DE1963192A1 - 2-arylimino-oxazolidines ectoparasiticides - Google Patents

2-arylimino-oxazolidines ectoparasiticides

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Publication number
DE1963192A1
DE1963192A1 DE19691963192 DE1963192A DE1963192A1 DE 1963192 A1 DE1963192 A1 DE 1963192A1 DE 19691963192 DE19691963192 DE 19691963192 DE 1963192 A DE1963192 A DE 1963192A DE 1963192 A1 DE1963192 A1 DE 1963192A1
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Germany
Prior art keywords
arylimino
oxazolidines
ectoparasiticides
alkenyl
alkoxy
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Pending
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DE19691963192
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German (de)
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Rudolf Dr Hiltmann
Wilhelm Dr Stendel
Hartmund Dr Wollweber
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Bayer AG
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Bayer AG
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Priority to DE19691963192 priority Critical patent/DE1963192A1/en
Publication of DE1963192A1 publication Critical patent/DE1963192A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D263/28—Nitrogen atoms not forming part of a nitro radical

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

2-Arylimino-oxazolidines ectoparasiticides Compsn. active against acarids, contains a cpd. of formula (I) (where R is a gp. of formula (II) or (III); R1 is halogen CF3, 1-4C alkyl, alkenyl or alkoxy, R2 is H, alkyl, alkoxy, alkenyl, halogen, CF3 or CHF2; R3 is H or CH3; n =1 or 2) and may also contain a filler and/or surfactant.

Description

Ektoparasiticide Mittel Die vorliegende Erfindung betrifft ektoparasiticide Mittel auf der Basis von 2-Arylimino-oxazolidinen und/oder deren Salzen. Die Verwendung dieser Verbindungen als Antihypertensivaund als Depressantien des Zentralnervensystems ist bereits bekannt (vgl. USA-Patentschrift 3 453 284). Ectoparasiticides The present invention relates to ectoparasiticides Agents based on 2-arylimino-oxazolidines and / or their salts. The usage of these compounds as antihypertensive agents and as central nervous system depressants is already known (see US Pat. No. 3,453,284).

Es wurde nun gefunden, daß 2-Arylimino-oxazolidone und/oder deren Salze der Formel (I) R' Halogen wie Chlor, Fluor oder Brom, ferner Trifluormethyl, Alkyl, Alkenyl oder Alkoxy jeweils mit 1 - 4 C-Atomen R" Wasserstoff, Alkyl, alkoxy, Alkenyl, Halogen wie Chlor, Brom, Fluor, Trifluormethyl oder Difluormethyl ibasserstoff oder Methyl und n 1 oder 2 bedeuten, zum Bekämpfung tierischer Ektoparasiten aus der Klasse der Acariden hervorragend geeignet sind.It has now been found that 2-arylimino-oxazolidones and / or their salts of the formula (I) R 'halogen such as chlorine, fluorine or bromine, also trifluoromethyl, alkyl, alkenyl or alkoxy each with 1-4 carbon atoms R "hydrogen, alkyl, alkoxy, alkenyl, halogen such as chlorine, bromine, fluorine, trifluoromethyl or difluoromethyl hydrogen or methyl and n is 1 or 2, are eminently suitable for combating animal ectoparasites from the class of acarids.

Bisher ist von Arylaminooxazolidinen lediglich eine Anwendung als Ilypotensiva und als Depressantien des Zentralnervensystems beschrieben worden (USA-Patentschrift 3 453 284) Von den bekannten, gegen Zecken wirksamen Verbindungen mußte das N-(2-Methyl-4-chlorphenyl-)-N'-formamidin (Südafrika nische Patentschrift 66/4135) wegen der Instabilität der Verbindung im'Rinderdip' zurückgezogen werden.So far, Arylaminooxazolidinen is only an application as Ilypotensiva and as depressants of the central nervous system have been described (USA patent 3,453,284) Of the known compounds effective against ticks, N- (2-methyl-4-chlorophenyl -) - N'-formamidine had to be (South Africa niche patent 66/4135) because of the instability of the connection in the 'beef dip' be withdrawn.

