BE880478A - Benzimidazole-carbamates - Google Patents

Benzimidazole-carbamates Download PDF

Info

Publication number: BE880478A
Authority: BE; Belgium
Prior art keywords: emi; compounds; compounds according; benzimidazole; carbamates
Prior art date: 1978-12-06

Application number

BE0/198462A

Other languages

English (en)

French (fr)

Inventor

P Piccardi

G Confalonieri

L Da Col

P G Ramella

Original Assignee

Montedison Spa

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.)

1978-12-06

Filing date

1979-12-06

Publication date

1980-06-06

1979-12-06 Application filed by Montedison Spa filed Critical Montedison Spa

1980-06-06 Publication of BE880478A publication Critical patent/BE880478A/fr

Links

150000001875 compounds Chemical class 0.000 claims description 66
239000000203 mixture Substances 0.000 claims description 35
238000000034 method Methods 0.000 claims description 18
241001465754 Metazoa Species 0.000 claims description 16
230000000507 anthelmentic effect Effects 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
238000010521 absorption reaction Methods 0.000 claims description 2
235000013305 food Nutrition 0.000 claims description 2
238000002347 injection Methods 0.000 claims description 2
239000007924 injection Substances 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
150000004965 peroxy acids Chemical class 0.000 claims description 2
WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 claims 10
239000013543 active substance Substances 0.000 claims 4
BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical class NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 claims 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
229940124339 anthelmintic agent Drugs 0.000 claims 3
239000000921 anthelmintic agent Substances 0.000 claims 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
239000012327 Ruthenium complex Substances 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
239000007972 injectable composition Substances 0.000 claims 1
244000144972 livestock Species 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
230000000699 topical effect Effects 0.000 claims 1
206010061217 Infestation Diseases 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
241001494479 Pecora Species 0.000 description 5
241001558496 Talpa caeca Species 0.000 description 5
230000009467 reduction Effects 0.000 description 5
239000000243 solution Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
-1 5-substituted benzimidazole carbamates Chemical class 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
244000045947 parasite Species 0.000 description 2
235000021395 porridge Nutrition 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
QUWHIBBGKKRYFW-UHFFFAOYSA-N (4-amino-3-nitrophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1[N+]([O-])=O QUWHIBBGKKRYFW-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
241000238876 Acari Species 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
241000242541 Trematoda Species 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000306 component Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
150000001993 dienes Chemical group 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000012041 food component Nutrition 0.000 description 1
239000005428 food component Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
150000003303 ruthenium Chemical class 0.000 description 1
230000035943 smell Effects 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/14—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing bromine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/04—Chloro-alkenes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BE0/198462A 1978-12-06 1979-12-06 Benzimidazole-carbamates BE880478A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT30618/78A IT1100788B (it)	1978-12-06	1978-12-06	Benzimidazol-carbammati

Publications (1)

Publication Number	Publication Date
BE880478A true BE880478A (fr)	1980-06-06

Family

ID=11230215

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/198462A BE880478A (fr)	1978-12-06	1979-12-06	Benzimidazole-carbamates

Country Status (5)

Country	Link
JP (1)	JPS5598168A (cs)
BE (1)	BE880478A (cs)
CU (1)	CU35184A (cs)
IT (1)	IT1100788B (cs)
ZA (1)	ZA796611B (cs)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3929821A (en) *	1972-12-29	1975-12-30	Syntex Inc	5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives
SE443977B (sv) *	1977-05-10	1986-03-17	Chinoin Gyogyszer Es Vegyeszet	Forfarande for framstellning av 5(6)-tio-bensimidazolderivat
HU182763B (hu) *	1979-10-19	1984-03-28	Chinoin Gyogyszer Es Vegyeszet	Eljárás 5(6)-alkiltio-benzimidazolil-alkil-karbamátok előállítására

1978
- 1978-12-06 IT IT30618/78A patent/IT1100788B/it active
1979
- 1979-12-03 CU CU7935184A patent/CU35184A/es unknown
- 1979-12-05 JP JP15692479A patent/JPS5598168A/ja active Granted
- 1979-12-05 ZA ZA00796611A patent/ZA796611B/xx unknown
- 1979-12-06 BE BE0/198462A patent/BE880478A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPH0313231B2 (cs)	1991-02-22
ZA796611B (en)	1980-11-26
JPS5598168A (en)	1980-07-25
CU35184A (en)	1982-08-24
IT1100788B (it)	1985-09-28
IT7830618A0 (it)	1978-12-06

Legal Events

Date

Code

Title

Description

1992-06-30

RE

Patent lapsed

Owner name: MONTEDISON S.P.A.

