JPS5811855B2 - 新規な置換クロトンアニリドの製造法 - Google Patents
新規な置換クロトンアニリドの製造法Info
- Publication number
- JPS5811855B2 JPS5811855B2 JP48105100A JP10510073A JPS5811855B2 JP S5811855 B2 JPS5811855 B2 JP S5811855B2 JP 48105100 A JP48105100 A JP 48105100A JP 10510073 A JP10510073 A JP 10510073A JP S5811855 B2 JPS5811855 B2 JP S5811855B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- carbon atoms
- alkyl group
- group containing
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- BZSYYMAHNJHZCB-QHHAFSJGSA-N (e)-n-phenylbut-2-enamide Chemical class C\C=C\C(=O)NC1=CC=CC=C1 BZSYYMAHNJHZCB-QHHAFSJGSA-N 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000002168 alkylating agent Substances 0.000 claims description 9
- 229940100198 alkylating agent Drugs 0.000 claims description 9
- 150000003931 anilides Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 241001448862 Croton Species 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000011282 treatment Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000004364 calculation method Methods 0.000 description 9
- 230000002363 herbicidal effect Effects 0.000 description 9
- -1 3-(Methylthio)crotonanilide Chemical compound 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- HFIOZQGCNMQTKS-HJWRWDBZSA-N (z)-3-methoxy-n-phenylbut-2-enamide Chemical compound CO\C(C)=C/C(=O)NC1=CC=CC=C1 HFIOZQGCNMQTKS-HJWRWDBZSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000003828 vacuum filtration Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- KDPAUGYGDVPJLA-NTMALXAHSA-N (z)-3-methoxy-n-(3-methylphenyl)but-2-enamide Chemical compound CO\C(C)=C/C(=O)NC1=CC=CC(C)=C1 KDPAUGYGDVPJLA-NTMALXAHSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FOSFIXWZAJNJGQ-ALCCZGGFSA-N (z)-n-(3,4-dichlorophenyl)-3-methoxybut-2-enamide Chemical compound CO\C(C)=C/C(=O)NC1=CC=C(Cl)C(Cl)=C1 FOSFIXWZAJNJGQ-ALCCZGGFSA-N 0.000 description 3
- JOGAIDHEOAKDMN-UHFFFAOYSA-N 3,3-dimethoxy-n-phenylbutanamide Chemical compound COC(C)(OC)CC(=O)NC1=CC=CC=C1 JOGAIDHEOAKDMN-UHFFFAOYSA-N 0.000 description 3
- ZGCZHWUZVGIDCX-UHFFFAOYSA-N 3,3-dimethoxy-n-phenylhexanamide Chemical compound CCCC(OC)(OC)CC(=O)NC1=CC=CC=C1 ZGCZHWUZVGIDCX-UHFFFAOYSA-N 0.000 description 3
- VUSNAHINYXHHFZ-UHFFFAOYSA-N 3-oxo-n-phenylbutanethioamide Chemical compound CC(=O)CC(=S)NC1=CC=CC=C1 VUSNAHINYXHHFZ-UHFFFAOYSA-N 0.000 description 3
- 235000016068 Berberis vulgaris Nutrition 0.000 description 3
- 241000335053 Beta vulgaris Species 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HMNZRAXGYXHWLG-UHFFFAOYSA-N 3-methoxy-n-phenylhex-2-enamide Chemical compound CCCC(OC)=CC(=O)NC1=CC=CC=C1 HMNZRAXGYXHWLG-UHFFFAOYSA-N 0.000 description 2
- NMKOPQKZWILKQU-UHFFFAOYSA-N 3-oxo-n-phenylhexanamide Chemical compound CCCC(=O)CC(=O)NC1=CC=CC=C1 NMKOPQKZWILKQU-UHFFFAOYSA-N 0.000 description 2
- 241000743339 Agrostis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007516 Chrysanthemum Nutrition 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 2
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229960004029 silicic acid Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- QSBDRCYMAZSHPD-ARJAWSKDSA-N (Z)-3-methoxybut-2-enamide Chemical compound CO\C(=C/C(=O)N)\C QSBDRCYMAZSHPD-ARJAWSKDSA-N 0.000 description 1
- RXIQZLYUALLPSW-FLIBITNWSA-N (Z)-N-(2,6-dimethylphenyl)-3-methoxybut-2-enamide Chemical compound CO\C(=C/C(=O)NC1=C(C=CC=C1C)C)\C RXIQZLYUALLPSW-FLIBITNWSA-N 0.000 description 1
- QKSDDXIMJDYXSM-FPLPWBNLSA-N (Z)-N-(4-chlorophenyl)-3-methoxybut-2-enamide Chemical compound CO\C(=C/C(=O)NC1=CC=C(C=C1)Cl)\C QKSDDXIMJDYXSM-FPLPWBNLSA-N 0.000 description 1
- YEPMGMICLADAQX-IHWYPQMZSA-N (z)-3-chlorobut-2-enoyl chloride Chemical compound C\C(Cl)=C\C(Cl)=O YEPMGMICLADAQX-IHWYPQMZSA-N 0.000 description 1
- ALNLBVSCWBODNE-VURMDHGXSA-N (z)-3-methoxy-n-[3-(trifluoromethyl)phenyl]but-2-enamide Chemical compound CO\C(C)=C/C(=O)NC1=CC=CC(C(F)(F)F)=C1 ALNLBVSCWBODNE-VURMDHGXSA-N 0.000 description 1
- GICJFGGKRNLMBB-VURMDHGXSA-N (z)-n-(3,4-dichlorophenyl)-3-ethoxybut-2-enamide Chemical compound CCO\C(C)=C/C(=O)NC1=CC=C(Cl)C(Cl)=C1 GICJFGGKRNLMBB-VURMDHGXSA-N 0.000 description 1
- YOTPJLYOOXQHKX-UHFFFAOYSA-N 3-oxo-n-[3-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC(C(F)(F)F)=C1 YOTPJLYOOXQHKX-UHFFFAOYSA-N 0.000 description 1
- OJHDELQFIANLQR-UHFFFAOYSA-N 4,4-dichloro-3-oxo-n-phenylbutanamide Chemical compound ClC(Cl)C(=O)CC(=O)NC1=CC=CC=C1 OJHDELQFIANLQR-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- DTCJYIIKPVRVDD-UHFFFAOYSA-N Benzthiazuron Chemical compound C1=CC=C2SC(NC(=O)NC)=NC2=C1 DTCJYIIKPVRVDD-UHFFFAOYSA-N 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 241000723353 Chrysanthemum Species 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- MNYARIILPGRTQL-WPRPVWTQSA-N Ephedroxane Chemical compound O1C(=O)N(C)[C@@H](C)[C@H]1C1=CC=CC=C1 MNYARIILPGRTQL-WPRPVWTQSA-N 0.000 description 1
- 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 1
- 239000005909 Kieselgur Substances 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 235000005018 Pinus echinata Nutrition 0.000 description 1
- 235000013264 Pinus jeffreyi Nutrition 0.000 description 1
- 235000016013 Pinus leiophylla var chihuahuana Nutrition 0.000 description 1
- 240000007320 Pinus strobus Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000219053 Rumex Species 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000013100 final test Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 235000013490 limbo Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- MFAHORNLUJVSKK-UHFFFAOYSA-N n-(3-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC(C)=C1 MFAHORNLUJVSKK-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7233960 | 1972-09-26 | ||
| FR7233960A FR2201035B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-09-26 | 1972-09-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS49100040A JPS49100040A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-09-20 |
| JPS5811855B2 true JPS5811855B2 (ja) | 1983-03-04 |
Family
ID=9104771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP48105100A Expired JPS5811855B2 (ja) | 1972-09-26 | 1973-09-19 | 新規な置換クロトンアニリドの製造法 |
Country Status (15)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2268010B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-04-22 | 1976-10-29 | Roussel Uclaf | |
| GB1564387A (en) * | 1976-06-30 | 1980-04-10 | Kao Corp | Germicidal herbicide compositions for use in agriculture and horticulture containing active ingredients amides of alkylthioalkylsulphinyl and alkylsulphonyl-acrylic acids |
-
1972
- 1972-09-26 FR FR7233960A patent/FR2201035B1/fr not_active Expired
-
1973
- 1973-08-21 DD DD173003A patent/DD112712A5/xx unknown
- 1973-08-26 IL IL43076A patent/IL43076A/xx unknown
- 1973-09-04 SE SE7312036A patent/SE408413B/xx unknown
- 1973-09-19 JP JP48105100A patent/JPS5811855B2/ja not_active Expired
- 1973-09-25 CA CA182,013A patent/CA1031789A/en not_active Expired
- 1973-09-25 BE BE136017A patent/BE805281A/xx unknown
- 1973-09-25 SU SU731959057A patent/SU645556A3/ru active
- 1973-09-25 HU HURO752A patent/HU169385B/hu unknown
- 1973-09-25 CH CH1373673A patent/CH587010A5/xx not_active IP Right Cessation
- 1973-09-25 IT IT52745/73A patent/IT1047948B/it active
- 1973-09-25 ES ES419038A patent/ES419038A1/es not_active Expired
- 1973-09-26 DE DE19732348487 patent/DE2348487A1/de not_active Withdrawn
- 1973-09-26 GB GB4511773A patent/GB1393319A/en not_active Expired
- 1973-09-26 NL NL7313245A patent/NL7313245A/xx not_active Application Discontinuation
-
1975
- 1975-08-07 SU SU752162199A patent/SU626675A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| NL7313245A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-28 |
| FR2201035A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-04-26 |
| JPS49100040A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-09-20 |
| IT1047948B (it) | 1980-10-20 |
| SE408413B (sv) | 1979-06-11 |
| DD112712A5 (de) | 1975-05-05 |
| ES419038A1 (es) | 1976-03-01 |
| HU169385B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-11-28 |
| SU645556A3 (ru) | 1979-01-30 |
| IL43076A0 (en) | 1973-11-28 |
| FR2201035B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-04-25 |
| SU626675A3 (ru) | 1978-09-30 |
| DE2348487A1 (de) | 1974-04-04 |
| CH587010A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-04-29 |
| IL43076A (en) | 1978-01-31 |
| GB1393319A (en) | 1975-05-07 |
| CA1031789A (en) | 1978-05-23 |
| BE805281A (fr) | 1974-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 19820420 |