Die erfindungsgemäß verwendbaren Arylimino-oxazolidine zeigen jedoch überraschenderweise eine stärkere Wirkung als die bekannten Produte, insbesondere gegen Zeckenstämme, die gegen Phosphorsäureester resistent geworden sind. Darüber hinaus sind sie bei der Anwendung im "Rinderdip" beständig.However, the arylimino-oxazolidines which can be used according to the invention show Surprisingly, a stronger effect than the known products, in particular against tick strains that have become resistant to phosphoric acid esters. About that In addition, they are stable when used in "beef dip".

,ls Beispiele für erfindungsgemäß verwendbare Stoffe seien in einzelnen genannt: 2-(2,6-Dichlorphenyl)-imino-oxazolidin sowie Verbindungen der allgemeinen Formel (IV) R' R" R"' oder R"' CH3 4,6(CH3)2 H CH3 CH3 4-CH3,6-C2H5 H CH3 CH3 6-CH3 H CH3 CH3 6-C2H5 H CH3 C2H5 6-C2H5 H CH3 C2H5 4-CH3,6-C2H5 H CH3 CH3 6-Cl H CH3 CH3 4-F,6-CH3 H CH3 CH3 4-CH3,6-Cl H CH3 CH3 4-Cl,6-CH3 H CH3 CF3 4-Cl H CH3 Cl 4,6-Cl H CH3 Cl 5-Cl H CH3 Cl 3-Cl H CH3 Cl 4-CHF2 H CH3 CH2-CH=CH2 6-CH3 H CH3 CH3 H H CH3 Cl H H CH3 CF3 H H CH3 CH3 6-OCH3 H CH3 OCF3 6-OCH3 H CH3 OCF3 H H CH3 CH3 4-OCH3,6-CH3 H CH3 CH3 4-OC2H5-6-CH3 H CH3 Die erfindungsgemäß verwendbaren Stoffe sind zum Teil als solche bekannt. Sie können z.B. dadurch hergestellt werden, daß man Arylisocyanid-dichloride der allgemeinen Formel (V) in der R', R" und n die oben angegebene Bedeutung besitzen mit Äthanolaminen der Formel (VI) HOH2C - CH2 - NH -(VI) vorzugsweise in Wasser oder organischen Lösungsmitteln, gegebenenfalls unter Zusatz von Basen wie Triäthylamin, Natriumcarbonat oder Natriumhydroxid umsetzt, oder daß man Ohloräthylharnstoffe der Formel (VIT) in der R', R" und n die oben angegebene Bedeutung aufweisen, durch erhitzen in Wasser cyclisiert.As examples of substances that can be used according to the invention, the following may be mentioned individually: 2- (2,6-dichlorophenyl) -imino-oxazolidine and compounds of the general formula (IV) R 'R "R"' or R "'CH3 4,6 (CH3) 2 H CH3 CH3 4-CH3,6-C2H5 H CH3 CH3 6-CH3 H CH3 CH3 6-C2H5 H CH3 C2H5 6-C2H5 H CH3 C2H5 4-CH3,6-C2H5 H CH3 CH3 6-Cl H CH3 CH3 4-F, 6-CH3 H CH3 CH3 4-CH3,6-Cl H CH3 CH3 4-Cl, 6-CH3 H CH3 CF3 4-Cl H CH3 Cl 4,6-Cl H CH3 Cl 5-Cl H CH3 Cl 3-Cl H CH3 Cl 4-CHF2 H CH3 CH2-CH = CH2 6-CH3 H CH3 CH3 HH CH3 Cl HH CH3 CF3 HH CH3 CH3 6-OCH3 H CH3 OCF3 6-OCH3 H CH3 OCF3 HH CH3 CH3 4-OCH3,6-CH3 H CH3 CH3 4-OC2H5-6-CH3 H CH3 Some of the substances that can be used according to the invention are known as such one aryl isocyanide dichloride of the general formula (V) in which R ', R "and n have the meaning given above with ethanolamines of the formula (VI) HOH2C - CH2 - NH - (VI), preferably in water or organic solvents, optionally with the addition of bases such as triethylamine, sodium carbonate or sodium hydroxide, or that one Ohloräthylureas of the formula (VIT) in which R ', R "and n have the meaning given above, cyclized by heating in water.

