NO309263B1 - Fremgangsmåte og mellomproduktforbindelser for fremstilling av pesticide fluorolefinforbindelser - Google Patents

Fremgangsmåte og mellomproduktforbindelser for fremstilling av pesticide fluorolefinforbindelser Download PDF

Info

Publication number: NO309263B1
Authority: NO; Norway
Prior art keywords: groups; optionally substituted; halogen atoms; independently selected; alkyl
Prior art date: 1997-06-19

Application number

NO982811A

Other languages

English (en)

Norwegian (no)

Other versions

NO982811D0 (no

NO982811L (no

Inventor

Brian Lee Buckwalter

Timothy Claude Barden

Original Assignee

American Cyanamid Co

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.)

1997-06-19

Filing date

1998-06-18

Publication date

2001-01-08

1998-06-18 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1998-06-18 Publication of NO982811D0 publication Critical patent/NO982811D0/no

1998-12-21 Publication of NO982811L publication Critical patent/NO982811L/no

2001-01-08 Publication of NO309263B1 publication Critical patent/NO309263B1/no

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 49
238000000034 method Methods 0.000 title claims abstract description 30
238000002360 preparation method Methods 0.000 title abstract description 8
230000000361 pesticidal effect Effects 0.000 title abstract description 7
-1 phenoxyphenyl Chemical group 0.000 claims description 79
125000005843 halogen group Chemical group 0.000 claims description 63
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 47
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 37
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 31
239000002585 base Substances 0.000 claims description 24
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 20
150000004703 alkoxides Chemical class 0.000 claims description 18
229910052799 carbon Inorganic materials 0.000 claims description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
229910052716 thallium Inorganic materials 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
239000002904 solvent Substances 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
125000004432 carbon atom Chemical group C* 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 11
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
125000001188 haloalkyl group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 8
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 8
238000007127 saponification reaction Methods 0.000 claims description 8
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 7
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 7
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 7
150000008366 benzophenones Chemical group 0.000 claims description 7
239000004305 biphenyl Chemical group 0.000 claims description 7
235000010290 biphenyl Nutrition 0.000 claims description 7
239000003638 chemical reducing agent Substances 0.000 claims description 7
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 6
150000001342 alkaline earth metals Chemical class 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims description 6
125000004438 haloalkoxy group Chemical group 0.000 claims description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
VMDJWSACUFRJRE-UHFFFAOYSA-N 2-fluoro-3,3-dimethyl-1,2-benzothiazole 1,1-dioxide Chemical compound C1=CC=C2C(C)(C)N(F)S(=O)(=O)C2=C1 VMDJWSACUFRJRE-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000012025 fluorinating agent Substances 0.000 claims description 5
238000003682 fluorination reaction Methods 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
150000003512 tertiary amines Chemical class 0.000 claims description 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 4
150000008041 alkali metal carbonates Chemical class 0.000 claims description 4
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 4
150000008046 alkali metal hydrides Chemical class 0.000 claims description 4
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 4
125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
229910000510 noble metal Inorganic materials 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
PBJTXVTVKNXWHU-UHFFFAOYSA-N dioxidoboranyloxy(fluoro)borinate 1-fluoropyridin-1-ium pyridine Chemical compound C1=CC=NC=C1.[O-]B([O-])OB([O-])F.[O-]B([O-])OB([O-])F.[O-]B([O-])OB([O-])F.[O-]B([O-])OB([O-])F.[O-]B([O-])OB([O-])F.[O-]B([O-])OB([O-])F.[O-]B([O-])OB([O-])F.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1 PBJTXVTVKNXWHU-UHFFFAOYSA-N 0.000 claims description 3
RLKHFSNWQCZBDC-UHFFFAOYSA-N n-(benzenesulfonyl)-n-fluorobenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(F)S(=O)(=O)C1=CC=CC=C1 RLKHFSNWQCZBDC-UHFFFAOYSA-N 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 3
150000003222 pyridines Chemical class 0.000 claims description 3
YYWXRGZEVMGXRG-UHFFFAOYSA-N 3-fluoro-4h-oxathiazine 2-oxide Chemical compound FN1CC=COS1=O YYWXRGZEVMGXRG-UHFFFAOYSA-N 0.000 claims description 2
229910052782 aluminium Inorganic materials 0.000 claims 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000012267 brine Substances 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
239000003921 oil Substances 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
238000010183 spectrum analysis Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
230000003595 spectral effect Effects 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001339 alkali metal compounds Chemical class 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000000605 extraction Methods 0.000 description 2
150000004795 grignard reagents Chemical class 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
229910052723 transition metal Inorganic materials 0.000 description 2
150000003624 transition metals Chemical class 0.000 description 2
239000008096 xylene Substances 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
HEGXENQCLACJQG-UHFFFAOYSA-N 1-(4-chlorophenyl)cyclopropane-1-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1C1(C=O)CC1 HEGXENQCLACJQG-UHFFFAOYSA-N 0.000 description 1
UJUNUASMYSTBSK-UHFFFAOYSA-N 1-(bromomethyl)-3-phenoxybenzene Chemical compound BrCC1=CC=CC(OC=2C=CC=CC=2)=C1 UJUNUASMYSTBSK-UHFFFAOYSA-N 0.000 description 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000004652 butanoic acids Chemical class 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
MOLRJCRTZIEBKH-UHFFFAOYSA-N cyclopropane propanoic acid Chemical compound C(CC)(=O)O.C1CC1 MOLRJCRTZIEBKH-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
RGEGNKPXYPUKCC-UHFFFAOYSA-N ethyl 3-[1-(4-chlorophenyl)cyclopropyl]-2-fluoro-3-hydroxy-2-[(3-phenoxyphenyl)methyl]propanoate Chemical compound C1CC1(C=1C=CC(Cl)=CC=1)C(O)C(F)(C(=O)OCC)CC(C=1)=CC=CC=1OC1=CC=CC=C1 RGEGNKPXYPUKCC-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 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
229910000029 sodium carbonate Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
- C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Landscapes

