IL96182A - Process for the preparation of molluscicidal 2,4,5-tribromopyrrole-3-carbonitrile compounds - Google Patents

Process for the preparation of molluscicidal 2,4,5-tribromopyrrole-3-carbonitrile compounds

Info

Publication number: IL96182A
Authority: IL; Israel
Prior art keywords: process according; molar equivalents; carbonitrile; preparation; tribromopyrrole
Prior art date: 1989-12-07

Application number

IL9618290A

Other languages

English (en)

Other versions

IL96182A0 (en

Original Assignee

American Cyanamid Co

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.)

1989-12-07

Filing date

1990-10-31

Publication date

1994-12-29

1990-10-31 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1991-07-18 Publication of IL96182A0 publication Critical patent/IL96182A0/xx

1994-12-29 Publication of IL96182A publication Critical patent/IL96182A/en

Links

238000000034 method Methods 0.000 title claims abstract description 24
238000002360 preparation method Methods 0.000 title claims abstract description 13
230000002013 molluscicidal effect Effects 0.000 title abstract description 9
RKLNEUUBXKXRHZ-UHFFFAOYSA-N 2,4,5-tribromo-1h-pyrrole-3-carbonitrile Chemical class BrC=1NC(Br)=C(C#N)C=1Br RKLNEUUBXKXRHZ-UHFFFAOYSA-N 0.000 title abstract description 8
239000003795 chemical substances by application Substances 0.000 claims abstract description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 13
229910052794 bromium Inorganic materials 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
239000002585 base Substances 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
VDCLSGXZVUDARN-UHFFFAOYSA-N molecular bromine;pyridine;hydrobromide Chemical compound Br.BrBr.C1=CC=NC=C1 VDCLSGXZVUDARN-UHFFFAOYSA-N 0.000 claims description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
239000001632 sodium acetate Substances 0.000 claims description 3
235000017281 sodium acetate Nutrition 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
239000007810 chemical reaction solvent Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
229910052801 chlorine Chemical group 0.000 claims 1
239000000460 chlorine Chemical group 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
239000002243 precursor Substances 0.000 abstract description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000007787 solid Substances 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
239000000047 product Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
PCYWMDGJYQAMCR-UHFFFAOYSA-N 1h-pyrrole-3-carbonitrile Chemical compound N#CC=1C=CNC=1 PCYWMDGJYQAMCR-UHFFFAOYSA-N 0.000 description 3
INVDBYXKIMVEPZ-UHFFFAOYSA-N 5-(2,2,2-trifluoroacetyl)-1h-pyrrole-3-carbonitrile Chemical compound FC(F)(F)C(=O)C1=CC(C#N)=CN1 INVDBYXKIMVEPZ-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000012267 brine Substances 0.000 description 3
230000031709 bromination Effects 0.000 description 3
238000005893 bromination reaction Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-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
-1 acetic acid Chemical class 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
239000002024 ethyl acetate extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
UMVVPYXSJKIFST-UHFFFAOYSA-N 2,2,2-trifluoro-1-(1h-pyrrol-2-yl)ethanone Chemical compound FC(F)(F)C(=O)C1=CC=CN1 UMVVPYXSJKIFST-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
SAEZQFNKTQKVSM-UHFFFAOYSA-N 4-cyano-1h-pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC(C#N)=CN1 SAEZQFNKTQKVSM-UHFFFAOYSA-N 0.000 description 1
GZOKBSGKQFQHRS-UHFFFAOYSA-N 5-(2,2,2-trichloroacetyl)-1h-pyrrole-3-carbonitrile Chemical compound ClC(Cl)(Cl)C(=O)C1=CC(C#N)=CN1 GZOKBSGKQFQHRS-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910000435 bromine oxide Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000003750 molluscacide Substances 0.000 description 1
150000005242 nitropyrroles Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
FJGIHZCEZAZPSP-UHFFFAOYSA-N tetrahedrane Chemical compound C12C3C1C32 FJGIHZCEZAZPSP-UHFFFAOYSA-N 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrrole Compounds (AREA)
Catching Or Destruction (AREA)
Plural Heterocyclic Compounds (AREA)
Carbon And Carbon Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pyridine Compounds (AREA)

IL9618290A 1989-12-07 1990-10-31 Process for the preparation of molluscicidal 2,4,5-tribromopyrrole-3-carbonitrile compounds IL96182A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/447,961 US5008403A (en)	1989-12-07	1989-12-07	Deacylative bromination process for the preparation of molluscicidal 2,4,5-tribromopyrrole-3-carbonitrile compounds

Publications (2)

Publication Number	Publication Date
IL96182A0 IL96182A0 (en)	1991-07-18
IL96182A true IL96182A (en)	1994-12-29