Die Arylinooxazolidine besitzen basischen Charakter, Sie bilden mit anorganischen oder organischen Säuren Salze, z.B. Hydrochloride, Sulfate, Phosphate, Nitrate, Fumarate, Naphthalindisulfonate, Methansulfonate, nie Herstellung der erfindungsgemäß zu verwendenden Verbindun kann beispielsweise wie folgt durchgeführt werden: Zu einer Lösung von 80 g (2 Mol) Natriumhydroxid in 1000 ml Wasser fügt man 85 g (1,25 Mol) Äthanolamin, tropft bei 25 bis 50°C eine Lösung von 276,5 g (1 Ilol)4-Ohlor-2-Trifluormethylphenylisocyaniddichlorid in 500 ml Dioxan ein, rührt die Mischung 2 Stunden bei 50°C nach, saugt vom ausgefallenen Niederschlag ab und erhält nach dem Trocknen und Umlössen aus Essigester 211 g des obigen Produkts vom Schmelzpunkt 1C000.The arylinooxazolidines have a basic character, they form salts with inorganic or organic acids, e.g. hydrochlorides, sulfates, phosphates, nitrates, fumarates, naphthalene disulfonates, methanesulfonates, never The compound to be used according to the invention can be prepared, for example, as follows: 85 g (1.25 mol) of ethanolamine are added to a solution of 80 g (2 mol) of sodium hydroxide in 1000 ml of water, and a solution of 276.5 g (1 Ilol) of 4-chloro-2 is added dropwise at 25 to 50 ° C Trifluoromethylphenyl isocyanide dichloride in 500 ml of dioxane, the mixture is stirred for 2 hours at 50 ° C., the precipitate is filtered off with suction and, after drying and dissolving from ethyl acetate, 211 g of the above product with a melting point of 1000 are obtained.

