WO1993024446A1 - Composes anthelmintiques et/ou namatocides - Google Patents

Composes anthelmintiques et/ou namatocides Download PDF

Info

Publication number
WO1993024446A1
WO1993024446A1 PCT/AU1993/000261 AU9300261W WO9324446A1 WO 1993024446 A1 WO1993024446 A1 WO 1993024446A1 AU 9300261 W AU9300261 W AU 9300261W WO 9324446 A1 WO9324446 A1 WO 9324446A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
alkyl
general formula
group
anthelmintic
Prior art date
Application number
PCT/AU1993/000261
Other languages
English (en)
Inventor
Christopher Bryant
Wilfrid Douglas Laidlaw Crow
Dugald Maxwell Paton
Eva-Maria Bennet-Jenkins
Original Assignee
The Australian National University
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.)
Filing date
Publication date
Application filed by The Australian National University filed Critical The Australian National University
Publication of WO1993024446A1 publication Critical patent/WO1993024446A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C07D295/116—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings with the doubly bound oxygen or sulfur atoms directly attached to a carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
    • C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C07C225/18—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings the carbon skeleton containing also rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • This invention relates to a novel class of compounds, related to the plant growth regulator, G, contained in the leaves of Eucalyptus grandis , which have been found to have an elmintic and/or nematocidal activity.
  • the invention also relates to methods for the use of these compounds as an ehnintics and/or nematocides, and to compositions comprising these compounds as active ingredients.
  • G 4 a natural precursor of G 3 : the existence of analogous precursors of G j and G 2 is also envisaged.
  • G is used to include the naturally occurring G,, G ⁇ G 3 and G 4 , as well as natural and synthetic structural analogues, precursors and derivatives thereof.
  • X and Y which may be the same or different, each represents a heteroatom, preferably O;
  • R,, R 3 and R 4 which may be the same or different, each represents H or alkyl (preferably C,-C 6 alkyl which may be substituted) or aryl (preferably phenyl which may be substituted);
  • R 2 represents H or alkyl (preferably C ⁇ -C 6 alkyl which may be substituted) or aryl (preferably phenyl which may be substituted), or W;
  • W represents a protein residue linked through an amine group, or a group of the formula OR 5 , -SR j or -NR j R ⁇ , wherein R j and R ⁇ , which may be the same or different, each represents H or alkyl (preferably C,-C 6 alkyl which may be substituted) or aryl (preferably phenyl which may be substituted), or R j and Rg together with the nitrogen atom to which they are attached form a saturated 5- or 6- membered heterocyclic ring which may be substituted and may contain one or more other hetero atoms.
  • the group A...3 completes a carbocyclic or heterocyclic ring, particularly a 5- or 6- membered ring.
  • the group A...JB is a group of the formula
  • R 7 and R 8 which may be the same or different, each represents H or alkyl (preferably C,-C 6 alkyl which may be substituted) or aryl (preferably phenyl which may be substituted).
  • alkyl or aryl groups, or the carbocyclic or heterocyclic rings of compounds of the general formulae I or II are substituted, typically they are substituted by one or more - alkyl or alkenyl, C j -Cg alkoxy or alkenyloxy, hydroxy, cyano, amino, -Cg ai lamino or di-C j - aUcylamino groups.
  • W is a dialkylamino group (more preferably, dimethylamino or diethylamino) or a pyrrolidinyl group.
  • R 3 and R 4 are H, X and Y are O, A ... B is a -CH 2 -CR 7 R 8 -CH 2 - group (more preferably, a -CH 2 -CMe 2 - CH 2 - group) and R j represents a C 6 alkyl or phenyl group which is optionally substituted.
  • a ... B is a -
  • CR 7 R 8 -CO-CR 7 R 8 - group (more preferably a -CMe ⁇ CO-CMe ⁇ r group)
  • X and Y are O
  • R t is a -Cg alkyl group
  • R 2 represents a dialkylamino group (more preferably, dimethylamino or die ⁇ ylamino) or a pyrrolidinyl group.
  • the present invention extends to a method of anthelmintic and/or nematocidal treatment of an animal, which comprises administration to the animal of an effective amount of a compound of the general formula I or II as described above.
  • the present invention also provides a composition for use in the anthelmintic and/or nematocidal treatment of an animal, comprising a effective amount of a compound of the general formula I or II as described above, together with an acceptable pharmaceutical or veterinary carrier or diluent.
  • Animals which may be treated in accordance with the present invention include both wild and domestic animals, particularly domestic animals such as horses, cats and dogs as well as sheep, cattle and other ruminant animals.
  • the compounds of the present invention may be administered by any suitable route, for example, orally or parenteraUy by intraperitoneal, subcutaneous or intravenous injection.
  • Suitable effective dosages may range for example from 0.1 to 100 mg/kg (more particularly from 1 to 50 mg/kg) body weight of the animal to be treated, and will be readily determined by simple trial protocols.
  • test larvae In an in vitro larval assay, third stage infective larvae of a laboratory strain of the sheep nematode Haemonchus contortus which has not been exposed to anthelmintic treatment for 15 years are used as the test larvae. These larvae are incubated in the presence of compound and efficacy is determined from the percent reduction in the number of active larvae compared with untreated controls after 3 days incubation. The compounds are tested in concentrations ranging from 0.1-100 mM, in triplicate. Log concentration/probit curves are drawn up and the LD ⁇ calculated. The compounds tested and results are set out in Table 1.
  • Table 2A shows the time in minutes or hours for 10 mM of the compound to immobilise the adult worms. No anthehnintic compounds were administered i the control experiment.
  • Table 2B shows the activity score for the parasites after being treated with 1 mM of each compound (again no compound was administered in the control experiment).
  • Compound No.252 was chosen for testing in in vivo laboratory models based on efficacy in (a) the in vitro larval assay and (b) the in vitro susceptibility of adult parasites over a broad spectrum - trematodes, cestodes and nematodes.
  • the compound was administered: an oral aqueous suspension, an intraperitoneal injection of aqueous suspension, in a subcutaneous suspension in oil, single or repeated dose, iv an intravenous injection in serum or albumin.
  • mice 252 with the compound absorbed in PVP at the rate of 10:1.
  • 0.2g of this 252/PVP was suspended in 1 ml of water and the suspension administered orally to mice infected with the mouse nematode Nematospiroides d bius .
  • the number of worms recovered from mice treated with 252/PVP and PVP alone are shown in Table 5.
  • a 27.9% reduction in worm burden is noted (sig. at 95%).
  • the compounds may be prepared by the following general procedure for Mannich bases derived from dimethylamine:
  • reaction mixture is evaporated to dryness, then dissolved in ethyl acetate (30 mL) and washed with water until the pH of the aqueous layer is - 5.
  • the organic extract is dried (MgS0 4 ) and the solvent removed to provide the enedione (80 - 95%).
  • the enedione may then be treated with a variety of nitrogen and sulfur nucleophiles affording the appropriate Mannich bases or their sulphur analogues, as exemplified below.
  • Compound No. 269 was prepared by the following procedure.
  • Compound No. 252 was dissolved in sterile sheep serum and administered intravenously to one sheep infected with Haemonchus contortus (nematode) and Monezia expansa (cestode).

