenyl or RC 0 , .- alkenyl, this is primarily
O —O £. — DO - O £. - D
zugsweise Allyl (2-Propenyl) bzw. Vinyl oder 1-Propenyl.preferably allyl (2-propenyl) or vinyl or 1-propenyl.
R in der Bedeutung C- fi-Alkinyl ist vorzugsweise Propargyl.R in the meaning of C- fi -alkynyl is preferably propargyl.
Der Ausdruck "Aryl" an sich oder als Teil von "Aryloxy" bedeutet vorzugsweise Phenyl, wobei auch heterocyclische Gruppen mit aromatischem Charakter, wie Pyridyl, Furyl und Thienyl, in Betracht kommen.The term "aryl" per se or as part of "aryloxy" means preferably phenyl, including heterocyclic Groups with an aromatic character, such as pyridyl, furyl and thienyl, come into consideration.
2
R bedeutet vorzugsweise gegebenenfalls substituiertes 3-Pyridyl, 2-Pyrazinyl oder 5-Pyrimidinyl, wie oben näher
definiert, insbesondere die unsubstituierten Gruppen.2
R preferably denotes optionally substituted 3-pyridyl, 2-pyrazinyl or 5-pyrimidinyl, as defined in more detail above, in particular the unsubstituted groups.
4
R stellt vorzugsweise eine Gruppe (a) dar.4th
R preferably represents a group (a).
Besonders bevorzugte Verbindungen der Formel I sind:Particularly preferred compounds of the formula I are:
2', 5·-Dichlor-2-(2-pyrazinyl)-acetophenon-O-methyloxim, 2-(2-Pyrazinyl)-4'-trifluormethyl-acetophenon-O-methyloxim, 2 ', 5-dichloro-2- (2-pyrazinyl) -acetophenone-O-methyloxime, 2- (2-pyrazinyl) -4'-trifluoromethyl-acetophenone-O-methyloxime,
2',4'-Dichlor-2-(3-pyridyl)-4-pentenophenon-O-methyloxim, 2 ', 4'-dichloro-2- (3-pyridyl) -4-pentenophenone-O-methyloxime,
2-Brom-2',4'-dichlor-2-(3-pyridyl)-acetophenon-O-methyloxim und2-bromo-2 ', 4'-dichloro-2- (3-pyridyl) acetophenone-O-methyloxime and
2',4'-Dichlor-2-(3-pyridyl)-glykolophenon-O-methyloxim.2 ', 4'-dichloro-2- (3-pyridyl) -glycolophenone-O-methyloxime.
Vertreter von Verbindungen der Formel I sind:Representatives of compounds of the formula I are:
2',4'-Dimethyl-2-(2"-pyrazinyl)-acetophenon-O-methyloxim-1"-oxid, 2 ', 4'-Dimethyl-2- (2 "-pyrazinyl) -acetophenone-O-methyloxime-1" -oxide,
2·,4'-Dichlor-2-(5-pyrimidinyl)-acetophenon-O-methyloxim, 2',4'-Dichlor-2-(5-pyrimidinyl)-acetophenon-O-allyloxim,2, 4'-dichloro-2- (5-pyrimidinyl) -acetophenone-O-methyloxime, 2 ', 4'-dichloro-2- (5-pyrimidinyl) -acetophenone-O-allyloxime,
IU IIU I
2',4'-Dichlor-2-(3-pyridyl)-acetophenon-O-methoxyacetyloxim, 2 ', 4'-dichloro-2- (3-pyridyl) -acetophenone-O-methoxyacetyloxime,
3', 5 '-Dichlor-2-(2-pyrazinyl)-acetophenon-O-cyclopentyloxim,
4'-Cyano-2-(3-pyridyl)-acetophenon-O-athyloxim,3 ', 5' -Dichlor-2- (2-pyrazinyl) -acetophenone-O-cyclopentyloxime,
4'-cyano-2- (3-pyridyl) -acetophenone-O-athyloxime,
2',4',5'-Trifluor-2-(2"-pyrazinyl)-butyrophenon-O-methyloxim-1",4"-dioxid, 2 ', 4', 5'-Trifluoro-2- (2 "-pyrazinyl) -butyrophenone-O-methyloxime-1", 4 "-dioxid,
3-Brom-2-(5-methoxy-3-pyfidyl)-propiophenon-0-(3-cyanopropy1)oxim, 3-bromo-2- (5-methoxy-3-pyfidyl) -propiophenone-0- (3-cyanopropy1) oxime,
2-(21-Pyrazinyl)-acetophenon-0-(2-chloräthyl)oxim-4'-oxid, 2- (2 1 -pyrazinyl) acetophenone-0- (2-chloroethyl) oxime-4'-oxide,
4'-Aethoxy-3'-methyl-2-(3"-pyridyl)-acetophenon-O-cyclohexyloxim-1"-oxid, 4'-ethoxy-3'-methyl-2- (3 "-pyridyl) -acetophenone-O-cyclohexyloxime-1" oxide,
3'-Chlor-2-(5"-pyrimidinyl)-propiophenon-O-propargyloxim-l"-oxid, 3'-chloro-2- (5 "-pyrimidinyl) -propiophenone-O-propargyloxime-1" oxide,
2■-Chlor-4'-trifluormethyl-2-(2"-methyl-5"-pyrimidinyl) · acetophenon-0-(2-phenyläthyl)oxim-1",3"-dioxid,2 ■ -Chlor-4'-trifluoromethyl-2- (2 "-methyl-5" -pyrimidinyl) · acetophenone-0- (2-phenylethyl) oxime-1 ", 3" -dioxide,
4'-(n-Propyl)-2-(5"-chlor-3"-pyridyl)-acetophenon-O-(4-methylphenyl)oxim-1"-oxid, 4 '- (n-Propyl) -2- (5 "-chloro-3" -pyridyl) -acetophenone-O- (4-methylphenyl) oxime-1 "oxide,
3',4'-Dimethoxy-2-(5-pyrimidinyl)-propiophenon-0-(4-nitrobenzyl)-oxim, 3 ', 4'-Dimethoxy-2- (5-pyrimidinyl) -propiophenone-0- (4-nitrobenzyl) -oxime,
2-(5"-Methoxy-2"-pyrazinyl)-acetophenon-0-(4-athoxy-3-methylbenzyl)oxim-4"-oxid, 2- (5 "-Methoxy-2" -pyrazinyl) -acetophenone-0- (4-athoxy-3-methylbenzyl) oxime-4 "-oxide,
2',4',5'-Trimethyl-2-(5"-pyrimidinyl)-acetophenon-O-[3-(2,4-dinitrophenyl)-propyl]oxim-3"-oxid, 2 ', 4', 5'-trimethyl-2- (5 "-pyrimidinyl) -acetophenone-O- [3- (2,4-dinitrophenyl) -propyl] oxime-3" -oxide,
2'-Chlor-4'-jod-2-(5-pyrimidinyl)-butyrophenon-O-C 2-(3,4,5-trichlorphenyl)-äthyl]oxim, 2'-chloro-4'-iodo-2- (5-pyrimidinyl) -butyrophenone-O-C 2- (3,4,5-trichlorophenyl) -ethyl] oxime,
2■,4■-Dichlor-2-(5-methyl-3-pyridyl)-acetophenon-O-chloracetyloxim, 2 ■, 4 ■ -Dichlor-2- (5-methyl-3-pyridyl) -acetophenone-O-chloroacetyloxime,
2'-Chlor-4 ' -trif luormethyl-2-( 2"-pyrazinyl) -propiophenon-0-(4-cyanobutyryl)oxim-1",3"-dioxid, 2-(2-Pyrazinyl)-acetophenon-O-(3-phenyl-propionyl)oxim,2'-chloro-4 '-trifluoromethyl-2- (2 "-pyrazinyl) -propiophenone-0- (4-cyanobutyryl) oxime-1", 3 "-dioxide, 2- (2-Pyrazinyl) -acetophenone-O- (3-phenyl-propionyl) oxime,
21-Methoxy-2-(3"-pyridyl)-acetophenon-0-(2,4-dichlorphenylacetyl)oxim-1"-oxid, 2 1 -Methoxy-2- (3 "-pyridyl) -acetophenone-0- (2,4-dichlorophenylacetyl) oxime-1" oxide,
4'-Nitro-2-(5-chlor-2-pyrazinyl)-acetophenon-O-C4-(4-äthoxyphenyl)-butyryl]oxim, 4'-Nitro-2- (5-chloro-2-pyrazinyl) -acetophenone-O-C4- (4-ethoxyphenyl) -butyryl] oxime,
2',4'-Dichlor-2-(5-pyrimidinyl)-acetophenon-0-thioacetyloxim, 2 ', 4'-dichloro-2- (5-pyrimidinyl) -acetophenone-0-thioacetyloxime,
3310U83310U8
4'-Cyano-2'-chlor-2-(3-pyridyl)-4-pentenophenon-O-(2,4-dichlorbenzoyl)oxim, 4'-cyano-2'-chloro-2- (3-pyridyl) -4-pentenophenone-O- (2,4-dichlorobenzoyl) oxime,
2-(4-Chlor-5-pyrimidinyl)-propiophenon-0-(3-phenoxypropionyl)oxim, 2- (4-chloro-5-pyrimidinyl) -propiophenone-0- (3-phenoxypropionyl) oxime,
2',4'-Dichlor-2-(3"-pyridyl)-acetophenon-0-(4-methylphenoxyacety1)oxim-l"-oxid, 2 ', 4'-dichloro-2- (3 "-pyridyl) -acetophenone-0- (4-methylphenoxyacety1) oxime-1" oxide,
3'-Methyl-2-(2-pyrazinyl)-acetophenon-0-[3-(2-nitro-4-propoxyphenoxy)-butyryl]oxim, 3'-methyl-2- (2-pyrazinyl) -acetophenone-0- [3- (2-nitro-4-propoxyphenoxy) -butyryl] oxime,
4'-Chlor-2-(6-methy1-2-pyrazinyl)-acetophenon-0-(n-ΊΟ butoxycarbonyl)oxim,4'-chloro-2- (6-methy1-2-pyrazinyl) -acetophenone-0- (n-ΊΟ butoxycarbonyl) oxime,
2-(5"-Pyrimidinyl)-acetophenon-O-iN-methylcarbamoyl)-oxim-i"-oxid und2- (5 "-Pyrimidinyl) -acetophenone-O-iN -methylcarbamoyl) -oxime-i" -oxide and
4'-Aethoxy-2-(5-pyrimidinyl)-acetophenon-O-CN,N-di-(n-pentyl)thiocarbamoyl]oxim. 4'-Ethoxy-2- (5-pyrimidinyl) acetophenone-O-CN, N-di (n-pentyl) thiocarbamoyl] oxime.
In den Verbindungen der Formel I können asymmetrischeIn the compounds of the formula I, asymmetric
Kohlenstoffatome vorhanden sein, so dass die Verbindungen als optische Antipoden vorliegen können. Durch das Vorliegen der C=N-Doppelbindung und gegebenenfalls auch einer aliphatischen C=C-Doppelbindung tritt geometrische Isomerie auf. Die Formel I soll demnach all diese möglichen isomeren Formen umfassen.Carbon atoms exist, making connections can exist as optical antipodes. By the presence of the C = N double bond and possibly also one aliphatic C = C double bond, geometric isomerism occurs on. The formula I is therefore intended to encompass all of these possible isomeric forms.
