CH603041A5 - N-Furoyl-N-aryl-alanine esters - Google Patents
N-Furoyl-N-aryl-alanine estersInfo
- Publication number
- CH603041A5 CH603041A5 CH159175A CH159175A CH603041A5 CH 603041 A5 CH603041 A5 CH 603041A5 CH 159175 A CH159175 A CH 159175A CH 159175 A CH159175 A CH 159175A CH 603041 A5 CH603041 A5 CH 603041A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- plants
- formula
- compounds
- cooch3
- Prior art date
Links
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- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000004480 active ingredient Substances 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 241000233866 Fungi Species 0.000 claims description 17
- 239000004563 wettable powder Substances 0.000 claims description 15
- 239000000725 suspension Substances 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- -1 1-methoxycarbonyl-ethyl Chemical group 0.000 claims description 9
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- 230000017066 negative regulation of growth Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000008635 plant growth Effects 0.000 claims description 4
- 208000024891 symptom Diseases 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 235000009852 Cucurbita pepo Nutrition 0.000 claims description 2
- 240000001980 Cucurbita pepo Species 0.000 claims description 2
- 241000508723 Festuca rubra Species 0.000 claims description 2
- 241000896246 Golovinomyces cichoracearum Species 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 240000004296 Lolium perenne Species 0.000 claims description 2
- 241000209049 Poa pratensis Species 0.000 claims description 2
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- 239000011248 coating agent Substances 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 241000227653 Lycopersicon Species 0.000 claims 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 68
- 239000000460 chlorine Substances 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 240000003768 Solanum lycopersicum Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000002585 base Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- FHMPFSKGDPKPDJ-UHFFFAOYSA-N 2,3,6-trimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1C FHMPFSKGDPKPDJ-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 240000008067 Cucumis sativus Species 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
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 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 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003641 microbiacidal effect Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 244000045561 useful plants Species 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- 241000235349 Ascomycota Species 0.000 description 1
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- 241000221198 Basidiomycota Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000219112 Cucumis Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
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- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241001480059 Erysiphaceae Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
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- 241001281802 Pseudoperonospora Species 0.000 description 1