Abstract

L'invention concerne un composé ayant une activité anthelmintique et/ou nématocide, de la formule générale (I) ou (II), dans lesquelles X et Y pouvant être identiques ou différents représente chacun un hétéroatome; R1, R3 et R4, pouvant être identiques ou différents, représentent chacun H ou alkyle ou alryle; R2 représente H ou alkyle ou aryle, ou W; le groupe A...B complète un cycle carbocyclique ou hétérocyclique pouvant être substitué; et W représente un résidu protéique lié par un groupe aminé, ou un groupe de la formule -OR5, -SR6 ou -NR5R6, dans lesquels R5 et R6, lesquels peuvent être identiques ou différents, représentent chacun H ou alkyle, ou R5 ainsi que R6 avec l'atome d'azonte auquel il sont fixés forment un cycle hétérocyclique saturé à 5 ou 6 éléments pouvant être substitués et contenir un ou plusieurs autres hétéroatomes. L'invention concerne également des compositions anthelmintiques et/ou nématocides ainsi que des procédés de traitement.
PCT/AU1993/000261 1992-06-02 1993-06-02 Composes anthelmintiques et/ou namatocides WO1993024446A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
AUPL271592 1992-06-02

Publications (1)

Publication Number Publication Date
WO1993024446A1 true WO1993024446A1 (fr) 1993-12-09

Family

ID=3776196

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AU1993/000261 WO1993024446A1 (fr) 1992-06-02 1993-06-02 Composes anthelmintiques et/ou namatocides