3ei entsprechender Arbeitsweise erhalt man Proukte der allgemeinen Formel (VIII) R' R" R"' Fp.[°C] R"' kg°C/Torr CH3 6-CH3 H 125-127 CH3 144/0,6 CH3 6-C2H5 H 81-83 CH3 130/0,3 Fumarat F.151° CH3 4,6C2H5 H 89 CH3 150°/0,3 CH3 6-C2H5 H 115-117 CH3 156°/0,4 C2H5 6-C2H56-CH3 H 103-105 CH3 155°/0,5 C2H5 4-CH3,6-CH3 H 119,5-120 CH3 149°/0,2 CH3 6-Cl H 91-92 CH3 140°/0,5 CH3 4-F,6-CH3 H 102-104 CH3 145°/0,4 C2H5 4-Cl-6-C2H5 CH3 160°/0,5 CH3 4-Cl-6CH3 H 92-93 CH3 155°/0,5 CF3 H H 137-138 CH3 138°/0,2 Cl 6-Cl H 172-173 CH3 162°/0,5 CH3 6-OCH3 H 119-120 CH3 152°/0,3 OCH3 6-OCH3 H 168-169 CH3 154°/0,2 OCH3 H H Hydrochlorid, CH3 146°/0,2 F. 108-110 R' R" R"' Fp.[°C] R"' kg°C/Torr CH3 4-OCH3,6-CH3 H 115-116 CH3 152°/0,2 CH3 4-OCH3,6-CH3 H 78,5 CH3 160°/0,2 CH(CH3)2 H H 81 CH3 128°/0,2 C2H5 H H 62 CH3 135°/0,2 CH3 H H 80 CH3 129°/0,2 Fumarat F. 150° CH3 5-CH3 H 118-119 CH3 138°/0,4 Cl 5-CF3 H Fumarat 181-183 Die freien Basen wie die Salze weisen starke akarizide Eigenschaften auf, besonders gegen Akariden, die als tierische Ektoparasiten domestizierte Tiere wie Rinder und Schafe befallen. Sie eignen sich deshalb gut für die Bekämpfung von tierischen Ektoparasiten aus der Ordnung der Akaridae.If the procedure is followed accordingly, products of the general formula (VIII) are obtained R'R "R"'m.p. [° C] R "' kg ° C / torr CH3 6-CH3 H 125-127 CH3 144 / 0.6 CH3 6-C2H5 H 81-83 CH3 130 / 0.3 fumarate M.p. 151 ° CH3 4.6C2H5 H 89 CH3 150 ° / 0.3 CH3 6-C2H5 H 115-117 CH3 156 ° / 0.4 C2H5 6-C2H56-CH3 H 103-105 CH3 155 ° / 0.5 C2H5 4-CH3,6-CH3 H 119.5-120 CH3 149 ° / 0.2 CH3 6-Cl H 91-92 CH3 140 ° / 0.5 CH3 4-F, 6-CH3 H 102-104 CH3 145 ° / 0.4 C2H5 4-Cl-6-C2H5 CH3 160 ° / 0.5 CH3 4-Cl-6CH3 H 92-93 CH3 155 ° / 0.5 CF3 HH 137-138 CH3 138 ° / 0.2 Cl 6 -Cl H 172-173 CH3 162 ° / 0.5 CH3 6-OCH3 H 119-120 CH3 152 ° / 0.3 OCH3 6-OCH3 H 168-169 CH3 154 ° / 0.2 OCH3 HH hydrochloride, CH3 146 ° / 0.2 m.p. 108-110 R'R "R"'m.p. [° C] R "' kg ° C / torr CH3 4-OCH3,6-CH3 H 115-116 CH3 152 ° /0.2 CH3 4-OCH3,6-CH3 H 78.5 CH3 160 ° / 0.2 CH (CH3) 2 HH 81 CH3 128 ° / 0.2 C2H5 HH 62 CH3 135 ° / 0.2 CH3 HH 80 CH3 129 ° / 0 , 2 fumarate m.p. 150 ° CH3 5-CH3 H 118-119 CH3 138 ° / 0.4 Cl 5-CF3 H fumarate 181-183 The free bases as well as the salts have strong acaricidal properties, especially against acarids, which attack domesticated animals such as cattle and sheep as animal ectoparasites. They are therefore well suited for combating animal ectoparasites from the order of the Akaridae.

hls wirtschaftlich wichtige Ektoparasiten dieser Art, die besonders in tropischen und subtropischen Länden eine große Rolle spielen, seien beispielsweise genannt: die australische und südamerikanische Itinderzecke BoophillÆs microplus, die südafrikanische Rinderzecke Boophilus decoloratus, beide aus der Pamilie der Ixodidae.hls economically important ectoparasites of this type, which are particularly play a major role in tropical and subtropical countries are, for example called: the Australian and South American Itinder tick BoophillÆs microplus, the South African beef tick Boophilus decoloratus, both of the family of Ixodidae.

Im Laufe der Zeit sind in verschiedenen Gebieten die genannten Zecken gegen die als Bekämpfungsmittel bisher verwendeten Phosphorsäureester und Carbamate resistent geworden, so daß der Bekämpfungserfolg dort in Frage gestellt wird.In the course of time, the above-mentioned ticks are in different areas against the phosphoric acid esters and carbamates previously used as control agents become resistant, so that the success of the control there is called into question.