Als Säureadditionssalze der Verbindungen der Formel I kommen physiologisch verträgliche Salze in Frage. Hierzu gehören vorzugsweise Salze der Verbindungen I mit anorganischen oder organischen Säuren wie Salzsäure, Salpetersäure, Phosphorsäure, mono- und bifunktionellen Carbonsäuren und Hydroxycarbonsäuren, z.B. Essigsäure, Maleinsäure, Bernsteinsäure, Fumarsäure, Weinsäure, Zitronensäure, Salicylsäure, Sorbinsäure und Milchsäure, und Sulfonsäuren, z.B. 1,5-Naphthalin-disulfonsäure. Im Falle der N-Oxide, d.h. der Verbindungen der Formel I, worinAs acid addition salts of the compounds of formula I Physiologically compatible salts come into question. These preferably include salts of the compounds I with inorganic ones or organic acids such as hydrochloric acid, nitric acid, phosphoric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, e.g. acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, Salicylic acid, sorbic acid and lactic acid, and sulfonic acids, e.g. 1,5-naphthalenedisulfonic acid. In the event of the N-oxides, i.e. the compounds of the formula I, in which
2
R unsubstituiertes oder mit Methyl, Methoxy oder Chlor substituiertes 3-Pyridyl-l-oxid, 2-Pyrazinyl-l-oxid,
-4-oxid und -1,4-dioxid, und 5-Pyrimidinyl-l-oxid, -3-oxid
und -1,3-dioxid bedeutet, kommen als Säureadditionssalze insbesondere physiologisch verträgliche Salze mit starken2
R 3-pyridyl-1-oxide, 2-pyrazinyl-1-oxide, -4-oxide and -1,4-dioxide, and 5-pyrimidinyl-1-oxide, -3- unsubstituted or substituted by methyl, methoxy or chlorine Oxide and -1,3-dioxide mean, acid addition salts are in particular physiologically compatible salts with strong ones
ό IU I H ό IU I H
Säuren in Frage, wie anorganischen Säuren, z.B. Salzsäure, Salpetersäure und Phosphorsäure, und Sulfonsäuren, z.B. 1,5-Naphthalindisulfonsäure.Acids such as inorganic acids, e.g. hydrochloric acid, nitric acid and phosphoric acid, and sulfonic acids, e.g. 1,5-naphthalenedisulfonic acid.
Das erfindungsgemässe Verfahren zur Herstellung der Verbindungen der allgemeinen Formel I und von deren- Säureadditionssalzen ist dadurch gekennzeichnet, dass manThe process according to the invention for the preparation of the compounds of general formula I and their acid addition salts is characterized by the fact that one
a) ein Oxim der allgemeinen Formel
10a) an oxime of the general formula
10
R3'R 3 '
1 < 2'1 <2 '
R C CH R IIR C CH R II
IlIl
LhLh
worin R die oben angegebene Bedeutung besitzt,where R has the meaning given above,
2'2 '
R 3-Pyridyl, 2-Pyrazinyl oder 5-Pyrimidinyl bedeutet, wobei die vorgenannten Gruppen auch mit Methyl, Methoxy oder Chlor substituiert sein können, und R ' die oben angegebene Bedeutung von RR 3-pyridyl, 2-pyrazinyl or 5-pyrimidinyl means, the aforementioned groups also with methyl, methoxy or Chlorine can be substituted, and R 'has the meaning given above for R
ausser Chlor, Brom oder Hydroxy bedeutet,
mit einer Verbindung der allgemeinen Formelmeans apart from chlorine, bromine or hydroxyl,
with a compound of the general formula
R5*Y IIIR 5 * Y III
''
worin R die oben angegebene Bedeutung von R ausser gegebenenfalls substituiertem Aryl besitztwherein R has the abovementioned meaning of R except optionally substituted Aryl possesses
und Y eine Abgangsgruppe, z.B. Chlor, Brom,and Y is a leaving group, e.g. chlorine, bromine,
Jod, Mesyloxy oder Tosyloxy, insbesondere Chlor, Brom oder Jod, bedeutet,Means iodine, mesyloxy or tosyloxy, in particular chlorine, bromine or iodine,
bzw. mit einem reaktionsfähigen Derivat einer Säure der allgemeinen Formelor with a reactive derivative of an acid of the general formula
6 H6 H.
R COH IVR COH IV
:.·:·:":.': 3310H8:. ·: ·: ":. ': 3310H8
m * mm ·« »I m * mm · «» I.
-Ά-Ά
worin R und X die oben angegebenen Bedeutungenwherein R and X have the meanings given above
besitzen,own,
wie einem Säurehalogenid, insbesondere dem Säurechlorid oder Säurebromid, dem Säureanhydrid oder, falls R C- ,-Alkylamino bedeutet, dem (C, _fi-Alkyl)isocyanat bzw. -isothiocyanat, umsetzt,as an acid halide, especially the acid chloride or acid bromide, acid anhydride, or, if R C, alkylamino is, the (C, _ fi alkyl) isocyanate or isothiocyanate is reacted,
b) ein Keton der allgemeinen Formelb) a ketone of the general formula
R3'R 3 '
1 I 2' R C CH R V1 I 2 'R C CH R V
Il OIl O
1 2' 3'1 2 '3'
worin R , R und R die oben angegebenen Bedeutungen besitzen, mit einem O-substituierten Hydroxylamin der allgemeinen Formelwherein R, R and R have the meanings given above, with an O-substituted hydroxylamine of the general formula
r5"onh2 vir 5 "onh 2 vi
5"5 "
worin R die oben angegebene Bedeutung von Rwherein R has the meaning given above for R
ausser C3_fi-Alkinyl bedeutet, umsetzt,except C 3 _ fi -alkynyl means, converts,
c) ein substituiertes Acetophenonoxim der allgemeinen Formelc) a substituted acetophenone oxime of the general formula
1 21 1 2 1
Il Il 22
R4 R 4
12' 412 '4
worin R , R und R die oben angegebenen Bebedeutungen besitzen,where R, R and R have the meanings given above,
mit einem Chlorierungs- oder Bromierungsmittel behandelt, 35treated with a chlorinating or brominating agent, 35
d) ein Keton der allgemeinen Formeld) a ketone of the general formula
J J ι υ ιJ J ι υ ι
VIIVII
12' 412 '4
worin R , R und R die oben angegebenen Bedeutungen besitzen, mit einem Reduktionsmittel behandelt, oderwherein R, R and R have the meanings given above, treated with a reducing agent, or
e) ein Pyridin-, Pyrazin- bzw. Pyrimidin-Derivat der allgemeinen Formele) a pyridine, pyrazine or pyrimidine derivative of general formula
R3 R 3
R C CH R ' I"R C CH R 'I "
IlIl
U
R U
R.
1 2' 3 4 worin R , R ,R und R die oben angegebenen1 2 '3 4 wherein R, R, R and R are as given above
Bedeutungen besitzen, N-oxydiert,Have meanings, N-oxidized,
und erwünschtenfalls eine erhaltene Verbindung der allgemeinen Formel I in ein Säureadditionssalz überführt.and, if desired, a compound obtained from the general Formula I converted into an acid addition salt.
Durch die Verfahrensvariante a) können VerbindungenProcess variant a) allows connections
2 3 4 2' 3'2 3 4 2 '3'
der Formel I, worin R , R und R die für R , R und ORof the formula I, in which R, R and R represent R, R and OR
bzw. OCR oben angegebenen Bedeutungen besitzen, hergestellt werden.or OCR have the meanings given above, are produced.
Unter Verwendung einer Verbindung der Formel III als Reagens kann die Verfahrensvariante durchgeführt werden, indem man das Oxim der Formel II mit der Verbindung der Formel III zweckmässigerweise in Gegenwart einer Base, in einem organischen Lösungsmittel und in einem Temperaturbereich zwischen 00C und der Rückflusstemperatur des Reaktionsgemisches umsetzt. Das Lösungsmittel kann protisch oder nicht protisch sein. Im Falle von protischen Lösungsmitteln, wie Alkoholen, insbesondere Methanol oder Aethanol,Using a compound of the formula III as a reagent, the process variant can be carried out by converting the oxime of the formula II with the compound of the formula III, conveniently in the presence of a base, in an organic solvent and in a temperature range between 0 ° C. and the reflux temperature of the Reaction mixture converts. The solvent can be protic or non-protic. In the case of protic solvents such as alcohols, in particular methanol or ethanol,
:'3:31:0H8: '3: 31: 0H8
- yr 21 - yr 21
ist die verwendete Base vorzugsweise ein Alkalimetallhydroxid, z.B. Natrium- oder Kaliumhydroxid, oder ein Alkalimetallalkoholat. Bei Verwendung von nichtprotischen Lösungsmitteln, wie aliphatischen oder cyclischen Aethern, insbesondere Tetrahydrofuran oder Dimethoxyäthan, und Dialkylarniden, insbesondere Dimethylformamid, ist die Base vorzugsweise ein Alkalimetallhydrid, z.B. Natriumhydrid. In einer bevorzugten Ausführungsform dieses Verfahrens werden Natriumhydrid als Base und ein aliphatischer oder cyclischer Aether, insbesondere Tetrahydrofuran oder Dimethoxyäthan, oder ein Dialkylamid, insbesondere Dimethylformamid, als Lösungsmittel verwendet.the base used is preferably an alkali metal hydroxide, e.g. sodium or potassium hydroxide, or a Alkali metal alcoholate. When using non-protic solvents such as aliphatic or cyclic ethers, in particular tetrahydrofuran or dimethoxyethane, and dialkyl amides, in particular dimethylformamide, is the base preferably an alkali metal hydride such as sodium hydride. In a preferred embodiment of this method Sodium hydride as the base and an aliphatic or cyclic one Ether, especially tetrahydrofuran or dimethoxyethane, or a dialkylamide, especially dimethylformamide, used as a solvent.
Unter Verwendung eines reaktionsfähigen Derivats einer Säure der Formel IV als Reagens erfolgt die Umsetzung zweckmässigerweise in Gegenwart einer Base, wie Natriumhydrid oder Lithiumdiisopropylamid, in einem organischen Lösungsmittel, wie einem aliphatischen oder cyclischen Aether, z.B. Dimethoxyäthan oder Tetrahydrofuran, oder einem Dialkylamid, z.B. Dimethylformamid, und in einem Temperaturbereich zwischen 00C und der Rückflusstemperatur des Reaktionsgemisches, vorzugsweise zwischen 00C und der Raumtemperatur. Als Base und gleichzeitig als Lösungsmittel eignet sich insbesondere Pyridin.Using a reactive derivative of an acid of the formula IV as a reagent, the reaction is conveniently carried out in the presence of a base, such as sodium hydride or lithium diisopropylamide, in an organic solvent, such as an aliphatic or cyclic ether, e.g. dimethoxyethane or tetrahydrofuran, or a dialkylamide, e.g. dimethylformamide, and in a temperature range between 0 ° C. and the reflux temperature of the reaction mixture, preferably between 0 ° C. and room temperature. Pyridine is particularly suitable as a base and at the same time as a solvent.