Country Status (2)

Country Link
WO (1) WO1993024446A1 (fr)
ZA (1) ZA933847B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6372693B1 (en) 1997-05-07 2002-04-16 Basf Aktiengesellschaft Substituted 2-(3-alkenyl-benzoyl)-cyclohexane-1,3-diones
WO2002089587A1 (fr) * 2001-05-08 2002-11-14 Bioprospect Limited Procedes et compositions antiparasitaires
US6828460B2 (en) 1999-03-22 2004-12-07 Pfizer Inc. Resorcinol derivatives
JP2007500705A (ja) * 2003-07-28 2007-01-18 スミスクライン ビーチャム コーポレーション 化合物

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56149462A (en) * 1980-04-22 1981-11-19 Fuji Photo Film Co Ltd Photoconducting composition and photosensitive material for electrophotography by use of same
JPS5746943A (en) * 1981-04-25 1982-03-17 Nippon Soda Co Ltd Preparation of cyclohexane derivative
DE3150266A1 (de) * 1981-01-16 1982-09-23 Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa Elektrophotographisch empfindliche materialien
JPH01272561A (ja) * 1988-04-22 1989-10-31 Nippon Nohyaku Co Ltd シクロヘキサンジオン誘導体及びその製造方法並びに除草剤
US5179093A (en) * 1991-05-10 1993-01-12 Schering Corporation Quinoline-diones

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56149462A (en) * 1980-04-22 1981-11-19 Fuji Photo Film Co Ltd Photoconducting composition and photosensitive material for electrophotography by use of same
DE3150266A1 (de) * 1981-01-16 1982-09-23 Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa Elektrophotographisch empfindliche materialien
JPS5746943A (en) * 1981-04-25 1982-03-17 Nippon Soda Co Ltd Preparation of cyclohexane derivative
JPH01272561A (ja) * 1988-04-22 1989-10-31 Nippon Nohyaku Co Ltd シクロヘキサンジオン誘導体及びその製造方法並びに除草剤
US5179093A (en) * 1991-05-10 1993-01-12 Schering Corporation Quinoline-diones

Non-Patent Citations (13)

* Cited by examiner, † Cited by third party
Title
BIOORG. CHIM., Vol. 4, No. 11, published 1978, "Synthesis of 18-Amino-D-Homoestranes", (GEVORKYAN, K.A. et al.), pages 1520-1528. *
BULLETIN OF CHEMICAL SOCIETY OF ETHIOPIA, Vol. 3, No. 2, published 1989, "Reactions of 6-Arylmethylene-Thiazolo[3,2-aÜPyrimidine-3,5,7(2H)-Trines", (SOLIMAN, A.A. et al.). *
CHEM. BER., Vol. 119, No. 11, published 1986, "Ring-Opening of N-(Tetraalkylamidinio) Pyridinium Salts by Anions of CH-Acidic Methylene Compounds", (HENNING, H.G. et al.). *
INDIAN JOURNAL OF CHEMISTRY, Vol. 27B, No. 5, published May 1988, "Synthesis of Quinazolinylpyrimidinediones and their Anti-Inflammatory Activity", (KUMAR, A. et al.), pages 443-447. *
PATENT ABSTRACTS OF JAPAN, C-111, page 90; & JP,A,57 046 943 (NIPPON SODA K.K.), 17 March 1982. *
PATENT ABSTRACTS OF JAPAN, C-680, page 10; & JP,A,1 272 561 (NIPPON NOHYAKU CO., LTD.), 31 October 1989. *
PATENT ABSTRACTS OF JAPAN, C-92, page 79; & JP,A,56 149 462 (FUJI SHASHIN FILM K.K.), 19 November 1981. *
PHARMAZIE, Vol. 40, No. 10, published 1985, "Aminomethylation of 1,3-Diketones", (MOEHRLE, H. et al.), pages 697-701. *
PHYTOCHEMISTRY, Vol. 26, No. 12, published 1987, "Biomimetic Synthesis of 2,3-Dioxabicyclo[4,4,0] Decanes as Plant Growth Regulators", (KALSI, P.S. et al.), pages 3367-3369. *
RESEARCH DISCLOSURE, Vol. 144, published April 1976, "Light-Absorbing Dyes for Photographic Elements", (Anonymous Disclosure), pages 17-20. *
Z. CHEM., Vol. 18, No. 7, published 1978, "Preparation and Spectroscopic Properties of Aminomethylene-Cycloalkanones", (HENNING, H.G. et al.), pages 256-7. *
Z. NATURFORSCH, Vol. 46C, No. 7-8, published 1991, "Photoautotrophic Cultured Plant Cells: A Novel System to Survey New Photosynthetic Electron Transport Inhibitors", (SATO, F. et al.), pages 563-568. *
Z. PHYS. CHEMIE, Leipzig, Vol. 258, No. 4, published 1977, "E.P.R. Studies on the Phosphorescing Triplet States of Enamines and Enamino Ketones", (STOESSER, R. et al.). *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6372693B1 (en) 1997-05-07 2002-04-16 Basf Aktiengesellschaft Substituted 2-(3-alkenyl-benzoyl)-cyclohexane-1,3-diones
US6828460B2 (en) 1999-03-22 2004-12-07 Pfizer Inc. Resorcinol derivatives
US6933319B2 (en) 1999-03-22 2005-08-23 Pfizer Inc. Resorcinol derivatives
WO2002089587A1 (fr) * 2001-05-08 2002-11-14 Bioprospect Limited Procedes et compositions antiparasitaires
JP2004534021A (ja) * 2001-05-08 2004-11-11 バイオプロスペクト リミティッド 害虫を制御するための方法及び組成物
US7820209B2 (en) 2001-05-08 2010-10-26 Bioprospect Limited Methods and compositions for controlling pests
JP4651267B2 (ja) * 2001-05-08 2011-03-16 バイオプロスペクト リミティッド 害虫を制御するための方法及び組成物
US9474270B2 (en) 2001-05-08 2016-10-25 Bioprosepect Limited Methods and compositions for controlling pests
JP2007500705A (ja) * 2003-07-28 2007-01-18 スミスクライン ビーチャム コーポレーション 化合物