- 241000221535 Pucciniales Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000005339 levitation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
- 229940124561 microbicide Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 230000026267 regulation of growth Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000009885 systemic effect Effects 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
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D213/60—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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (75)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AR258203A AR205189A1 (es) | 1974-04-02 | 1975-01-01 | Derivados de n-(1"-metoxi-carboniletil)-n-(furan-(2") carbonil) 2-6-dimetilanilina utiles como agentes microbicidas menos para usos farmaceuticos y procedimiento para su obtencion |
CH159175A CH603041A5 (en) | 1974-04-02 | 1975-02-10 | N-Furoyl-N-aryl-alanine esters |
CH1506177A CH606029A5 (en) | 1974-04-02 | 1975-02-10 | N-Furoyl-N-aryl-alanine esters |
FR7509484A FR2265747B1 (it) | 1974-04-02 | 1975-03-26 | |
FR7509485A FR2265748B1 (it) | 1974-04-02 | 1975-03-26 | |
DK135975AA DK141995B (da) | 1974-04-02 | 1975-03-26 | Fungicide, eventuelt halogensubstituerede furan(2)- eller tetrahydrofuran(2)-carboanilider til anvendelse ved plantebeskyttelse eller andre tekniske formål. |
DK135875AA DK141168B (da) | 1974-04-02 | 1975-03-26 | Fungicide anilidforbindelser til anvendelse ved plantebeskyttelse. |
FI750921A FI750921A (it) | 1974-04-02 | 1975-03-26 | |
SE7503518A SE418086B (sv) | 1974-04-02 | 1975-03-26 | Furan-2-respektive tetrahydrofuran-2-karboxylsyraanilider med fungicid verkan |
NO751084A NO141340C (no) | 1974-04-02 | 1975-03-26 | Anilider for anvendelse som mikrobicider |
SE7503517A SE419218B (sv) | 1974-04-02 | 1975-03-26 | Fungicida n-(substituerade-fenyl)-n-furanoyl-alanin-metylestrar |
FI750920A FI63567C (fi) | 1974-04-02 | 1975-03-26 | Substituerad furan-2-karbonsyra-anilid med fungicidisk verkan och dess anvaendning |
NO751086A NO142714C (no) | 1974-04-02 | 1975-03-26 | Anilider med fungicid virkning. |
AU79641/75A AU489499B2 (en) | 1975-03-27 | Microbiocidal and growth-regulating agents | |
CA223,222A CA1050558A (en) | 1974-04-02 | 1975-03-27 | N-(substituted phenyl)-n-furanoyl-alanine methyl esters and their use in fungicidal compositions and methods |
AU79640/75A AU465906B2 (en) | 1974-04-02 | 1975-03-27 | Microbicides |
DE2560591A DE2560591C2 (it) | 1974-04-02 | 1975-03-27 | |
NL7503755A NL7503755A (nl) | 1974-04-02 | 1975-03-27 | Werkwijze voor de bereiding van microbiocide en de groei regelende preparaten. |
NL7503754.A NL160821C (nl) | 1974-04-02 | 1975-03-27 | Werkwijze voor het bereiden van in de fenylgroep door alkylgroepen gesubstitueerde (n-alkoxycarbonylalkyl)- -n-acylanilinen, waarin de acylgroep is afgeleid van een cyclisch carbonzuur, alsmede werkwijze voor het bereiden van een microbicide preparaat dat deze verbindingen bevat. |
CA223,227A CA1050546A (en) | 1974-04-02 | 1975-03-27 | Derivatives of n-carboxy-alkyl anilides |
DE19752513732 DE2513732A1 (de) | 1974-04-02 | 1975-03-27 | Mikrobizide und wachstumsregulierende mittel |
