WO1995006033A1 - Derives d'acide 2-oximino-2-pyridylacetique utilises comme agents de lutte contre les parasites (fongicides) - Google Patents
Derives d'acide 2-oximino-2-pyridylacetique utilises comme agents de lutte contre les parasites (fongicides) Download PDFInfo
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- WO1995006033A1 WO1995006033A1 PCT/EP1994/002689 EP9402689W WO9506033A1 WO 1995006033 A1 WO1995006033 A1 WO 1995006033A1 EP 9402689 W EP9402689 W EP 9402689W WO 9506033 A1 WO9506033 A1 WO 9506033A1
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- 239000003096 antiparasitic agent Substances 0.000 title abstract 2
- 229940125687 antiparasitic agent Drugs 0.000 title abstract 2
- 239000000417 fungicide Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 161
- 238000000034 method Methods 0.000 claims abstract description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 156
- -1 phenoxy, benzyl Chemical group 0.000 claims description 111
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 125000005843 halogen group Chemical group 0.000 claims description 59
- 125000001188 haloalkyl group Chemical group 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 22
- 239000003085 diluting agent Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 11
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 11
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000012038 nucleophile Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 5
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims description 5
- 239000012433 hydrogen halide Substances 0.000 claims description 5
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 5
- 238000006146 oximation reaction Methods 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- BPSNETAIJADFTO-UHFFFAOYSA-N 2-pyridinylacetic acid Chemical class OC(=O)CC1=CC=CC=N1 BPSNETAIJADFTO-UHFFFAOYSA-N 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
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- 125000005336 allyloxy group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 4
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 150000002443 hydroxylamines Chemical class 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- XYJQTXWRLKINIE-UHFFFAOYSA-N pyridine-2-carbonyl cyanide Chemical class N#CC(=O)C1=CC=CC=N1 XYJQTXWRLKINIE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000011260 aqueous acid Substances 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 150000002905 orthoesters Chemical class 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
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- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
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- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 9
- 241000607479 Yersinia pestis Species 0.000 claims 3
- 241000790917 Dioxys <bee> Species 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- OSCFQSXLUMRJSK-UHFFFAOYSA-N 2-oxo-2-pyridin-2-ylacetic acid Chemical class OC(=O)C(=O)C1=CC=CC=N1 OSCFQSXLUMRJSK-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 2
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- 239000007858 starting material Substances 0.000 description 23
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- 229960000892 attapulgite Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- NFGNZNFBQAGBJA-UHFFFAOYSA-N butan-2-yl nitrite Chemical compound CCC(C)ON=O NFGNZNFBQAGBJA-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- MFKHKJMRWGOTHL-UHFFFAOYSA-M ethyl(trioctyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CC)(CCCCCCCC)CCCCCCCC MFKHKJMRWGOTHL-UHFFFAOYSA-M 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical class Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- APNSGVMLAYLYCT-UHFFFAOYSA-N isobutyl nitrite Chemical compound CC(C)CON=O APNSGVMLAYLYCT-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- AVHFSOIZCRXLQW-UHFFFAOYSA-N methyl 2-[2-(3,4-dichlorophenoxy)pyridin-3-yl]-2-methoxyiminoacetate Chemical compound COC(C(C=1C(=NC=CC=1)OC1=CC(=C(C=C1)Cl)Cl)=NOC)=O AVHFSOIZCRXLQW-UHFFFAOYSA-N 0.000 description 1
