JPS61286363A - Ｎα−（２−シア１−２−アルコキシイミノアセチル）−アミノ酸誘導体およびペプチドのＥ−異性体 - Google Patents

Ｎα−（２−シア１−２−アルコキシイミノアセチル）−アミノ酸誘導体およびペプチドのＥ−異性体

Info

Publication number: JPS61286363A
Authority: JP; Japan
Prior art keywords: alkyl; carbon atoms; phenyl; formula; substituents
Prior art date: 1985-06-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP61135091A

Other languages

English (en)

Japanese (ja)

Inventor

ビンフリート・ルンケンハイマー

ハンス・シヤインプフルーク

ビルヘルム・ブランデス

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-06-13

Filing date

1986-06-12

Publication date

1986-12-16

1986-06-12 Application filed by Bayer AG filed Critical Bayer AG

1986-12-16 Publication of JPS61286363A publication Critical patent/JPS61286363A/ja

Status Pending legal-status Critical Current

Links

108090000765 processed proteins & peptides Proteins 0.000 title claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 142
125000000217 alkyl group Chemical group 0.000 claims description 133
125000001424 substituent group Chemical group 0.000 claims description 84
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
-1 azolylalkyl Chemical group 0.000 claims description 66
239000001257 hydrogen Substances 0.000 claims description 49
229910052739 hydrogen Inorganic materials 0.000 claims description 49
238000000034 method Methods 0.000 claims description 38
125000003884 phenylalkyl group Chemical group 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 25
125000003342 alkenyl group Chemical group 0.000 claims description 24
125000000304 alkynyl group Chemical group 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
239000000126 substance Substances 0.000 claims description 21
125000004966 cyanoalkyl group Chemical group 0.000 claims description 20
150000001412 amines Chemical class 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 16
229910052799 carbon Chemical group 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 15
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
229910052751 metal Chemical class 0.000 claims description 14
239000002184 metal Chemical class 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 13
239000011737 fluorine Substances 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 13
102000004196 processed proteins & peptides Human genes 0.000 claims description 13
150000003862 amino acid derivatives Chemical class 0.000 claims description 12
125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 11
150000001340 alkali metals Chemical class 0.000 claims description 10
239000003085 diluting agent Substances 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
229910052783 alkali metal Inorganic materials 0.000 claims description 9
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
125000002947 alkylene group Chemical group 0.000 claims description 7
150000003863 ammonium salts Chemical class 0.000 claims description 7
239000011230 binding agent Substances 0.000 claims description 7
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 7
125000001188 haloalkyl group Chemical group 0.000 claims description 7
241000607479 Yersinia pestis Species 0.000 claims description 6
125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 6
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
150000001413 amino acids Chemical class 0.000 claims description 5
150000001735 carboxylic acids Chemical class 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
150000002527 isonitriles Chemical class 0.000 claims description 5
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
125000004442 acylamino group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
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 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
241000233866 Fungi Species 0.000 claims description 3
150000001342 alkaline earth metals Chemical group 0.000 claims description 3
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
125000006598 aminocarbonylamino group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
238000006467 substitution reaction Methods 0.000 claims description 3
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 2
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 2
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 15
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
241000255925 Diptera Species 0.000 claims 2
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
239000000945 filler Substances 0.000 claims 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 47
125000004435 hydrogen atom Chemical group [H]* 0.000 description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
241000894007 species Species 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000009472 formulation Methods 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 12
241000196324 Embryophyta Species 0.000 description 10
239000007858 starting material Substances 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000003995 emulsifying agent Substances 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
LWZMFXQOIDFKQJ-UHFFFAOYSA-N 2-cyano-2-methoxyiminoacetic acid Chemical compound CON=C(C#N)C(O)=O LWZMFXQOIDFKQJ-UHFFFAOYSA-N 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
241000233622 Phytophthora infestans Species 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
229940024606 amino acid Drugs 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 5
239000000417 fungicide Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
239000002689 soil Substances 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
241000227653 Lycopersicon Species 0.000 description 4
235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
230000002538 fungal effect Effects 0.000 description 4
230000000855 fungicidal effect Effects 0.000 description 4
239000007789 gas Substances 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
239000011701 zinc Substances 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
239000004606 Fillers/Extenders Substances 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
241000233614 Phytophthora Species 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000000969 carrier Substances 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
239000004020 conductor Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
239000000975 dye Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
MZGFKQBLSUREHL-UHFFFAOYSA-N ethyl 2-cyano-2-methoxyiminoacetate Chemical compound CCOC(=O)C(C#N)=NOC MZGFKQBLSUREHL-UHFFFAOYSA-N 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
238000003958 fumigation Methods 0.000 description 3
238000011081 inoculation Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
230000001681 protective effect Effects 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Chemical group 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
VZAWCLCJGSBATP-UHFFFAOYSA-N 1-cycloundecyl-1,2-diazacycloundecane Chemical compound C1CCCCCCCCCC1N1NCCCCCCCCC1 VZAWCLCJGSBATP-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
241001157813 Cercospora Species 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
208000031888 Mycoses Diseases 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
241001281802 Pseudoperonospora Species 0.000 description 2
241000228453 Pyrenophora Species 0.000 description 2
241000233639 Pythium Species 0.000 description 2
241001533598 Septoria Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000221576 Uromyces Species 0.000 description 2
241000219094 Vitaceae Species 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
229960004424 carbon dioxide Drugs 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
150000001733 carboxylic acid esters Chemical class 0.000 description 2
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239000011135 tin Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrrole Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP61135091A 1985-06-13 1986-06-12 Ｎα−（２−シア１−２−アルコキシイミノアセチル）−アミノ酸誘導体およびペプチドのＥ−異性体 Pending JPS61286363A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE3521131		1985-06-13
DE3521131.8		1985-06-13
DE3602243.8		1986-01-25