DE19752513788 DE2513788C3 (de) | 1974-04-02 | 1975-03-27 | Substituierte Furan-2-carbonsäureanilide und Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende fungizide Mittel |
IT21855/75A IT1048806B (it) | 1974-04-02 | 1975-03-28 | Prodotti microbicidi e regolatori della crescita |
IT21867/75A IT1049394B (it) | 1974-04-02 | 1975-03-28 | Prodotto microbicida |
OA55460A OA04918A (fr) | 1974-04-02 | 1975-03-31 | Microbicides et agents régulateurs de croissance. |
OA55458A OA04916A (fr) | 1974-04-02 | 1975-03-31 | Nouveaux anilides, leur procédé de préparation et agents microbicides les contenant. |
PH16995A PH11792A (en) | 1974-04-02 | 1975-03-31 | Microbicidal and growth regulating agents |
PH16998A PH13072A (en) | 1974-04-02 | 1975-03-31 | Microbicides |
ES436175A ES436175A1 (es) | 1974-04-02 | 1975-04-01 | Procedimiento para la preparacion de derivados de anilida. |
GB13349/75A GB1498199A (en) | 1974-04-02 | 1975-04-01 | Fungicidal agents |
LU72174A LU72174A1 (it) | 1974-04-02 | 1975-04-01 | |
GB1333275A GB1448810A (en) | 1974-04-02 | 1975-04-01 | Fungicidal n-substituted furoic amide derivatives |
AR258204A AR224602A1 (es) | 1974-04-02 | 1975-04-01 | Composiciones en base a derivados de n-(carbonilo substituido)-2(substituido)-anilina y procedimiento para la obtencion de dichos derivados utiles en dichas composiciones |
AT244875A AT343407B (de) | 1974-04-02 | 1975-04-01 | Fungizide mittel |
IL46988A IL46988A (en) | 1974-04-02 | 1975-04-01 | N-(1'-methoxycarbonylethyl)-n-furan-2-ylcarbonyl aniline derivatives their manufacture and microbicidal and fungicidal compositions containing them |
LU72175A LU72175A1 (it) | 1974-04-02 | 1975-04-01 | |
RO7581867A RO73181A (ro) | 1974-04-02 | 1975-04-01 | Procedeu de preparare a derivatilor n-disubstituiti ai anilinei |
YU827/75A YU40259B (en) | 1974-04-02 | 1975-04-01 | Process for preparing new n-phenyl-n-acyl-alanine-or glycine ester |
IL46989A IL46989A (en) | 1974-04-02 | 1975-04-01 | Heteroacylanilides,their manufacture and micrtobiocidal and fungicidal compositions containing them |
SI7510828A SI7510828A8 (sl) | 1974-04-02 | 1975-04-01 | Postopek za pripravo substituiranih 2,6-dimetil-anilidov furan-2-karboksilne kisline |
HU75CI1564A HU173317B (hu) | 1974-04-02 | 1975-04-01 | Sposob poluchenija anilidov furankarbonovojj kisloty i mikrobicidnye kompozicii soderzhahhie ikh aktivnymi agentami |
DD185147A DD118785A5 (it) | 1974-04-02 | 1975-04-01 | |
ES436174A ES436174A1 (es) | 1974-04-02 | 1975-04-01 | Procedimiento para la preparacion de agentes microbicidas. |
DD192060A DD124733A5 (it) | 1974-04-02 | 1975-04-01 | |
YU00828/75A YU39026B (en) | 1974-04-02 | 1975-04-01 | Process for preparing substituted 2,6-dimethylanilides of furan-2-carboxylic acid |
DD185144A DD118510A5 (it) | 1974-04-02 | 1975-04-01 | |
HU75CI00001563A HU172935B (hu) | 1974-04-02 | 1975-04-01 | Sposob poluchenija furankarbonil-anilidov i mikrobicidnye sredstva i sredstva regulirujuhhie rost rastenij soderzhahhie takie soedinenija |
BG029508A BG26356A3 (bg) | 1974-04-02 | 1975-04-01 | Микробицидно средство |
AT244675A AT345614B (de) | 1974-04-02 | 1975-04-01 | Fungizide mittel |
BG029507A BG24651A3 (en) | 1974-04-02 | 1975-04-01 | Microbicide |