- FJXIEGWDAMMPBX-UHFFFAOYSA-N methyl 2-[2-(3-bromophenoxy)pyridin-3-yl]-2-methoxyiminoacetate Chemical compound COC(C(C=1C(=NC=CC=1)OC1=CC(=CC=C1)Br)=NOC)=O FJXIEGWDAMMPBX-UHFFFAOYSA-N 0.000 description 1
- RNUYCQTVMQAGFE-UHFFFAOYSA-N methyl 2-[2-(3-chlorophenoxy)pyridin-3-yl]-2-methoxyiminoacetate Chemical compound COC(C(C=1C(=NC=CC=1)OC1=CC(=CC=C1)Cl)=NOC)=O RNUYCQTVMQAGFE-UHFFFAOYSA-N 0.000 description 1
- UMEXYUUICJHGNV-UHFFFAOYSA-N methyl 2-[2-(4-tert-butylphenoxy)pyridin-3-yl]-2-methoxyiminoacetate Chemical compound COC(C(C=1C(=NC=CC=1)OC1=CC=C(C=C1)C(C)(C)C)=NOC)=O UMEXYUUICJHGNV-UHFFFAOYSA-N 0.000 description 1
- BMRBYVRUALLDLO-UHFFFAOYSA-N methyl 2-[2-[(6-chloropyridin-3-yl)-methylamino]pyridin-3-yl]-2-methoxyiminoacetate Chemical compound COC(C(=NOC)C=1C(=NC=CC1)N(C)C=1C=CC(=NC1)Cl)=O BMRBYVRUALLDLO-UHFFFAOYSA-N 0.000 description 1
- RXYYTDQYZLENOO-UHFFFAOYSA-N methyl 2-[3-[(3-chlorophenoxy)methyl]pyridin-2-yl]-2-oxoacetate Chemical compound COC(C(=O)C1=NC=CC=C1COC1=CC(=CC=C1)Cl)=O RXYYTDQYZLENOO-UHFFFAOYSA-N 0.000 description 1
- REPLFBYXWJHWFE-UHFFFAOYSA-N methyl 2-[5-(4-chlorophenyl)pyridin-3-yl]oxy-3-methoxyprop-2-enoate Chemical compound COC=C(C(=O)OC)OC1=CN=CC(C=2C=CC(Cl)=CC=2)=C1 REPLFBYXWJHWFE-UHFFFAOYSA-N 0.000 description 1
- KDVURCHSMVMVLX-UHFFFAOYSA-N methyl 2-methoxyimino-2-(2-phenoxypyridin-3-yl)acetate Chemical compound COC(C(C=1C(=NC=CC=1)OC1=CC=CC=C1)=NOC)=O KDVURCHSMVMVLX-UHFFFAOYSA-N 0.000 description 1
- WRRREGUGEWIJRU-UHFFFAOYSA-N methyl 2-methoxyimino-2-[2-(3-methylphenoxy)pyridin-3-yl]acetate Chemical compound COC(C(C=1C(=NC=CC=1)OC1=CC(=CC=C1)C)=NOC)=O WRRREGUGEWIJRU-UHFFFAOYSA-N 0.000 description 1
- ITOLRAHEDDXNEM-UHFFFAOYSA-N methyl 3-methoxy-2-(6-phenylpyridin-2-yl)sulfanylprop-2-enoate Chemical compound COC=C(C(=O)OC)SC1=CC=CC(C=2C=CC=CC=2)=N1 ITOLRAHEDDXNEM-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material 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
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229940093956 potassium carbonate Drugs 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- PGSZYKMIHRQVPD-UHFFFAOYSA-M sodium;2-hydroxy-5-methylbenzoate Chemical compound [Na+].CC1=CC=C(O)C(C([O-])=O)=C1 PGSZYKMIHRQVPD-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- VCZQFJFZMMALHB-UHFFFAOYSA-N tetraethylsilane Chemical compound CC[Si](CC)(CC)CC VCZQFJFZMMALHB-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- SDSMZSUWTYFEBO-UHFFFAOYSA-M tributyl(methyl)phosphanium;bromide Chemical compound [Br-].CCCC[P+](C)(CCCC)CCCC SDSMZSUWTYFEBO-UHFFFAOYSA-M 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- 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
-
- 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
Definitions
- the invention relates to new 2-oximino-2-pyridyl-acetic acid derivatives, several processes for their preparation and their use as pesticides, in particular as fungicides.
- Ar represents optionally substituted aryl or heteroaryl
- R represents alkyl or haloalkyl
- R 2 and R 3 independently of one another each represent hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkynyl, alkynyloxy, haloalkyl, haloalkoxy, haloalkylthio, haloalkenyl, haloalkenyloxy, haloalkynyl, haloalkynyloxy, alkoxycarbonyl,
- Hydroximinoalkyl alkoximinoalkyl or optionally substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy,
- Z represents a radical of the formula -OR 5 or -NR 6 R 7 , where
- R 4 represents alkyl, haloalkyl, cycloalkyl or cyano
- R 5 represents alkyl or haloalkyl
- R and R 7 each independently represent hydrogen, alkyl, haloalkyl, alkoxy or haloalkoxy and
- n 0, 1 or 2
- the compounds of the formula (I) can optionally be present as geometric and / or optical isomers or isomer mixtures of different compositions. Both the pure isomers and the isomer mixtures are claimed according to the invention.