Zur Sicherung einer wirtschaftlichen Viehhaltung in den Befallsgebieten besteht daher ein Bedarf an Mitteln, mit denen Zecken, auch resistenter Ste, beispielsweise des Genus Boophilus sicher bekämpft werden können. In hohem Ilaße gegen die bisherigen Phosphorsäureestermittel und Carbamate resistent sind beispielsweise in Australien der Ridgeland-Stamm und der Biarra-Stamm von Boophilus microplus.To ensure economic livestock farming in the infested areas There is therefore a need for means by which ticks, even more resistant Ste, for example of the genus Boophilus can be safely fought. In great disbelief against the previous ones Phosphoric acid ester agents and carbamates are resistant, for example, in Australia the Ridgeland strain and the Biarra strain of Boophilus microplus.

Die erfindungsgemäß zu verwendenden Wirkstoffe sind sowohl gegen die normalempfindlichen als auch die resistenten Stämme, zum Beispiel von Boophilus gleich gut wirksam, Sie wirken beispielsweise stark eiablagehemmend auf die adulten Spornen.The active ingredients to be used according to the invention are both against normal sensitive as well as resistant strains, for example Boophilus equally effective, for example, they have a strong egg deposition inhibiting effect on adults Spurs.

Die Applikation dieser Wirkstoffe erfolgt in üblicher Weise zum Beispiel durch Bespriihen, Begießen, Vernebeln oder als Bad (Dip). Den Formulierungen oder den anwendungsfertigen Lösungen können auch sonstige Hilfs- oder Wirkstoffe, wie Desinfektionsmittel, zugemischt werden.These active ingredients are applied in a customary manner, for example by spraying, dousing, misting or as a bath (dip). The formulations or The ready-to-use solutions can also contain other auxiliaries or active ingredients, such as Disinfectants.

Beispiel A In vitro-Test auf eiablagehemmende Wirkung an Zecken.Example A In vitro test for egg-deposition-inhibiting effect on ticks.

3 Teile Wirkstoff werden mit 7 Teilen eines Gemisches aus gleichen Gewichtsteilen Äthylenglykolmonomethyläther und Nonylphenolpolyglykoläther vermischt. Das so erhaltene Emulsionskonzentrat wird mit Wasser auf die jeweils gewünschte Anwendungskonzentration verdünnt.3 parts of active ingredient are equal to 7 parts of a mixture Parts by weight of ethylene glycol monomethyl ether and nonylphenol polyglycol ether mixed. The emulsion concentrate obtained in this way is adjusted to the desired in each case with water Application concentration diluted.