RO7581876A RO79677A (ro) | 1974-04-02 | 1975-04-02 | Compozitie fungicida |
IE709/75A IE41777B1 (en) | 1974-04-02 | 1975-04-02 | Fungicidal agents |
TR18339A TR18339A (tr) | 1974-04-02 | 1975-04-02 | Pestisidler |
PL1975179266A PL97786B1 (pl) | 1974-04-02 | 1975-04-02 | Srodek szkodnikobojczy i regulujacy wzrost roslin |
CS7500002239A CS183788B2 (en) | 1974-04-02 | 1975-04-02 | Fungicidal agent and mode of preparation of active substance |
RO106426A RO84021B (ro) | 1974-04-02 | 1975-04-02 | Procedeu pentru prepararea esterilor metilici ai unor n-fenil-furanoilanilide |
JP4022675A JPS5345364B2 (it) | 1974-04-02 | 1975-04-02 | |
EG194/75A EG11640A (en) | 1974-04-02 | 1975-04-02 | Microbiocidal and growth regulating agents |
IE708/75A IE41140B1 (en) | 1974-04-02 | 1975-04-02 | Fungicidal n-substituted furoic amide derivatives |
EG75195A EG12263A (en) | 1974-04-02 | 1975-04-02 | New active anilides for prevention microbs in cultivated cropes |
CS7500002240A CS183789B2 (en) | 1974-04-02 | 1975-04-02 | Fungicidal agent and mode of preparation of active substance |
TR18508A TR18508A (tr) | 1974-04-02 | 1975-04-02 | Pestsidler |
PL1975179265A PL98627B1 (pl) | 1974-04-02 | 1975-04-02 | Srodek szkodnikobojczy |
SU752120455A SU682096A3 (ru) | 1974-04-02 | 1975-04-02 | Микробицидное средство |
JP50040227A JPS6042202B2 (ja) | 1974-04-02 | 1975-04-02 | 植物真菌防除剤及びその製法 |
SU752121601A SU743561A3 (ru) | 1974-04-02 | 1975-04-02 | Микробицидное и регулирующее рост растений средство |
SU752186207A SU628812A3 (ru) | 1974-04-02 | 1975-11-05 | Способ получени органических содинений |
SU762342705A SU626690A3 (ru) | 1974-04-02 | 1976-04-05 | Способ получени органических соединений |
US05/703,037 US4046911A (en) | 1974-04-02 | 1976-07-06 | N-(substituted phenyl)-n-furanoyl-alanine methyl esters and their use in fungicidal composition and methods |
US05/709,066 US4094990A (en) | 1974-04-02 | 1976-07-27 | Certain phytofungicidal n-furanyl carbonyl and tetrahydrofuranyl carbonyl, n-(substituted)phenyl alanines |
AT765677A AT358025B (de) | 1974-04-02 | 1977-10-27 | Verfahren zur herstellung von neuen aniliden |
AT789377A AT355561B (de) | 1974-04-02 | 1977-11-04 | Verfahren zur herstellung von neuen substi- tuierten furan-2-carbonsaeureaniliden |
JP232778A JPS53135964A (en) | 1974-04-02 | 1978-01-12 | Process for preparing flancarboxylic anilide derivative |
JP53002328A JPS5845433B2 (ja) | 1975-02-10 | 1978-01-12 | 2↓−フランカルボン酸アニリド類の製造法 |
HRP-828/75A HRP940089B1 (en) | 1974-04-02 | 1994-02-11 | Process for the preparation of substituted 2,6-dimethyl-anylide-furan-2-carboxylic acid |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH457274A CH590608A5 (en) | 1974-04-02 | 1974-04-02 | N-Furoyl-N-aryl-alanine esters - prepd. e.g. by reacting N-aryl-alanine esters with 2-furoic acid or its derivs. |
CH159175A CH603041A5 (en) | 1974-04-02 | 1975-02-10 | N-Furoyl-N-aryl-alanine esters |
Publications (1)
Publication Number | Publication Date |
---|---|
CH603041A5 true CH603041A5 (en) | 1978-08-15 |
Family
ID=25688094
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH159175A CH603041A5 (en) | 1974-04-02 | 1975-02-10 | N-Furoyl-N-aryl-alanine esters |
Country Status (31)
Country | Link |
---|---|
JP (3) | JPS5345364B2 (it) |
AR (2) | AR205189A1 (it) |
AT (2) | AT343407B (it) |
AU (1) | AU465906B2 (it) |
BG (2) | BG26356A3 (it) |
CA (2) | CA1050558A (it) |
CH (1) | CH603041A5 (it) |
CS (2) | CS183788B2 (it) |
DD (3) | DD118785A5 (it) |
DE (2) | DE2513732A1 (it) |
DK (2) | DK141995B (it) |
EG (2) | EG11640A (it) |
ES (2) | ES436174A1 (it) |
FI (2) | FI750921A (it) |
FR (2) | FR2265747B1 (it) |
GB (2) | GB1448810A (it) |
HU (2) | HU173317B (it) |
IE (2) | IE41140B1 (it) |
IL (2) | IL46989A (it) |
IT (2) | IT1048806B (it) |
LU (2) | LU72174A1 (it) |
NL (2) | NL7503755A (it) |
NO (2) | NO141340C (it) |
OA (2) | OA04916A (it) |
PH (2) | PH13072A (it) |
PL (2) | PL98627B1 (it) |
RO (3) | RO73181A (it) |
SE (2) | SE419218B (it) |
SU (4) | SU682096A3 (it) |
TR (2) | TR18508A (it) |
YU (2) | YU39026B (it) |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5845433B2 (ja) * | 1975-02-10 | 1983-10-08 | チバ・ガイギ− アクチエンゲゼルシヤフト | 2↓−フランカルボン酸アニリド類の製造法 |
US4147792A (en) * | 1977-02-04 | 1979-04-03 | Ciba-Geigy Corporation | Fungicidal compositions |
CH629939A5 (de) * | 1977-03-29 | 1982-05-28 | Ciba Geigy Ag | Mikrobizides mittel. |
DE2724785A1 (de) * | 1977-05-27 | 1978-12-14 | Schering Ag | Furancarbonsaeureanilide, fungizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
BG28977A3 (en) * | 1978-02-02 | 1980-08-15 | Montedison Spa | Fungicide means and method for fungus fighting |
CH637368A5 (de) * | 1978-10-27 | 1983-07-29 | Ciba Geigy Ag | Anilinderivate und daraus hergestellte schaedlingsbekaempfungsmittel. |
EP0010673B1 (de) * | 1978-10-31 | 1982-01-27 | Bayer Ag | Substituierte N-Propargyl-aniline, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
CH641760A5 (de) * | 1978-11-27 | 1984-03-15 | Ciba Geigy Ag | Schaedlingsbekaempfungsmittel. |
CH639940A5 (en) * | 1978-12-05 | 1983-12-15 | Ciba Geigy Ag | Substituted N-alkoxycarbonylethyl-N-acylanilines, microbicides containing them, and process for the preparation of the compounds |
IT7927866A0 (it) * | 1978-12-07 | 1979-12-04 | Ciba Geigy Ag | Prodotti disinfestanti. |
DE2940189A1 (de) | 1979-10-04 | 1981-04-16 | Basf Ag, 6700 Ludwigshafen | Isoxazolylcarbonsaeureanilide, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
MA19111A1 (fr) * | 1979-10-26 | 1981-12-31 | Ciba Geigy Ag | Derives de l'homoserine,procede pour leur preparation et leur utilisation en tant que microbicides |
DE3013908A1 (de) * | 1980-04-11 | 1981-10-22 | Basf Ag, 6700 Ludwigshafen | 2-(n-aryl-, n-isoxazolylcarbonyl)-aminobutyrolactone, verfahren zu ihrer herstellung und diese enthaltende fungizide |
MA19215A1 (fr) * | 1980-07-25 | 1982-04-01 | Ciba Geigy Ag | Nouveaux derives arylamines,procede pour leur fabrication et utilisation en tant que microbicides . |
DE3030736A1 (de) | 1980-08-14 | 1982-03-25 | Basf Ag, 6700 Ludwigshafen | N-disubstituierte anilinderivate, ihre herstellung, ihre verwendung als mikrobizide und mittel dafuer |
DE3274859D1 (en) * | 1981-03-19 | 1987-02-05 | Ici Plc | Amide derivatives, processes for preparing them, their use as fungicides and pesticidal compositions containing them |
DE3133418A1 (de) * | 1981-08-24 | 1983-03-10 | Basf Ag, 6700 Ludwigshafen | Thiazolyl- und isothiazolylcarbonsaeureanilide, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