- Ar represents optionally substituted aryl or heteroaryl
- R 1 represents alkyl or haloalkyl
- R 2 and R 3 independently of one another each represent hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkynyl, alkynyloxy, haloalkyl, haloalkoxy, haloalkylthio, haloalkenyl, haloalkenyloxy, haloalkynyl, haloalkynyloxy, alkoxycarbonyl, Hydroximinoalkyl, alkoximinoalkyl or optionally substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy,
- Z represents a radical of the formula -OR 5 or -NR 6 R 7 , where
- 'R 4 represents alkyl, haloalkyl, cycloalkyl or cyano
- R 5 represents alkyl or haloalkyl
- R 6 and R 7 each independently represent hydrogen, alkyl, halogen alkyl, alkoxy or haloalkoxy and
- n 0. 1 or 2 get when one
- R 2 , R 3 , Ar, A and Z have the meaning given above,
- R 2 , R 3 , Ar, A and Z have the meaning given above and
- R 8 represents alkyl
- R 1 , R 2 , R 3 and Z have the meaning given above and
- R 4 has the meaning given above, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary,
- R 1 , R 2 , R 3 , R 5 , Ar and A have the meaning given above,
- R 6 and R 7 have the meaning given above
- R 2 , R 3 , Ar, A and Z have the meaning given above, with oximation agents and then with alkylating agents of the formula (VIII)
- R 1 has the meaning given above and
- X represents halogen or the grouping -O-SO 2 -OR 1 ,
- the 2-oximino-2-pyridyl-acetic acid derivatives of the general formula (I) according to the invention show a considerably better activity against microorganisms which damage the plants in comparison to the 2-methoxy-acrylic acid esters known from the prior art, such as, for example, the compound 3- Methyl methoxy-2- (6-phenyl-2-pyridylthio) acrylic acid or the compound 3- methoxy-2- [N- (6-phenyl-2-pyridyl) -N-methylamino] acrylic acid methyl ester or the compound 3- Methyl methoxy-2- [5- (4-chlorophenyl) -3-pyridyloxy] acrylic acid. which are chemically and functionally obvious compounds.
- the 2-oximino-2-pyridyl-acetic acid derivatives according to the invention are generally defined by the formula (I). Compounds of formula (I) are preferred. in which
- Ar for optionally single or multiple, identical or different substituted aryl with 6 to 10 carbon atoms or for optionally single or multiple, identical or different substituted and / or benzo-fused heteroaryl with 2 to 9 carbon atoms and 1 to 5 identical or different heteroatoms stands, with the following being suitable as substituents: halogen, cyano, nitro, hydroxy, amino, formyl, carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio,
- Alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched halogenoalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each with 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or
- Alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, in each case optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 same or different
- R 1 represents straight-chain or branched alkyl having 1 to 8 carbon atoms or straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms,
- R 2 and R 3 independently of one another each represent hydrogen, halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy, alkylthio
- 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy having 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms are substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy
- A represents oxygen, ethene-1,2-diyl, ethyne-1,2-diyl or one of the following
- Z represents a radical of the formula -OR 5 or -NR 6 R 7 , where
- R 4 represents straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, cycloalkyl having 3 to 8 carbon atoms or cyano,
- R 5 represents straight-chain or branched alkyl having 1 to 8 carbon atoms or straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms,
- R 6 and R 7 each independently represent hydrogen, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, or straight-chain or branched alkoxy 1 to 8 carbon atoms stand and
- n 0, 1 or 2
- Ar for optionally single to five times, identical or differently substituted aryl having 6 or 10 carbon atoms or for optionally single to four times, identical or differently substituted and / or benzo-fused Heteroaryl with 2 to 9 carbon atoms and 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur - is available, the following being suitable in each case: halogen, cyano, nitro, hydroxy, amino, formyl, carbamoyl, thiocarbamoyl , in each case straight-chain or branched alkyl, alkoxy, alkylthio,
- Alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each
- R 1 represents straight-chain or branched alkyl having 1 to 6 carbon atoms or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
- R 2 and R 3 independently of one another each represent hydrogen, halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, each with
- each straight-chain or branched alkenyl or alkenyloxy each having 2 to 4 carbon atoms
- each straight-chain or branched haloalkyl each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched haloalkenyl or
- Haloalkenyloxy each having 2 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched alkoxycarbonyl, hydroximinoalkyl or alkoximinoalkyl each having 1 to 4 carbon atoms in the individual alkyl parts and, moreover, in each case optionally in the phenyl part, simply to five times, identical or different from halogen and / or straight-chain or branched alkyl having 1 to 3 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms and / or straight-chain the branched alkoxy having 1 to 3 carbon atoms and / or straight chain or branched
- Z represents a radical of the formula -OR 5 or -NR 6 R 7 , where
