CA1171874A - Derives de (1,1'-biphenyl)-3-ylmethyl comme produits intermediaires - Google Patents

Derives de (1,1'-biphenyl)-3-ylmethyl comme produits intermediaires

Info

Publication number: CA1171874A
Authority: CA; Canada
Prior art keywords: biphenyl; methyl; mole; fluoro; chloro
Prior art date: 1980-10-02
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000407132A

Other languages

English (en)

Inventor

Ernest L. Plummer

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

FMC Corp

Original Assignee

FMC Corp

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.)

1980-10-02

Filing date

1982-07-12

Publication date

1984-07-31

1980-10-02 Priority claimed from US06/193,056 external-priority patent/US4329518A/en

1981-05-21 Priority claimed from US06/265,940 external-priority patent/US4402973A/en

1982-07-12 Application filed by FMC Corp filed Critical FMC Corp

1982-07-12 Priority to CA000407132A priority Critical patent/CA1171874A/fr

1984-07-31 Application granted granted Critical

1984-07-31 Publication of CA1171874A publication Critical patent/CA1171874A/fr

Status Expired legal-status Critical Current

Links

-1 (1,1'-biphenyl)-3-ylmethyl Chemical class 0.000 title claims abstract description 88
239000000543 intermediate Substances 0.000 title description 10
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 50
125000000217 alkyl group Chemical group 0.000 claims abstract description 26
125000005843 halogen group Chemical group 0.000 claims abstract description 14
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
229910052794 bromium Inorganic materials 0.000 claims abstract description 7
125000001475 halogen functional group Chemical group 0.000 claims abstract description 5
IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims abstract 2
229940074995 bromine Drugs 0.000 claims abstract 2
239000004305 biphenyl Substances 0.000 description 176
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 95
239000011541 reaction mixture Substances 0.000 description 86
239000000243 solution Substances 0.000 description 82
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
150000002148 esters Chemical class 0.000 description 66
239000000203 mixture Substances 0.000 description 65
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
239000003921 oil Substances 0.000 description 43
235000019198 oils Nutrition 0.000 description 43
238000010992 reflux Methods 0.000 description 41
239000000706 filtrate Substances 0.000 description 38
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 35
239000007787 solid Substances 0.000 description 34
238000000034 method Methods 0.000 description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
150000001875 compounds Chemical class 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
238000007792 addition Methods 0.000 description 24
239000002728 pyrethroid Substances 0.000 description 24
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 24
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
239000000741 silica gel Substances 0.000 description 22
229910002027 silica gel Inorganic materials 0.000 description 22
229940073584 methylene chloride Drugs 0.000 description 21
230000000749 insecticidal effect Effects 0.000 description 20
239000002904 solvent Substances 0.000 description 19
230000000895 acaricidal effect Effects 0.000 description 18
239000012074 organic phase Substances 0.000 description 18
238000001228 spectrum Methods 0.000 description 18
238000004440 column chromatography Methods 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
238000010828 elution Methods 0.000 description 15
239000002917 insecticide Substances 0.000 description 15
235000010290 biphenyl Nutrition 0.000 description 14
125000001309 chloro group Chemical group Cl* 0.000 description 14
235000011167 hydrochloric acid Nutrition 0.000 description 14
229960000443 hydrochloric acid Drugs 0.000 description 14
229920006395 saturated elastomer Polymers 0.000 description 14
241000238631 Hexapoda Species 0.000 description 13
239000011780 sodium chloride Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
229950005499 carbon tetrachloride Drugs 0.000 description 12
238000004821 distillation Methods 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
238000012360 testing method Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
239000000284 extract Substances 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
239000012300 argon atmosphere Substances 0.000 description 8
125000001246 bromo group Chemical group Br* 0.000 description 8