In diese Wirkstoffzubereitung werden adulte vollgesogene Zeckenweibchen der Art Boophilus microplus (resistent) eine Minute lang getaucht. Nach dem Tauchen von je 10 weiblichen Exemplaren der verschiedenen Zeckenstämme überführt man die einzelnen Zecken in Kunststoffschalen, deren Roden mit einer Filterpapierscheibe belegt ist. Nach 35 Tagen wird die Wirksamkeit der Wirkstoffzubereitung bestimmt durch Ermittlung der Hemmung der Ablage von fertilen eiern gegenüber der Eiablage von unbehandelten Kontrollzecken. Die Wirkung wird in 9"o angegeben, wobei 100% bedeutet, daß keine fertilen Eier mehr abgelegt wurden und 0 % bedeutet, daß die Zecken in normaler Weise wie die unbehandelten Kontrollzecken Eier abgelegt haben, Untersuchte Wirkstoffe, gepriEfte gonzentrationen, getestete Parasiten und erhaltene Befunde gehen aus der folgenden Tabelle hervor: T a b e l I In vitro Test auf ovicide Wirkung an Zecken: ovicide Wirkung gegen Boophilus microplus (Ridgeland-3tamm) 100 % >50 % Wirkstoff Hemmung bei einer Wirkstoff- konzentration in Gewichts- prozenten von Cl 8 N CH - 0,1 = OH - N\ 0,08 011 0113 3 (bekannt) Erfindungsgemäß zu verwendende Stoffe: d N = \ X 0,01 0,008 N 11 01ÜFN \N 0,01 0,005 cP3 tI 0011 0,03 0,02 11 0 N N = \ g 0,01 0,005 0F3 H CH3 I 0,1 0,03 N Be A 12 =$ä;J A 10 - 0,1 0,03 6113 Adult fully suckled female ticks of the species Boophilus microplus (resistant) are immersed for one minute in this active compound preparation. After 10 female specimens of each of the different tick strains have been immersed, the individual ticks are transferred to plastic trays, the clearing of which is covered with a filter paper disc. After 35 days, the effectiveness of the active compound preparation is determined by determining the inhibition of the laying of fertile eggs compared to the laying of eggs by untreated control ticks. The effect is given in 9 "o, where 100% means that no more fertile eggs were laid and 0% means that the ticks laid eggs in the normal way like the untreated control ticks Findings are shown in the following table: Table I In vitro test for ovicidal action on ticks: ovicidal action against Boophilus microplus (Ridgeland-3tamm) 100%> 50% Active ingredient inhibition in the case of an active ingredient concentration in weight percent of Cl 8 N CH - 0.1 = OH - N \ 0.08 011 0113 3 (known) Substances to be used according to the invention: d N = \ X 0.01 0.008 N 11 01ÜFN \ N 0.01 0.005 cP3 tI 0011 0.03 0.02 11 0 NN = \ g 0.01 0.005 0F3 H CH3 I 0.1 0.03 N Be A 12 = $ ä; JA 10 - 0.1 0.03 6113

Claims (1)

Patentansprüche: 1) Ektoparasiticide Mittel, gekennzeichnet durch einen Gehalt an 2-Arylimino-oxazolidinen und/oder deren Salzen der Formel in der R ilalogen wie Chlor, Fluor oder Brom, ferner Trifluormethyl, Alkyl, Alkenyl oder Alkoxy mit jeweils 1 - 4 C-Atomen Wasserstoff, Alkyl, Alkoxy, Alkenyl, Halogen wie Chlor, Brom, Fluor, Trifluormethyl oder Difluormethyl R"' Wasserstoff oder Methyl und n 1 oder 2 bedeuten. Claims: 1) Ectoparasiticides, characterized by a content of 2-arylimino-oxazolidines and / or their salts of the formula in the R ilalogues such as chlorine, fluorine or bromine, also trifluoromethyl, alkyl, alkenyl or alkoxy each with 1 - 4 carbon atoms hydrogen, alkyl, alkoxy, alkenyl, halogen such as chlorine, bromine, fluorine, trifluoromethyl or difluoromethyl R "'' hydrogen or methyl and n are 1 or 2. 3) Verwendung von 2-Arylimino-oxazolidinen gemäß Anspruch 1 zur Bekämpfung von Ecktoparasiten.3) Use of 2-arylimino-oxazolidines according to Claim 1 for combating of corner parasites. 4) Verfahren zur Herstellung von ektoparasiticiden Mitteln, dadurch gekennzeichnet, daß man 2-Arylimino-oxazolidine gegemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Mitteln mischt.4) Process for the preparation of ectoparasiticidal agents, thereby characterized in that 2-arylimino-oxazolidines according to claim 1 with extenders and / or mixes surfactants.
DE19691963192 1969-12-17 1969-12-17 2-arylimino-oxazolidines ectoparasiticides Pending DE1963192A1 (en)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0265162A1 (en) * 1986-10-17 1988-04-27 Stauffer Chemical Company Iminooxazolidines, process of preparation and method of use
WO1989004595A3 (en) * 1987-11-19 1989-07-27 Upjohn Co Ectoparasiticides
WO1996041534A1 (en) * 1995-06-08 1996-12-27 Bayer Aktiengesellschaft Use of oxazolines for combatting ectoparasites
US6353006B1 (en) 1999-01-14 2002-03-05 Bayer Corporation Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents
WO2007060121A1 (en) * 2005-11-25 2007-05-31 Basf Se Indanyl-and tetrahydronaphthyl-amino-azoline compounds for combating animal pests
WO2007093292A2 (en) * 2006-02-15 2007-08-23 Bayer Cropscience Ag Insecticidal substituted amino heterocyclic and heteroaryl derivatives
WO2008017649A1 (en) * 2006-08-07 2008-02-14 Basf Se Substituted azolin-2-yl-amino compounds
WO2008017816A2 (en) * 2006-08-07 2008-02-14 Syngenta Participations Ag Chemical compounds
EP1982595A1 (en) * 2007-04-17 2008-10-22 Bayer CropScience AG Insecticidal derivatives of substituted aminoheterocycles
WO2008155031A1 (en) * 2007-06-19 2008-12-24 Bayer Cropscience Ag Heterocyclic compounds for insecticides
US8426454B2 (en) 2007-08-15 2013-04-23 Allergan, Inc. Therapeutic compounds