- R 4 for straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, represents cycloalkyl having 3 to 7 carbon atoms or cyano
- R 5 for straight-chain or branched alkyl having 1 to 6 carbon atoms or for straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different
- R 6 and R 7 each independently represent hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, or straight-chain or branched alkoxy 1 to 6 carbon atoms are and
- n 0, 1 or 2
- Ar for phenyl or naphthyl which is optionally monosubstituted to trisubstituted identically or differently or for each optionally monosubstituted to trisubstituted and / or substituted in the same or different ways and / or benzo-annelated
- Thiocarbamoyl Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, Methylthio, ethylthio, methylsulfinyl, methylsulfonyl, allyl, butenyl, allyloxy, butenyloxy, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl, Trifluoromethylsulfonyl, dimethylamino, diethylamino, acetyl, acetoxy, methylsulfonyloxy, ethylsulfonyloxy, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, hydro
- R 1 represents straight-chain or branched alkyl having 1 to 4 carbon atoms or haloalkyl having 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms,
- R 2 and R 3 independently of one another each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
- Z represents a radical of the formula -OR 5 or -NR 6 R 7 , where
- R 4 represents methyl, ethyl, trifluoromethyl, cyclopropyl or cyano
- R represents straight-chain or branched alkyl having 1 to 4 carbon atoms or haloalkyl having 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms and
- R 6 and R 7 each independently represent hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, halogeno alkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms or straight-chain or branched alkoxy have 1 to 4 carbon atoms and
- n 0, 1 or 2
- a very particularly preferred group of compounds of the formula (I) are the compounds of the formula (IA)
- A, Ar, R 1 , R 2 , R 3 and Z are those specified above as being particularly preferred
- Particularly preferred groups of compounds of the formula (I) are the compounds of the formulas (IA) to (ID):
- A, Ar, R, R 2, D R3 and Z have the meanings given particularly preferably above.
- Very particularly preferred groups of compounds of the formula (I) are compounds of the formulas (IA-1) to (IA-17):
- Rl l 1, R 2, R 3, R 4, R 6 and Z have the meanings given above as being very particularly preferred.
- Very particularly preferred groups of compounds of the formula (I) are also compounds of the formulas (IB-1) to (IB-17):
- Ar, R, R, R, R, R, R and Z have the meanings given above as being particularly preferred.
- Very particularly preferred groups of compounds of the formula (I) are furthermore compounds of the formulas (IC-1) to (IC 1-17):
- Ar, R 1 , R 2 , R 3 , R 4 , R 6 and Z have the meanings given above as being particularly preferred.
- Very particularly preferred groups of compounds of the formula (I) are also compounds of the formulas (ID-1) to (ID-17):
- R 1 , R 2 , R 3 , R 4 , R 6 and Z have the meanings given above as being particularly preferred.
- Examples of the possible combinations of the compounds of the formulas (IA1) to (ID-17) defined above are listed below, with Z for each of the compounds of the formulas (IA1) to (ID-17) for -OCH 3 and -NHCH 3 where R 4 and R 6 in the examples of formulas (IA, B, C, D-15, 16, 17) is methyl, and R 1 , R 2 , R 3 and Ar are each indicated as follows.
- reaction sequence in process (b) according to the invention can be represented by the following formula:
- reaction sequence in process (d) according to the invention can be represented by the following formula ⁇ make:
- the a-oxopyridyl acetic acid derivatives required as starting compounds for carrying out process (a) according to the invention are generally defined by the formula (IIa) and the corresponding ketals by the formula (IIb).
- R 2 , R 3 , Ar, A and Z preferably or in particular have those meanings which are preferred or particularly preferred in connection with the description of the compounds of the formula (I) according to the invention were preferably given for R 2 , R 3 , Ar, A and Z;
- R 8 preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.
- R 2 , R 3 , R 8 and Z have the meaning given above and
- R 4 has the meaning given above
- reaction auxiliary e.g. Copper (I) chloride
- diluent e.g. Dioxane
- halogenated oxopyridyl acetic acid derivatives of the general formulas (IXa) and (IXb) are not yet known from the literature; as new substances, they are the subject of the present application.
- R 2 and R 3 have the meaning given above and
- hydrolyzed with aqueous acids for example with hydrochloric acid at temperatures between 10 ° C and 100 ° C, then by reaction with alcohols, for example with methanol, optionally in the presence of a reaction auxiliary, such as e.g. Sulfuric acid and optionally in the presence of a diluent, e.g.
- orthoesters for example with trimethyl orthoformate or triethyl ester
- amines for example with methylamine
- halogenated pyridine-carboxylic acid cyanides of the formula (X) are not yet known from the literature; as new substances, they are the subject of the present application.
- metal cyanides for example with copper (I) cyanide, optionally in the presence of a diluent, such as e.g. Acetonitrile, at temperatures between 10 ° C and 100 ° C.
- a diluent such as e.g. Acetonitrile
- halogenated pyridine-carboxylic acid chlorides of the formula (XI) are known and / or can be prepared by processes known per se (cf. DE-OS 2713316, J. Heterocycl. Chem. 25 (1988), 1367-1371).