Gemäss der Verfahrensvariante b), die zu VerbindungenAccording to process variant b), the compounds
2 3 4 2' 3'2 3 4 2 '3'
der Formel I führt, worin R , R und R die für R , Rof formula I, wherein R, R and R the for R, R
5"
resp. OR oben angegebenen Bedeutungen besitzen, erfolgt die Umsetzung zweckmässigerweise in einem organischen
Lösungsmittel, z.B. einem Alkohol, wie Methanol oder Aethanol,
einem Dialkylamid, wie Dimethylformamid, oder einem tertiären Amin, wie Pyridin. Man arbeitet vorzugsweise in
einem Temperaturbereich zwischen der Raumtemperatur und der Rückflusstemperatur des Reaktionsgemisches. Da das Ausgangsmaterial
der Formel VI vorzugsweise in Form eines Säureadditionssalzes, z.B. des Hydrochlorids oder Hydrosulfats,
eingesetzt wird, wird dem Reaktionsgemisch zweckmässigerweise eine Base, wie Natrium- oder Kaliumcarbonat,5 "
resp. OR have the meanings given above, the reaction is conveniently carried out in an organic solvent, for example an alcohol such as methanol or ethanol, a dialkylamide such as dimethylformamide, or a tertiary amine such as pyridine. It is preferred to work in a temperature range between room temperature and the reflux temperature of the reaction mixture. Since the starting material of the formula VI is preferably used in the form of an acid addition salt, for example the hydrochloride or hydrosulfate, a base such as sodium or potassium carbonate is expediently added to the reaction mixture.
Triäthylamin oder Pyridin, zugesetzt. Dieses Verfahren kommt vor allem für solche Fälle in Frage, in denen R unsubstituiertes C, ,-Alkyl, C__g-Alkenyl oder gegebenenfalls substituiertes Aryl-C,_3alkyl oder Aryl, wie oben näher definiert, bedeutet.Triethylamine or pyridine was added. This method is mainly used for such cases in question, in which, alkyl C__g alkenyl or optionally substituted aryl-C, _ 3 alkyl or aryl as defined in more detail above, R is unsubstituted C.
Die Verfahrensvariante c) führt zu denjenigen Verbin-Process variant c) leads to those connec-
2 2'2 2 '
düngen der Formel I, worin R die für R oben angegebene Bedeutung besitzt und R Chlor oder Brom bedeutet. Als geeignete Halogenierungsmittel kommen insbesondere elementares Chlor oder Brom in Frage, wobei zweckmässigerweise die Halogenierung in Gegenwart eines halogenierten Kohlenwasserstoffes, wie Chloroform oder Tetrachlorkohlenstoff, als Lösungsmittel erfolgt. Weitere Halogenierungsmittel sind z.B. Sulfurylchlorid, das in einem Ueberschuss verwendet wird und gleichzeitig als Lösungsmittel dienen kann, und N-Bromsuccinimid, das zweckmässigerweise unter Zugabe eines Radikalbildners, wie Benzoylperoxid, eingesetzt wird. Im allgemeinen bewegen sich die geeigneten Reaktionstemperaturen zwischen Raumtemperatur und der Rückflusstemperatur des Reaktionsgemisches.fertilize the formula I, wherein R is the one given for R above Has meaning and R is chlorine or bromine. Particularly suitable halogenating agents are elemental Chlorine or bromine in question, the halogenation expediently in the presence of a halogenated hydrocarbon, such as chloroform or carbon tetrachloride, as Solvent takes place. Further halogenating agents are e.g. sulfuryl chloride, which is used in excess is and can serve as a solvent at the same time, and N-bromosuccinimide, which is conveniently with the addition of a Free radical generator, such as benzoyl peroxide, is used. In general, the suitable reaction temperatures range between room temperature and the reflux temperature of the reaction mixture.
Gemäss der Verfahrensvariante d), die zu denjenigenAccording to process variant d), those for those
2 2'2 2 '
Verbindungen der Formel I führt, worin R die für R oben angegebene Bedeutung besitzt und R Hydroxy bedeutet, erfolgt die Reduktion vorzugsweise mittels Natriumborhydrid als Reduktionsmittel, wobei zweckmässigerweise in einem protischen Verdünnungsmittel, wie einem aliphatischen Alkohol, z.B. Methanol oder Aethanol, und bei Temperaturen um Raumtemperatur gearbeitet wird.Compounds of the formula I in which R is those given above for R Has meaning and R is hydroxy, the reduction is preferably carried out using sodium borohydride as Reducing agent, advantageously in a protic diluent such as an aliphatic alcohol, e.g. methanol or ethanol, and working at temperatures around room temperature.
Bei der Verfahrensvariante e) handelt es sich um dieProcess variant e) is the
2 N-Oxydation derjenigen Endprodukte der Formel I, worin R2 N-oxidation of those end products of the formula I in which R
2' die oben angegebenen Bedeutungen von R besitzt. Die Umsetzung kann zweckmässigerweise durchgeführt werden, indem man die Verbindung der Formel I" mittels Wasserstoffperoxid oder einer Persäure in Gegenwart eines inerten Verdünnungsmittels N-oxydiert.2 'has the meanings of R given above. the The reaction can conveniently be carried out by converting the compound of the formula I "using hydrogen peroxide or a peracid is N-oxidized in the presence of an inert diluent.
Im Falle der Verwendung von Wasserstoffperoxid als Oxydationsmittel kommen als Verdünnungsmittel insbesondere niedere Alkanole, wie Methanol, Aethanol und Isopropanol, in Frage, und die N-Oxydation wird vorzugsweise in einem Temperaturbereich zwischen 0° und 600C, insbesondere zwischen 20° und 400C, vorgenommen.In the case of using hydrogen peroxide as an oxidising agent suitable diluents particularly lower alkanols such as methanol, ethanol and isopropanol, in question, and the N-oxidation is preferably carried out in a temperature range between 0 ° and 60 0 C, in particular between 20 ° and 40 0 C, made.
Als Persäuren kommen vorzugsweise Peressigsäure, Perbenzoesäure und m-Chlorperbenzoesäure in Frage, wobei bevorzugt in einem halogenierten Kohlenwasserstoff, z.B. Methylenchlorid oder Chloroform, als Verdünnungsmittel gearbeitet wird. Die N-Oxydation mit einer Persäure erfolgt vorzugsweise in einem Temperaturbereich zwischen 0eC und der Rückflusstemperatur des Reaktionsgemisches, insbe-Peracetic acid, perbenzoic acid and m-chloroperbenzoic acid are preferably used as peracids, the diluent preferably being a halogenated hydrocarbon, for example methylene chloride or chloroform. The N-oxidation with a peracid is preferably carried out in a temperature range between 0 e C and the reflux temperature of the reaction mixture, and in particular
■)5 sondere zwischen 00C und der Raumtemperatur. Eine besonders bevorzugte Ausführungsform dieses Verfahrens besteht darin, dass man die N-Oxydation mit m-Chlorperbenzoesäure in Chloroform in einem Temperaturbereich zwischen 00C und der Raumtemperatur durchführt.■) 5 special between 0 0 C and room temperature. A particularly preferred embodiment of this process consists in carrying out the N-oxidation with m-chloroperbenzoic acid in chloroform in a temperature range between 0 ° C. and room temperature.
Zur Herstellung von Säureadditionssalzen können erwünschtenfalls die Verbindungen der Formel I mit anorganischen oder organischen Säuren, wie z.B. Salzsäure, Salpetersäure, Phosphorsäure, mono- und bifunktionellen Carbonsäuren und Hydroxycarbonsäuren oder Sulfonsäuren, in an sich bekannter Weise umgesetzt werden.For the preparation of acid addition salts, if desired the compounds of formula I with inorganic or organic acids, such as hydrochloric acid, nitric acid, Phosphoric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids or sulfonic acids, in an can be implemented in a known manner.
Die Isolierung und Reinigung der so hergestellten Verbindungen der Formel I und deren Säureadditionssalze erfolgen nach an sich bekannten Methoden.The isolation and purification of the compounds so produced of the formula I and their acid addition salts are carried out according to methods known per se.
Die als Ausgangsmaterialien verwendbaren Oxime der Formel II können z.B. aus den entsprechenden Ketonen der Formel V, wie oben definiert, durch Umsetzung mit Hydroxylamin in an sich bekannter Weise hergestellt werden.The oximes of the formula II which can be used as starting materials can be obtained, for example, from the corresponding ketones of Formula V, as defined above, by reaction with hydroxylamine can be produced in a manner known per se.
2'2 '
Die Ketone der Formel V, worin R unsubstituiertesThe ketones of the formula V, wherein R is unsubstituted
oder mit Methyl, Methoxy oder Chlor substituiertes 3-Pyridylor 3-pyridyl substituted with methyl, methoxy or chlorine
Vi-Vi
3 ι3 ι
oder 5-Pyrimidinyl und R Wasserstoff oder C,_. -Alkyl bedeuten, können z.B. hergestellt werden, indem man eine Verbindung der allgemeinen Formelor 5-pyrimidinyl and R is hydrogen or C, _. -Alkyl mean can for example be prepared by adding a compound of the general formula
ι ?ι?
R C H VIIIR C H VIII
CNCN
worin R die oben angegebene Bedeutung besitzt und Z eine disubstituierte Aminogruppe, z.B.wherein R is as defined above and Z is a disubstituted amino group, e.g.
