HU199390B - Process for producing mixture of cipermetrin's enantiomeres - Google Patents

Process for producing mixture of cipermetrin's enantiomeres Download PDF

Info

Publication number: HU199390B
Authority: HU; Hungary
Prior art keywords: mixture; isomers; weight; trans; cis
Prior art date: 1989-01-17

Application number

HU16789A

Other languages

English (en)

Hungarian (hu)

Inventor

Bela Bertok

Antal Gajary

Agnes Hegedues

Istvan Lak

Sandor Botar

Janis Hajimichael

Gyoergy Hidasi

Andras Rapi

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1989-01-17

Filing date

1989-01-17

Publication date

1990-05-28

1989-01-17 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1989-01-17 Priority to GEAP19891407A priority Critical patent/GEP20002025B/en

1989-01-17 Priority to HU16789A priority patent/HU199390B/hu

1990-01-17 Priority to BR909004617A priority patent/BR9004617A/pt

1990-01-17 Priority to AT90901870T priority patent/ATE90338T1/de

1990-01-17 Priority to EP90901870A priority patent/EP0404922B1/en

1990-01-17 Priority to PCT/HU1990/000006 priority patent/WO1990008132A1/en

1990-01-17 Priority to SU904831010A priority patent/RU2051886C1/ru

1990-01-17 Priority to CA002020356A priority patent/CA2020356C/en

1990-01-17 Priority to US07/601,767 priority patent/US5153349A/en

1990-01-17 Priority to ES90901870T priority patent/ES2057531T3/es

1990-01-17 Priority to KR1019900702058A priority patent/KR940003358B1/ko

1990-01-17 Priority to DK90901870.7T priority patent/DK0404922T3/da

1990-01-17 Priority to DE9090901870T priority patent/DE69001866T2/de

1990-01-24 Priority to ZA90518A priority patent/ZA90518B/xx

1990-05-28 Publication of HU199390B publication Critical patent/HU199390B/hu

1993-06-15 Priority to LVP-93-589A priority patent/LV10233B/xx

1993-06-19 Priority to LVP-93-628A priority patent/LV10771B/en

1993-07-13 Priority to LTIP778A priority patent/LT3462B/lt

1993-07-13 Priority to LTIP786A priority patent/LT3464B/lt

1993-08-12 Priority to GEAP19931389A priority patent/GEP19981466B/en

1993-08-12 Priority to GEAP19931388A priority patent/GEP19981465B/en

1993-08-25 Priority to LTIP887A priority patent/LT3529B/lt

1994-08-25 Priority to MD94-0329A priority patent/MD282C2/ro

1994-08-25 Priority to MD94-0335A priority patent/MD500G2/ro

Links

239000000203 mixture Substances 0.000 title claims abstract description 69
238000000034 method Methods 0.000 title claims description 28
230000008569 process Effects 0.000 title claims description 15
KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims abstract description 38
229910052799 carbon Inorganic materials 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 46
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 39
239000005946 Cypermethrin Substances 0.000 claims description 33
229960005424 cypermethrin Drugs 0.000 claims description 33
238000002360 preparation method Methods 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 18
230000009466 transformation Effects 0.000 claims description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
239000007858 starting material Substances 0.000 claims description 8
239000000463 material Substances 0.000 claims description 7
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 claims description 7
239000007787 solid Substances 0.000 claims description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
238000001816 cooling Methods 0.000 claims description 3
239000012535 impurity Substances 0.000 claims description 3
239000003208 petroleum Substances 0.000 claims description 3
239000002728 pyrethroid Substances 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
238000005406 washing Methods 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
235000005985 organic acids Nutrition 0.000 claims description 2
HYNDYAQJODYUGF-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1NCCCN2CCCC=C21 HYNDYAQJODYUGF-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
230000035484 reaction time Effects 0.000 claims 1
230000017105 transposition Effects 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 2
239000002253 acid Substances 0.000 abstract 2
239000003381 stabilizer Substances 0.000 abstract 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 abstract 1
150000001735 carboxylic acids Chemical class 0.000 abstract 1
239000001530 fumaric acid Substances 0.000 abstract 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
239000011976 maleic acid Substances 0.000 abstract 1
235000006408 oxalic acid Nutrition 0.000 abstract 1
239000013078 crystal Substances 0.000 description 9
238000002425 crystallisation Methods 0.000 description 9
230000008025 crystallization Effects 0.000 description 9
239000000047 product Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000000243 solution Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
238000006345 epimerization reaction Methods 0.000 description 4
239000002002 slurry Substances 0.000 description 4
KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 3
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
KAATUXNTWXVJKI-FLXSOZOKSA-N [(S)-cyano-(3-phenoxyphenyl)methyl] (1R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-FLXSOZOKSA-N 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
239000005877 Alpha-Cypermethrin Substances 0.000 description 2
239000002178 crystalline material Substances 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000008719 thickening Effects 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
IOCYQQQCJYMWDT-UHFFFAOYSA-N (3-ethyl-2-methoxyquinolin-6-yl)-(4-methoxycyclohexyl)methanone Chemical compound C=1C=C2N=C(OC)C(CC)=CC2=CC=1C(=O)C1CCC(OC)CC1 IOCYQQQCJYMWDT-UHFFFAOYSA-N 0.000 description 1
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
241000238421 Arthropoda Species 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
230000008901 benefit Effects 0.000 description 1
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
230000008859 change Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000004927 fusion Effects 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
231100001225 mammalian toxicity Toxicity 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
235000013849 propane Nutrition 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000000844 transformation Methods 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Landscapes