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

NO982811A 1997-06-19 1998-06-18 Fremgangsmåte og mellomproduktforbindelser for fremstilling av pesticide fluorolefinforbindelser NO309263B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US5016697P	1997-06-19	1997-06-19

Publications (3)

Publication Number	Publication Date
NO982811D0 NO982811D0 (no)	1998-06-18
NO982811L NO982811L (no)	1998-12-21
NO309263B1 true NO309263B1 (no)	2001-01-08

Family

ID=21963709

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO982811A NO309263B1 (no)	1997-06-19	1998-06-18	Fremgangsmåte og mellomproduktforbindelser for fremstilling av pesticide fluorolefinforbindelser

Country Status (31)

Country	Link
US (1)	US5973190A (da)
EP (1)	EP0885867B1 (da)
JP (1)	JPH11147857A (da)
KR (1)	KR100522107B1 (da)
CN (1)	CN1138735C (da)
AR (1)	AR013003A1 (da)
AT (1)	ATE207457T1 (da)
AU (1)	AU724762B2 (da)
BG (1)	BG102563A (da)
BR (1)	BR9802017A (da)
CA (1)	CA2240886A1 (da)
CO (1)	CO5040072A1 (da)
CZ (1)	CZ188698A3 (da)
DE (1)	DE69802140T2 (da)
DK (1)	DK0885867T3 (da)
ES (1)	ES2166590T3 (da)
GE (1)	GEP20022795B (da)
HU (1)	HU220279B (da)
ID (1)	ID20465A (da)
IL (1)	IL124924A (da)
MD (1)	MD980145A (da)
NO (1)	NO309263B1 (da)
NZ (1)	NZ330695A (da)
PL (1)	PL326881A1 (da)
RU (1)	RU2193022C2 (da)
SG (1)	SG66481A1 (da)
SK (1)	SK84798A3 (da)
TR (1)	TR199801109A2 (da)
TW (1)	TW457228B (da)
YU (1)	YU26598A (da)
ZA (1)	ZA985387B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL154438A0 (en) *	2000-09-12	2003-09-17	Basf Ag	Process and intermediate compounds for the preparation of pesticidal fluoroolefin compounds
KR102245731B1 (ko)	2020-10-26	2021-04-28	주식회사 삼정오디세이	샤프트 및 이의 제조방법

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SU1058101A1 (ru) *	1982-02-22	1990-01-15	Институт Химии Ан Эсср	1-(4-Этилфенокси)-3-метил-5-изопропокси-2-пентен, обладающий инсектицидной активностью
DE3505370A1 (de) *	1985-02-14	1986-08-14	Schering AG, 1000 Berlin und 4709 Bergkamen	Aromatische alkanderivate, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung
US4975451A (en) *	1989-03-02	1990-12-04	Fmc Corporation	Insecticidal cyclopropyl di(aryl) 2-butenes
GB9219612D0 (en) *	1992-09-16	1992-10-28	Khambay Bhupinder P S	Pesticidal fluoroolefins
GB9408605D0 (en) *	1994-04-29	1994-06-22	British Tech Group	Pesticidal fluoroolefins
GB9522144D0 (en) *	1995-10-30	1996-01-03	British Tech Group	Control of whitefly

1998
- 1998-06-11 GE GEAP19984341A patent/GEP20022795B/en unknown
- 1998-06-15 IL IL12492498A patent/IL124924A/en not_active IP Right Cessation
- 1998-06-16 DK DK98304738T patent/DK0885867T3/da active
- 1998-06-16 EP EP98304738A patent/EP0885867B1/en not_active Expired - Lifetime
- 1998-06-16 ES ES98304738T patent/ES2166590T3/es not_active Expired - Lifetime
- 1998-06-16 JP JP10183280A patent/JPH11147857A/ja not_active Ceased
- 1998-06-16 CZ CZ981886A patent/CZ188698A3/cs unknown
- 1998-06-16 NZ NZ330695A patent/NZ330695A/xx unknown
- 1998-06-16 AT AT98304738T patent/ATE207457T1/de not_active IP Right Cessation
- 1998-06-16 DE DE69802140T patent/DE69802140T2/de not_active Expired - Fee Related
- 1998-06-16 TR TR1998/01109A patent/TR199801109A2/xx unknown
- 1998-06-17 BR BR9802017A patent/BR9802017A/pt not_active Application Discontinuation
- 1998-06-17 KR KR1019980022709A patent/KR100522107B1/ko not_active Expired - Fee Related
- 1998-06-17 CA CA002240886A patent/CA2240886A1/en not_active Abandoned
- 1998-06-17 SG SG1998001445A patent/SG66481A1/en unknown
- 1998-06-17 CO CO98034403A patent/CO5040072A1/es unknown
- 1998-06-18 YU YU26598A patent/YU26598A/sr unknown
- 1998-06-18 US US09/099,101 patent/US5973190A/en not_active Expired - Fee Related
- 1998-06-18 ID IDP980888A patent/ID20465A/id unknown
- 1998-06-18 MD MD98-0145A patent/MD980145A/ro unknown
- 1998-06-18 HU HU9801375A patent/HU220279B/hu not_active IP Right Cessation
- 1998-06-18 CN CNB981149324A patent/CN1138735C/zh not_active Expired - Fee Related
- 1998-06-18 PL PL98326881A patent/PL326881A1/xx unknown
- 1998-06-18 SK SK847-98A patent/SK84798A3/sk unknown
- 1998-06-18 AR ARP980102917A patent/AR013003A1/es unknown
- 1998-06-18 NO NO982811A patent/NO309263B1/no not_active IP Right Cessation
- 1998-06-18 RU RU98111641/04A patent/RU2193022C2/ru not_active IP Right Cessation
- 1998-06-18 AU AU71968/98A patent/AU724762B2/en not_active Ceased
- 1998-06-19 BG BG102563A patent/BG102563A/xx unknown
- 1998-06-19 ZA ZA9805387A patent/ZA985387B/xx unknown
- 1998-06-19 TW TW087109826A patent/TW457228B/zh not_active IP Right Cessation

Also Published As

Publication number	Publication date
TR199801109A3 (tr)	1999-01-18
SK84798A3 (en)	1999-01-11
EP0885867A1 (en)	1998-12-23
DE69802140D1 (de)	2001-11-29
DK0885867T3 (da)	2001-11-19
KR100522107B1 (ko)	2006-01-27
CZ188698A3 (cs)	1999-01-13
CN1203216A (zh)	1998-12-30
YU26598A (en)	1999-11-22
ES2166590T3 (es)	2002-04-16
AR013003A1 (es)	2000-11-22
HUP9801375A1 (hu)	1999-05-28
IL124924A (en)	2001-08-08
JPH11147857A (ja)	1999-06-02
KR19990007056A (ko)	1999-01-25
NZ330695A (en)	1999-07-29
MD980145A (ro)	2000-01-31
EP0885867B1 (en)	2001-10-24
IL124924A0 (en)	1999-01-26
RU2193022C2 (ru)	2002-11-20
AU7196898A (en)	1998-12-24
BG102563A (en)	1999-04-30
US5973190A (en)	1999-10-26
NO982811D0 (no)	1998-06-18
PL326881A1 (en)	1998-12-21
TW457228B (en)	2001-10-01
HU9801375D0 (en)	1998-08-28
BR9802017A (pt)	1999-07-20
ATE207457T1 (de)	2001-11-15
CO5040072A1 (es)	2001-05-29
ZA985387B (en)	1999-12-20
DE69802140T2 (de)	2002-06-20
AU724762B2 (en)	2000-09-28
CA2240886A1 (en)	1998-12-19
SG66481A1 (en)	1999-07-20
CN1138735C (zh)	2004-02-18
ID20465A (id)	1998-12-24
TR199801109A2 (xx)	1999-01-18
GEP20022795B (en)	2002-09-25
NO982811L (no)	1998-12-21
HU220279B (hu)	2001-11-28

Legal Events

Date	Code	Title	Description
2003-02-10	MM1K	Lapsed by not paying the annual fees	Free format text: LAPSED IN DECEMBER 2003

Publication	Publication Date	Title
CA1340854C (en)	1999-12-21	Process for the preparation of 3-substituted derivatives of 1-amino 2-hydroxy-propane
US7214835B2 (en)	2007-05-08	1,7,8-Trifluoronaphthalene-2-naphthol, and method for producing liquid crystal compound using same
NO309263B1 (no)	2001-01-08	Fremgangsmåte og mellomproduktforbindelser for fremstilling av pesticide fluorolefinforbindelser
NO175101B (no)	1994-05-24	Analogifremgangsmåte for fremstilling av nye, terapeutisk aktive fluornaftacendioner samt mellomprodukter
US5426247A (en)	1995-06-20	Process for the preparation of vitamin A and intermediate compounds which are useful for this process
MXPA06011514A (es)	2007-08-02	Derivados de indeno y proceso para la preparacion de los mismos.
EP0276558B1 (en)	1992-07-08	Insecticidal ethers
US4642384A (en)	1987-02-10	Process for the preparation of derivatives of pyrrolidine and piperidine
US5841004A (en)	1998-11-24	3-substituted-α, β-dibromoethylbenzene and process for preparing the same
JPH05286882A (ja)	1993-11-02	２，３−ジフルオロフェノール類の製造方法
US4650873A (en)	1987-03-17	Process for the preparation of a derivative of piperidine
US6342642B1 (en)	2002-01-29	1,4-diaryl-2-fluoro-1-buten-3-ol compounds and their use in the preparation of 1,4-diaryl-2-fluoro-1,3-butadiene and 1,4-diaryl-2-fluoro-2-butene compounds
US4417064A (en)	1983-11-22	Biphenyl compounds and method of preparing same
AU702043B2 (en)	1999-02-11	Dihalopropene compounds, insecticidal/acaricidal agents containing same, and intermediates for their production
US5599935A (en)	1997-02-04	Bisquinolinol and bisbenzoquinolinol compounds, and process for producing same
MXPA98004745A (en)	1999-09-20	Procedure and intermediary compounds for the preparation of compounds of fluorolefine pesticide
JP2000063356A (ja)	2000-02-29	含フッ素ヘテロ環化合物の製造法および含フッ素ヘテロ環化合物
JP4750286B2 (ja)	2011-08-17	反応活性な基を有する新規なビフェニル化合物の製造方法
Mitra et al.	1989	A Facile Synthesis of Ethyl 3-Aryl-2, 2-dimethyl-cyclopropanecarboxylates, Intermediates for Pyrethroid Acaricides
KR20030029973A (ko)	2003-04-16	살충성 플루오로올레핀 화합물의 제조 방법 및 중간체화합물
CZ20011725A3 (cs)	2002-05-15	1,4-Diaryl-2-fluor-1-buten-3-olové sloučeniny a jejich pouľití při přípravě 1,4-diaryl-2-fluor-1,3-butadienových sloučenin a 1,4-diaryl-2-fluor-2-butenových sloučenin
Yoshida et al.	1990	A Convenient Method for the Preparation of 4 (e)-Hydroxy-and 4 (e)-Methoxyadamantan-2-ones
JPH02268134A (ja)	1990-11-01	光学活性２―（４―ヒドロキシフェノキシ）プロピオン酸の製造法
EP1327623A2 (en)	2003-07-16	Process for the production of dichloro hydroquinone ethers
JP2002284764A (ja)	2002-10-03	２−（アルコキシベンジルオキシ）−３−ニトロピリジン及びこれを用いるアルコキシベンジルエーテル化合物の製造法