NL8103024A - Werkwijze ter bereiding van 3-(n-aryl-n-acylamino)-)/- butyrothiolactonen. - Google Patents

Werkwijze ter bereiding van 3-(n-aryl-n-acylamino)-)/- butyrothiolactonen. Download PDF

Info

Publication number: NL8103024A
Authority: NL; Netherlands
Prior art keywords: formula; process according; group; compound; acid
Prior art date: 1980-06-23

Application number

NL8103024A

Other languages

English (en)

Dutch (nl)

Original Assignee

Chevron Res

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.)

1980-06-23

Filing date

1981-06-23

Publication date

1982-01-18

1980-09-08 Priority claimed from US06/184,846 external-priority patent/US4311849A/en

1981-06-23 Application filed by Chevron Res filed Critical Chevron Res

1982-01-18 Publication of NL8103024A publication Critical patent/NL8103024A/nl

Links

238000004519 manufacturing process Methods 0.000 title claims description 4
-1 epoxyalkyl Chemical group 0.000 claims description 80
238000000034 method Methods 0.000 claims description 64
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
150000001875 compounds Chemical class 0.000 claims description 44
239000000203 mixture Substances 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
239000003795 chemical substances by application Substances 0.000 claims description 17
239000003960 organic solvent Substances 0.000 claims description 17
125000001424 substituent group Chemical group 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 16
229910052801 chlorine Inorganic materials 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
150000001266 acyl halides Chemical class 0.000 claims description 14
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 13
239000007858 starting material Substances 0.000 claims description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 10
YEJRWHAVMIAJKC-UHFFFAOYSA-N gamma-butyrolactone Natural products O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 10
239000007788 liquid Substances 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
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230000010933 acylation Effects 0.000 claims description 9
238000005917 acylation reaction Methods 0.000 claims description 9
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239000011737 fluorine Substances 0.000 claims description 9
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239000003153 chemical reaction reagent Substances 0.000 claims description 7
125000005359 phenoxyalkyl group Chemical group 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 6
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125000003118 aryl group Chemical group 0.000 claims description 6
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ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
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238000007363 ring formation reaction Methods 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
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125000001188 haloalkyl group Chemical group 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
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238000006798 ring closing metathesis reaction Methods 0.000 claims 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
150000001768 cations Chemical class 0.000 claims 1
238000009833 condensation Methods 0.000 claims 1
230000005494 condensation Effects 0.000 claims 1
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239000000047 product Substances 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
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230000000855 fungicidal effect Effects 0.000 description 13
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239000011230 binding agent Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
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239000011734 sodium Substances 0.000 description 5
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159000000000 sodium salts Chemical class 0.000 description 5
150000007944 thiolates Chemical class 0.000 description 5
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
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WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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239000002270 dispersing agent Substances 0.000 description 4
238000011065 in-situ storage Methods 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
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ZBRWJPVULTZZCE-UHFFFAOYSA-N 1-propylsulfanylbutane Chemical compound CCCCSCCC ZBRWJPVULTZZCE-UHFFFAOYSA-N 0.000 description 2
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LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
241001281803 Plasmopara viticola Species 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
240000003768 Solanum lycopersicum Species 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
241000219094 Vitaceae Species 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
BQCLJECBJVWSES-UHFFFAOYSA-N acetyl chloride;hydrochloride Chemical compound Cl.CC(Cl)=O BQCLJECBJVWSES-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001262 acyl bromides Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000002490 anilino group Chemical group [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
230000000844 anti-bacterial effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001767 cationic compounds Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000011362 coarse particle Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000012084 conversion product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
PYFRLDVYGBCYLI-UHFFFAOYSA-N decyl dihydrogen phosphite Chemical compound CCCCCCCCCCOP(O)O PYFRLDVYGBCYLI-UHFFFAOYSA-N 0.000 description 1
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
239000002027 dichloromethane extract Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
235000021021 grapes Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
229910001411 inorganic cation Inorganic materials 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
150000002596 lactones Chemical class 0.000 description 1
239000004571 lime Substances 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
235000011160 magnesium carbonates Nutrition 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
239000003595 mist Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
GLBUZFYJIIWCFB-UHFFFAOYSA-N propanethioyl chloride Chemical compound CCC(Cl)=S GLBUZFYJIIWCFB-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([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
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide 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
VWKXRZMCFJSACA-UHFFFAOYSA-M sodium 2-methylbutane-2-thiolate Chemical compound [Na+].CCC(C)(C)[S-] VWKXRZMCFJSACA-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
235000001508 sulfur Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

NL8103024A 1980-06-23 1981-06-23 Werkwijze ter bereiding van 3-(n-aryl-n-acylamino)-)/- butyrothiolactonen. NL8103024A (nl)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US16245380A	1980-06-23	1980-06-23
US16245380		1980-06-23
US18484680		1980-09-08
US06/184,846 US4311849A (en)	1980-09-08	1980-09-08	Process for making 3-(N-arylamino)-gamma-butyrothiolactones
US20086480A	1980-10-27	1980-10-27
US20086480		1980-10-27

Publications (1)

Publication Number	Publication Date
NL8103024A true NL8103024A (nl)	1982-01-18

Family

ID=27388753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8103024A NL8103024A (nl)	1980-06-23	1981-06-23	Werkwijze ter bereiding van 3-(n-aryl-n-acylamino)-)/- butyrothiolactonen.

Country Status (8)

Country	Link
CH (1)	CH648307A5 (de)
DD (3)	DD203718A5 (de)
DE (1)	DE3123864A1 (de)
ES (3)	ES8300105A1 (de)
FR (3)	FR2485013A1 (de)
GB (1)	GB2078741B (de)
IT (1)	IT1136849B (de)
NL (1)	NL8103024A (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5175310A (en) *	1990-03-16	1992-12-29	Elf Atochem North America, Inc.	Process for producing alkylthio- and arylthio-substituted carboxylic acids and their thioesters
CN1035252C (zh) *	1993-11-23	1997-06-25	王桂英	氨甲基甲酸-1，1，1-三氯-2-(2,4－二氯硫酚基) 乙基酯及其制备方法
ES2088817B1 (es) *	1993-12-02	1997-08-01	Univ La Laguna	Control de nematodos fitoparasitos con lignanos tipo dibencil-butirolactonas.
CN114891221B (zh) *	2019-10-14	2023-09-15	中国科学院上海有机化学研究所	聚（γ-硫代丁内酯）

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2408601A1 (fr) *	1977-11-01	1979-06-08	Chevron Res	Procede d'acylation d'une aniline substituee par une lactone en l'absence d'accepteur d'acide
BR8000986A (pt) *	1979-02-22	1980-10-29	Chevron Res	Composto fungicida, processo para controlar o crescimento de fungos, composicao fungicidas e processo para o controle de fungos
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

1981
- 1981-06-16 DE DE19813123864 patent/DE3123864A1/de not_active Withdrawn
- 1981-06-19 FR FR8112167A patent/FR2485013A1/fr active Granted
- 1981-06-22 IT IT22482/81A patent/IT1136849B/it active
- 1981-06-23 NL NL8103024A patent/NL8103024A/nl not_active Application Discontinuation
- 1981-06-23 ES ES503313A patent/ES8300105A1/es not_active Expired
- 1981-06-23 DD DD81244216A patent/DD203718A5/de unknown
- 1981-06-23 DD DD81244217A patent/DD209443A5/de unknown
- 1981-06-23 GB GB8119334A patent/GB2078741B/en not_active Expired
- 1981-06-23 DD DD81231058A patent/DD160416A5/de unknown
- 1981-06-23 CH CH4154/81A patent/CH648307A5/de not_active IP Right Cessation
- 1981-11-17 FR FR8121478A patent/FR2491069B1/fr not_active Expired
- 1981-11-17 FR FR8121477A patent/FR2491062A1/fr active Granted
1982
- 1982-06-14 ES ES513070A patent/ES8304114A1/es not_active Expired
- 1982-06-14 ES ES513071A patent/ES8304115A1/es not_active Expired

Also Published As

Publication number	Publication date
ES513071A0 (es)	1983-02-16
DD203718A5 (de)	1983-11-02
ES503313A0 (es)	1982-10-01
FR2485013B1 (de)	1984-06-29
FR2491069A1 (de)	1982-04-02
CH648307A5 (de)	1985-03-15
IT1136849B (it)	1986-09-03
FR2491062A1 (fr)	1982-04-02
DD160416A5 (de)	1983-07-27
FR2485013A1 (fr)	1981-12-24
GB2078741B (en)	1984-02-08
GB2078741A (en)	1982-01-13
ES513070A0 (es)	1983-02-16
ES8300105A1 (es)	1982-10-01
IT8122482A0 (it)	1981-06-22
DE3123864A1 (de)	1982-03-04
ES8304115A1 (es)	1983-02-16
ES8304114A1 (es)	1983-02-16
FR2491062B1 (de)	1985-01-18
FR2491069B1 (de)	1983-12-16
DD209443A5 (de)	1984-05-09

Publication	Publication Date	Title
JPH03218355A (ja)	1991-09-25	含窒素異項環オキシーフェノキシ酢酸誘導体およびその除草剤としての用途
US4098896A (en)	1978-07-04	1-Halohydrocarbylthio-3-hydrocarbylthio-4-substituted-1,2,4-delta2 -triazolidin-5-ones
US4792565A (en)	1988-12-20	Pyrazolecarbonylamine derivatives and agricultural and horticultural fungicides containing said compounds
US4440780A (en)	1984-04-03	Fungicidal 3-(N-acyl-N-arylamino)-and 3-(N-thionoacyl-N-arylamino)-gamma-butyrolactones and gamma-thiobutyrolactones
NL8103024A (nl)	1982-01-18	Werkwijze ter bereiding van 3-(n-aryl-n-acylamino)-)/- butyrothiolactonen.
PT86609B (pt)	1991-12-31	Processo para a preparacao duma composicao fungicida contendo 1-aminometil-3-aril-4-ciano-pirrois
IE47577B1 (en)	1984-05-02	Fungicidal butyrolactones and butyrothiolactones
US4107323A (en)	1978-08-15	Fungicidal 3-(N-acyl-N-arylamino) lactones and lactams
CS266558B2 (en)	1990-01-12	Fungicide and method of its efficient substance production
CS270566B2 (en)	1990-07-12	Fungicide and method of its active substance production
EP0057027B1 (de)	1986-07-30	Fungizide
AU593224B2 (en)	1990-02-08	4-phenyl-3-oxo-2,3-dihydrothiophene derivatives and their useas herbicides
US4460603A (en)	1984-07-17	1-(2'-Haloalkyl)-amidomethyl-substituted acetanilide fungicides
JP2526067B2 (ja)	1996-08-21	置換ピリジン系化合物及びその製造方法
CA1156664A (en)	1983-11-08	Process for preparing 3-(n-aryl-n-acylamino)-gamma- butyrothiolate
HUT65081A (en)	1994-04-28	Substituted salycilamide-derivates, fungicidal compositions containing them and method for their preparation and for their use against plant-dieses
US4382954A (en)	1983-05-10	Fungicidal N-1-substituted cyclopropyl-N-acyl-2,6-dialkylaniline
CA1182464A (en)	1985-02-12	Process for preparing 3-(n-aryl-n-acylamino)-gamma- butyrothiolate
EP0152129B1 (de)	1991-06-12	N-Acyl-Aminosäure-Derivate, Herstellungsverfahren und Verwendung als Herbizide
SU727103A3 (ru)	1980-04-05	Гербицидное и фунгицидное средство
US4340739A (en)	1982-07-20	N-Halomethylanilides
EP0412681B1 (de)	1994-09-28	Azolidin-Derivate, Verfahren zu deren Herstellung und Fungizide für die Landwirtschaft und den Gartenbau
CA1065332A (en)	1979-10-30	Acylated phenylamino thiopropionates
CA1158654A (en)	1983-12-13	Fungicidal 3-(n-thionoacyl-n-arylamino) lactones and thiolactones
GB2046249A (en)	1980-11-12	Fungicidal 3-(N-acyl or thioacyl- N-arylamino)-gamma-butyrolactones and butyrothiolactones

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1988-02-01	BV	The patent application has lapsed