Dimethylamino, Diäthylamino, Piperidino oder Morpholino, bedeutet, mit einem Halogenid der allgemeinen FormelDimethylamino, diethylamino, piperidino or morpholino, means with a halide of the general formula
R3"
f .. ' R 3 "
f .. '
Hai CH R2" IXShark CH R 2 "IX
2"
worin R 3-Pyridyl oder 5-Pyrimidinyl, unsub-2 "
wherein R 3-pyridyl or 5-pyrimidinyl, unsub-
stituiert oder mit Methyl, Methoxy oder Chlor substituiert,substituted or with methyl, methoxy or Substituted chlorine,
3"
R Wasserstoff oder C. .-Alkyl3 "
R is hydrogen or C. .. -alkyl
und Hai Chlor, Brom oder Jod bedeuten, umsetzt, und das erhaltene Produkt, das entweder aus einer Verbindung der allgemeinen Formeland Hal mean chlorine, bromine or iodine, and the product obtained, either from a Compound of the general formula
,,,,,,
Z RZ R
ill 2"ill 2 "
CNCN
oder einer der allgemeinen Formelor one of the general formula
3"3 "
ill 2" R C-=* C R XI ill 2 " R C - = * CR XI
oder einem Gemisch der beiden Verbindungen der Formeln X und XI besteht, hydrolysiert. Die Umsetzung der Verbindung der Formel VIII mit dem Halogenid der Formel IX kann z.B. unter den Bedingungen der Phasentransferkatalyse (sieheor a mixture of the two compounds of the formulas X and XI is hydrolyzed. Implementation of the connection of the formula VIII with the halide of the formula IX can, for example, under the conditions of phase transfer catalysis (see
z.B. J. Dockx, Synthesis (1973), 441) oder unter Verwendung einer Base, wie Natriumhydrid oder Lithiumdiisopropylamid, in einem organischen Lösungsmittel, wie einem aliphatischen oder cyclischen Aether, z.B. Dimethoxyäthan oder Tetrahydrofuran, und in einem Temperaturbereich zwischen -70° und 500C, vorzugsweise zwischen -300C und der Raumtemperatur, durchgeführt werden. Unabhängig von der Produkteverteilung lässt sich hierauf das so erhaltene Rohprodukt durch Hydrolyse, z.B. durch konventionelle Behandlung mit einer wässrigen Säure, in das Keton der Formel V überführen. Als Säuren kommen für diesen Zweck insbesondere starke anorganische Säuren, wie Schwefelsäure, Chlorwasserstoff und Bromwasserstoff, sowie Sulfonsäuren, wie Benzolsulfonsäure und p-Toluolsulfonsäure, in Frage. In gewissen Fällen, z.B. im Falle der Bildung eines Zwischenproduktes der Formel X, können auch Carbonsäuren, wie Essigsäure, verwendet werden. Die Hydrolyse wird zweckmässigerweise in einem Temperaturbereich zwischen 200C und der Rückflusstemperatur des Reaktionsgemisches, vorzugsweise zwischen 80° und 100°C, 'ausgeführt.e.g. J. Dockx, Synthesis (1973), 441) or using a base such as sodium hydride or lithium diisopropylamide in an organic solvent such as an aliphatic or cyclic ether, e.g. dimethoxyethane or tetrahydrofuran, and in a temperature range between -70 ° and 50 0 C, preferably between -30 0 C and room temperature, are carried out. Irrespective of the product distribution, the crude product obtained in this way can then be converted into the ketone of the formula V by hydrolysis, for example by conventional treatment with an aqueous acid. Suitable acids for this purpose are, in particular, strong inorganic acids such as sulfuric acid, hydrogen chloride and hydrogen bromide, and also sulfonic acids such as benzenesulfonic acid and p-toluenesulfonic acid. In certain cases, for example in the case of the formation of an intermediate of the formula X, carboxylic acids such as acetic acid can also be used. The hydrolysis is conveniently carried out in a temperature range between 20 0 C and the reflux temperature of the reaction mixture, preferably between 80 ° and 100 ° C '.
2'2 '
Die Ketone der Formel V, worin R unsubstituiertesThe ketones of the formula V, wherein R is unsubstituted
oder mit Methyl, Methoxy oder Chlor substituiertes 2-Pyra-or 2-pyra substituted with methyl, methoxy or chlorine
3 '
zinyl und R Wasserstoff oder C, .-Alkyl bedeuten, können
z.B. gemäss dem in der DOS 2 800 010 beschriebenen Verfahren hergestellt werden.3 '
Zinyl and R are hydrogen or C1-alkyl can be prepared, for example, according to the process described in DOS 2,800,010.
Die übrigen Ketone der Formel V, d.h. diejenigen,The remaining ketones of formula V, i.e. those
3 ·
worin R C,- oder C.-Alkenyl oder C-,- oder C.-Alkinyl bedeutet,
sowie die Ketone der Formel V, worin R C- .-Alkyl bedeutet (alternative Methode), können dadurch hergestellt
werden, dass man ein Keton der allgemeinen Formel3 ·
in which RC, - or C.-Alkenyl or C -, - or C. -Alkynyl, and the ketones of the formula V, in which R denotes C-. -alkyl (alternative method), can be prepared by using a ketone the general formula
1 2'1 2 '
R —C CH., R VR-C CH., R V
Il 2 Il 2
00
1 2'
worin R und R die oben angegebenen Bedeutungen1 2 '
wherein R and R have the meanings given above
besitzen,own,
mit einer Verbindung der allgemeinen Formelwith a compound of the general formula
R U XIIR U XII
3111
worin R C-_ -Alkyl, C3- oder C.-Alkenyl 3111
wherein R is C 1-6 alkyl, C 3 or C alkenyl
oder C,- oder C.-Alkinyl und U eine Abgangsgruppe, insbesondereor C, - or C-alkynyl and U is a leaving group, in particular
Chlor, Brom oder Jod, bedeuten,Chlorine, bromine or iodine, mean
umsetzt. Das Keton wird vorteilhaft zunächst mit einer Base, wie Natriumhydrid oder Lithiumdiisopropylamid, in einem Verdünnungsmittel, vorzugsweise einem aprotischen organischen Lösungsmittel, wie einem aliphatischen oder cyclischen Aether, z.B. Dimethoxyäthan oder Tetrahydrofuran, oder einem Dialkylamid, z.B. Dimethylformamid, bei Reaktionstemperaturen zwischen -700C und 500C in das Anion übergeführt, welches anschliessend mit der Verbindung der Formel XII in demselben Reaktionsmedium umgesetzt werden kann.implements. The ketone is advantageously first with a base such as sodium hydride or lithium diisopropylamide, in a diluent, preferably an aprotic organic solvent such as an aliphatic or cyclic ether, for example dimethoxyethane or tetrahydrofuran, or a dialkylamide such as dimethylformamide, at reaction temperatures between -70 0 C and 50 0 C converted into the anion, which can then be reacted with the compound of the formula XII in the same reaction medium.
Die als Ausgangsmaterialien verwendbaren Ketone der Formel VII können aus den entsprechenden Ketooximen der allgemeinen FormelThe ketones of the formula VII which can be used as starting materials can be obtained from the corresponding ketooximes of the general formula
1 2'1 2 '
R C C R XIIIR C C R XIII
W WW W
NONO
OHOH
1 2'
worin R und R die oben angegebenen Bedeutungen1 2 '
wherein R and R have the meanings given above
besitzen,own,
durch Umsetzung mit den Verbindungen der Formel III, wie oben definiert, hergestellt werden, und zwar unter den gleichen Reaktionsbedingungen wie sie oben im Zusammenhang mit der Verfahrensvariante a) beschrieben sind. Die Ketooxime der Formel XIII sind aus entsprechenden Ketonen der allgemeinen Formelby reaction with the compounds of formula III, as defined above, are prepared, namely under the the same reaction conditions as described above in connection with process variant a). The ketooxime of the formula XIII are selected from corresponding ketones of the general formula
R CH0 C R2' XIVR CH 0 CR 2 'XIV
1 2'
worin R und R die oben angegebenen Bedeutungen1 2 '
wherein R and R have the meanings given above
besitzen,own,
durch Behandlung mit salpetriger Säure oder einem Alkylnitrit in an sich bekannter Weise zugänglich.by treatment with nitrous acid or an alkyl nitrite accessible in a manner known per se.
Die als Reagenzien bzw. Ausgangsmaterialien verwendbaren Verbindungen der Formeln III, VI, VIII, IX, XII und XIV und reaktionsfähigen Derivate der Säuren der Formel IV sind entweder bekannt oder können nach an sich bekannten Methoden hergestellt werden.The compounds of the formulas III, VI, VIII, IX, XII and which can be used as reagents or starting materials XIV and reactive derivatives of the acids of the formula IV are either known or can be according to known Methods are made.
Bei den als Ausgangsmaterialien verwendbaren Verbindungen der Formeln I1, I" und V handelt es sich zugleich um Unterklassen von Verbindungen der Formel I bzw. V.The compounds of the formulas I 1 , I "and V which can be used as starting materials are at the same time subclasses of compounds of the formulas I and V, respectively.
Die erfindungsgemässen Verbindungen, d.h. die Verbindungen der Formel I und deren Säureadditionssalze, besitzen fungizide Wirkung und können dementsprechend zur Bekämpfung von Fungi in der Landwirtschaft und im Gartenbau Verwendung finden. Sie eignen sich insbesondere zur Eindämmung des Wachstums oder zur Vernichtung von phytopathogenen Pilzen auf Pflanzenteilen, z.B. Blättern, Stengeln, Wurzeln, Knollen, Früchten oder Blüten, und auf Saatgut sowie im Erdboden und sind besonders wirksam bei der Bekämpfung von Botrytis cinerea (Graufäule); von echten Mehltaupilzen, wie beispielsweise Uncinula necator (Rebenmehltau), Erysiphe cichoracearum (Gurkenmehltau), Podosphaera leucotricha (Apfelmehltau) und Erysiphe graminis (Gerstenmehltau); von Venturia inaequalis (Apfelschorf); von Helminthosporium oryzae (Braunfleckenkrankheit von Reis); und von Schadpilzen der Gattungen Puccinia, Uromyces, Rhizoctonia, Penicillium, Septoria und Cercospora.The compounds of the invention, i.e. the compounds of the formula I and their acid addition salts have fungicidal activity and can accordingly be used for Fungi control in agriculture and horticulture are used. They are particularly suitable for Curbing the growth or destroying phytopathogenic fungi on parts of plants, e.g. leaves, Stems, roots, tubers, fruits or flowers, and on Seeds as well as in the soil and are particularly effective in combating Botrytis cinerea (gray rot); of real Powdery mildew, such as Uncinula necator (powdery mildew of the vine), Erysiphe cichoracearum (cucumber powdery mildew), Podosphaera leucotricha (apple powdery mildew) and Erysiphe graminis (Barley powdery mildew); from Venturia inaequalis (apple scab); of Helminthosporium oryzae (brown spot disease of Rice); and of harmful fungi of the genera Puccinia, Uromyces, Rhizoctonia, Penicillium, Septoria and Cercospora.
Einzelne Vertreter der erfindungsgemässen Verbindüngen besitzen zudem eine ausgeprägte Wirkung gegen holzzerstörende Pilze, wie z.B. Coniophora puteana und Gloeophyllum trabeurn.Individual representatives of the compounds according to the invention also have a pronounced effect against wood-destroying fungi, such as Coniophora puteana and Gloeophyllum trabeurn.
- yr - - yr -
Die erfindungsgemässen Verbindungen zeichnen sich durch lokale und bzw. oder systemische Wirkung aus.The compounds according to the invention stand out through local and / or systemic effects.
Die erfindungsgemässen Verbindungen wirken unter Gewächshausbedingungen bereits bei einer Konzentration von mg bis 500 mg Wirksubstanz pro Liter Spritzbrühe, im Freiland werden vorteilhaft Konzentrationen von 50 g bis 2000 g Wirkstoff der Formel I pro Hektar und Behandlung zur Anwendung gebracht.The compounds according to the invention act under greenhouse conditions even at a concentration of mg to 500 mg of active substance per liter of spray mixture, outdoors concentrations of 50 g to 2000 g of active ingredient of the formula I per hectare and treatment are advantageously used brought.
Unter Verwendung von Formulierungshilfsstoffen können die erfindungsgemässen Verbindungen, also die fungiziden Wirkstoffe, in die üblichen Formulierungen übergeführt werden, wie Stäube, Pulver, Granulate, Lösungen, Emulsionen, Suspensionen, emulgierbare Konzentrate, Pasten und dergleichen. Das erfindungsgemässe fungizide Mittel ist dadurch gekennzeichnet, dass es eine wirksame Menge mindestens einer Verbindung der allgemeinen Formel I, wie oben definiert, oder eines Säureadditionssalzes einer, solchen Verbindung sowie Formulierungshilfsstoffe enthält. Die Mittel enthalten zweckmässigerweise zumindest einen der folgenden Formulierungshilfsstoffe:Using formulation auxiliaries you can the compounds according to the invention, that is to say the fungicidal active ingredients, are converted into the customary formulations such as dusts, powders, granulates, solutions, emulsions, suspensions, emulsifiable concentrates, pastes and like that. The fungicidal agent according to the invention is characterized in that there is an effective amount of at least one compound of the general formula I, as above or an acid addition salt of such a compound and formulation auxiliaries. the Agents expediently contain at least one of the following formulation auxiliaries:
Feste Trägerstoffe; Lösungs- bzw. Dispersionsmittel; Tenside (Netz- und Emulgiermittel); Dispergatoren (ohne Tensidwirkung); und Stabilisatoren.Solid carriers; Solvents or dispersants; Surfactants (wetting and emulsifying agents); Dispersants (without surfactant effect); and stabilizers.