Family

ID=23778454

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9618290A IL96182A (en)	1989-12-07	1990-10-31	Process for the preparation of molluscicidal 2,4,5-tribromopyrrole-3-carbonitrile compounds

Country Status (16)

Country	Link
US (1)	US5008403A (de)
EP (1)	EP0431305B1 (de)
JP (1)	JP2992334B2 (de)
KR (1)	KR0160974B1 (de)
AT (1)	ATE117676T1 (de)
AU (1)	AU636932B2 (de)
BR (1)	BR9006199A (de)
CA (1)	CA2031578C (de)
DE (1)	DE69016380T2 (de)
DK (1)	DK0431305T3 (de)
ES (1)	ES2067621T3 (de)
HU (1)	HU204783B (de)
IE (1)	IE66565B1 (de)
IL (1)	IL96182A (de)
PT (1)	PT96088B (de)
ZA (1)	ZA909814B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5204332A (en) *	1988-12-05	1993-04-20	American Cyanamid Company	Pyrrole carbonitrile and nitropyrrole insecticidal and acaricidal and molluscicidal agents
US5371239A (en) *	1989-12-22	1994-12-06	American Cyanamid Company	Methods and compositions for protecting animals against attack and infestation by helminth, acarid and arthropod endo- and ectoparasites
US5449789A (en) *	1992-11-30	1995-09-12	American Cyanamid Company	Debrominative chlorination of pyrroles
US5359089A (en) *	1993-12-22	1994-10-25	American Cyanamid Company	Process for the preparation of 2,4,5-tribromopyrrole-3-carbonitrile

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR8906202A (pt) *	1988-12-05	1990-09-25	American Cyanamid Co	Processo e composicao para o controle de pragas de insetos,acaros e moluscos,composto para tal controle e processo para sua preparacao

1989
- 1989-12-07 US US07/447,961 patent/US5008403A/en not_active Expired - Lifetime
1990
- 1990-10-29 EP EP90120661A patent/EP0431305B1/de not_active Expired - Lifetime
- 1990-10-29 ES ES90120661T patent/ES2067621T3/es not_active Expired - Lifetime
- 1990-10-29 AT AT90120661T patent/ATE117676T1/de not_active IP Right Cessation
- 1990-10-29 DK DK90120661.5T patent/DK0431305T3/da active
- 1990-10-29 DE DE69016380T patent/DE69016380T2/de not_active Expired - Fee Related
- 1990-10-31 IL IL9618290A patent/IL96182A/en not_active IP Right Cessation
- 1990-11-30 JP JP2331006A patent/JP2992334B2/ja not_active Expired - Fee Related
- 1990-12-05 PT PT96088A patent/PT96088B/pt not_active IP Right Cessation
- 1990-12-05 CA CA002031578A patent/CA2031578C/en not_active Expired - Fee Related
- 1990-12-06 KR KR1019900020047A patent/KR0160974B1/ko not_active Expired - Fee Related
- 1990-12-06 AU AU67847/90A patent/AU636932B2/en not_active Ceased
- 1990-12-06 BR BR909006199A patent/BR9006199A/pt not_active IP Right Cessation
- 1990-12-06 IE IE439790A patent/IE66565B1/en not_active IP Right Cessation
- 1990-12-06 ZA ZA909814A patent/ZA909814B/xx unknown
- 1990-12-07 HU HU908123A patent/HU204783B/hu not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE69016380D1 (de)	1995-03-09
KR0160974B1 (ko)	1998-12-01
IE66565B1 (en)	1996-01-24
PT96088B (pt)	1998-02-27
CA2031578C (en)	2002-01-08
AU636932B2 (en)	1993-05-13
ES2067621T3 (es)	1995-04-01
JP2992334B2 (ja)	1999-12-20
JPH03181459A (ja)	1991-08-07
EP0431305B1 (de)	1995-01-25
KR910011776A (ko)	1991-08-07
ATE117676T1 (de)	1995-02-15
CA2031578A1 (en)	1991-06-08
US5008403A (en)	1991-04-16
HU908123D0 (en)	1991-06-28
BR9006199A (pt)	1991-09-24
HUT56344A (en)	1991-08-28
DK0431305T3 (da)	1995-04-03
DE69016380T2 (de)	1995-08-24
IE904397A1 (en)	1991-06-19
AU6784790A (en)	1991-06-13
HU204783B (en)	1992-02-28
PT96088A (pt)	1991-09-30
IL96182A0 (en)	1991-07-18
EP0431305A1 (de)	1991-06-12
ZA909814B (en)	1992-08-26

Legal Events

Date	Code	Title	Description
1997-01-10	KB	Patent renewed
2005-07-25	MM9K	Patent not in force due to non-payment of renewal fees

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JPH0576478B2 (de)	1993-10-22
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