CS259863B2 - Fungicide and method of its efficient substance production - Google Patents
Fungicide and method of its efficient substance production Download PDFInfo
- Publication number
- CS259863B2 CS259863B2 CS836982A CS698283A CS259863B2 CS 259863 B2 CS259863 B2 CS 259863B2 CS 836982 A CS836982 A CS 836982A CS 698283 A CS698283 A CS 698283A CS 259863 B2 CS259863 B2 CS 259863B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- compound
- formula
- pyridyl
- optionally substituted
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 19
- 239000000126 substance Substances 0.000 title claims description 3
- 239000000417 fungicide Substances 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 239000004480 active ingredient Substances 0.000 claims abstract description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- -1 ethylene sorbitan ester Chemical class 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 239000007921 spray Substances 0.000 claims description 8
- 230000001629 suppression Effects 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000005507 spraying Methods 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 238000011081 inoculation Methods 0.000 claims description 4
- 241001480061 Blumeria graminis Species 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000011572 manganese Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229920001213 Polysorbate 20 Polymers 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 230000001256 tonic effect Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 18
- 150000002148 esters Chemical class 0.000 abstract description 7
- 229910052751 metal Chemical class 0.000 abstract description 6
- 239000002184 metal Chemical class 0.000 abstract description 6
- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 5
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- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
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- 241000196324 Embryophyta Species 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 12
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
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- 239000011734 sodium Substances 0.000 description 5
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- 229910052708 sodium Inorganic materials 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- YXZASALEKGXIAA-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-3-pyridin-3-ylprop-2-enoic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C(=O)O)=CC1=CC=CN=C1 YXZASALEKGXIAA-UHFFFAOYSA-N 0.000 description 3
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
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- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
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- 230000008020 evaporation Effects 0.000 description 3
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
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- 239000000463 material Substances 0.000 description 3
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- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- XEKAUTDWPYQNFU-UHFFFAOYSA-N chlorane Chemical compound Cl.Cl.Cl XEKAUTDWPYQNFU-UHFFFAOYSA-N 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 210000000349 chromosome Anatomy 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ZURAKLKIKYCUJU-UHFFFAOYSA-N copper;azane Chemical compound N.[Cu+2] ZURAKLKIKYCUJU-UHFFFAOYSA-N 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- PHQKZMYRTMPOBK-UHFFFAOYSA-N cyclohexanone;4-methylpentan-2-one Chemical compound CC(C)CC(C)=O.O=C1CCCCC1 PHQKZMYRTMPOBK-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
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- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