JPH0326906U (it) * | 1989-07-26 | 1991-03-19 | ||
DE4011172A1 (de) * | 1990-04-06 | 1991-10-10 | Degussa | Verbindungen zur bekaempfung von pflanzenkrankheiten |
DE4304172A1 (de) | 1993-02-12 | 1994-08-25 | Bayer Ag | Fungizide Wirkstoffkombinationen |
US5723491A (en) * | 1994-07-11 | 1998-03-03 | Novartis Corporation | Fungicidal composition and method of controlling fungus infestation |
DE4429014A1 (de) | 1994-08-16 | 1996-02-22 | Basf Ag | Verfahren zur Herstellung von cyclischen Aminen |
AR011515A1 (es) * | 1996-12-25 | 2000-08-30 | Agrogene Ltd | Derivado del acido aminobutirico para la proteccion de plantas de enfermedades fungosas y un metodo para proteger un cultivo contra enfermedadesfungosas por ejemplo tomates y papas contra el tizon tardio o temprano, cereales contra el mildiu polvoroso, y pepino, vides, melones contra el mildiu |
DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
DE102004049761A1 (de) | 2004-10-12 | 2006-04-13 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
US8754009B2 (en) | 2005-06-09 | 2014-06-17 | Bayer Cropscience Ag | Active compound combinations |
DE102006023263A1 (de) | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
EP2489263A3 (en) | 2006-09-18 | 2012-10-24 | Basf Se | Pesticidal mixtures comprising an anthranilamide insecticide and a fungicide |
MX2009007603A (es) | 2007-02-06 | 2009-07-24 | Basf Se | Insecticidas como safeners ara fungicidas con accion fitotoxica. |
EP2000030A1 (de) | 2007-06-06 | 2008-12-10 | Bayer CropScience AG | Fungizide Wirkstoffkombinationen |
EP2000028A1 (de) | 2007-06-06 | 2008-12-10 | Bayer CropScience Aktiengesellschaft | Fungizide Wirkstoffkombinationen |
DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
EP2453750A2 (de) | 2009-07-16 | 2012-05-23 | Bayer CropScience AG | Synergistische wirkstoffkombinationen mit phenyltriazolen |
EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
CN115557887B (zh) * | 2022-11-10 | 2024-11-01 | 南京林业大学 | 基于Ugi反应的三氟甲基吡啶衍生物合成及其生物活性研究 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US3959481A (en) * | 1969-02-13 | 1976-05-25 | Uniroyal | Method of protecting plants from fungal diseases using furan-3-carboxamide derivatives |
JPS5345364A (en) * | 1976-10-06 | 1978-04-24 | Daiahoiru Kk | Device for controlling extrusion molding die bolt |
-
1975
- 1975-01-01 AR AR258203A patent/AR205189A1/es active
- 1975-02-10 CH CH159175A patent/CH603041A5/de not_active IP Right Cessation
- 1975-03-26 DK DK135975AA patent/DK141995B/da not_active IP Right Cessation
- 1975-03-26 FR FR7509484A patent/FR2265747B1/fr not_active Expired
- 1975-03-26 NO NO751084A patent/NO141340C/no unknown
- 1975-03-26 DK DK135875AA patent/DK141168B/da not_active IP Right Cessation
- 1975-03-26 SE SE7503517A patent/SE419218B/xx not_active IP Right Cessation
- 1975-03-26 FR FR7509485A patent/FR2265748B1/fr not_active Expired
- 1975-03-26 FI FI750921A patent/FI750921A/fi not_active Application Discontinuation
- 1975-03-26 SE SE7503518A patent/SE418086B/xx not_active IP Right Cessation
- 1975-03-26 FI FI750920A patent/FI63567C/fi not_active IP Right Cessation
- 1975-03-26 NO NO751086A patent/NO142714C/no unknown
- 1975-03-27 NL NL7503755A patent/NL7503755A/xx not_active Application Discontinuation
- 1975-03-27 AU AU79640/75A patent/AU465906B2/en not_active Expired
- 1975-03-27 CA CA223,222A patent/CA1050558A/en not_active Expired
- 1975-03-27 DE DE19752513732 patent/DE2513732A1/de active Granted
- 1975-03-27 CA CA223,227A patent/CA1050546A/en not_active Expired
- 1975-03-27 NL NL7503754.A patent/NL160821C/xx not_active IP Right Cessation
- 1975-03-27 DE DE2560591A patent/DE2560591C2/de not_active Expired
- 1975-03-28 IT IT21855/75A patent/IT1048806B/it active
- 1975-03-28 IT IT21867/75A patent/IT1049394B/it active
- 1975-03-31 OA OA55458A patent/OA04916A/xx unknown
- 1975-03-31 PH PH16998A patent/PH13072A/en unknown
- 1975-03-31 PH PH16995A patent/PH11792A/en unknown
- 1975-03-31 OA OA55460A patent/OA04918A/xx unknown
- 1975-04-01 LU LU72174A patent/LU72174A1/xx unknown
- 1975-04-01 RO RO7581867A patent/RO73181A/ro unknown
- 1975-04-01 GB GB1333275A patent/GB1448810A/en not_active Expired
- 1975-04-01 DD DD185147A patent/DD118785A5/xx unknown
- 1975-04-01 ES ES436174A patent/ES436174A1/es not_active Expired
- 1975-04-01 BG BG029508A patent/BG26356A3/xx unknown
- 1975-04-01 HU HU75CI1564A patent/HU173317B/hu unknown
- 1975-04-01 LU LU72175A patent/LU72175A1/xx unknown
- 1975-04-01 AT AT244875A patent/AT343407B/de not_active IP Right Cessation
- 1975-04-01 YU YU00828/75A patent/YU39026B/xx unknown
- 1975-04-01 ES ES436175A patent/ES436175A1/es not_active Expired
- 1975-04-01 AT AT244675A patent/AT345614B/de not_active IP Right Cessation
- 1975-04-01 IL IL46989A patent/IL46989A/xx unknown
- 1975-04-01 DD DD185144A patent/DD118510A5/xx unknown
- 1975-04-01 BG BG029507A patent/BG24651A3/xx unknown
- 1975-04-01 IL IL46988A patent/IL46988A/en unknown
- 1975-04-01 GB GB13349/75A patent/GB1498199A/en not_active Expired
- 1975-04-01 AR AR258204A patent/AR224602A1/es active
- 1975-04-01 HU HU75CI00001563A patent/HU172935B/hu not_active IP Right Cessation
- 1975-04-01 DD DD192060A patent/DD124733A5/xx unknown
- 1975-04-01 YU YU827/75A patent/YU40259B/xx unknown
- 1975-04-02 RO RO7581876A patent/RO79677A/ro unknown
- 1975-04-02 IE IE708/75A patent/IE41140B1/xx unknown
- 1975-04-02 JP JP4022675A patent/JPS5345364B2/ja not_active Expired
- 1975-04-02 EG EG194/75A patent/EG11640A/xx active
- 1975-04-02 PL PL1975179265A patent/PL98627B1/pl unknown
- 1975-04-02 TR TR18508A patent/TR18508A/xx unknown
- 1975-04-02 RO RO106426A patent/RO84021B/ro unknown
- 1975-04-02 TR TR18339A patent/TR18339A/xx unknown
- 1975-04-02 PL PL1975179266A patent/PL97786B1/pl unknown
- 1975-04-02 IE IE709/75A patent/IE41777B1/en unknown
- 1975-04-02 SU SU752120455A patent/SU682096A3/ru active
- 1975-04-02 EG EG75195A patent/EG12263A/xx active
- 1975-04-02 JP JP50040227A patent/JPS6042202B2/ja not_active Expired
- 1975-04-02 CS CS7500002239A patent/CS183788B2/cs unknown
- 1975-04-02 CS CS7500002240A patent/CS183789B2/cs unknown
- 1975-04-02 SU SU752121601A patent/SU743561A3/ru active
- 1975-11-05 SU SU752186207A patent/SU628812A3/ru active
-
1976
- 1976-04-05 SU SU762342705A patent/SU626690A3/ru active
-
1978
- 1978-01-12 JP JP232778A patent/JPS53135964A/ja active Granted
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