CS246054B2 - Method of alpha-cyanogen-3-phenoxybenzyl-2-(4-chlorophenyl)isovalerate production - Google Patents

Method of alpha-cyanogen-3-phenoxybenzyl-2-(4-chlorophenyl)isovalerate production Download PDF

Info

Publication number: CS246054B2
Authority: CS; Czechoslovakia
Prior art keywords: crystals; pair; enantiomeric; enantiomeric pair; chlorophenyl
Prior art date: 1981-03-16

Application number

CS821749A

Other languages

Czech (cs)

English (en)

Inventor

Walter L Petty

Original Assignee

Shell Int Research

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.)

1981-03-16

Filing date

1982-03-15

Publication date

1986-10-16

1982-03-15 Application filed by Shell Int Research filed Critical Shell Int Research

1986-10-16 Publication of CS246054B2 publication Critical patent/CS246054B2/cs

Links

238000000034 method Methods 0.000 title claims description 20
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 title claims description 8
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title description 2
239000013078 crystal Substances 0.000 claims abstract description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 46
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
238000002425 crystallisation Methods 0.000 claims description 13
230000008025 crystallization Effects 0.000 claims description 13
239000000243 solution Substances 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 7
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
229910021529 ammonia Inorganic materials 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 4
239000012047 saturated solution Substances 0.000 claims description 3
YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 claims 1
239000003637 basic solution Substances 0.000 claims 1
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 abstract description 11
229940049953 phenylacetate Drugs 0.000 abstract description 11
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract description 11
239000000706 filtrate Substances 0.000 abstract description 8
230000000361 pesticidal effect Effects 0.000 abstract description 2
230000001376 precipitating effect Effects 0.000 abstract 1
NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 51
239000000203 mixture Substances 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000004817 gas chromatography Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002585 base Substances 0.000 description 6
150000001412 amines Chemical class 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
229920001429 chelating resin Polymers 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
-1 alkaline earth metal salts Chemical class 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
238000006345 epimerization reaction Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
229920001467 poly(styrenesulfonates) Polymers 0.000 description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
229920002125 Sokalan® Polymers 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000003456 ion exchange resin Substances 0.000 description 3
229920003303 ion-exchange polymer Polymers 0.000 description 3
239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-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
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
238000010924 continuous production Methods 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
125000001477 organic nitrogen group Chemical group 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
GRKBGVAQZZZEJW-UHFFFAOYSA-N 2-cyano-2,3-diphenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)(C#N)CC1=CC=CC=C1 GRKBGVAQZZZEJW-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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 1
OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000284708 Sarcophaga alpha Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000003973 alkyl amines Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
238000010908 decantation Methods 0.000 description 1
239000012972 dimethylethanolamine Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
229960002179 ephedrine Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
GMDNUWQNDQDBNQ-UHFFFAOYSA-L magnesium;diformate Chemical compound [Mg+2].[O-]C=O.[O-]C=O GMDNUWQNDQDBNQ-UHFFFAOYSA-L 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000002667 nucleating agent Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CS821749A 1981-03-16 1982-03-15 Method of alpha-cyanogen-3-phenoxybenzyl-2-(4-chlorophenyl)isovalerate production CS246054B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/244,372 US4350642A (en)	1981-03-16	1981-03-16	Process for preparation of a pesticidal phenylacetate enantiomer pair

Publications (1)

Publication Number	Publication Date
CS246054B2 true CS246054B2 (en)	1986-10-16

Family

ID=22922456

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS821749A CS246054B2 (en)	1981-03-16	1982-03-15	Method of alpha-cyanogen-3-phenoxybenzyl-2-(4-chlorophenyl)isovalerate production

Country Status (33)

Country	Link
US (1)	US4350642A (ro)
EP (1)	EP0060580B1 (ro)
JP (1)	JPS57159754A (ro)
KR (1)	KR890000366B1 (ro)
AR (1)	AR228971A1 (ro)
AT (1)	ATE13660T1 (ro)
AU (1)	AU552864B2 (ro)
BG (1)	BG42002A3 (ro)
BR (1)	BR8201406A (ro)
CA (1)	CA1231718A (ro)
CS (1)	CS246054B2 (ro)
CU (1)	CU21440A3 (ro)
DD (1)	DD202005A5 (ro)
DE (1)	DE3263981D1 (ro)
DK (1)	DK169539B1 (ro)
EG (1)	EG17022A (ro)
ES (1)	ES510428A0 (ro)
FI (1)	FI76549C (ro)
GR (1)	GR76069B (ro)
HU (1)	HU186485B (ro)
IE (1)	IE52811B1 (ro)
IL (1)	IL65249A0 (ro)
IN (1)	IN157710B (ro)
NO (1)	NO152557C (ro)
NZ (1)	NZ200015A (ro)
OA (1)	OA07040A (ro)
PH (1)	PH17588A (ro)
PL (1)	PL139390B1 (ro)
PT (1)	PT74583B (ro)
RO (1)	RO84322B (ro)
TR (1)	TR21228A (ro)
YU (1)	YU43790B (ro)
ZA (1)	ZA821712B (ro)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS54103831A (en) *	1978-01-27	1979-08-15	Sumitomo Chem Co Ltd	Separation of stereoisomers of higher active cyanoo33 phenoxybenzyl 2244chlorophenyl*isovalerate
US4176195A (en) *	1978-07-20	1979-11-27	Sumitomo Chemical Company, Limited	Pesticidal α-cyanobenzyl ester enantiomer pair
JPS55104253A (en) *	1979-02-06	1980-08-09	Sumitomo Chem Co Ltd	Stereoisomer of more active carboxylic ester, method of obtaining it, insecticide and acaricide comprising it
JPS56167654A (en) *	1980-05-28	1981-12-23	Sumitomo Chem Co Ltd	Method for obtaining stereoisomeric mixture of more highly active phenylacetic ester derivative

