SK99594A3 - Method of preparation of phenoxyphenoalkyl derivatives - Google Patents

Method of preparation of phenoxyphenoalkyl derivatives Download PDF

Info

Publication number: SK99594A3
Authority: SK; Slovakia
Prior art keywords: compound; formula; reaction; mixture; isomer
Prior art date: 1993-08-23

Application number

SK995-94A

Other languages

English (en)

Slovak (sk)

Inventor

Michael Barz

Friedrich Karrer

Original Assignee

Ciba Geigy Ag

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.)

1993-08-23

Filing date

1994-08-22

Publication date

1995-07-11

1994-08-22 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1995-07-11 Publication of SK99594A3 publication Critical patent/SK99594A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 195
238000002360 preparation method Methods 0.000 title claims description 23
150000001875 compounds Chemical class 0.000 claims abstract description 214
239000000203 mixture Substances 0.000 claims abstract description 166
230000008569 process Effects 0.000 claims abstract description 147
238000006243 chemical reaction Methods 0.000 claims abstract description 83
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 78
239000004480 active ingredient Substances 0.000 claims abstract description 36
239000000376 reactant Substances 0.000 claims abstract description 23
241000607479 Yersinia pestis Species 0.000 claims abstract description 22
239000003377 acid catalyst Substances 0.000 claims abstract description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
ZDOOQPFIGYHZFV-UHFFFAOYSA-N 2-ethyl-4-[(4-phenoxyphenoxy)methyl]-1,3-dioxolane Chemical compound O1C(CC)OCC1COC(C=C1)=CC=C1OC1=CC=CC=C1 ZDOOQPFIGYHZFV-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052740 iodine Inorganic materials 0.000 claims abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 63
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 44
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 32
239000011541 reaction mixture Substances 0.000 claims description 32
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 32
-1 benzenesulfonyloxy, toluenesulfonyloxy Chemical group 0.000 claims description 28
229910000027 potassium carbonate Inorganic materials 0.000 claims description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 19
239000002585 base Substances 0.000 claims description 19
239000008096 xylene Substances 0.000 claims description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
238000010533 azeotropic distillation Methods 0.000 claims description 12
239000003701 inert diluent Substances 0.000 claims description 12
239000012442 inert solvent Substances 0.000 claims description 12
239000000463 material Substances 0.000 claims description 12
230000035484 reaction time Effects 0.000 claims description 12
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
238000004821 distillation Methods 0.000 claims description 10
241000238631 Hexapoda Species 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
230000006378 damage Effects 0.000 claims description 7
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 7
241000238876 Acari Species 0.000 claims description 6
238000002955 isolation Methods 0.000 claims description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
150000003973 alkyl amines Chemical class 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000012065 filter cake Substances 0.000 claims description 5
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 4
150000004703 alkoxides Chemical class 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229940098779 methanesulfonic acid Drugs 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
150000003460 sulfonic acids Chemical class 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
239000002841 Lewis acid Substances 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 3
239000004927 clay Substances 0.000 claims description 3
239000003456 ion exchange resin Substances 0.000 claims description 3
229920003303 ion-exchange polymer Polymers 0.000 claims description 3
150000007517 lewis acids Chemical class 0.000 claims description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
230000009471 action Effects 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
125000004995 haloalkylthio group Chemical group 0.000 claims description 2
150000004678 hydrides Chemical class 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
235000013311 vegetables Nutrition 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims 3
OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 claims 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
150000002391 heterocyclic compounds Chemical class 0.000 claims 2
230000000361 pesticidal effect Effects 0.000 claims 2
FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
239000000908 ammonium hydroxide Substances 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000005265 dialkylamine group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 10
239000012074 organic phase Substances 0.000 description 50
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000008346 aqueous phase Substances 0.000 description 26
239000000047 product Substances 0.000 description 26
241000196324 Embryophyta Species 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
230000008901 benefit Effects 0.000 description 21
239000000243 solution Substances 0.000 description 21
239000000725 suspension Substances 0.000 description 21
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 20
239000013543 active substance Substances 0.000 description 19
ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 18
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 15
239000003921 oil Substances 0.000 description 15
235000019198 oils Nutrition 0.000 description 15
239000007858 starting material Substances 0.000 description 15
238000009835 boiling Methods 0.000 description 14
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
239000007787 solid Substances 0.000 description 13
239000004094 surface-active agent Substances 0.000 description 13
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 12
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
230000000694 effects Effects 0.000 description 11
239000000843 powder Substances 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
238000001816 cooling Methods 0.000 description 10
239000013078 crystal Substances 0.000 description 10
238000002425 crystallisation Methods 0.000 description 10
230000008025 crystallization Effects 0.000 description 10
235000013601 eggs Nutrition 0.000 description 10
239000000839 emulsion Substances 0.000 description 10
239000005909 Kieselgur Substances 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 8
239000005995 Aluminium silicate Substances 0.000 description 8
235000012211 aluminium silicate Nutrition 0.000 description 8
235000013399 edible fruits Nutrition 0.000 description 8
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 8
238000012360 testing method Methods 0.000 description 8
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
238000009472 formulation Methods 0.000 description 7
239000008187 granular material Substances 0.000 description 7
238000006116 polymerization reaction Methods 0.000 description 7
239000000126 substance Substances 0.000 description 7
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
240000007594 Oryza sativa Species 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
239000000969 carrier Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
235000013339 cereals Nutrition 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
235000014113 dietary fatty acids Nutrition 0.000 description 6
230000007613 environmental effect Effects 0.000 description 6
239000000194 fatty acid Substances 0.000 description 6
229930195729 fatty acid Natural products 0.000 description 6
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
241001556089 Nilaparvata lugens Species 0.000 description 5
239000000654 additive Substances 0.000 description 5
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
239000007788 liquid Substances 0.000 description 5
230000009467 reduction Effects 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
239000004593 Epoxy Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 4
235000007164 Oryza sativa Nutrition 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
150000004649 carbonic acid derivatives Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
235000008504 concentrate Nutrition 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 4
150000008282 halocarbons Chemical class 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
239000000575 pesticide Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
235000009566 rice Nutrition 0.000 description 4
239000004546 suspension concentrate Substances 0.000 description 4
239000012085 test solution Substances 0.000 description 4
FYPUKRQAGKRSOW-UHFFFAOYSA-N 3-(4-phenoxyphenoxy)propane-1,2-diol Chemical compound C1=CC(OCC(O)CO)=CC=C1OC1=CC=CC=C1 FYPUKRQAGKRSOW-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
241001635274 Cydia pomonella Species 0.000 description 3
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 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
235000002595 Solanum tuberosum Nutrition 0.000 description 3
244000061456 Solanum tuberosum Species 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000003905 agrochemical Substances 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
235000019438 castor oil Nutrition 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003240 coconut oil Substances 0.000 description 3
235000019864 coconut oil Nutrition 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000005265 energy consumption Methods 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
238000000227 grinding Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
230000036541 health Effects 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000002736 nonionic surfactant Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229920005552 sodium lignosulfonate Polymers 0.000 description 3
238000003860 storage Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
241001414827 Aonidiella Species 0.000 description 2
241001414828 Aonidiella aurantii Species 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
235000016068 Berberis vulgaris Nutrition 0.000 description 2
241000335053 Beta vulgaris Species 0.000 description 2
229910021532 Calcite Inorganic materials 0.000 description 2
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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
- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified

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Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

SK995-94A 1993-08-23 1994-08-22 Method of preparation of phenoxyphenoalkyl derivatives SK99594A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH250393		1993-08-23

Publications (1)

Publication Number	Publication Date
SK99594A3 true SK99594A3 (en)	1995-07-11

Family

ID=4235274

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK995-94A SK99594A3 (en)	1993-08-23	1994-08-22	Method of preparation of phenoxyphenoalkyl derivatives

Country Status (14)

Country	Link
EP (1)	EP0643053A1 (cs)
JP (1)	JPH0782201A (cs)
KR (1)	KR950005790A (cs)
CN (1)	CN1101347A (cs)
AU (1)	AU7141194A (cs)
BR (1)	BR9403304A (cs)
CA (1)	CA2130503A1 (cs)
CZ (1)	CZ202694A3 (cs)
HU (1)	HUT68688A (cs)
IL (1)	IL110662A0 (cs)
NZ (1)	NZ264273A (cs)
RU (1)	RU94030237A (cs)
SK (1)	SK99594A3 (cs)
ZA (1)	ZA946358B (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN104876905A (zh) *	2014-02-27	2015-09-02	上海生华化学科技有限公司	一种含苯氧基苯氧甲基结构的1,3-二氧戊环类化合物的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4097581A (en) *	1975-12-12	1978-06-27	Ciba-Geigy Corporation	Dioxolane derivatives
DE59206884D1 (de) *	1991-02-25	1996-09-19	Ciba Geigy Ag	Methyldioxolan
DK0551796T3 (da) *	1992-01-03	1998-03-23	Ciba Geigy Ag	Suspension af mikrokapsler og fremgangsmåde til dens fremstiling
CH685090A5 (de) *	1992-08-25	1995-03-31	Ciba Geigy Ag	Verfahren zur Bekämpfung von Insekten.

1994
- 1994-08-15 IL IL11066294A patent/IL110662A0/xx unknown
- 1994-08-16 EP EP94810470A patent/EP0643053A1/en not_active Withdrawn
- 1994-08-19 NZ NZ264273A patent/NZ264273A/en unknown
- 1994-08-19 CA CA002130503A patent/CA2130503A1/en not_active Abandoned
- 1994-08-22 CN CN94115766A patent/CN1101347A/zh active Pending
- 1994-08-22 BR BR9403304A patent/BR9403304A/pt not_active Application Discontinuation
- 1994-08-22 ZA ZA946358A patent/ZA946358B/xx unknown
- 1994-08-22 HU HU9402423A patent/HUT68688A/hu unknown
- 1994-08-22 CZ CZ942026A patent/CZ202694A3/cs unknown
- 1994-08-22 SK SK995-94A patent/SK99594A3/sk unknown
- 1994-08-22 AU AU71411/94A patent/AU7141194A/en not_active Abandoned
- 1994-08-23 KR KR1019940020996A patent/KR950005790A/ko not_active Withdrawn
- 1994-08-23 RU RU94030237/04A patent/RU94030237A/ru unknown
- 1994-08-23 JP JP6220995A patent/JPH0782201A/ja active Pending

Also Published As

Publication number	Publication date
EP0643053A1 (en)	1995-03-15
RU94030237A (ru)	1996-06-20
KR950005790A (ko)	1995-03-20
IL110662A0 (en)	1994-11-11
HUT68688A (en)	1995-07-28
HU9402423D0 (en)	1994-11-28
CA2130503A1 (en)	1995-02-24
BR9403304A (pt)	1995-04-11
NZ264273A (en)	1996-08-27
CZ202694A3 (en)	1995-03-15
JPH0782201A (ja)	1995-03-28
ZA946358B (en)	1995-02-23
CN1101347A (zh)	1995-04-12
AU7141194A (en)	1995-03-02

Publication	Publication Date	Title
US5852012A (en)	1998-12-22	Oxadiazine derivatives
US6022871A (en)	2000-02-08	Oxadiazine derivatives
WO1995009151A1 (en)	1995-04-06	Acylated sulphonamides as insecticides and acaricides
PL185913B1 (pl)	2003-08-29	Pochodne strobiluryny, sposób wytwarzania pochodnyPochodne strobiluryny, sposób wytwarzania pochodnych strobiluryny, związki pośrednie, sposób wytwarzch strobiluryny, związki pośrednie, sposób wytwarzania związków pośrednich, kompozycja pestycydowa oania związków pośrednich, kompozycja pestycydowa oraz zastosowanie pochodnych strobilurynyraz zastosowanie pochodnych strobiluryny
US6306798B1 (en)	2001-10-23	Compounds for controlling insects and representatives of the order acarina
EP0661289A1 (en)	1995-07-05	Vinyl carboxamide derivatives as insecticides and acaricides
US5663453A (en)	1997-09-02	Dioxolane derivatives
US5393885A (en)	1995-02-28	Carbamic acid derivatives
EP0604365B1 (en)	1999-05-26	Imidazole derivatives and their use as agrochemical agents
SK99594A3 (en)	1995-07-11	Method of preparation of phenoxyphenoalkyl derivatives
US5077304A (en)	1991-12-31	Aminopyridines
WO1996004284A1 (en)	1996-02-15	Insecticidal polycyclic compounds
US5663379A (en)	1997-09-02	Substituted phenyl ethers
KR0172940B1 (ko)	1999-03-30	에틸 2-[4-(3-클로로페녹시)페녹시]에틸카르바메이트, 그의 제조방법 및 이를 함유하는 조성물
ES2162633T5 (es)	2007-07-01	Pesticidas.
WO1995029889A1 (en)	1995-11-09	Perhaloalkoxybenzenophenone hydrazones and their use as pesticides
CA2015435A1 (en)	1990-10-27	Bisacylethylamines
US5192803A (en)	1993-03-09	Sulfenylated carbamic esters and their use in pesticides
MXPA96005193A (en)	1998-07-03	Hydrazones of perhaloxco-benzenophenones and their use as plagicide
IE913652A1 (en)	1992-04-22	Diphenyl ethers