Effective date: 19911231

Publication	Publication Date	Title
EP0041021B1 (fr)	1984-07-25	Nouveaux dérivés de l'acide cyclopropane carboxylique, leur préparation, leur application à la lutte contre les parasites des végétaux et des animaux, les compositions les renfermant et les nouveaux intermédiaires obtenus
FR2599739A1 (fr)	1987-12-11	Acides biphenyl hydroxamiques a action therapeutique
FR2490635A2 (fr)	1982-03-26	Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation et leur application a la lutte contre les parasites
EP0109866B1 (fr)	1987-08-19	Nouveaux dérivés de la sulfonylurée, leurs procédés de préparation et les compositions pharmaceutiques les renfermant
EP0556123A1 (fr)	1993-08-18	Nouveaux esters pyréthrinoides dérivés d'alcools thiazoliques, leur procédé de préparation et leur application comme pesticides
CA2050730A1 (fr)	1992-03-07	Derives du spiro [4.5] decane, leur procede de preparation et les compositions pharmaceutiques les renfermant
CA1095520A (fr)	1981-02-10	Procede de preparation de nouveaux derives de 20,21- dinoreburnamenine
EP0105006B1 (fr)	1986-03-19	Cyclopropane carboxylates à structure allénique, leur procédé et leurs intermédiaires de préparation, leur application à la lutte contre les parasites et les compositions les renfermant
EP0606175B1 (fr)	1995-10-11	Nouveaux dérivés 2-cyano 3-hydroxy propénamides, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant
EP0107570A1 (fr)	1984-05-02	Nouveaux dérivés de l'acide cyclopropane carboxylique substitués en 3 par une chaîne vinylique elle-même substituée, leur procédé et leurs intermédiaires de préparation, leur application comme pesticides et les compositions les renfermant
BE779775A (fr)	1972-08-24	Derives de l'uree, procede pour les preparer et leurs applications
BE880478A (fr)	1980-06-06	Benzimidazole-carbamates
BE897354A (fr)	1984-01-23	Derives de 1-phenoxy (phenylthio)-4-arylal-kynyloxy-benzene pourvus d'une activite acaricide et d'une activite hormonale juvenile
EP0024241B1 (fr)	1984-03-14	Nouveaux composés sulfonés comportant un cycle lactonique, ainsi qu'un procédé de préparation de dérivés cyclopropaniques
BE1000110A4 (fr)	1988-03-29	Nouveaux derives d'esters d'acide carbamique, compositions pesticides les contenant et procede pour les preparer.
EP0557192A1 (fr)	1993-08-25	Esters pyréthrinoides, dérivés de l'alcool 6-(trifluorométhyl)benzylique, leur procédé de préparation et leur application comme pesticides
EP0082040B1 (fr)	1986-01-15	Dérivés de diaza-3,7a cyclohepta(j,k)fluorènes, leur préparation et leur application en thérapeutique
EP0135415B1 (fr)	1987-04-29	Procédé de préparation d'esters d'alcoyle de l'acide cis chrysanthémique et nouveaux composés obtenus
CH646146A5 (fr)	1984-11-15	Derive du 1alpha,25-dihydroxy cholecalciferol et son procede de preparation.
EP0275221B1 (fr)	1991-04-17	Nouveaux dérivés du N-(1H-indol 4-yl) benzamide ainsi que leurs sels, leur application à titre de médicaments et les compositions les renfermant
EP0294295B1 (fr)	1992-08-26	Dérivés de la 1-arylsulfonyl 2-oxo 5-alcoxy pyrrolidine, leur procédé de préparation, leur application comme médicaments et les compositions les renfermant
BE883271R (fr)	1980-11-13	Nouveaux pyrethroides
FR2559149A1 (fr)	1985-08-09	Rodenticides a base de derives de la phenylpropargylamine
CH629796A5 (en)	1982-05-14	Therapeutically active compounds of 4-(2-thienylmethylamino)benzoic acid
CA1150280A (en)	1983-07-19	Benzimidazole-carbamates