1981
- 1981-03-16 US US06/244,372 patent/US4350642A/en not_active Expired - Fee Related
1982
- 1982-02-08 DK DK053182A patent/DK169539B1/da not_active IP Right Cessation
- 1982-02-09 IN IN103/DEL/82A patent/IN157710B/en unknown
- 1982-02-12 CA CA000396198A patent/CA1231718A/en not_active Expired
- 1982-02-24 DE DE8282200227T patent/DE3263981D1/de not_active Expired
- 1982-02-24 AT AT82200227T patent/ATE13660T1/de not_active IP Right Cessation
- 1982-02-24 EP EP82200227A patent/EP0060580B1/en not_active Expired
- 1982-03-12 AR AR288732A patent/AR228971A1/es active
- 1982-03-13 KR KR8201075A patent/KR890000366B1/ko not_active Expired
- 1982-03-15 GR GR67594A patent/GR76069B/el unknown
- 1982-03-15 CU CU35609A patent/CU21440A3/es unknown
- 1982-03-15 OA OA57635A patent/OA07040A/xx unknown
- 1982-03-15 TR TR21228A patent/TR21228A/xx unknown
- 1982-03-15 AU AU81532/82A patent/AU552864B2/en not_active Ceased
- 1982-03-15 EG EG132/82A patent/EG17022A/xx active
- 1982-03-15 JP JP57039595A patent/JPS57159754A/ja active Granted
- 1982-03-15 HU HU82782A patent/HU186485B/hu not_active IP Right Cessation
- 1982-03-15 FI FI820879A patent/FI76549C/fi not_active IP Right Cessation
- 1982-03-15 CS CS821749A patent/CS246054B2/cs unknown
- 1982-03-15 PH PH26988A patent/PH17588A/en unknown
- 1982-03-15 NZ NZ200015A patent/NZ200015A/en unknown
- 1982-03-15 DD DD82238160A patent/DD202005A5/de not_active IP Right Cessation
- 1982-03-15 ES ES510428A patent/ES510428A0/es active Granted
- 1982-03-15 YU YU565/82A patent/YU43790B/xx unknown
- 1982-03-15 BG BG055781A patent/BG42002A3/xx unknown
- 1982-03-15 IE IE588/82A patent/IE52811B1/en not_active IP Right Cessation
- 1982-03-15 RO RO106912A patent/RO84322B/ro unknown
- 1982-03-15 IL IL65249A patent/IL65249A0/xx not_active IP Right Cessation
- 1982-03-15 ZA ZA821712A patent/ZA821712B/xx unknown
- 1982-03-15 BR BR8201406A patent/BR8201406A/pt not_active IP Right Cessation
- 1982-03-15 NO NO820834A patent/NO152557C/no unknown
- 1982-03-15 PT PT74583A patent/PT74583B/pt not_active IP Right Cessation
- 1982-03-15 PL PL1982235454A patent/PL139390B1/pl unknown

Also Published As

Publication number	Publication date
PT74583B (en)	1983-11-07
EP0060580A1 (en)	1982-09-22
US4350642A (en)	1982-09-21
NO820834L (no)	1982-09-17
AU8153282A (en)	1982-09-23
ES8305704A1 (es)	1983-04-16
IL65249A0 (en)	1982-05-31
NZ200015A (en)	1985-08-16
NO152557C (no)	1985-10-16
FI76549C (fi)	1988-11-10
FI76549B (fi)	1988-07-29
RO84322A (ro)	1984-08-17
BR8201406A (pt)	1983-02-01
EG17022A (en)	1989-03-30
PH17588A (en)	1984-10-02
KR890000366B1 (ko)	1989-03-14
JPH036135B2 (ro)	1991-01-29
HU186485B (en)	1985-08-28
ZA821712B (en)	1983-01-26
IN157710B (ro)	1986-05-24
DD202005A5 (de)	1983-08-24
YU56582A (en)	1985-04-30
RO84322B (ro)	1984-09-30
AU552864B2 (en)	1986-06-26
ES510428A0 (es)	1983-04-16
TR21228A (tr)	1984-02-02
AR228971A1 (es)	1983-05-13
JPS57159754A (en)	1982-10-01
EP0060580B1 (en)	1985-06-05
BG42002A3 (en)	1987-09-15
KR830009007A (ko)	1983-12-17
PT74583A (en)	1982-04-01
ATE13660T1 (de)	1985-06-15
CU21440A3 (es)	1991-07-15
FI820879L (fi)	1982-09-17
GR76069B (ro)	1984-08-03
YU43790B (en)	1989-12-31
NO152557B (no)	1985-07-08
PL139390B1 (en)	1987-01-31
IE820588L (en)	1982-09-16
DK169539B1 (da)	1994-11-28
DE3263981D1 (en)	1985-07-11
OA07040A (fr)	1983-12-31
PL235454A1 (ro)	1982-09-27
IE52811B1 (en)	1988-03-16
DK53182A (da)	1982-09-20
CA1231718A (en)	1988-01-19

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