Also Published As

Publication number Publication date
ZA933847B (en) 1993-12-28

Similar Documents

Publication Publication Date Title
FI59247C (fi) Analogifoerfarande foer framstaellning av en mot parasitsjukdomar hos djur verkande metyl-5-propyltio-2-bensimidazolkarbamat
DE2815621C2 (fr)
PL85278B1 (fr)
DE2142317A1 (de) Hypnotisches mittel
WO1993024446A1 (fr) Composes anthelmintiques et/ou namatocides
DE1954584A1 (de) Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
CA1240326A (fr) 2-(.omega.-ALCOYLAMINOALCOYL)- ET 2-(.omega.-DIALCOYLAMINOALCOYL)-3-(4-X-BENZYLIDENE) -PHTALIMIDINES
CH634307A5 (de) Anthelmintisch wirkende benzimidazolderivate, verfahren zu ihrer herstellung und mittel enthaltend diese wirkstoffe.
US4151298A (en) Anthelmintic compositions
ATE77237T1 (de) Anthelmintische acylhydrazone, verfahren zur verwendung und zusammensetzungen.
US3755406A (en) Isothiocyano diphenylamines
ATE71839T1 (de) Anthelmintische acylhydrazone verfahren zur verwendung und zusammensetzungen.
DE2105112A1 (de) Chinoxahn di Noxide und ihre Verwendung in einem pharmazeutischen Gemisch
KR100450274B1 (ko) 폴리에톡실화 아스코르브산 유도체를 함유하는 동물용사료첨가제 조성물
US4004019A (en) Insect control compounds
DE3342999A1 (de) Schwefelhaltige benzylidenderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
RU2255935C2 (ru) 5,7-дизамещенный-4,6-динитробензофуроксан общей формулы c6n4o6(r1)2, обладающий акарицидной и бактерицидной активностью
DE2502116A1 (de) Anthelmintica auf der grundlage von 2-trifluormethyl-benzimidazol-derivaten
US3946047A (en) Alkylcinnamylphenols as mosquito larvicides
US4943589A (en) Anthelmintic dysinins of marine origin
US4279903A (en) Diphydrothiazine derivatives
RU2404975C1 (ru) Антигельминтное средство
CA1110633A (fr) Carbamate de benzimidazol ayant une activite contre les parasites du tractus digestif et des poumons
US3983141A (en) Derivatives of 5-hydroxy-6-diloweralkylaminomethyl-benzofurans
US3179560A (en) Method of employing sulfamoylphenyl esters of organic phosphates

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU CA JP NZ US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA