IL112433A - Combined compounds of 1,1-bis) 4-chlorophenyl (-2,2,2-trichloroethanol and a process for their preparation, and their use in controlling plant mites - Google Patents

Combined compounds of 1,1-bis) 4-chlorophenyl (-2,2,2-trichloroethanol and a process for their preparation, and their use in controlling plant mites

Info

Publication number: IL112433A
Authority: IL; Israel
Prior art keywords: chlorophenyl; compound; dicofol; bis; trichloroethanol
Prior art date: 1989-07-18

Application number

IL11243390A

Other languages

English (en)

Hebrew (he)

Original Assignee

Desarrollos Quimicos S A Soc E

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.)

1989-07-18

Filing date

1990-07-17

Publication date

1996-10-16

1989-07-18 Priority claimed from ES8902527A external-priority patent/ES2013962A6/es

1990-06-27 Priority claimed from ES9001766A external-priority patent/ES2032243B1/es

1990-07-17 Application filed by Desarrollos Quimicos S A Soc E filed Critical Desarrollos Quimicos S A Soc E

1996-10-16 Publication of IL112433A publication Critical patent/IL112433A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 73
UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 title claims abstract description 70
238000000034 method Methods 0.000 title claims abstract description 33
238000002360 preparation method Methods 0.000 title claims description 11
241000238876 Acari Species 0.000 title claims description 5
229960001760 dimethyl sulfoxide Drugs 0.000 claims abstract description 20
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 8
150000002576 ketones Chemical class 0.000 claims abstract description 8
239000000126 substance Substances 0.000 claims abstract description 8
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 62
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 30
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
238000001816 cooling Methods 0.000 claims description 15
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 13
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 12
-1 cycloalkyl ethers Chemical class 0.000 claims description 10
238000001914 filtration Methods 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
239000008096 xylene Substances 0.000 claims description 7
150000001735 carboxylic acids Chemical class 0.000 claims description 6
238000005406 washing Methods 0.000 claims description 6
CVUGPAFCQJIYDT-UHFFFAOYSA-N 1-chloro-2-[2,2,2-trichloro-1-(4-chlorophenyl)ethyl]benzene Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=CC=C1Cl CVUGPAFCQJIYDT-UHFFFAOYSA-N 0.000 claims description 4
239000005864 Sulphur Substances 0.000 claims description 4
238000002425 crystallisation Methods 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
150000007824 aliphatic compounds Chemical class 0.000 claims description 3
150000001491 aromatic compounds Chemical group 0.000 claims description 3
125000000524 functional group Chemical group 0.000 claims description 3
150000003462 sulfoxides Chemical class 0.000 claims description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 2
150000008282 halocarbons Chemical class 0.000 claims 2
125000006413 ring segment Chemical group 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims 1
150000001983 dialkylethers Chemical class 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 28
238000011084 recovery Methods 0.000 description 17
238000003756 stirring Methods 0.000 description 16
239000000047 product Substances 0.000 description 15
238000004821 distillation Methods 0.000 description 12
239000000243 solution Substances 0.000 description 12
LUXSISXJGNCOKN-UHFFFAOYSA-N 2,2,2-trichloro-1-(2-chlorophenyl)-1-(4-chlorophenyl)ethanol Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 LUXSISXJGNCOKN-UHFFFAOYSA-N 0.000 description 10
238000004458 analytical method Methods 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
238000005660 chlorination reaction Methods 0.000 description 5
239000012535 impurity Substances 0.000 description 4
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
230000000895 acaricidal effect Effects 0.000 description 3
239000000642 acaricide Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000010908 decantation Methods 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 2
VLTYTTRXESKBKI-UHFFFAOYSA-N (2,4-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 VLTYTTRXESKBKI-UHFFFAOYSA-N 0.000 description 1
ZWBANJRSWNLUEP-UHFFFAOYSA-N 2,2,2-trichloro-1,1-bis(2-chlorophenyl)ethanol Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)(Cl)Cl)(O)C1=CC=CC=C1Cl ZWBANJRSWNLUEP-UHFFFAOYSA-N 0.000 description 1
KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
PISCVMJEKRQOJH-UHFFFAOYSA-N CS(=O)C.ClC1=CC=C(C=C1)C(C(Cl)(Cl)Cl)(O)C1=CC=C(C=C1)Cl Chemical compound CS(=O)C.ClC1=CC=C(C=C1)C(C(Cl)(Cl)Cl)(O)C1=CC=C(C=C1)Cl PISCVMJEKRQOJH-UHFFFAOYSA-N 0.000 description 1
JWBOIMRXGHLCPP-UHFFFAOYSA-N Chloditan Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 JWBOIMRXGHLCPP-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
UCNVFOCBFJOQAL-UHFFFAOYSA-N DDE Chemical compound C=1C=C(Cl)C=CC=1C(=C(Cl)Cl)C1=CC=C(Cl)C=C1 UCNVFOCBFJOQAL-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
210000001691 amnion Anatomy 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001804 chlorine Chemical class 0.000 description 1
ACSXHCOUYYOVPA-UHFFFAOYSA-N chlorobenzene;hexane Chemical compound CCCCCC.ClC1=CC=CC=C1 ACSXHCOUYYOVPA-UHFFFAOYSA-N 0.000 description 1
GEAXLHPORCRESC-UHFFFAOYSA-N chlorocyclohexatriene Chemical class ClC1=CC=C=C[CH]1 GEAXLHPORCRESC-UHFFFAOYSA-N 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000007033 dehydrochlorination reaction Methods 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000000622 liquid--liquid extraction Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910002055 micronized silica Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000011002 quantification Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002834 transmittance Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/08—Ethanol
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
- C07C29/92—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound by a consecutive conversion and reconstruction

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Fireproofing Substances (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Compositions Of Macromolecular Compounds (AREA)

IL11243390A 1989-07-18 1990-07-17 Combined compounds of 1,1-bis) 4-chlorophenyl (-2,2,2-trichloroethanol and a process for their preparation, and their use in controlling plant mites IL112433A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
ES8902527A ES2013962A6 (es)	1989-07-18	1989-07-18	Procedimiento para la obtencion del 1,1-bis(4-clorofenil)-2,2,2-tricloroetanol a partir del 1,1-bis (clorofenil)-2,2,2-tricloroetanol tecnico.
ES9001766A ES2032243B1 (es)	1990-06-27	1990-06-27	Procedimiento para la obtencion del 1,1-bis (4-clorofenil)-2,2,2-tricloroetanol.
IL9510790A IL95107A (en)	1989-07-18	1990-07-17	Process for the preparation of 1,1-bit 4-chlorophenyl (-2,2,2-trichloroethanol

Publications (1)

Publication Number	Publication Date
IL112433A true IL112433A (en)	1996-10-16

Family

ID=26154428

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
IL11243390A IL112433A (en)	1989-07-18	1990-07-17	Combined compounds of 1,1-bis) 4-chlorophenyl (-2,2,2-trichloroethanol and a process for their preparation, and their use in controlling plant mites
IL9510790A IL95107A (en)	1989-07-18	1990-07-17	Process for the preparation of 1,1-bit 4-chlorophenyl (-2,2,2-trichloroethanol
IL11243395A IL112433A0 (en)	1989-07-18	1995-01-24	Addition compounds of 1,1-bis (4-chlorophenyl)-2,2,2-trichloroethanol and a process for the preparation thereof

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
IL9510790A IL95107A (en)	1989-07-18	1990-07-17	Process for the preparation of 1,1-bit 4-chlorophenyl (-2,2,2-trichloroethanol
IL11243395A IL112433A0 (en)	1989-07-18	1995-01-24	Addition compounds of 1,1-bis (4-chlorophenyl)-2,2,2-trichloroethanol and a process for the preparation thereof

Country Status (18)

Country	Link
US (1)	US5081319A (de)
EP (1)	EP0409689B1 (de)
JP (1)	JPH082816B2 (de)
KR (1)	KR920010638B1 (de)
CN (4)	CN1039989C (de)
AT (1)	ATE120169T1 (de)
BR (1)	BR9003486A (de)
CA (1)	CA2020920C (de)
DE (1)	DE69017965T2 (de)
DK (1)	DK0409689T3 (de)
ES (1)	ES2069712T3 (de)
FI (1)	FI95564C (de)
IE (1)	IE72092B1 (de)
IL (3)	IL112433A (de)
IN (2)	IN172157B (de)
NO (1)	NO173273C (de)
PT (1)	PT94736B (de)
TR (1)	TR27493A (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2077233T3 (es) *	1990-06-22	1995-11-16	Atochem Elf Sa	Procedimiento de preparacion de 1,1-bis(clorofenil)-2,2,2-tricloroetanol.
EA022813B1 (ru) *	2009-11-27	2016-03-31	Адверио Фарма Гмбх	СПОСОБ ОЧИСТКИ МЕТИЛ{4,6-ДИАМИНО-2-[1-(2-ФТОРБЕНЗИЛ)-1Н-ПИРАЗОЛО[3,4-b]ПИРИДИН-3-ИЛ]ПИРИМИДИН-5-ИЛ}МЕТИЛКАРБАМАТА И ЕГО ПРОИЗВОДНОЕ В ВИДЕ СУЛЬФИНИЛДИМЕТАНА
CN103483407B (zh) *	2013-10-10	2015-11-18	宁夏启元药业有限公司	一种硫氰酸红霉素萃取结晶用复合溶媒及萃取结晶方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2663703A (en) *		1953-12-22		Purification of stkaight-chain
US2812280A (en) *	1954-04-20	1957-11-05	Rohm & Haas	Preparation of bis (halophenyl) trichloroethanol
US2812362A (en) *	1955-10-12	1957-11-05	Rohm & Haas	Preparation of bis (chlorophenyl)-trichloroethanol
GB831421A (en) *	1955-11-28	1960-03-30	Metal & Thermit Corp	ª‡,ª‡ bis (chlorophenyl) alkanols
US4042498A (en)	1973-05-29	1977-08-16	Rohm And Haas Company	Separation of organic compounds by adsorption processes
CH658773A5 (fr) *	1984-05-22	1986-12-15	Nestle Sa	Procede de preparation d'un lait ecreme.
US4705902A (en) *	1985-10-03	1987-11-10	Rohm And Haas Company	DDTR-free 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol
JPS62286940A (ja) *	1986-06-02	1987-12-12	ロ−ム　アンド　ハ−ス　コンパニ−	ＤＤＴｒを含まない１，１−ビス（クロロフエニル）−２，２，２−トリクロロエタノ−ルの製造方法
DE3624911A1 (de) *	1986-07-23	1988-01-28	Hoechst Ag	Verfahren zur trennung von isomerengemischen aus 1.3- und 1.4-bis-(2-hydroxyhexafluoro-2-propyl)-benzol
IL89274A (en) *	1989-02-13	1994-04-12	Agan Chemical Manufacturers	Process for preparing environmentally safe dicofol

1990
- 1990-07-04 ES ES90401935T patent/ES2069712T3/es not_active Expired - Lifetime
- 1990-07-04 DE DE69017965T patent/DE69017965T2/de not_active Expired - Fee Related
- 1990-07-04 AT AT90401935T patent/ATE120169T1/de not_active IP Right Cessation
- 1990-07-04 EP EP90401935A patent/EP0409689B1/de not_active Expired - Lifetime
- 1990-07-04 DK DK90401935.3T patent/DK0409689T3/da active
- 1990-07-11 CA CA002020920A patent/CA2020920C/en not_active Expired - Fee Related
- 1990-07-13 NO NO903129A patent/NO173273C/no not_active IP Right Cessation
- 1990-07-17 IL IL11243390A patent/IL112433A/en not_active IP Right Cessation
- 1990-07-17 FI FI903612A patent/FI95564C/fi not_active IP Right Cessation
- 1990-07-17 IE IE260090A patent/IE72092B1/en not_active IP Right Cessation
- 1990-07-17 PT PT94736A patent/PT94736B/pt not_active IP Right Cessation
- 1990-07-17 IL IL9510790A patent/IL95107A/en not_active IP Right Cessation
- 1990-07-17 IN IN572/MAS/90A patent/IN172157B/en unknown
- 1990-07-18 TR TR00679/90A patent/TR27493A/xx unknown
- 1990-07-18 CN CN90104808A patent/CN1039989C/zh not_active Expired - Fee Related
- 1990-07-18 BR BR909003486A patent/BR9003486A/pt not_active IP Right Cessation
- 1990-07-18 US US07/555,066 patent/US5081319A/en not_active Expired - Lifetime
- 1990-07-18 JP JP2190342A patent/JPH082816B2/ja not_active Expired - Fee Related
- 1990-07-18 KR KR1019900010904A patent/KR920010638B1/ko not_active Expired
1992
- 1992-04-21 IN IN234MA1992 patent/IN173099B/en unknown
1995
- 1995-01-24 IL IL11243395A patent/IL112433A0/xx unknown
- 1995-05-20 CN CN95106205A patent/CN1066701C/zh not_active Expired - Fee Related
2000
- 2000-05-31 CN CN00117895A patent/CN1319578A/zh active Pending
- 2000-05-31 CN CN00117894A patent/CN1319579A/zh active Pending

Also Published As

Publication number	Publication date
CN1039989C (zh)	1998-09-30
TR27493A (tr)	1995-06-07
JPH082816B2 (ja)	1996-01-17
PT94736B (pt)	1997-03-31
NO173273C (no)	1993-11-24
CN1319578A (zh)	2001-10-31
IE902600A1 (en)	1991-02-27
CA2020920C (en)	1999-12-07
NO903129L (no)	1991-01-21
IL112433A0 (en)	1995-03-30
DE69017965T2 (de)	1995-11-16
US5081319A (en)	1992-01-14
JPH03115238A (ja)	1991-05-16
CN1050014A (zh)	1991-03-20
IE72092B1 (en)	1997-03-12
CN1066701C (zh)	2001-06-06
IN173099B (de)	1994-02-12
EP0409689B1 (de)	1995-03-22
PT94736A (pt)	1991-03-20
ATE120169T1 (de)	1995-04-15
FI95564C (fi)	1996-02-26
KR910002754A (ko)	1991-02-26
ES2069712T3 (es)	1995-05-16
EP0409689A3 (en)	1991-05-08
IL95107A0 (en)	1991-06-10
CN1117957A (zh)	1996-03-06
CN1319579A (zh)	2001-10-31
DE69017965D1 (de)	1995-04-27
EP0409689A2 (de)	1991-01-23
FI95564B (fi)	1995-11-15
NO903129D0 (no)	1990-07-13
IN172157B (de)	1993-04-17
NO173273B (no)	1993-08-16
BR9003486A (pt)	1991-08-27
FI903612A0 (fi)	1990-07-17
KR920010638B1 (ko)	1992-12-12
DK0409689T3 (da)	1995-08-14
IL95107A (en)	1996-05-14
CA2020920A1 (en)	1991-01-19

Legal Events

Date	Code	Title
1997-03-18	FF	Patent granted
1997-11-20	KB	Patent renewed
2005-07-25	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP0063374B1 (de)	1984-02-22	Substituierte Biphenylverbindungen
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JPH0643412B2 (ja)	1994-06-08	（±）‐３ａ‐６，６，９ａ‐テトラメチルペルヒドロナフト〔２，１‐ｂ〕フランの製造法
CH625235A5 (en)	1981-09-15	Process for the preparation of gamma-pyrones
IL112433A (en)	1996-10-16	Combined compounds of 1,1-bis) 4-chlorophenyl (-2,2,2-trichloroethanol and a process for their preparation, and their use in controlling plant mites
Flaming et al.	1980	β-Silylcarbonyl compounds as masked enones
EP0511036B1 (de)	1997-10-15	Synthesezwischenprodukte mit einem Hexanring und Verfahren zu ihrer Herstellung
DE19524584A1 (de)	1997-01-09	Verfahren zur stereoselektiven Herstellung von (-)3a,6,6,9a-Tetramethyl-perhydronaphtho[2,1-b]furan
CN114409612A (zh)	2022-04-29	一种高含量2-氯-5-氯甲基噻唑的制备方法
EP0383054B1 (de)	1995-06-28	Verfahren zur Herstellung von für die Umwelt unbedenklichem Dicofol und dessen Formulierungen
KR950006797B1 (ko)	1995-06-22	1,1-비스(r-페닐)-2,2,2-트리클로로에탄의 탈염산법
Prins	1953	Syntheses of polychloro‐compounds with aluminium chloride XI: The reaction between carbon tetrachloride and 1, 2‐dichloroethene
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DD296677A5 (de)	1991-12-12	Verfahren zur gewinnung von 1,1-bis(4-chlorphenyl)-2,2,2-trichlorethanol
US3331860A (en)	1967-07-18	Tricyclic ketone insecticides and process therefor
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KR0176327B1 (ko)	1999-03-20	7,8-디플루오로-벤즈옥사진 유도체의 제조방법
JPS608285A (ja)	1985-01-17	芳香剤として有用なジヒドロフラン誘導体を含有する香料組成物
JPH0670017B2 (ja)	1994-09-07	新規シクロペンタノン誘導体
BE885657A (fr)	1981-04-10	Procede de preparation de derives de l'acide 1,1-dioxopenicillanique et produits ainsi obtenus
CH545631A (fr)	1974-02-15	Utilisation de derives de la coumarine comme filtres antisolaires
BE432667A (de)
DE2461594A1 (de)	1975-07-17	5,6-epoxy-1,2,6-trimethyltricyclo eckige klammer auf 5,3,2,0 hoch 2,7 eckige klammer zu dodecan, verfahren zu seiner herstellung und seine verwendung als riechstoff
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