Als feste Trägerstoffe kommen im wesentlichen in Frage: natürliche Mineralstoffe, wie Kaolin, Tonerden, Kieselgur, Talkum, Bentonit, Kreide, z.B. Schlämmkreide, Magnesiumcarbonat, Kalkstein, Quarz, Dolomit, Attapulgit, Montmorillonit und Diatomeenerde; synthetische Mineralstoffe, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate; organische Stoffe, wie Cellulose, Stärke, Harnstoff und Kunstharze; und Düngemittel, wie Phosphate und Nitrate, wobei solche Trägerstoffe z.B. als Granulate oder Pulver vorliegen können.The following solid carriers are essentially: natural minerals such as kaolin, clay, Kieselguhr, talc, bentonite, chalk, e.g. whipped chalk, magnesium carbonate, limestone, quartz, dolomite, attapulgite, Montmorillonite and diatomaceous earth; synthetic minerals such as highly dispersed silica, aluminum oxide and Silicates; organic substances such as cellulose, starch, urea and synthetic resins; and fertilizers, such as phosphates and Nitrates, whereby such carriers can be in the form of granulates or powders, for example.
Als Lösungs- bzw. Dispersionsmittel kommen im wesentlichen in Frage: Aromaten, wie Benzol, Toluol, Xylole und Alkylnaphthaline; chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chloräthylene und Methylenchlorid; aliphatische Kohlenwasserstoffe, wie Cyclohexan und Paraffine, z.B. Erdölfraktionen; Alkohole, wie Butanol und Glykol, sowie deren Aether und Ester; Ketone, wie Aceton, Methylethylketon, Methylisobutylketon und Cyclohexanon; und stark polare Lösungs- bzw. Dispersionsmittel, wie Dimethylformamid, N-Methylpyrrolidon und Dimethylsulfoxid, wobei solche Lösungs- bzw. Dispersionsmittel vorzugsweise Flammpunkte von mindestens 300C und Siedepunkte von mindestens.500C aufweisen, und Wasser. Unter den Lösungs- bzw. Dispersionsmitteln kommen auch in Frage sogenannte verflüssigte gasförmige Streckmittel oder Trägerstoffe, die solche Produkte sind, welche bei Raumtemperatur und unter Normaldruck gasförmig sind. Beispiele solcher Produkte sind insbesondere Aerosol-Treibgase, wie Halogenkohlenwasserstoffe, z.B. Dichlordifluormethan. Im Falle der Benutzung von Wasser als Lösungsmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden.Possible solvents or dispersants are essentially: aromatics, such as benzene, toluene, xylenes and alkylnaphthalenes; chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes and methylene chloride; aliphatic hydrocarbons, such as cyclohexane and paraffins, for example petroleum fractions; Alcohols, such as butanol and glycol, and their ethers and esters; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; and strongly polar solvents or dispersants, such as dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, such solvents or dispersants preferably having flash points of at least 30 ° C. and boiling points of at least 50 ° C., and water. Among the solvents or dispersants, so-called liquefied gaseous extenders or carriers, which are products which are gaseous at room temperature and under normal pressure, are also suitable. Examples of such products are in particular aerosol propellants, such as halogenated hydrocarbons, for example dichlorodifluoromethane. If water is used as the solvent, organic solvents can, for example, also be used as auxiliary solvents.
Die Tenside (Netz- und Emulgiermittel) können nichtionische Verbindungen sein, wie Kondensationsprodukte von Fettsäuren, Fettalkoholen oder fettsubstituierten Phenolen mit Aethylenoxid; Fettsäureester und -äther von Zuckern oder mehrwertigen Alkoholen; die Produkte, die aus Zuckern oder mehrwertigen Alkoholen durch Kondensation mit Aethylenoxid erhalten werden; Blockpolymere von Aethylenoxid und Propylenoxid; oder Alkyldimethylaminoxide.The surfactants (wetting and emulsifying agents) can be nonionic compounds, such as condensation products of Fatty acids, fatty alcohols or fat-substituted phenols with ethylene oxide; Fatty acid esters and ethers of sugars or polyhydric alcohols; the products made from sugars or polyhydric alcohols by condensation with ethylene oxide obtained; Block polymers of ethylene oxide and propylene oxide; or alkyl dimethyl amine oxides.
Die Tenside können auch anionische Verbindungen darstellen, wie Seifen; Fettsulfatester, z.B. Dodecylnatriumsulfat, Octadecylnatriumsulfat und Cetylnatriumsulfat; Alkylsulfonate, Arylsulfonate und fettaromatische Sulfonate, wie Alkylbenzolsulfonate, z.B. Calcium-dodecylbenzolsulfonat, und Butylnaphthalinsulfonate; und komplexereThe surfactants can also be anionic compounds, such as soaps; Fatty sulfate esters, e.g. dodecyl sodium sulfate, Octadecyl sodium sulfate and cetyl sodium sulfate; Alkyl sulfonates, aryl sulfonates and fatty aromatic sulfonates, such as alkylbenzenesulfonates, e.g. calcium dodecylbenzenesulfonate, and butylnaphthalene sulfonates; and more complex
Fettsulfonate, z.B. die Amidkondensationsprodukte von OeI-säure und N-Methyltaurin und das Natriumsulfonat von Dioctylsuccinat. Fatty sulfonates, e.g. the amide condensation products of oleic acid and N-methyl taurine and the sodium sulfonate of dioctyl succinate.
Die Tenside können schliesslich kationische Verbindungen sein, wie Alkyldimethylbenzylammoniumchloride, Dialkyldimethylammoniumchloride, Alkyltrimethylammoniumchloride und äthoxylierte quaternäre Ammoniumchloride.Finally, the surfactants can be cationic compounds, such as alkyldimethylbenzylammonium chlorides, Dialkyldimethylammonium chlorides, alkyltrimethylammonium chlorides and ethoxylated quaternary ammonium chlorides.
Als Dispergatoren (ohne Tensidwirkung) kommen im wesentlichen in Frage: Lignin, Natrium- und Ammoniumsalze von Ligninsulfonsäure, Natriumsalze von Maleinsäureanhydrid-Diisobutylen-Copolymeren, Natrium- und Ammoniumsalze von sulfonierten Polykondensationsprodukten ausThe dispersants (without surfactant effect) are im essential question: lignin, sodium and ammonium salts of ligninsulphonic acid, sodium salts of maleic anhydride-diisobutylene copolymers, Sodium and ammonium salts from sulfonated polycondensation products
•J5 Naphthalin und Formaldehyd, und Sulfitablaugen.• J5 Naphthalene and formaldehyde, and sulphite waste liquors.
Als Dispergatoren, die sich insbesondere als Verdickungs- bzw. Antiabsetzmittel eignen, können z.B. Methylcellulose, Carboxymethylcellulose, Hydroxyäthylcellulose, Polyvinylalkohol, Alginate, Caseinate und Blutalbumin eingesetzt werden.As dispersants, which are particularly suitable as thickeners or anti-settling agents, e.g. methyl cellulose, Carboxymethyl cellulose, hydroxyethyl cellulose, polyvinyl alcohol, alginates, caseinates and blood albumin can be used.
Beispiele von geeigneten Stabilisatoren sind säurebindende Mittel, z.B. Epichlorhydrin, Phenylglycidäther und Soyaepoxide; Antioxidantien z.B. Gallussäureester und Butylhydroxytoluol; UV-Absorber z.B. substituierte Benzophenone, Diphenylacrylnitrilsäureester und Zimtsäureester; und Deaktivatoren z.B. Salze der Aethylendiaminotetra-. essigsäure und Polyglykole.Examples of suitable stabilizers are acid-binding agents, e.g., epichlorohydrin, phenyl glycidyl ether and Soy epoxide; Antioxidants such as gallic acid esters and butylated hydroxytoluene; UV absorbers e.g. substituted benzophenones, Diphenylacrylonitrile acid esters and cinnamic acid esters; and deactivators, e.g. salts of ethylenediaminotetra-. acetic acid and polyglycols.
Die erfindungsgemässen fungiziden Mittel können neben den Wirkstoffen der Formel I auch andere Wirkstoffe enthalten, z.B. anderweitige fungizide Mittel, insektizide und akarizide Mittel, Bakterizide, Pflanzenwachstumsregulatoren und Düngemittel. Solche Kombinationsmittel eignen sich zur Verbreiterung des Wirkungsspektrums oder zur spezifischen Beeinflussung des Pflanzenwachstums.The fungicidal agents according to the invention can in addition to the active ingredients of the formula I also contain other active ingredients, e.g. other fungicidal agents, insecticides and acaricidal agents, bactericides, plant growth regulators and fertilizers. Such combination agents are suitable for Broadening the spectrum of activity or for specifically influencing plant growth.
.3-3-V0148.3-3-V0148
Im allgemeinen enthalten die erfindungsgemässen fungiziden Mittel, je nach Typ, zwischen 0,0001 und 95 Gewichtsprozent an erfindungsgemässer Verbindung bzw. erfindungsgemässen Verbindungen als Wirkstoff(en). Sie können in einer Form vorliegen, die sich für die Lagerung und den Transport eignet. In solchen Formen, z.B. emulgierbaren Konzentraten, ist die Wirkstoffkonzentration normalerweise im höheren Bereich der obigen Konzentrationsreihe. Diese Formen können dann mit gleichen oder verschiedenen Formulierungshilfsstoffen bis zu Wirkstoffkonzentrationen verdünnt werden, die sich für den praktischen Gebrauch eignen, und solche Konzentrationen liegen normalerweise im niedrigeren Bereich der obigen Konzentrationsreihe. Emulgierbare Konzentrate enthalten im allgemeinen 5 bis 95 Gewichtsprozent, vorzugsweise 25 bis 75 Gewichtsprozent, der Verbindung bzw. Verbindungen der Formel I. Als Anwendungsformen kommen u.a. gebrauchsfertige Lösungen, Emulsionen und Suspensionen, die sich beispielsweise als Spritzbrühen eignen, in Frage. In solchen Spritzbrühen können z.B. Konzentrationen zwischen 0,0001 und 20 Gewichtsprozent vorliegen. Im Ultra-Low-Volume-Verfahren können Spritzbrühen formuliert werden, in denen die Wirkstoffkonzentration vorzugsweise von 0,5 bis 20 Gewichtsprozent beträgt, während die im Low-Volume-Verfahren und im High-Volume-Verfahren formulierten Spritzbrühen vorzugsweise eine Wirkstoffkonzentration von 0,02 bis 1,0 bzw. 0,002 bis 0,1 Gewichtsprozent aufweisen.In general, the fungicides according to the invention contain Agent, depending on the type, between 0.0001 and 95 percent by weight of compound according to the invention or according to the invention Compounds as active ingredient (s). They can be in a form that is convenient for storage and transportation suitable. In such forms, e.g. emulsifiable concentrates, the active ingredient concentration is usually in the higher Area of the above concentration series. These forms can then be mixed with the same or different formulation auxiliaries be diluted to concentrations of active ingredient suitable for practical use and such Concentrations are usually in the lower range of the above concentration series. Emulsifiable concentrates generally contain 5 to 95 percent by weight, preferably 25 to 75 percent by weight, of the compound or compounds of formula I. The application forms include ready-to-use solutions, emulsions and suspensions, which are suitable, for example, as spray liquors. In such spray liquors, for example, concentrations between 0.0001 and 20 percent by weight are present. In the ultra-low-volume process Spray mixtures can be formulated in which the active ingredient concentration is preferably from 0.5 to 20 percent by weight, while the spray mixtures formulated in the low-volume process and in the high-volume process preferably have an active ingredient concentration of 0.02 to 1.0 or 0.002 to 0.1 percent by weight.
Die erfindungsgemässen fungiziden Mittel können dadurch hergestellt werden, dass man mindestens eine Verbindung der allgemeinen Formel I bzw. ein Säureadditionssalz einer solchen Verbindung mit Formulierungshilfsstoffen vermischt.The fungicidal agents according to the invention can thereby be prepared that at least one compound of the general formula I or an acid addition salt such a compound mixed with formulation auxiliaries.
Die Herstellung der Mittel kann in bekannter Weise durchgeführt werden, z.B. durch Vermischen des Wirkstoffes mit festen Trägerstoffen, durch Auflösen oder Suspendieren in geeigneten Lösungs- bzw. Dispersionsmitteln, eventuell unter Verwendung von Tensiden als Netz- oder Emulgier-The preparation of the agents can be carried out in a known manner, for example by mixing the active ingredient with solid carriers, by dissolving or suspending in suitable solvents or dispersants, possibly using surfactants as wetting or emulsifying agents
mitteln oder von Dispergatoren, durch Verdünnen bereits vorbereiteter emulgierbarer Konzentrate mit Lösungs- bzw. Dispersionsmitteln usw.agents or dispersants, by diluting already prepared emulsifiable concentrates with solvents or Dispersants, etc.
Im Falle von pulverförmigen Mitteln kann der Wirkstoff mit einem festen Trägerstoff vermischt werden, z.B. durch Zusammenmahlen; oder man kann den festen Trägerstoff mit einer Lösung oder Suspension des Wirkstoffes imprägnieren und dann das Lösungs- oder Dispersionsmittel durch Abdunsten, Erhitzen oder durch Absaugen unter vermindertem Druck entfernen. Durch Zusatz von Tensiden bzw. Dispergatoren kann man solche pulverförmige Mittel mit Wasser leicht benetzbar machen, so dass sie in wässrige Suspensionen, die sich z.B. als Spritzmittel eignen, übergeführt werden können.In the case of powder compositions, the active ingredient can be mixed with a solid carrier, e.g. by grinding together; or you can impregnate the solid carrier with a solution or suspension of the active ingredient and then the solvent or dispersant by evaporation, heating or by suction under reduced pressure Remove pressure. Such pulverulent agents can be mixed with water by adding surfactants or dispersants Make them easily wettable, so that they are transferred into aqueous suspensions that are suitable, for example, as sprays can be.
Die erfindungsgemässen Verbindungen können auch mit einem Tensid und einem festen Trägerstoff zur Bildung eines netzbaren Pulvers vermischt werden, welches in Wasser dispergierbar ist, oder sie können mit einem festen vorgranulierten Trägerstoff zur Bildung eines granulatförmigen Produktes vermischt werden.The compounds according to the invention can also with a surfactant and a solid carrier are mixed to form a wettable powder, which in water Is dispersible, or they can be pregranulated with a solid carrier to form a granular Product are mixed.
Wenn gewünscht, kann eine erfindungsgemässe Verbindung in einem mit Wasser nicht mischbaren Lösungsmittel, wie beispielsweise einem alicyclischen Keton, gelöst werden, das zweckmassigerweise gelöste Emulgiermittel enthält, so dass die Lösung bei Zugabe zu Wasser selbstemulgierend wirkt. Andernfalls kann der Wirkstoff mit einem Emulgiermittel vermischt und das Gemisch dann mit Wasser auf die gewünschte Konzentration verdünnt werden. Zudem kann der Wirkstoff in einem Lösungsmittel gelöst und danach mit einem Emulgiermittel gemischt werden. Ein solches Gemisch kann ebenfalls mit Wasser auf die gewünschte Konzentration verdünnt werden. Auf diese Weise erhält man emulgierbare Konzentrate bzw. gebrauchsfertige Emulsionen.If desired, a compound according to the invention can be dissolved in a water-immiscible solvent, such as an alicyclic ketone, which conveniently contains dissolved emulsifying agent, so that the solution is self-emulsifying when added to water works. Otherwise, the active ingredient can be mixed with an emulsifying agent and then the mixture with water on the desired concentration can be diluted. In addition, the active ingredient can be dissolved in a solvent and then with mixed with an emulsifier. Such a mixture can also be mixed with water to the desired concentration be diluted. In this way, emulsifiable concentrates or ready-to-use emulsions are obtained.
- 22 -- 22 -
Die Verwendung der erfindungsgemässen Mittel kann nach den im Pflanzenschutz bzw. in der Landwirtschaft üblichen Applikationsmethoden erfolgen, wie Spritzen, Sprühen, Stäuben, Giessen oder Streuen. Das erfindungsgemässe Verfahren zur Bekämpfung von Fungi ist dadurch gekennzeichnet, dass man das zu schützende Gut, z.B. Pflanzen, Pflanzenteile bzw. Samen, mit einer wirksamen Menge einer erfindungsgemässen Verbindung bzw. eines erfindungsgemässen Mittels behandelt.The use of the agents according to the invention can after those commonly used in crop protection and agriculture Application methods take place, such as spraying, atomizing, dusting, pouring or scattering. The method according to the invention to combat fungi is characterized in that the property to be protected, e.g. plants, plant parts or seeds, with an effective amount of a compound according to the invention or a compound according to the invention Treated means.
Die nachstehenden Beispiele illustrieren die Erfindung. The following examples illustrate the invention.
I. Herstellung der Wirkstoffe: I. Production of the active ingredients:
6 g 2',4■-Dichlor-2-(2-pyrazinyl)-acetophenonoxim werden in 80 ml Dimethylformamid gelöst und mit 1,25 g .Natriumhydrid (ca. 50%-ige Dispersion in Mineralöl) versetzt. Nach 1 Stunde Rühren bei Raumtemperatur gibt man 5,2 g 2,4-Dichlorbenzylchlorid zu und lässt während 16 Stunden bei Raumtemperatur reagieren. Dann wird das Reaktionsgemisch auf Eiswasser gegossen und mit Aethylacetat extrahiert, und die organische Phase wird über wasserfreiem Natriumsulfat getrocknet und eingeengt. Das Rohprodukt wird einer Säulenchromatographie an Kieselgel mit Aethylacetat/ n-Hexan (1:1) unterworfen. Man erhält das 2',4'-Dichlor-2-(2-pyrazinyl)-acetophenon-0-(2,4-dichlorbenzyl)-oxim als gelbliches OeI.6 g of 2 ', 4 ■ -Dichloro-2- (2-pyrazinyl) -acetophenone oxime are dissolved in 80 ml of dimethylformamide and treated with 1.25 g of sodium hydride (approx. 50% dispersion in mineral oil). After stirring for 1 hour at room temperature, 5.2 g of 2,4-dichlorobenzyl chloride are added and the mixture is left for 16 hours react at room temperature. Then the reaction mixture is poured onto ice water and extracted with ethyl acetate, and the organic phase is dried over anhydrous sodium sulfate and concentrated. The raw product will subjected to column chromatography on silica gel with ethyl acetate / n-hexane (1: 1). The 2 ', 4'-dichloro-2- (2-pyrazinyl) acetophenone-0- (2,4-dichlorobenzyl) oxime is obtained as a yellowish oil.
Auf analoge Weise erhält man:
20In an analogous way one obtains:
20th
aus 2',4'-Dichlor-2-(3-pyridyl)-acetophenonoxim und Benzylchlorid das 2',4'-Dichlor-2-(3-pyridyl)-acetophenon-O-benzyloxim als gelbliches OeI undfrom 2 ', 4'-dichloro-2- (3-pyridyl) acetophenone oxime and Benzyl chloride 2 ', 4'-dichloro-2- (3-pyridyl) -acetophenone-O-benzyloxime as yellowish oil and
aus 2',4'-Dichlor-2-(3-pyridyl)-acetophenonoxim und 3-Picolylchlorid-hydrochlorid das 2',4'-Dichlor-2-(3-pyridyl )-acetophenon-0-(3-pyridylmethyl)oxim als OeI.from 2 ', 4'-dichloro-2- (3-pyridyl) acetophenone oxime and 3-picolyl chloride hydrochloride the 2 ', 4'-dichloro-2- (3-pyridyl ) -acetophenone-0- (3-pyridylmethyl) oxime as an oil.
3 g 2',4'-Dichlor-2-(2-pyrazinyl)-acetophenonoxim werden in 20 ml Pyridin gelöst und mit 0,7 g Methylisocyanat versetzt. Nach 2 Stunden Rühren bei Raumtemperatur wird nochmals 0,7 g Methylisocyanat zugefügt. Nach weiteren 2 Stunden wird auf Eiswasser gegossen und mit Aethylacetat extrahiert. Die organische Phase wird über wasserfreiem Natriumsulfat getrocknet und anschliessend eingeengt. Der Rückstand wird einer Säulenchromatographie an Kieselgel mit3 g of 2 ', 4'-dichloro-2- (2-pyrazinyl) acetophenone oxime are dissolved in 20 ml of pyridine and treated with 0.7 g of methyl isocyanate. After stirring for 2 hours at room temperature another 0.7 g of methyl isocyanate is added. After a further 2 hours, the mixture is poured onto ice water and treated with ethyl acetate extracted. The organic phase is dried over anhydrous sodium sulfate and then concentrated. Of the The residue is column chromatography on silica gel with
3310U83310U8
Aethylacetat/n-Hexan (1:1) unterworfen. Man erhält das 2,4-Dich1or-2-(2-pyrazinyl)-acetophenon-O-t(methylamino)-carbonyl]-oxim als gelbliches OeI.Ethyl acetate / n-hexane (1: 1) subjected. You get that 2,4-dichloro-2- (2-pyrazinyl) acetophenone-O- t (methylamino) carbonyl] oxime as a yellowish oil.
3 g 2-(2-Pyrazinyl)-acetophenon und 2,5 g O-Methylhydroxylamin-hydrochlorid werden in 10 ml Pyridin während 30 Minuten auf 800C erhitzt. Dann wird das Pyridin unter vermindertem Druck abdestilliert, der verbleibende Rückstand mit Wasser versetzt und die wässrige Phase mit Aethyl· acetat extrahiert. Die organische Phase wird sodann über wasserfreiem Natriumsulfat getrocknet und das Lösungsmittel entfernt. Als Rückstand erhält man das 2-(2-Pyrazinyl)-acetophenon-0-methyloxim in Form eines gelblichen OeIs.3 g of 2- (2-pyrazinyl) -acetophenone and 2.5 g of O-methylhydroxylamine hydrochloride are heated in 10 ml of pyridine for 30 minutes at 80 0 C. The pyridine is then distilled off under reduced pressure, water is added to the residue that remains and the aqueous phase is extracted with ethyl acetate. The organic phase is then dried over anhydrous sodium sulfate and the solvent is removed. The residue obtained is 2- (2-pyrazinyl) acetophenone-0-methyloxime in the form of a yellowish oil.
Auf analoge Weise erhält man:In an analogous way one obtains:
aus 2',5'-Dichlor-2-(2-pyrazinyl)-acetophenon und O-Methylhydroxylamin-hydrochlorid das 2',5■-Dichlor-2-(2-pyrazinyl)-acetophenon-O-methyloxim als gelbliches OeI,of 2 ', 5'-dichloro-2- (2-pyrazinyl) -acetophenone and O-methylhydroxylamine hydrochloride, the 2', 5 ■ dichloro-2- (2-pyrazinyl) acetophenone-O-methyloxime as a yellowish oil,
aus 3'-Chlor-2-(2-pyrazinyl)-acetophenon und O-Methylhydroxylamin-hydrochlorid das 3·-Chlor-2-(2-pyrazinyl)-acetophenon-O-methyloxim als gelbliches OeI,from 3'-chloro-2- (2-pyrazinyl) acetophenone and O-methylhydroxylamine hydrochloride the 3 · chloro-2- (2-pyrazinyl) -acetophenone-O-methyloxime as yellowish oil,
aus 2',4'-Dimethyl-2-(2-pyrazinyl)-acetophenon und O-Methylhydroxylamin-hydrochlorid das 2',4'-Dimethyl-2-( 2-pyrazinyl)-acetophenon-O-methyloxim als gelbliches OeI,from 2 ', 4'-dimethyl-2- (2-pyrazinyl) acetophenone and O-methylhydroxylamine hydrochloride the 2 ', 4'-dimethyl-2- ( 2-pyrazinyl) -acetophenone-O-methyloxime as yellowish oil,
aus 4'-Methoxy-2-(2-pyrazinyl)-acetophenon und O-Methylhydroxylamin-hydrochlorid das 4*-Methoxy-2-(2-pyrazinyl)-acetophenon-O-methyloxim, Smp. 58-600C, 35from 4'-methoxy-2- (2-pyrazinyl) -acetophenone and O-methylhydroxylamine hydrochloride the 4 * -methoxy-2- (2-pyrazinyl) -acetophenone-O-methyloxime, m.p. 58-60 0 C, 35
aus 2-(2-Pyrazinyl)-4'-trifluormethyl-acetophenon und O-Methylhydroxylamin-hydrochlorid das 2-(2-Pyrazinyl)-4'-trifluormethyl-acetophenon-O-methyloxim, Smp. 45-47°C,from 2- (2-pyrazinyl) -4'-trifluoromethyl-acetophenone and O-methylhydroxylamine hydrochloride 2- (2-pyrazinyl) -4'-trifluoromethyl-acetophenone-O-methyloxime, M.p. 45-47 ° C,
3310H83310H8
aus 3■,4■-Dichlor-2-(2-pyrazinyl)-acetophenon und O-Methylhydroxylamin-hydrochlorid das 3',4'-Dichlor-2-(2-pyrazinyl)-acetophenon-O-methyloxim als gelbliches OeI,from 3 ■, 4 ■ -Dichloro-2- (2-pyrazinyl) -acetophenone and O-methylhydroxylamine hydrochloride 3 ', 4'-dichloro-2- (2-pyrazinyl) -acetophenone-O-methyloxime as yellowish oil,
aus 4'-Chlor-2'-Methoxy-2-(2-pyrazinyl)-acetophenon und O-Methylhydroxylamin-hydrochlorid das 4'-Chlor-2'-methoxy-2-(2-pyrazinyl)-acetophenon-O-methyloxim als gelbliches OeI,from 4'-chloro-2'-methoxy-2- (2-pyrazinyl) acetophenone and O-methylhydroxylamine hydrochloride 4'-chloro-2'-methoxy-2- (2-pyrazinyl) -acetophenone-O-methyloxime as yellowish oil,
aus 2',4'-Dichlor-2-(6-methyl-2-pyrazinyl)-acetophenon und O-Methylhydroxylamin-hydrochlorid das 2',4'-Dichlor-2-(6-methyl-2-pyrazinyl)-acetophenon-O-methyloxim als gelbliches OeI1 from 2 ', 4'-dichloro-2- (6-methyl-2-pyrazinyl) -acetophenone and O-methylhydroxylamine hydrochloride, the 2', 4'-dichloro-2- (6-methyl-2-pyrazinyl) -acetophenone -O-methyloxime as a yellowish oil 1
aus 21,4'-Dichlor-2-(5-methyl-2-pyrazinyl)-acetophenon und O-Methylhydroxylamin-hydrochlorid das 2',4'-Dichlor-2-(5-methyl-2-pyrazinyl)-acetophenon-O-methyloxim als gelbliches OeI,from 2 1 , 4'-dichloro-2- (5-methyl-2-pyrazinyl) -acetophenone and O-methylhydroxylamine hydrochloride the 2 ', 4'-dichloro-2- (5-methyl-2-pyrazinyl) -acetophenone -O-methyloxime as a yellowish oil,
aus 2',4'-Dichlor-2-(3-pyridyl)-acetophenon und O-(2,6-Dichlorbenzyl)-hydroxylamin-hydrochlorid das 2',4'-Dichlor-2-(3-pyridyl)-acetophenon-0-(2,6-dichlorbenzyl)-oxim als gelbliches OeI,from 2 ', 4'-dichloro-2- (3-pyridyl) acetophenone and O- (2,6-dichlorobenzyl) hydroxylamine hydrochloride the 2 ', 4'-dichloro-2- (3-pyridyl) acetophenone-0- (2,6-dichlorobenzyl) oxime as yellowish oil,
aus 4'-Nitro-2-(3-pyridyl)-acetophenon und O-Methylhydroxylamin-hydrochlorid das 4'-Nitro-2-(3-pyridyl)-acetophenon-O-methyloxim, Smp. 114-116°C,from 4'-nitro-2- (3-pyridyl) acetophenone and O-methylhydroxylamine hydrochloride the 4'-nitro-2- (3-pyridyl) -acetophenone-O-methyloxime, M.p. 114-116 ° C,
aus 2',4'-Dichlor-2-(3-pyridyl)-acetophenon und O-Phenylhydroxylamin-hydrochlorid das 2',4'-Dichlor-2-(3-pyridyl)-acetophenon-O-phenyloxim als gelbliches OeI,from 2 ', 4'-dichloro-2- (3-pyridyl) acetophenone and O-phenylhydroxylamine hydrochloride the 2 ', 4'-dichloro-2- (3-pyridyl) -acetophenone-O-phenyloxime as yellowish oil,
aus 2*,4'-Dichlor-2-(3-pyridyl)-4-pentenophenon und O-Methylhydroxylamin-hydrochlorid das 2',4'-Dichlor-2-(3-pyridyl)-4-pentenophenon-O-methyloxim als OeI und 35from 2 *, 4'-dichloro-2- (3-pyridyl) -4-pentenophenone and O-methylhydroxylamine hydrochloride the 2 ', 4'-dichloro-2- (3-pyridyl) -4-pentenophenone-O-methyloxime as OeI and 35
aus 2',4'-Dichlor-2-(3-pyridyl)-4-pentinophenon und O-Methylhydroxylamin-hydrochlorid das 2',4'-Dichlor-2-(3-pyridyl)-4-pentinophenon-O-methyloxim als bräunliches OeI.from 2 ', 4'-dichloro-2- (3-pyridyl) -4-pentinophenone and O-methylhydroxylamine hydrochloride the 2 ', 4'-dichloro-2- (3-pyridyl) -4-pentinophenone-O-methyloxime as a brownish oil.
3310U83310U8
1 g l-(2,4-Dichlorphenyl)-2-(3-pyridyl)-glyoxal-1-0-methyloxim wird in 10 ml Methanol gelöst und mit 0,18 g Natriumborhydrid versetzt. Nach ca. 2 Stunden Reaktionszeit bei Raumtemperatur wird auf Wasser gegossen und mit Aethylacetat extrahiert. Die organische Phase wird über wasserfreiem Natriumsulfat getrocknet und eingeengt. Man erhält das 2',4'-Dichlor-2-(3-pyridyl)-glykolophenon-O-methyloxim als gelbliches OeI.1 g of 1- (2,4-dichlorophenyl) -2- (3-pyridyl) -glyoxal-1-0-methyloxime is dissolved in 10 ml of methanol and mixed with 0.18 g of sodium borohydride. After a reaction time of approx. 2 hours at room temperature it is poured onto water and extracted with ethyl acetate. The organic phase is over dried anhydrous sodium sulfate and concentrated. The 2 ', 4'-dichloro-2- (3-pyridyl) -glycolophenone-O-methyloxime is obtained as a yellowish oil.
10 g 2',4'-Dichlor-2-(3-pyridyl)-acetophenon-O-methyl-•J5 oxim, 7,1 g N-Bromsuccinimid und 50 mg Dibenzoylperoxid werden in 100 ml Tetrachlorkohlenstoff während 3 Stunden unter Rückfluss erhitzt, dann nochmals 4,5 g N-Bromsuccinimid zugefügt und weitere 2 Stunden erhitzt. Das Reaktionsgemisch wird dann filtriert und das Filtrat auf Natriumbicarbonatlösung gegossen und mit Aethylacetat extrahiert. Das nach Entfernen des Lösungsmittels verbliebene Rohprodukt wird an Kieselgel mit n-Hexan/Aethylacetat (1:1) chromatographiert. Man erhält das 2-Brom-2',4'-dichlor-2-(3-pyridyl)-acetophenon-O-methyloxim wird als gelbliches, wenig stabi-· 1 es OeI.10 g of 2 ', 4'-dichloro-2- (3-pyridyl) acetophenone-O-methyl- • J5 oxime, 7.1 g of N-bromosuccinimide and 50 mg of dibenzoyl peroxide are dissolved in 100 ml of carbon tetrachloride for 3 hours heated under reflux, then another 4.5 g of N-bromosuccinimide were added and the mixture was heated for a further 2 hours. The reaction mixture is then filtered and the filtrate poured onto sodium bicarbonate solution and extracted with ethyl acetate. That after Removal of the solvent remaining crude product is chromatographed on silica gel with n-hexane / ethyl acetate (1: 1). The 2-bromo-2 ', 4'-dichloro-2- (3-pyridyl) acetophenone-O-methyloxime is obtained appears as a yellowish, less stable oil.
2,8 g dieses OeIs wird in 20 ml Aethylacetat aufgenommen und bei 00C mit 0,74 g konzentrierter Schwefelsäure versetzt. Nach 1 Stunde Rühren bei Raumtemperatur wird das Lösungsmittel entfernt. Als-Rückstand erhält man das 2-Brom-2',4'-dichlor-2-(3-pyridyl)-acetophenon-O-methyloximsulfat in Form eines wachsartigen Feststoffes.2.8 g of this ÖIS is taken up in 20 ml ethyl acetate and added at 0 0 C with 0.74 g of concentrated sulfuric acid. After stirring for 1 hour at room temperature, the solvent is removed. The residue obtained is 2-bromo-2 ', 4'-dichloro-2- (3-pyridyl) acetophenone-O-methyloxime sulfate in the form of a waxy solid.
3 g 2',4'-Dichlor-2-(3-pyridyl)-acetophenonoxim werden3 g of 2 ', 4'-dichloro-2- (3-pyridyl) -acetophenone oxime become
in 20 ml Pyridin gelöst und mit 1,8g Benzoylchlorid versetzt. Dann wird 24 Stunden bei Raumtemperatur gerührt unddissolved in 20 ml of pyridine and treated with 1.8 g of benzoyl chloride. The mixture is then stirred at room temperature for 24 hours and
anschliessend das Reaktionsgemisch unter vermindertem Druck eingeengt. Anschliessend wird in ln-Natronlauge aufgenommen und mit Methylenchlorid extrahiert. Nach Entfernen des Lösungsmittels erhält man ein Rohprodukt, das durch Chromatographie an Kieselgel mit n-Hexan/Aethylacetat (1:1) gereinigt wird. Man erhält das 2' ,4'-Dichlor-2-(3-pyridyl)-acetophenon-O-benzoyloxim als bräunliches OeI.the reaction mixture is then concentrated under reduced pressure. It is then taken up in 1N sodium hydroxide solution and extracted with methylene chloride. After removing the solvent, a crude product is obtained which is purified by chromatography on silica gel with n-hexane / ethyl acetate (1: 1). The 2 ', 4'-dichloro-2- (3-pyridyl) -acetophenone-O-benzoyloxime is obtained as a brownish oil.
Auf analoge Weise erhält man aus 2 ' , 4 ' -Dich'lor-2-( 3-pyridyl)-acetophenonoxim und Crotonsäurechlorid das 2',4·— Dichlor-2-(3-pyridyl)-acetophenon-O-crotonyloxim als bräunliches OeI.In an analogous manner, 2 ', 4' -Dich'lor-2- (3-pyridyl) -acetophenone oxime is obtained and crotonic acid chloride the 2 ', 4 · - Dichloro-2- (3-pyridyl) -acetophenone-O-crotonyloxime as brownish oil.
II. Formulierungsbeispiele II. Formulation Examples
1. Spritzpulver (für flüssige oder unter 750C schmelzende Wirkstoffe)1. Wettable powder (for active ingredients that are liquid or that melt below 75 ° C)
Wirkstoff der Formel I 50Active ingredient of formula I 50
Hydratisierte Kieselsäure 37Hydrated silica 37
Kaolin 5Kaolin 5
Alkylphenolathoxylat 4Alkyl phenolate oxylate 4
Natrium-polynaphthalinsulfonat 4 Sodium polynaphthalene sulfonate 4
100100
Der flüssige oder geschmolzene Wirkstoff wird auf die Kieselsäure aufgezogen, die übrigen Komponenten zugemischt und das Ganze in einer geeigneten Mühle feingemahlen. The liquid or molten active ingredient is applied to the The silica is absorbed, the other components are mixed in and the whole thing is finely ground in a suitable mill.
3310U83310U8
2. Spritzpulver (für feste, über 750C schmelzende Wirkstoffe) 2. Wettable powder (for solid active ingredients that melt above 75 0 C)
Wirkstoff der Formel I 50Active ingredient of formula I 50
Hydratisierte Kieselsäure 5Hydrated silica 5
Kaolin 42Kaolin 42
Natrium-laurylsulfat ISodium Lauryl Sulphate I.
Natrium-1ignosulfonat 2Sodium lignosulfonate 2
100100
Die Komponenten werden miteinander vermischt und das Ganze in einer geeigneten Mühle feingemahlen.The components are mixed together and the whole thing finely ground in a suitable mill.
Emulgierbares Konzentrat (für bei 20-250C flüssigeEmulsifiable concentrate (liquid at 20-25 0 C for
Wirkstoffe)Active ingredients)
Gewichtsteile Wirkstoff der Formel I Ricinusöl-äthoxylat CaIcium-dodecylbenzolsulfonat Part by weight of active ingredient of the formula I castor oil ethoxylate calcium dodecylbenzenesulfonate
Gemisch von C,„-Alkylbenzolen ad 1000 Vol.-TeileMixture of C, "- alkylbenzenes to 1000 parts by volume
Die Komponenten werden miteinander vermischt, bis eine klare Lösung entsteht.The components are mixed together until a clear solution emerges.
Claims (15)
R C CH R2 R 3
RC CH R 2
R 3-Pyridyl, 3-Pyridyl-l-oxid, 2-Pyrazinyl, 2-Pyrazinyl-l-oxid, 2-Pyrazinyl-a nitro group are selected, 2
R 3-pyridyl, 3-pyridyl-1-oxide, 2-pyrazinyl, 2-pyrazinyl-1-oxide, 2-pyrazinyl
R unsubstituiertes oder mit Halogen,represents where
R unsubstituted or with halogen,
R unsubstituiertes C, 6-Alkyl, C3_6~Cycloalkyl, C3 ,-Alkenyl oder C3 --Alkinyl bedeuten, R nur 3-Halophenyl, 2,3-, 2,5-, 3,4- oder 3,5-Dihalophenyl oder 2,3,4-, 2,3,5- oder 2,4,5-Trihalophenyl sein kann,5
R is unsubstituted C, 6 alkyl, C 3 _ 6 ~ cycloalkyl, C 3 -alkenyl or C 3 --Alkinyl, R a 3-halophenyl, 2,3-, 2,5-, 3,4- or 3 , 5-dihalophenyl or 2,3,4-, 2,3,5- or 2,4,5-trihalophenyl,
und R eine GruppeBromine or hydroxy means 4
and R is a group
und R unsubstituiertes C,_6-Alkyl, C^g-Cycloalkyl, C3 g-Alkenyl oder C3 --Alkinyl bedeuten, R nur 3-5
and R is unsubstituted C, _ 6 alkyl, C ^ g-cycloalkyl, C3-g alkenyl or C 3 --Alkinyl, R only 3-
R 3-Pyridyl, 3-Pyridyl-l-oxid, 2-Pyrazinyl, 2-Pyrazinyl-l-oxid, 2-Pyrazinyl-a nitro group are selected, 2
R 3-pyridyl, 3-pyridyl-1-oxide, 2-pyrazinyl, 2-pyrazinyl-1-oxide, 2-pyrazinyl
und R eine GruppeBromine or hydroxy means 4
and R is a group
R unsubstituiertes oder mit Halogen,represents where
R unsubstituted or with halogen,
und R unsubstituiertes C,_ß-Alkyl, C^g-Cycloalkyl,R is hydrogen or C. 1-alkyl, R is a group (a) 5
and R unsubstituted C, _ ß- alkyl, C ^ g -cycloalkyl,
OHN
OH
und Y eine Abgangsgruppe bedeutet, bzw. mit einem reaktionsfähigen Derivat einer Säure der allgemeinen Formelwherein R has the meaning given above for R except optionally substituted aryl
and Y denotes a leaving group, or with a reactive derivative of an acid of the general formula
R ONH2 VI5 "
R ONH 2 VI
R , R und R die oben angegebenen Bedeu-12 '4
R, R and R mean the above
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CH650253A5 (en) * | 1982-03-26 | 1985-07-15 | Hoffmann La Roche | PYRIDINE AND PYRAZINE DERIVATIVES AND THEIR USE AS FUNGICIDAL ACTIVE SUBSTANCES. |
JP2765876B2 (en) * | 1988-10-24 | 1998-06-18 | 科研製薬株式会社 | Pyridyl ketoxime ether derivatives |
EP2687088B1 (en) * | 2011-03-18 | 2018-08-01 | Nippon Soda Co., Ltd. | Aqueous horticultural microbicidal composition suspension |
CN103819408B (en) * | 2014-03-13 | 2015-08-05 | 山东理工大学 | Nitro imidazole derivatives and its production and use |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1809385A1 (en) * | 1968-11-16 | 1970-06-11 | Bayer Ag | Oxime-O-carbonic acid phenyl ester and process for their preparation |
US3903303A (en) * | 1970-07-06 | 1975-09-02 | Stauffer Chemical Co | Controlling fungi and bacteria with certain oxime esters |
US4061764A (en) * | 1972-08-02 | 1977-12-06 | Abbott Laboratories | Certain O-substituted thiophene oxime carbamates used as antibacterial and antifungal agents |
EP0006254A1 (en) * | 1978-06-08 | 1980-01-09 | Shell Internationale Researchmaatschappij B.V. | Benzoin oxime derivatives, process for their preparation, compositions containing such derivatives and method for their use as fungicides |
EP0007679A1 (en) * | 1978-07-25 | 1980-02-06 | Acf Chemiefarma Nv | Oxime ethers, processes for their manufacture and pharmaceutical compositions thereof |
EP0049854A2 (en) * | 1980-10-10 | 1982-04-21 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pyridine and pyrazine derivatives, preparation of these compounds, fungicidal agents containing these compounds as active ingredients, and the use of such compounds or agents as fungicides in agriculture and in horticulture |
-
1983
- 1983-03-17 IT IT20124/83A patent/IT1172404B/en active
- 1983-03-21 DE DE19833310148 patent/DE3310148A1/en not_active Withdrawn
- 1983-03-29 FR FR8305129A patent/FR2524466A1/en not_active Withdrawn
- 1983-03-30 GB GB08308866A patent/GB2117772B/en not_active Expired
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1809385A1 (en) * | 1968-11-16 | 1970-06-11 | Bayer Ag | Oxime-O-carbonic acid phenyl ester and process for their preparation |
US3903303A (en) * | 1970-07-06 | 1975-09-02 | Stauffer Chemical Co | Controlling fungi and bacteria with certain oxime esters |
US4061764A (en) * | 1972-08-02 | 1977-12-06 | Abbott Laboratories | Certain O-substituted thiophene oxime carbamates used as antibacterial and antifungal agents |
EP0006254A1 (en) * | 1978-06-08 | 1980-01-09 | Shell Internationale Researchmaatschappij B.V. | Benzoin oxime derivatives, process for their preparation, compositions containing such derivatives and method for their use as fungicides |
EP0007679A1 (en) * | 1978-07-25 | 1980-02-06 | Acf Chemiefarma Nv | Oxime ethers, processes for their manufacture and pharmaceutical compositions thereof |
EP0049854A2 (en) * | 1980-10-10 | 1982-04-21 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pyridine and pyrazine derivatives, preparation of these compounds, fungicidal agents containing these compounds as active ingredients, and the use of such compounds or agents as fungicides in agriculture and in horticulture |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0445069A1 (en) * | 1990-02-16 | 1991-09-04 | Ciba-Geigy Ag | Heterocyclic compounds |
Also Published As
Publication number | Publication date |
---|---|
GB2117772A (en) | 1983-10-19 |
GB8308866D0 (en) | 1983-05-11 |
GB2117772B (en) | 1985-08-14 |
FR2524466A1 (en) | 1983-10-07 |
IT1172404B (en) | 1987-06-18 |
IT8320124A0 (en) | 1983-03-17 |
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