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- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 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
- 239000000025 natural resin Substances 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000004525 petroleum distillation Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- WOIOUPCWKZMWJN-UHFFFAOYSA-N prop-2-enoyl chloride hydrochloride Chemical compound Cl.ClC(=O)C=C WOIOUPCWKZMWJN-UHFFFAOYSA-N 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 231100000009 visible necrosis Toxicity 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8227480 | 1982-09-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
CS698283A2 CS698283A2 (en) | 1988-04-15 |
CS259863B2 true CS259863B2 (en) | 1988-11-15 |
Family
ID=10533178
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS836982A CS259863B2 (en) | 1982-09-27 | 1983-09-26 | Fungicide and method of its efficient substance production |
Country Status (18)
Country | Link |
---|---|
US (1) | US4600712A (es) |
EP (1) | EP0104690A3 (es) |
JP (1) | JPS5978162A (es) |
AU (1) | AU571458B2 (es) |
BR (1) | BR8305265A (es) |
CA (1) | CA1234388A (es) |
CS (1) | CS259863B2 (es) |
DD (1) | DD213348A5 (es) |
DK (1) | DK163703C (es) |
ES (1) | ES525941A0 (es) |
FI (1) | FI79930C (es) |
GR (1) | GR79416B (es) |
HU (1) | HU194481B (es) |
NO (1) | NO165221C (es) |
NZ (1) | NZ205738A (es) |
PL (1) | PL136537B1 (es) |
PT (1) | PT77394B (es) |
ZA (1) | ZA837141B (es) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3421179A1 (de) * | 1984-06-07 | 1985-12-12 | Basf Ag, 6700 Ludwigshafen | Azolylnitrile und diese enthaltende fungizide |
EP0243012B1 (en) * | 1986-04-17 | 1993-01-13 | Imperial Chemical Industries Plc | Pyridyl-acrylic acid ester derivatives, process for their preparation and their use as fungicides |
US5221316A (en) * | 1986-04-17 | 1993-06-22 | Imperial Chemical Industries Plc | Fungicides |
US5036074A (en) * | 1989-03-01 | 1991-07-30 | Ciba-Geigy Corporation | Certain 2,4-dichloro-phenyl(loweralkylidene) pyridines having fungicidal activity |
DE4003919A1 (de) * | 1990-02-09 | 1991-08-14 | Basf Ag | Heteroarylalkene, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung |
US5196446A (en) * | 1990-04-16 | 1993-03-23 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Certain indole compounds which inhibit EGF receptor tyrosine kinase |
US5418245A (en) * | 1990-04-16 | 1995-05-23 | Rhone-Poulenc Rorer International (Holdings) Inc. | Styryl-substituted monocyclic and bicyclic heteroaryl compounds which inhibit EGF receptor tyrosine kinase |
US5302606A (en) * | 1990-04-16 | 1994-04-12 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Styryl-substituted pyridyl compounds which inhibit EGF receptor tyrosine kinase |
AU658567B2 (en) * | 1990-04-16 | 1995-04-27 | Rhone-Poulenc Rorer International (Holdings) Inc. | Styryl-substituted indole and pyridyl compounds |
US5656655A (en) * | 1994-03-17 | 1997-08-12 | Rhone-Poulenc Rorer Pharmaceuticals, Inc. | Styryl-substituted heteroaryl compounds which inhibit EGF receptor tyrosine kinase |
JP4883311B2 (ja) * | 1996-04-25 | 2012-02-22 | 日産化学工業株式会社 | エチレン誘導体および有害生物防除剤 |
CA2252536C (en) * | 1996-04-25 | 2010-04-06 | Nissan Chemical Industries, Ltd. | Ethylene derivatives and pesticides containing said derivatives |
TW513285B (en) | 1997-02-14 | 2002-12-11 | Ishihara Sangyo Kaisha | Acrylonitrile compounds, process and intermediates for their production, method for controlling pests comprising using them and pesticides, fungicides and marine antifouling agents containing them |
KR20010108050A (ko) | 1998-12-25 | 2001-12-07 | 도쿠시마 히데이치 | 아크릴로니트릴 화합물 |
WO2004072066A1 (en) * | 2003-02-11 | 2004-08-26 | Prosidion Limited | Tri(cyclo) substituted amide glucokinase activator compounds |