- Formula (III) provides a general definition of the hydroxylamines further required as starting materials in process (a) according to the invention.
- R 1 preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for R 1 in connection with the description of the compounds of the formula (I) according to the invention.
- Particularly suitable hydrogen halide adducts are the hydrogen chloride and hydrogen bromide adducts.
- the starting materials of formula (III) are known organic synthetic chemicals.
- Formula (IV) provides a general definition of the 2-oximino-2- (halogenopyridyl) acetic acid derivatives to be used as starting compounds for carrying out process (b) according to the invention.
- R 1 , R 2 , R 3 and Z preferably or in particular have the meaning which, in connection with the description of the compounds of the formula (I) according to the invention, is preferred or particularly preferred for R 1 , R 2 , R 3 and Z was specified.
- R 2 , R, R and Z have the meaning given above and
- R 1 has the meaning given above
- reaction auxiliary e.g. Acetic acid
- diluent e.g. Methanol
- Formula (V) generally defines the nucleophiles to be used further as starting compounds for carrying out process (b) according to the invention.
- Ar in formula (V) preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for Ar in connection with the description of the compounds of the formula (I) according to the invention;
- the starting materials of formula (V) are known organic synthetic chemicals.
- Formula (Ia) provides a general definition of the 2-oximino-2-pyridyl-acetic acid derivatives to be used as starting compounds for carrying out process (c) according to the invention.
- R 1 , R 2 , R 3 , R 5 , Ar and A preferably or in particular have the meaning which, in connection with the description of the compounds of the formula (I) according to the invention, is preferred or was given as being particularly preferred for R 1 , R 2 , R 3 , R 5 , Ar and A.
- the starting materials of the formula (Ia) for process (c) are new compounds according to the invention; they can be prepared by processes (a) and (b) according to the invention.
- Formula (VI) provides a general definition of the amines to be used as starting compounds for carrying out process (c) according to the invention.
- R 6 and R 7 preferably or in particular have the meaning which has already been stated as preferred or as particularly preferred for R 6 and R 7 in connection with the description of the compounds of the formula (I) according to the invention has been.
- the starting materials of formula (VI) are known organic synthetic chemicals.
- Formula (VII) provides a general definition of the halogenated 2-pyridyl-acetic acid derivatives to be used as starting compounds for carrying out process (d) according to the invention.
- R 2 , R 3 , Ar, A and Z preferably or in particular have the meaning which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or as particularly preferred for R 2 , R 3 , Ar, A and Z was specified.
- the starting materials of the formula (VII) are known and / or can be prepared by processes known per se (cf. EP-A 243012, EP-A 312243).
- Formula (VIII) provides a general definition of the alkylating agents which are further used as starting compounds for carrying out process (d) according to the invention.
- R 1 preferably or in particular the meaning which has already been given in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R 1 ;
- X preferably represents chlorine, bromine, iodine or the grouping -O-SO 2 -OR 1 .
- the alkylating agents of formula (VIII) are known organic synthesis chemicals.
- Process (a) according to the invention for the preparation of the new 2-oximino-2-pyridylacetic acid derivatives of the formula (I) is preferably carried out using diluents.
- Inert organic solvents are particularly suitable as diluents for carrying out process (a) according to the invention.
- aliphatic, alicyclic or aromatic optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl
- Process (a) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
- a suitable reaction auxiliary All customary inorganic or organic acids are suitable as such. These preferably include protonic acids, for example hydrochloric acid, sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
- reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between 0 ° C and + 150 ° C, preferably at temperatures between 20 ° C and + 120 ° C.
- Process (a) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
- 1.0 to 3.0 mol, preferably 1.0 to 2.0 mol, of hydroxylamine are generally employed per mol of a-oxopyridyl acetic acid derivative of the formula (II) Formula (III) or a corresponding hydrogen halide and optionally 1.0 to 6.0 mol, preferably 1.0 to 3.0 mol, of reaction auxiliaries.
- the reaction is carried out, worked up and isolated by known methods.
- Inert organic solvents are particularly suitable as diluents for carrying out process (b) according to the invention.
- These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as NJM-dimethylformamide, N, N-dimethylacetamide, N-
- the process according to the invention can (b) also be carried out in a two-phase system, such as water / toluene or water / dichloromethane, if appropriate in the presence of a suitable phase transfer catalyst.