239000012065 filter cake Substances 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
239000000969 carrier Substances 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
VSINZTMZSOWVNA-UHFFFAOYSA-N methyl 2,2,3,3-tetramethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C)(C)C1(C)C VSINZTMZSOWVNA-UHFFFAOYSA-N 0.000 description 7
QJOOIMSFFIUFKX-UHFFFAOYSA-N methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(Cl)Cl)C1(C)C QJOOIMSFFIUFKX-UHFFFAOYSA-N 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
241000196324 Embryophyta Species 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
235000008504 concentrate Nutrition 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
239000007788 liquid Substances 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000004342 Benzoyl peroxide Substances 0.000 description 5
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
244000046052 Phaseolus vulgaris Species 0.000 description 5
241001521235 Spodoptera eridania Species 0.000 description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
125000003158 alcohol group Chemical group 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
235000019400 benzoyl peroxide Nutrition 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000002245 particle Substances 0.000 description 5
239000002689 soil Substances 0.000 description 5
239000012258 stirred mixture Substances 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
230000009885 systemic effect Effects 0.000 description 5
OHAMOQALFCXZBV-UHFFFAOYSA-N 2,2-dichloroethenyl 2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)CC1C(=O)OC=C(Cl)Cl OHAMOQALFCXZBV-UHFFFAOYSA-N 0.000 description 4
UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 4
241000462639 Epilachna varivestis Species 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
240000006677 Vicia faba Species 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000004927 clay Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
239000005457 ice water Substances 0.000 description 4
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
238000005191 phase separation Methods 0.000 description 4
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
241000253994 Acyrthosiphon pisum Species 0.000 description 3
241001124076 Aphididae Species 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
239000000642 acaricide Substances 0.000 description 3
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
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 3
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
MOMORSVRSWLPKH-UHFFFAOYSA-N ethyl 6-(2-fluorophenyl)-2-methyl-4-oxocyclohex-2-ene-1-carboxylate Chemical compound C1C(=O)C=C(C)C(C(=O)OCC)C1C1=CC=CC=C1F MOMORSVRSWLPKH-UHFFFAOYSA-N 0.000 description 3
229940093499 ethyl acetate Drugs 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
125000001188 haloalkyl group Chemical group 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
230000008569 process Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011369 resultant mixture Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 3
239000012085 test solution Substances 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
IBWKCPDCFMRCQJ-UHFFFAOYSA-N (2,6-dimethyl-3-nitrophenyl)methanol Chemical compound CC1=CC=C([N+]([O-])=O)C(C)=C1CO IBWKCPDCFMRCQJ-UHFFFAOYSA-N 0.000 description 2
MFPNOMOEXONQIP-UHFFFAOYSA-N (2,6-dimethyl-3-nitrophenyl)methyl acetate Chemical compound CC(=O)OCC1=C(C)C=CC([N+]([O-])=O)=C1C MFPNOMOEXONQIP-UHFFFAOYSA-N 0.000 description 2
VUBUHVBODOUAAF-UHFFFAOYSA-N (3-amino-2-bromophenyl)methyl acetate Chemical compound CC(=O)OCC1=CC=CC(N)=C1Br VUBUHVBODOUAAF-UHFFFAOYSA-N 0.000 description 2
VODBTCPLHMEMAS-UHFFFAOYSA-N (3-amino-2-methylphenyl)methanol;hydrochloride Chemical group Cl.CC1=C(N)C=CC=C1CO VODBTCPLHMEMAS-UHFFFAOYSA-N 0.000 description 2
WVKFJUYXMBJNKD-UHFFFAOYSA-N (3-iodo-2-methylphenyl)methanol Chemical compound CC1=C(I)C=CC=C1CO WVKFJUYXMBJNKD-UHFFFAOYSA-N 0.000 description 2
GKJLIVIFGFYPIV-UHFFFAOYSA-N 1-methyl-2-nitro-3-phenylbenzene Chemical compound CC1=CC=CC(C=2C=CC=CC=2)=C1[N+]([O-])=O GKJLIVIFGFYPIV-UHFFFAOYSA-N 0.000 description 2
NPDIDUXTRAITDE-UHFFFAOYSA-N 1-methyl-3-phenylbenzene Chemical group CC1=CC=CC(C=2C=CC=CC=2)=C1 NPDIDUXTRAITDE-UHFFFAOYSA-N 0.000 description 2
BFNMOMYTTGHNGJ-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1C(O)=O BFNMOMYTTGHNGJ-UHFFFAOYSA-N 0.000 description 2
IMFSHMCSISIQIN-UHFFFAOYSA-N 2-bromo-1-(bromomethyl)-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(CBr)=C1Br IMFSHMCSISIQIN-UHFFFAOYSA-N 0.000 description 2
KKTGNGSNFFLNJQ-UHFFFAOYSA-N 2-ethyl-3-phenylbenzoic acid Chemical compound CCC1=C(C(O)=O)C=CC=C1C1=CC=CC=C1 KKTGNGSNFFLNJQ-UHFFFAOYSA-N 0.000 description 2
NTRUIXLRNRHYNS-UHFFFAOYSA-N 2-methyl-6-phenylaniline Chemical compound CC1=CC=CC(C=2C=CC=CC=2)=C1N NTRUIXLRNRHYNS-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 description 2
VDCZKCIEXGXCDJ-UHFFFAOYSA-N 3-methyl-2-nitroaniline Chemical compound CC1=CC=CC(N)=C1[N+]([O-])=O VDCZKCIEXGXCDJ-UHFFFAOYSA-N 0.000 description 2
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical class CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
IIZVERXSSGEDTK-UHFFFAOYSA-N 5-(2-fluorophenyl)-3-methylcyclohex-2-en-1-ol Chemical compound C1C(C)=CC(O)CC1C1=CC=CC=C1F IIZVERXSSGEDTK-UHFFFAOYSA-N 0.000 description 2
HFLMFOSJYVLCQL-UHFFFAOYSA-N 5-(2-fluorophenyl)-3-methylcyclohex-2-en-1-one Chemical compound C1C(C)=CC(=O)CC1C1=CC=CC=C1F HFLMFOSJYVLCQL-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
241000238876 Acari Species 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
241000532642 Conotrachelus nenuphar Species 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
206010061217 Infestation Diseases 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
241000258913 Oncopeltus fasciatus Species 0.000 description 2
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
241000219843 Pisum Species 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
241001454293 Tetranychus urticae Species 0.000 description 2
235000010749 Vicia faba Nutrition 0.000 description 2
241000607479 Yersinia pestis Species 0.000 description 2
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150000001342 alkaline earth metals Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
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244000309464 bull Species 0.000 description 1
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238000004587 chromatography analysis Methods 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
230000000332 continued effect Effects 0.000 description 1
GESZGOQOLBACSZ-UHFFFAOYSA-N copper(1+);1,2,3,4,5-pentafluorobenzene-6-ide Chemical compound [Cu+].FC1=[C-]C(F)=C(F)C(F)=C1F GESZGOQOLBACSZ-UHFFFAOYSA-N 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
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238000004090 dissolution Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
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239000000839 emulsion Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
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230000001747 exhibiting effect Effects 0.000 description 1
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239000003337 fertilizer Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
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230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
230000035784 germination Effects 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
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229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 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
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
QJOOIMSFFIUFKX-CAHLUQPWSA-N methyl (1s,3r)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)[C@H]1[C@H](C=C(Cl)Cl)C1(C)C QJOOIMSFFIUFKX-CAHLUQPWSA-N 0.000 description 1
ITNHSNMLIFFVQC-UHFFFAOYSA-N methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(C)C)C1(C)C ITNHSNMLIFFVQC-UHFFFAOYSA-N 0.000 description 1
NPXOIGSBRLCOSD-UHFFFAOYSA-N methyl 3-iodobenzoate Chemical compound COC(=O)C1=CC=CC(I)=C1 NPXOIGSBRLCOSD-UHFFFAOYSA-N 0.000 description 1
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000003415 peat Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000004262 preparative liquid chromatography Methods 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound 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
238000011084 recovery Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000005743 southern pea Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
235000001508 sulfur Nutrition 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
230000005945 translocation Effects 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
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000407132A 1980-10-02 1982-07-12 Derives de (1,1'-biphenyl)-3-ylmethyl comme produits intermediaires Expired CA1171874A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000407132A CA1171874A (fr)	1980-10-02	1982-07-12	Derives de (1,1'-biphenyl)-3-ylmethyl comme produits intermediaires

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US193,056		1980-10-02
US06/193,056 US4329518A (en)	1979-09-18	1980-10-02	Insecticidal [1,1'-biphenyl]-3-ylmethyl esters
US265,940		1981-05-21
US06/265,940 US4402973A (en)	1980-10-02	1981-05-21	Insecticidal (1,1'-biphenyl)-3-ylmethyl esters
CA386098		1981-09-17
CA000407132A CA1171874A (fr)	1980-10-02	1982-07-12	Derives de (1,1'-biphenyl)-3-ylmethyl comme produits intermediaires

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000407132A Division CA1171874A (fr)	1980-10-02	1982-07-12	Derives de (1,1'-biphenyl)-3-ylmethyl comme produits intermediaires

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000407132A Division CA1171874A (fr)	1980-10-02	1982-07-12	Derives de (1,1'-biphenyl)-3-ylmethyl comme produits intermediaires

Publications (1)

Publication Number	Publication Date
CA1171874A true CA1171874A (fr)	1984-07-31

Family

ID=27426331

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000407132A Expired CA1171874A (fr)	1980-10-02	1982-07-12	Derives de (1,1'-biphenyl)-3-ylmethyl comme produits intermediaires

Country Status (1)

Country	Link
CA (1)	CA1171874A (fr)

1982
- 1982-07-12 CA CA000407132A patent/CA1171874A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-08-01	MKEC	Expiry (correction)
2001-09-17	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20010917

Publication	Publication Date	Title
US4402973A (en)	1983-09-06	Insecticidal (1,1'-biphenyl)-3-ylmethyl esters
US4329518A (en)	1982-05-11	Insecticidal [1,1'-biphenyl]-3-ylmethyl esters
EP0020685B1 (fr)	1983-06-15	Cyclopropanecarboxylates insecticides a partir de composes de (1,1'-biphenyl)-3-ylmethyl substitues
EP0003336B1 (fr)	1984-02-22	Perhaloalcoylvinylcyclopropane carboxylates ayant une activité insecticide
US4332815A (en)	1982-06-01	Insecticidal perhaloalkylvinylcyclopropanecarboxylates
US4243677A (en)	1981-01-06	Insecticidal perhaloalkylvinylcyclopropanecarboxylates
US4339457A (en)	1982-07-13	3-(Pyrrol-1-yl)phenylmethyl esters and intermediates
JPS622574B2 (fr)	1987-01-20
US4536591A (en)	1985-08-20	Insecticidal [1,1'-biphenyl]-3-ylmethyl esters
US4200644A (en)	1980-04-29	Arylthiovinylcyclopropanecarboxylate insecticides
US4709068A (en)	1987-11-24	Substituted phenyltrialkylsilane insecticides
US4235927A (en)	1980-11-25	Insecticidal benzylfurylmethyl perhaloalkylvinylcyclopropanecarboxylates
JPS6136823B2 (fr)	1986-08-20
AU595796B2 (en)	1990-04-12	Novel carboxylic acid esters, methods for production thereof and insecticides containing them as the active ingredient
US4883789A (en)	1989-11-28	Substituted phenyltrialkylsilane insecticides
JPH0212941B2 (fr)	1990-03-30
US4346251A (en)	1982-08-24	4-Substituted-2-indanols
US4395567A (en)	1983-07-26	1R,Cis-3-(2-halo-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid derivatives
US4215069A (en)	1980-07-29	Arylthiovinylcyclopropanecarboxylate intermediates
US4408057A (en)	1983-10-04	4-Heterocyclic-substituted-2-indanyl alcohols and insecticidal ester derivatives
CA1179363A (fr)	1984-12-11	2-indanols-4-substitues et esters insecticides derives
US4442296A (en)	1984-04-10	4-Heterocyclic-substituted-2-indanyl alcohols and insecticidal ester derivatives
US4348326A (en)	1982-09-07	Substituted 7-oxabicyclo[2,2,1]hepta-2,5-diene methanols
EP0014593A1 (fr)	1980-08-20	Alcool bicyclique et esters insecticides en dérivant, leur préparation, compositions contenant les esters et méthodes insecticides les utilisant
IE50932B1 (en)	1986-08-20	Insecticidal ester derivatives of certain 4-substituted-2-indanols