Publications (1)

Publication Number	Publication Date
JPS61286363A true JPS61286363A (ja)	1986-12-16

Family

ID=6273120

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61135091A Pending JPS61286363A (ja)	1985-06-13	1986-06-12	Ｎα−（２−シア１−２−アルコキシイミノアセチル）−アミノ酸誘導体およびペプチドのＥ−異性体

Country Status (3)

Country	Link
JP (1)	JPS61286363A (de)
DD (1)	DD247370A5 (de)
ZA (1)	ZA864443B (de)

1986
- 1986-06-11 DD DD29120986A patent/DD247370A5/de not_active IP Right Cessation
- 1986-06-12 JP JP61135091A patent/JPS61286363A/ja active Pending
- 1986-06-13 ZA ZA864443A patent/ZA864443B/xx unknown

Also Published As

Publication number	Publication date
ZA864443B (en)	1987-02-25
DD247370A5 (de)	1987-07-08

Publication	Publication Date	Title
JPH0768200B2 (ja)	1995-07-26	置換バリンアミド誘導体
EP0206004B1 (de)	1993-04-28	E-Isomere von N alpha-(2-Cyan-2-alkoximino-acetyl)-amino-säurederivaten und -peptiden
EP0313091B1 (de)	1993-09-01	Amid-Derivate, Verfahren zu deren Herstellung sowie diese enthaltende Fungizide in der Agrikultur und im Gartenbau
KR0185970B1 (ko)	1999-05-15	치환된 아미노산 아미드 유도체, 이의 제조방법 및 이의 용도
CA1141386A (en)	1983-02-15	Herbicides
JPS6335555A (ja)	1988-02-16	Ｎ↑ａ−（２−シアノ−２−アルコキシイミノアセチル）−アミノ酸誘導体及び−ペプチド類
JPS60233062A (ja)	1985-11-19	Ｎ‐（アゾリルカルバモイル）‐ヒドロキシルアミン及び該化合物を含有する殺菌剤
US5026710A (en)	1991-06-25	(2-cyano-2-oximinoacetyl)-amino acid derivatives
JPS6335554A (ja)	1988-02-16	Ｎ−（２−シアノ−２−オキシミノアセチル）−アミノニトリル
JPS61286363A (ja)	1986-12-16	Ｎα−（２−シア１−２−アルコキシイミノアセチル）−アミノ酸誘導体およびペプチドのＥ−異性体
KR890003834B1 (ko)	1989-10-05	치환된 말레이미드의 제조방법
EP0294668B1 (de)	1993-04-07	(2-Cyan-2-oximinoacetyl)-aminosäure-Derivate
JPS62201858A (ja)	1987-09-05	Ｎα−（２−シアノ−２−アルコキシイミノアセチル）−アミノ酸誘導体およびペプチドのＥ−異性体
EP0221502A1 (de)	1987-05-13	Substituierte 1-Amino-cyclopropancarbonsäurederivate
JPH01160956A (ja)	1989-06-23	Ｎ−置換ジクロロマレイミド類
US5189061A (en)	1993-02-23	(2-cyano-2-oximinoacetyl)-amino acid derivatives
JP2723155B2 (ja)	1998-03-09	農園芸用殺菌剤組成物
DD298778A5 (de)	1992-03-12	Cyclopropanoylaminosaeureamid-derivate
JPS63156760A (ja)	1988-06-29	置換ベンズアミド
US4362877A (en)	1982-12-07	2,4-Disubstituted-1,2,5-thiadiazol-3(2H)-one antimicrobials
JPH013161A (ja)	1989-01-06	（２−シアノ−２−オキシイミノアセチル）−アミノ酸誘導体
JPH06271535A (ja)	1994-09-27	Ｎ−置換α−フルオロアルキル−ラクタム類
JPH013160A (ja)	1989-01-06	（２−シアノ−２−オキシイミノアセチル）−アミノ酸誘導体
JPS63150268A (ja)	1988-06-22	置換アミンのサツカリン塩
JPH09291077A (ja)	1997-11-11	ベンジルシアナイド誘導体およびその誘導体を含有する農園芸用殺菌剤