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0265162A1 (en) * 1986-10-17 1988-04-27 Stauffer Chemical Company Iminooxazolidines, process of preparation and method of use
WO1989004595A3 (en) * 1987-11-19 1989-07-27 Upjohn Co Ectoparasiticides
WO1996041534A1 (en) * 1995-06-08 1996-12-27 Bayer Aktiengesellschaft Use of oxazolines for combatting ectoparasites
US6353006B1 (en) 1999-01-14 2002-03-05 Bayer Corporation Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents
US7981437B2 (en) 2005-11-25 2011-07-19 Basf Se Indanyl- and tetrahydronaphthyl-amino-azoline compounds for combating animal pests
WO2007060121A1 (en) * 2005-11-25 2007-05-31 Basf Se Indanyl-and tetrahydronaphthyl-amino-azoline compounds for combating animal pests
WO2007093292A2 (en) * 2006-02-15 2007-08-23 Bayer Cropscience Ag Insecticidal substituted amino heterocyclic and heteroaryl derivatives
WO2007093292A3 (en) * 2006-02-15 2008-01-10 Bayer Cropscience Ag Insecticidal substituted amino heterocyclic and heteroaryl derivatives
US8178567B2 (en) 2006-02-15 2012-05-15 Fmc Corporation Insecticidal substituted amino heterocyclic and heteroaryl derivatives
WO2008017816A2 (en) * 2006-08-07 2008-02-14 Syngenta Participations Ag Chemical compounds
WO2008017816A3 (en) * 2006-08-07 2008-04-03 Syngenta Participations Ag Chemical compounds
WO2008017649A1 (en) * 2006-08-07 2008-02-14 Basf Se Substituted azolin-2-yl-amino compounds
EP1982595A1 (en) * 2007-04-17 2008-10-22 Bayer CropScience AG Insecticidal derivatives of substituted aminoheterocycles
WO2008125230A2 (en) * 2007-04-17 2008-10-23 Bayer Cropscience Ag Insecticidal derivatives of substituted aminoheterocycles
WO2008125230A3 (en) * 2007-04-17 2010-05-06 Bayer Cropscience Ag Insecticidal derivatives of substituted aminoheterocycles
WO2008155031A1 (en) * 2007-06-19 2008-12-24 Bayer Cropscience Ag Heterocyclic compounds for insecticides
EP2014168A1 (en) * 2007-06-19 2009-01-14 Bayer CropScience AG Insecticidal heterocyclic compounds
US8426454B2 (en) 2007-08-15 2013-04-23 Allergan, Inc. Therapeutic compounds
US8815923B2 (en) 2007-08-15 2014-08-26 Allergan, Inc. Therapeutic compounds

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