EP2267446A1 (de) | 2009-06-24 | 2010-12-29 | Roche Diagnostics GmbH | Spreitschicht und Verfahren zur Herstellung einer Analyseelement-Spreitschicht |
EP3498273A1 (en) * | 2017-12-14 | 2019-06-19 | Universität Wien | Pharmaceutical composition for modulating the response of a gaba-a receptor |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3196158A (en) * | 1961-07-26 | 1965-07-20 | Ciba Geigy Corp | 3-(ortho-chloro-phenyl)-2-(pyridyl)-acrylonitriles |
US3157663A (en) * | 1962-11-20 | 1964-11-17 | Ciba Geigy Corp | 3-(amino-phenyl)-2-(pyridyl)-acrylonitriles |
US3301863A (en) * | 1963-04-24 | 1967-01-31 | Schering Corp | Amino derivatives of phenethylpyridines |
US3370063A (en) * | 1964-10-05 | 1968-02-20 | Mcneilab Inc | Substituted dimethoxy indoles and method of making the same |
US3361863A (en) * | 1965-04-12 | 1968-01-02 | Karl A. Lang | Furnace |
US3337568A (en) * | 1965-06-24 | 1967-08-22 | Ciba Geigy Corp | Beta hydroxy heterocyclic aryl derivatives of acrylamide |
US3846553A (en) * | 1969-12-03 | 1974-11-05 | Merck & Co Inc | 3-substituted-2-pyridones in the treatment of pain, fever or inflammation |
US3928352A (en) * | 1974-05-07 | 1975-12-23 | Lilly Co Eli | Certain substituted 2-pyrazinemethanols |
US4428948A (en) * | 1977-02-03 | 1984-01-31 | Rohm And Haas Company | Novel heterocyclic compounds |
IE56045B1 (en) * | 1982-09-27 | 1991-03-27 | Shell Int Research | Fungicidally active compounds |
DK429884A (da) * | 1983-10-07 | 1985-04-08 | Hoffmann La Roche | Heterocycliske forbindelser |
-
1983
- 1983-08-22 CA CA000435095A patent/CA1234388A/en not_active Expired
- 1983-08-30 EP EP83201249A patent/EP0104690A3/en not_active Ceased
- 1983-09-26 AU AU19568/83A patent/AU571458B2/en not_active Ceased
- 1983-09-26 PT PT77394A patent/PT77394B/pt not_active IP Right Cessation
- 1983-09-26 CS CS836982A patent/CS259863B2/cs unknown
- 1983-09-26 GR GR72531A patent/GR79416B/el unknown
- 1983-09-26 DK DK440283A patent/DK163703C/da not_active IP Right Cessation
- 1983-09-26 ES ES525941A patent/ES525941A0/es active Granted
- 1983-09-26 BR BR8305265A patent/BR8305265A/pt not_active IP Right Cessation
- 1983-09-26 ZA ZA837141A patent/ZA837141B/xx unknown
- 1983-09-26 NO NO833450A patent/NO165221C/no unknown
- 1983-09-26 HU HU833333A patent/HU194481B/hu not_active IP Right Cessation
- 1983-09-26 DD DD83255115A patent/DD213348A5/de not_active IP Right Cessation
- 1983-09-26 JP JP58176543A patent/JPS5978162A/ja active Granted
- 1983-09-26 FI FI833456A patent/FI79930C/fi not_active IP Right Cessation
- 1983-09-26 NZ NZ205738A patent/NZ205738A/xx unknown
- 1983-09-26 PL PL1983243907A patent/PL136537B1/pl unknown
-
1985
- 1985-10-09 US US06/785,693 patent/US4600712A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP0104690A2 (en) | 1984-04-04 |
FI833456A (fi) | 1984-03-28 |
JPS5978162A (ja) | 1984-05-04 |
ES8504653A1 (es) | 1985-04-16 |
GR79416B (es) | 1984-10-22 |
US4600712A (en) | 1986-07-15 |
DK440283A (da) | 1984-03-28 |
NO165221B (no) | 1990-10-08 |
NZ205738A (en) | 1985-09-13 |
DK163703B (da) | 1992-03-30 |
HU194481B (en) | 1988-02-29 |
DK440283D0 (da) | 1983-09-26 |
FI833456A0 (fi) | 1983-09-26 |
FI79930C (fi) | 1990-04-10 |
PT77394B (en) | 1986-02-18 |
CA1234388A (en) | 1988-03-22 |
PT77394A (en) | 1983-10-01 |
BR8305265A (pt) | 1984-05-02 |
EP0104690A3 (en) | 1985-07-31 |
PL136537B1 (en) | 1986-02-28 |
JPH0446270B2 (es) | 1992-07-29 |
CS698283A2 (en) | 1988-04-15 |
DD213348A5 (de) | 1984-09-12 |
ES525941A0 (es) | 1985-04-16 |
AU1956883A (en) | 1984-04-05 |
FI79930B (fi) | 1989-12-29 |
DK163703C (da) | 1992-09-07 |
AU571458B2 (en) | 1988-04-21 |
PL243907A1 (en) | 1984-10-22 |
NO833450L (no) | 1984-03-28 |
ZA837141B (en) | 1984-05-30 |
NO165221C (no) | 1991-01-16 |
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