- suitable phase transfer catalysts are: tetrabutylammonium iodide, tetrabutylammonium bromide, tetrabutylammonium chloride, tributyl-methylphosphonium bromide, trimethyl-C ⁇ / C ⁇ -alkylammonium chloride, trimethyl-C ⁇ / C j s-alkylammonium bromide, dibenzyl-methyl- 12 -dimethyl-ammonium-dimethyl- 14 -methyl-ammonium-ammonium alkylbenzylammonium chloride, dimethyl-C 12 / C 14 -alkyl-benzylammonium bromide, tetrabutylammonium hydroxide, tri
- Process (b) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
- All customary inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium ⁇ hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N -Dimethylaminopyridine, diazabicyclooctane (
- reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between 0 ° C and + 150 ° C, preferably at temperatures between 20 ° C and + 120 ° C.
- Process (b) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
- organic solvents include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Alcohols, such as methanol, ethanol, n- or i-propanol; Ether like Diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanil
- Process (c) according to the invention is optionally carried out in the presence of a suitable reaction auxiliary.
- All customary inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium ⁇ hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N -Dimethylaminopyridine, diazabicyclooctan
- reaction temperatures can be varied within a substantial range when carrying out process (c) according to the invention. In general, temperatures between -30 ° C and + 150 ° C, preferably at temperatures between -20 ° C and + 120 ° C.
- Process (c) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
- Oximino-2-pyridyl-acetic acid derivative of the formula (Ia) in general 1.0 to 3.0 mol, preferably 1.0 to 1.5 mol of amine of the formula (VI) and optionally 0.1 to 3.0 mol, preferably 0.5 to 1.5 mol of base used as reaction auxiliary on.
- oximizing agents are the reagents suitable for converting methylene compounds into hydroximino compounds.
- suitable oximation agents are: nitrous acid, nitrosyl chloride, alkyl nitrites such as e.g. Methyl, ethyl, n or i propyl, n, i, s and t-butyl nitrite
- Inert organic solvents are particularly suitable as diluents for carrying out process (d) according to the invention.
- These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, NJNf-dimethylacetamide, N
- Process (d) according to the invention is optionally carried out in the presence of a suitable reaction auxiliary.
- All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, Sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate.
- Ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO) , Diazabicyclonones (DBN) or diazabicycloun- decene (DBU).
- reaction temperatures can be varied within a substantial range when carrying out process (d) according to the invention. In general, temperatures between -20 ° C and + 120 ° C, preferably at temperatures between 0 ° C and + 100 ° C.
- the process according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
- the active compounds according to the invention have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
- the active ingredients are suitable for use as crop protection agents, in particular as fungicides.
- Fungicidal agents in crop protection are used to combat plasmidiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes. Deuteromycetes.
- Pythium species such as, for example, Pythium ultimum
- Phytophthora species such as, for example, Phytophthora infestans
- Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseu ⁇ doperonospora cubense;
- Plasmopara species such as, for example, Plasmopara viticola
- Peronospora species such as, for example, Peronospora pisi or Peronospora brassicae;
- Erysiphe species such as, for example, Erysiphe graminis
- Sphaerotheca species such as, for example, Sphaerotheca fuliginea
- Podosphaera species such as, for example, Podosphaera leucotricha
- Venturia species such as, for example, Venturia inaequalis
- Pyrenophora species such as, for example, Pyrenophora teres or Pyrenophora graminea (conidial form: Drechslera, synonym: Helminthosporium);
- Cochliobolus species such as, for example, Cochliobolus sativus (conidial form: Drechs ⁇ lera, synonym: Helminthosporium);
- Uromyces species such as, for example, Uromyces appendiculatus
- Puccinia species such as, for example, Puccinia recondita
- Tilletia species such as, for example, Tilletia caries
- Ustilago species such as, for example, Ustilago nuda or Ustilago avenae
- Pellicularia species such as, for example, Pellicularia sasakii
- Pyricularia species such as, for example, Pyricularia oryzae
- Fusarium species such as, for example, Fusarium culmorum
- Botrytis species such as, for example, Botrytis cinerea
- Septoria species such as, for example, Septoria nodorum
- Leptosphaeria species such as, for example, Leptosphaeria nodorum;
- Cercospora species such as, for example, Cercospora canescens
- Alternaria species such as, for example, Alternaria brassicae;
- Pseudocercosporella species such as, for example, Pseudocercosporella herpotrichoides.
- the active compounds according to the invention can be used with particularly good success for combating diseases in fruit and vegetable cultivation, such as, for example, against Venturia, Uncinula or Podosphaera species, or for controlling cereal diseases, for example against Erysiphe species.
- the active compounds according to the invention have good in vitro activity.
- the active compounds can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV Cold and warm mist formulations.
- These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, under pressure the liquefied gases and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
- extenders that is to say liquid solvents
- surface-active agents ie emulsifiers and / or dispersants and / or foam-generating agents.
- organic solvents can, for example, also be used as auxiliary solvents.
- aromas such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes, or methylene chloride
- aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide, and water
- liquefied gaseous extenders or carriers mean those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide
- Solid carrier materials are suitable: for example natural flour, such as ka
- Alkylaryl polyglycol ethers alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
- the following may be used as dispersants: for example lignin sulfite waste liquor and methyl cellulose.
- Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids.
- Other additives can be mineral and vegetable oils.
- Dyes such as inorganic pigments can be used.
- iron oxide eg iron oxide, titanium oxide, ferrocy blue and organic dyes such as alizarin.
- Azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
- the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
- the active compounds according to the invention can be present in the formulations in a mixture with other known active compounds, such as fungicides, insecticides, acaricides and herbicides, and also in mixtures with fertilizers and growth regulators.
- the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.
- the active compound concentrations in the use forms can be varied within a substantial range: in general they are between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.
- amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
- active ingredient concentrations are from 0.00001 to 0.1% by weight. preferably from 0.0001 to 0.02% by weight required at the site of action.
- Solvent 10 parts by weight of N-methyl-pyrrolidone emulsifier: 0.6 part by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
- the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.
- Evaluation is carried out 7 days after the inoculation.
- Emulsifier 0.3 part by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- the plants are then placed in a greenhouse at 23 ° C. and a relative atmospheric humidity of approx. 70%.
- Evaluation is carried out 10 days after the inoculation.
- the compounds of Preparation Examples 1, 2, 3, 5, 11, 13 and 14 show an efficiency of at least 95% at an active ingredient concentration of 25 ppm.
- Emulsifier 0.3 part by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
- the plants are then placed in the greenhouse at 23.degree. C. to 24.degree. C. and a relative atmospheric humidity of approx. 75%.
- Evaluation is carried out 14 days after the inoculation.
- the compound according to Preparation Example 4 shows an efficiency of at least at an active ingredient concentration of 25 ppm
- Emulsifier 0.3 part by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
- the plants are then placed in a greenhouse at 20 ° C. and a relative atmospheric humidity of approx. 70%.
- Evaluation is carried out 12 days after the inoculation.
- the compounds according to Preparation Examples 2, 3, 4, 5, 6, 7, 8, 10, 11, 12, 13 and 14 show an efficiency of up to 100% at an active ingredient concentration of 10 ppm.
- Emulsifier 0.3 part by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
- the disease infestation is evaluated 4 days after the inoculation.
- the compounds according to Preparation Examples 8, 9 and 11 show efficiencies of 90 to 100% at an active ingredient concentration of 0.025%.
- Emulsifier 0.3 part by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
- the plants are then placed in a greenhouse at 23 to 24 ° C and at a relative humidity of approx. 75%.
- Evaluation is carried out 10 days after the inoculation.
- the compounds of preparation examples 8, 14, 17 and 18 have an efficacy of up to 100% at an active ingredient concentration of 10 ppm.
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Abstract
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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JP7507317A JPH09501685A (ja) | 1993-08-24 | 1994-08-11 | 抗有害生物剤(殺菌・殺カビ剤)としての2−オキシイミノ−2−ピリジル−酢酸誘導体 |
AU76530/94A AU7653094A (en) | 1993-08-24 | 1994-08-11 | 2-oximino-2-pyridyl acetic acid derivatives as anti-parasitic agents (fungicides) |
EP94926831A EP0715621A1 (fr) | 1993-08-24 | 1994-08-11 | Derives d'acide 2-oximino-2-pyridylacetique utilises comme agents de lutte contre les parasites (fongicides) |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DEP4328385.3 | 1993-08-24 | ||
DE19934328385 DE4328385A1 (de) | 1993-08-24 | 1993-08-24 | 2-Oximino-2-pyridyl-essigsäurederivate |
Publications (1)
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WO1995006033A1 true WO1995006033A1 (fr) | 1995-03-02 |
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Family Applications (1)
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PCT/EP1994/002689 WO1995006033A1 (fr) | 1993-08-24 | 1994-08-11 | Derives d'acide 2-oximino-2-pyridylacetique utilises comme agents de lutte contre les parasites (fongicides) |
Country Status (6)
Country | Link |
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EP (1) | EP0715621A1 (fr) |
JP (1) | JPH09501685A (fr) |
CN (1) | CN1133036A (fr) |
AU (1) | AU7653094A (fr) |
DE (1) | DE4328385A1 (fr) |
WO (1) | WO1995006033A1 (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998012179A1 (fr) * | 1996-09-18 | 1998-03-26 | Basf Aktiengesellschaft | Derives de pyridine, leur procede de preparation et leur utilisation pour lutter contre les parasites animaux et les champignons nuisibles |
WO1999040082A3 (fr) * | 1998-02-05 | 1999-10-21 | Basf Ag | Derives de 2-(pyrazolyloxy)-pyridine-3-yle-acide acetique, agents les contenant et leur utilisation pour lutter contre des champignons nuisibles et des parasites animaux |
EP0766673B1 (fr) * | 1994-06-23 | 2002-01-30 | Celltech Chiroscience Limited | Derives d'oximes substitues efficaces en tant qu'inhibiteurs de phosphodiesterases de type iv |
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---|---|---|---|---|
EP0383117A2 (fr) * | 1989-02-17 | 1990-08-22 | Bayer Ag | Esters de l'acide acrylique substitués par une pyridine |
EP0472300A2 (fr) * | 1990-08-22 | 1992-02-26 | Zeneca Limited | Fongicides |
EP0477631A1 (fr) * | 1990-09-22 | 1992-04-01 | BASF Aktiengesellschaft | Amides d'acides phénylacétiques ortho-substitués |
WO1992013830A1 (fr) * | 1991-01-30 | 1992-08-20 | Zeneca Limited | Fongicides |
JPH05201980A (ja) * | 1992-01-30 | 1993-08-10 | Mitsubishi Kasei Corp | メトキシイミノ酢酸誘導体およびこれを有効成分とする農園芸用殺菌剤 |
-
1993
- 1993-08-24 DE DE19934328385 patent/DE4328385A1/de not_active Withdrawn
-
1994
- 1994-08-11 WO PCT/EP1994/002689 patent/WO1995006033A1/fr not_active Application Discontinuation
- 1994-08-11 AU AU76530/94A patent/AU7653094A/en not_active Abandoned
- 1994-08-11 CN CN 94193763 patent/CN1133036A/zh active Pending
- 1994-08-11 JP JP7507317A patent/JPH09501685A/ja active Pending
- 1994-08-11 EP EP94926831A patent/EP0715621A1/fr not_active Withdrawn
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0383117A2 (fr) * | 1989-02-17 | 1990-08-22 | Bayer Ag | Esters de l'acide acrylique substitués par une pyridine |
EP0472300A2 (fr) * | 1990-08-22 | 1992-02-26 | Zeneca Limited | Fongicides |
EP0477631A1 (fr) * | 1990-09-22 | 1992-04-01 | BASF Aktiengesellschaft | Amides d'acides phénylacétiques ortho-substitués |
WO1992013830A1 (fr) * | 1991-01-30 | 1992-08-20 | Zeneca Limited | Fongicides |
JPH05201980A (ja) * | 1992-01-30 | 1993-08-10 | Mitsubishi Kasei Corp | メトキシイミノ酢酸誘導体およびこれを有効成分とする農園芸用殺菌剤 |
Non-Patent Citations (1)
Title |
---|
CHEMICAL ABSTRACTS, vol. 120, no. 11, 14 March 1994, Columbus, Ohio, US; abstract no. 134461f, M. ODA ET AL.: "Preparation of 2-(5-pyrazolyl or 2-pyridyl)-2-(methoxyimino)acetic acid derivatives as agricultural and horticultural fungicides." page 1041; * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0766673B1 (fr) * | 1994-06-23 | 2002-01-30 | Celltech Chiroscience Limited | Derives d'oximes substitues efficaces en tant qu'inhibiteurs de phosphodiesterases de type iv |
WO1998012179A1 (fr) * | 1996-09-18 | 1998-03-26 | Basf Aktiengesellschaft | Derives de pyridine, leur procede de preparation et leur utilisation pour lutter contre les parasites animaux et les champignons nuisibles |
US6228810B1 (en) | 1996-09-18 | 2001-05-08 | Basf Ag | Pyridine derivatives, process for preparing the same and their use for controlling animal pests and harmful fungi |
WO1999040082A3 (fr) * | 1998-02-05 | 1999-10-21 | Basf Ag | Derives de 2-(pyrazolyloxy)-pyridine-3-yle-acide acetique, agents les contenant et leur utilisation pour lutter contre des champignons nuisibles et des parasites animaux |
US6362192B1 (en) | 1998-02-05 | 2002-03-26 | Basf Aktiengesellschaft | 2-(Pyrazolyloxy) -pyridin-3-ylacetic acid derivatives, agents containing the same and use thereof against noxious fungi and animal parasites |
Also Published As
Publication number | Publication date |
---|---|
EP0715621A1 (fr) | 1996-06-12 |
DE4328385A1 (de) | 1995-03-02 |
AU7653094A (en) | 1995-03-21 |
CN1133036A (zh) | 1996-10-09 |
JPH09501685A (ja) | 1997-02-18 |
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