IE46787B1

IE46787B1 - Esters and thiolesters of amino acids,processes for their production, and compositions including them

Esters and thiolesters of amino acids,processes for their production, and compositions including them

Info

Publication number: IE46787B1
Authority: IE; Ireland
Prior art keywords: valine; ester; hydrogen; phenoxybenzyl; fluoro
Prior art date: 1977-03-21

Application number

IE552/78A

Other languages

English (en)

Other versions

IE780552L (en

Original Assignee

Zoecon Corp

Priority date

1977-03-21

Filing date

1978-03-20

Publication date

1983-09-21

1978-02-16 Priority claimed from US05/878,091 external-priority patent/US4243819A/en

1978-03-20 Application filed by Zoecon Corp filed Critical Zoecon Corp

1978-09-21 Publication of IE780552L publication Critical patent/IE780552L/xx

1983-09-21 Publication of IE46787B1 publication Critical patent/IE46787B1/en

Links

238000000034 method Methods 0.000 title claims description 107
239000000203 mixture Substances 0.000 title claims description 58
238000004519 manufacturing process Methods 0.000 title claims 2
150000002148 esters Chemical class 0.000 title abstract description 67
150000001413 amino acids Chemical class 0.000 title abstract description 8
150000007970 thio esters Chemical class 0.000 title abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 64
-1 methylenedioxy group Chemical group 0.000 claims description 282
239000001257 hydrogen Substances 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 41
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 37
125000004432 carbon atom Chemical group C* 0.000 claims description 34
125000000217 alkyl group Chemical group 0.000 claims description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 26
DLULJAUWRRKBML-JTQLQIEISA-N (2s)-2-[2-fluoro-4-(trifluoromethyl)anilino]-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(C(F)(F)F)C=C1F DLULJAUWRRKBML-JTQLQIEISA-N 0.000 claims description 25
150000002431 hydrogen Chemical class 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
125000001153 fluoro group Chemical group F* 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
241000238631 Hexapoda Species 0.000 claims description 13
241000607479 Yersinia pestis Species 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000003710 aryl alkyl group Chemical group 0.000 claims description 11
125000001309 chloro group Chemical group Cl* 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
YKSHSSFDOHACTC-JTQLQIEISA-N (2s)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(C(F)(F)F)C=C1Cl YKSHSSFDOHACTC-JTQLQIEISA-N 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000001188 haloalkyl group Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
125000001246 bromo group Chemical group Br* 0.000 claims description 7
241000238876 Acari Species 0.000 claims description 6
125000000262 haloalkenyl group Chemical group 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 5
125000003302 alkenyloxy group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000004438 haloalkoxy group Chemical group 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
150000007522 mineralic acids Chemical class 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
241000255925 Diptera Species 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
125000005133 alkynyloxy group Chemical group 0.000 claims description 4
125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
125000005110 aryl thio group Chemical group 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 3
125000005291 haloalkenyloxy group Chemical group 0.000 claims description 3
125000004995 haloalkylthio group Chemical group 0.000 claims description 3
125000000232 haloalkynyl group Chemical group 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 claims description 2
241000254173 Coleoptera Species 0.000 claims description 2
241000258937 Hemiptera Species 0.000 claims description 2
241001466007 Heteroptera Species 0.000 claims description 2
241000257303 Hymenoptera Species 0.000 claims description 2
241000255777 Lepidoptera Species 0.000 claims description 2
241000238814 Orthoptera Species 0.000 claims description 2
241000916145 Tarsonemidae Species 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
229940098779 methanesulfonic acid Drugs 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 2
241001454295 Tetranychidae Species 0.000 claims 1
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
230000000895 acaricidal effect Effects 0.000 abstract 1
230000000749 insecticidal effect Effects 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 238
KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 101
239000004474 valine Substances 0.000 description 101
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 94
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 87
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 76
238000006243 chemical reaction Methods 0.000 description 71
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 58
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
FBCHRMFAWNWJCU-JTQLQIEISA-N (2s)-2-(4-chloroanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(Cl)C=C1 FBCHRMFAWNWJCU-JTQLQIEISA-N 0.000 description 47
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 45
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
UJUNUASMYSTBSK-UHFFFAOYSA-N 1-(bromomethyl)-3-phenoxybenzene Chemical compound BrCC1=CC=CC(OC=2C=CC=CC=2)=C1 UJUNUASMYSTBSK-UHFFFAOYSA-N 0.000 description 42
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 42
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
239000012267 brine Substances 0.000 description 39
239000000243 solution Substances 0.000 description 37
235000019441 ethanol Nutrition 0.000 description 34
239000011541 reaction mixture Substances 0.000 description 33
UEBARDWJXBGYEJ-UHFFFAOYSA-N 2-bromo-3-methylbutanoic acid Chemical compound CC(C)C(Br)C(O)=O UEBARDWJXBGYEJ-UHFFFAOYSA-N 0.000 description 32
229910000027 potassium carbonate Inorganic materials 0.000 description 29
AJWAECPVBMQFSX-NSHDSACASA-N (2s)-3-methyl-2-(4-methylanilino)butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(C)C=C1 AJWAECPVBMQFSX-NSHDSACASA-N 0.000 description 27
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 27
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 24
239000002904 solvent Substances 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
229910052757 nitrogen Inorganic materials 0.000 description 20
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
238000004809 thin layer chromatography Methods 0.000 description 17
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 16
239000010410 layer Substances 0.000 description 16
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
239000012259 ether extract Substances 0.000 description 15
159000000000 sodium salts Chemical class 0.000 description 15
229910052938 sodium sulfate Inorganic materials 0.000 description 15
235000011152 sodium sulphate Nutrition 0.000 description 15
238000003756 stirring Methods 0.000 description 15
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 14
239000005457 ice water Substances 0.000 description 13
KZPLXTSZVZBJPO-JTQLQIEISA-N (2s)-2-(4-chloro-2-fluoroanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(Cl)C=C1F KZPLXTSZVZBJPO-JTQLQIEISA-N 0.000 description 12
NZPWGWAEKDSVFN-JTQLQIEISA-N (2s)-3-methyl-2-[4-(trifluoromethyl)anilino]butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(C(F)(F)F)C=C1 NZPWGWAEKDSVFN-JTQLQIEISA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000008346 aqueous phase Substances 0.000 description 12
239000012071 phase Substances 0.000 description 11
HNBHHMUCXASXEW-UHFFFAOYSA-N (3-phenoxyphenyl)methyl 2-bromo-3-methylbutanoate Chemical compound CC(C)C(Br)C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 HNBHHMUCXASXEW-UHFFFAOYSA-N 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 9
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 9
238000012746 preparative thin layer chromatography Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
CAXWIGJTXJTLLU-JTQLQIEISA-N (2s)-2-(4-bromo-2-fluoroanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(Br)C=C1F CAXWIGJTXJTLLU-JTQLQIEISA-N 0.000 description 8
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 8
WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 8
230000007935 neutral effect Effects 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
238000010992 reflux Methods 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
101150041968 CDC13 gene Proteins 0.000 description 7
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
229940024606 amino acid Drugs 0.000 description 7
238000001035 drying Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
238000005192 partition Methods 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
XCAMLAFYNOLVPM-NSHDSACASA-N (2s)-2-(2,6-dimethylanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=C(C)C=CC=C1C XCAMLAFYNOLVPM-NSHDSACASA-N 0.000 description 6
LYJVJCQYQYSJHU-NSHDSACASA-N (2s)-2-(2-fluoro-4-methylanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(C)C=C1F LYJVJCQYQYSJHU-NSHDSACASA-N 0.000 description 6
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000012043 crude product Substances 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
XZUCJVTXERYPQH-NSHDSACASA-N (2s)-2-(4-methoxyanilino)-3-methylbutanoic acid Chemical compound COC1=CC=C(N[C@@H](C(C)C)C(O)=O)C=C1 XZUCJVTXERYPQH-NSHDSACASA-N 0.000 description 5
MBRPCSKHPRLQQQ-JTQLQIEISA-N (2s)-2-anilino-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=CC=C1 MBRPCSKHPRLQQQ-JTQLQIEISA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
CSFDTBRRIBJILD-UHFFFAOYSA-N 4-chloro-2-fluoroaniline Chemical compound NC1=CC=C(Cl)C=C1F CSFDTBRRIBJILD-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
CQVOILYSLSWABZ-NSHDSACASA-N (2s)-2-(2-fluoro-4-methoxyanilino)-3-methylbutanoic acid Chemical compound COC1=CC=C(N[C@@H](C(C)C)C(O)=O)C(F)=C1 CQVOILYSLSWABZ-NSHDSACASA-N 0.000 description 4
XWTQCMHYIJEQPD-JTQLQIEISA-N (2s)-2-(4-chloro-3-fluoroanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(Cl)C(F)=C1 XWTQCMHYIJEQPD-JTQLQIEISA-N 0.000 description 4
IUKZSVHIWMVLEQ-NSHDSACASA-N (2s)-3-methyl-2-(2-methylanilino)butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=CC=C1C IUKZSVHIWMVLEQ-NSHDSACASA-N 0.000 description 4
ZQEXBVHABAJPHJ-UHFFFAOYSA-N 2-fluoro-4-methylaniline Chemical compound CC1=CC=C(N)C(F)=C1 ZQEXBVHABAJPHJ-UHFFFAOYSA-N 0.000 description 4
RMXZAXNAIMJGCX-UHFFFAOYSA-N 3-[2-fluoro-4-(trifluoromethyl)phenyl]-4-propan-2-yl-1,3-oxazolidine-2,5-dione Chemical compound O=C1OC(=O)C(C(C)C)N1C1=CC=C(C(F)(F)F)C=C1F RMXZAXNAIMJGCX-UHFFFAOYSA-N 0.000 description 4
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 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
235000019445 benzyl alcohol Nutrition 0.000 description 4
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
150000004702 methyl esters Chemical class 0.000 description 4
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
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SZJQXQICJDHRJE-UHFFFAOYSA-N [3-(bromomethyl)phenyl]-phenylmethanone Chemical compound BrCC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 SZJQXQICJDHRJE-UHFFFAOYSA-N 0.000 description 1
RYULULVJWLRDQH-UHFFFAOYSA-N [4-(bromomethyl)phenyl]-phenylmethanone Chemical compound C1=CC(CBr)=CC=C1C(=O)C1=CC=CC=C1 RYULULVJWLRDQH-UHFFFAOYSA-N 0.000 description 1
150000004729 acetoacetic acid derivatives Chemical class 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229940061720 alpha hydroxy acid Drugs 0.000 description 1
150000001280 alpha hydroxy acids Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001448 anilines 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
150000001450 anions Chemical class 0.000 description 1
239000008365 aqueous carrier Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
210000001142 back Anatomy 0.000 description 1
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
244000309464 bull Species 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
229960005286 carbaryl Drugs 0.000 description 1
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 description 1
230000006196 deacetylation Effects 0.000 description 1
238000003381 deacetylation reaction Methods 0.000 description 1
OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
229950001327 dichlorvos Drugs 0.000 description 1
125000004212 difluorophenyl group Chemical group 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
QFIFUKSTZGHSFY-UHFFFAOYSA-N ethyl 2-(4-chloroanilino)-3,3-dimethylbutanoate Chemical compound CCOC(=O)C(C(C)(C)C)NC1=CC=C(Cl)C=C1 QFIFUKSTZGHSFY-UHFFFAOYSA-N 0.000 description 1
IODMJRFLLIWQIX-UHFFFAOYSA-N ethyl 2-anilino-3-hydroxybutanoate Chemical compound CCOC(=O)C(C(C)O)NC1=CC=CC=C1 IODMJRFLLIWQIX-UHFFFAOYSA-N 0.000 description 1
AKEFSKQAKBVCGG-UHFFFAOYSA-N ethyl 3,3,3-trichloro-2-oxopropanoate Chemical compound CCOC(=O)C(=O)C(Cl)(Cl)Cl AKEFSKQAKBVCGG-UHFFFAOYSA-N 0.000 description 1
KJHQVUNUOIEYSV-UHFFFAOYSA-N ethyl 3,3,3-trifluoro-2-oxopropanoate Chemical compound CCOC(=O)C(=O)C(F)(F)F KJHQVUNUOIEYSV-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000004692 haloalkylcarbonyl group Chemical group 0.000 description 1
JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
FYQGBXGJFWXIPP-UHFFFAOYSA-N hydroprene Chemical compound CCOC(=O)C=C(C)C=CCC(C)CCCC(C)C FYQGBXGJFWXIPP-UHFFFAOYSA-N 0.000 description 1
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XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
239000002949 juvenile hormone Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229930001540 kinoprene Natural products 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
UPRXAOPZPSAYHF-UHFFFAOYSA-N lithium;cyclohexyl(propan-2-yl)azanide Chemical compound CC(C)N([Li])C1CCCCC1 UPRXAOPZPSAYHF-UHFFFAOYSA-N 0.000 description 1
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229930002897 methoprene Natural products 0.000 description 1
229950003442 methoprene Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
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229910003446 platinum oxide Inorganic materials 0.000 description 1
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229920000136 polysorbate Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical class CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
229940070846 pyrethrins Drugs 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
239000012066 reaction slurry Substances 0.000 description 1
VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
229940108410 resmethrin Drugs 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000526 short-path distillation Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910052717 sulfur Chemical group 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
150000003679 valine derivatives Chemical class 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1