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

HU16789A 1989-01-17 1989-01-17 Process for producing mixture of cipermetrin's enantiomeres HU199390B (en)

Priority Applications (23)

Application Number	Priority Date	Filing Date	Title
GEAP19891407A GEP20002025B (en)	1989-01-17	1989-01-17	The Stable Arthropodicidal Composition
HU16789A HU199390B (en)	1989-01-17	1989-01-17	Process for producing mixture of cipermetrin's enantiomeres
DK90901870.7T DK0404922T3 (da)	1989-01-17	1990-01-17	Fremgangsmåde til fremstilling af cypermethrin-isomerer
AT90901870T ATE90338T1 (de)	1989-01-17	1990-01-17	Verfahren zur herstellung von cypermethrinisomeren.
EP90901870A EP0404922B1 (en)	1989-01-17	1990-01-17	Process for the preparation of cypermethrine isomers
PCT/HU1990/000006 WO1990008132A1 (en)	1989-01-17	1990-01-17	Process for the preparation of cypermethrine isomers
SU904831010A RU2051886C1 (ru)	1989-01-17	1990-01-17	Способ получения смеси изомеров циперметрина в форме стабилизированного кристаллического продукта
CA002020356A CA2020356C (en)	1989-01-17	1990-01-17	Process for the preparation of cypermethrine isomers
US07/601,767 US5153349A (en)	1989-01-17	1990-01-17	Process for the preparation of cypermethrine isomers
ES90901870T ES2057531T3 (es)	1989-01-17	1990-01-17	Procedimiento para la preparacion de isomeros de cipermetrina.
KR1019900702058A KR940003358B1 (ko)	1989-01-17	1990-01-17	사이퍼메트린 이성체 혼합물의 제조방법
BR909004617A BR9004617A (pt)	1989-01-17	1990-01-17	Processo para a preparacao de isomeros de cipermetrina
DE9090901870T DE69001866T2 (de)	1989-01-17	1990-01-17	Verfahren zur herstellung von cypermethrin-isomeren.
ZA90518A ZA90518B (en)	1989-01-17	1990-01-24	Process for the preparation of cypermethrine isomers
LVP-93-589A LV10233B (en)	1989-01-17	1993-06-15	Stable arthropodal composition
LVP-93-628A LV10771B (en)	1989-01-17	1993-06-19	Process for the preparation of cypermetrine isomers
LTIP778A LT3462B (en)	1989-01-17	1993-07-13	Process for preparation of cypermethrine isomers
LTIP786A LT3464B (en)	1989-01-17	1993-07-13	Stable arthropodical composition
GEAP19931389A GEP19981466B (en)	1989-01-17	1993-08-12	Process for the preparation of cypermethrine isomers
GEAP19931388A GEP19981465B (en)	1989-01-17	1993-08-12	Process for the preparation of cypermethrine isomers
LTIP887A LT3529B (en)	1989-01-17	1993-08-25	Process for preparation of cypermethrine isomers
MD94-0329A MD282C2 (ro)	1989-01-17	1994-08-25	Procedeu de preparare a amestecului de izomeri ai zipermetrinei sub formă de produs cristalin stabilizat
MD94-0335A MD500G2 (ro)	1989-01-17	1994-08-25	Compoziţie artropodicală stabilă

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU16789A HU199390B (en)	1989-01-17	1989-01-17	Process for producing mixture of cipermetrin's enantiomeres

Publications (1)

Publication Number	Publication Date
HU199390B true HU199390B (en)	1990-05-28

Family

ID=10948282

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU16789A HU199390B (en)	1989-01-17	1989-01-17	Process for producing mixture of cipermetrin's enantiomeres

Country Status (7)

Country	Link
GE (1)	GEP20002025B (lt)
HU (1)	HU199390B (lt)
LT (3)	LT3464B (lt)
LV (1)	LV10233B (lt)
MD (1)	MD500G2 (lt)
RU (1)	RU2051886C1 (lt)
ZA (1)	ZA90518B (lt)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1162561A (en)	1981-05-26	1984-02-21	Derek A. Wood	Preparation of cyanobenzyl cyclopropane carboxylates
CA1206483A (en)	1982-11-11	1986-06-24	Johannes Van Berkel	Process for preparing cyclopropane carboxylic acid ester derivatives
CA1275108A (en) *	1985-01-16	1990-10-09	Laszlo Pap	Insecticidal composition comprising more than one active ingredients
US4751634A (en)	1985-06-14	1988-06-14	International Business Machines Corporation	Multiple port communications adapter apparatus
CA1314559C (en)	1987-06-15	1993-03-16	John Winfrid Ager	Conversion of pyrethroid isomers to more active species

1989
- 1989-01-17 GE GEAP19891407A patent/GEP20002025B/en unknown
- 1989-01-17 HU HU16789A patent/HU199390B/hu not_active IP Right Cessation
1990
- 1990-01-17 RU SU904831010A patent/RU2051886C1/ru not_active IP Right Cessation
- 1990-01-24 ZA ZA90518A patent/ZA90518B/xx unknown
1993
- 1993-06-15 LV LVP-93-589A patent/LV10233B/xx unknown
- 1993-07-13 LT LTIP786A patent/LT3464B/lt not_active IP Right Cessation
- 1993-07-13 LT LTIP778A patent/LT3462B/lt not_active IP Right Cessation
- 1993-08-25 LT LTIP887A patent/LT3529B/lt unknown
1994
- 1994-08-25 MD MD94-0335A patent/MD500G2/ro not_active IP Right Cessation

Also Published As

Publication number	Publication date
LV10233B (en)	1995-04-20
MD500G2 (ro)	1996-11-30
ZA90518B (en)	1991-12-24
LT3464B (en)	1995-10-25
LV10233A (lv)	1994-10-20
LTIP778A (en)	1995-01-31
LTIP786A (en)	1995-01-31
LT3529B (en)	1995-11-27
RU2051886C1 (ru)	1996-01-10
GEP20002025B (en)	2000-04-10
LTIP887A (en)	1995-03-27
LT3462B (en)	1995-10-25
MD500F1 (en)	1996-03-29

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628
2000-04-28	HPC4	Succession in title of patentee	Owner name: AGRO-CHEMIE NOVENYVEDOESZER GYARTO, ERTEKESITOE ES
2006-10-30	MM4A	Lapse of definitive patent protection due to non-payment of fees

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US2736728A (en)	1956-02-28	Preparation of lysergic acid amides
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EP0029175B1 (de)	1982-12-15	Verfahren zur Gewinnung der enantiomeren Formen von 4-Cyan-1-(N-methyl-N-(2'-((3",4"-dimethoxyphenyl))-ethyl)-amino)-5-methyl-4-(3',4',5'-trimethoxyphenyl)-hexan und dessen Salzen
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FR2481274A1 (fr)	1981-10-30	Procede de preparation de derives esters d'acides cyclopropane-carboxyliques
US4436667A (en)	1984-03-13	Process for preparing cyclopropane carboxylic acid ester derivatives
US4439611A (en)	1984-03-27	Isolation of [S-(R, S]-1-(3-acetylthio-3-benzoyl-2-methylpropionyl)-L-proline from a diastereomeric mixture
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GB2075011A (en)	1981-11-11	Process for Preparing Cyclopropane Carboxylic Acid Ester Derivatives
US5128497A (en)	1992-07-07	Conversion of pyrethroid isomers to more active species
KR20020038689A (ko)	2002-05-23	Ｎ-(1(ｓ)-에톡시카르보닐-3-페닐프로필)-ｌ-알라닌ｎ-카르복시무수물의 결정화 방법
US4709082A (en)	1987-11-24	2-phenylpropionic acid esters, method for optical resolution thereof and optically active substance thereof
US3031443A (en)	1962-04-24	Process for preparing a 3-nitro-azacycloalkanone-2-nu-carbochloride
RU2045516C1 (ru)	1995-10-10	Способ получения смесей изомеров циперметрина
KR20010071161A (ko)	2001-07-28	Ｎ-(1-시아노알킬)-2-페녹시프로피온아미드 유도체의개선된 제조 방법
EP0404922B1 (en)	1993-06-09	Process for the preparation of cypermethrine isomers
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